Journal
TETRAHEDRON
Volume 72, Issue 4, Pages 489-495Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.11.056
Keywords
Allahabadolactone A; Allahabadolactone B; Aspergillus allahabadii; Endophytic fungus; Antibacterial activity
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Funding
- Bioresources Research Network [BRN 003 G-56]
- National Center for Genetic Engineering and Biotechnology (BIOTEC)
- Mahidol University
- Center for Innovation in Chemistry
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Two new compounds, allahabadolactones A (1) and B (2), along with 10 known compounds including 16-amino-isopimar-7-en-19-oic acid (3), 16-alpha-D-glucopyranosyloxyisopimar-7-en-19-oic acid (4), 16-alpha-D- mannopyranosyloxyisopimar-7-en-19-oic acid (5), ergosterol, (22E)-5 alpha,8 alpha-epidioxyergosta-6,22-dien-3 beta-ol, cerevisterol, (R)-(-)-methoxycarbonylmellein, (-)-piliformic acid, 7-dechlorogriseofulvin, and cytochalasin D, were isolated from the endophytic fungus, Aspergillus allahabadii BCC45335. Their chemical structures were determined based on NMR spectroscopic and mass spectrometric analyses. The absolute stereochemistry of compound 1 was established by an X-ray crystallographic analysis and the reactions with Mosher's reagents. A plausible biosynthesis of allahabadolactones A (1) and B (2) was also proposed. Antibacterial activity against Bacillus cereus and cytotoxicity against MCF-7, KB, NCI-H187, and Vero cells of the isolated compounds were also evaluated. (C) 2015 Elsevier Ltd. All rights reserved.
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