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紫杉醇及相关紫杉烷。I. 短叶红豆杉树皮中的紫杉烷。

Taxol and related taxanes. I. Taxanes of Taxus brevifolia bark.

作者信息

Rao K V

机构信息

University of Florida, College of Pharmacy, Department of Medicinal Chemistry, Gainesville 32610-0485.

出版信息

Pharm Res. 1993 Apr;10(4):521-4. doi: 10.1023/a:1018937700459.

DOI:10.1023/a:1018937700459
PMID:8097872
Abstract

The published procedures for the isolation of taxol from the Pacific yew (Taxus brevifolia) and other species of Taxus are cumbersome, and the yields of taxol are in the range of 0.0075-0.01%. This paper describes a simple and efficient procedure for the isolation of taxol and its major natural analogues from the bark of T. brevifolia consisting of a single chromatographic column (using silica gel, Florisil, or a reverse-phase C18-silica), followed by crystallization. Isolated yields of taxol from five "pooled" bark samples (blended from many different batches by the supplier) were in the range of 0.02-0.04%, and from bark collected from a more restricted locale, yields reached 0.06%. The procedure also yielded taxol analogues, such as 10-deacetylbaccatin III (0.02-0.04%), 10-deacetyltaxol-7-xyloside (0.06-0.1%), taxol-7-xyloside (0.005-0.01%), 10-deacetyltaxol (0.01-0.02%), 10-deacetylcephalomannine-7-xyloside (0.006-0.01%), and cephalomannine (0.005-0.007%). Of these, 10-deacetyltaxol-7-xyloside is the most abundant taxane in the Pacific yew bark.

摘要

已发表的从太平洋紫杉(短叶红豆杉)及其他红豆杉属物种中分离紫杉醇的方法很繁琐,紫杉醇的产率在0.0075 - 0.01%之间。本文描述了一种从短叶红豆杉树皮中分离紫杉醇及其主要天然类似物的简单高效方法,该方法包括单个色谱柱(使用硅胶、弗罗里硅土或反相C18硅胶),随后进行结晶。从五个“混合”树皮样品(由供应商从许多不同批次混合而成)中分离得到的紫杉醇产率在0.02 - 0.04%之间,而从更有限区域采集的树皮中,产率达到了0.06%。该方法还得到了紫杉醇类似物,如10 - 去乙酰浆果赤霉素III(0.02 - 0.04%)、10 - 去乙酰紫杉醇 - 7 - 木糖苷(0.06 - 0.1%)、紫杉醇 - 7 - 木糖苷(0.005 - 0.01%)、10 - 去乙酰紫杉醇(0.01 - 0.02%)、10 - 去乙酰三尖杉宁碱 - 7 - 木糖苷(0.006 - 0.01%)和三尖杉宁碱(0.005 - 0.007%)。其中,10 - 去乙酰紫杉醇 - 7 - 木糖苷是太平洋紫杉树皮中含量最丰富的紫杉烷。

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Taxol and related taxanes. I. Taxanes of Taxus brevifolia bark.紫杉醇及相关紫杉烷。I. 短叶红豆杉树皮中的紫杉烷。
Pharm Res. 1993 Apr;10(4):521-4. doi: 10.1023/a:1018937700459.
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本文引用的文献

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A new large-scale process for taxol and related taxanes from Taxus brevifolia.一种从短叶红豆杉中提取紫杉醇及相关紫杉烷的新大规模工艺。
Pharm Res. 1995 Jul;12(7):1003-10. doi: 10.1023/a:1016206314225.
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Taxol: a unique antineoplastic agent with significant activity in advanced ovarian epithelial neoplasms.紫杉醇:一种对晚期卵巢上皮性肿瘤具有显著活性的独特抗肿瘤药物。
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Taxus spp. needles contain amounts of taxol comparable to the bark of Taxus brevifolia: analysis and isolation.红豆杉属植物的针叶中紫杉醇的含量与短叶红豆杉的树皮相当:分析与分离。
J Nat Prod. 1990 Sep-Oct;53(5):1249-55. doi: 10.1021/np50071a017.
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Promotion of microtubule assembly in vitro by taxol.紫杉醇在体外促进微管组装。
Nature. 1979 Feb 22;277(5698):665-7. doi: 10.1038/277665a0.