Neural anti-inflammatory sesquiterpenoids from the endophytic fungus Trichoderma sp. Xy24

Abstract

Three new sesquiterpenoids trichoacorenols B-C and cyclonerodiol B (1-3), along with three known ones (4-6), were isolated from the mangrove plant endophytic fungus Trichoderma sp. Xy24 using various column chromatography techniques. The structures of these compounds were determined on the basis of extensive spectroscopic data analyses. Compounds 1, 2, 4, and 5 were four acorane sesquiterpenes, 3 and 6 were two monocyclic sesquiterpenediols. Compounds 3 and 5 exhibited significant neural anti-inflammatory activity by inhibiting LPS-induced NO production in BV2 cells with the inhibitory rates of 75.0% and 39.2% at 0.1 μM, respectively, which are more potent than curcumin, a positive control with the inhibitory rate of 21.1% at 0.1 μM.

Terpenoids From the Coral-Derived Fungus Trichoderma harzianum (XS-20090075) Induced by Chemical Epigenetic Manipulation

“…Mosher's method (Cao et al, 2014) was tried to determine the absolute configuration of C-7 but failed. Fortunately, a literature survey revealed that the coisolated cyclonerane-type compounds (4-9) and many other similar natural compounds have been reported the same absolute configurations as 2S,3R,6R,7R (Hanson et al, 1975;Kasitu et al, 1992;Li et al, 2007;Wu et al, 2012;Xie et al, 2013;Zhang et al, 2017;Fang et al, 2018;Song et al, 2018). Therefore, based on the biogenetic considerations, compound 3 was proposed to have the same absolute configuration (2S,3R,6R,7R) as the co-isolated compound 9, which was also supported by their similar OR between 3 ([α] 22 D -29.9 (c 1.00, CHCl 3 )) and 9 ([α] 22 D -26.6 (c 1.00, CHCl 3 ); lit.…”

Prospective Leads from Endophytic Fungi for Anti-Inflammatory Drug Discovery

“…1α-isopropyl-4α,8-dimethylspiro dec-8-ene-3β,7αdiol (26) Trichoderma sp. Xy24 Xylocarpus granatum [15] 10.…”

“…They are characterized by a highly substituted per hydro-isoindolone moiety to which a macrocyclic ring like a carbocycle, a lactone, or a cyclic carbonate is fused [54]. Four AI cytochalasan derivatives [cytochalasin J (12) and H (13), yamchaetoglobosin A (14), and phomopchalasin C (15)] from endophytic fungal sources were reported (▶ Fig. 2).…”

“…Periconianone A (20) and periconianone B (21) were found to inhibit LPS-induced NO production in mouse microglia BV2 cells with IC 50 values of 0.15 and 0.38 µM, respectively. Nevertheless, all the sesquiterpenes were proven to possess good AI activity (▶ Table 2) [15,31,38,39,47].…”

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

“…In another investigation, three new sesquiterpenoids, trichoacorenols B-C and cyclonerodiol B, along with three known ones, isolated from the mangrove plant endophytic fungus Trichoderma sp. Xy24 were reported to exhibit varying degree of anti-inflammatory activity with cyclonerodiol B (153) and (1R,2R,4S,5R,7S)-4-isopropyl-1,8-dimethylspiro [4.5]dec-8-ene-2,7-diol (154) being more potent than curcumin, used as positive control [125].…”