- Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium
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A methanol extract of everlasting flowers of Helichrysum arenarium L. Moench (Asteraceae) was found to inhibit the increase in blood glucose elevation in sucrose-loaded mice at 500 mg/kg p.o. The methanol extract also inhibited the enzymatic activity against dipeptidyl peptidase-IV (DPP-IV, IC50 = 41.2 μg/ml), but did not show intestinal α-glucosidase inhibitory activities. From the extract, three new dimeric dihydrochalcone glycosides, arenariumosides V-VII (2-4), were isolated, and the stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Of the constituents, several flavonoid constituents, including 2-4, were isolated, and these isolated constituents were investigated for their DPP-IV inhibitory effects. Among them, chalconaringenin 2′-O-β-D-glucopyranoside (16, IC50 = 23.1 μM) and aureusidin 6-O-β-D-glucopyranoside (35, 24.3 μM) showed relatively strong inhibitory activities.
- Morikawa, Toshio,Ninomiya, Kiyofumi,Akaki, Junji,Kakihara, Namiko,Kuramoto, Hiroyuki,Matsumoto, Yurie,Hayakawa, Takao,Muraoka, Osamu,Wang, Li-Bo,Wu, Li-Jun,Nakamura, Seikou,Yoshikawa, Masayuki,Matsuda, Hisashi
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- A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells
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One new ursane-type triterpenoid glycoside, asiaticoside G (1), five triterpenoids, asiaticoside (2), asiaticoside F (3), asiatic acid (4), quadranoside IV (5), and 2α,3β,6β-trihydroxyolean-12-en-28-oic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl- (1→6)-β-d-glucopyranosyl] ester (6), and four flavonoids, kaempferol (7), quercetin (8), astragalin (9), and isoquercetin (10) were isolated from the leaves of Centella asiatica. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. The structure of new compound 1 was determined to be 2α,3β,23,30-tetrahydroxyurs-12-en-28- oic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl- (1→6)-β-d-glucopyranosyl] ester. The anti-inflammatory activities of the isolated compounds were investigated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Asiaticoside G (1) potently inhibited the production of nitric oxide and tumor necrosis factor-α with inhibition rates of 77.3% and 69.0%, respectively, at the concentration of 100 μM.
- Nhiem, Nguyen Xuan,Tai, Bui Huu,Quang, Tran Hong,Kiem, Phan Van,Minh, Chau Van,Nam, Nguyen Hoai,Kim, Jun-Ho,Im, Lee-Rang,Lee, Young-Mi,Kim, Young Ho
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- Reductive splitting of cellulose in the ionic liquid 1-butyl-3-methylimidazolium chloride
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The depolymerization of cellulose is carried out in the ionic liquid 1-butyl-3-methylimidazolium chloride in the presence of hydrogen gas. First, the ketal 1,1-diethoxycyclohexane and cel-lobiose were used as model substrates. For the depolymerization of cellulose itself, the combination of a heterogeneous metal catalyst and a homogeneous ruthenium catalyst proved effective. One of the possible roles of the ruthenium compound is to enhance the transfer of hydrogen to the metallic surface. The cellulose is fully converted under relatively mild conditions, with sorbitol as the dominant product in 51-74% yield.
- Ignatyev, Igor A.,Doorslaer, Charlie Van,Mertens, Pascal G. N.,Binnemans, Koen,De Vos, Dirk E.
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- Phenylbutanoids and stilbene derivatives of Rheum maximowiczii
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The methanol extract of the dried roots of Rheum maximowiczii afforded four phenylbutanoid and two stilbene derivatives. Their structures were established on the basis of chemical and spectroscopic studies.
- Shikishima, Yasuhiro,Takaishi, Yoshihisa,Honda, Gisho,Ito, Michiho,Takeda, Yoshio,Kodzhimatov, Olimjon K,Ashurmetov, Ozodbek
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- New direct production of gluconic acid from polysaccharides using a bifunctional catalyst in hot water
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Gluconic acid was produced from polysaccharides, such as starch and cellobiose, in water media at 393 K under air by a one-pot process using a bifunctional sulfonated activated-carbon supported platinum (Pt/AC-SO 3H) catalyst. Pt/AC-SO3H was prepared by the impregnation of platinum on activated-carbon (AC) and the sulfonation of the prepared Pt/AC. It was highly water-tolerant under hot aqueous solutions even including organic acids.
- Onda, Ayumu,Ochi, Takafumi,Yanagisawa, Kazumichi
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- Which controls the depolymerization of cellulose in ionic liquids: The solid acid catalyst or cellulose?
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Cellulose is a renewable and widely available feedstock. It is a biopolymer that is typically found in wood, straw, grass, municipal solid waste, and crop residues. Its use as raw material for biofuel production opens up the possibility of sustainable biorefinery schemes that do not compete with food supply. Tapping into this feedstock for the production of biofuels and chemicals requires-as the first-step-its depolymerization or its hydrolysis into intermediates that are more susceptible to chemical and/or biological transformations. We have shown earlier that solid acids selectively catalyze the depolymerization of cellulose solubilized in 1-butyl-3-methylimidazolium chloride (BMIMCl) at 100°C. Here, we address the factors responsible for the control of this reaction. Both cellulose and solid acid catalysts have distinct and important roles in the process. Describing the depolymerization of cellulose by the equivalent number of scissions occurring in the cellulosic chains allows a direct correlation between the product yields and the extent of the polymer breakdown. The effect of the acid strength on the depolymerization of cellulose is discussed in detail. Practical aspects of the reaction, concerning the homogeneous nature of the catalysis in spite of the use of a solid acid catalyst, are thoroughly addressed. The effect of impurities present in the imidazolium-based ionic liquids on the reaction performance, the suitability of different ionic liquids as solvents, and the recyclability of Amberlyst 15DRY and BMIMCl are also presented.
- Rinaldi, Roberto,Meine, Niklas,vom Stein, Julia,Palkovits, Regina,Schüth, Ferdi
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- Isatindigodiphindoside, an alkaloid glycoside with a new diphenylpropylindole skeleton from the root of Isatis indigotica
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A novel indole alkaloid glycoside with an unprecedented 2-(diphenylpropyl)indole skeleton, isatindigodiphindoside (1), was isolated from an aqueous extract of the roots of Isatis indigotica. The structure was determined by extensive spectroscopic studies, especially by 2D NMR data analysis combined with enzymatic hydrolysis and ECD calculations. Plausible biosynthetic pathways of compound 1 are also discussed.
- Meng, Ling-Jie,Guo, Qing-Lan,Zhu, Cheng-Gen,Xu, Cheng-Bo,Shi, Jian-Gong
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- Tetra-aryl cyclobutane and stilbenes from the rhizomes of Rheum undulatum and their α-glucosidase inhibitory activity: Biological evaluation, kinetic analysis, and molecular docking simulation
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One achiral tetra-aryl cyclobutane [rheundulin A (1)] and three stilbene glycosides [rheundulins B–D (2–4)] were isolated from the methanol extract of Rheum undulatum L., along with eight known compounds (5–12). Structural determination of the new compounds (1–4) was accomplished using comprehensive spectroscopic methods. Compound 1 represents the first example of a dimeric stilbene linked via a cyclobutane ring from the Rheum genus. All isolates were screened for their inhibition against α-glucosidase. Among them, stilbene derivatives (5 and 6) showed strong inhibitory effects on α-glucosidase with IC50 values of 0.5 and 15.4 μM, respectively, which were significantly higher than that of the positive control, acarbose (IC50 = 126.8 μM). Rheundulin A (1) showed moderate α-glucosidase inhibition with an IC50 value of 80.1 μM. In addition, kinetic analysis and molecular docking simulation of the most active compound (5) with α-glucosidase were performed for the first time. Kinetic studies revealed that compound 5 competitively inhibited the active site of α-glucosidase (Ki = 0.40 μM), while 6 had a mixed-type inhibitory effect against α-glucosidase (Ki = 15.34 μM). Molecular docking simulations of 5 and 6 demonstrated negative-binding energies, indicating high proximity to the active site and tight binding to α-glucosidase enzyme.
- Choi, Jae Sue,Ha, Manh Tuan,Kim, Chung Sub,Kim, Jeong Ah,Kim, Minji,Min, Byung Sun,Park, Se-Eun,Woo, Mi Hee
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- F-/Cl- mediated microwave assisted breakdown of cellulose to glucose
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Microwave irradiation of aqueous solution of cellulose in the presence of NaF/NaCl resulted into disintegration of cellulose to its monomeric unit, glucose (55%) in 20 min.
- Shaveta,Bansal, Neha,Singh, Palwinder
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- Indole alkaloids from the leaves of nauclea officinalis
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Three new indole alkaloids, named naucleamide G (1), and nauclealomide B and C (5 and 6), were isolated from the n-BuOH-soluble fraction of an EtOH extract of the leaves of Nauclea officinalis, together with three known alkaloids, paratunamide C (2), paratunamide D (3) and paratunamide A (4). The structures with absolute configurations of the new compounds were identified on the basis of 1D and 2D NMR, HRESIMS, acid hydrolysis and quantum chemical circular dichroism (CD) calculation. According to the structures of isolated indole alkaloids, their plausible biosynthetic pathway was deduced.
- Fan, Long,Liao, Cheng-Hui,Kang, Qiang-Rong,Zheng, Kai,Jiang, Ying-Chun,He, Zhen-Dan
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- New monoterpene glycosides from Paeonia suffruticosa Andrews and their inhibition on NO production in LPS-induced RAW 264.7 cells
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Nine new monoterpene glycosides (1-9), together with 18 known compounds were obtained from the n-butanol soluble fraction of ethanol extract from Paeonia suffruticosa Andrews. Their structures were determined on the basis of chemical methods and spectrosc
- Ding, Liqin,Zhao, Feng,Chen, Lixia,Jiang, Zhihu,Liu, Yue,Li, Zhuomin,Qiu, Feng,Yao, Xinsheng
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- TWO CHROMONE GLYCOSIDES FROM CASSIA MULTIJUGA
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Two new 2-methylchromone glycosides have been identified in the leaves of Cassia multijuga.Key Word Index - Cassia multijuga; Leguminosae; leaves; chromone glycosides.
- Singh, J.
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- Evaluation of the chemical quality of Sekkoku (石斛) in current Japanese commercial crude drugs: constituents of Flickingeria xantholeuca (Rchb. f.) A.D. Hawkes
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In our investigation, most Shihu (石斛; Japanese name, Sekkoku) in current Japanese commercial crude drugs were from Flickingeria xantholeuca (Orchidaceae). As the index compounds, three new ent-pimarane-type diterpenes, flickinxthanthosides A–C (1–3), one known analogue (7), and three new ent-kaurane-type diterpenes, flickinxanthosides D (4) and E (5) and flickinxanthol A (6) were isolated from the stem of F. xantholeuca. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and chemical methods. We attempted to detect these index compounds from the MeOH extracts of other Dendrobium or Flickingeria plants using TLC and LC/MS.
