OR-1—a mixture of esters of glyceric acid produced byPenicillium funiculosum and its antitrypsin activity

Abstract

A mixture of related metabolites (denoted OR-1) was isolated from the fermentation broth of Penicillium funiculosum together with mitorubrinic acid. Structurally OR-1 is glyceric acid esterified with C14-C18 fatty acids. Steady-state studies revealed that OR-1 behaved like an uncompetitive trypsin inhibitor with Ki 17.6 mumol/L.

Synthesis and Interfacial Properties of Monoacyl Glyceric Acids as a New Class of Green Surfactants

“…Previously, a mixture of GA esters biochemically produced by Penicillium funiculosum was reported to exhibit antitrypsin activity 15 . We reported that chemically synthesized dioleoyl GAs also exhibit antitrypsin activity 13 .…”

Synthesis and Evaluation of Dioleoyl Glyceric Acids Showing Antitrypsin Activity

“…However, this value differs from the IC 50 of OR-1, which is 4.25 μM 13 . The analytical data on the structure of OR-1 13 suggest several structural possibilities, including GA diesterifi ed with homologous or heterologous fatty acids, and a mixture of 2-O-monoacyl-GA and 3-O-monoacyl-GA with homologous or heterologous fatty acids. However, the contributions of these possible OR-1 constituents to the antitrypsin activity are unknown.…”

“…However, because only 100 mg of OR-1 was prepared from a 5-L culture of P. funiculosum 13 in one study, its productivity appears to be low. Additionally, OR-1 was revealed to be only a mixture of esters of GA, and, from the published data 13 , it remains unknown whether it is diacyl-GA, a mixture of 2-O-monoacyl-GA and 3-O-monoacyl-GA, or their mixture.…”

“…Previously, Lešová et al 2001 reported the isolation and identification of metabolite OR-1, produced during fermentation by Penicillium funiculosum. The structure of OR-1 was identifi ed by infrared spectrophotometry IR , 1 H-and 13 C-nuclear magnetic resonance NMR , and gas chromatography GC ; it was revealed to be a mixture of GA esterifi ed with C 14 -C 18 fatty acids.…”

“…Additionally, OR-1 was revealed to be only a mixture of esters of GA, and, from the published data 13 , it remains unknown whether it is diacyl-GA, a mixture of 2-O-monoacyl-GA and 3-O-monoacyl-GA, or their mixture. Hence, the contributions of the possible OR-1 constituents to antitrypsin activity also remain unknown.…”