- New triterpenoids from the red sea sponge Siphonochalina siphonella
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Clear differences were found when comparing the chemical content of the northern, Gulf of Eilat, to the southern-central, Dahlak archipelago, Red Sea sponge Siphonochalina siphonella. The Dahlak sponge was found to be richer in the more polar triterpenes. Nine new compounds (1-4, 7, 8, 15-17) were isolated and identified, among them two sipholane glycosides, sipholenoside A and B (7 and 8), and one compound, dahabinone A (17), possessing a new skeleton.
- Kashman,Yosief,Carmeli
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- Exopolysaccharide Produced by Probiotic Bacillus albus DM-15 Isolated From Ayurvedic Fermented Dasamoolarishta: Characterization, Antioxidant, and Anticancer Activities
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An exopolysaccharide (EPS) was purified from the probiotic bacterium Bacillus albus DM-15, isolated from the Indian Ayurvedic traditional medicine Dasamoolarishta. Gas chromatography-mass spectrophotometry and nuclear magnetic resonance (NMR) analyses revealed the heteropolymeric nature of the purified EPS with monosaccharide units of glucose, galactose, xylose, and rhamnose. Size-exclusion chromatography had shown the molecular weight of the purified EPS as around 240 kDa. X-ray powder diffraction analysis confirmed the non-crystalline amorphous nature of the EPS. Furthermore, the purified EPS showed the maximum flocculation activity (72.80%) with kaolin clay and emulsification activity (67.04%) with xylene. In addition, the EPS exhibits significant antioxidant activities on DPPH (58.17 ± 0.054%), ABTS (70.47 ± 0.854%) and nitric oxide (58.92 ± 0.744%) radicals in a concentration-dependent way. Moreover, the EPS showed promising cytotoxic activity (20 ± 0.97 μg mL–1) against the lung carcinoma cells (A549), and subsequent cellular staining revealed apoptotic necrotic characters in damaged A549 cells. The EPS purified from the probiotic strain B. albus DM-15 can be further studied and exploited as a potential carbohydrate polymer in food, cosmetic, pharmaceutical, and biomedical applications.
- Kalimuthu, Palanisamy,Ma, Yongkun,Mathivanan, Krishnamurthy,Rai, Amit Kumar,Saravanan, Kandasamy,Sathiyanarayanan, Ganesan,Sekar, Soundarapandian,Sudharsan, Kumaresan,Vinothkanna, Annadurai
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- New triterpenoid saponin from the stems of Albizia adianthifolia (Schumach.) W.Wight
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As part of our continuing study of apoptosis-inducing saponins from Cameroonian Albizia genus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated from Albizia adianthifolia stems. The s
- Toukea, Daniel Djou,Kamto, Eutrophe Le Doux,Simo, Line Made,Mbing, Joséphine Ngo,Antheaume, Cyril,Haddad, Mohamed,Noté, Olivier Placide,Pegnyemb, Dieudonné Emmanuel
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p. 780 - 788
(2020/08/19)
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- Bioactive oleanane-type saponins from Hylomecon Japonica
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Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.
- Li, Fei,Ma, Chun-Liu,Qu, Ming-Hui,Wang, Guang-Shu,Wang, Yi-Xiao,Wu, Si-Tong,Yu, Bai-Hong
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- A novel acylated flavonol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica
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In recent years, the scientific interest and particularly the economic significance of halophytic plants has been highly demanding due to the medicinal and nutraceutical potential of its bioactive compounds. A xero-halophyte Bassia indica is deemed to be
- Othman, Ahmed,Amen, Yhiya,Shimizu, Kuniyoshi
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- Oleanane-type saponins and prosapogenins from Albizia julibrissin and their cytotoxic activities
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Two undescribed oleanane-type saponins, julibrosides K–L, along with three undescribed oleanane-type prosapogenins, julibrosides M–O, were isolated from the stem bark of Albizia julibrissin Durazz. and the mild alkaline hydrolysate of the total saponin, r
- Han, Qinghua,Qian, Yi,Wang, Xuda,Zhang, Qingying,Cui, Jingrong,Tu, Pengfei,Liang, Hong
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- Bioassay-guided isolation of cyclooxygenase-2 inhibitory and antioxidant phenylpropanoid derivatives from the roots of Dendropanax dentiger
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The root of Dendropanax dentiger (Harms) Merr. is a traditional Chinese medicine that has been used to treat inflammation-related diseases with little scientific validation. In this study, a bioassay-guided phytochemical investigation of D. dentiger led to the isolation of 19 phenylpropanoid derivatives including one new compound (1) and 18 known ones (2–19). Their structures were elucidated by NMR and HRMS as well as comparison with literature data. The ability of cyclooxygenase-2 (COX-2) inhibition and antioxidant of all isolated compounds were measured in vitro. Chlorogenic acid derivatives (14–19) exhibited outstanding COX-2 inhibitory (IC50 = 5.1–93.4 μM) and antioxidant (IC50 = 13.2–31.9 μM) activities. Moreover, the tight structure-activities relationships were proposed. This is the first report on the COX-2 inhibitory activity of phenylpropanoids and D. dentiger.
- He, Junwei,Liu, Ronghua,Liu, Shengzhang,Yang, Li
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- Hepatoprotective, cytotoxic, antimicrobial and antioxidant activities of Dioon spinulosum leaves Dyer Ex Eichler and its isolated secondary metabolites
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Given the lack of adequate research on Dioon spinulosum (D. spinulosum) Dyer Ex Eichler, this study was conducted focusing on different biological activities and phytochemical investigation of D. spinulosum for the first time. D. spinulosum showed strong
- Abo El-Seoud, Kamilia A.,El-Aasr, Mona,Kabbash, Amal,Kassab, Amira A.,Negm, Walaa A.
