Characterization of metabolites from cultures of Cellulosimicrobium cellulans

Abstract

Chemical investigation of cultures of Cellulosimicrobium cellulans led to the isolation of six metabolites. They were identified as anthranilic acid (1), cyclo-(dehydroala-L-Leu) (2), cyclo-(L-Pro-L-Tyr) (3), L-phenylalanine (4), cyclo-(L-Pro-L-Leu) (5), and cyclo-(L-Pro-L-Val) (6) based on spectroscopic methods such as MS, and NMR. To the best of our knowledge, this study represents the first chemical investigation of cultures of C. cellulans. The antifungal activities of 1-6 were evaluated against a variety of plant pathogens. The antifungal activities of 1 against plant fungal pathogens were evaluated for the first time in this work. Anthranilic acid (1) was found to possess the most potent antifungal activities against Pythium ultimum with an MIC of 1.25 µg/mL.

Efficacy of metabolites of a Streptomyces strain (AS1) to control growth and mycotoxin production by Penicillium verrucosum, Fusarium verticillioides and Aspergillus fumigatus in culture

“…The production of these compounds by other Streptomyces species and bacteria such as Bacillus sp. N strain, Pseudomonas aurantiaca and Cellulosimicrobium cellulans has been reported previously (Buedenbender et al 2018;Gwee Kyo et al 2011;Kumar et al 2013;Li et al 2006;Park and Shim 2014;Park et al 2008, Wattana-Amorn et al 2016. The other compounds found were mainly cyclic ionophores which were present in very low amounts and thus probably did not directly contribute to the antifungal activity.…”

“…The other compounds found were mainly cyclic ionophores which were present in very low amounts and thus probably did not directly contribute to the antifungal activity. Previous studies have shown variable results in terms of efficacy depending on the target fungal genera or species including Aspergillus, Fusarium, Penicillium, Rhizoctonia and Candida species (Gwee Kyo et al 2011;Kumar et al 2013;Park and Shim 2014;Park et al 2008). Although brevianamide F was a relatively minor component, its potential role in antifungal activity has not been previously described.…”

Nitrogenous Compounds from the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11

“…The structures of 2, 3, 5-10 were determined as thymine [15], cyclo-(dehyd Val) [16,17], cyclo-(dehydroAla-L-Leu) [18], cyclo-(dehydroAla-L-Phe) [19], cyclo-Phe) [20], cyclo-(L-Leu-L-Phe) [20], cyclo-(L-Trp-L-Ile) [21] and cyclo-(L-Trp-L-P respectively, by comparing their NMR and specific OR data (Table 2) with tho 1). The two NH signals (δ H 8.34, (1H, br s), δ H 10.53, (1H, s)) combined with two carbonyls indicated the diketopiperazine structure of 4.…”

“…The absolute configuration of 4 was proposed to be same as 2). The structures of 2, 3, 5-10 were determined as thymine [15], cyclo-(dehydroAla-L-Val) [16,17], cyclo-(dehydroAla-L-Leu) [18], cyclo-(dehydroAla-L-Phe) [19], cyclo-(L-Val-L-Phe) [20], cyclo-(L-Leu-L-Phe) [20], cyclo-(L-Trp-L-Ile) [21] and cyclo-(L-Trp-L-Phe) [22], respectively, by comparing their NMR and specific OR data (Table 2) with those in the literature. All the isolated compounds were evaluated for their antibacterial activities against a panel of bacteria, including four pathogenic bacteria, E. coli, S. aureus, P. aeruginosa and B. subtilis, and nine marine fouling bacteria, P. fulva, A. hydrophila, A. salmonicida, V. anguillarum, V. harveyi, P. halotolerans, P. angustum, E. cloacae and E. hormaechei, and cytotoxic activities against five human cancer cell lines A549, PANC-1, HCT116, HepG2 and MDA-MB-231.…”

“…The absolute configuration of 4 was proposed to be same as 3 and 5 according to biogenetic perspective and their similar specific optical rotation (OR) data ([α] 20 D −19.3 (c 0.18, CH 3 OH) of 4 vs [α] 20 D −10.5 (c 0.18, CH 3 OH) of 3 and [α] 20 D −78.1 (c 0.18, CH 3 OH) of 5, Table2). The structures of 2, 3, 5-10 were determined as thymine[15], cyclo-(dehydroAla-L-Val)[16,17], cyclo-(dehydroAla-L-Leu)[18], cyclo-(dehydroAla-L-Phe)[19], cyclo-(L-Val-L-Phe)[20], cyclo-(L-Leu-L-Phe)[20], cyclo-(L-Trp-L-Ile)[21] and cyclo-(L-Trp-L-Phe)[22], respectively, by comparing their NMR and specific OR data (Table2) with those in the literature.…”