Revision of the Absolute Configuration at C(23) of Lanostanoids and Isolation of Secondary Metabolites from Formosan Soft Coral Nephthea erecta
Resource
CHEMISTRY & BIODIVERSITY 6: 86-95
Journal
Chemistry and Biodiversity
Journal Volume
6
Journal Issue
1
Pages
86-95
Date Issued
2009
Date
2009
Author(s)
Cheng, Shi-Yie
Wen, Zhi-Hong
Wang, Shang-Kewi
Chiang, Michael Y.
El-Gamal, Ali A. H.
Duh, Chang-Yih
Abstract
Three new oxygenated ergostanoids, 1-3, one known ergostanoid, 4, one new trinoreudesmadienone, 5, one new calamenene type sesquiterpene, 6, and one known aristolane-type sesquiterpene, (-)-aristolone (7), have been isolated from the AcOEt extract of the soft coral Nephthea erecta. The structures of these compounds were determined by extensive spectroscopic and X-ray crystallographic analysis, as well as Mosher's method. We revised the absolute configuration at C(23) in the side chain of some lanostanoids as a result of the Mosher's products of 1 (i.e., 1a and 1b). The cytotoxicities against selected cancer cells and the anti-inflammatory effects of these tested metabolites 1-7 were determined in vitro. ? 2009 Verlag Helvetica Chimica Acta AG, Z?rich.
Other Subjects
3beta,22 ergosta 5,24(28) diene 3,17,22 triol; 3beta,23 ergosta 5,24(28) diene 3,23 diol; 5,6,7,8 tetrahydro 4alpha,8 dimethylnaphthalen 2(4alpha h) one; 5,6,7,8 tetrahydro 5 methyl 8 (1 methylethyl)naphthalene 2 carbaldehyde; aristolone; ergostanoid derivative; lanostanoid derivative; natural product; Nephthea erecta extract; sesquiterpene derivative; trinoreudesmadienone; unclassified drug; drug derivative; lanostanoid; lanosterol; animal cell; antiinflammatory activity; article; controlled study; coral; drug cytotoxicity; drug isolation; drug screening; drug structure; electrospray mass spectrometry; human; human cell; leukemia cell line; macrophage; mouse; Nephthea erecta; nonhuman; structure analysis; Taiwan; X ray crystallography; animal; Anthozoa; cell line; chemistry; isolation and purification; nuclear magnetic resonance spectroscopy; Alcyonacea; Nephthea; Animals; Anthozoa; Cell Line; Humans; Lanosterol; Magnetic Resonance Spectroscopy; Mice
Type
journal article
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