α‐Pyrones and Pyranes from the Plant Pathogenic Fungus  Pestalotiopsis scirpina | Zendy

Li Jian | Zendy; Wu Xianfu | Zendy; Ding Gang | Zendy; Feng Yu | Zendy; Jiang Xuejun | Zendy; Guo Liangdong | Zendy; Che Yongsheng | Zendy

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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.

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