title: Malonofungin: an antifungal aminomalonic acid from Phaeoramularia fusimaculans.
abstract: In screening for antifungal metabolites, a novel compound, malonofungin, exhibiting growth inhibitory activity against Botrytis cinerea (grey mould), has been isolated from fermentations of Phaeoramularia fusimaculans CBS 616.87. Its structure is established as (E)-(3R,4S,5S)-5-acetoxy-2-amino-2-carboxy-3,4-dihydroxy-14-oxoicos++ +-6-enoic acid, representing an addition to the rare class of naturally occurring aminomalonic acids. 1H NMR data and extensive use of CD spectroscopy have been utilized to establish the absolute stereochemistry of malonofungin. The structural and biological relationship of malonofungin to previously reported fungal metabolites is discussed.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027.
authors.forename: N
authors.initials: N
authors.lastname: Berova
authors.forename: J
authors.initials: J
authors.lastname: Breinholt
authors.forename: G W
authors.initials: GW
authors.lastname: Jensen
authors.forename: A
authors.initials: A
authors.lastname: Kjaer
authors.forename: L C
authors.initials: LC
authors.lastname: Lo
authors.forename: K
authors.initials: K
authors.lastname: Nakanishi
authors.forename: R I
authors.initials: RI
authors.lastname: Nielsen
authors.forename: C E
authors.initials: CE
authors.lastname: Olsen
authors.forename: C
authors.initials: C
authors.lastname: Pedersen
authors.forename: C E
authors.initials: CE
authors.lastname: Stidsen
mesh_terms: D000107:Acetylation; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002942:Circular Dichroism; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008314:Malonates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000737:chemistry* / Q000187:drug effects; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D005231:Fatty Acids, Unsaturated; D008314:Malonates; C019249:aminomalonic acid; C086805:malonofungin