|
Z. Naturforsch. 2013,
68b, 675 – 682
doi:10.5560/ZNB.2013-3050
New Pulvinic Acid and Phenylalaninol Derivatives from the Mushrooms Retiboletus griseus and R. nigerrimus
1 Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstr. 5–13, 81377 München, Germany
2 Rokko Mycological Laboratory, 53-1, Okuike-minamimachi, Ashiya, Hyogo 659, Japan
Reprint requests to Prof. Dr. Wolfgang Steglich. Fax: + 49-89-2180-77756. E-mail:
wos@cup.uni-muenchen.de
Received February 14, 2013 / published online Juli 2, 2013
Dedicated to Professor Heinrich Nöth on the occasion of his 85th birthday
The close genetic relationship of the mushrooms Retiboletus griseus and R. nigerrimus is supported by the occurrence of the orange-yellow retiboletic acid, resp. its methyl ester, in both species. The structures of these highly substituted pulvinic acid derivatives have been elucidated by spectroscopic investigations. R. nigerrimus also contains two N-protocatechuyl-l-phenylalaninol derivatives, nigerrimin A and B, the first reported occurrence of such compounds in nature. Their configuration was established by the synthesis of nigerrimin B.
Key words: Pulvinic Acids, N-(Protocatechuyl)phenylalaninols, Fungi, Taxonomy, Synthesis