- Muto, Mei,Asahina, Haruka,Yoshioka, Tatsufumi,Ozaki, Kazuo,Shibano, Makio
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- GENISTEIN 7-(2"-p-COUMAROYLGLUCOSIDE) FROM TRIFOLIUM REPENS
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Key Word Index - Trifolium repens; Leguminosae; genistein 7-O-(2"-p-coumaroyl-β-D-glucopyranoside); isoflavone.A new acetylated isoflavone, genistein 7-(2"-p-coumaroylglucoside), has been characterized from Trifolium repens.
- Saxena, V. K.,Jain, A. K.
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- Pheonolic compounds from the fruits of Viburnum sargentii Koehne
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Seven phenolic compounds were isolated from the fruits of Viburnum sargentii Koehne by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as (-)-Epicatechin (1), 5,7,4′-trihydroxy-flavonoid-8-C-β-D-glucopyranoside (2), 1-(4-hydroxy-3-methoxyphenyl)- 2-[4-(3-α-L-rhamnopyranoxypropyl)-2-methoxyphenoxy]-1,3-propane-diol (erythro) (3), 1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-α-L-rhamnopyranoxypropyl)-2-methoxyphenoxy]- 1,3-propanediol (threo) (4), (R)-4-hydroxylphenol O-(6-O-oleuropeoyl)-β-D-glucopyranoside (5), (R)-3-methoxy-4-hydroxylphenol O-(6-O-oleuropeoyl)-β-D-glucopyranoside (6), quercetin-3-O-rutinoside (7). Compounds 5 and 6 are new monoterpene phenolic glycosides, compounds 1, 3 and 4 were isolated from the Viburnum genus for the first time, and compounds 2 and 7 from the Viburnum sargentii Koehne for the first time. Compounds 1-7 were also assayed for their antioxidant activities with DPPH free radicals.
- Xie, Yang,Wang, Jing,Geng, Yan-Mei,Zhang, Zhi,Qu, Yan-Fei,Wang, Guang-Shu
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- RADIOIMMUNOASSAY FOR THE QUANTITATIVE DETERMINATION OF HESPERIDIN AND ANALYSIS OF ITS DISTRIBUTION IN CITRUS SINENSIS
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A simple and sensitive radioimmumoassay (RIA) for the citrus flavanone hesperidin and other flavonoid 7-rutinosides is described.The assay utilizes antibodies raised against a hesperidin 4-O-carboxymethyl-oxime hapten and a tritiated radiotracer prepared by direct reduction of hesperidin with NaB4.The detection limit of the assay is 0.2 ng/0.1 ml (0.3 pmol/0.1 ml) and the measuring range extends to 10 ng/0.1 ml (16.4 pmol/0.1 ml).This assay is specific for flavonoid rutinosides, is characterized by a low coefficient of variation, and shows good correlation with HPLC for the quantification of hesperidin in oranges.The application of this method in determining the distribution of hesperidin in leaves, fruit, seeds, and seedlings of Citrus linensis is also reported.Key Word Index - Citrus sinensis; Rutaceae; radioimmunoassay; hesperidin; flavonoidglycosides; rutinosides.
- Barthe, Gary A.,Jourdan, Pablo S.,McIntosh, Cecilia A.,Mansell, Richard L.
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- Kribellosides, novel RNA 5′-triphosphatase inhibitors from the rare actinomycete Kribbella sp. MI481-42F6
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Yeast capping enzymes differ greatly from those of mammalian, both structurally and mechanistically. Yeast-type capping enzyme repressors are therefore candidate antifungal drugs. The 5′-guanine-N7 cap structure of mRNAs are an essential feature of all eukaryotic organisms examined to date and is the first co-transcriptional modification of cellular pre-messenger RNA. Inhibitors of the RNA 5′-triphosphatase in yeast are likely to show fungicidal effects against pathogenic yeast such as Candida. We discovered a new RNA 5′-triphosphatase inhibitor, designated as the kribellosides, by screening metabolites from actinomycetes. Kribellosides belong to the alkyl glyceryl ethers. These novel compounds inhibit the activity of Cet1p (RNA 5′-triphosphatase) from Saccharomyces cerevisiae in vitro with IC50s of 5-8 μM and show antifungal activity with MICs ranging from 3.12 to 100 μg ml-1 against S. cerevisiae.
- Igarashi, Masayuki,Sawa, Ryuichi,Yamasaki, Manabu,Hayashi, Chigusa,Umekita, Maya,Hatano, Masaki,Fujiwara, Toshinobu,Mizumoto, Kiyohisa,Nomoto, Akio
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- Polygonflavanol A, a novel flavonostilbene glycoside from the roots of Polygonum multiflorum
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Polygonflavanol A (1), a novel flavonostilbene glycoside with an unusual coupling pattern, together with five known stilbene glycosides (2-6), was isolated from the roots of Polygonum multiflorum. The structures were elucidated on the basis of extensive spectroscopic analysis and chemical evidence. The absolute configuration of 1 was further determined by CD analysis. Most of the compounds could inhibit nitric oxide (NO) secretion of RAW264.7 cells in respond to lipopolysaccharide (LPS) in a dose dependent manner. Among them, compound 2 displayed the highest inhibitory activity.
- Chen, Li-Li,Huang, Xiao-Jun,Li, Man-Mei,Ou, Guo-Min,Zhao, Bing-Xin,Chen, Min-Feng,Zhang, Qing-Wen,Wang, Ying,Ye, Wen-Cai
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- Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides
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Four new minor diterpene glycosides with a rare α-glucosyl linkage were isolated from a cyclodextrin glycosyltransferase glucosylated stevia extract containing more than 98% steviol glycosides. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl) ester] (1), 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl ester] (2), 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester (3), and 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl) ester] (4) on the basis of extensive NMR and mass spectral (MS) data as well as hydrolysis studies.
- Prakash, Indra,Chaturvedula, Venkata Sai Prakash
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- Benzylbenzoate and norlignan glucosides from Curculigo pilosa: Structural analysis and in vitro vascular activity
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From the rhizomes of Curculigo pilosa, two benzylbenzoate diglucosides, piloside A and piloside B, and a glucosyl-fused norlignan, pilosidine, previously obtained only as the tetra-O-methyl derivative, were isolated. Pilosidine showed facilitating effect on adrenaline evoked contractions in rabbit aorta isolated preparations. (C) 2000 Elsevier Science Ltd.
- Palazzino, Giovanna,Galeffi, Corrado,Federici, Elena,Delle Monache, Franco,Francesca Cometa, Maria,Palmery, Maura
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- Two new alkaloids from the roots of Baphicacanthus cusia
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Phytochemical investigation of the root of Baphicacanthus cusia (NEES) BREMEK afforded two new alkaloids, baphicacanthin A (1) and baphicacanthin B (2), along with 28 known compounds. The chemical structures of these compounds were elucidated on the basis of one and two dimensional (1D/2D)-NMR and high resolution (HR)-MS spectral evidence.
- Feng, Qi-Tong,Zhu, Guo-Yuan,Gao, Wei-Na,Yang, Zifeng,Zhong, Nanshan,Wang, Jing-Rong,Jiang, Zhi-Hong
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- Phenolic constituents from the roots of Alangium chinense
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Three new phenolics (1–3) and twenty-eight known compounds (4–31) were isolated from an ethanolic extract of roots of Alangium chinense. Compound 11 exhibited antiviral activity against Coxsackie virus B3 with IC50values of 16.89?μmol/L. Compou
- Zhang, Yan,Liu, Yun-Bao,Li, Yong,Ma, Shuang-Gang,Li, Li,Qu, Jing,Zhang, Dan,Jiang, Jian-Dong,Yu, Shi-Shan
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- New cholestane glycosides and sterols from the underground parts of Chamaelirium luteum and their cytotoxic activity
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Six new cholestane glycosides (1, 5, 6, 10, 12, and 13) and two new sterols (9 and 11), along with five known compounds (2-4, 7, and 8), were isolated from the underground parts of Chamaelirium luteum (Liliaceae). The structures of these new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds and aglycones were evaluated for their cytotoxic activity against HL-60 human leukemia cells. Compounds 6a, 10a, 12a, 13, and 13a were cytotoxic to HL-60 cells, with IC50 values of 12.8, 9.8, 15.3, 6.2, and 10.2 μM, respectively.
- Yokosuka, Akihito,Takagi, Kenichi,Mimaki, Yoshihiro
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- Dracopalmaside, a New Flavonoid from Dracocephalum palmatum
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Phytochemical studies of the aerial part of Dracocephalum palmatum (Lamiaceae) isolated the new flavonoid dracopalmaside that was identified based on UV, MS, and NMR spectral data as luteolin-7,4′-di-O-α -Lrhamnopyranosyl-(1→6)-β-D-glucopyranoside (luteolin-7,4′-di-O-rutinoside) and the two known compounds cynarotriside and luteolin-7,4′-di-O-glucoside.
- Olennikov,Chirikova
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- Two antiproliferative triterpene saponins from Nematostylis anthophylla from the highlands of central madagascar
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Investigation of the endemic Madagascan plant Nematostylis anthophylla (Rubiaceae) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the known triterpene saponin randianin (1), and the two new bioactive trit
- Dai, Yumin,Harinantenaina, Liva,Brodie, Peggy J.,Birkinshaw, Chris,Randrianaivo, Richard,Applequist, Wendy,Ratsimbason, Michel,Rasamison, Vincent E.,Shen, Yongchun,Tendyke, Karen,Kingston, David G. I.
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- Lasianosides A–E: New iridoid glucosides from the leaves of lasianthus verticillatus (Lour.) Merr. and their antioxidant activity
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The genus Lasianthus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the Lasianthus species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. Lasianthus verticillatus (Lour.) Merr. (Syn. Lasianthus trichophlebus auct. non Hemsl.) is a shrub, branchlets terete about 1.5–3 m in height. This paper studies the chemical composition of the leaves of L. verticillatus for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A–E (1–5), together with three known compounds (6–8). The undescribed structures of isolated compounds (1–5) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, 3 and 4 displayed potent radical scavenging activities with IC50 values of 30.2 ± 1.8 and 32.0 ± 1.2 μM, which were comparable to that of Trolox (29.2 ± 0.39 μM), respectively, while 5 possessed moderate activity with an IC50 value of 46.4 ± 2.3 μM. None of the isolated compounds exerted cytotoxicity against human cell line A549. As a result, lasianosides C, D, and E have the potential to be non-toxic safe antioxidant agents.
