Epicoccarines A, B and epipyridone: tetramic acids and pyridone alkaloids from an Epicoccum sp. associated with the tree fungus Pholiota squarrosa.
Investigation of the metabolic profile of a fungus (Epicoccum sp.) isolated from the fruiting body of the tree fungus Pholiota squarrosa led to the discovery of two novel tetramic acid derivatives, epicoccarine A (2) and B (3), as well as a new pyridone alkaloid, epipyridone (1), with an unusually cyclized side chain. It appears that 1 is biogenetically derived from the ring expansion of 2 followed by a proposed hetero-Diels-Alder reaction. 2 shows selective antibacterial activity against Gram positive bacteria, in particular Mycobacterium vaccae.
Kemami Wangun
Hilaire V
HV
Dept. Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, Beutenbergstr. 11a, 07745 Jena, Germany.
Hertweck
Christian
C
D000470:Alkaloids / Q000096:biosynthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000378:metabolism*; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000737:chemistry* / Q000378:metabolism*; D011728:Pyridones / Q000737:chemistry / Q000378:metabolism*; D011760:Pyrrolidinones / Q000378:metabolism*; D014197:Trees / Q000382:microbiology*
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D011728:Pyridones; D011760:Pyrrolidinones; C522278:epicoccarine A; C522277:epicoccarine B; C522275:epipyridone; C009435:tetramic acid