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Chromogenic Meroterpenoids from the Mushrooms Russula ochroleuca and R. viscida
Author(s) -
Sontag Bernd,
Rüth Matthias,
Spiteller Peter,
Arnold Norbert,
Steglich Wolfgang,
Reichert Matthias,
Bringmann Gerhard
Publication year - 2006
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.200500714
Subject(s) - chemistry , benzaldehyde , mushroom , hemiacetal , stereochemistry , organic chemistry , anomer , food science , catalysis
The spirodioxolactone ochroleucin A 1 ( 1 ) is responsible for the red colour produced when the stalk base of Russula ochroleuca and R. viscida is treated with aqueous KOH. The labile chromogen rearranges easily into the isomeric dilactoneochroleucin A 2 ( 2 ). Ochroleucin A 1 is accompanied by the biosynthetically related hemiacetal ochroleucin B ( 5 ). The new compounds, whose structures were established by MS and NMR methods, appear to be derived biosynthetically by oxidative condensation of two monomeric units. One of them, 2,5‐dihydroxy‐4‐(3‐methylbut‐3‐en‐1‐ynyl)benzaldehyde ( 6 ), was detected in the crude toadstool extract by GC/MS comparison with a synthetic sample. The absolute configurations of the ochroleucins A 1 and B have been determined by quantum chemical calculation of their CD spectra. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)