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supporting information
p. 1 - 11
(2020/07/16)
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- A new triterpenoid saponin from Pulsatilla cernua predicted by NMR-based mosaic method
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A saponin (1) with gypsogenin as aglycone was isolated from the roots of Pulsatilla cernua. The aglycone of compound 1 was considered as gypsogenin which was rarely found in this genus. Its structure was predicted by NMR-based “mosaic” method rapidly, and further confirmed on the basis of spectroscopic data, including 2D NMR spectra and chemical evidence. This work suggested that NMR-based mosaic method is suitable for most of saponins from common species of genus Pulsatilla.
- Bao, Ying,Li, Mei-Chen,Liu, Jian-Yu,Ren, Xu-Hong,Wang, An-Dong,Wang, Xia,Xu, Yong-Nan
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supporting information
p. 909 - 914
(2018/12/14)
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- Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant evaluation of the constituents from Angelica dahurica roots
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Two undescribed phenolic compounds, angelicols A (1) and B (2) and one undescribed coumarin rhamnoside, angelicoside A (3), together with 17 known compounds (4–20) were isolated from the roots of Angelica dahurica. Their structures were characterized by physical data analyses such as NMR, HRESIMS, and X-ray diffraction. Compounds 2, 3, 5, 6 and L-ascorbic acid (positive control) exhibited obvious DPPH radical scavenging activities with IC50 values of 0.36?mM, 0.43?mM, 0.39?mM, 0.44?mM, 0.25?mM, respectively. At a concentration of 25?μM, all compounds showed weaker tyrosinase inhibition activities (%inhibition 50 = 44.29 ± 0.06?μM).
- Shu, Penghua,Li, Junping,Fei, Yingying,Zhu, Huiqing,Yu, Mengzhu,Liu, Anqi,Niu, Haoying,Zou, Simin,Wei, Xialan,Ju, Zhiyu,Xu, Zhihong
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p. 456 - 462
(2019/12/24)
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- Flavonoid glycosides from seeds of Hippophae rhamnoides subsp. Sinensis with α-glucosidase inhibition activity
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Hippophae rhamnoides subsp. Sinensis is a famous traditional medicinal plant in Tibet and Mongolia of China. Three novel flavonoid glycosides and ten known analogues were obtained from the seeds of H. rhamnoides. The structures of new compounds were elucidated by spectroscopics, chemical methods as well as literature data. In vitro assay, compounds 5–9, kaempferol and 70% ethanolic elution fraction showed prominent α-glucosidase inhibitory activities with IC50 values ranging from 8.30 to 112.11 μM, better than that of the positive control, acarbose, whose IC50 value was 1727.07 μM.
- Li, Rui,Wang, Qing,Zhao, Menghao,Yang, Peiming,Hu, Xiao,Ouyang, Danwei
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- Hederagenin glycosides from the fruits of Blighia unijugata
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A phytochemical investigation of Blighia unijugata led to the isolation of eleven hederagenin glycosides. Among these compounds, six are previously undescribed, two are described in their native forms for the first time and three are known whereas firstly isolated from Blighia unijugata. The structure of the undescribed compounds was elucidated on the basis of 2D NMR and mass spectrometry analyses as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester and 3-O-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester. These results revealed the existence of several conserved structural features that could be used as chemotaxonomic markers for the Blighia genus such as the glycosidic sequence 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl, the occurrence of 3-O-acetylated β-D-glucopyranosyl units and the systematic presence of hederagenin as aglycone.
- Petit, Bastien,Mitaine-Offer, Anne-Claire,Delaude, Clément,Miyamoto, Tomofumi,Tanaka, Chiaki,Lacaille-Dubois, Marie-Aleth
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p. 260 - 269
(2019/05/01)
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- Chemical Constituents from the Roots of Polygala arillata and Their Anti-Inflammatory Activities
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A new compound, named arillatanoside E, which was elucidated as 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1 - 3)-β-D-xylopyranosyl-(1 - 4)-α-L-rhamnopyranosyl-(1 - 2)-(4-O-acetyl)-β-D-fucopyranosyl ester, along with 11 known compounds was isolated from the ethanolic extract of the roots of Polygala arillata. The 11 known compounds were identified as oleanolic acid (2), 3′-E-3,4,5-trimethoxy cinnamoyl-6-benzoyl sucrose (3), trans-ferulic acid (4), trans-feruloyl-glucoside (5), feruloyl-glucoside (6), 2,4,6-trimethoxy-1-O-β-D-glycoside (7), 3-methoxy-4-hydroxybenzoic acid (8), monopentadecanoin (9), sinapic acid (10), p-hydroxybenzaldehyde (11), and palmitic acid (12). Among them, seven isolated compounds 1, 2, 4, 5, 7, 8, and 10 exhibited little cytotoxic activity on macrophage RAW 264.7 cells. Then, the inhibitory effects of 7 isolates on nitric oxide (NO) production in lipopolysaccharide-activated macrophages were evaluated. As a result, 3 compounds have significant anti-inflammatory activity, and they were arillatanoside E (1), oleanolic acid (2), and 2,4,6-trimethoxy-1-O-β-D-glycoside (7).
- Xiang, Wei,Zhang, Guo-Dong,Li, Fang-Yi,Wang, Teng-Long,Suo, Tong-Chuan,Wang, Chun-Hua,Li, Zheng,Zhu, Yan
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- Triterpenoid saponins from anemone rivularis Var. Flore-minore and their anti-proliferative activity on HSC-T6 cells
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Five previously undescribed triterpenoid saponins (1–5), along with eight known ones (6–13), were isolated from the whole plants of Anemone rivularis var. flore-minore. Their structures were clarified by extensive spectroscopic data and chemical evidence.
