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Isolation and Synthesis of Methyl Bovinate, an Unusual Pulvinic Acid Derivative from Suillus bovinus (Basidiomycetes) Helmut Besla, Andreas Bresinskya, Claus Kilpertb, Wolfgang Marschnerb, Helga M. Schmidtb, and Wolfgang Steglichc a Institut für Botanik der Universität Regensburg, D-93040 Regensburg, Germany b Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany c Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstraße 5 – 13, D-81377 München, Germany

New Pulvinic Acid and Phenylalaninol Derivatives from the Mushrooms Retiboletus griseus and R. nigerrimus Gertraud Grubera, Lydia Kerschensteinera, Ryuji Marumotob†, and Wolfgang Steglicha a Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstr. 5 – 13, 81377 München, Germany b 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 Z. Naturforsch. 2013, 68b, 675 – 682 / DOI: 10.5560/ZNB.2013-3050 Received

Chromapedic Acid, Pulvinic Acids and Acetophenone Derivatives from the Mushroom Leccinum chromapes (Boletales) Gertraud Gruber, Lydia Kerschensteiner and Wolfgang Steglich Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5 – 13 (Haus F), 81377 München, Germany Reprint requests to Prof. Dr. Wolfgang Steglich. Fax: +49-89-2180-77756. E-mail: wos@cup.uni-muenchen.de Z. Naturforsch. 2014, 69b, 432 – 438 / DOI: 10.5560/ZNB.2014-3307 Received December 2, 2013 Dedicated to the memory of the late Dr. Ryuji Marumoto The pigment responsible for the

292 Notizen New Synthetic Nitrogen-Derivatives of Pulvinic Acid Yngve Solberg Chemical Research Laboratory, Agricultural University of Norway, As-NLH (Z. Naturforsch. 32 c, 292 — 293 [1977] ; received July 19/December 22, 1976) Lichen, Pulvinic Acid Lactams Pulvinic acid lactams have been synthesized by reaction of the lichen compound vulpinic acid and 2-hydroxyethoxy- acetamide. The structure were established by consideration of infrared, mass and nuclear magnetic resonance spectra. The lichen compound pulvinic acid and its deriva­ tives have been

Pilzpigmente, X X X V [1] 3-O-Methylvariegatsäure und verwandte Pulvinsäurederivate aus Kulturen von Hygrophoropsis aurantiaca (Boletales) Pigments of Fungi, XXXV 3-0-Methylvariegatic Acid and Related Pulvinic Acid Derivatives from Cultures of Hygrophoropsis aurantiaca (Boletales) Helmut Besl und Andreas Bresinsky Lehrstuhl Botanik II, Fachbereich Biologie der Universität Regensburg und Lothar Kopanski und Wolfgang Steglich Institut für Organische Chemie und Biochemie der Universität Bonn Z. Naturforsch. 33 c, 820 — 825 (1978) ; eingegangen am 19. September

Notizen 363 Neue Pulvinsäurederivate aus Pulveroboletus- Arten (Boletales) [1] New Pulvinic Acid Derivatives from Pulveroboletus Species (Boletales) [1 ] Ryuji Marumoto Rokko Pilzlaboratorium. Ashiya-shi, Hyogo, Japan Claus Kilpert und Wolfgang Steglich Institut für Organische Chemie und Biochemie der Univer­ sität Bonn Z. Naturforsch. 41c, 363-365 (1986); received October 4, 1985 Pulveroboletus, Boletales, Basidiomycetes. Vulpinic Acid, Chlorinated Pulvinic Acid Derivatives Vulpinic acid has been isolated from sporophores of Pul­ veroboletus ravenelii, its

(Fa. Boehringer und Söhne/Schwabenheim) zur Verfügung gestellt. Mit Unterstützung des Swedish Medical Research Council No. B70-14X-56-06 und B70-14X-05. Bildung von Pulvinsäurederivaten durch Hygrophoropsis aurantiaca (Paxillaceae-Boletales) in vitro Formation of Pulvinic Acids by Hygrophoropsis aurantiaca (Paxillaceae-Boletales) in Vitro A . BRESINSKY u n d R . B A C H M A N N Botanische Staatssammlung München (Z. Naturforsdi. 26 b, 1086—1087 [1971] ; eingegangen am 5. August 1971) In Fortsetzung von Veröffentlichungen über die Be- deutung von

96 W. STEGLICH E T A L . ■ PILZPIG M EN TE Pilzpigmente, X IX 1 Festlegung der Struktur von Pulvinsäuren m it H ilfe der NMR-Spektroskopie Pigments of Fungi, X IX 1 Structural Determination of Pulvinic Acids by NMR Spectroscopy W o l f g a n g S t e g l i c h , H e l m u t B e s l u n d K l a u s Z i p f e l Organisch-Chem isches In s t i tu t der T echnischen U n iv e rs itä t B erlin Herrn Prof. Dr. H a n s B r o c k m a n k zum 70. Geburtstag gewidmet (Z. Xaturforsch. 29 b, 96-98 [1974]; eingegangen am 15. Oktober 1973) P ulv in ic acids

determined by 1H and 13C NMR spectroscopy of the corresponding methyl ester as all-trans-16-oxohexadeca-2,4,6,8,10,12,14- heptaenoic acid (1). Neither pulvinic acids nor other typical Boletales pigments could be detected in this fungus. The structural relationship of 1 to other polyene pigments from fungi is discussed. Key words: Calostoma, Boletales, Polyenes, Mushroom Pigments, Chemotaxonomy Introduction Calostoma cinnabarinum Corda (Stalked Puffball- in-aspic) is a striking red-orange puffball widespread in the eastern USA and Asia. It is easily recognized by its

. Attempts to shorten the elution time of the stan­ dard mixture resulted in simultaneous elution of stictic acid and erythrin on one hand and schizopelt- ic and vulpinic acid on the other hand. However, in the application, mostly concerned with simple mix­ tures of secondary lichen products, HPLC runs can be shorten down to 10 - 15 min. Mixtures, containing besides depsides and depsi­ dones also pulvinic acid derivatives, e. g. pulvinic acid (Table I) or pinastric acid (see Fig. 2), are more difficult to resolve, however, detection and quantifi­ cation of the