Abstract
Three new C-14 oxygenated taxane-type diterpenes, hongdoushans A-C (1-3), were isolated from the wood of Taxus yunnanensis together with four known diterpenes and two lignans. The absolute stereochemistry of the 2-methylbutyryloxy group attached at C-14 of the taxane skeleton was determined to be S by GC analysis of the methyl ester of 2-methylbutyric acid obtained after alkaline hydrolysis of 1 and 4 followed by treatment with CH(2)N(2). The complete stereostructure of the known compound 2alpha,5alpha,10beta-triacetoxy-14beta-[(S)-2-methylbutyryloxy]-4(20),11-taxadiene (4) was established for the first time. The isolates obtained were evaluated for their antiproliferative activity toward murine colon 26-L5 carcinoma and human HT-1080 fibrosarcoma cell lines.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology
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Bridged-Ring Compounds / chemistry
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Bridged-Ring Compounds / isolation & purification*
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Bridged-Ring Compounds / pharmacology
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Cell Survival / drug effects
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Colonic Neoplasms
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Diterpenes / chemistry
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Diterpenes / isolation & purification*
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Diterpenes / pharmacology
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Drug Screening Assays, Antitumor
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Drugs, Chinese Herbal / chemistry*
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Fibrosarcoma
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Humans
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Hydrolysis
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Mice
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Paclitaxel / analogs & derivatives
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Plants, Medicinal / chemistry*
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Stereoisomerism
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Taxoids*
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Taxus / chemistry*
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Trees / chemistry*
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Tumor Cells, Cultured / drug effects
Substances
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Antineoplastic Agents, Phytogenic
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Bridged-Ring Compounds
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Diterpenes
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Drugs, Chinese Herbal
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Taxoids
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hongdoushan A
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hongdoushan B
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hongdoushan C
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taxane
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Paclitaxel