Productions of taxol and related taxanes by cell suspension cultures of Taxus yunnanensis
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A high taxol yield cell line of Taxus yunnanensis Cheng et L. K. Fu keeps a high taxol-producing level after successive subcultures for more than eight years. In this study, eight taxanes were isolated from the suspension cell cultures of this cell line. Based on NMR and MS analyses, and comparison with literature data and standards, their structures were determined to be 2alpha, 5alpha, 10beta-triacetoxy-14beta-proplonyloxy-4(20), 11-taxadiene (1), 2alpha, 5alpha, 10beta-triacetoxy-14beta-(2'-methyl)-butyryloxy-4(20), 11-taxadiene (2), 2alpha, 5alpha, 10beta-14beta-tetra-acetoxy-4 (20), 11-taxadiene (3, taxuyunnanine C), 2alpha, 5alpha, 10beta-triacetoxy-14beta-(2'-methyl-3'-hydroxy)-butyryloxy-4(20), 11-taxadiene (4, yunnanxane) and its 3'-epimer (5), baccatin IV (6), baccatin III (7) and taxol (8), respectively. Among those compounds, 3, 5, 6 and 7 were reported to be isolated from the suspension cell cultures of T. yunnanensis for the first time. TLC and HPLC analyses indicated that the chemical constituents of the culture solution were similar to those of cultured cells. Moreover, the highest taxol content of this cell line reached 0.3% and the cell line could be applied for a large-scale culture.Keywords:
Suspension culture
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Abstract Nineteen compounds including taxumairol R (1) , taxinine M (2) , taxacin (3) , paclitaxel (4) , 10‐deacetyltaxol A (5) , 10‐deacetyl‐7‐ epi ‐taxol (6) , 7‐ epi ‐taxol (7) , taxol C, 10‐deacetyltaxol C, 7β‐xylosyl‐10‐deacetyltaxol (8) , taxamairin A (9) , taxinine A, 14β‐hydroxytaxusin (10) , 5α‐hydroxy‐7β,9α,10β, 13α‐tetraacetoxy‐4(20), 11‐taxadiene, 1‐dehydroxybaccatin‐VI, 1β‐dehydroxybaccatin‐IV, baccatin IV, baccatin VI and ponasterone A have been isolated and identified from the root bark of Taxus mairei . Among them, compound 1 was a new taxoid and compounds 11 and 7β‐xylosyl‐10‐deacetyltaxol pentaacetate were new derivatives prepared from 14β‐hydroxytaxusin (10) and 8 , respectively. Their structures and assignment were established on the basis of 2D‐NMR analysis and chemical methods.
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A new 2(3→20) abeotaxane, taxumairone A (1), and a new cis-p-coumaroyl myo-inositol have been isolated from the seeds of Taxus mairei in addition to taxin B (2), taxinine A, taxuspine X, decinnamoyltaxinine E, 5α-cinnamoyloxy-9α, 10β, 13α-triacetoxy-taxa-4(20)11-diene and 5α-cinnamoyloxy-2α, 9α, 10β, 13α-tetraacetoxy-taxa-4(20)11-diene. The structure of 1 was determined by 2D-NMR spectral analysis and chemical correlation with taxin B (2). Compound 1 exhibited potent cytotoxicity against human colon carcinoma cells with an ED50 of 0.1 μg/ml.
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Abstract Two new taxanes-1-hydroxy-5-decinnamoyl taxinine J (1) and 1-hydroxy taxinine A (2), and seven known taxanes were isolated using silica gel chromatography from the needles of Taxus x. media Hicksii. Their structures were primarily determined by detailed spectroscopic analysis. The known compounds have been characterized as taxol (3), cephalomannine (4), baccatin III (5), taxinine (6), taxinine M (7), 1-hydroxy-5-deacetyl baccatin I (8) and taxyuntin (9).
