Abstract
Ten new derivatives (2-11) of ambrein (1), isolated from ambergris, were prepared by chemical transformation. Oxidation and/or cyclization were effected by reactions with selenium oxide or p-toluenesulfonyl chloride or with the use of shortwave UV light. The structures of 2-12 were elucidated by spectroscopic analysis, with the structure and relative configuration of 9 confirmed by single-crystal X-ray crystallography. The cytotoxic activities of 1-12 were investigated against human liver carcinoma (Hepa59T/VGH), colon adenocarcinoma (WiDr), lung carcinoma (A-549), and human breast adenocarcinoma (MCF-7) cell lines. The anti-inflammatory activities of 1-11, in terms of the inhibition of human neutrophil function, were also evaluated.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Ambergris / chemistry
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Ambergris / isolation & purification*
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Ambergris / pharmacology
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Animals
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Anti-Inflammatory Agents, Non-Steroidal / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification*
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Antineoplastic Agents / pharmacology
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Drug Screening Assays, Antitumor
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Humans
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Molecular Structure
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Naphthols / chemistry
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Naphthols / isolation & purification*
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Naphthols / pharmacology
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Neutrophils / drug effects
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Pancreatic Elastase / metabolism
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Sperm Whale
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Triterpenes / chemistry
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Triterpenes / isolation & purification
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Triterpenes / pharmacology
Substances
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Ambergris
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Anti-Inflammatory Agents, Non-Steroidal
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Antineoplastic Agents
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Naphthols
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Triterpenes
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ambrein
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Pancreatic Elastase