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Biosynthesis of Bromoroquefortines in a High Saline Medium by Penicillium chrysogenum , a Terrestrial Endophyte Collected from Coffea arabica
Author(s) -
da Silva José Vinicius,
Fill Taicia Pacheco,
Lotufo Letícia Veras,
do Ó. Pessoa Cláudia,
RodriguesFilho Edson
Publication year - 2014
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.201300447
Subject(s) - penicillium chrysogenum , chemistry , endophyte , coffea arabica , biosynthesis , botany , stereochemistry , biochemistry , enzyme , biology
Roquefortine C ( 1 ) and 11‐bromoroquefortine C ( 4 ) were isolated from Penicillium chrysogenum , an endophyte obtained from green leaves of Coffea arabica , during induction experiments by adding halide salts to the culture media. In our studies, 11‐bromoroquefortine D and 11‐bromo‐17‐hydroxybromoroquefortine C were identified by LC/HR‐MS. It is the first time that bromoroquefortine C and D are described as halogenated natural products. These halo alkaloids were shown to be biosynthesized from brominated tryptophan as the biosynthetic precursor. Cytotoxic and antibiotic assays using roquefortine C and 11‐bromoroquefortine C showed that the presence of the 11‐Br substituent impairs some biological activities of this alkaloid.