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New Bioactive 2,3‐Epoxycyclohexenes and Isocoumarins from the Endophytic Fungus Phomopsis sp. from Laurus Azorica
Author(s) -
Hussain Hidayat,
Akhtar Nadeem,
Draeger Siegfried,
Schulz Barbara,
Pescitelli Gennaro,
Salvadori Piero,
Antus Sándor,
Kurtán Tibor,
Krohn Karsten
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801052
Subject(s) - chemistry , two dimensional nuclear magnetic resonance spectroscopy , circular dichroism , stereochemistry , isocoumarins , ethyl acetate , proton nmr , botany , organic chemistry , biology , catalysis
Six new metabolites, namely cycloepoxylactone ( 1a ), cycloepoxytriol A ( 2 ), cycloepoxytriol B ( 3 ) and phomolactones A–C ( 4 – 6 ), were isolated from two cultures of the ethyl acetate soluble fraction of the endophytic fungus Phomopsis sp. (internal strain no. 7233). Their structures were determined by means of spectroscopic data including HREIMS, 1 H NMR, 13 C NMR, and 2D NMR (HMQC, HMBC, and NOESY). The absolute configurations of 1a , 4 and 5 were determined by circular dichroism and comparison of solution CD spectra with TDDFT‐calculated ones. Preliminary studies showed that cycloepoxylactone ( 1a ) has good antibacterial, antifungal, and algicidal activity against Bacillus megaterium , Microbotryum violaceum , and Chlorella fusca , respectively, whereas cycloepoxytriol B ( 3 ) has good algicidal activity against Chlorella fusca .(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)