- Al-Hamoud, Gadah Abdulaziz,Orfali, Raha Saud,Perveen, Shagufta,Mizuno, Kenta,Takeda, Yoshio,Nehira, Tatsuo,Masuda, Kazuma,Sugimoto, Sachiko,Yamano, Yoshi,Otsuka, Hideaki,Matsunami, Katsuyoshi
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- Two new chlorophenyl glycosides from the bulbs of Lilium brownii var. viridulum
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Two rare new chlorophenyl glycosides, 2,4,6-trichlorol-3-methyl-5-methoxy- phenol 1-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside (1) and 4-chlorol-5-hydroxyl-3-methyl-phenol 1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (2), along with three kno
- Hong, Xiao-Xiao,Luo, Jian-Guang,Kong, Ling-Yi
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- Efficient production and separation of biodegradable surfactants from cellulose in 1-butyl-3-methylimidazolium chloride
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Alkyl glycoside biodegradable surfactants were produced from cellulose and 1-octanol or 1-dodecanol in a one-pot, two-step (hydrolysis-glycosidation) process in 1-butyl-3-methylimidazolium chloride. Both surfactant productivity and separation efficiencies have been strikingly enhanced compared to other previously reported ionic liquid processes. Production temperatures were decreased to limit the extent of glucose dehydration and further degradation processes, but the conversions remained high. Surfactant molar yields up to 72% were achieved by operating at 70°C. Several separation procedures were tested to achieve high recoveries of both surfactant and ionic liquid. The use of a silica stationary phase was useful for isolation of the surfactant, whereas crystallization of the ionic liquid improved its separation efficiency. Finally, the precipitation of dodecyl glycosides in aqueous media was highly efficient for their isolation and for the recovery (> 99 %) of the ionic liquid by using only water as the solvent for separation.
- Puga, Alberto V.,Corma, Avelino
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- Six new compounds from Atractylodes lancea and their hepatoprotective activities
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Two new phenolic glycosides with a rare β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl moiety (1, 2), one new dihydrobenzofuran derivative (3), one new pyrazine derivative (4), two new furofuran lignan glycosides (5, 6), and six known compounds (7–12) were isolated from the rhizomes of Atractylodes lancea. The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh2(OCOCF3)4-induced circular dichroism for configurational assignments. Notably, compounds 1–3 showed significant hepatoprotective activities against N-acetyl-p-aminophenol-induced HepG2 cell injury. This study is also the first Letter on the isolation of furofuran lignans and pyrazine derivatives (4–7) from the genus Atractylodes.
- Xu, Kuo,Yang, Ya-Nan,Feng, Zi-Ming,Jiang, Jian-Shuang,Zhang, Pei-Cheng
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- A study of the acid-catalyzed hydrolysis of cellulose dissolved in ionic liquids and the factors influencing the dehydration of glucose and the formation of humins
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An investigation was carried out into the hydrolysis of cellulose dissolved in 1-ethyl-3-methylimidazolium chloride ([Emim][Cl]) and 1-butyl-3- methylimidazolium chloride ([Bmim][Cl]) catalyzed by mineral acids. Glucose, cellobiose, and 5-hydroxymethylfurfural (5-HMF) were observed as the primary reaction products. The initial rate of glucose formation was determined to be of first order in the concentrations of dissolved glucan and protons and of zero order in the concentration of water. The absence of a dependence on water concentration suggests that cleavage of the β-1,4-glycosidic linkages near chain ends is irreversible. The apparent activation energy for glucose formation is 96kJmol-1. The absence of oligosaccharides longer than cellobiose suggests that cleavage of interior glycosidic bonds is reversible due to the slow diffusional separation of cleaved chains in the highly viscous glucan/ionic liquid solution. Progressive addition of water during the course of glucan hydrolysis inhibited the rate of glucose dehydration to 5-HMF and the formation of humins. The inhibition of glucose dehydration is attributed to stronger interaction of protons with water than the 2-OH atom of the pyranose ring of glucose, the critical step in the proposed mechanism for the formation of 5-HMF. The reduction in humin formation associated with water addition is ascribed to the lowered concentration of 5-HMF, since the formation of humins is suggested to proceed through the condensation polymerization of 5-HMF with glucose.
- Dee, Sean J.,Bell, Alexis T.
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- Hydrolysis of cellulose by amorphous carbon bearing SO3H, COOH, and OH groups
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The hydrolysis of cellulose into saccharides using a range of solid catalysts is investigated for potential application in the environmentally benign saccharification of cellulose. Crystalline pure cellulose is not hydrolyzed by conventional strong solid Bronsted acid catalysts such as niobic acid, H-mordenite, Nafion and Amberlyst-15, whereas amorphous carbon bearing SO3H, COOH, and OH function as an efficient catalyst for the reaction. The apparent activation energy for the hydrolysis of cellulose into glucose using the carbon catalyst is estimated to be 110 kJ mol-1, smaller than that for sulfuric acid under optimal conditions (170 kJ mol -1). The carbon catalyst can be readily separated from the saccharide solution after reaction for reuse in the reaction without loss of activity. The catalytic performance of the carbon catalyst is attributed to the ability of the material to adsorb β-1,4 glucan, which does not adsorb to other solid acids.
- Suganuma, Satoshi,Nakajima, Kiyotaka,Kitano, Masaaki,Yamaguchi, Daizo,Kato, Hideki,Hayashi, Shigenobu,Hara, Michikazu
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- Steroidal saponins from the underground parts of Ruscus a culeatus and their cytostatic activity on HL-60 cells
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Phytochemical examination of the underground parts of Ruscus aculeatus has been undertaken as part of a systematic study of plants of the Liliaceae. Six new spirostanol saponins and five new furostanol saponins were isolated, and their structures were assigned on the basis of spectroscopic analysis, including two-dimensional NMR techniques, and hydrolysis. Ruscogenin diglycoside with three acetyl groups attached to the inner galactosyl moiety and its corresponding 26-glucosyloxyfurostanol saponin showed cytostatic activity on leukemia HL-60 cells.
- Mimaki, Yoshihiro,Kuroda, Minpei,Kameyama, Aiko,Yokosuka, Akihito,Sashida, Yutaka
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- Flavonoids from Litsea japonica Inhibit AGEs Formation and Rat Lense Aldose Reductase in Vitro and Vessel Dilation in Zebrafish
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In our ongoing efforts to identify effective naturally sourced agents for the treating of diabetic complications, two new (1 and 2) and 11 known phenolic compounds (3-13) were isolated from an 80% ethanol extract of Litsea japonica leaves. The structures
- Lee, Ik-Soo,Kim, Yu Jin,Jung, Seung-Hyun,Kim, Joo-Hwan,Kim, Jin Sook
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- Two new secoiridoid glucosides and a new lignan from the roots of Ilex pubescens
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Two new secoiridoid glucosides, ilexpublignoside (1), pubzenoside (2), and a new lignan, ilexlignan B (3), along with seven known compounds (4–10) were isolated from the roots of Ilex pubescens for the first time. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including IR, UV, HR-ESI–MS, CD, NMR experiments, as well as comparison with the reported data.
- Zhang, Yang,Deng, Bowen,Cui, Yida,Chen, Xue,Bi, Jiayi,Zhang, Guogang
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- New Phenolic Compounds from the Roots of Lentil (Lens?culinaris)
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While lentil (Lens?culinaris) seeds are phytochemically well characterized, very little is known about secondary metabolites from lentil roots. Our research on lentil roots led to isolation of five phenolic compounds and five group B soyasaponins. Their structures were established using NMR spectroscopy and mass spectrometry. Four phenolics have not been hitherto described in the literature: 4-O-β-d-glucopyranosyl-2-methoxybenzoic acid, (αS)-4,4′-di-O-β-d-glucopyranosyl-α,2′-dihydroxydihydrochalcone, (αS)-4′-O-β-d-glucopyranosyl-α,2′,4-trihydroxydihydrochalcone, and keto-2-hydroxyglycitein. The DPPH?radical-scavenging activity of the purified phenolic compounds was additionally evaluated.
- ?uchowski, Jerzy,Pecio, ?ukasz,Reszczyńska, Emilia,Stochmal, Anna
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- Photodeprotection of up to Eight Photolabile Protecting Groups from a Single Glycan
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Permanent protecting groups are essential for oligosaccharide synthesis. However, the removal of the traditionally used protecting groups is not trivial and demands considerable expertise. Using photolabile protecting groups as permanent protection for glycan can overcome many limitations associated with the traditional oligosaccharide synthesis approach. It is demonstrated here that up to eight photolabile protecting groups can be readily removed from a single glycan using a benchtop LED setup that is very easy to operate. This report suggests that further development of the strategy will offer an attractive alternative for oligosaccharide synthesis.
- Samarasimhareddy, Mamidi,Alshanski, Israel,Mervinetsky, Evgeniy,Hurevich, Mattan
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- A new triterpene glycoside from the stems of Lagerstroemia indica
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A bioassay-guided fractionation and chemical investigation of the stems of Lagerstroemia indica resulted in the isolation and identification of a new triterpene glycoside, lagerindiside (1), along with nine known triterpenes (2–10). The structure of this new compound was elucidated on the basis of 1D and 2D nuclear magnetic resonance spectroscopic data analysis as well as chemical method. The cytotoxic activities of the isolates (1–10) were evaluated by determining their inhibitory effects on four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) using a sulforhodamine B bioassay. Compounds 3 and 4 showed potent cytotoxicity on the tumor cell lines with IC50values ranging from 3.38 to 6.29?μM.
- Woo, Kyeong Wan,Cha, Joon Min,Choi, Sang Un,Lee, Kang Ro
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- LILIOSIDE C, A GLYCEROL GLUCOSIDE FROM LILIUM LANCIFOLIUM
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A new glycerol glucoside, lilioside C, has been isolated from the leaves and stems of Lilium lancifolium.Its structure including the configuration of the aglycone moiety has been elucidated by chemical and spectroscopic means and by its synthesis.Key Word Index - Lilium lancifolium; Liliaceae; tiger lily; glycerol glucoside; 3-O-β-D-glucopyranosyl-sn-glycerol; lilioside C; stereochemistry; synthesis.
- Kaneda, Miyuki,Mizutani, Kiyoyasu,Tanaka, Keiko
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- The phenols and prodelphinidins of white clover flowers
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White clover flowers (Trifolium repens L.) contain an abundance of phenolics, namely cis- and tras-p-coumaric acid 4-O- β-D-glucopyranoside, the 3-O-β-D-galactopyranosides of myricetin, quercetin and kaempferol together with two new derivatives namely myricetin 3-O-(6''-acetyl)-β-D)- galactopyranoside and kaempferol 3-O-(6''-acetyl)-β-D)- galactopyranoside. Gallocatechin, epigallocatechin, gallocatechin-(4α-8)-epigallocatechin and their corresponding prodelphinidin polymers were also present. The 13C-NMR spectra showed that the polymers consisted of only gallocatechin and epigallocatechin monomeric units with the latter being about twice as abundant in the extenders but only slightly more than that in the terminating units. The average degree of polymerization was estimated by, 13C-NMR and ES-MS, which gave a remarkably consistent result of about 5.8 flavanol units. (C) 2000 Elsevier Science Ltd.
- Foo,Lu,Molan,Woodfield,McNabb
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- New Diterpenes from arenga pinnata (Wurmb.) merr. Fruits
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Three new ent-kauran-type diterpenes (1-3), named arenterpenoids A-C, and five known ones (4-8) were isolated and identified from Arenga pinnata (Wurmb.) Merr. Fruits. The structures of these compounds were established by 1D and 2D NMR spectra and HR-ESI-MS. To the best of our knowledge, this is the first scientific report of diterpenes from Arenga genus.
