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Metabolic Products of the Endophytic Fungus Microsphaeropsis sp. from Larix decidua
Author(s) -
Dai Jingqiu,
Krohn Karsten,
Elsässer Brigitta,
Flörke Ulrich,
Draeger Siegfried,
Schulz Barbara,
Pescitelli Gennaro,
Salvadori Piero,
Antus Sándor,
Kurtán Tibor
Publication year - 2007
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.200700348
Subject(s) - chemistry , absolute configuration , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , chemical shift , single crystal , nmr spectra database , crystallography , spectral line , physics , astronomy
Abstract Five new metabolites, palmarumycin M 1 ( 1a ) and M 2 ( 3 ), papyracillic acid C ( 6 ) and the microsphaeropsins A ( 7 ) and B ( 8 ) were isolated from the fungus Microsphaeropsis sp. together with the known decaspirone ( 2 ) and the papyracillic acids A and B ( 4 and 5 ). 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. The absolute configuration of palmarumycin M 1 ( 1a ) was determined by single‐crystal X‐ray analysis of the bis(4‐bromobenzoate) 1c and the relationship between 1a , 2 and 3 established by chemical transformation of 1a into 2 and of 3 into 2 . The relative configuration of papyracillic acids A–C ( 4 – 6 ) was revised and their absolute configuration determined by comparison of TDDFT‐calculated and experimental solid‐state CD spectra.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)