- Wang, Xiao-Yang,Gao, Hui,Xie, Xiao-Jie,Jurhiin, Jirimubatu,Zhang, Mu-Zi-He,Zhou, Yan-Ping,Liu, Rui,Ning, Meng,Han, Jin,Tang, Hai-Feng
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- A new flavonol glycoside and other flavonoids from the aerial parts of Taverniera aegyptiaca
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Isolation of flavonoids from the aerial parts of Taverniera aegyptiaca Bioss. (Fabaceae) led to identification of one new flavonol glycoside, isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (1), along with eleven compounds, which previously have not been isolated from this plant quercetin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (2), isorhamnetin-3-O-α-l-arabinopyranoside (3), quercetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (7), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (8), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside] (9), kaempferol 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (10), isorhamnetin (11), 4,4′-dihydroxy-2′-methoxychalcone (12), formononetin (13) and calycosin (15)] and some compounds already known from this plant [quercetin-3-O-robinobioside (5), isorhamnetin-3-O-robinobioside (6), afrormosin (14) and odoratin (16)].
- Hassan, Ahmed R.,Amer, Khadiga F.,El-Toumy, Sayed A.,Nielsen, John,Christensen, S?ren Br?gger
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supporting information
p. 1 - 5
(2018/04/20)
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- Benzyl and benzaldehyde-derived metabolites from desert actinomycetes Sp. CDS
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Chromatographic purification of the culture broth of Actinomycetes CDS1 provided five new (1-5) and three known (6-8) metabolites. The new compounds 1, 4 and 5 were elucidated due to 1D-, 2D-NMR techniques, FABMS and HR-FABMS analyses. The nature of glycosidic part in 4 was confirmed through optical rotation value and comparison of the Rf value of hydrolyzed sugar with that of standard sample. Compounds 2 and 3 were tentatively identified due to 1H NMR and +ve FAB-MS analysis as mixture in one of the polar minor fractions. Structures of the known compounds 6-8 were determined due to 1H NMR and FABMS analysis.
- Nazir, Mamona,Mustafa, Rizwana,Tousif, Muhammad Imran,Ahmad, Shabir,Khatoon, Tasneem,Ahmad, Ishtiaq
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p. 919 - 923
(2018/10/02)
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- Melanogenesis-Inhibitory and Cytotoxic Activities of Triterpene Glycoside Constituents from the Bark of Albizia procera
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Five oleanane-type triterpene glycosides including three new ones, proceraosides E-G (1-3), were isolated from a MeOH-soluble extract of Albizia procera bark. The structures of 1-3 were determined by use of NMR spectra, HRESIMS, and chemical methods. Compounds 1-5 exhibited inhibitory activities against the proliferation of the A549, SKBR3, AZ521, and HL60 human cancer cell lines (IC50 0.28-1.8 μM). Additionally, the apoptosis-inducing activity of compound 2 was evaluated by Hoechst 33342 staining and flow cytometry, while the effects of 2 on the activation of caspases-9, -8, and -3 in HL60 cells were revealed by Western blot analysis.
- Zhang, Jie,Akihisa, Toshihiro,Kurita, Masahiro,Kikuchi, Takashi,Zhu, Wan-Fang,Ye, Feng,Dong, Zhen-Huan,Liu, Wen-Yuan,Feng, Feng,Xu, Jian
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supporting information
p. 2612 - 2620
(2019/01/04)
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- New triterpene saponins from the aerial parts of: Androsace umbellata
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Six new oleanane-type triterpene saponins, androsides A-F (1-6), along with two known compounds (7-8), were isolated from the aerial parts of Androsace umbellata. The structures were determined on the basis of spectroscopic data and acid hydrolysis. The aglycones in 1-5 are novel structures. Cytotoxicity assays using HepG2, HepG2/ADM, MCF-7, MCF-7/ADR and MDA-MB-231 cell lines indicated that 7 and 8, both bearing a 13β,28-epoxy group, were active. Compound 8 was shown to induce apoptosis in the HepG2/ADM cells.
- Yin, Zhi-Qi,Wang, Lei,Li, Cheng-Hua,Zhang, Dong-Mei,Zhang, Wei,Wang, Ying,Zhao, Ming,Che, Chun-Tao,Ye, Wen-Cai
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p. 25765 - 25772
(2017/07/07)
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- New acetylated flavone C-glycosides from Iris lactea
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Chemical investigation of the aerial parts of Iris lactea afforded three new flavone C-glycosides including 4?-O-acetyl-embinin (1), 2?,4?-O-diacetyl-embinin (2) and 6″,4?-O-diacetyl-embinin (3) along with the known analogue embinin (4). Their structures
- Whaley, Andrei K.,Ebrahim, Weaam,El-Neketi, Mona,Ancheeva, Elena U.,?zkaya, Ferhat Can,Pryakhina, Nina I.,Sipkina, Nadezhda U.,Luzhanin, Vladimir G.,Liu, Zhen,Proksch, Peter
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supporting information
p. 2171 - 2173
(2017/05/09)
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- Antibacterial and cytotoxic phenolic metabolites from the fruits of amorpha fruticosa
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Fourteen new natural products, namely, 2-[(Z)- styryl]-5-geranylresorcin-1-carboxylic acid (1), amorfrutin D (2), 4-O-demethylamorfrutin D (3), 8-geranyl-3,5,7- trihydroxyflavanone (4), 8-geranyl-5,7,3′-trihydroxy-4′-methoxyisoflavone (5), 6-geranyl-5,7,3
- Muharini, Rini,Diaz, Adriana,Ebrahim, Weaam,Mándi, Attila,Kurtán, Tibor,Rehberg, Nidja,Kalscheuer, Rainer,Hartmann, Rudolf,Orfali, Raha S.,Lin, Wenhan,Liu, Zhen,Proksch, Peter
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p. 169 - 180
(2017/02/10)
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- Stryphnosides G–P, 10 new triterpene glycosides from the pericarps of Stryphnodendron fissuratum
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Ten new triterpene glycosides, stryphnosides G–P (1–10), were isolated from the pericarps of Stryphnodendron fissuratum (Legminosae). The structures of 1–10 were determined based on spectroscopic analyses, including various two-dimensional NMR spectroscopic techniques, and the results of hydrolytic cleavage. The sugar moiety attached to C-3 of the aglycone of 4, 5, and 7–10 is composed of five or six monosaccharides, of which the terminal α-L-arabinosyl unit has a1C4conformation. Compounds 2 and 5 differ from the other isolates in having an α-L-rhamnosyl unit at the C-21 hydroxy group. The cytotoxic activity of 1–10, stryphnosides A–F (11–16), and their aglycones (1a, 11a, 14a, and 16a) against HL-60?cells was also examined.
