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Sarcodonins and Sarcoviolins, Bioactive Polyhydroxy‐ p ‐terphenyl Pyrazinediol Dioxide Conjugates from Fruiting Bodies of the Basidiomycete Sarcodon leucopus
Author(s) -
Calì Valeria,
Spatafora Carmela,
Tringali Corrado
Publication year - 2004
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.200300407
Subject(s) - chemistry , terphenyl , organic chemistry , epimer , stereochemistry
Six new polyhydroxy‐ p ‐terphenyl pyrazinediol dioxide conjugates ( 4 − 9 ) related to sarcodonin ( 3 ) have been isolated from the EtOAc extract of the fruiting bodies of the basidiomycete Sarcodon leucopus and we established their structures by spectral analysis and chemical conversions. Three of them, named sarcodonins α ( 4 ), β ( 5 ), and γ ( 6 ), afforded the same peracetate 12 upon acetylation. Compounds 7 , 8 , and 9 gave peracetate 13 and were characterized as the N ‐oxide epimers of 3 − 5 , respectively, and are named, accordingly, episarcodonin, episarcodonin α, and episarcodonin β. From the EtOH extract, we obtained a mixture of two violet pigments. Chemical and spectroscopic data allowed their structures to be established as the p ‐terphenyl ortho ‐quinones related to the sarcodonins, namely sarcoviolin α ( 10 ) and episarcoviolin α ( 11 ). Compounds 3 , 4 , 6 , and 7 and the mixture of 10 and 11 were found to be active in assays against tumor cell cultures. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)