α-Pyrone and decalin derivatives from the marine-derived fungus Trichoderma harzianum PSU-MF79

Abstract

Two new compounds, one α-pyrone (trichoharzianone) and one decalin (trichoharzianin), along with eight known compounds including three decalins, two δlactones, two carboxylic acids and one isochroman were isolated from the marine-derived fungus Trichoderma harzianum PSU-MF79. The structures were determined by spectroscopic methods. The relative configuration of trichoharzianin was assigned based on NOEDIFF data and coupling constants whereas the absolute configurations were established by comparison of electronic circular dichroism data with those of the co-metabolites. Known (-)-massoia lactone exhibited mild antifungal activity against Cryptococcus neoformans ATCC90113 flucytosine-resistant, Candida albicans ATCC90028 and C. albicans NCPF3153 with MIC values of 128, 200 and 200 µg/mL, respectively, and weak cytotoxic activity against HCT-116 and MCF-7 cell lines with the respective IC50 values of 17 and 32 µM. In addition, it was noncytotoxic against noncancerous Vero cells with an IC50 value of >100 µM.

Strain improvement of Trichoderma harzianum for enhanced biocontrol capacity: Strategies and prospects

“…For example, several mutants obtained by UV mutagenesis exhibited increased Fusarium -inhibiting activity and produced two new compounds, including an isonitrile compound with broad antibiotic activity against fungi and bacteria ( Graeme-Cook and Faull, 1991 ; Faull et al, 1994 ). Third, mining of new isolates of T. harzianum from soil, plant root systems, and rhizomes allowed for the identification of new chemical derivatives with inhibitory activities, such as α-pyrone and decalin derivatives ( Nuansri et al, 2022 ), pentadecaibins ( van Bohemen et al, 2021 ), azaphilone D and E ( Zhang et al, 2020 ), harzianopyridone ( Ahluwalia et al, 2015 ), tandyukisin ( Yamada et al, 2014 ), trichosordarin A ( Liang et al, 2020 ), trichoharzianol ( Jeerapong et al, 2015 ), harzianic acid ( Vinale et al, 2009 ), and nafuredin C ( Zhao et al, 2020 ).…”

Structures and Biological Activities of Secondary Metabolites from the Trichoderma genus (Covering 2018–2022)

“…Botryane Sesquiterpenes. Five new botryane sesquiterpenes, characterized as 4,10,15-trihydroxybotry-1(9)-en (123), 15-o-acetylbotry-1(10),5(9)-dien-4-ol (124), 15-acetyldehydrobotrydienol (125), 10,15-di-o-acetyldehydrobotrydienol (126), 10-demethyldehydrobotrydien-1,15-diol (127), were isolated from the EtOAc extract prepared from the solid substrate fermentation of T. oligosporum. 72 Among these compounds, compound 127 exhibited cytotoxicity against the K562 cell line, with IC 50 values of 12.5 μM.…”

“…73 Compound 128 exhibited superior antifungal activities compared to carbendazim (a benzimidazole fungicide) against two Colletotrichum species and two carbendazim-resistant strains of B. cinerea, with MIC values ranging from 8 to 64 μg/mL. The structures of botryane sesquiterpenes (123)(124)(125)(126)(127)(128) and the representative bioactive compounds are shown in Figure S6 and Figure 3, respectively.…”

“…125 Compound 342 exhibited antifouling activity, with an EC 50 value of 29.8 μg/mL. Additionally, six naphthalene derivatives, including trichodermic acid C (343) and D (344), 126 trichoharzianin (345), 127 and tandyukisins G−I (346−348), 128 were discovered from the marine-derived fungus Trichoderma sp. HN-1.1, T. harzianum, PSU-MF79, and Trichoderma sp.…”

“…Two new polyketides, harzianumnones A (357) and B (358), have been charactierized as a pair of epimers, representing the first member of hydroanthraquinones from T. harzianum (XS-20090075). 130 Three α-pyrones, trichopyranone A (359), 55 nafuredin C (360), 103 and trichoharzianone (361), 127 were discovered from T. koningiopsis QA-3, T. harzianum D13, and T. harzianum PSU-MF79, respectively.…”