- Yokosuka, Akihito,Okabe, Genki,Tatsuno, Satoru,Mimaki, Yoshihiro
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- New isolinariins C, D and E, flavonoid glycosides from Linaria japonica
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Three new flavonoid glycosides named isolinariins C, D and E (1-3), two known flavonoid glycosides (4, 5) and three known flavonoids (6-8) were isolated from the whole plant of Linaria japonica. The structures of these compounds were determined mainly by
- Widyowati, Retno,Sugimoto, Sachiko,Yamano, Yoshi,Sukardiman,Otsuka, Hideaki,Matsunami, Katsuyoshi
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p. 517 - 521
(2016/06/01)
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- Flavonol glycosides from the aerial parts of Gynostemma pentaphyllum and their antioxidant activity
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The phytochemical investigation of the aerial parts of Gynostemma pentaphyllum led to the isolation of a new flavonol glycoside, gynopentaphylloside (1), along with seven known compounds (2–8). The structure of the new compound was determined on the basis of 1D, 2D NMR and HRESIMS data as well as acid hydrolysis. The antioxidant activity of the isolates was evaluated by a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay.
- Jang, Hari,Lee, Jin Woo,Lee, Chul,Jin, Qinghao,Lee, Myung Koo,Lee, Chong Kil,Lee, Mi Kyeong,Hwang, Bang Yeon
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p. 1232 - 1236
(2016/10/03)
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- Trifasciatosides A-J, steroidal saponins from Sansevieria trifasciata
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Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1H-NMR, 13C-NMR, 1H-1H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells.
- Teponno, Rémy Bertrand,Tanaka, Chiaki,Jie, Bai,Tapondjou, Léon Azefack,Miyamoto, Tomofumi
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p. 1347 - 1355
(2016/09/09)
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- A new steroidal saponin from the tubers of ophiopogon japonicus and its protective effect against cisplatin-induced renal cell toxicity
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A new furostanol saponin, ophiopogonin T, was isolated from the tubers of Ophiopogon japonicus. Its structure was established by extensive spectroscopic techniques including 1D (1 H and 13C) and 2D nuclear magnetic resonance (NMR) experiments (correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) and nuclear Overhauser effect spectroscopy (NOESY)), high-resolution electrospray ionization mass spectrometry (ESIMS), and chemical methods. Using cell-based assays, this compound was evaluated for its cytotoxic effect on cancer cell lines and its protective effect against anticancer drug-induced nephrotoxicity. Cisplatin-induced cytotoxicity in porcine kidney (LLC-PK1) cells was significantly reduced upon treatment with ophiopogonin T, without affecting human hepatoma (HepG2) cancer cell proliferation or tube formation in human umbilical vein endothelial cells (HUVECs). These results collectively reflect the beneficial effect of ophiopogonin T on the side effects of cisplatin.
- Lee, Seoung Rak,Han, Ju-Yeon,Kang, Hee Rae,Lee, Hye Lim,Noh, Hyung-Jun,Cha, Jae-Soon,Kang, Ki Sung,Lee, Chan-Jung,Kim, Ki Hyun
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p. 706 - 711
(2016/04/26)
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- Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines
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Seven oleanane-type triterpene saponin bisdesmosides, perennisaponins N–T (1–7), were newly isolated from a methanol extract of daisy, the flowers of Bellis perennis L. (Asteraceae). The structures were determined based on chemical and physicochemical data and confirmed using previously isolated related compounds as references. The isolates, including 13 previously reported perennisaponins A–M (8–20), exhibited anti-proliferative activities against human digestive tract carcinoma HSC-2, HSC-4, and MKN-45 cells. Among them, perennisaponin O (2, IC50?=?11.2, 14.3, and 6.9?μM, respectively) showed relatively strong activities. The mechanism of action of 2 against HSC-2 was found to involve apoptotic cell death.
- Ninomiya, Kiyofumi,Motai, Chiaki,Nishida, Eriko,Kitagawa, Niichiro,Yoshihara, Kazuya,Hayakawa, Takao,Muraoka, Osamu,Li, Xuezheng,Nakamura, Seikou,Yoshikawa, Masayuki,Matsuda, Hisashi,Morikawa, Toshio
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p. 435 - 451
(2016/07/16)
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- Flavonoids from matteuccia struthiopteris and their anti-influenza virus (H1N1) activity
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Seven new flavonoid glycosides (1-7), matteflavosides A-G, together with 12 known flavonoids (8-19) were isolated from the rhizomes of Matteuccia struthiopteris (L.) Todar. Their structures were established via the analyses of extensive spectroscopic data. All compounds were evaluated for their anti-influenza virus (H1N1) activity using the neuraminidase inhibition assay. The results showed that compound 7 exhibited significant inhibitory activity against the H1N1 influenza virus neuraminidase with an EC50 value of 6.8 ± 1.1 μM and an SI value of 34.4, and compounds 8 and 17 showed moderate inhibitory activity.
