- 8-METHOXYKAMPFEROL 3-NEOHESPERIDOSIDE AND OTHER FLAVANOIDS FROM BEE POLLEN OF CRATAEGUS MONOGYNA
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A new flavonol glycoside, 8-methoxykamferol 3-neohesperidoside and 8-methoxykampferol 3-glucosid, 8-methoxykaempferol and kaempferol 3-neohesperidoside were identified from the bee pollen of Crataegus monogyna.
- Dauguet, Jean-Claude,Bert, Maryse,Dolley, Jean,Bekaert, Alain,Lewin, Guy
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- Examination of the phenolic profile and antioxidant activity of the leaves of the australian native plant smilax glyciphylla
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Together with the sweet principle component glycyphyllin A (3), seven phenolic compounds including two new dihydrochalcone rhamnopyranosides, glycyphyllin B (1) and glycyphyllin C (2), and five known flavonoids, catechin (4), kaempferol-3-O-β-d-glucopyranoside (5), quercetin-3-O-β-d- glucopyranoside (6), kaempferol-3-O-β-neohesperidoside (7), and 2R,3R-dihydrokaempferol-3-O-β-d-glucopyranoside (8), have been isolated from the ethanolic extract of the leaves of Smilax glyciphylla for the first time. The structures of these compounds were characterized by spectroscopic methods including UV, MS, and 1D and 2D NMR. In vitro antioxidant capacity tests employing FRAP and DPPH assays indicated that 1, 4, and 6 exhibited potent antioxidant activity and are the key phenolics responsible for the antioxidant activity of the leaf extract of S. glyciphylla.
- Huang, An-Cheng,Wilde, Amelie,Ebmeyer, Johanna,Skouroumounis, George K.,Taylor, Dennis K.
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- Nicotabaflavonoidglycoside, the first example of cembranoid and flavonoid heterodimer from Nicotiana tabacum
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Nicotabaflavonoidglycoside (1), a novel cembrane-type diterpenoid and flavonoid heterodimer had been isolated from the leaves of Nicotiana tabacum. Its structure was elucidated as (1″S, 6″S) or (1″R, 6″R)-8-[6″-((?)-(1″S, 2″E, 4″Z, 7″E, 11″E)-cembra-2″, 4″, 7″, 11″-tetraenyl)]-rutin by comprehensive analyses of the NMR and HRESIMS spectra. Its absolute configurations of C-1″ and C-6″ were assigned as (1″S, 6″S) by its biogenesis and electronic circular dichroism (ECD). A possible biogenesis involving eliminate reaction of (1S, 2E, 4S, 6R, 7E, 11E)-2, 7, 11-cembratriene-4, 6-diol or its 4R isomer, as well as electrophilic substitution reaction of rutin was postulated.
- Yang, Cai-Yan,Lin, Yao,Yuan, Hui-Xiong,Yang, Wen-Pei,Wei, Xian,Huang, Zu-Liang
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- Bignanoside A “A new neolignan glucoside” and bignanoside B “A new iridoid glucoside” from Bignonia binata leaves
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One new neolignan glucoside; bignanoside A (1) and one new iridoid glucoside; bignanoside B (2), and one new lignan rhamnoside; (-)-1yoniresinol 3α-O-α-L-rhamnopyranoside (3) reported for the first time, alongside with seven known compounds were isolated from Bignonia binata leaves. The structures of the isolated compounds were elucidated by various spectroscopic methods, including 1D and 2D NMR experiments, as well as HR-ESI-MS. Compound 2 had a potent DPPH radical scavenging activity with IC50 value of 18.34 ± 0.81 μM. Likewise, compounds 4 and 9 exhibited antitrypanosomal activity with IC50 value of 29.12 ± 1.21 and 17.80 ± 0.32 μM, respectively, against Trypanosoma brucei brucei S427.
- Abdelmohsen, Usama Ramadan,Hajjar, Dina,Hamed, Ashraf Nageeb Elsayed,Kamel, Mohamed Salah,Mahmoud, Basma Khalaf,Matsunami, Katsuyoshi,Samy, Mamdouh Nabil,Sugimoto, Sachiko,Yamano, Yoshi
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- Three new steroidal saponins from Fritillaria pallidiflora
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Three new steroidal saponins, pallidiflosides A (1), B (2), and C (3), have been isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were elucidated as 26-O-β-D-glucopyranosyl-(25R)-furost-5,20(22) -dien-3β,26-diol-3-O-β-D-xylopyranosyl(1 → 4)-[α-L- rhamnopyranosyl(1 → 2)]-β-D-glucopyranoside (1); 26-O-β-D- glucopyranosyl-3β,26-dihydroxyl-20,22-seco-25(R)-furost-5-en-20, 22-dione-3-O-α-L-rhamnopyranosyl(1 → 2)- β-D-glucopyranoside (2); and (25R)-spirost-5-ene-3β,17a-diol-3-O-β-D-glucopyranosyl(1 → 4)- β-D-galactopyranoside (3) by spectroscopic techniques and chemical means.
- Shen, Shuo,Chen, Chao-Jun,Bu, Ren,Ga, Lu,Li, Guo-Yu,Tan, Yong,Li, Xian,Wang, Jin-Hui
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- Phenolic compounds from the whole plants of Gentiana rhodantha (Gentianaceae)
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Gentiana rhodantha Franch. ex Hemsl. (Gentianaceae), an annual herb widely distributed in the southwest of China, has been medicinally used for the treatment of inflammation, cholecystitis, and tuberculosis by the local people of its growing areas. Chemical investigation on the whole plants led to the identification of eight new phenolic compounds, rhodanthenones A-D (1-4, resp.), apigenin 7-O-glucopyranosyl-(1→3)-glucopyranosyl-(1→3)- glucopyranoside (5), 1,2-dihydroxy-4-methoxybenzene 1-O-α-L- rhamnopyranosyl-(1→6)-β-D-glucopyranoside (6), 1,2-dihydroxy-4,6- dimethoxybenzene 1-O-α-L-rhamnopyranosyl-(1→6)-β-D- glucopyranoside (7), and methyl 2-O-β-D-glucopyranosyl-2,4,6- trihydroxybenzoate (8), together with eleven known compounds, 9-19. Their structures were determined on the basis of detailed spectroscopic analyses and chemical methods. Acetylcholinesterase (AChE) inhibition and cytotoxicity tests against five human cancer cell lines showed that only rhodanthenone D (4) and mangiferin (12) exhibited 18.4 and 13.4% of AChE inhibitory effects at a concentration of 10-4 M, respectively, while compounds 1-5 and the known xanthones lancerin (11), mangiferin (12), and neomangiferin (13) displayed no cytotoxicity at a concentration of 40 μM. Copyright
- Xu, Min,Zhang, Ming,Wang, Dong,Yang, Chong-Ren,Zhang, Ying-Jun
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- Two new 23S,26R-hydroxylated spirostanoid saponins from the fruits of Solanum indicum var. recurvatum
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Solanum indicum var. recurvatum, distributed mainly in Hekou, Simao and Menghai areas of Yunnan province, China, is characterized by stellate pubescent leaves with irregular lengths and oblong, short, and downwardly curved anthers. The original species, S. indicum, has been used as an anti-inflammatory, wound-healing agent, an analgesic, and for the treatment of rhinitis, cough, and breast cancer in Chinese folk medicine. The variety was chemically studied for the first time, leading to the isolation of two new rare 23S,26R-hydroxylated spirostanoid saponins, together with five known steroidal components, two of which the rare natural ketosteroids 6-hydroxyandrosta-1,4-diene-3,17-dione and rostadienedione have been isolated from the genus Solanum for the first time. Elucidation of the structures was accomplished by extensive 1D and 2D NMR, UV, and HRESIMS spectroscopic methods.
- Kaunda, Joseph Sakah,Zhang, Ying-Jun
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- A new flavonol glycoside from the aerial parts of Epimedium koreanum Nakai
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A new prenylated flavonol glycoside (1) was isolated from a 95% methanol extract of the dried and powdered aerial parts of Epimedium koreanum Nakai (Herba Epimedii), along with seven previously known flavonoids (2–8). The chemical structure of the new compound (1) was established to be 5-hydroxy-4′-methoxy-8-(2-hydroxy-3-methyl-3-butenyl)flavone 3-O-α-l-rhamnopyranosyl-7-O-β-D-gluco pyranoside on the basis of spectroscopic methods. The antioxidant activities of these compounds were determined by the DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging assay and kaempferitrin (8) showed a high reactivity with DPPH.
- Han, Fubo,Lee, Ik-Soo
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- Steroidal saponins and pregnane glycosides from Smilax microphylla
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Six steroidal saponins and two pregnane glycosides were isolated from the BuOH subfraction of 70% EtOH extract of Smilax microphylla C.H. Wright, among them two were new compounds (1 and 7). Pregnane glycosides were firstly isolated from the genus Smilax
- Lin, Tao,Huang, Hui-Lian,Liu, Rong-Hua,Shu, Ji-Cheng,Ren, Gang,Shao, Feng,Liu, Li-Sha
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- Two new glycosides isolated from Sapindus mukorossi fruits: effects on cell apoptosis and caspase-3 activation in human lung carcinoma cells
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Two new glycosides (1, 2) and two saponins (3, 4) were isolated from the fruits of Sapindus mukorossi Gaertn. The two glycosides were designated as sapindoside G (1) and 4′′,4′′′′′-O-diacetylmukurozioside IIa (2). All four compounds exhibited inhibitory effects against A549 human lung adenocarcinoma cells with inhibition rates up to 69.2–83.3% at a concentration of 100 μg/mL. Flow cytometric analysis revealed that compounds 1–4 could suppress A549 cell growth by promoting cell apoptosis, which was related to the activation of caspase-3.
- Zhang, Xuan-Ming,Yang, De-Po,Xie, Zhi-Yong,Li, Qing,Zhu, Long-Ping,Zhao, Zhi-Min
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- Tareciliosides H-M: Further cycloartane glycosides from leaves of Tarenna gracilipes
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From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Tarenna gracilipes, collected in Okinawa, six further new cycloartane glycosides, named tareciliosides H-M (1-6), were isolated. Their structures were established through a combination of spectroscopic analyses.
- Zhao, Zhimin,Matsunami, Katsuyoshi,Otsuka, Hideaki,Shinzato, Takakazu,Takeda, Yoshio
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- Medicinal flowers. XXII structures of chakasaponins V and VI, chakanoside I, and chakaflavonoside a from flower buds of Chinese tea plant (Camellia sinensis)
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Two acylated oleanane-type triterpene oligoglycosides, chakasaponins V and VI, an aromatic glycoside, chakanoside I, and an acylated flavonol oligoglycoside, chakaflavonoside A, were isolated from the flower buds of Chinese tea plant [Camellia sinensis (L.) O. KUNTZE]. The chemical structures of those new glycosides were elucidated on the basis of chemical and physicochemical evidence.
