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Diketopiperazine Alkaloids Produced by the Endophytic Fungus Aspergillus fumigatus from the Stem of Erythrophloeum fordii Oliv .
Author(s) -
Liu YuXi,
Ma ShuangGang,
Wang XiaoJing,
Zhao Nan,
Qu Jing,
Yu ShiShan,
Dai JunGui,
Wang YingHong,
Si YiKang
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100521
Subject(s) - chemistry , aspergillus fumigatus , stereochemistry , fungus , in vitro , two dimensional nuclear magnetic resonance spectroscopy , mtt assay , aspergillus , microbiology and biotechnology , biochemistry , botany , biology
Four new diketopiperazine alkaloids, rel ‐(8 R )‐9‐hydroxy‐8‐methoxy‐18‐ epi ‐fumitremorgin C ( 1 ), rel ‐(8 S )‐19,20‐dihydro‐9,20‐dihydroxy‐8‐methoxy‐9,18‐di‐ epi ‐fumitremorgin C ( 2 ), rel ‐(8 S ,19 S )‐19,20‐dihydro‐9,19,20‐trihydroxy‐8‐methoxy‐9‐ epi ‐fumitremorgin C ( 3 ), and (3 S ,8 S ,9 S ,18 S )‐8,9‐dihydroxyspirotryprostatin A ( 4 ), together with the eight known compounds 5 – 12 , were isolated from the endophytic fungus Aspergillus fumigatus. The structures of the new compounds were determined by extensive spectroscopic methods including HR‐ESI‐MS, NMR, and CD experiments. Compound 12 showed weak inhibitory activity in vitro against the release of β‐ glucuronidase in rat polymorphonuclear leukocytes induced by the platelet‐activating factor. None of the twelve compounds exhibited detectable cytotoxic activities toward five human tumor cell lines (HCT‐8, Bel‐7402, BGC‐823, A549, and A2780) in the MTT assay.