- Liu, Ji-Fei,Huo, Jin-Hai,Wang, Chang,Li, Feng-Jin,Wang, Wei-Ming,Huang, Lu-Qi
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- A new xanthone glycoside from the endolichenic fungus Sporormiella irregularis
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A new xanthone glycoside, sporormielloside (1), was isolated from an EtOAc extract of an endolichenic fungal strain Sporormiella irregularis (No. 71-11-4-1), along with two known xanthones (2, 3). Their structures were determined by detailed spectroscopic analysis (IR, MS, and 1D- and 2D-NMR), a chemical method, and a comparison of NMR data with closely related compounds previously reported. According to the structures of isolated compounds, their plausible biosynthetic pathway was deduced.
- Yang, Bin-Jie,Chen, Guo-Dong,Li, Yan-Jun,Hu, Dan,Guo, Liang-Dong,Xiong, Ping,Gao, Hao
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- Lignans from Lepidium meyenii and Their Anti-Inflammatory Activities
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Meyeniines A–C (1–3), three new lignans, two known neolignans (4–5), and three known lignans (6–8) were isolated from the rhizomes of Lepidium meyenii. Their structures were identified by comprehensive spectroscopic analyses and computational methods. Compound 1 represents a unique lignan featuring an aromatic ring migration. Compounds 2 and 4–6 were analyzed by chiral HPLC column as enantiomers. Biological evaluation revealed that compound 8 could inhibit IL-6 production in lipopolysaccharide (LPS) induced RAW264.7 cells in a dose-dependent manner.
- Zou, Yi-Yan,Wang, Dai-Wei,Yan, Yong-Ming,Cheng, Yong-Xian
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- Anti-complementary components of Helicteres angustifolia
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A first phenalenon derivative with an acetyl side chain at C-8, 8-acetyl-9-hydroxy-3-methoxy-7-methyl-1-phenalenon (compound 1), and a pair of new sesquilignan epimers at C-7″ of hedyotol C and hedyotol D analogs, hedyotol C 7″-O-β-D-glucopyranoside (compound 2) and hedyotol D 7″-O-β-D-glucopyranoside (compound 3) were isolated from the aerial parts of Helicteres angustifolia together with nine known compounds (4-12). Their structures were elucidated on the basis of spectroscopic methods, including mass spectroscopy, and 1D and 2D nuclear magnetic resonance. Eleven isolates exhibited anti-complementary activity. In particular, compounds 4 and 5 exhibited potent anti-complementary activities against the classical and alternative pathways with CH50 values of 0.040 ± 0.009 and 0.009 ± 0.002 mM, and AP50 values of 0.105 ± 0.015 and 0.021 ± 0.003 mM, respectively. The targets of compounds 4 and 5 in the complement activation cascade were also identified. In conclusion, the anti-complementary components of H. angustifolia possessed chemical diversity and consisted mostly of flavonoids and lignans in this study.
- Yin, Xiang,Lu, Yan,Cheng, Zhi-Hong,Chen, Dao-Feng
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- ISORHAMNETIN 7-GLUCOSIDE FROM CNICUS WALLICHI
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Key Word Index - Cnicus wallichi; Compositae; isorhamnetin 7-glucoside; flavonol glycoside.Isorhamnetin 7-glucoside was characterized from Cnicus wallichi.This is the first report of this glycoside in the Compositae and the second in nature.
- Singh, K. N.,Pandey, V. B.
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- Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: A chemoenzymatic route to sulforaphane
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A new semi-synthetic way to produce glucoraphanin (2), the bio-precursor of the potential anticarcinogen sulforaphane (3), has been developed. Starting from glucoerucin (1), isolated from ripe seeds of Eruca sativa, glucoraphanin was obtained through chemoselective oxidation. Controlled myrosinase-catalysed hydrolysis of this precursor quantitatively afforded sulforaphane.
- Iori,Bernardi,Gueyrard,Rollin,Palmieri
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- The phenolic acids from Oplopanax elatus Nakai stems and their potential photo-damage prevention activity
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25 phenolic acids, including four new isolates, eurylophenosides A–D (1–4) and 21 known ones (5–25) were isolated and identified from the stems of Oplopanax elatus Nakai. Among the known compounds 5–9, 11–13, 16, 18–25 were isolated from the genus for the first time; 17 was first obtained from the plant; and the NMR data of 22 was reported here first. Meanwhile, the UVB-induced photodamage model of HaCaT cells was used to study the prevent-photodamage abilities of compounds 1–2, 4–8, 11–13 and 15–25 with a nontoxic concentration at 50?μM. Moreover, a dose-dependent experiment was conducted for active compounds at the concentration of 10, 25, and 50?μM, respectively. Consequently, pretreatment with compounds 1, 16, 17, 19, 20, 22, 24 and 25 could suppress the cell viability decreasing induced by UVB irradiation in a concentration-dependent manner. These results indicated that phenolic acids were one kind of material basis with prevent-photodamage activity of O. elatus. Graphic abstract: [Figure not available: see fulltext.].
- Han, Yu,Cheng, Dongsheng,Hao, Mimi,Yan, Jiejing,Ruan, Jingya,Han, Lifeng,Zhang, Yi,Wang, Tao
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- New triterpenoid saponin from the stems of Albizia adianthifolia (Schumach.) W.Wight
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As part of our continuing study of apoptosis-inducing saponins from Cameroonian Albizia genus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated from Albizia adianthifolia stems. The s
- Toukea, Daniel Djou,Kamto, Eutrophe Le Doux,Simo, Line Made,Mbing, Joséphine Ngo,Antheaume, Cyril,Haddad, Mohamed,Noté, Olivier Placide,Pegnyemb, Dieudonné Emmanuel
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p. 780 - 788
(2020/08/19)
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- Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.
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The methanol extract from the leaves of Ilex paraguariensis A. St.-Hil. (Aquifoliaceae), popularly known as mate, maté, or yerba maté, inhibits the intracellular triglyceride accumulation in HepG2 cells and suppresses the plasma triglyceride elevation in olive oil-treated mice. Three new triterpene saponins, termed mateosides I (1), II (2), and III (3), were isolated from the extract along with 29 known compounds. The structures of 1–3 were elucidated based on chemical and spectroscopic evidence. Among the isolates, principal saponin constituents, 2 and matesaponins 1 (7) and 2 (9), potently inhibited the triglyceride accumulation in HepG2 cells simultaneously treated with oleic acid and high glucose. In vivo assay of the methanol extract of I. paraguariensis revealed that 7 and 9 showed anti-hyperlipidemic activities in olive oil-treated mice. These results suggested that the saponin constituents of I. paraguariensis could be valuable bioactive marker for the anti-obesogenic activity. Graphical abstract: [Figure not available: see fulltext.]
- Inoue, Naoki,Konno, Takuya,Manse, Yoshiaki,Morikawa, Toshio,Muraoka, Osamu,Nagatomo, Akifumi,Ninomiya, Kiyofumi,Sakamoto, Chinatsu,Shibasaka, Aya,Sone, Mayuko,Xu, Yin,Yoshikawa, Masayuki
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- Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides
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A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is
- Rasool, Javeed Ur,Kumar, Atul,Ali, Asif,Ahmed, Qazi Naveed
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p. 338 - 347
(2021/01/29)
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- Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
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A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.
- Traverssi, Miqueas G.,Pe?é?ory, Alicia B.,Varela, Oscar,Colomer, Juan P.
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p. 9262 - 9273
(2021/03/16)
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- Isolation, characterization, complete structural assignment, and anticancer activities of the methoxylated flavonoids from rhamnus disperma roots
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Different chromatographic methods including reversed-phase HPLC led to the isolation and purification of three O-methylated flavonoids; 5,4’-dihydroxy-3,6,7-tri-O-methyl flavone (penduletin) (1), 5,3’-dihydroxy-3,6,7,4’,5’-penta-O-methyl flavone (2), and 5-hydroxy-3,6,7,3’,4’,5’-hexa-O-methyl flavone (3) from Rhamnus disperma roots. Additionlly, four flavonoid glycosides; kampferol 7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-β-D-glucopyranoside (5), quercetin 7-O-α-L-rhamnopyranoside (6), and kampferol 3, 7-di-O-α-L-rhamnopyranoside (7) along with benzyl-O-β-D-glucopyranoside (8) were successfully isolated. Complete structure characterization of these compounds was assigned based on NMR spectroscopic data, MS analyses, and comparison with the literature. The O-methyl protons and carbons of the three O-methylated flavonoids (1–3) were unambiguously assigned based on 2D NMR data. The occurrence of compounds 1, 4, 5, and 8 in Rhamnus disperma is was reported here for the first time. Compound 3 was acetylated at 5-OH position to give 5-O-acetyl-3,6,7,3’,4’,5’-hexa-O-methyl flavone (9). Compound 1 exhibited the highest cytotoxic activity against MCF 7, A2780, and HT29 cancer cell lines with IC50 values at 2.17 μM, 0.53 μM, and 2.16 μM, respectively, and was 2–9 folds more selective against tested cancer cell lines compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 7 apoptotic populations and caused G1 cell cycle arrest. The acetylated compound 9 exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with IC50 values at 2.19 μM and 3.18 μM, respectively, and was 6–8 folds more cytotoxic to tested cancer cell lines compared to the MRC5 cells.
- Abd El-Wahab, Mohammed F.,Abdalla, Ashraf N.,Mohammed, Abd El-Salam I.,Mohammed, Hamdoon A.,Ragab, Ehab A.,Shaheen, Usama
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- Two-step biosynthesis of D-allulose via a multienzyme cascade for the bioconversion of fruit juices
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D-Allulose, a low-calorie rare sugar with potential as sucrose substitute for diabetics, can be produced using D-allulose 3-epimerase (DAE). Here, we characterized a putative thermostable DAE from Pirellula sp. SH-Sr6A (PsDAE), with a half-life of 6 h at 60 °C. Bioconversion of 500 g/L D-fructose using immobilized PsDAE on epoxy support yielded 152.7 g/L D-allulose, which maintained 80% of the initial activity after 11 reuse cycles. A multienzyme cascade system was developed to convert sucrose to D-allulose comprising sucrose invertase, D-glucose isomerase and PsDAE. Fruit juices were treated using this system to convert the high-calorie sugars, such as sucrose, D-glucose, and D-fructose, into D-allulose. The content of D-allulose among total monosaccharides in the treated fruit juice remained between 16 and 19% during 15 reaction cycles. This study provides an efficient strategy for the development of functional fruit juices containing D-allulose for diabetics and other special consumer categories.
- Li, Chao,Li, Lei,Feng, Zhiyuan,Guan, Lijun,Lu, Fuping,Qin, Hui-Min
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- Polythosides A and B, two new triterpenoid saponins from the roots of Acacia polyacantha Willd. (Mimosaceae)
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Two new oleanane-type triterpene saponins, named polythosides A and B (1 and 2), together with a known compound, silphioside E (3), were isolated from the roots of Acacia polyacantha. Their structures were elucidated by analysis of 1D and 2D-NMR experiments, and mass spectrometry (HR-ESITOF-MS) as oleanolic acid 3-O-β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranoside (1), 3-O-[β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl] oleanolic acid-28-O-β-D-glucopyranosyl ester (2) and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (3). The cytotoxic effect of isolated saponins was evaluated on the H4IIE rat hepatoma cell line. The results show that none of the compounds (assayed at 100 μM) showed cytotoxicity against H4IIE cells.