- Yoshikawa, Masayuki,Sugimoto, Sachiko,Nakamura, Seikou,Matsuda, Hisashi
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- Novel biologically active glycosides from the aerial parts of Cephalaria gazipashensis
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Two new triterpene glycosides, 3-O-β -D-glucopyranosyl-(1→4)- β -D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-( 1→3)-a-L-arabinopyranosyl olean-12-ene 28-O-β -D-glucopyranosyl- (1→6)-β -D-glucopyranosyl ester (gazipashoside A, 1) and 3-O-β -D-glucopyranosyl-(1→4)-β -D-xylopyranosyl-(1→3)-α-L- rhamnopyranosyl-( 1→2)-α-L-arabinopyranosyl hederagenin 28-O-β -D-glucopyranosyl-(1→6)-β -D-glucopyranosyl ester (gazipashoside B, 2), were isolated together with 11 known compounds including 7 triterpene, 1 flavonoid, and 3 iridoidal metabolites from the aerial parts of Cephalaria gazipashensis (Dipsacaceae). The structures of all compounds were elucidated by extensive evaluation of the spectroscopic data (1D- and 2D- NMR, HRESI-MS), as well as chemical examinations. The antimicrobial effects of all pure compounds were tested against gram-positive and gram-negative bacteria. The results indicated that the 2 new triterpene glycosides might be acceptable as antimicrobial active agents.
- Sarikahya, Nazli Boeke,Kirmiziguel, Sueheyla
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- Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities
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Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A?C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A?C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16β-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16β-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A?C, (22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol3-O-β-D-xylopyranosyl-(1→3)-β-D-glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC50 = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC50 value of 37.32 ± 0.793 μM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.
- Kaunda, Joseph Sakah,Qin, Xu-Jie,Zhu, Hong-Tao,Wang, Dong,Yang, Chong-Ren,Zhang, Ying-Jun
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- Molecular networking-based strategy for the discovery of polyacetylated 18-norspirostanol saponins from Trillium tschonoskii maxim.
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Nine undescribed polyacetylated 18-norspirostanol saponins, trilliumosides A?J, were obtained after a guidance based on a molecular networking strategy from the rhizomes of Trillium tschonoskii. Their structures were established by analysis of comprehensive spectroscopic data and chemical methods after their isolation in pure form. All isolated saponins were evaluated for their cytotoxicities against five selected human cancer cell lines (Huh7,A549,MCF-7,HepG2, and MOLT-4) and anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated NO production model in RAW264.7 macrophages. Trilliumoside D showed significant cytotoxicity against MOLT-4 cell lines with an IC50 value of 1.0 ± 0.1 μM, whereas trilliumosides H and I displayed remarkable anti-inflammatory effects on NO production with inhibitory rates of 56.3 ± 1.5 and 56.2 ± 2.2% at the concentration of 1.0 μM, respectively.
- Li, Dan,Liu, Hui,Ni, Wei,Xiao, Wei-Lie,He, Li,Guo, Zhen-Yu,Qin, Xu-Jie,Liu, Hai-Yang
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- Oleanane-and Ursane-Type Triterpene Saponins from Centella asiatica Exhibit Neuroprotective Effects
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Six new pentacyclic triterpenoid saponins, centelloside F (1), centelloside G (2), 11-oxo-asiaticoside B (3), 11-oxo-madecassoside (4), 11(β)-methoxy asiaticoside B (5), and 11(β)-methoxy madecassoside (6), along with seven known ones, asiaticoside (7), asiaticoside B (8), madecassoside (9), centellasaponin A (10), isoasiaticoside (11), scheffoleoside A (12), and centelloside E (13), were separated from the 80% MeOH extract of the whole plant of Centella asiatica, which has been used as a medicinal plant and is now commercially available as a diatery supplement in many countries. Compounds 1 and 2, 3 and 4, and 5 and 6 are three pairs of isomers with oleanane-or ursane-type triterpenes as aglycones. The chemical structures of the new triterpene saponins were fully characterized by extensive analysis of their nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry data. The protective effects of compounds 1-13 on PC12 cells induced by 6-OHDA were screened, and compound 3 displayed the best neuroprotective effect, with 91.75% cell viability at the concentration of 100 μM. Moreover, compound 3 also attenuated cell apoptosis and increased the mRNA expression of antioxidant enzymes, including superoxide dismutase and catalase. Additionally, compound 3 activated the phosphatidylinositol 3-kinase/Akt pathway, including PDK1, Akt, and GSK-3β. These findings suggested that triterpene saponins from C. asiatica were worthy of further biological research to develop new neuroprotective agents.
- Chen, Bin,Hu, Wei-Cheng,Ji, Lilian,Li, Fu,Li, Wei-Bo,Liu, Xin,Wang, Lun,Wang, Ming-Kui,Wu, Zhou-Wei,Zhou, Jing
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- New steroidal saponins from the roots of Solanum melongena L.
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Phytochemical investigation of the roots of Solanum melongena L. resulted in the isolation of six new steroidal saponins, including five new cholestane saponins (1-5) and one new steroidal alkaloid (6), along with one new natural product (7) and three know steroids (8-10). The structures of all isolated compounds were determined by 1D and 2D NMR experiments and by comparison of their spectroscopic and physical data with literature values. The inhibitory activities on nitric oxide (NO) production stimulated by lipopolysaccharide (LPS) in a RAW 264.7 cell line were assayed for all the isolated compounds. Compounds 1, 2 and 4–9 exhibited moderate inhibition of NO production with IC50 values ranging from 12.6 to 59.5 μM.
- Yang, Bing-You,Yin, Xin,Liu, Yan,Zhao, Dong-Ying,Kuang, Hai-Xue
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- Rhamnolipids as Platform Molecules for Production of Potential Anti-zoospore Agrochemicals
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Rhamnolipid biosurfactants have potential applications in the control of zoosporic plant pathogens. However, rhamnolipids have not been closely investigated for the anti-zoospore mechanism or for developing new anti-zoospore chemicals. In this study, RhL-1 and RhL-3 groups of rhamnolipids were used to generate the corresponding RhL-2 and RhL-4 groups and the free diacids. Conversion of RhL-3 to RhL-1 was also accomplished in vitro with cellobiase as the catalyst. The anti-zoospore effects of RhL-1-RhL-4 and the diacids were investigated with zoospores of Phytophthora sojae. For RhL-1-RhL-4, approximately 20, 30, 40, and 40 mg/L, respectively, were found to be the lowest concentrations required to stop movement of all zoospores, which indicates that the anti-zoospore effect remains strong even after RhL-1 and RhL-3 are hydrolyzed into RhL-2 and RhL-4. The free diacids required a significantly higher critical concentration of about 125 mg/L. Rhamnose can be obtained as a co-product.
- Miao, Shida,Dashtbozorg, Soroosh Soltani,Callow, Nicholas V.,Ju, Lu-Kwang
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- Benzyl and phenylethanoid glycosides from the leaves of Magnolia sirindhorniae
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A new benzyl triglycoside, benzyl O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside (1) together with two diastereomer phenylethanoid glycosides, (7R) and (7S)-campneoside I (10, 11) were isolated from the leaves of Magnolia sirindhorniae in addition to 20 known compounds. The structure elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D NMR experiments.
- Srinroch, Chutima,Sahakitpichan, Poolsak,Techasakul, Supanna,Chimnoi, Nitirat,Ruchirawat, Somsak,Kanchanapoom, Tripetch
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- Benzophenone O-glycosides from hypericum elegans
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Elegaphenonoside, a new benzophenone O-rhamnoside, together with two known benzophenone O-glycosides, namely hypericophenonoside and neoannulatophenonoside, were isolated from the aerial parts of Hypericum elegans Stephan ex Willd. The structure of the ne
- Nedialkov, Paraskev T.,Zheleva-Dimitrova, Dimitrina,Girreser, Ulrich,Kitanov, Gerassim M.
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- Neuroprotective effects of triterpenoid saponins from Medicago sativa L. against H2O2-induced oxidative stress in SH-SY5Y cells
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Medicago sativa L. is a forage legume plant widely distributed in all continents. Six new triterpenoid saponins, Medicagosides A-F (1–6) and five known ones (7–11) were isolated from M. sativa. Their structures were determined via HRESIMS, 1D and 2D NMR analysis. Biologically, all the isolates displayed neuroprotective activities against H2O2-induced damage in SH-SY5Y cells. Among them, compounds 1, 3–5 and 10 exhibited striking neuroprotective activities at 100 μM, restoring cell viability range from 79.66% to 89.03%, relative to 79.46% (100 μM) of Trolox used as the positive control.
- Liu, Xue-Gui,Sun, Yu-Qiu,Bian, Jun,Han, Ting,Yue, Dan-Dan,Li, Dan-Qi,Gao, Pin-Yi
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- Structural characterization and in vitro antitumor activity of A polysaccharide from Artemisia annua L. (Huang Huahao)
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One water-soluble polysaccharide (AAP), with a molecular weight of 6.3 × 104 Da, was isolated from Artemisia annua L. Structrual analysis indicated that AAP was found to be a 1, 3-α-linked and 1, 3, 6-α-linked Glcp backbone, with a branch of 1, 6-α-linked Glcp and terminal 1-linked-L-Rhap along the main chain in a ratio of 1: 1: 1: 1. MTT assay showed that AAP reduced the cell viability of HepG2 cells in a concentration-dependent manner. DAPI staining and Flow cytometric analysis revealed that AAP suppressed cells proliferation, not most at least via inducing p65-dependent mitochondrial signaling pathway, as evidenced by more activation of caspase-3 and -9, down-regulation of Bcl-2 protein, up-regulation of Bax protein and release of cytochrome c from mitochondria into cytosol, as well as suppression of the nuclear factor-κB (NF-κB) p65. These data confirmed AAP inhibits HepG2 cell growth via inducing caspase-dependent mitochondrial apoptosis and inhibition of NF-κB p65.
- Yan, Liang,Xiong, Chuan,Xu, Pan,Zhu, Jing,Yang, Zhirong,Ren, Hong,Luo, Qiang
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- Cytotoxic Steroidal Glycosides from the Whole Plant of Calamus acanthophyllus
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A new steroidal glycoside, callaphylloside (1), together with seven known glycosides (2-8), was isolated from the whole plant of Calamus acanthophyllus. The structure of the new compound was elucidated by spectral data analyses and chemical transformations. Compounds 5 and 8 exhibited strong cytotoxic activity against four cancer cell lines (0.7 ≤ IC50 ≤ 3.4 μM). Evaluation of the structure-activity relationship among steroidal glycosides revealed that the structure of spirostanol with an α-L-rhamnopyranosyl linked to C-2 of the inner glucopyranosyl residue both play a critical role in the effects of these compounds on the cancer cell lines.
