Premium
Pseudoanguillosporin A and B: Two New Isochromans Isolated from the Endophytic Fungus Pseudoanguillospora sp.
Author(s) -
Kock Ines,
Draeger Siegfried,
Schulz Barbara,
Elsässer Brigitta,
Kurtán Tibor,
Kenéz Ágnes,
Antus Sándor,
Pescitelli Gennaro,
Salvadori Piero,
Speakman JohnBryan,
Rheinheimer Joachim,
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.200801083
Subject(s) - chemistry , absolute configuration , chirality (physics) , zindo , stereochemistry , derivative (finance) , helicity , computational chemistry , organic chemistry , molecule , chiral symmetry breaking , physics , particle physics , quantum mechanics , financial economics , nambu–jona lasinio model , economics , quark
Two new isochromans named pseudoanguillosporin A ( 2a ) and B ( 3 ), together with the known cephalochromin ( 1 ), were isolated from Pseudoanguillospora sp. The C‐2 absolute configuration of 2a and 3 was deduced from its CD spectrum by the isochroman helicity rule, supported by TDDFT CD calculations. The absolute configuration of the sec ‐hydroxyl group of 3 was determined by the Mosher NMR method from the MPA esters of its methylated derivative. The axial chirality of 1 was assigned through exciton analysis of its CD spectrum and confirmed by ZINDO CD calculations. The metabolites showed broad antimicrobial activities.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)