- Li, Bo,Ni, Yang,Zhu, Ling-Juan,Wu, Feng-Bo,Yan, Fei,Zhang, Xue,Yao, Xin-Sheng
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p. 987 - 995
(2015/06/02)
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- Leptocarposide: A new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)
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A new triterpenoid bidesmoside (leptocarposide) possessing an acyl group in their glycosidic moiety (1), together with the known luteolin-8-C-glucoside (2) and 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(R)-2-hydroxypalmitoylamino]-8- octadecen-1,3- diol (3) was isolated from the n-butanol-soluble fraction of whole plant of Ludwigia leptocarpa (Nutt) Hara (Onagraceae). Structure of compound 1 has been assigned on the basis of spectroscopic data (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC, and ROESY), mass spectrometry, and by comparison with the literature. This compound was further screened for its potential antioxidant properties by using the radical scavenging assay model 2,2-diphenyl-1-picrylhydrazyl and reveals non-potent antioxidant activities, while compound 2 shows SC50 of 0,038 mM.
- Mabou, Florence Declaire,Tebou, Perrin Lanversin Foning,Ngnokam, David,Haraka, Dominique,Voutquenne-Nazabadioko, Laurence
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- α-Rhamnosidase activity in the marine isolate Novosphingobium sp. PP1Y and its use in the bioconversion of flavonoids
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Crude protein extracts of Novosphingobium sp. PP1Y, a microorganism isolated from polluted marine waters in Pozzuoli (Italy), were analyzed for the presence of glycosidase activities. Particular attention was devoted to a α-L-rhamnosidase activity able to hydrolyze several flavonoids of interest for the pharmaceutical and food industries. This activity had an alkaline pH optimum and a moderate tolerance to the presence of organic solvents, appealing features for its possible biotechnological uses. An increase of the α-L-rhamnosidase activity in PP1Y crude extracts was induced by adding naringin to the growth medium, suggesting the possibility to use material from Citrus industrial waste to induce the glycosidase activity expressed by strain PP1Y and produce simultaneously high-added-value molecules from the hydrolysis of their flavonoids. In order to investigate on the enzymatic mechanism of PP1Y α-L-rhamnosidase activity, hydrolysis products of PNP-α-L- rhamnopyranoside were analyzed by 1H-NMR experiments. The kinetic behaviour clearly indicated an inverting mechanism of hydrolysis for this novel enzymatic activity.
- Izzo, Viviana,Tedesco, Pietro,Notomista, Eugenio,Pagnotta, Eduardo,Di Donato, Alberto,Trincone, Antonio,Tramice, Annabella
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- A new cyclic bisdesmoside from Actinostemma lobatum Maxim
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A new cyclic bisdesmoside treterpene saponin, lobatoside N (1), together with four known triterpenoids, was isolated from the herb of Actinostemma lobatum Maxim. Structures were established by means of extensive spectral data analysis. Furthermore, the cytotoxic activities of the identified compounds were evaluated using HCT-116, HT-29, MCF-7 and A549 human cancer cell lines. As a result, compounds 1- 5 showed significant cytotoxicities in a dose-dependent manner against the cell lines tested. Especially, compound 5 exhibited stronger activities, with IC50 value of 0.88μM and 0.98μM, than that of the positive control drug (Cis-platinum) against HT-29 and A549 cell lines.
- Cao, Jiaqing,Wei, Li,Tang, Yun,Li, Ning,Zhao, Yuqing
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p. 347 - 350
(2015/06/16)
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- Triterpenoid saponins from the roots of Clematis uncinata
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Eight new bisdesmosidic triterpenoid saponins, clematiunicinosides A-H (1-8), along with eleven known ones (9-19), were isolated from the roots of Clematis uncinata. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All the isolated saponins were tested for their cytotoxic activities on human caski cervical cancer (Caski) cells, and compounds 13, 17 and 19 exhibited inhibitory effect on Caski cells.
- Li, Shuo-Guo,Huang, Xiao-Jun,Li, Man-Mei,Wang, Mei,Feng, Rui-Bing,Zhang, Wei,Li, Yao-Lan,Wang, Ying,Ye, Wen-Cai
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- Two new glycosides from Duboscia macrocarpa Bocq.
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Two new compounds namely dubosciasides A (1) and B (2) were isolated from stem bark of Duboscia macrocarpa Bocq. together with three known flavonoids. Their structures were determined by spectroscopic methods including one- and two-dimensional NMR, EIMS and HRESIMS. The new compounds were identified as 6-C-β-d-apiofuranosyl-(1 → 4)-β-d-galactopyranosylnaringetol (1) and 1-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-xylopyranosyl-3,4,5-trimethoxyphenol (2).
- Tchuendem, Marguerite H.K.,Douanla, Pascal D.,Tabopda, Turibio K.,Tchinda, Alembert T.,Tamze, Véronique,Nkengfack, Augustin E.,Abegaz, Berhanu M.,Connolly, Joseph D.