- Prawat, Hunsa,Mahidol, Chulabhorn,Kaweetripob, Wirongrong,Intachote, Pakamas,Pisutjaroenpong, Somchai,Ruchirawat, Somsak
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- Steroidal saponins from Chlorophytum orchidastrum
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Six new spirostane-type saponins (1-6), named orchidastrosides A-F, and chloromaloside D were isolated from an ethanol extract of the roots of Chlorophytum orchidastrum. The saponins have neotigogenin or neogitogenin as the aglycon and oligosaccharidic chains possessing seven to nine sugar units. Their structures were elucidated mainly by 2D NMR spectroscopic analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and FABMS and HRESIMS. Compounds 1-6 were tested for cytotoxicity against two human colon cancer cell lines, HCT 116 and HT-29.
- Acharya, Debabrata,Mitaine-Offer, Anne-Claire,Kaushik, Nutan,Miyamoto, Tomofumi,Paululat, Thomas,Mirjolet, Jean-Francois,Duchamp, Olivier,Lacaille-Dubois, Marie-Aleth
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- Two new rhamnopyranosides of neolignans from Sanguisorba officinalis
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Two new rhamnopyranosides of neolignans, (7S,8R)-4,9,5,9-tetrahydroxy-3,3- dimethoxy-8-O-4-neolignan-7-O-l-rhamnopyranoside (1) and (7S,8R)-4,9,9- trihydroxy-3,3,5-trimethoxy-8-O-4-neolignan-7-O-l-rhamnopyranoside (2), together with a known compound (7S,8R)-4,7,9,9-tetrahydroxy-3,3-dimethoxy-8-O-4- neolignan (3), were isolated from the 80% EtOH extract of the roots of Sanguisorba officinalis. Their structures were characterized by spectroscopic analysis including 1D NMR, 2D NMR, and HR-ESI-MS, and chemical method.
- Hu, Jiang,Shi, Xiao-Dong,Chen, Jian-Gang,Li, Chang-Sheng
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- Montbresides A–D: antibacterial p-coumaroyl esters of a new sucrose-based tetrasaccharide from Crocosmia × crocosmiiflora (montbretia) flowers
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Crocosmia × crocosmiiflora (montbretia) flowers yielded four esters (montbresides A–D) of a new sucrose-based tetrasaccharide, 3-O-β-D-glucopyranosyl-4′-O-α-D-rhamnopyranosyl-sucrose [β-D-Glc-(1 → 3)-α-D-Glc-(1?2)-β-D-Fru-(4 ← 1)-α-D-Rha]. All four possess O-p-coumaroyl residues on C-3 of fructose and C-4 of α-glucose, plus O-acetyl residues on C-2 and C-3 of rhamnose and C-6 of fructose. Montbresides A and B are additionally O-acetylated on C-1 of fructose. The p-coumaroyls are trans- in montbresides A and C and cis- in B and D. Elemental compositions were determined from MS data, and structures from 1D and 2D NMR spectra. Monosaccharide residues were identified from selective 1D TOCSY spectra and TLC, and acylation sites from 2D HMBC spectra. Enantiomers were distinguished by enzymic digestion. Montbretia flower extracts were cytotoxic against six human cancerous cell-lines, but purified montbresides lacked cytotoxicity. Each montbreside displayed antibacterial activity against Staphylococcus aureus (minimal inhibitory concentration ~6 μg/ml). Montbretia is a potential source of new cytotoxins and antibacterial agents.
- Perveen, Shagufta,Sadler, Ian H.,Orfali, Raha,Al-Taweel, Areej Mohammad,Murray, Lorna,Fry, Stephen C.
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- Triterpene saponins from clematis mandshurica and their antiproliferative activity
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Six new triterpene saponins, clematomandshurica saponins F-K (1-6), together with a known compound (7), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis. Compounds 5-7 exhibited antiproliferative effects against PC-3 human prostate cancer cells with GI50 values of 1.29, 1.50, and 0.71 M, respectively.
- Gong, Yi-Xia,Hua, Hui-Ming,Xu, Yong-Nan,Liu, Jian-Yu,Yu, Zong-Gui,Ma, Jing,Zhang, Hui,Jing, Yong-Kui
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- Three new acylphloroglucinol glucosides from the roots of Lysidice rhodostegia and their antioxidant activities
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Three new acylphloroglucinol glucosides, rhodosides A-C (1–3), and three known ones (4–6) were isolated from the roots of Lysidice rhodostegia. The new structures were identified by MS, NMR, and acid hydrolysis. In addition, the antioxidant capacities of the isolated compounds were evaluated using DPPH radical-scavenging assay, and compounds 1–6 exhibited obvious antioxidant activities with IC50 values of 24.65 ± 1.27 to 38.11 ± 1.35 μM.
- Li, Yaolan,Li, Yingying,Wang, Guocai,Wu, Chun,Xu, Yaping,Yi, Xue,Zhang, Yubo
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- New prenylflavonol glycosides with xanthine oxidase inhibitory activity from the leaves of Cyclocarya paliurus
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Eight new prenylflavonol glycosides (1–8), along with five known analogues (9–13) were isolated from the n-butanol extract of the dried leaves of Cyclocarya paliurus (family Juglandaceae) for the first time. The structures of these compounds were characte
- Chang, Xi-Wen,Chen, Zu-Hui,He, Xiao-Ai,Li, Jing,Lv, Wen-Yan,Sun, Hui-Hui,Tan, Jie,Wang, Wen-Xuan,Wu, Jian-Ping,Xu, Kang-Ping,Ye, Zi-Jun,Zhu, Gang-Zhi,Zhu, Hui
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- A new flavonoid glycoside from Galium verum
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A new flavonoid glycoside, an apigenin 7-O-(3,4-di-O-acetyl)-α-L- rhamnopyranosyl-(1∈→∈-6)-β-D- glucopyranoside (1), was isolated from the 95% ethanol extract of Galium verum L. Its structure was elucidated by spectroscopic analysis.
- Zhao, Chun-Chao,Shao, Jian-Hua,Zhao, Chun-Jie,Li, Xian
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- Two new glycosides from the fruits of Forsythia suspense
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Two new glycosides suspensaside C (1) and 2,3,5,6-tetrahydro-jacaranone-4- O-β-d-glucopyranoside (2), together with four known compounds suspensaside A (3), rengynic acid-1′-O-β-d-glucopyranoside (4), forsythoside A (5), and rengynic acid (6), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HR-ESI-MS. All isolates were tested for their cytotoxicities against five human cancer cell lines (A549, Colo-205, Hep-3B, HL60, and KB). Compound 3 exhibited cytotoxicity against HL-60, Hep-3B, and A549 cancer cell lines.
- Yan, Xin-Jia,Bai, Xin-Yu,Liu, Qing-Bo,Liu, Shen,Gao, Pin-Yi,Li, Ling-Zhi,Song, Shao-Jiang
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- Antimicrobial triterpenoid glycosides from Cephalaria scoparia
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Five new oleanane-type triterpenoid glycosides (1-5), named scoposides A-E, along with one known bisdesmosidic triterpene glycoside, were isolated from the aerial parts of Cephalaria scoparia. Three prosapogenins (2a-4a) were also obtained after alkaline hydrolysis of the bisdesmosidic compounds 2-4. The structures of compounds 1-5 were determined by spectroscopic (1D and 2D NMR, HRESIMS) and chemical methods. The antimicrobial effects of compounds 1-5 were evaluated against a small panel of Gram-positive and Gram-negative bacteria.
- Sarikahya, Nazli Boeke,Kirmiziguel, Sueheyla
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- Flavonol glycosides from muehlenbeckia platyclada and their anti-inflammatory activity
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A new flavonol, morin-3-O-α-rhamnopyranoside (1), along with four known flavonols, kaempferol 3-O-α-rhamnopyranoside (2), kaempferol 3-O-β-glucopyranoside (3), quercetin 3-O-α-rhamnopyranoside (4) and (+)-catechin (5), were isolated from the methanolic ex
- Yen, Chiao-Ting,Hsieh, Pei-Wen,Hwang, Tsong-Long,Lan, Yu-Hsuan,Chang, Fang-Rong,Yang-Chang
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- Lanostane triterpene glycosides from the flowers of Lyonia ovalifolia var. hebecarpa and their antiproliferative activities
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Sixteen lanostane-type triterpene glycosides including eight new ones, named lyonicarposides A–H (1–8), were isolated from the flowers of Lyonia ovalifolia var. hebecarpa (Franch. ex F.B. Forbes & Hemsl.) Chun (Ericaceae). The chemical structures of the new compounds were elucidated by the comprehensive spectroscopic techniques and chemical methods. The Mo2(OAc)4–induced electronic circular dichroism method was used to determine the absolute configurations of C-24 in lyonicarposides A (1), C (3), and E (5). This is the first phytochemical study on the flowers of L. ovalifolia var. hebecarpa. All the isolates were evaluated for their antiproliferative activities against SMMC-7721, HL-60, SW480, MCF-7, and A-549 cell lines. Lyonicarposides A (1) and B (2) showed moderate antiproliferative activities against five cancer cell lines with IC50 values ranging from 12.39 to 28.71 μM. Lyonicarposides C (3) and G (7) and lyonifoloside M (12) selectively inhibited the proliferation of HL-60 and MCF-7 cell lines with IC50 values ranging from 13.03 to 17.71 μM. Interestingly, lyonifoloside L (13) selectively inhibited the proliferation of MCF-7 cell line with an IC50 value of 16.27 μM. Their structure-activity-relationships were discussed.
- Li, Shunyi,Liu, Junjun,Peng, Xiang,Teng, Yang,Yao, Guangmin,Zhang, Hanqi,Zheng, Xiaofeng,Zou, Congming
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- Two novel furostanol saponins from the tubers of Ophiopogon japonicus
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Phytochemical investigation of the fresh tubers of Ophiopogon japonicus led to the isolation of two new furostanol saponins (1 and 2) together with two known steroidal saponins (3 and 4). Comprehensive spectroscopic analysis allowed the chemical structure
- Guo, Yu,Liu, Yi-Xun,Kang, Li-Ping,Zhang, Tao,Yu, He-Shui,Zhao, Yang,Xiong, Cheng-Qi,Ma, Bai-Ping
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- New steroidal saponins with cytotoxic activities from Smilax trinervula
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Three new steroidal saponins, namely, trinervulosides A-C (1-3), were isolated from the rhizomes and roots of Smilax trinervula, together with four known compounds, 4-7. Their structures were determined through chemical evidence, NMR spectroscopy, mass spectrometry and comparison with the literature. Compounds 1-7 were assayed for cytotoxic activities, and only trinervuloside B (2) showed activity against SGC-7901 and HCT-116 cell lines.
- Liang, Fang,He, Jun-Wei,Zhu, Gen-Hua,Liu, Rong-Hua,Shu, Ji-Cheng,Shao, Feng,Huang, Hui-Lian
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- Polyhydroxylated spirostanol saponins from the tubers of Dioscorea polygonoides
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Three new polyhydroxylated spirostanol saponins (1-3) were isolated from the tubers of Dioscorea polygonoides. The structures of these new compounds were determined on the basis of extensive spectroscopic analysis and the results of acid or enzymatic hydrolysis as (23S,24R,25S)-23,24-dihydroxyspirost-5-en- 3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (1), (23S,25R)-12α,17α,23-trihydroxyspirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (2), and (23S,25R)-14α,17α,23-trihydroxyspirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3), respectively.
