Furan, phenolic, and heptelidic acid derivatives produced by Aspergillus oryzae

Abstract

Eleven compounds, including a new sesquiterpene, were isolated from the culture medium of incubated with capsaicin. The structure of the new compound was determined to be 1,3,5a,6,7,8,9,9a-octahydro-9-hydroxy-9-(hydroxymethyl)-6-isopropyl-1-oxobenzo[c]oxepine-4- carboxylic acid, a heptelidic acid derivative. In addition, 10 known compounds were identified, namely 5-(hydroxymethyl)-3-furancarboxylic acid (flufuran), 3-hydroxypropanoic acid, 5-(hydroxymethyl)-2- furancarboxylic acid, 2-(4-hydroxyphenyl)-ethanol, 4-hydroxybenzoic acid, vanillic acid, 3,4-dihydroxybenzoic acid, 2-furanol, hydroheptelidic acid, and trichoderonic acid A, using spectroscopic data from nuclear magnetic resonance and electrospray ionization-mass spectroscopy.

Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

“…Flufuran, other related furans, and small molecular weight secondary metabolites, including 4-hydroxybenzoic acid, were isolated from Aspergillus oryzae and A. flavus (Evidente et al 2009 ; Lee et al 2016 ; Saldan et al 2018 ). Flufuran has antifungal activity (Evidente et al 2009 ).…”

“…Heptelidic acid (=koningic acid), hydroheptelidic acid, gliocladic acid, and trichoderonic acid are sesquiterpenes that have antibiotic and anticancer properties (Itoh et al 1989 ; Nakazawa et al 1997 ; Kim and Lee 2009 ). Heptelidic acid has been reported from both Aspergillus oryzae and A. flavus (Lee et al 2016 ; Skóra et al 2017 ).…”

Laserpitium zernyi Hayek Flower and Herb Extracts: Phenolic Compounds, and Anti‐edematous, Antioxidant, and Antimicrobial Activities

“…It is based on the reaction of • OH radical, formed from H 2 O 2 in ascorbate/Fe 2+ induced reaction, with 2‐deoxyribose, which leads to its degradation. The degradation products further react with TBA and form purple complexes with an absorption maximum of 532 nm . Samples of 20 μl of the herb and flower extracts dissolved in MeOH (2.44 – 39.11 mg/ml and 2.38 – 38.15 mg/ml, resp.…”

Survival strategy of the salt-tolerant lactic acid bacterium, Tetragenococcus halophilus, to counteract koji mold, Aspergillus oryzae, in soy sauce brewing

“…1 H-NMR (500 MHz), 13 C-NMR (125 MHz), COSY, HSQC, and HMBC spectra of the active compound were recorded in DMSO-d 6 with Bruker AVANCE 500 spectrometer (Bruker, Billerica, MA, USA). To confirm if the active compound was heptelidic acid (HA), the test compound and HA standard (Cosmo Bio) were analyzed by liquid chromatography mass spectrometry (LC/MS) and their chromatograms compared.…”

“…Heptelidic acid is a sesquiterpene discovered from Trichoderma virens (formerly Gliocladium virens), Chaetomium globosum, and Trichoderma viride, which has an antibiotic activity against anaerobic bacteria [10] and known for its GAPDH-inhibitory activity [12]. Recently it was reported that HA derivatives found from the culture medium of A. oryzae incubated with capsicin [13]. Thus, it was thought that the compound involved in the growth inhibition of T. halophilus may be HA produced by A. oryzae RIB40.…”