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α‐Pyrones and Pyranes from the Plant Pathogenic Fungus Pestalotiopsis scirpina
Author(s) -
Li Jian,
Wu Xianfu,
Ding Gang,
Feng Yu,
Jiang Xuejun,
Guo Liangdong,
Che Yongsheng
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.201200007
Subject(s) - chemistry , circular dichroism , stereochemistry , pestalotiopsis , absolute configuration , cytotoxicity , fungus , botany , biochemistry , in vitro , biology
Three new α‐pyrones, scirpyrones A–C ( 1 – 3 ), and four new pyranes, scirpyranes A–D ( 4 – 7 ), were isolated from solid cultures of the plant pathogen Pestalotiopsis scirpina . Their structures were elucidated primarily by NMR experiments. The absolute configurations of C‐7 and C‐2′ in 1 , C‐7 in 2 , and C‐6 and C‐7 in 3 were deduced on the basis of circular dichroism (CD) data, whereas those of the secondary alcohols in 4 – 7 were determined by a modification of Mosher's method. Compound 1 is the first described 6‐(5‐oxotetrahydrofuran‐2‐yl)‐2 H ‐pyran‐2‐one. Compounds 4 – 6 showed significant cytotoxicity towards MCF‐7 cells.