- Osorio, Jaime Nino,Martinez, Oscar M. Mosquera,Navarro, Yaned M. Correa,Watanabe, Kazuki,Sakagami, Hiroshi,Mimaki, Yoshihiro
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- New minor spirostane glycosides from Ypsilandra thibetica
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A further phytochemical investigation on the whole plants of Ypsilandra thibetica yielded three new spirostane glycosides, named ypsilandrosides M-O (1-3). Their structures were established as (3β,11α,25R)-3,11- dihydroxyspirost-5-en-12-one 3-{O-α-L-rhanmopyranosyl-(1→4)-O-L- rhanmopyranosyl-(1→4)-O-[α-L-rhanmopyranosyl-(1→2)] -β-D-glucopyranoside} (1), (3β,7β,25R)-spirost-5-ene-3,7-diol 3-{O-α-L-rhanmopyranosyl-(1→4)-O-α-L-rhanmopyranosyl-(1→4) -O-[α-L-rhanmopyranosyl-(1→2)]-β-D-glucopyranoside} (2), and (3β,7α,25R)-spirost-5-ene-3,7,17-triol 3-{O-α-L- rhanmopyranosyl-(1→4)-O-α-L-rhanmopyranosyl-(1→4) -O-[α-L-rhanmopyranosyl-(1→2)]-β-D-glucopyranoside} (3) by means of a combination of MS, 1D- and 2D-NMR spectroscopic methods, and chemical degradation. Among them, compound 3 is the first pennogenin (=(3β,25R)- spirost-5-ene-3,17-diol) saponin whose aglycone contains an OH group at C(7). Compounds 1-3 were evaluated for the inhibition of the growth of five tumor cell lines, but all of them proved to be inactive. Copyright
- Zhang, Xu-Dong,Chen, Chang-Xiang,Yang, Jun-Yun,Ni, Wei,Liu, Hai-Yang
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- Anti-inflammatory lignans and phenylethanoid glycosides from the root of Isodon ternifolius (D.Don) Kud?
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Five undescribed lignans, three undescribed phenylethanoid glycosides and eight known compounds were isolated from the root of Isodon ternifolius (D.Don) Kud? (Lamiaceae). The structures of all of the isolated constituents were characterized by physical data analyses including NMR, MS and ECD. The anti-inflammatory activities of the isolates were evaluated based on their ability to inhibit NO, PGE2 and TNF-α production in LPS-induced RAW 264.7 macrophage cells. Six phenyl-naphthalene lignans, ternifoliuslignan A, ternifoliuslignan B, ternifoliuslignan C, ternifoliuslignan D, ternifoliuslignan E and 3-carboxy-6,7-dihydroxy-1-(3′,4′-dihydroxyphenyl) -naphthalene, can substantially inhibit the release of NO with IC50 values in the range of 9.98–29.14 μM, which are better than the positive reference. These phenyl-naphthalene lignans could markedly decrease the secretions of PGE2 and TNF-α in LPS-induced RAW264.7 cells. Ternifoliuslignan C and ternifoliuslignan D decreased iNOS, COX-2 and NF-κB/p65 protein expression. A preliminary structure-activity relationship among the phenyl-naphthalene lignans for the anti-inflammatory activity was discussed.
- Zhang, Yanjun,Wang, Ke,Chen, Huangcan,He, Ruijie,Cai, Runlin,Li, Jian,Zhou, Dexiong,Liu, Wei,Huang, Xishan,Yang, Ruiyun,Deng, Shengping,Li, Jun,Guan, Xinlan
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- Chemical composition and antioxidant activity of aerial parts of Ferula longipes Coss. ex Bonnier and Maury
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This is the first study on the phytochemistry and antioxidant activity of Ferula longipes Coss. ex Bonnier and Maury (Apiaceae). A new flavonoid quercetin-3-O-α-L-rhamnopyranoside-7-O-?-D-[2-O-caffeoyl]-glucopyranoside (1), along with 10 known compounds kaempferol-3-O-α-L-rhamnopyranoside (2), quercetin-3-O-α-L-rhamnopyranoside (3), kaempferol-3-O-?-D-glucopyranoside-7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-α-L-rhamnopyranoside-7-O-?-D-glucopyranoside (5), quercetin-3-O-α-L-rhamnopyranoside-7-O-?-D-glucopyranoside (6), isorhamnetin-3,7-di-O-β-D-glucopyranoside (7), apigenin (8), apigenin-7-O-?-D-glucopyranoside (9), 3,5-dicaffeoylquinic acid (10), deltoin (11) were isolated from the aerial parts of Ferula longipes Coss. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The compounds 1, 3, 4, 6, 7 and 10 were evaluated for their antioxidant activity, compound 1 exhibited the best antiradical activity potential and showed IC50 and A0.5 values 5.70, 7.25, 5.00, and 2.63?μg/mL towards DPPH free radical-scavenging, ABTS, CUPRAC, and reducing power assays, respectively compared with BHA, BHT and ascorbic acid which were used as positive controls.
- Bouratoua, Aicha,Khalfallah, Assia,Bensouici, Chawki,Kabouche, Zahia,Alabdul Magid, Abdulmagid,Harakat, Dominique,Voutquenne-Nazabadioko, Laurence,Kabouche, Ahmed
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- A new flavonol glycoside and biological activities of Adenanthera pavonina L. leaves
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Adenanthera pavonina is a plant belonging to family Fabaceae. The 95% ethanol extract (EtOH) of the dried powdered leaves of the plant and successive extracts with solvents of increasing polarities were prepared. Fractionation of the successive aqueous EtOH extract on polyamide column and purification of the isolated compounds on Sephadex LH20 led to the isolation of a new methoxy flavonol glycoside named as quercetin 3-O-α-dirhamnopyranosyl-(1? → 2″,1″″ → 6″)-β-glucopyranoside- 4′-methoxy (1), as well as kaempferol-3-O-α-dirhamnopyranosyl- (1? → 2″,1″″ → 6″)-β- glucopyranoside (2), isovitexin (3), quercetin-3-O-rhamnopyranosyl(1? → 4″)-β-glucopyranoside (4), quercetin-3-O-β- glucopranoside-4′-O-rhamnopyranoside (5), kaempferol-3-O-α- rhamnopyranosyl(1? → 2″)-β-glucopyranoside (6), quercetin-3-O-rhamnopyranosyl(1? → 2″)-β-glucopyranoside (7), quercetin-3-O-β-glucopyranoside (8), kaempferol (9) and quercetin (10). Structures of the isolated compounds were established by spectroscopic analysis. Antioxidant activities of EtOH extract, successive extracts and compounds 1 and 2 were evaluated. The ethyl acetate (EtOAc) extract and EtOH extract showed 62.67% and 49.30% free radical scavenging activity, respectively. Cytotoxic activities of the EtOH extract and compounds (1) and (2) were evaluated. The EtOH extract showed a significant cytotoxic activity against Hep G-2 (IC50 = 2.50 μg) as compared with cisplatin (IC 50>10 μg). 2014
- Mohammed,Zeid, A.H. Abou,El-Kashoury,Sleem,Waly
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- A new flavonol glycoside from kalanchoe pinnata leaves
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A new flavonol glycoside i.e., 7-O-methylkaempferol-3-O-α-L-rhamno- pyranosyl-(16)-O-b-D-galactopyranoside (1) together with a known flavonol glycoside; kaempferol-14-O-α-L-rhamnopyranosyl-(13)-O-α-L- rhamnopyranosyl-(16)-O-β-D-galactopyranoside (2) were isolated from methanolic fraction of leaves of Kalanchoe pinnata. Their structures were determined with the help of chemical method and concerted use of 1D and 2D NMR spectroscopy.
- Bodakhe, Kiran S.,Namdeo, Kamta P.,Bodakhe, Surendra H.,Pandey, Devi P.
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- New anthraquinone and iridoid glycosides from the stems of Hedyotis hedyotidea
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Five new anthraquinone glycosides, hedanthrosides A-E (1-5, resp.) and two new iridoid glycosides, hediridosides A and B (6 and 7, resp.), along with two known anthraquinones and four known iridoids, were isolated from the stems of Hedyotis hedyotidea (DC.) Merr. The structures of the new compounds were elucidated on the basis of 1D- and 2D-NMR, and HR-MS analysis and chemical methods. Copyright
- Hu, Xiao-Ping,Zhang, Shu-Wei,Liu, Shan-Shan,Xuan, Li-Jiang
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- Spirostanol tetraglycosides from Ypsilandra thibetica
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Phytochemical reinvestigation on the whole plants of Ypsilandra thibetica obtained five new spirostane glycosides, ypsilandrosides H-L (1-5), and a known saponin polyphylloside III (6). Among them, 1 and 2 are the first spirostane glycosides which possess novel 5(6 → 7) abeo-steroidal aglycones. Compounds 3 and 4 are rare saponins whose aglycones contain a hydroxyl group at C-7. Their structures were elucidated on the basis of MS, 1D and 2D NMR spectroscopic analysis and chemical evidences. The isolated compounds were evaluated for their cytotoxic activity on five tumor cell lines.
- Lu, Yi,Chen, Chang-Xiang,Ni, Wei,Hua, Yan,Liu, Hai-Yang
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- Antioxidant activity of phenolic and phenylethanoid glycosides from Teucrium polium L
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In the present study, the chemical composition and antioxidant activities of Teucrium polium L. (Lamiaceae) were assessed. Fractionation of methanol extract obtained from the aerial parts of T. polium yielded one new phenylethanoid glycoside, named poliumoside B, together with four known flavonoids, two iridoid glycosides and a known poliumoside. The structures of all of these compounds were elucidated on the basis of spectroscopic data from 1D and 2D NMR experiments and MS spectral analyses. The antioxidant activities of the crude extracts and of the isolated compounds were evaluated through tests such as DPPH radical-scavenging capability, reducing power, xanthine oxidase inhibitory effect and inhibition of linoleic acid peroxidation. The highest antioxidant activity was found in the n-butanol extract, which also contained active polyphenols, thus suggesting that this plant could be used as a source of natural molecules, to provide safe antioxidant additives and nutraceuticals. The structure-activity relationships of the isolated compounds are also discussed.
