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New Oblongolides Isolated from the Endophytic Fungus Phomopsis sp. from Melilotus dentata from the Shores of the Baltic Sea
Author(s) -
Dai Jingqiu,
Krohn Karsten,
Gehle Dietmar,
Kock Ines,
Flörke Ulrich,
Aust HansJürgen,
Draeger Siegfried,
Schulz Barbara,
Rheinheimer Joachim
Publication year - 2005
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.200500290
Subject(s) - alternariol , chemistry , two dimensional nuclear magnetic resonance spectroscopy , phomopsis , stereochemistry , ergosterol , nuclear magnetic resonance spectroscopy , carbon 13 nmr , mycotoxin , substituent , botany , food science , biochemistry , biology
Thirteen new metabolites, namely oblongolides B–M ( 2 – 13 ) and 4‐[5‐(1‐hydroxyethyl)furan‐2‐yl]‐4‐oxobutanoic acid ( 14 ), together with the six known compounds phomopsolide B ( 15 ), alternariol dimethyl ether ( 16 ), alternariol monomethyl ether ( 17 ), the mycotoxin alternariol ( 18 ), ergosterol ( 19 ), and 5α,8α‐epidioxyergosterol ( 20 ) were isolated from the endophytic fungus Phomopsis sp. The new biologically active norsesquiterpene γ‐lactones differ in their degree of substitution, saturation, and substituent pattern from the known oblongolide 1 . Their structures were determined by means of spectroscopic data including HREIMS, 1 H NMR, 13 C NMR, 2D NMR (HMQC, HMBC, NOESY) and X‐ray single crystal analysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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