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Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum.
Molecules
October 2017
Department of Microbial Drugs, Helmholtz Centre for Infection Research and German Centre for Infection Research (DZIF), partner site Hannover/Braunschweig, Inhoffenstrasse 7, 38124 Braunschweig, Germany.
Extracts from an endophytic fungus isolated from the roots of the Algerian plant showed prominent antimicrobial activity in a screening for novel antibiotics. The producer organism was identified as by means of morphological studies and molecular phylogenetic methods. Studies on the secondary metabolite production of this strain in various culture media revealed that the major components from shake flasks were massarilactones D () and H () as well as two new furanone derivatives for which we propose the trivial names (5)--gregatin B () and graminin D ().
View Article and Find Full Text PDFThree new natural furanones, pulvinulin A (1), graminin C (2), and cis-gregatin B (3), together with the known fungal metabolites, graminin B (4) and 10-norparvulenone (5), were isolated from Pulvinula sp. 11120, an endophytic fungal strain occurring in healthy foliage of Cupressus arizonica (Arizona cypress). The structures of 1 and 2 were elucidated by the analysis of their spectroscopic data and chemical interconversions, and that of 3 was determined by comparison with data for synthetic cis-gregatin B.
View Article and Find Full Text PDFGraminin B, a furanone from the fungus Paraconiothyrium sp.
J Antibiot (Tokyo)
May 2014
Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Granada, Spain.
A serendipitous synthesis of (+)-gregatin B, second structure revisions of the aspertetronins, gregatins, and graminin A, structure revision of the penicilliols.
Org Lett
May 2011
Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Freiburg im Breisgau, Germany.
A (DHQN)(2)AQN-promoted asymmetric dihydroxylation (92% ee) of the allyl chloride derived from enynol (E)-13 and an 8-step sequence provided access to the hydroxyethylated furanone (R)-21. Oxidation with MnO(2) furnished 50% furanone (+)-(R)-2a and 2.7% isomeric furanone (+)-(R)-3a.
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