- De Marino, Simona,Festa, Carmen,Zollo, Franco,Incollingo, Filomena,Raimo, Gennaro,Evangelista, Giovanna,Iorizzi, Maria
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- Two new triterpenoid saponins from Centella asiatica
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Two undescribed ursane-type triterpene saponins, named asiaticoside H (1) and I (2), were isolated from the whole plants of Centella asiatica. The chemical structures of 1 and 2 were mainly characterized by extensive analysis of their 1D and 2D NMR and HR
- Ren, Bo,Luo, Wei,Xie, Meng-jun,Zhang, Mei
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- Forsythoneosides A-D, Neuroprotective Phenethanoid and Flavone Glycoside Heterodimers from the Fruits of Forsythia suspensa
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Forsythoneosides A-D (1-4), four unusual adducts of a flavonoid unit fused to a phenylethanoid glycoside through a pyran ring or carbon-carbon bond, and four new phenylethanoid glycosides (5-8) were isolated from the fruits of Forsythia suspensa, together with nine known compounds. The structures of 1-8, including their absolute configurations, were elucidated by spectroscopic data as well as experimental and calculated electronic circular dichroism analysis. Compounds 2 and 4 inhibited PC12 cell damage induced by rotenone, and increased cell viability from 53.9 ± 7.1% to 70.1 ± 4.0% and 67.9 ± 5.2% at 0.1 μM, respectively.
- Zhang, Fan,Yang, Ya-Nan,Song, Xiu-Yun,Shao, Si-Yuan,Feng, Zi-Ming,Jiang, Jian-Shuang,Li, Li,Chen, Nai-Hong,Zhang, Pei-Cheng
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- Xanthosaponins A and B, two unusual steroidal saponins with an unprecedented 16,17-: Seco -cholestane skeleton from Solanum xanthocarpum and their cytotoxic activities
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Xanthosaponins A (1) and B (2), two unusual steroidal saponins with a new 16,17-seco-cholestane carbon skeleton were isolated from the fruits of Solanum xanthocarpum. The structures of all isolated compounds were determined using 1D and 2D NMR experiments and MS analyses. Xanthosaponin A (1) exhibited significant cytotoxic activity against MGC803, LN229, and SMMC7721 cells. This journal is
- Jiang, Peng,Jiang, Yi-Kai,Kuang, Hai-Xue,Li, Xiao-Mao,Liu, Yan,Pan, Juan,Wang, Si-Yi,Xu, Zhen-Peng,Yang, Bing-You
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p. 1815 - 1820
(2022/01/31)
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- Parisvaniosides A–E, five new steroidal saponins from Paris vaniotii
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The species of Paris genus is a prolific source of structurally diverse steroidal saponins responsible for multivarious biological properties. The first phytochemical investigation on the steroidal saponin constituents from the rhizomes of Paris vaniotii Lévl. led to the discovery and structural characterization of four new spirostanol saponins, named parisvaniosides A-D (1–4), and one new furostanol glycoside, named parisvanioside E (5), along with eleven known analogues (6–16). Their structures were unambiguously established on the basis of extensive spectroscopic analysis and comparison with the reported spectroscopic data. Compound 1 is a rare spirostanol saponin sharing with a C-9/C-11 double bond and a peroxy group located between C-5 and C-8 of the aglycone, whereas 3 and 4 are unusual C-27 steroidal sapoins with hydroxyl/methoxyl at both C-5 and C-6. Furthermore, 5 is the first furostanol saponin with a unique aglycone featuring two trisubstituted double bonds in ring B. All isolated saponins were evaluated for their anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW 264.7 macrophages.
- Ji, Yun-Heng,Liu, Hai-Yang,Ni, Wei,Xiao, Long-Gao,Yan, Huan,Yu, Ling-Ling
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- Structural characterization of phenolic constituents from the rhizome of Imperata cylindrica var. major and their anti-inflammatory activity
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As one of raw materials, the rhizome of Imperata cylindrica var. major (Nees) C.E. Hubb. is used in kinds of preparations curing inflammation related diseases, while its effective substances are not yet clear. In this paper, its chemical constituents and their anti-inflammatory activities were investigated. As results, ten compounds, named as imperphenoside A (1), imperphenols B (2) and C (3), imperphenosides D–F (4–6), and imperlignanosides A–D (7–10), along with previously reported thirty-seven known ones (11–47) were obtained from it. Their structures were ascertained basing on the extensive spectroscopic methods and electronic circular dichroism data analysis. Meanwhile, compounds 4, 11, 12, 24, 27, 31, 32, 37, 43, 45, and 47 exhibited nitric oxide inhibitory effects in concentration dependent at 3, 10, and 30 μM on lipopolysaccharides induced RAW 264.7 cells. Moreover, the western blot analysis indicated that compounds 4, 11, 43, and 47 could restrain the phosphorylation of nuclear factor kappa-B kinase to down-regulate the protein expression of inflammatory cytokines such as inducible nitric oxide synthase, interleukin-6 and tumor necrosis factor-α. In conclusion, they might play the anti-inflammatory effects through regulating NF-κB signaling pathway.
- Cao, Hui-Na,Han, Yu,Hao, Mi-Mi,Jiang, Hong-Yu,Li, Hui-Min,Ruan, Jing-Ya,Wang, Tao,Zhang, Yi,Zhang, Ying,Zhao, Wei
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- Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions
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Sargassum fusiforme polysaccharides (SFPs), including SFP-3-40, SFP-3-60, SFP-3-80, SFP-7-40, SFP-7-60, SFP-7-80, SFP-10-40, SFP-10-60, and SFP-10-80, were extracted at different pH (3, 7, and 10), and then precipitated with graded precipitation of 40%, 60% and 80% (v/v) ethanol solution, respectively. Their physicochemical properties and α-glucosidase inhibitory activity were determined. Results showed that SFPs significantly differed in the contents of total sugar, protein, uronic acid, sulfate, the zeta potential, and molecular weight distribution. SFPs, including SFP-10-40, SFP-10-60, and SFP-10-80, had bigger absolute zeta potential value and higher respective average molecular weight in the same ethanol concentration precipitate. All samples were mainly composed of fucose, glucuronic acid, and mannose with different molar ratios. The extraction pH and precipitation ethanol solution concentration caused little changes in functional groups, but significantly altered surface morphology of SFPs. Congo red test revealed that all polysaccharides were not helical polysaccharides. Rheological measurements indicated that SFPs were pseudoplastic fluids and showed elastic behavior of the gel. Except SFP-3-40 and SFP-3-60, all other samples had a stronger α-glucosidase inhibitory activity than that of acarbose. The inhibition type of SFPs against α-glucosidase varied owing to different extraction pH and precipitation ethyl concentration. This study shows that extraction pH can significantly affect the structure and hypoglycemic activity of SFPs and provide a data support for the scientific use of Sargassum fusiforme in industrial production.
- Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen
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p. 602 - 610
(2021/11/30)
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- Chemical Components in Hedera rhombea Leaves and Their Cytotoxicity
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Two novel triterpene glycosides (1 and 2), 17 known triterpene glycosides (3-19), two known flavonoid glycosides (20 and 21), and two known norsesquiterpene glucosides (22 and 23) were isolated from Hedera rhombea (Araliaceae) leaves. The structures of 1
- Mimaki, Yoshihiro,Miyake, Katsunori,Oguro, Airi,Shimomura, Tatsuya,Yokogawa, Shohei,Yokosuka, Akihito
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p. 175 - 181
(2022/02/05)
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- Two new steroidal alkaloids from the mature fruits of Solanum nigrum
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Two previously undescribed steroidal alkaloids, compounds 1–2, were isolated from the ripe fruits of Solanum nigrum, along with seven known metabolites (3–9). Based on spectroscopic and chemical evidence, including IR, NMR, and HR-ESI-MS analyses, the structures of the isolated compounds were elucidated as 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)]-β-D-galacopyranoside and 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside. Four steroidal alkaloids (compounds 1–2 and 4–5) were tested for their anti-proliferative effects against the HT-29, A549, and Lewis cell lines. Both of the previously isolated compounds inhibited the proliferation of these three cell lines in a dose-dependent manner, with the most significant effect being in the A549 cells, but neither reached IC50 at 50 μM. These results revealed that S. nigrum had weak cytotoxicity, indicating its clinical safety as a traditional anti-tumor herbal medicine.
- Lin, Li,Liu, LiangYu,Wang, JianNong,Wang, WenYi,Wu, Tong,Yang, YuKe
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- Undescribed C -Glycosylflavones from Corn Silk and Potential Anti-inflammatory Activity Evaluation of Isolates #
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Phytochemical investigation of corn silk resulted in isolation and characterization of four flavone C-glycosides, chrysoeriol 6- C - β -oliopyranosyl-7- O - β -D-glucopyranoside (1), 3′-methoxycassiaoccidentalin A (2), chrysoeriol 6- C - β -boivinopyranosyl-7- O - β -D-glucopyranoside (3), and ax-4″-OH-3′-methoxymaysin (4), a triterpenoid, friedelin (5), two sterols, (22 E)-5 α,8 α -epidioxyergosta-6,22-dien-3 β -ol (6) and 6 β -hydroxystigmasta-4,22-diene-3-one (7), and a mixture of β -sitosterol and stigmasterol. Compounds 1 and 2 were previously undescribed. Structure elucidation of the isolated compounds was attained using spectral data including 1D and 2D NMR and HRESIMS. Compounds 1, 2, 5, and 6 inhibited iNOS activity in LPS-induced macrophages and decreased nitrite levels by 68.64 ± 4.46, 65.67 ± 6.47, 88.50 ± 0.50, and 94.00 ± 4.00%, respectively, at 50 μM. Compound 5 also showed inhibition of NF- κ B (51.00 ± 1.50%). Compounds 1 and 2 induced NAG-1 activity in chondrocytes by 1.80 ± 0.05 and 2.00 ± 0.13 fold, respectively. The extract of corn silk, however, did not exhibit inhibition of iNOS or NF- κ B but induced NAG-1 by 1.80 ± 0.51 fold.
- Ali, Zulfiqar,Khan, Ikhlas A.,Khan, Shabana I.,Radhakrishnan, Srivedavyasasri,Sarfare, Satish,Zulfiqar, Fazila
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- A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
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The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.
- Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
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- A new anti-inflammatory lignan from Lonicerae Japonicae flos
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One new lignan, loniceralanside A (1), together with three known compounds (2–4), were purified from Lonicerae Japonicae Flos. Their structures were determined by HR-ESI-MS, 1 D and 2 D NMR data. Compounds 2–4 were separated from the plant for the first time. The biological test showed that compound 1 had significant anti-inflammatory activity with inhibiting the release of β-glucuronidase induced by platelet-activating factor (PAF) in rat polymorphonuclear leukocytes (PMNs) (IC50 = 3.05 μM).
- Yang, Ran,Fang, Lei,Li, Jia,Zhang, Yong-Qing
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p. 587 - 592
(2019/03/21)
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- Steroidal glycosides from the underground parts of Hosta ventricosa and their anti-inflammatory activities in mice
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Two new pregnane glycosides, 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside} (1) and 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(2), have been isolated along with two known spirostanol saponins from the underground parts of Hosta ventricosa. Their structures were elucidated on the basis of chemical and spectral evidence. The anti-inflammatory activities of these steroidal glycosides were evaluated using a xylene-induced ear edema model. Our results indicated that the compounds exhibited promising anti-inflammatory activities.