- Tchoukoua, Abdou,Tomfeun Nganou, Sandrine Carole,Dabole, Bernard,Yoshida, Jun,Ito, Yoshiaki,Ngadjui, Bonaventure Tchaleu,Shiono, Yoshihito
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p. 190 - 195
(2021/05/03)
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- α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus
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Diabetes mellitus is caused by chronic inflammation and affects millions of people worldwide. Cyclocarya paliurus leaves have been widely used in traditional folk tea as a remedy for diabetes, but the antidiabetic constituents remain to be further studied. The α-glucosidase inhibitory and anti-inflammatory activities were examined to evaluate their effects on diabetes mellitus, and bioassay-guided separation of C. paliurus leaves led to the identification of twenty dammarane saponins, including eleven new dammarane saponins (1–11). The structures of the isolates were elucidated by spectroscopic methods. Bioactivity assay results showed that compounds 1 and 2 strongly inhibited α-glucosidase activity, with IC50 values ranging from 257.74 μM, 282.23 μM, and strongly inhibited the release of NO, with IC50 values of 9.10 μM, 9.02 μM. Moreover, compound 2 significantly downregulated the mRNA expression of iNOS, COX-2, IL-1β, NF-κB, IL-6 and TNF-α in LPS-mediated RAW 264.7 cells and markedly suppressed the protein expression of iNOS, NF-κB/p65, and COX-2. Dammarane glucoside 2 exhibited the strongest α-glucosidase inhibitory and anti-inflammatory activities. In addition, the structure–activity relationships (SARs) of the dammarane saponins were investigated. In summary, C. paliurus leaves showed marked α-glucosidase inhibitory and anti-inflammatory activities, and dammarane saponins are responsible for regulating α-glucosidase, inflammatory mediators, and mRNA and the protein expression of proinflammatory cytokines, which could be meaningful for discovering new antidiabetic agents.
- Deng, Shengping,Hao, Lili,Huang, Xishan,Huang, Yan,Li, Chenguo,Li, Jun,Liang, Cheng-qin,Liu, Wei,Su, Shanshan,Xu, Xia,Yang, Ruiyun,Zhang, Gaorong,Zhou, Dexiong
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supporting information
(2021/07/22)
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- Bufadienolides and ecdysteroids from the whole plants of Helleborus niger and their cytotoxicity
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A new bufadienolide (1), two new bufadienolide glycosides (2 and 3), a new ecdysteroid (4), and four known compounds (5–8), were isolated from the whole plants of Helleborus niger L. (Ranunculaceae). The structures of the new compounds (1–4) were determined by spectroscopic analysis, including 2D NMR spectral data, and hydrolytic studies. Compounds 1–6 showed cytotoxicity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human small-cell lung cancer cells, with IC50 values ranging from 0.0055 to 1.9?μM. HL-60 cells treated with either 3 or 4 showed apoptosis characteristics, such as nuclear chromatin condensation, accumulation of sub-G1 cells, and activation of caspase-3/7.
- Yokosuka, Akihito,Inomata, Mina,Yoshizawa, Yuka,Iguchi, Tomoki,Mimaki, Yoshihiro
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p. 393 - 402
(2021/01/29)
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- Tetracyclic Triterpenoids, Steroids and Lignanes from the Aerial Parts of Oxypetalum caeruleum
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The MeOH extract from dried aerial parts of Oxypetalum caeruleum (Apocynaceae) plants yielded seventeen compounds, including four new tetracyclic triterpenoids, one pregnane glycoside, two lignane glycosides, and ten known compounds. The structures of the
- Warashina, Tsutomu,Shirota, Osamu
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p. 226 - 231
(2021/02/09)
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- Arenarosides A-G, Polyhydroxylated Oleanane-Type Saponins from Polycarpaea arenaria and their Cytotoxic and Antiangiogenic Activities
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Seven new polyhydroxylated oleanane-type triterpene saponins, arenarosides A-G (1-7), together with four known compounds, were isolated from an ethanol extract of the aerial parts of the Vietnamese plant Polycarpaea arenaria. The chemical structures of the newly isolated oleanane saponins were elucidated on the basis of spectroscopic and spectrometric analysis, especially 2D NMR and HRMS. Biological evaluation revealed that 3, 4, 6, and 7 showed moderate activities against four human cancer cell lines (A549, HTC116, PC3, and RT112) with IC50 values of 6.0-9.9 μM, and 3, 4, 5, and 7 also displayed promising antiangiogenesis effects with IC50 values 5 μM in the test system used. Among the isolates, arenaroside D (4) exhibited the most potent inhibitory effects, not only in cancer cell proliferation but also in angiogenic activities. Preliminary SAR studies revealed that the presence of an acetyl group at C-22 in oleanane-type triterpene saponins increases these bioactivities.
- Nguyen, Nham-Linh,Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Lu, Mei-Kuang,Cheng, Jing-Jy,Chen, Mei-Chuan,Kuo, Yao-Haur
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p. 259 - 267
(2021/02/06)
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- Antimicrobial, antimalarial, and cytotoxic substances from the insect pathogenic fungus Beauveria asiatica BCC 16812
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Six new compounds 1–6 and two new naturally occurring compounds 7 and 8, together with nine known compounds 9–14, beauverioride I, dipicolinic acid, and 6-(methoxycarbonyl) picolinic acid were isolated from a wasp-pathogenic fungus Beauveria asiatica, strain BCC 16812. Their structures were determined by extensive spectroscopic analyses. The absolute configurations of compound 6 were established by the application of modified Mosher's method and ECD calculation. Compounds 9–11 exhibited antimalarial (IC50 0.47–1.79 u g/mL), antimicrobial (MIC 3.13–50.0 u g/mL), and cytotoxic (IC50 0.26–1.23 u g/mL) activities, while compounds 1, 2, 8, and 14 showed only cytotoxicity against Vero cell lines, with IC50 values range 12.96–47.03 u g/mL.
- Kornsakulkarn, Jittra,Pruksatrakul, Thapanee,Surawatanawong, Panida,Thangsrikeattigun, Chattawat,Komwijit, Somjit,Boonyuen, Nattawut,Thongpanchang, Chawanee
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- Oleanane-type saponins and prosapogenins from Albizia julibrissin and their cytotoxic activities
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Two undescribed oleanane-type saponins, julibrosides K–L, along with three undescribed oleanane-type prosapogenins, julibrosides M–O, were isolated from the stem bark of Albizia julibrissin Durazz. and the mild alkaline hydrolysate of the total saponin, r
- Han, Qinghua,Qian, Yi,Wang, Xuda,Zhang, Qingying,Cui, Jingrong,Tu, Pengfei,Liang, Hong
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- Antioxidant and Cytoprotective Effects of New Diarylheptanoids from Rhynchanthus beesianus
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Rhynchanthus beesianus (Zingiberaceae) has been an important food spice and vegetable in southern China. Fifteen phenolic compounds (1-15) including three new diarylheptanoids, rhynchanines A-C (1-3) and one new phenylpropanoid, 4-O-methylstroside B (9), were isolated from R. beesianus rhizomes. The structures of new compounds were elucidated by comprehensive analyses through NMR, HRMS technique, acid hydrolysis, and Mosher's reaction. Among them, compound 5 is the first isolated natural product and its NMR data are reported. Most of the isolated compounds, especially 3-6 and 8, showed significant antioxidant activities on DPPH, ABTS+ radical scavenging, and FRAP assays. Furthermore, the antioxidant phenolic compounds were evaluated for their cytoprotective capacity against H2O2-induced oxidative stress in HepG-2 cells. Compounds 3 and 5 could significantly inhibit reactive oxygen species production, and compounds 3, 5, and 6 could remarkably prevent the cell apoptosis. Then, the R. beesianus rhizome, which contained phenolic compounds, might serve as a functional food for potential application on preventing oxidative stress-connected diseases.
- Zhu, Pei-Feng,Cheng, Gui-Guang,Zhao, Lan-Qin,Khan, Afsar,Yang, Xing-Wei,Zhang, Bu-Yun,Li, Meng-Cheng,Liu, Ya-Ping,Luo, Xiao-Dong
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p. 6229 - 6239
(2021/06/28)
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- Two New Phenolic Glycosides from Homalium stenophyllum
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A phytochemical study of the stems of Homalium stenophyllum Merr. & Chun led to the isolation of two new phenolic glycosides (1 and 2) and three known compounds (3–5). The molecular structures of these isolated new phenolic glycosides (1 and 2) were unambiguously established on the basis of comprehensive spectroscopic methods. All the isolated new compounds were evaluated for their cytotoxicities against three human cancer cell lines: HeLa, A-549, and MCF-7 in vitro.
- Chen, Guang-Ying,Chen, Zi-Ming,Han, Chang-Ri,Song, Xiao-Ping,Wu, Shou-Yuan
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p. 663 - 666
(2021/07/17)
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- Pseudosterins a–c, three 1-ethyl-3-formyl-β-carbolines from pseudostellaria heterophylla and their cardioprotective effects
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Pseudostellaria heterophylla is used in China not only as a functional food but also as an herb to tonify the spleen, enhance immunity, and treat palpitation. Our previous investigation showed that a fraction enriched in glycosides obtained from the roots of P. heterophylla possessed pronounced protective effects on H9c2 cells against CoCl2-induced hypoxic injury. However, the active compounds responsible for the observed effects were still unknown. In the current investi-gation, pseudosterins A–C (1–3), three new alkaloids with a 1-ethyl-3-formyl-β-carboline skeleton, together with polydatin, have been isolated from the active fraction. Their structures were elucidated on the basis of spectroscopic analysis and quantum chemical calculations. The four compounds showed cardioprotective effects against sodium hydrosulfite-induced hypoxia-reoxygenation injury in H9c2 cells, with the three alkaloids being more potent. This is also the first report of alkaloids with a β-carboline skeleton isolated from P. heterophylla as cardioprotective agents.
- Gan, Li-She,He, Xun,Liao, Shang-Gao,Liu, Jun,Wang, Fu-Rui,Wang, Yong-Lin,Wang, Zhen,Xu, Guo-Bo,Yang, Xin,Zhang, Chun-Li,Zhang, Jin-Juan,Zhou, Meng,Zhu, Qin-Feng
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- Undescribed chalcone and stilbene constituents from Lysimachia baviensis and their anti-inflammatory effect
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The chemical composition and anti-inflammatory activity of the endemic Lysimachia baviensis were investigated for the first time in this study. A phytochemical fractionation of the methanol extract of L. baviensis resulted in the isolation of a new stilbene (bavienside A, 1) and two new chalcone glycosides (baviensides B and C, 2 and 3). Their structures were elucidated via the interpretation of NMR and HRESIMS spectroscopic data. Compounds 1–3 strongly inhibited the production of nitric oxide in LPS-induced RAW264.7 cells with the IC50 values of 6.23, 2.86 and 3.51 μM, respectively. The C-acetylstilbene and carbomethyl chalcone structures in compound 1 and 3 were found for the first time from natural source and could be important markers for chemotaxonomy of Lysimachia baviensis.