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- Triterpenoid saponins from the roots of two Gypsophila species
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Two triterpenoid saponins with two known ones have been isolated from the roots of Gypsophila arrostii var. nebulosa, and two new ones from the roots of Gypsophila bicolor. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranos yl-(1 → 3)]-β-D-glucuronopyranosylquillaic acid 28-O-β-D-xylopyranosyl-(1 →4)-[β-D-glucopyranosyl-(1 →3)]-α-L-rhamnopyranosyl-(1 →2)-[β-D-glucopyranosyl-(1 →4)]-β-D-fucopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosylgypsogenin 28-O-β-D-xylop yranosyl-(1 →4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1 →2)-[β-D-glucopyranosyl-(1 →4)]-β-D-fucopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 →2)-[β-D-xylopyranosyl-(1 →3)]-β-D-glucurono pyranosylgypsogenin 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-D-quinovopyranosyl-(1 →4)]-β-D-fucopyranosyl ester (3), gypsogenic acid 28-O-β-D-glucopyranosyl-(1 →3)-{6-O-[3-hydroxy-3-methylglutaryl]-β-D-glucopyranosyl-(1→6)}-β-D-galactopyranosyl ester (4). Three compounds were evaluated against one human colon cancer cell line SW480 and one rat cardiomyoblast cell line H9c2.
- Pertuit, David,Avunduk, Sibel,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Paululat, Thomas,Delemasure, Stphanie,Dutartre, Patrick,Lacaille-Dubois, Marie-Aleth
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p. 182 - 188
(2015/03/14)
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- Bioactive secondary metabolites from tecomella undulata
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Chromatographic purification of the methanolic extract of Tecomella undulata yielded a new flavonoid glycoside; kaempferol-3-O-β-D-[3 ,4di-p-E -coumaroyl-α-L-rhamnosyl(1→6)] galactoside (1 ), two new megastigmanes; (6R 7Z )-9,10-dihydroxy-4,7-megastigmadien-3-one (2) and (6E )-9,10-dihydroxy-4,6-megastigmadien-3-one (3) along with three known compounds; (6R 9S)-9,10-dihydroxy-4-megastigmaen-3-one (4) quercetin-3-galactoside (5) and 3′-dimethoxy-5,6,4′-trihydroxyflavon (6). All the isolates 1-6 were characterized by the combination of 1D (1H, 13C), 2D (COSY, HSQC and HMBC) NMR data and high resolution mass spectrometric analysis. In antibacterial assay, compound 1 showed moderate inhibitory activity against Escherichia coli and Salmonalla typhi.
- Ahmad, Shabir,Musaddiq, Sara,Saleem, Muhammad,Riaz, Naheed,Fatima, Sundas,Yaqoob, Asma,Jabbar, Abdul,Nasim, Faiz-Ul-Hassan
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p. 1122 - 1128
(2015/01/30)
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- Caspicaosides E-K, triterpenoid saponins and cytotoxic acylated saponins from fruits of Gleditsia caspica Desf.
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Seven bisdesmosidic triterpenoid saponins named caspicaosides E-K, were isolated from the methanolic fruit extract of Gleditsia caspica Desf. Their structures were determined by 1D and 2D NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised echinocystic acid or oleanolic acid as the aglycone and saccharide moieties at C-3 and C-28. Like most Gleditsia saponins, the oligosaccharide moiety at C-3 was identified as β-d-xylopyranosyl-(1→2)-α-l-arabinopyranosyl- (1→6)-β-d-glucopyranosyl. The common oligosaccharide moiety linked to C-28 was determined as β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl- (1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl with the presence of additional β-d-galactopyranose unit and/or another α-l-rhamnopyranose moiety. The C-28 saccharide moiety was acylated with a monoterpenic acid unit or a monoterpenic acid linked to a monoterpene- arabinoside unit at the ester-β-d-glucopyranose C-6. Esterification of C-2 and C-3 hydroxyl groups of the terminal α-l-rhamnopyranose unit with a monoterpenic acid and epoxy-monoterpenic acid units, respectively, or with two identical monoterpenic acid units, was also shown. The acylated saponins caspicaosides G-K were assayed for their in vitro cytotoxicities against the three cell lines HCT116, HepG2 and MCF7. The tested saponins showed moderate to strong activities.
- Melek,Kassem,Miyase, Toshio,Fayad, Walid
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p. 110 - 119
(2014/03/21)
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- METHOD FOR PRODUCING L-FUCOSE
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Method for producing L-fucose includes in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid of a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursor as shown in Formula A, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.
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- Two anti-inflammatory steroidal saponins from Dracaena angustifolia Roxb.
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Two new steroidal saponins, named drangustosides A-B (1-2), together with eight known compounds 3-10 were isolated and characterized from the MeOH extract of Dracaena angustifolia Roxb. The structures of compounds were assigned based on 1D and 2D NMR spectroscopic analyses, including HMQC, HMBC, and NOESY. Compounds 1 and 2 showed anti-inflammatory activity by superoxide generation and elastase release by human neutrophils in response to fMLP/CB.
- Huang, Hui-Chi,Lin, Ming-Kuem,Hwang, Syh-Yuan,Hwang, Tsong-Long,Kuio, Yao-Haur,Chang, Chi-I,Ou, Chung-Yi,Kuo, Yueh-Hsiung
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p. 8752 - 8763
(2013/09/23)
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- Flavone tetraglycosides and benzyl alcohol glycosides from the Mongolian Medicinal plant dracocephalum ruyschiana
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From an extract of the aerial parts of Dracocephalum ruyschiana, five new flavone tetraglycosides, five new benzyl alcohol glycosides, and 19 known compounds were isolated. The tetraglycosides contain a 7-O-β-D- glucopyranosyl-(1→2)-β-D-glucopyranosyl-( 1→2)-[α-L- rhamnopyranosyl-(1→6)]-β-D-glucopyranosyl moiety. The benzyl alcohol glycosides had acyl groups on their glycosyl or aglycone moieties. The compounds were tested for antioxidant activity using DPPH. Although the new compounds were not active, phenylpropanoylquinic acid derivatives were revealed as radical scavengers in D. ruyschiana.