- Chu, Hong-Biao,Li, Nan-Nan,Zhang, Zong-Ping,Hu, Xiao-Yue,Yu, Cai-Yun,Hua, Lei
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p. 1766 - 1774
(2019/07/16)
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- Isolation and structure elucidation of a new flavonol glycoside from Sabia Parviflora
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A new flavonol glycoside named Sabiapside A (1), along with four known compounds, quercetin-3-O-gentiobioside (2), camellianoside (3), isobariclisin-3-O- rutinoside (4), tsubakioside A (5), was isolated from Sabia parviflora. Their structures were elucidated by extensive spectroscopic analysis including MS, UV, IR and NMR data. The antioxidant activities of these glycosides evaluated by ABTS+ and DPPH radical scavenging reaction was higher than that of vitamin C used as the reference antioxidant.
- Sun, Qingwen,Pan, Guoji,Xu, Wenfen,Lu, Xian,Bai, Caihong,Liu, Mengge,Chen, Yinrui
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p. 2408 - 2413
(2019/11/14)
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- New steroidal glycosides from the roots of Asparagus cochinchinensis
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Steroidal saponins were the main active constituents of the traditional medicinal herb Asparagus cochinchinensis. A phytochemical investigation of A. cochinchinensis roots led to the isolation of nine new steroidal glycosides (1–9) and seven known analogues (10–16). Their structures were established by spectroscopic analyses as well as necessary chemical evidence.
- Pang, Xu,Gao, Lin,Wang, Bei,Chen, Xiao-Juan,Zhang, Jie,Guo, Bao-Lin,Ma, Bai-Ping
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p. 205 - 216
(2021/02/03)
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- Triterpene glycosides and phenylpropane derivatives from Staurogyne concinnula possessing anti-angiogenic activity
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After anti-angiogenic activity screening, the potential n-butanol layer partitioned from the ethanol extract of Staurogyne concinnula was conducted. Further purification by Diaion HP20 column and preparative HPLC chromatography, four undescribed triterpen
- Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Pan, Wen-Pin,Cheng, Jing-Jy,Lee, Ching-Kuo,Kuo, Yao-Haur
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- Dihydrostilbene glycosides from Camellia sasanqua and their α-glucosidase and α-amylase inhibitory activities
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Using chromatographic methods, three new dihydrostilbene glycosides, sasastilbosides A-C (1-3) and four known compounds, catechin (4), rutin (5), nicotiflorin (6), and rehmaionoside A (7) have been isolated from Camellia sasanqua Thunb. Their chemical structures were elucidated by spectroscopic methods (1 D-, 2 D-NMR) and mass spectra. Compounds 1-7 were evaluated for α-glucosidase and α-amylase inhibitory effects. Compounds 3 and 4 showed α-glucosidase inhibitory activity with IC50 values of 77.6 ± 1.6 and 72.4 ± 1.3 μM, respectively. Compound 1 showed α-amylase inhibitory activity with IC50 value of 53.7 ± 1.6 μM.
- Cuc, Nguyen Thi,Cuong, Nguyen The,Anh, Luu The,Yen, Duong Thi Hai,Tai, Bui Huu,Thu Trang, Duong,Yen, Pham Hai,Kiem, Phan Van,Nam, Nguyen Hoai,Minh, Chau Van,Nhiem, Nguyen Xuan
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supporting information
p. 4025 - 4031
(2020/05/25)
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- Cytotoxic triterpenoid saponins from Thalictrum atriplex
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Two new cycloartane glycosides, cycloatriosides A and B (1–2), and a new oleanolic acid glycoside, thaliatrioside A (3), along with 7 known triterpenoids (4–10) were isolated from Thalictrum atriplex. The structures of the new compounds were established as 3-O-β-D-galactopyranosyl (20S, 24 R)-3β,16β,25,29-tetrahydroxy-20,24-epoxycycloartane-29-O-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl-(1→2)-α-arabinopyranosyl-3β,22ξ,30-trihydroxycycloart-24-en-21-oic acid α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (2) and 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-oleanolic acid 28-O-β-D-glucopyranosyl ester (3) on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis. Their cytotoxic activities against human lung cancer cells A549 and human breast cancer cells MDA-MB-231 were evaluated using MTT method. Compound 9 showed cytotoxicity against MDA-MB-231 cell line with the IC50 value of 72.53 ± 1.08 μM.
- Meng, FanCheng,Wei, XiaoDong,Sun, Yan,Zeng, QingHong,Wang, Guowei,Lan, XiaoZhong,Liao, ZhiHua,Chen, Min
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p. 5757 - 5764
(2020/10/20)
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- Studies on Bignoniaceae: Newbouldiosides D-F, Minor Phenylethanoid Glycosides from Newbouldia laevis, and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata
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Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D-F. Their structures were elucidated by spectroscopic methods as β-(3,4-dihydroxyphenyl)ethyl 5-O-syringoyl-β-D-apiofuranosyloxy-(1 → 2)-O-[ α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-[ α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, and β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 2)-6-O-E-sinapoyl-β-D-glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5-O-α-L-rhamnopyranosyl-7-O-β-D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7-O-(2″-O-formyl)-β-D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety.
- Kolodziej, Herbert
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p. 989 - 997
(2020/11/18)
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- Manniosides B-F, five new triterpenoid saponins from the leaves of Schefflera mannii (Hook.f.) Harms
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Fifteen triterpenoid saponins including five new compounds (Mannioside B: 3β-[(β-D-glucopyranosyl)oxy]urs-12-en-28-oic acid α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (1), mannioside C: 3β-[(β-D-glucopyranosyl)23-dioxy
- Ponou, Beaudelaire K.,Tanaka, Chiaki,Teponno, Rémy B.,Tapondjou, Azefack L.,Miyamoto, Tomofumi
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supporting information
(2021/03/09)
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- A new and 23 known cardenolide glycosides from Thevetia neriifolia seeds and their cytotoxic activities against human oral carcinoma cell lines
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Phytochemical analysis of Thevetia neriifolia seeds resulted in the isolation of one new (1) and 23 known (2-24) cardenolide glycosides. The structure of 1 was determined based on one- and two-dimensional NMR spectroscopic analysis and acid hydrolytic cleavage reaction. The effect of the cytotoxic activity of 1-24 on three human oral carcinoma cell lines was assessed. The cell lines included Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, HSC-4 human tongue carcinoma cells, and HGF human gingival fibroblast cells. The isolated compounds had a cytotoxic effect on the carcinoma cells with IC50 values ranging from 0.004 μM to 64.9 μM. The structure-activity relationship is also discussed.
- Tatsuno, Satoru,Iguchi, Tomoki,Kuroda, Minpei,Ishihara, Mai,Sakagami, Hiroshi,Mimaki, Yoshihiro
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supporting information
p. 4388 - 4393
(2020/01/31)
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- Triterpenoid glycosides from the rhizomes of Allium ascalonicum and their anoctamin-1 inhibitory activity
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Ten triterpenoid glycosides including two undescribed compounds (1 and 2) were isolated from the methanol extract of Allium ascalonicum rhizomes. These compounds were structurally elucidated to be 3β-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-19α-hydroxyolean-12-ene-28-oic acid 28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl] ester (1), 3-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl-3β,19α-dihydroxyoleanane-12-en-28-oic acid (2), lactifoloside C (3), lactifoloside H (4), randiasaponin IV (5), kudinoside G (6), ilexkudinoside W (7), lactifoloside G (8), kudinoside D (9), and ilexkudinoside T (10) by analyzing their HR-ESI-MS, NMR spectral data and by comparison with those reported in the literature. Compounds 1–10 were evaluated for anoctamin-1 (ANO1) inhibitory activity using yellow fluorescent protein reduction assays. At the concentration of 30 μM, compounds 2 and 9 displayed moderate ANO1 inhibitory percentages of 28.9 ± 0.85% and 26.2 ± 0.65%, respectively.
- Mai, Nguyen Thi,Dung, Duong Thi,Nga, Tran Thuy,Xuan, Vu Thi,Doan, Vu Van,Tai, Bui Huu,Nhiem, Nguyen Xuan,Yen, Pham Hai,Kiem, Phan Van,Seo, Yohan,Namkung, Wan,Park, SeonJu,Kim, Seung Hyun
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supporting information
p. 4338 - 4346
(2020/01/31)
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- New dammarane-type glycosides from Gynostemma pentaphyllum and their lipid-lowering activity
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Gynostemma pentaphyllum (Thunb.) Makino has a long history as food and diary supplement in China. At present, there are some products for hyperlipidemia in the market, including G. pentaphyllum tea, healthy wine and healthy food. In order to discover proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibitors, fourteen new triterpenoid saponins named gypenoside LXXXVIII-CI (1–14) along with six known compounds (15–20) were isolated from G. pentaphyllum. Their structures were elucidated by means of various spectroscopic techniques. Eight isolates were evaluated the inhibitory effect on PCSK9 in HepG2 cells. The results showed that three dammarane-type glycosides (2, 3, 15) remarkably reduced PCSK9 expression at 10 μM concentration. These findings suggested that G. pentaphyllum was worthy of further investigation to find small molecule PCSK9 inhibitors and facilitate their utilization as functional food ingredients.
- Weng, Xin,Lou, Yun-Yun,Wang, Yun-Shan,Huang, Ya-Ping,Zhang, Jian,Yin, Zhi-Qi,Pan, Ke
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- Three novel furospirostanol glycosides and a steroidal alkaloid glycoside from the bulbs of Fritillaria camtschatcensis (L.) Ker Gawl., and their cytotoxicity
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Three novel steroidal glycosides (1–3) and a previously described steroidal alkaloid glycoside (4) have been isolated from the bulbs of Fritillaria camtschatcensis (L.) Ker Gawl. (Liliaceae). The structures of novel compounds 1–3 were characterized based on NMR spectroscopy and chemical transformations. Compounds 1–3 are furospirostanol glycosides bearing a (3S)-3-hydroxy-3-methylglutaryl moiety at C-26 in the aglycone. Compounds 1–4 were evaluated in terms of their cytotoxic activities toward HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human lung small cell carcinoma cells. Only 4 showed moderate cytotoxicity against HL-60, A549, and SBC-3 cells with IC50 values of 22.9, 13.3, and 11.9 μM, respectively. Compound 4 was found to cause necrotic-like cell death in HL-60 cells.