- Dat, Nguyen Tien,Hau, Dang Viet,Hong Anh, Nguyen Thi,Hung, Nguyen Quang,Huong, Nguyen Thi Thanh,Khang, Nguyen Sinh,Luyenb, Nguyen Thi
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- Structure and cytotoxicity of novel lignans and lignan glycosides from the aerial parts of larrea tridentata
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Previously, the authors conducted phytochemical investigations of the aerial parts of Larrea tridentata and reported triterpene glycosides and lignan derivatives. In continuation of the preceding studies, 17 lignans and lignan glycosides (1–17) were isola
- Iguchi, Tomoki,Jitsuno, Maki,Mimaki, Yoshihiro,Yokosuka, Akihito
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- Mimonoside D: a new triterpenoid saponin from Mimosa diplotricha Sauvalle (Fabaceae)
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A new triterpenoid saponin (Mimonoside D: 3-O-α-L-arabinopyranosyl-3β-hydroxyolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1→2)-β-D- glucopyranoside ester (1)) was isolated from the aerial parts of Mimosa diplotricha Sauvalle together with nine known compounds: 7,4′-dihydroxyflavone (2), kaempferol (3), lupeol (4), betulinic acid (5), β-sitosterol (6), β-sitosterol-3-O-β-D-glucopyranoside (7), lutein (8), 5,2′-dihydroxy-7,4′,5′-trimethoxyflavone (9) and vitexin (10). Their structures were elucidated on the basis of spectroscopic (1D and 2D nuclear magnetic resonance) and high-resolution mass spectrometric data as well as by comparison of their spectral data with those of related compounds. Compounds 2, 7 and 8 had already been isolated from M. diplotricha, while compounds 3, 4, 5 and 6 have been isolated from other Mimosa species. Compound 2 moderately inhibited Proteus mirabilis (MIC = 32μg/mL), weakly inhibited Pseudomonas aeruginosa (MIC = 64μg/mL) and very weakly inhibited Staphylococcus aureus (MIC = 128μg/mL) and Enterococus faecalis (MIC = 128μg/mL).
- Dzoyem, Jean Paul,Kemkuignou, Blondelle Matio,Kenmogne, Claudie Fokou,Opatz, Till,Ponou, Beaudelaire Kemvoufo,Tchuenguem, Roland T.,Kühlborn, Jonas,Tapondjou, Léon Azefack,Teponno, Rémy Bertrand
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- Steroidal Glycosides from the Aerial Parts of Avena sativa L. And Their Cytotoxic Activity
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Twelve steroidal glycosides (1-12) were isolated from the aerial parts of Avena sativa L. (Poaceae). Among the isolated compounds, 1 was directly isolated from the plant for the first time, and 2-6 were new steroidal glycosides. The structures of 1-6 were determined by analysis of their spectroscopic data, chemical transformations, and chromatographic and spectroscopic analyses of the hydrolyzed products. Compounds 5 and 6 were novel steroidal glycosides with a B-ring contracted skeleton (B-nor steroid). Compounds 1, 9, 11, and 12 were cytotoxic to HL-60 human promyelocytic leukemia cells, MIA PaCa-2 human pancreatic carcinoma cells, and A549 human lung adenocarcinoma cells with IC50 values ranging from 0.79 to 13.5 μM. HL-60 cells treated with 1 exhibited apoptotic characteristics, namely, condensed nuclear chromatin, accumulation of sub-G1 cells, and activation of caspase-3. Additionally, the loss of the mitochondrial membrane potential and the release of cytochrome c into the cytoplasm in 1-treated HL-60 cells suggested that 1 induced apoptosis through a mitochondrial-dependent apoptotic pathway.
- Iguchi, Tomoki,Ishihara, Keita,Mimaki, Yoshihiro,Yamada, Tsuyoshi,Yokosuka, Akihito
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p. 14568 - 14579
(2021/12/13)
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- Discovery of glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates with anti-inflammatory activities from Pleione grandiflora
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Six new glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates, pleionesides A-F (1–6), along with two known compounds (7, 8) were obtained from the pseudobulbs of Pleione grandiflora (Rolfe) Rolfe. The structures and absolute configurations of new compounds were established by HRESIMS and NMR data, along with acidic hydrolysis and alkaline hydrolysis experiments. Compounds 1–6 were tested for their anti-inflammatory activities on LPS-induced BV2 microglial cells. Amoung them, 2, 4 and 5 showed moderate activities with IC50 values of 73.4, 32.8 and 57.1 μM, respectively, compared with the positive control quercetin with an IC50 value of 28.3 μM.
- Fu, Jiarui,Ni, Lin,Wu, Meiting,Wu, Shasha,Wu, Xiaoqian,Zhang, Linjing,Zhang, Xiaoqin,Zheng, Lijun
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- Stilbene dimer xylosides and flavanols from the roots of Lysidice rhodostegia and their antioxidant activities
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Eight new stilbene dimer xylosides (1–8) and one new flavanol (9), along with seven known ones (10–16) were isolated from the roots of Lysidice rhodostegia. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HR-ESI-MS, 1D and 2D NMR), ECD calculations and acid hydrolysis. Compounds 1–16 were evaluated for their antioxidant activities using DPPH radical-scavenging assay. Especially, compounds 9 and 10 exhibited stronger antioxidant effects than the positive control (vitamin E), with IC50 values of 9.57 ± 1.30 and 13.60 ± 1.47 μM, respectively.
- Li, Yao-Lan,Li, Ying-Ying,Tang, Qing,Wang, Guo-Cai,Wang, Wen-Zhi,Wu, Zhong-Nan,Zhan, Zhao-Chun,Zhang, Sheng-Yuan,Zhang, Yu-Bo
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- Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)
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There are about 200 holoparasitic broomrapes (Orobanchaceae) known worldwide, however, only several species have been so far investigated phytochemically. Among Orobanche s.l. are both rare and endangered species, as well as onerous crop pests. This study aims to give a phytochemical description, both qualitative and quantitative, of six broomrape species (Orobanche and Phelipanche taxa) growing in Poland, including species that have not been tested in detail (O. caryophyllacea, O. lutea, O. picridis, and P. arenaria). Sixteen metabolites, including 14 phenylethanoid glycosides (PhGs) and 2 iridoid glycosides (IrGs), were isolated and identified using NMR spectroscopy and hydrolysis, revealing the presence of two previously undescribed PhGs in P. ramosa, named ramoside A and 2′-acetylramoside A. In addition, in the example of O. caryophyllacea, we have reported as the first occurrence of IrGs in broomrapes. Concentrations of phenylethanoids, the main constituents of broomrapes, in the studied plant material (flowering shoots with haustoria) were determined using the UHPLC-PDA method. It was found that P. ramosa has been the richest source of PhGs. In addition, the differences between broomrapes have been visualized using principal component and cluster analysis. The results of the antiradical DPPH test of 13 PhGs confirmed previous findings on the relation of the antioxidant potential with the structure of phenolic moieties – phenolic acid and phenylethanoid unit.
- Jedrejek, Dariusz,Pawelec, Sylwia,Piwowarczyk, Renata,Pecio, ?ukasz,Stochmal, Anna
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- Tunable acidity in mesoporous carbons for hydrolysis reactions
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A mesoporous carbon (CMC) has been treated under acidic conditions (32.5 wt% HNO3 at 10 °C or 40 °C) to prepare two new carbon samples (HCMC10 and HCMC40), which developed higher acidity in terms of quantity of sites and surface acid strength. The properties of the three carbons have been studied by using various techniques (N2 adsorption/desorption, TEM, XRPD, Raman spectroscopy, 13C NMR, 2D 1H-13C NMR, and XPS). Aromatic -COOH and -OH groups were identified as the main surface acid sites. Acid site density has been determined by pulse liquid-solid phase adsorption experiments carried out in different liquids. The samples retained acidity features in water, due to hydrophobicity of the surfaces, while acidity dropped when measured in methanol. From NH3-TPD analysis, a ranking of acid strength could be obtained: HCMC40 > HCMC10 > CMC. The good acidity of the carbon samples allowed them to act as catalysts in the hydrolysis reaction of sucrose to glucose and fructose. The catalytic activity of the carbon samples was compared to that of Amberlite, a commercial sulfated acid resin; the observed kinetic constant of HCMC40 was similar to that of Amberlite.
- Ferri,Campisi,Carniti,Gervasini,Shen
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supporting information
p. 5873 - 5883
(2020/04/29)
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- Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor
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Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.
- Tiwari, Varsha,Badavath, Vishnu Nayak,Singh, Adesh Kumar,Kandasamy, Jeyakumar
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p. 227 - 236
(2020/03/18)
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- Angustifolinoid B, a flavonoid glycoside dimer with cyclobutane from Elaeagnus angustifolia flowers
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A novel flavonoid glycoside dimer with an unprecedented cyclobutane moiety, named angustifolinoid B (1), was isolated from Elaeagnus angustifolia flowers. Its structure was determined by extensive spectroscopic analysis (HRMS, NMR) and chemical hydrolysis. The new dimer was formed via a [2 + 2] cycloaddition between two symmetric tiliroside. Bioassay revealed that compound 1 showed significant α-glucosidase inhibitory activity with IC50 value at 4.40 μM.
- Xie, Huijun,Chen, Xiaoyu,Li, Miaomiao,Aisa, Haji Akber,Yuan, Tao
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supporting information
(2020/04/21)
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- Identification of potential anti-inflammatory and melanoma cytotoxic compounds from Aegiceras corniculatum
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Many chemicals found in mangroves reportedly exhibit potent anticancer, antibacterial, anti-inflammatory, antioxidant, and antitumor properties. Several of such compounds include feature unique structures and display interesting pharmacological effects. Few medicinal mangrove plants from Vietnam have been characterized with regard to their chemical constituents. Aegiceras corniculatum (L.) Blanco is a mangrove shrub that exhibits activity against various types of cancer. To identify new secondary metabolites and determine the source(s) of biological activity in Vietnamese medicinal mangrove plants, the chemical constituents of A. corniculatum were isolated, and their structures were appropriately established using common spectroscopic methods (1D and 2D-NMR, IR, HR-ESI-MS), and by producing derivatives by chemical reactions. Complementarily, it is worth noting, that the anti-inflammatory effects of the isolated compounds were investigated by measuring the production of pro-inflammatory cytokines IL-12 p40, IL-6, and TNF-α in lipopolysaccharide-stimulated bone marrow-derived dendritic cells; in this sense, the target compounds 2 and 3 were potent inhibitors of cytokines TNF-α, IL-6, and IL-12 p40, indicating promising anti-inflammatory effects. Furthermore, compounds 1 and 4 strongly promoted apoptosis of B16F10 melanoma cells. It is convenient to highlight, that the obtained results suggest that saponins from A. corniculatum could be potential candidates for treating cancer and inflammatory illnesses.