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A new C-14 oxygenated taxoid,14β-hydroxy-baccatin VI (1),together with seven known taxoids,baccatin VI (2),baccatin IV (3),1β-dehydroxybaccatin IV (4),taxayunnasin A (5),2α-deacetyl-2α-benzoyl-13α-acetyltaxayuntin (6),5α-hydroxy-2α,7β,9α,10β,13α-pentaacetoxy-4 (20),11-taxadiene (7) and taxacin (8) were isolated from the ethanolic extract of leaves and stems of Taxus chinensis (Pilg) Rehd.The structures of the compounds were elucidated by spectroscopic techniques.The detailed 13C and 1H NMR data of the seven known compounds were measured in acetone-d 6,and the NMR data of taxacin (8) were reported for the first time.
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Five compounds were isolated from the bark of Taxus yunnanensis. Their structures were identified on the basis of spectral analysis and physico-chemical constants as taxol C-7-xylose, taxol B, 10-deacetyl baccatin III, taxusin and 2R,3R-catechin.
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AIM Taxane diterpenoid compounds are expected to be isolated from Taxus chinensis cell cultures. METHODS Cell cultures were extracted with 95% alcohol, distributed by different solvents, isolated via column chromatography on silica gel and purified by crystallization. RESULTS AND CONCLUSION Two taxane diterpenoid compounds were isolated from Taxus chinensis cell cultures for the first time.Their structures were identified as 14β (2 methylbutyryl)oxy 2α,5α, 10β triacetoxytaxa 4(20),11 diene(1) and 5α (cinnamoyl)oxy 7β,9α,10β,13α tetraacetoxytaxa 4(20),11 diene(2) respectively.
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Two 11(15-->1)abeotaxanes having a tetrahydrofuran ring along the carbon atoms C-2, C-3, C-4, C-20 were identified for the first time from the needles of the Canadian yew, Taxus canadensis. The compounds could be identified as 4alpha,10beta,13alpha-triacetoxy-15-benzoyloxy-2alpha,20beta-epoxy-11(15-->1)abeotax-11-ene-5alpha,7beta,9alpha-triol (1) and 4alpha,7beta,9alpha,10beta,15-pentaacetoxy-2alpha,20beta-epoxy-11(15-->1)abeotax-11-ene-5alpha,13alpha-diol (2) on the basis of 1D-, 2D-NMR evidence and high-resolution FABMS analysis. Compound 1 showed weak growth inhibitory activities against T-98 and MM1-CB cells in vitro.
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Objective To investigate the chemical constituents of a callus culture of Taxus cuspidata.Methods The compounds were isolated and purified from n-hexane and ethyl acetate extracts of the callus culture by silica gel column chromatography and preparative HPLC,and their chemical structures were confirmed by analysis of the physico-chemical constants and spectral data.Results Eleven taxoids were obtained and identified as taxuyunnanine C(1),2α,5α,10β-triacetoxy-14β-propionyloxy-4(20),11-taxadiene(2),2α,5α,10β-triacetoxy-14β-isobutyryloxy-4(20),11-taxadiene(3),2α,5α,10β-triacetoxy-14β-(2′-methyl)butyryloxy-4(20),11-taxadiene(4),yunnanxane(5),paclitaxel(6),taxol C(7),baccatin VI(8),1β-deoxybaccatin VI(9),taxayuntin C(10),and baccatin I(11),respectively.Conclusions Compounds 9 and 11 are reported from the callus culture of T.cuspidata for the first time,and compounds 14,810 are firstly isolated from the plant.
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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTYunnanxane and Its Homologous Esters from Cell Cultures of Taxus chinensis var. maireiWenwen Ma, Roy W. Stahlhut, Tom L. Adams, Gary L. Park, William A. Evans, Sibylle G. Blumenthal, George A. Gomez, Matthew H. Nieder, and Peter J. HylandsCite this: J. Nat. Prod. 1994, 57, 9, 1320–1324Publication Date (Print):September 1, 1994Publication History Published online1 July 2004Published inissue 1 September 1994https://pubs.acs.org/doi/10.1021/np50111a027https://doi.org/10.1021/np50111a027research-articleACS PublicationsRequest reuse permissionsArticle Views134Altmetric-Citations27LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
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