Isolation and structure elucidation of four fatty acid derivatives of the mycotoxin fusarochromanone produced by Fusarium equiseti

Abstract

Four compounds were found in rice cultures of Fusarium equiseti (Alaska 2-2). Analysis by mass spectrometry (El, PCI, and FAB) indicated that compounds I, II, III, and IV had molecular formulas of C33H52N2O6 (572.3755), C35H52N2O6 (596.3764), C35H54N2O6 (598.3884), and C35H56N2O6 (600.4149), respectively. Hydrolysis of a mixture of the four compounds with 1.2 N HC1 in 80% methanol yielded six compounds. They were identified by mass spectrometry as 2,2-dimethyl-5-amino-6-(3'-amino-4'hydroxybutyryl) -4-chromone (fusarochromanone, TDP-1), 2,2-dimethyl-5-amino-6-(3,-7V-acetyl-4'-hydroxybutyryl)-4-chromone (3'-2V-acetylfusarochromanone, TDP-2), and methyl esters of four fatty acids, including 14-methylpentadecanoic acid, 10,12-octadecadienoic acid, 9-octadecenoic acid, and 16-methylheptadecanoic acid. The fatty acid methyl esters were resolved by gas chromatography with a capillary column. The locations of double bonds in the fatty acyl moieties of compounds II and III were determined by the El mass spectra of their TMSO derivatives. The structures of the four compounds were determined to be 3'-N-acetyl-4'-0-fatty acylated fusarochromanone. The mass spectral analysis was supported by NMR and infrared spectral data.

The phytotoxicity ofFusarium metabolites: An update since 1989

“…[103][104][105][106][107][108]. Since being first isolated in 1986 from F. equiseti growing on Alaskan oat [103], several TDP-1 analogues have been isolated, mainly from rice culture [104][105][106][107][108]. TDP-1 has been implicated in tibial dyschondroplasia (TD) in poultry [ 109].…”

Synthesis of β-Amino and β-Methoxy Ketones by Lewis Acids Promoted β-Substitution Reactions of β,γ-Unsaturated Ketones

“…b-Amino carbonyl compounds exhibit as an important structure in many natural products and a useful synthetic intermediate in organic synthesis. [18][19][20][21][22][23] b-Amino ketone is typically produced by the addition reaction of nucleophilic amine to a,b-unsaturated ketone in the absence of acidic a-protons. According to the results b,g-unsaturated ketones were transformed into their corresponding b-methoxy ketones by Lewis acid promoted bsubstitution reactions.…”

Isolation and Structure Identification of Two New Derivatives of the Mycotoxin Fusaro-chromenone Produced by Fusarium equiseti

“…It is a 4-chromone derivative with some unusual substituents. Several fusarochromanone derivatives have been found in cultures of F. equiseti (3,(6)(7)(8). Two minor metabolites, 2 and 4, were also isolated as yellow powders from a rice culture of the fungal isolate.…”