Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Immunomodulatory Constituents from an Ascomycete, Emericella aurantio-brunnea
Haruhiro FUJIMOTOEtsuko NAKAMURAEmi OKUYAMAMasami ISHIBASHI
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JOURNAL FREE ACCESS

2000 Volume 48 Issue 10 Pages 1436-1441

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Abstract

Fractionation monitored by the immunomodulatory activity of the AcOEt extract of an Ascomycete, Emericella aurantio-brunnea, afforded two known fungal sesterterpenes, variecolin (1) and variecolactone (2), two new variecolin congeners named variecoacetals A (3) and B (4), and a new sesquiterpenetriol diester named emeremophiline (5), as the immunosuppressive constituests of this fungus. The absolute configuration of 1, which was previously not determined, was determined to be (2S, 3S, 6R, 10S, 11R, 14S, 15R, 16S) from the NMR spectral data of the (6R, 7R)-dimethyl-1, 3, 5-trioxacycloheptyl derivative of 1 (7). The absolute configurations of the other variecolin congeners, 2-4, and variecolol (6) are also proposed form biosynthetic considerations.

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© The Pharmaceutical Society of Japan
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