- Vinh, Le Ba,Phong, Nguyen Viet,Ali, Irshad,Dan, Gao,Koh, Young Sang,Anh, Hoang Le Tuan,Van Anh, Do Thi,Yang, Seo Young,Kim, Young Ho
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p. 2020 - 2027
(2020/09/01)
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- Microbial transformation of prenylquercetins by mucor hiemalis
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Quercetin, one of the most widely distributed flavonoids, has been found to show various biological activities including antioxidant, anticancer, and anti-inflammatory effects. It has been reported that bioactivity enhancement of flavonoids has often been closely associated with nuclear prenylation, as shown in 8-prenylquercetin and 5′-prenylquercetin. It has also been revealed in many studies that the biological activities of flavonoids could be improved after glucosylation. Three prenylated quercetins were prepared in this study, and microbial transformation was carried out in order to identify derivatives of prenylquercetins with increased water solubility and improved bioavailability. The fungus M. hiemalis was proved to be capable of converting prenylquercetins into more polar metabolites and was selected for preparative fermentation. Six novel glucosylated metabolites were obtained and their chemical structures were elucidated by NMR and mass spectrometric analyses. All the microbial metabolites showed improvement in water solubility.
- Han, Fubo,Xiao, Yina,Lee, Ik-Soo
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- Steroidal saponins from Trillium tschonoskii rhizomes and their cytotoxicity against HepG2 cells
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A phytochemical study on the rhizomes of Trillium tschonoskii led to the isolation of fourteen new steroidal saponins, trillitschosides S1-S14 (1–14), along with ten known analogues (15–24). Their structures were established mainly by spectroscopic analyses as well as necessary chemical evidence. All isolated compounds were screened for the cytotoxicity against HepG2 cells, and the results demonstrated that only the known compounds 21–24 exhibited the remarkable cytotoxic activity against HepG2 cells which is much better than the positive control of 5-FU.
- Chen, Xiao-Juan,Guo, Bao-Lin,Li, Qi,Ma, Bai-ping,Pang, Xu,Sun, Xin-Guang,Wang, Bei,Yang, Jie,Yang, Yin-Jun,Zhang, Jie
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- New dammarane-type triterpenoid saponins from Panax notoginseng leaves and their nitric oxide inhibitory activities
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Inflammation is a very common and important pathological process that can cause many diseases. The discovery of anti-inflammatory drugs and the treatment of inflammation are particularly essential. Dammarane-type triterpenoid saponins (PNS) were demonstrated to show anti-inflammatory effects in the leaves of Panax notoginseng. Chromatographies and spectral analysis methods were combined to isolate and identify PNS. Moreover, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As a result, eleven new dammarane-type triterpenoid saponins, notoginsenosides NL-A1-NL-A4 (1-4), NL-B1-NL-B3 (5-7), NL-C1-NL-C3 (8-10), and NL-D (11) were isolated, and their structures were identified by using various spectrometric techniques and chemical reactions. Among them, compounds 4 and 11 were characterized by the malonyl substitution at 3-position. The 3-malonyl substituted dammarane-type terpennoids were first obtained from natural products. In addition, compounds 1, 2, 5, 6, and 8-10 were found to play an important role in suppressing NO levels at 50 μM, without cytotoxicity. All inhibitory activities were found to be dose-dependent.
- Hao, Mimi,Ruan, Jingya,Sun, Fan,Wang, Tao,Wu, Lijie,Xiang, Guilin,Yan, Jiejing,Zhang, Yi,Zhang, Ying,Zhao, Wei
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- Tuning Ca-Al-based catalysts' composition to isomerize or epimerize glucose and other sugars
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One of the key reactions to achieve good productivity in the transformations of cellulose derived from biomass feedstocks is the isomerization of glucose to fructose, the latest being the platform molecule for obtaining other important derivatives. In this work, Ca-Al containing catalysts based on hydrotalcite-type derived materials were used to perform the selective isomerization of glucose to fructose, and the selective epimerization of glucose to mannose, using water as the solvent under mild reaction conditions. The catalysts showed high activity (conversion = 51-87%), and excellent selectivity (63-88%) towards fructose, compared with the current industrial process based on the glucose transformation via biocatalysis. It was also possible to modulate the selectivity towards fructose or mannose by tuning the amount of basic sites of the catalysts and their composition. The combination of basic and acid sites present in the Ca-Al-based catalysts plays a key role in the reaction, a fact that is discussed in the text together with other important operational parameters. The stability and recyclability of the catalysts were tested, detecting only a small activity loss after 5 consecutive runs. The synthesis of the catalysts and their characterization are also discussed since they are one of the few cases found in the literature of this kind of hydrotalcite-type material with such a high level of Ca incorporation. Some green metrics, such as E-factor, have been calculated to evaluate our system as an environmentally friendly process.
- Ventura, Maria,Cecilia, Juan A.,Rodríguez-Castellón, Enrique,Domine, Marcelo E.
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p. 1393 - 1405
(2020/03/11)
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- Triterpenic saponins from Medicago marina L
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The saponin composition of leaves and roots from Medicago marina L., sea medic, was investigated by a combination of chromatographic, spectroscopic and spectrometric (GC, LC, ESI-MS/MS, NMR) methods. Several compounds were detected and quantified by HPLC using the external standard method. Saponins from this plant species consist of a mixture of high molecular weight bidesmosidic derivatives of medicagenic and zanhic acid, containing up to six sugars in the molecules. Six of the detected saponins were previously isolated and reported as constituents of other Medicago spp.; one saponin was previously described in other plant species; four saponins are undescribed compounds in Medicago and never reported before in other plant species. These are: 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[β-D-apiofuranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester and 3-O-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester. The specific saponins synthesized by M. marina may have a role in its tolerance to environment, representing a reservoir of osmolytic sugars.
- Accogli, Rita,Argentieri, Maria Pia,Avato, Pinarosa,Biazzi, Elisa,Doria, Filippo,Mella, Mariella,Ronga, Domenico,Tava, Aldo
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- Five new pregnane glycosides from Gymnema sylvestre and their α-glucosidase and &alphla;-amylase inhibitory activities
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Gymnema sylvestre, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of Gymnema sylvestre led to the isolation of five new pregnane glycosides, gymsylosides A-E (1-5) and four known oleanane saponins, 3β-O-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (6), gymnemoside-W1 (7), 3β-O-β-D-xylopyranosyl-(1→6)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (8), and alternoside XIX (9). Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for their α-glucosidase and α-amylase inhibitory activities. Compounds 2-4 showed significant α-amylase inhibitory activity, with IC50 values ranging from 113.0 to 176.2 μM.
- Kim, Seung Hyun,Kim, Sun Yeou,Lee, Jae Hyuk,Ngoc, Tran Minh,Nhiem, Nguyen Xuan,Park, Seon Ju,Tai, Bui Huu,Trang, Do Thi,Van Hung, Nguyen,Van Kiem, Phan,Van Minh, Chau,Yen, Duong Thi Hai,Yen, Pham Hai
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- Steroidal saponins and sapogenins from fenugreek and their inhibitory activity against α-glucosidase
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The seed of Trigonella foenum-graecum L. (fenugreek) has been reported to be rich in saponins, especially the dioscin or diosgenin, which are natural anti-diabetic agents with relatively low toxicity. Thus, the present study was to purify the saponins and sapogenins from fenugreek and to evaluate their α-glucosidase inhibitory activity in vitro. As a result, 33 steroidal saponins and sapogenins were isolated, including six undescribed ones and 27 previously known molecules. Among them, compounds 10, 12, 17, 22 and 29 were five 25R and 25S isomer mixtures of spirostanol saponins or sapogenins. The structures of compound 1–6 were established by 1D and 2D NMR spectroscopic analyses, high-resolution mass spectrometry, and chemical evidence. Compared to the positive control, sapogenins 26, 27, 14 and saponins 18 and 23 considerably inhibited α-glucosidase at IC50 values of 15.16, 8.98, 7.26, 5.49 and 14.01 μM, respectively. These results support the therapeutic potential of fenugreek in the treatment of diabetes with saponins and sapogenins as the active constituents.
- Dai, Rongke,Wang, Meizhe,Xia, Xiaoyan,Xu, Jing,Zhang, Huixing,Zhao, Yuqing
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- New cytotoxic cerebrosides from the red sea cucumber Holothuria spinifera supported by in-silico studies
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Bioactivity-guided fractionation of a methanolic extract of the Red Sea cucumber Holothuria spinifera and LC-HRESIMS-assisted dereplication resulted in the isolation of four compounds, three new cerebrosides, spiniferosides A (1), B (2), and C (3), and cholesterol sulfate (4). The chemical structures of the isolated compounds were established on the basis of their 1D NMR and HRMS spectral data. Metabolic profiling of the H. spinifera extract indicated the presence of diverse secondary metabolites, mostly hydroxy fatty acids, diterpenes, triterpenes, and cerebrosides. The isolated compounds were tested for their in vitro cytotoxicities against the breast adenocarcinoma MCF-7 cell line. Compounds 1, 2, 3, and 4 displayed promising cytotoxic activities against MCF-7 cells, with IC50 values of 13.83, 8.13, 8.27, and 35.56 μM, respectively, compared to that of the standard drug doxorubicin (IC50 8.64 μM). Additionally, docking studies were performed for compounds 1, 2, 3, and 4 to elucidate their binding interactions with the active site of the SET protein, an inhibitor of protein phosphatase 2A (PP2A), which could explain their cytotoxic activity. This study highlights the important role of these metabolites in the defense mechanism of the sea cucumber against fouling organisms and the potential uses of these active molecules in the design of new anticancer agents.
- Abdelhameed, Reda F.A.,Eltamany, Enas E.,Hal, Dina M.,Ibrahim, Amany K.,AboulMagd, Asmaa M.,Al-Warhi, Tarfah,Youssif, Khayrya A.,Abd El-Kader, Adel M.,Hassanean, Hashim A.,Fayez, Shaimaa,Bringmann, Gerhard,Ahmed, Safwat A.,Abdelmohsen, Usama Ramadan
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- New 12,23-epoxydammarane type saponins obtained from panax notoginseng leaves and their anti-inflammatory activity
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Two new 12,23-epoxydammarane-type saponins, notoginsenosides NL-I (1) and NL-J (2), were isolated and identified from Panax notoginseng leaves through the combination of various chromatographies and extensive spectroscopic methods, as well as chemical reactions. Among them, notoginsenoside NL-J (2) had a new skeleton. Furthermore, the lipopolysaccharide (LPS)-induced RAW 264.7 macrophage model was used to identify the in vitro anti-inflammatory activity and mechanisms of compounds 1 and 2. Both of them exerted strong inhibition on nitric oxide (NO) productions in a concentration-dependent manner at 1, 10, and 25 μM. Moreover, these two compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), interleukin 6 (IL-6), cyclooxygenase-2 (COX-2), nuclear factor kappa-B (NF-κB/p65), and nitric-oxide synthase (iNOS) in LPS-activated RAW 264.7 cells.
