11-Oxygenated cytotoxic 8,9-secokauranes from a New Zealand liverwort, Lepidolaena taylorii

Four new cytotoxic 8,9-secokauranes have been identified from the liverwort Lepidolaena taylorii. The 11-oxygenation found in three of these has not been encountered in the 8,9-secokauranes known from higher plants. NMR studies were combined with molecular modelling to determine the preferred confor...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 1999-02, Vol.50 (3), p.423-433
Main Authors: Perry, Nigel B, Burgess, Elaine J, Baek, Seung-Hwa, Weavers, Rex T, Geis, Wolfgang, Mauger, Anthony B
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
Cell Division - drug effects
Chemical constitution
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Drug Screening Assays, Antitumor
Fundamental and applied biological sciences. Psychology
General pharmacology
Humans
Magnetic Resonance Spectroscopy
Mass Spectrometry - methods
Medical sciences
Mice
Molecular Structure
Oxygen - chemistry
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant physiology and development
Plants - chemistry
Tumor Cells, Cultured
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Summary:Four new cytotoxic 8,9-secokauranes have been identified from the liverwort Lepidolaena taylorii. The 11-oxygenation found in three of these has not been encountered in the 8,9-secokauranes known from higher plants. NMR studies were combined with molecular modelling to determine the preferred conformations. Six structurally related kauren-15-ones were also found, including three new compounds. Some of these compounds showed differential cytotoxic activity against human tumor cell lines. The probable mode of cytotoxic action was supported by Michael addition of a thiol. Two 8,9-secokauranes were the main cytotoxins in another New Zealand liverwort, L. palpebrifolia.
ISSN:0031-9422
1873-3700
DOI:10.1016/S0031-9422(98)00602-5