Anti-inflammatory compounds from the mangrove endophytic fungus Amorosia sp. SCSIO 41026

Abstract

Three new chlorinated compounds, including two propenylphenol derivatives, chlorophenol A and B (1 and 2), and one benzofuran derivative, chlorophenol C (3), together with 16 known compounds, were isolated from the mangrove endophytic fungus Amorosia sp. SCSIO 41026. 7-Chloro-3,4-dihydro-6,8-dihydroxy-3-methylisocoumarine (4) and 2,4-dichloro-3-hydroxy-5-methoxy-toluene (5) were obtained as new natural products. Their structures were elucidated by physicochemical properties and extensive spectroscopic analysis. Compounds 1, 4, 7, 9, 13, 15, 16, and 19 possessed inhibitory effects against the excessive production of nitric oxide (NO) and pro-inflammatory cytokines in lipopolysaccharide (LPS)-challenged RAW264.7 macrophages without obvious cytotoxicity. Moreover, 5-chloro-6-hydroxymellein (13) further alleviated the pathological lung injury of LPS-administrated mice and protected RAW264.7 macrophages against LPS-induced inflammation through PI3K/AKT pathway in vivo. Our research laid the foundation for the application of compound 13 as a potential anti-inflammatory candidate.

Acremochlorin O and Other Prenylated Chlorophenol Antimicrobial Metabolites from the Fungus Acremonium sp. Strain MNA-F-1

“…A literature search of 1 based on the interpreted structural features proposed it to be a prenylated chlorophenol merosesquiterpenoid derivative and its spectral data revealed a close resemblance to those reported for ascofuranol [5]. The main difference in spectral data between 1 and ascofuranol was the presence of an additional acetyl group in 1 as indicated by 1 H and 13 C NMR data (Table 1) explaining its higher molecular weight by 42 atomic units compared to ascofuranol.…”

“…The 13 C NMR, HMBC and HSQC spectra of 1 (Table 1, Figure 2) disclosed the presence of twenty-five carbon resonances that can be differentiated into two carbonyl carbon atoms at δC 193.4, designated as an aldehyde group based on its direct correlation to a deshielded singlet proton signal at δH 10.15, and at δC 170.8 that was designated as an acetyl group based on its HMBC correlation to a singlet methyl group (δH 2.08). In addition, the 13 C NMR spectral data of 1 (Table 1) showed the presence of nine other unprotonated sp 2 carbons (δC 162. 3, 156.6, 137.8, 136.5, 134.3, 114.5, 113.7, 113.4, 81.9), four methine carbon atoms (δC 127.5, 121.2, 80.9, 79.6), four secondary (δC 39.2, 37.…”

Elucidating the molecular mechanisms underlying anti-inflammatory effects of Morchella esculenta in the arachidonic acid metabolic pathway by network pharmacology and molecular docking

“…At present, the metabolites of fungi have become the main source of anti-inflammatory lead compounds because of their novel structure, low toxicity and significant inhibitory effect 36 . Many new compounds have been obtained from plant endophytic fungi, which can inhibit the excessive production of endotoxin-induced NO and pro-inflammatory cytokines IL-6, tumor necrosis factor-α and monocyte chemoattractant protein-1 at both gene and protein levels 37 . The compounds isolated from algae-producing fungi could inhibit the excessive production of NO and pro-inflammatory cytokines in lipopolysaccharide-treated RAW264.7 macrophages in a dose-dependent manner without any cytotoxicity 38 .…”

New Chlorinated Metabolites and Antiproliferative Polyketone from the Mangrove Sediments-Derived Fungus Mollisia sp. SCSIO41409

“…Chlorinated metabolites, as a key part of the halogenated compounds, have demonstrated a wide range of significant activities. Due to the high concentration of chloride ions in mangrove ecosystem, many chlorinated compounds have been excavated from mangrove-derived microorganisms [ 9 , 10 , 11 ]. In this study, two new chlorinated metabolites, 1 and 3 , were isolated from mangrove sediments-derived fungus.…”

“…Research on secondary metabolites from mangrove sediments-derived microbes has yielded many natural products with novel structures and significant pharmacological activities [ 5 , 6 , 7 , 8 ]. In particular, halogenated compounds obtained from mangrove-derived microbes, especially chlorine-containing metabolites, have received a great deal of attention [ 9 , 10 , 11 ].…”