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italic>Tripterygium wilfordii Hook. f. is a valuable medicinal plant, with anti-tumor, anti-inflammatory, immunosuppressive and other pharmacological activities. Triterpenoids are one of the main active components that exert pharmacological effects. However, the content of triterpenoids dominated by triptolide is very low in Tripterygium wilfordii, and the analysis of the biosynthetic pathway of triterpenoids in Tripterygium wilfordii provides an effective new idea for obtaining these compounds. 2,3-Oxidosqualene cyclases (OSCs) are the key enzyme that catalyzes the formation of triterpene skeleton diversity. Based on the genome and transcriptome data of Tripterygium wilfordii, 16 OSC genes were identified and analyzed. Phylogenetic analysis showed that 16 TwOSC proteins could be mainly classified as four groups. They are β-amyrin synthase group, friedelin synthase group, multifunctional amyrin synthase and cycloartenol synthase group. TwOSC6 was successfully cloned. Functional characterization analysis revealed that TwOSC6 can catalyze the formation of α-amyrin and β-amyrin. This indicates that TwOSC6 is a multifunctional amyrin synthase. This provides new gene resources for the diversity of Tripterygium wilfordii triterpenoids, as well as new gene elements for biosynthesis triterpenoids.
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Triterpenoids have been described in Andrographis paniculata. Oleanolic acid exhibits high biological activity and is widely used in the clinic, and β-sitosterol not only has good biological activity but also plays an important physiological role in plants. However, analysis of the biosynthetic pathway of triterpenoids in Andrographis paniculata has not been reported. Here, we provide the first report of the isolation and identification of nine 2, 3-oxidosqualene cyclases (ApOSC3 to ApOSC11) from A. paniculata. The results showed that ApOSC4 represented a monofunctional synthase that could convert 2, 3-oxidosqualene to β-amyrin. ApOSC5 as a bifunctional 2, 3-oxidosqualene cyclases, could transfer 2, 3-oxidosqualene to β-amyrin and α-amyrin. ApOSC6 to ApOSC8 composed the multifunctional 2, 3-oxidosqualene cyclases that could convert 2, 3-oxidosqualene to β-amyrin, α-amyrin and one or two undetermined triterpenoids. This study provides a better understanding of the biosynthetic pathway of triterpenoids in A. paniculata, and the discovery of multifunctional 2, 3-oxidosqualene cyclases ApOSC5 to ApOSC8 of the facilitates knowledge of the compounds diversity in A. paniculata.
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Objective To study the chemical constituents from Achyrocline satureioides. Methods Chemical constituents from A. satureioides were separated and purified by a variety of chromatographic techniques, and their structures were identified by various spectroscopic methods. Results Twenty-one compounds were isolated from ethyl acetate fraction of the plant, which were α-amyrin (1), ergosta-4,6,8,22-tetraene-3-one (2), (R)-24-ethylcholest-4-en-3,6-dione (3), clovandiol (4), caryolane-1,9β-diol (5), lepidissipyrone (6), 5,7-dihydroxy-3,6-dimethoxyflavone (7), quercetin-7-O-β-D-glucoside (8), pinocembrin (9), (2R,3R)-taxifolin (10), quercetin-4’-O-β-D-glucoside (11), helichrysetin (12), 3-[5,7-dihydroxy-2,2-dimethyl-8-(2-(S)-methyl-butanoyl)-2H-chromen-6- yl-methyl]-6-ethyl-4-hydroxy-5-methyl-pyran-2-one (13), quercetin (14), protocatechuic acid (15), (+)-(3R)-3-hydroxyl-4,4- dimethyl-4-butyrolactone (16), (4S,5R)-5-(4’-methyl-3’-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one (17), genkwanin (18), quercetin-3-methyl ether (19), galangin (20), and neosakuranin (21). Conclusion Compounds 1, 4, 5, 16, 17, and 21 are obtained from the genus for the first time, and compounds 1-12, 16-18, and 21 are obtained from the plant for the first time.
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Objective To study the chemical constituents from the roots of Ligularia veitchiana. Methods Some chromatographic methods were used to isolate the chemical constituents from the roots of L. veitchiana, their structures were elucidated on the basis of spectral data. Results Six compounds were isolated from roots of L. veitchiana and were identified as liguveitoside B (1), oleanolic acid (2), β-sitosterol (3), α-amyrin (4), α-amyrin-3-O-β-D-glucopyranoside (5), and β-daucosterol (6). Conclusion Compound 1 is a new compound, named liguveitoside B; Compounds 4 and 5 are isolated from L. veitchian for the first time.