- Iguchi, Tomoki,Kuroda, Minpei,Takayama, Hiroshi,Mimaki, Yoshihiro
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- New Phenylpropanoid Glycosides from Illicium majus and Their Radical Scavenging Activities
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Chemical investigation of the ethanol extract of the branch and leaves of Illicium majus resulted in the isolation of four new phenylpropanoid glycosides (1–4) and one new phenolic glycoside (9), along with 13 known ones. Spectroscopic techniques were use
- Li, Fang,Yan, Ting-Ting,Fu, Ying-Ying,Zhang, Nen-Ling,Wang, Lei,Zhang, Yan-Bing,Du, Juan,Liu, Ji-Feng
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- Isolation, characterization and antioxidant, tyrosinase inhibitory activities of constituents from the flowers of cercis glabra ‘spring-1’
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A phytochemical study on the flowers of Cercis glabra ‘Spring-1’ led to the isolation and identification of twelve compounds, including one new compound named as 1-O-α-L-rhamnosyl-(E)-phytol (1) and eleven known compounds. Their structures were elucidated based on physical data analysis, including HR-ESI-MS, NMR, UV, IR, and acid hydrolysis. All compounds were screened for in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl method. Compounds 4 and 5 exhibited obvious DPPH radical scavenging activities. All the isolates were tested for their inhibitory effects on mushroom tyrosinase, and compounds 6, 7, 10 and 11 showed moderate tyrosinase inhibitory activities.
- Shu, Penghua,Li, Yamin,Luo, Yuehui,Yu, Mengzhu,Fei, Yingying,Liu, Wanrong,Yang, Yuan,Wei, Xialan,Zhang, Yuhuan,Tu, Tieyao,Zhang, Lin
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p. 254 - 260
(2021/05/05)
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- Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn
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In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides A─C (1─3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (1), 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (2), and 3-O-{α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-[α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.
- Le Doux Kamto, Eutrophe,Noté, Olivier Placide,Kinyok, Mc Jesus,Wilhelm, Anke,Mbing, Joséphine Ngo,Antheaume, Cyril,de Théodore Atchadé, Alex,Pegnyemb, Dieudonné Emmanuel,Ndinteh, Derek Tantoh,Haddad, Mohamed,Bonnet, Susan L.
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- Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk
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In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosi
- Moffi Biang, Armand Emmanuel,Messi, Lin Marcellin,Le Doux Kamto, Eutrophe,Simo, Line Made,Lavedan, Pierre,Vedrenne, Marc,Mbing, Josephine Ngo,Pegnyemb, Dieudonné Emmanuel,Haddad, Mohamed,Noté, Olivier Placide
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- Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities
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Three undescribed oleanane type triterpenoid saponins (1–3), along with one known saponin (4) were isolated from the whole herb of Hylomecon japonica. Their structures were elucidated by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HR-ESI-MS) and chromatographic date (GC and LC) as 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl ester (3), 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl ester (4). All saponins possess a partial sequence β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl at C-3 of the aglycon. Compound 1 has cytotoxic activity against human colon cancer cell lines HT29, 3 against human gastric cancer cell lines AGS, and 4 against human lung cancer cell lines A549, AGS and HT29. Among them, compounds 3 and 4 showed significant inhibitory effect against AGS with IC50 value of 6.01 ± 1.4 μM, 3.66 ± 1.8 μM, respectively. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon japonica and their bioactivities.
- Li, Fei,Wu, Si-Tong,Qu, Ming-Hui,Wang, Yi-Xiao,Ma, Chun-Liu,Yu, Bai-Hong,Wang, Guang-Shu
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- Microbial transformation of icariin and its derivatives
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Microbial transformation is an important tool to perform selective conversion of compounds to derivatives which are difficult to produce synthetically. In order to obtain icariside II and icaritin, the active components in Herba Epimedii in vivo, biotransformation studies using microbes as biocatalysts were carried out. Icariside II (2) and icaritin (3) were produced through biotransformation of icariin (1) using the fungi Hormoconis resinae and Mortierella ramanniana var. angulispora in 98% and 92% yields, respectively. In the subsequent transformation studies, 2 was deglycosylated to form 3 by Gliocladium deliquescens, whereas 3 was further converted to a novel compound icaritin-3-O-β-d-glucopyranoside (4) and previously known icaritin-3,7-O-β-d-diglucopyranoside (5) by Mucor hiemalis. Biological evaluation of these compounds using MTT assay exhibited potent cytotoxic activities against human cancer cell lines A549, A375P, and MCF-7, with icariin being the most active, indicating that glycosylation plays a role in the cytotoxic activity.
- Han, Fubo,Kim, Ji Hye,Lee, Ik-Soo
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- Triterpenoid saponins from the leaves and stems of Pericampylus glaucus and their insulin mimetic activities
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During an attempt to discover insulin mimetics, thirteen new triterpenoid saponins (1–13), including three phytolaccagenic acids (1, 2, and 12) and ten serjanic acids (3–11 and 13), as aglycones were isolated from a 70% ethanol extract of leaves and stems from Pericampylus glaucus. The chemical structures of compounds 1–13 were determined through spectroscopic data analysis, including NMR, IR, and HRESIMS. All isolated compounds (1–13) were evaluated using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) as a fluorescent-tagged glucose probe to determine their stimulatory effects on glucose uptake in differentiated 3 T3-L1 adipocyte cells. Consequently, four compounds (4, 7, 11, and 12) exhibited stimulatory effects on glucose uptake.
- Lee, Hee-Ju,Cho, Hyo-Moon,Park, Eun-Jin,Lee, Ba-Wool,Nghiem, Duc-Trong,Pham, Ha-Thanh-Tung,Pan, Cheol-Ho,Oh, Won-Keun
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- Three Previously Undescribed Chlorophenyl Glycosides from the Bulbs of Lilium regale
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Three previously undescribed chlorophenyl glycosides, (2,4,6-trichloro-3-hydroxy-5-methoxyphenyl)methyl β-D-glucopyranoside (1), (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside (2) and 4-chloro-3-methoxy-5-methylphenyl 6-O-(6-deoxy-β-L-mannopyranosyl)-β-D-glucopyranoside (3) were obtained from Lilium regale. The absolute configurations of these new finds were elucidated by comprehensive analyses of spectroscopic data combined with acid hydrolysis derivatization. (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside (2) can inhibit the proliferation of lung carcinoma A549 cells with an IC50 value of 29 μΜ.
- Deng, Yun,Guo, Dale,Guo, Wenxiu,Liu, Ding,Pei, Jin,Peng, Cheng,Xie, Xiaofang,Yan, Jie,Zheng, Haoyuan,Zhou, Lanyu
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- Angucycline and angucyclinone derivatives from the marine-derived Streptomyces sp.
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Atramycin C (1), one new angucycline bearing an O-6 rhamnose side chain, along with one new highly hydroxylated angucyclinone emycin G (2), and ten known analogs (3–12) were isolated from the marine-derived Streptomyces sp. strain BHB-032. Their structures were assigned by spectroscopic analysis and comparison with literature data. The absolute configuration of the sugar unit of 1 was assigned as 6-O-α-l-rhamnoside, based on the analysis of the coupling constants and chemical derivatization, whereas the absolute configuration of 2 was determined by X-ray diffraction. Furthermore, the stereochemistry of saccharothrixin A (3) and SNA-8073-A (4) was established unequivocally by X-ray crystallography for the first time. Compounds 1 and 2 exhibited moderate antimicrobial activities with minimum inhibitory concentration (MIC) values ranging from 16 to 64 μg/ml.
- Gong, Ge,Guo, Lin,Li, Zhi,Liu, Ming,Xie, Ze-Ping,Xu, Bo,Yang, Ying-Jie,Zhang, Lu,Zhang, Shu-Min
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- Phytochemical Investigation of the Roots of Ipomoea asarifolia and Antiproliferative Activity of the Isolated Compounds against Multiple Myeloma Cells
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Ipomoea asarifolia is a herbaceous plant belonging to the family Convolvulaceae and is native to tropical regions of Africa, America, and Asia. A dichloromethane root extract showed antiproliferative activity against multiple myeloma cells (RPMI 8226). The phytochemical investigation led to the isolation of 15 compounds. Compounds 1–4, named (4S,8S)-1-(furan-3-yl)-9-hydroxy-4,8-dimethylnonane-1,6-dione, isoferulic acid hexadecyl ester, caffeic acid hexadecyl ester, and asarifolin I, respectively, are described for the first time. The structures of these molecules were established from their NMR, UV, IR spectroscopic, and MS data. 4-Hydroxycinnamic acid hexadecyl ester (5), 4-hydroxycinnamic acid octadecyl ester (6), 4-hydroxycinnamic acid eicosyl ester (7), caffeic acid octadecyl ester (8), pescapreins III, IV, XXI, XXIII, XXV, and XXVI (9–14), and stoloniferin III (15) were also isolated. All compounds were tested against a multiple myeloma cell line (RPMI 8226). When their IC50 value was lower than 10 μM, the compounds were also tested against two other multiple myeloma cell lines, MM.1S and MM.1R. Compound 3 was the most potent, with an IC50 value of 3.0 μM against RPMI 8226 cells.
- Christen, Philippe,Cuendet, Muriel,Imeri, Deniza,Karimou, Soumana,Quirós-Guerrero, Luis,Saraux, Noémie
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- Chemical composition and biological activity of salicornia fruticosa L.
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Plants have been used as a source of traditional medicine to treat many diseases and conditions for many years. They considered as excellent source of phytochemicals which showed antioxidant and anticancer activities. The aim of the present study is to investigate the chemical composition and to determine the anticancer activity of Salicornia fruticosa (Chenopodiaceae) methanolic extract. S. fruticosa proved to be a source of isorhamnetin and its glycosides and showed anticancer activities. Seven major flavonoids were isolated and identified from the cytotoxic methanolic extract. The isolated compounds were identified, as quercetin 3',4'-dimethyl ether (1), isorhamnetin (2), isorhamnetin 3-O-rhamnoside (3), isorhamnetin 3-O-glucoside (4), isorhamnetin 3-O-rutinoside (5), isorhamnetin 3-O-neohesperidoside (6), isorhamnetin 3-O-rhamnosyl(1-2)arabinoside (7), by chromatographic analysis, chemical and spectroscopic tools (acid hydrolysis, UV, 1H and 13C NMR). Compounds 1 and 3-7 were isolated for the first time from the plant under investigation. The evaluation of cytotoxic activity of the methanolic extract against HCT-116, HepG2, A549 and MCF-7 human cancer cells, by MTT assay, revealed the higher potency of S. Fruticosa extract with IC50 [2.6. 10.9, 37.9, 5.4 (mg/ml)] respectively, comparable to that of doxorubicin. The obtained results suggested that the investigated plant could be used for future development of naturally occurring anticancer agent. Subclinical and clinical trials on polar fractions of S. fruticosa are mandatory to pave the way for its use in treatment of cancer diseases (HCT-116, HepG2, A549 and MCF-7).