- Selenge, Erdenechimeg,Murata, Toshihiro,Kobayashi, Kyoko,Batkhuu, Javzan,Fumihiko Yoshizaki
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p. 186 - 193
(2013/06/26)
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- Isolation and characterization of dioscin-α-l-rhamnosidase from bovine liver
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A novel dioscin-α-l-rhamnosidase was isolated and purified from fresh bovine liver. The activity of the enzyme was tested using diosgenyl-2,4-di-O- α-l-rhamnopyranosyl-β-d-glucopyranoside as a substrate. It was cleaved by the enzyme to two compounds, rhamnoses and diosgenyl-O-β-d- glucopyranoside. The optimal conditions for enzyme activity were that temperature was at 42 C, pH was at 7, reaction time was at 4 h, and the substrate concentration was at 2%. Furthermore, metal ions such as Fe 3+, Cu2+, Zn2+, Ca2+ and Mg 2+ showed different effects on the enzyme activity. Mg2+ acted as an activator whereas Cu2+, Fe3+, and Zn 2+ acted as strong inhibitors in a wide range of concentrations from 0 to 200 mM. It was interesting that Ca2+ played a role as an inhibitor when its concentration was at 10 mM and acted as an activator at the other concentrations for the enzyme. Moreover, the molecular weight of enzyme was determined as 75 kDa.
- Qian, Siriguleng,Wang, Hongying,Zhang, Chunzhi,Yu, Hongshan
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- Two new monoterpene glycosides from Qing Shan Lu Shui tea with inhibitory effects on leukocyte-type 12-lipoxygenase activity
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We evaluated the inhibitory effect of 12 Chinese teas on leukocyte-type 12-lipoxygenase (LOX) activity. Tea catechins such as epigallocatechin gallate have been known to exhibit leukocyte-type 12-LOX inhibition. Qing Shan Lu Shui, which contains lower catechin levels than the other tested teas, suppressed leukocyte-type 12-LOX activity. To characterize the bioactive components of Qing Shan Lu Shui, leukocyte-type 12-LOX inhibitory activity-guided fractionation of the aqueous ethanol extract of the tea was performed, resulting in the isolation of two new monoterpene glycosides: liguroside A (1) and B (2). The structures of compounds 1 and 2 were characterized as (2E,5E)-7- hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(α-L-rhamnopyranosyl) -(1 →3')-(4' -O-transp- coumaroyl)-β-D-glucopyranoside and (2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl- O-(α-L- rhamnopyranosyl)-(1 →3')-(4' -O-cis-p-coumaroyl) -β-D-glucopyranoside, respectively, based on spectral and chemical evidence. Ligurosides A (1) and B (2) showed inhibitory effects on leukocyte-type 12-LOX activity, with IC50 values of 1.7 and 0.7 μM, respectively.
- Ito, Hideyuki,Otsuki, Akemi,Mori, Hitomi,Li, Peng,Kinoshita, Mai,Kawakami, Yuki,Tsuji, Hideaki,Fang, Ding Zhi,Takahashi, Yoshitaka
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p. 4257 - 4266
(2013/06/26)
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- Triterpenoid saponins of pulsatilla koreana root have inhibition effects of tumor necrosis factor-α secretion in lipopolysaccharide-induced RAW264.7 cells
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In the present study, a new oleanane-type triterpenoid saponin, pulsatilloside F (1), along with 21 known compounds (2-22), were isolated from the root of Pulsatilla koreana. Their chemical structures were elucidated by mass, 1H-, 13C-NMR, correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) spectroscopy. Anti-inflammatory effects of the compounds were evaluated in terms of inhibitory of tumor necrosis factor a (TNF-α) secretion in the lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cell line. Compounds 19 and 20 exhibited particularly inhibitory effects with respective IC50 values of 0.32 and 0.65 μm. Compounds 1-4, 7 and 10-13 exhibited inhibitory effects with inhibition rates up to 41.55-73.76% at a concentration of 5 μm, respectively.
- Li, Wei,Ding, Yan,Sun, Ya Nan,Yan, Xi Tao,Yang, Seo Young,Choi, Chun Whan,Cha, Ji Yun,Lee, Young Mi,Kim, Young Ho
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p. 471 - 476
(2013/06/05)
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- A new flavonoidal constituent from taraxacum officinale (L.) weber
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A new flavone glycoside (A) m.p. 265-268 °C, m.f. C33H 40O21, [M]+ 742 (FABMS), has been isolated from stem of Taraxacum oficinale (L.) Weber. It was characterized as 3,5,7,3',4'-pentahydroxy 8-C methyl flavone 7-O-β-D-xylopyranosyl (14)O-β-D glucopyranosyl 3'- O-α-L-rhamnopyranoside alongwith known compound ladanein B by various chemical degradations and spectral analysis.
- Yadava, Raj Nath,Khan, Shirin
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p. 4117 - 4118
(2013/06/05)
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- METHOD FOR PRODUCING L-FUCOSE
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The present invention provides: in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid or a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursoras shown in Formula A below, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.
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- Medicinal flowers. XXXV. Nor-oleanane-type and acylated oleanane-type triterpene saponins from the flower buds of Chinese Camellia japonica and their inhibitory effects on melanogenesis
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The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia japonica, cultivated in Yunnan Province, China, showed inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the 1-butanol-soluble fraction, a new 28-nor-oleanane-type and three new oleanane-type triterpene saponins, sanchakasaponins A-D, were isolated together with four known triterpene saponins. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells and structure-activity relationships of the saponins were investigated.
