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Structural and Stereochemical Studies of Hydroxyanthraquinone Derivatives from the Endophytic Fungus Coniothyrium sp
Author(s) -
Sun Peng,
Huo Juan,
Kurtán Tibor,
Mándi Attila,
Antus Sándor,
Tang Hua,
Draeger Siegfried,
Schulz Barbara,
Hussain Hidayat,
Krohn Karsten,
Pan Weihua,
Yi Yanghua,
Zhang Wen
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22128
Subject(s) - absolute configuration , chemistry , anthraquinones , stereochemistry , moiety , fungus , chirality (physics) , tetralone , botany , biology , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Four known hydroxyanthraquinones ( 1–4 ) together with four new derivatives having a tetralone moiety, namely coniothyrinones A–D ( 5–8 ), were isolated from the culture of Coniothyrium sp., an endophytic fungus isolated from Salsola oppostifolia from Gomera in the Canary Islands. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations of coniothyrinones A ( 5 ), B ( 6 ), and D ( 8 ) were determined by TDDFT calculations of CD spectra, allowing the determination of the absolute configuration of coniothyrinone C ( 7 ) as well. Coniothyrinones A ( 5 ), B ( 6 ), and D ( 8 ) could be used as ECD reference compounds in the determination of absolute configuration for related tetralone derivatives. This is the first report of anthraquinones and derivatives from an isolate of the genus Coniothyrium sp. These compounds showed inhibitory effects against the fungus Microbotryum violaceum , the alga Chlorella fusca , and the bacteria Escherichia coli and Bacillus megaterium . Chirality 25:141–148, 2013 . © 2012 Wiley Periodicals, Inc.