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Objective To study chemical constituents from the flowers of Chrysanthemum indicum. Methods The chemical constituents of C. indicum were isolated and purified by various chromatographic techniques, including thin-layer chromatography, silica gel, ODS reversed-phase silica gel, and Sephadex LH-20 for column chromatography, and their structures were identified by NMR spectral analysis. Results Fourteen compounds were isolated and identified as stigmata-4-ene-3-one (1), calenduladiol-3β-O- palmitate (2), 16β,22α-dihydroxypseudotaraxasterol-3β-O-palmitate (3), α-amyrin (4), urs-12-ene-3β,16β-diol (5), 3β-hydroxyurs- 12-ene-11-one (6), arnidiol (7), maniladiol (8), 3β-hydroxyolean-12-ene-11-one (9), luteolin (10), apigenin (11), apigenin-7,4’- dimethyl ether (12), genkwanin (13), and 1-linoleic acid glycerate (14). Conclusion Compounds 1-6, 10-12, and 14 are isolated from the flowers of C. indicum for the first time.
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Considering the great potential of natural products as anticancer agents, the present study was designed to explore the molecular mechanisms responsible for anticancer activities of Mesua ferrea stem bark extract against human colorectal carcinoma. Based on MTT assay results, bioactive sub-fraction (SF-3) was selected for further studies using HCT 116 cells. Repeated column chromatography resulted in isolation of less active α-amyrin from SF-3, which was identified and characterized by GC-MS and HPLC methods. α-amyrin and betulinic acid contents of SF-3 were measured by HPLC methods. Fluorescent assays revealed characteristic apoptotic features, including cell shrinkage, nuclear condensation, and marked decrease in mitochondrial membrane potential in SF-3 treated cells. In addition, increased levels of caspases-9 and -3/7 levels were also observed in SF-3 treated cells. SF-3 showed promising antimetastatic properties in multiple in vitro assays. Multi-pathway analysis revealed significant down-regulation of WNT, HIF-1α, and EGFR with simultaneous up-regulation of p53, Myc/Max, and TGF-β signalling pathways in SF-3 treated cells. In addition, promising growth inhibitory effects were observed in SF-3 treated HCT 116 tumour spheroids, which give a hint about in vivo antitumor efficacy of SF-3 phytoconstituents. In conclusion, these results demonstrated that anticancer effects of SF-3 towards colon cancer are through modulation of multiple molecular pathways.
Subject(s)
Humans , Antineoplastic Agents , Pharmacology , Apoptosis , Cell Line, Tumor , Colorectal Neoplasms , Drug Therapy , Metabolism , Pathology , ErbB Receptors , Genetics , Metabolism , HCT116 Cells , Hypoxia-Inducible Factor 1, alpha Subunit , Genetics , Metabolism , Magnoliopsida , Chemistry , Neoplasm Metastasis , Plant Bark , Chemistry , Plant Extracts , Pharmacology , Signal Transduction , Wnt Proteins , Genetics , MetabolismABSTRACT
Objective: To investigate the chemical constituents of the flowers of Gentiana dahurica. Methods: All compounds were isolated and purified by silica gel, Sephadex LH-20, ODS, and MCI column chromatography. Their structures were determined by physicochemical properties and spectral data. Results: Twenty compounds were isolated from the flowers of G. dahurica. Among them, eight triterpenoids were identified as roburic acid (1), 3β-acetoxy-28-hydroxy-12-ene-oleanane (2), 28-hydroxy-α-amyrin (3), 28-hydroxy-β-amyrin (4), α-amyrin (5), β-amyrin (6), ursolic acid (7), and oleanolic acid (8). Twelve flavonoids were identified as 1-hydroxy-3,7,8-trimethoxyxanthone (9), kaempferol (10), naringenin (11), apigenin (12), luteolin (13), (2S)-naringenin-7-O-β-D- glucopyranoside (14), apigenin-7-O-β-D-glucopyranoside (15), luteolin-7-O-β-D-glucopyranoside (16), isoorientin (17), isovitexin (18), saponarin (19), and lutonarin (20). Conclusion: Seventeen compounds 1-11, 13-16, 19, and 20 are found from flowers of G. dahurica for the first time; Compounds 2-7, 9-11, 13-16, 19, and 20 are isolated from this species for the first time.
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Objective: To study the chemical constituents from the branches and leaves of Viburnum sargentii collected at Mountain Tai. Methods: The chemical constituents were isolated and purified by chromatographic methods, including silica gel, ODS, Sephadex LH-20 columns, and RP HPLC. The structures of the isolated compounds were identified by ESI-MS, 1D-NMR, and 2D-NMR data analyses, and compared with the literature data. Results: Thirteen compounds were obtained from the 95% ethanol extract of branches and the leaves of V. sargentii, and determined as α-amyrin (1), uvaol (2), 3α-ursolic acid (3), 11,12-dehydroursolic acid lactone (4), 3-O-acetyloleanolic aldehyde (5), oleanolic acid (6), betulinic acid (7), magnolin (8), (+)-eudesmin (9), (-)-epieudesmin (10), vibsanol (11), 3,4'-dimethoxylvibsanol (12), and α-asarone (13), respectively. Conclusion: Compound 12 (3,4'- dimethoxylvibsanol) is a new natural product, and compounds 1-11 and 13 are isolated from V. sargentii for the first time.