- Abdel Elatif,Shabana,Ibrahim,Mansour,Awad,Sharaf
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p. 1713 - 1721
(2020/09/01)
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- Novel polysaccharide from Chaenomeles speciosa seeds: Structural characterization, α-amylase and α-glucosidase inhibitory activity evaluation
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Purification and structural characterization of a novel polysaccharide fraction from Chaenomeles speciosa seeds were investigated. After hot water extraction and ethanol precipitation, the crude polysaccharide was sequentially purified with Cellulose DEAE-52 and gel-filtration chromatography, and a highly purified polysaccharide fraction (F3) was obtained. The structure of F3 was characterized by high-performance gel permeation chromatography (HPGPC), high performance liquid chromatography (HPLC), ultraviolet-visible (UV), Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) spectrum, together with methylation, scanning electron microscopy (SEM), atomic force microscope (AFM), and Congo-red test analysis. The results indicated that F3 was a homogeneous polysaccharide fraction with a molecular weight of 8.65 × 106 Da, and it was composed of Rha, GlcA, Gal, and Ara in a molar ratio of 6.34:5.73:47.14:40.13. The backbone of F3 was consisted of →3,6)-Galp-(1→, and the side chains of F3 were composed of Araf-(1→, →4)-GlcpA-(1→, →4)-Galp-(1→ and →3)-Rhap-(1→. The hypoglycemic assays demonstrated F3 had good α-amylase and α-glucosidase inhibition activities, and their IC50 values were 6.24 mg/mL and 4.59 mg/mL respectively. Thus, the polysaccharide from Chaenomeles speciose could be applied as a potential natural source in retarding postprandial hyperglycemia effects.
- Cheng, Jiang,Deng, Yejun,Huang, Lixin,Liu, Lujie,Wang, Xiang,Xie, Pujun,Zhang, Caihong
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p. 755 - 766
(2020/03/18)
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- Cytotoxic steroidal saponins from the rhizome of Anemarrhena asphodeloides
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Two novel steroidal saponins, timosaponin V and W (1 and 2), together with seven known steroidal saponins (3–9), were isolated from the rhizomes of Anemarrhena asphodeloides Bunge. Their structures were elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, 1H–1H COSY, and NOESY), and MS analyses. The cytotoxic activities of the isolates were evaluated. Compound 1 showed a significant cytotoxic activity against MCF-7 and HepG2 cell lines with IC50 values of 2.16 ± 0.19 μM and 2.01 ± 0.19 μM, respectively.
- Zhao, Yun-Fang,Zhou, Jing,Zhang, Min-Jie,Zhang, Min,Huang, Xue-Feng
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- Three new phenylacetamide glycosides from Dracocephalum tanguticum Maxim and their anti-hyperglycemic activity
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Three new phenylacetamide glycosides (1–3) together with one known phenylacetamide glycoside (4) and two known flavonoid glycosides (5–6) were isolated from whole plants of Dracocephalum tanguticum. The structure of all compounds were elucidated based on spectroscopic data analysis and comparison with data reported in related literature. Compounds (1–3) were evaluated for their anti-hyperglycemic and anti-fungal (Candida albicans) activities, the results revealed that all of them showed moderate activity with 3T3-L1 adipocytes glucose consumption rate of 20.80 ± 1.47%, 21.48 ± 2.44%, and 21.57 ± 1.35%, respectively at the final concentration of 25 μM. However, none of them showed obvious Candida albicans inhibitory activity.
- Ma, En-Guang,Wu, Hai-Yan,Hu, Li-Jiao,Wei, Min,Mou, Lin-Yun,Li, Gan-Peng
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p. 1827 - 1835
(2019/02/03)
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- Isolation of chemical constituents with anti-inflammatory activity from Reineckia carnea herbs
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Three new saponins (1–3), a new natural product (4) and six other known compounds (5–10) were isolated from the whole Reineckia carnea plant. Their structures were established by comparison of their NMR spectra and MS data with literature data. In addition, all the isolated compounds were evaluated in vitro for anti-inflammatory activities against LPS-stimulated nitric oxide (NO) production in RAW 264.7 macrophages. Compounds 1–4 exhibited anti-inflammatory activities with IC50 values of 37.5 μM, 31.4 μM, 34.6 μM, and 56.1 μM, respectively. Furthermore, compounds 5–10 showed anti-inflammatory activities with IC50 values ranging from 20.3 to 42.9 μM.
- Xu, Xu,Tan, Ting,Zhang, Jing,Li, Zhi-Feng,Yang, Shi-Lin,Wen, Quan,Feng, Yu-Lin
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p. 303 - 315
(2019/03/14)
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- Syringoleosides A?H, secoiridoids from syringa dilatata flowers and their inhibition of NO production in LPS-induced RAW 264.7 Cells
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Repeated column chromatography of Syringa dilatata flowers, a native shrub to Korea, led to the isolation of eight new oleoside-type secoiridoids, syringoleosides A?H (1?8), as well as five known secoiridoids (9?13). The new chemical structures were identified through spectroscopic data analysis, as well as the application of chemical methods. Compounds 1, 2, 6, 7, 11, and 13 showed suppression effects on NO production in LPS-induced RAW 264.7 cells, with IC50 values ranging from 32.5 ± 9.8 to 65.7 ± 11.0 μM, and no visible toxicity. The content of the major secoiridoids in S. dilatata flowers, compounds 1, 4, 5, 8, 9, 12, and 13, were determined through HPLC analysis.
- Gwag, Jung Eun,Lee, Yeong-Geun,Kim, Hyoung-Geun,Lee, Dong-Sung,Lee, Dae Young,Baek, Nam-In
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p. 2655 - 2663
(2020/10/09)
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- Novel steroidal glycosides from the whole plants of helleborus foetidus
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Phytochemical analysis of the whole Helleborus foetidus plants identified 28 steroidal glycosides (1-28), including 20 novel spirostanol glycosides (1-20) and a novel furostanol glycoside (21). The structures of the newly identified compounds were elucidated by two-dimensional NMR spectroscopy and hydrolytic cleavage. Compounds 12, 13, and 15 were determined to be spirostanol trisdesmosides bearing sugar moieties at the C-1, -21, and -24 hydroxy groups of the aglycone unit. The isolated compounds were subsequently evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung carcinoma cells. In particular, 7 showed cytotoxic activity against the HL-60 and A549 cells, with IC50 values of 5.9 and 6.6μM, respectively, whereas 19 was selectively cytotoxic to A549 cells with an IC50 value of 5.5μM.
- Iguchi, Tomoki,Uchida, Yuka,Takano, Shingo,Yokosuka, Akihito,Mimaki, Yoshihiro
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p. 273 - 287
(2020/11/26)
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- Angelicosides I-IV, four undescribed furanocoumarin glycosides from Angelica dahurica roots and their tyrosinase inhibitory activities
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Angelica dahurica is an important medicinal plant, which has been widely used in medicines and skin-whitening products. In the investigation of phytochemicals present in A. dahurica roots, three unusual furanocoumarin rhamnosides, angelicosides I–III (1–3), one undescribed furanocoumarin glucoside, angelicoside IV (4), together with eight known compounds (5–12) were isolated. Their structures were characterized by a combination of UV, IR, NMR, HRESIMS, along with acid hydrolysis and enzymatic hydrolysis. All the isolated compounds were tested for their mushroom tyrosinase inhibitory activities, and compounds 1, 2, and 11 showed moderate activities.
- Fei, Yingying,Ju, Zhiyu,Li, Junping,Li, Yamin,Liu, Hao,Niu, Haoying,Shu, Penghua,Wei, Xialan,Xiao, Fugang,Xu, Zhihong,Zhang, Lingxiang,Zhu, Huiqing
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- Three new spirostanol glycosides from Helleborus thibetanus
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An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1 D, 2 D NMR spectra, together with IR and MS met
- Li, Zhang-Peng,Su, Yan-Fang,Wei, Zi-Ye,Yang, Feng-Ying,Zhang, Hui
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p. 975 - 980
(2019/01/09)
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- Flavonol glycosides from Fissistigma maclurei
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Two new flavonol glycosides, fissmacosides A (1) and B (2) along with two known flavonol glycosides, kaempferol 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside (3) and kaempferol 3-O-β-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→6)-[4-(E)-feruloyl]-β-d-galactopyranoside (4) were isolated from the methanol extract of the leaves of Fissistigma maclurei Merr. Their structures were determined on the basis of extensive spectroscopic methods, including 1D-, 2D-NMR, and MS data.
- Ba, Nguyen Van,Men, Chu Van,Khi, Nguyen Tien,Tiet, Tran Viet,Khanh, Pham Gia,Quang, Le Bach,Chuyen, Nguyen Van,Tien, Vu Dinh,Nhiem, Nguyen Xuan,Kiem, Phan Van
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p. 1011 - 1017
(2019/11/21)
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- Sesquiterpenoids, phenolic and lignan glycosides from the roots and rhizomes of Clematis hexapetala Pall. and their bioactivities
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Approximately 17 compounds were isolated from a 60% EtOH aqueous extract of the roots and rhizomes of Clematis hexapetala Pall., including three new guaianolide sesquiterpenoids with 5/7/5-fused rings and 3S-configuration (1–3), five new prenylated tetra-substituted phenolic glycosides (4–8) with 6/6-fused 9H-benzopyran skeleton (5) and 6/7-fused 7,10-dihydro-benzoxepin skeleton (6–8), one new isoferulyl glucoside (9), two new furofuran lignan diglucosides (10–11), and six known compounds. The chemical structures of the new compounds were elucidated via spectroscopic data and electronic circular dichroism (ECD) analyses in combination with a modified Mosher's method. The possible biosynthetic relationships of prenylated tetra-substituted phenols were postulated. In the in vitro assays, compound 16 exhibited moderate TNF-α secretion inhibitory activity with IC50 value of 3.419 μM. Compounds 14–16 displayed potent PTP1B enzymatic inhibitory activities with inhibition ratios of 48.30–86.00%. And compound 16 showed significant PTP1B enzymatic inhibition with IC50 value of 4.623 μM.
- Cai, Lu,Han, Shao-Wei,Li, Shuai,Shao, Si-Yuan
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- A new oleanane type pentacyclic triterpenoid saponin from the husks of xanthoceras sorbifolium bunge and its neuroprotection on PC12 cells injury induced by Aβ25-35
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A new triterpenoid saponin (1), 3-O-[β-D-glucopyranosyl(1→6)]-(2′-angeloyl)-β-D-glucopyranosyl-28-O-β-D-glucopyranosyl(1→6)[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-21-O-acetyl-16-deoxybarringtogenol C, together with four known saponins (2 ~ 5) were isolated from the husks of Xanthoceras sorbifolium Bunge. Their structures were characterized by HR-ESI-MS, 1D-NMR, 2D-NMR spectra and chemical methods. Compound 1 exhibited excellent neuroprotection on PC12 cells injury induced by Aβ25-35 at the doses of 150 μmol/L and 200 μmol/L. The cell viabilities were (76.18 ± 2.09) % and (76.02 ± 3.20) %, respectively. (Figure presented.).
- Ding, Kewen,Guo, Sirui,Rong, Weiwei,Li, Qing,Liu, Ran,Xu, Huarong,Yin, Yidi,Bi, Kaishun
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p. 3212 - 3218
(2020/11/25)
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