Open AccessTalarolide A, a Cyclic Heptapeptide Hydroxamate from an Australian Marine Tunicate-Associated Fungus, Talaromyces sp. (CMB-TU011)
Author(s) -
Pradeep Dewapriya,
Pritesh Prasad,
Rakesh Damodar,
Angela A. Salim,
Robert J. Capon
Publication year - 2017
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.7b00638
Subject(s) - tunicate , chemistry , fungus , stereochemistry , marine fungi , peptide , metabolite , ciona intestinalis , cyclic peptide , diterpene , regioselectivity , antifungal , botany , organic chemistry , biochemistry , microbiology and biotechnology , biology , gene , ecology , catalysis
A miniaturized 24-well plate microbioreactor approach was used to explore secondary metabolite media dependence in an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB TU011). Detailed chemical investigations of an antifungal M1-saline cultivation yielded talarolide A (1), only the second reported natural cyclic peptide hydroxamate, and the first from a fungus. The antifungal properties of the M1-saline extract were attributed to the known diterpene glycoside sordarin (2). Structure elucidation of 1 and 2 was achieved by detailed spectroscopic analysis, with amino acid configurations in 1 assigned by the C 3 and C 18 Marfey's methods, and l-Ala and d-Ala regiochemistry by the recently reported 2D C 3 Marfey's method.