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Chemical investigation of the dichloromethane extracts of Hoya diversifolia Blume led to the isolation of β-amyrin cinnamate (1), squalene (2), β-sitosterol (3), a mixture of β-amyrin (4a), α-amyrin (4b) and lupeol (4c) in a 4:2:1 ratio and saturated hydrocarbons from the leaves; and 2, taraxerol (5), lupeol cinnamate (6), and a mixture of 3 and stigmasterol (7) in a 2:1 ratio from the stems. The structures of 1-7 were identified by comparison of their NMR data with those reported in the literature.
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Objective: To study the chemical constituents from Gnaphalium affine and their anti-oxidative activities. Methods: Chemical constituents were isolated by column chromatography and semi-prepared HPLC, the structures were elucidated by spectral data and physicochemical properties. DPPH free radical scavenging activities of compounds 1,3-11, and 16 were determined. Results: Seventeen compounds were isolated and respectively identified as apigenin (1), dihydroapigenin (2), luteolin (3), chrysin (4), wogonin (5), stimasterol (6), β-sitosterol (7), ursolic acid (8), oleanolic acid (9), 19α-hydroxyl-oleanolic acid (10), 2α, 3α, 19α-trihydroxy-28-norurs-12ene (11), α-amyrin acetate (12), β-amyrin acetate (13), patriscabratine (14), aurantiamide acetate (15), 4'-hydroxydehydrokawain (16), and isovanillin (17). Compounds 1 and 3-5 had significant anti-oxidative activities. Conclusion: Compounds 2,4,5,11-15, and 17 are isolated from G. affine for the frist time.
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Chemical investigation of the dichloromethane extracts of Hoya buotii Kloppenb. afforded taraxerone (1), taraxerol (2), a mixture of β-sitosterol (3a) and stigmasterol (3b) in about 2:1 ratio, and a mixture of α-amyrin cinnamate (4a) and β-amyrin cinnamate (4b) in about 1:2 ratio from the stems; 1, 2, and 3a from the roots; a mixture of 4a and 4b in about 3:2 ratio from the flowers; and 3a, squalene (5) and saturated hydrocarbons from the leaves. The structures of 1-5 were identified by comparison of their NMR data with those reported in the literature.
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Chemical investigations of the dichloromethane extracts of the leaves of Canarium ovatum Engl. afforded β- amyrin (1a), α-amyrin (1b), epi-β-amyrin (2a), epi-α-amyrin (2b), epi-lupeol (2c), β-carotene (3) and lutein (4); while the twigs yielded 1a-1b. The dichloromethane extracts of the fruits of C. ovatum yielded triacylglycerols (5); the mesocarp also afforded 1a, 1b, 1,2-dioleylglycerol (6), and monounsaturated and saturated fatty acids; the nutshell also provided 6; and the kernel also yielded monounsaturated and saturated fatty acids. The structures of 1-6 and the fatty acids were identified by comparison of their 1H and/or 13C NMR data with those reported in the literature.
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Chemical investigation of the dichloromethane extracts of Hoya multiflora Blume led to the isolation of lupeol (1a), α-amyrin (1b), β-amyrin (1c), lupeol acetate (2a), α-amyrin acetate (2b), and β-amyrin acetate (2c) from the stems; and 1b, bauerenol (3), squalene (4), lutein (5), β-sitosterol (6a), and stigmasterol (6b)from the leaves. The structures of 1-6 were identified by comparison of their 1H and/or13C NMR data with those reported in the literature.
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Objective: To study the chemical constituents from the roots of Ficus auriculata. Methods: The chemical constituents were isolated and purified by various chromatographic methods, including silica gel, ODS, Sephadex LH-20 columns, and recrystallization. Structures of the isolated compounds were elucidated based on NMR and ESI-MS data, as well as physicochemical properties. Results: Thirteen compounds were obtained in the EtOAc fraction of ethanol extract from the roots of F. auriculata and identified as β-sitosterol (1), α-amyrin (2), 6β-hydroxystigmast-4-en-3one (3), stigmasta-3, 6-dione (4), (22E, 24S)-24-methyl-5α- choleata-7, 22-diene-3β, 5, 6β-triol (5), 3-(1-hydroxyethyl)-7-hydroxy-1-isobenzofuranone (6), (R)-(+)-de-O-methyllasiodiplodin (7), decursinol (8), (-)-3, 5-dimethyl-8-methoxy-3, 4-dihydroisocoumarin (9), (R)-(-)-mellein methyl ether (10), 5-formyl-8-hydroxy-3, 4-dihydroisocoumarin (11), (R)-(-)-5-methoxycarbonyl mellein (12), and β-daucosterol (13). Conclusion: All the compounds except compound 1 are firstly isolated from F. auriculata, and compounds 4-12 are found in the plants of Ficus Linn. for the first time.
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A new triterpene ester,α-amyrin caffeate(1),was isolated from the seeds of Impatiens balsamina L.