- Han, Lifeng,Ruan, Jingya,Sun, Fan,Wang, Tao,Wu, Lijie,Yu, Haiyang,Zhang, Yi,Zhang, Ying,Zhao, Wei
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- Two new acylated triterpenoidal saponins from Gleditsia caspica Desf. and the effect of its saponin content on LPS-induced cognitive impairment in mice
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Two bisdismosidic triterpenoidal saponins, caspicaoside A1 (1) and caspicaoside B1 (2), were isolated from Gleditsia caspica fruit methanolic extract. The structures of 1 and 2 were determined using chemical and spectral techniques. Gleditsia caspica fruit methanolic extract (MEGC) and its saponin containing fraction (SFGC) at the two dose levels 45 and 90 mg/kg b.wt. were studied comparatively for their effect on LPS-induced cognitive impairment in mice using Ginkgo biloba (100 mg/kg b.wt.) as a standard drug. Neurobehavioral tests (Morris Water Maze and Novel Object Recognition tests) were conducted to prove that MEGC and SFGC at the two levels were able to significantly improve memory and learning in mice dose dependently. Also, the two test drugs were able to significantly decrease the levels of proinflammatory cytokines (Tumor necrosis factor alpha and Interleukin 1-beta) in addition to reducing the extra-cellular deposition of amyloid beta 42 in a dose dependent manner.
- Kassem, I. A. A.,Melek, F. R.,Nabil, Marian,Ragab, Mai F.
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- Two new benzophenone glycosides from the aerial parts of Hypericum przewalskii
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Plants of the genus Hypericum contain various types of secondary metabolites that exhibited extensive biological activities. In the ongoing efforts to discover natural neuroinflammatory inhibitors with the potential to develop into therapeutic agents for neurodegenerative diseases, two new benzophenone glycosides, hyperewalones A and B (1 and 2), along with eight known compounds (3–10), were isolated from the aerial parts of Hypericum przewalskii. Their structures were elucidated by comprehensive analysis of IR, HRESIMS, 1D and 2D NMR spectra, and chemical derivatization. The anti-neuroinflammatory activity of compounds 1–10 was evaluated by determining their ability to inhibit the production of nitric oxide (NO) in lipopolysaccharide (LPS)-activated BV-2 microglial cells. Compounds 2, 4, 6–8 exhibited significant anti-neuroinflammatory activity with IC50 values of 0.61–4.90 μM. These findings suggest that the benzophenone, ionone, and flavonoid glycosides isolated from H. przewalskii are promising anti-neuroinflammatory compounds worthy of further investigations.
- Xie, Jin-Yan,Jin, Qinghao,Gao, Jin-Ming,Zong, Shi-Chun,Yan, Xi-Tao
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supporting information
(2021/01/05)
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- Mechanistic insights on catalytic conversion fructose to furfural on beta zeolite via selective carbon-carbon bond cleavage
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The mechanism for the formation of furfural by dehydration of D-fructose via selective carbon-carbon (C–C) bond cleavage was investigated over beta zeolite (Hβ). Several different pore size zeolites were employed to determine the shape selectivity of fructose isomers. Zeolitic pore sizes that smaller than the kinetic diameter of cyclic fructose also produced yield furfural (~22.5%), while the high yield (66.0%) of hydroxymethylfurfural (HMF) can be achieved over large pore zeolite (USY zeolite), which could accommodate the cyclic fructose. These results indicated that the furfural formation likely began with acyclic fructose. In situ 13C NMR and GC–MS studies, using labeled 13C-1-fructose as substrate, suggested that the conversion of fructose to furfural involved with splitting of the C5-C6 bond. Furthermore, the C1 compound from the cleavage of C–C bond was identified as formaldehyde, inferring that the selective scission of C–C bond was ascribe to the retro-aldol reaction. Interestingly, in situ NMR studies implied that the acyclic fructose mainly derived from pyranose forms. In addition, compared with glucose, fructose directly converted to furfural at the higher yield and reaction rate.
- Wang, Yueqing,Yang, Xiaohai,Zheng, Hongyan,Li, Xianqing,Zhu, Yulei,Li, Yongwang
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p. 130 - 139
(2019/01/03)
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- Cycloartane and oleanane glycosides from the tubers of Eranthis cilicica
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Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1-11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.
- Watanabe, Kazuki,Mimaki, Yoshihiro,Fukaya, Haruhiko,Matsuo, Yukiko
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- Scrobiculosides A and B from the deep-sea sponge Pachastrella scrobiculosa
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Two new steroidal saponins, scrobiculosides A and B, were isolated from the deep-sea sponge Pachastrella scrobiculosa, collected at a depth of 200?m off Miura Peninsula, Japan. The aglycones of scrobiculosides A and B feature a vinylic cyclopropane and a ?24,25 exomethylene on the side chains, respectively. Both saponins have a common sugar moiety composed of β-d-galactopyranosyl-(1 → 2)-6-acetyl-β-d-glucopyranoside, with the exception of an acetyl group on C6″ in scrobiculoside A. Scrobiculoside A exhibited cytotoxicity against HL-60 and P388 cells, with IC50 values of 52 and 61?μM, respectively.
- Jomori, Takahiro,Shiroyama, Shuji,Ise, Yuji,Kohtsuka, Hisanori,Matsuda, Kenichi,Kuranaga, Takefumi,Wakimoto, Toshiyuki
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p. 814 - 819
(2019/05/15)
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- Introducing Oxo-Phenylacetyl (OPAc) as a Protecting Group for Carbohydrates
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A series of oxo-phenylacetyl (OPAc)-protected saccharides, with divergent base sensitivity profiles against benzoyl (Bz) and acetyl (Ac) were synthesized, and KHSO5/AcCl in methanol was identified as an easy, mild, selective, and efficient deprotecting reagent for their removal in the perspective of carbohydrate synthesis. Timely monitoring of AcCl reagent was supportive in both sequential and simultaneous deprotecting of OPAc, Bz, and Ac. The salient feature of our method is the orthogonal stability against different groups, its ease to generate different valuable acceptors using designed monosaccharides, and use of OPAc as a glycosyl donar.
- Kumar, Atul,Gannedi, Veeranjaneyulu,Rather, Suhail A.,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
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p. 4131 - 4138
(2019/04/30)
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- Selective two-step synthesis of 2,5-diformylfuran from monosaccharide, disaccharide, and polysaccharide using H-Beta and octahedral MnO2 molecular sieves
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This study deals with an economical, efficient, and sustainable catalytic process with excellent EcoScore and E-factor values for the selective, two-step synthesis of 2,5-diformylfuran (with a yield higher than 90%) from carbohydrates, especially disaccharide and polysaccharide. This catalytic process involves the abundant and low cost carbohydrate as reactant and economical and sustainable catalysts, H-Beta and octahedral MnO2 molecular sieve. In this two step approach, H-Beta is used in the first step for the conversion of carbohydrate to 5-hydroxymethylfurfural (HMF). Br?nsted acidity of H-Beta catalyzes the hydrolysis and dehydration reactions whereas Lewis acidity catalyzes the isomerization to produce HMF. Thus, H-Beta is suitable for the conversion of various carbohydrate molecules (starch, sucrose, glucose and fructose) to HMF. After the first step, H-Beta is withdrawn and then the reaction mixture is subjected to oxidation catalyst, octahedral MnO2 molecular sieve, in the presence of O2 atmosphere to achieve the high 2,5-diformylfuran (DFF) yield. Molecular oxygen (1 atmosphere, O2 filled balloon) is used as an eco-friendly and economical oxidant. Furthermore, no over oxidation product of DFF is observed. HMF and DFF are recovered from the reaction mixture by the extraction with methyl isobutyl ketone (MIBK) using water and brine solutions. DFF yields of 97.1%, 95.3%, 93.4% and 91.5% are obtained when the reactions are carried out using fructose, sucrose, glucose, and starch, respectively. Stepwise addition of catalysts improves DFF yield (>90%) from fructose, glucose, sucrose, and especially starch. Moreover, the H-Beta and octahedral MnO2 molecular sieve are easily separable and recyclable.
- Sarmah, Bhaskar,Srivastava, Rajendra
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- Pregnane glycosides from the bark of Marsdenia cundurango and their cytotoxic activity
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Seven new pregnane glycosides (1–7) and eight known compounds (8–15) were isolated from the bark of Marsdenia cundurango (Asclepiadaceae). The structures of 1–7 were determined by spectroscopic analysis, including two-dimension NMR spectroscopy, chemical transformations, and chromatographic analysis of the hydrolyzed products. The isolated compounds 1–15 were evaluated for their cytotoxic activity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human lung cells, including apoptosis-inducing activity of a representative pregnane glycoside in HL-60 cells.
- Tatsuno, Satoru,Yokosuka, Akihito,Hatsuma, Fusako,Mashiko, Yuto,Mimaki, Yoshihiro
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- Chemical Constituents from the Roots of Polygala arillata and Their Anti-Inflammatory Activities
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A new compound, named arillatanoside E, which was elucidated as 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1 - 3)-β-D-xylopyranosyl-(1 - 4)-α-L-rhamnopyranosyl-(1 - 2)-(4-O-acetyl)-β-D-fucopyranosyl ester, along with 11 known compounds was isolated from the ethanolic extract of the roots of Polygala arillata. The 11 known compounds were identified as oleanolic acid (2), 3′-E-3,4,5-trimethoxy cinnamoyl-6-benzoyl sucrose (3), trans-ferulic acid (4), trans-feruloyl-glucoside (5), feruloyl-glucoside (6), 2,4,6-trimethoxy-1-O-β-D-glycoside (7), 3-methoxy-4-hydroxybenzoic acid (8), monopentadecanoin (9), sinapic acid (10), p-hydroxybenzaldehyde (11), and palmitic acid (12). Among them, seven isolated compounds 1, 2, 4, 5, 7, 8, and 10 exhibited little cytotoxic activity on macrophage RAW 264.7 cells. Then, the inhibitory effects of 7 isolates on nitric oxide (NO) production in lipopolysaccharide-activated macrophages were evaluated. As a result, 3 compounds have significant anti-inflammatory activity, and they were arillatanoside E (1), oleanolic acid (2), and 2,4,6-trimethoxy-1-O-β-D-glycoside (7).
- Xiang, Wei,Zhang, Guo-Dong,Li, Fang-Yi,Wang, Teng-Long,Suo, Tong-Chuan,Wang, Chun-Hua,Li, Zheng,Zhu, Yan
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- New dammarane-type saponins from gynostemma pentaphyllum
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Six new dammarane-type saponins, gypenosides CP1-6 (1 6), along with 19 known compounds 7 25, were isolated and characterized from the aerial parts of Gynostemma pentaphyllum. Among these compounds, eight dammarane-type saponins, 2, 5, 6, 7, 11, 12, 13, and 15, exhibited the greatest antiproliferative effects against two human tumor cell lines (A549 and HepG2).
- Chen, Po-Yen,Chang, Chih-Chao,Huang, Hui-Chi,Zhang, Li-Jie,Liaw, Chia-Ching,Lin, Yu-Chi,Nguyen, Nham-Linh,Vo, Thanh-Hoa,Cheng, Yung-Yi,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung,Kuo, Yao-Haur
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