Abstract
One new sterol, crassarosterol A (1), and four new steroidal glycosides, crassarosterosides A-D (2-5) were isolated from the Formosan soft coral Sinularia crassa. The absolute configuration of 1 was determined using the Mosher's method. The absolute configurations for the sugar moieties of 2-5 were determined by HPLC analysis on the o-tolylthiocarbamates derived from the liberated sugar after acid hydrolysis. Compounds 2 and 4 could significantly inhibit the expression of pro-inflammatory iNOS protein at 10 µM. In contrast, 1-3 were found to stimulate the expression of COX-2 protein at this concentration. Steroids 1 and 4 also showed cytotoxicity toward the selected human liver cancer cells.
Keywords:
Sinularia crassa; anti-inflammatory activity; crassarosterol A; crassarosterosides A–D; o-tolylthiocarbamate.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anthozoa / metabolism*
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / isolation & purification*
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Anti-Inflammatory Agents / metabolism
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Anti-Inflammatory Agents / pharmacology*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification*
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Antineoplastic Agents / metabolism
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Antineoplastic Agents / pharmacology*
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Cell Line, Transformed
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Cell Line, Tumor
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Cyclooxygenase 2 / metabolism
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Drug Discovery
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Glycosides / chemistry
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Glycosides / isolation & purification
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Glycosides / metabolism
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Glycosides / pharmacology
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Humans
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Inhibitory Concentration 50
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Macrophages / drug effects
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Macrophages / immunology
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Macrophages / metabolism
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Mice
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Molecular Structure
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Neoplasms / drug therapy
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Nitric Oxide Synthase Type II / metabolism
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Pacific Ocean
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Stereoisomerism
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Sterols / chemistry
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Sterols / isolation & purification*
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Sterols / metabolism
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Sterols / pharmacology*
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Taiwan
Substances
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Anti-Inflammatory Agents
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Antineoplastic Agents
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Glycosides
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Sterols
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Nitric Oxide Synthase Type II
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Nos2 protein, mouse
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Ptgs2 protein, mouse
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Cyclooxygenase 2