Macrolide and phenolic metabolites from the marine-derived fungus Paraconiothyrium sp. VK-13 with anti-inflammatory activity

Abstract

Five new secondary metabolites, modiolides D-G (1-4) and 1-(2,5-dihydroxyphenyl)-3-methoxy-butan-1-one (8), one new natural product, 1-(2,5-dihydroxyphenyl)-3-hydroxybutan-1-one (7), along with three known compounds, modiolides A (5) and B (6), and 1-(2,5-dihydroxyphenyl)-2-buten-1-one (9) were isolated from a fermentation culture of the marine endophytic fungus Paraconiothyrium sp. VK-13. Their chemical structures were elucidated by the NMR and MS spectroscopic analysis as well as the modified Mosher's method. Compounds 7 and 9 inhibited the overproduction of proinflammatory mediators NO and PGE in LPS-stimulated RAW264.7 cells, with IC values ranging from 3.9 to 12.5 µM. The inhibitory effects of 7 and 9 on the release of NO and PGE were correlated with their significant suppression of iNOS and COX-2 protein expression, respectively. Furthermore, both compounds 7 and 9 inhibited the mRNA expression of proinflammatory cytokines, including TNF-α, IL-1β, IL-6, and IL-12, with IC values in a range of 2.4-12.5 µM.

Anti-leishmanial and Anti-inflammatory Agents from Endophytes: A Review

“…Further analysis revealed that these compounds significantly induce the suppression of iNOS and COX-2 protein expression. Furthermore, both compounds inhibited the mRNA expression of TNF-α, IL-1β, IL-6, and IL-12, with IC 50 values ranging from 2.4-12.5 µM [127]. Similarly, chaetoglobosin Fex (158), a compound isolated from marine-derived endophytic fungus Chaetomium globosum QEN-14 was also reported to significantly inhibit the production of TNF-α, IL-6 and monocyte chemotactic protein-1 (MCP-1) in peritoneal macrophages and murine macrophage cell line RAW264.7.…”

A Review of Anti-Inflammatory Compounds from Marine Fungi, 2000–2018

“…One new phenolic metabolite, 1-(2,5-dihydroxyphenyl)-3-hydroxybutan-1-one (105, Figure 18), along with 1-(2,5-dihydroxyphenyl)-2-buten-1-one (106, Figure 18), were found in the EtOAc extract of the marine endophytic fungus Paraconiothyrium sp. VK-13 [61]. 1-(2,5-dihydroxyphenyl)-3- hydroxybutan-1-one and 1-(2,5-dihydroxyphenyl)-2-buten-1-one displayed inhibitory effect against iNOS derived NO and COX-2 derived PGE 2 in LPS-stimulated RAW264.7 cells, with IC 50 values from 3.9 and 12.5 µM [61].…”

“…1-(2,5-dihydroxyphenyl)-3- hydroxybutan-1-one and 1-(2,5-dihydroxyphenyl)-2-buten-1-one displayed inhibitory effect against iNOS derived NO and COX-2 derived PGE 2 in LPS-stimulated RAW264.7 cells, with IC 50 values from 3.9 and 12.5 µM [61]. The anti-inflammatory effects of these compounds were attributed to the significant inhibition of the expression of iNOS and COX-2 proteins and the inhibition of mRNA expression of anti-pressure cytokines including TNF- α , IL-1 β , IL-6, and IL-12 [61]. From a marine crinoid collected in Xuwen, Zhanjing City, Guangdong Province, China, fungal strain Leptosphaerulina chartarum 3608, was selected for chemical study [62].…”

Secondary metabolites from a marine sponge‐associated fungus Xenomyrothecium sp. IMBC‐FP2.11

“…[7] However, chemical profile of the Xenomyrothecium genus has yet to be discovered so far. In our continuing search for secondary metabolites from the Vietnamese marinederived fungi, [8,9] we conducted a chemical investigation of a fungal strain Xenomyrothecium sp. IMBC-FP2.11 isolated from an unidentified sponge.…”