- Fujimoto, Katsuyoshi,Nakamura, Seikou,Nakashima, Souichi,Matsumoto, Takahiro,Uno, Kaoru,Ohta, Tomoe,Miura, Tomoko,Matsuda, Hisashi,Yoshikawa, Masayuki
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p. 1188 - 1194,7
(2020/08/31)
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- Eastern blotting analysis and isolation of two new dammarane-type saponins from American ginseng
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Ginsenosides, the major active component of American ginseng, were analyzed using eastern blotting with anti-ginsenoside Rb1 and Rg1 monoclonal antibodies (MAbs). Immunoassay-guided fractionation of the methanol extract of American g
- Tung, Nguyen Huu,Shoyama, Yukihiro
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p. 1329 - 1333,5
(2020/09/09)
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- Saponins with neuroprotective effects from the roots of Pulsatilla cernua
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Four new oleanene-type triterpenoid saponins together with six known saponins were isolated from the roots of Pulsatilla cernua and their structures were elucidated on the basis of spectroscopic data, including 2D NMR spectra and chemical evidence. Among
- Liu, Jian-Yu,Guan, Ying-Li,Zou, Li-Bo,Gong, Yi-Xia,Hua, Hui-Ming,Xu, Yong-Nan,Zhang, Hui,Yu, Zong-Gui,Fan, Wen-Hao
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experimental part
p. 5520 - 5531
(2012/09/22)
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- Two new triterpenoid glycosides from Curculigo orchioides
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Two new cycloartane triterpenoid glycosides, named curculigosaponin N and curculigosaponin O, were isolated from rhizomes of Curculigo orchioides Gaertn. Their structures were elucidated on the basis of comprehensive spectroscopic analysis including IR, M
- Zuo, Ai-Xue,Shen, Yong,Jiang, Zhi-Yong,Zhang, Xue-Mei,Zhou, Jun,Lue, Jun,Chen, Ji-Jun
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experimental part
p. 407 - 412
(2012/08/28)
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- Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β- glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside
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Transglycosylation potential of the fungal diglycosidase α-rhamnosyl-β-glucosidase was explored. The biocatalyst was shown to have broad acceptor specificity toward aliphatic and aromatic alcohols. This feature allowed the synthesis of the diglycoconjugated fluorogenic substrate 4-methylumbelliferyl-rutinoside. The synthesis was performed in one step from the corresponding aglycone, 4-methylumbelliferone, and hesperidin as rutinose donor. 4-Methylumbelliferyl-rutinoside was produced in an agitated reactor using the immobilized biocatalyst with a 16% yield regarding the sugar acceptor. The compound was purified by solvent extraction and silica gel chromatography. MALDI-TOF/TOF data recorded for the [M+Na]+ ions correlated with the theoretical monoisotopic mass (calcd [M+Na]+: 507.44 m/z; obs. [M+Na]+: 507.465 m/z). 4-Methylumbelliferyl-rutinoside differs from 4-methylumbelliferyl-glucoside in the rhamnosyl substitution at the C-6 of glucose, and this property brings about the possibility to explore in nature the occurrence of endo-β-glucosidases by zymographic analysis.
- Mazzaferro, Laura S.,Pi?uel, Lucrecia,Erra-Balsells, Rosa,Giudicessi, Silvana L.,Breccia, Javier D.
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scheme or table
p. 69 - 75
(2012/02/05)
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- Flavonol glycosides from Chenopodium foliosum Asch
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Three new flavonol glycosides, namely 6-methoxykaempferol-3-O-β- gentiobioside, gomphrenol-3-O-β-gentiobioside and gomphrenol-3-O-α-l- rhamnopyranosyl-(1 → 2)[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranoside as well as the known patuletin-3-O-β- gentiobioside and spinacetin-3-O-β-gentiobioside were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR, and HRMS). DPPH free radical scavenging activity of the new compounds was low or lacking.
- Kokanova-Nedialkova, Zlatina,Bücherl, Daniel,Nikolov, Stefan,Heilmann, J?rg,Nedialkov, Paraskev T.
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experimental part
p. 367 - 371
(2012/05/04)
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- Soyasaponins from soybean flour medium for the liquid culture of ganoderma applanatum
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Two new unusual soyasaponins named 6''-O-methyldehydrosoyasaponin I (7) and desglucosylsoyasaponin A1 (10) along with eight known saponins, dehydrosoyasaponin IV (1), dehydrosoyasaponin III (= impatienoside A) (2), soyasaponin III (3), dehydrosoyasaponin II (= soyasaponin Bg) (4), soyasaponin II (5), dehydrosoyasaponin I (= soyasaponin Be) (6), soyasaponin I (8), and kudzusaponin SA3 (9), were isolated as their methyl esters and identified from the liquid culture of G. applanatum. Their structures were determined by chemical and spectroscopic analyses including 1D- and 2D-NMR as well as by comparison of their spectroscopic data with those of the reported in literatures. Although dehydrosoyasaponin IV was identified by LC-MS/MS method from soy protein isolate, this is the first report of the isolation of this compound. Dehydrosoyasaponin III (2) and kudzusaponin SA3 (9) were also isolated for the first time from soybean. The presence of soyasaponins in Ganoderma species seems to be unusual feature. Thus, we presumed that compounds 1-10 might all be derived from the defatted soybean flour which was added to the culture medium as a nitrogen source.
- Lee, So Young,Kim, Ju Sun,Shim, Sang Hee,Kang, Sam Sik
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experimental part
p. 3650 - 3654
(2012/01/11)
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