Abstract
Eighteen compounds with a botryane skeleton have been obtained through chemical transformations of various toxins from the fungus Botrytis cinerea. During the course of these transformations, the C-10 carbon of the botryane skeleton was found to exhibit an interesting high regioselectivity to oxidizing and reducing agents. In addition, the cytotoxicity of 27 botryane derivatives was determined in vitro against Hs578T, MDA-MB-231, HT-1080, U87-MG, IMR-90, and HUVEC cell lines. The results of this study confirm that the cytotoxicity of botrydial (1) and its derivatives is related to the presence of a 1,5-dialdehyde functionality.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Aldehydes / isolation & purification*
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Aldehydes / pharmacology
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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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Botrytis / chemistry*
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Breast Neoplasms
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Bridged Bicyclo Compounds / chemistry
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Bridged Bicyclo Compounds / isolation & purification*
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Bridged Bicyclo Compounds / pharmacology
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Chromatography, Gas
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Drug Screening Assays, Antitumor
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Female
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Fibrosarcoma
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Humans
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Molecular Structure
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Mycotoxins / chemistry*
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Sesquiterpenes / chemistry*
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
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Structure-Activity Relationship
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Tumor Cells, Cultured / drug effects
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Umbilical Veins / cytology
Substances
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Aldehydes
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Antineoplastic Agents, Phytogenic
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Bridged Bicyclo Compounds
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Mycotoxins
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Sesquiterpenes
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botrydial