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Decalactone Derivatives from Corynespora cassiicola , an Endophytic Fungus of the Mangrove Plant Laguncularia racemosa
Author(s) -
Ebrahim Weaam,
Aly Amal H.,
Mándi Attila,
Totzke Frank,
Kubbutat Michael H. G.,
Wray Victor,
Lin WenHan,
Dai Haofu,
Proksch Peter,
Kurtán Tibor,
Debbab Abdessamad
Publication year - 2012
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.201200245
Subject(s) - corynespora cassiicola , chemistry , mangrove , stereochemistry , absolute configuration , botany , biology , ecology , leaf spot
Chemical investigation of the ethyl acetate extract of Corynespora cassiicola , isolated from leaf tissues of the Chinese mangrove medicinal plant Laguncularia racemosa , yielded four new secondary metabolites, including three decalactones, xestodecalactones D–F ( 1 – 3 ) as well as corynesidone C ( 4 ), in addition to four known compounds. The structures of the new compounds were determined on the basis of one‐ and two‐dimensional NMR spectroscopy as well as by high‐resolution mass spectrometry. Absolute configurations of the optically active compounds 1 – 3 were determined by TDDFT ECD calculations of their solution conformers, proving that they belong to the (11 S ) series of xestodecalactones, opposite to the (11 R ) configuration of the known xestodecalactones A–C. All compounds were tested against a panel of human protein kinases. Among the isolated compounds, two inhibited several kinases such as IGF1‐R and VEGF‐R2 with IC 50 values mostly in the low micromolar range.