Biologically Active Eremophilane-Type Sesquiterpenes from Camarops sp., an Endophytic Fungus Isolated from Alibertia macrophylla

Abstract

Two new eremophilane-type sesquiterpenes, xylarenones F (3) and G (4), have been isolated from solid substrate cultures of a Camarops sp. endophytic fungus isolated from Alibertia macrophylla, together with the known compounds xylarenones C (1) and D (2). The structures and relative configurations of 1-4 were elucidated by extensive NMR and HRESIMS spectroscopic analysis. Due to their effects on the respiratory burst of neutrophils, which included inhibition of the reactive oxygen species production, these sesquiterpenes exhibited potential anti-inflammatory and antioxidant properties.

Endophytes from medicinal plants and their potential for producing indole acetic acid, improving seed germination and mitigating oxidative stress

“…Endophytes also possess the ability to detoxify reactive oxygen species (ROS). The superoxide anion scavenging potential of our endophytes is consistent with the investigation reported by Gubiani et al (2014) and Zhao et al (2014). Gubiani et al (2014) found four biologically active metabolites in the CF of the endophytic fungus Camarops sp., which was isolated from Alibertia macrophylla.…”

“…The superoxide anion scavenging potential of our endophytes is consistent with the investigation reported by Gubiani et al (2014) and Zhao et al (2014). Gubiani et al (2014) found four biologically active metabolites in the CF of the endophytic fungus Camarops sp., which was isolated from Alibertia macrophylla. These metabolites scavenge the superoxide anion indirectly via nicotinamide adenine dinucleotide phosphate (NADPH) oxidase inhibition in neutrophils and exhibit anti-inflammatory and antioxidant potentials.…”

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

“…mangrove plant [92] Xylarenones Xylaria sp. Torreya jackii [93] Camarops sp Alibertia macrophylla [94,95] Data introduced in the above tables are eventually incomplete, due to the ongoing addition of novel findings concerning the direct and indirect influence of endophytic fungi on the composition of essential oils, and ensuing effects on their biological activities. The resulting complex framework and the intriguing applicative perspectives are possibly indicative of the opportunity of a dedicated review for such a hot research topic.…”

Rearranged Sesquiterpenes and Branched Polyketides Produced by the Endophyte Camarops sp.

“…Compounds 5, 6 and 7 were identified as (2E,4S)-2,4dimethyloct-2-enoic acid, xylarenone C and xylarenone D, respectively, based on the analysis of spectroscopic data and comparison with reports in the literature (Rukachaisirikul et al, 2009; Alcaraz et al, 1999;Yang et al, 2010;Zhang et al, 2012;Gubiani et al, 2014;Oliveira et al, 2011;Waalboer et al, 2009). The absolute configuration of compound 5 was identical to that of the known compound on the basis of their similar specific rotations (Rukachaisirikul et al, 2009;Alcaraz et al, 1999).…”

“…Its homologues have been reported as constituents of the side chain of different metabolites, including xylarenal A and B (Waalboer et al, 2009), and xylarenones C, D, E, F and G (Gubiani et al, 2014;Oliveira et al, 2011). Xylarenones C, D, E, F and G were isolated in our previous work with the endophyte Camarops sp., and were found to possess potent antioxidant and anti-inflammatory activities besides exhibiting inhibitory activity of pepsin and subtilisin enzymes (Gubiani et al, 2014;Oliveira et al, 2011). The strong AChE inhibitory activity observed for compounds 6 and 7 implies that the side chain of these metabolites is related to their AChE inhibitory activity.…”