New Sorbicillinoids with Tea Pathogenic Fungus Inhibitory Effect from Marine-Derived Fungus Hypocrea jecorina H8

Abstract

Four new dimeric sorbicillinoids (1–3 and 5) and a new monomeric sorbicillinoid (4) as well as six known analogs (6–11) were purified from the fungal strain Hypocrea jecorina H8, which was obtained from mangrove sediment, and showed potent inhibitory activity against the tea pathogenic fungus Pestalotiopsis theae (P. theae). The planar structures of 1–5 were assigned by analyses of their UV, IR, HR-ESI-MS, and NMR spectroscopic data. All the compounds were evaluated for growth inhibition of tea pathogenic fungus P. theae. Compounds 5, 6, 8, 9, and 10 exhibited more potent inhibitory activities compared with the positive control hexaconazole with an ED50 of 24.25 ± 1.57 µg/mL. The ED50 values of compounds 5, 6, 8, 9, and 10 were 9.13 ± 1.25, 2.04 ± 1.24, 18.22 ± 1.29, 1.83 ± 1.37, and 4.68 ± 1.44 µg/mL, respectively. Additionally, the effects of these compounds on zebrafish embryo development were also evaluated. Except for compounds 5 and 8, which imparted toxic effects on zebrafish even at 0.625 μM, the other isolated compounds did not exhibit significant toxicity to zebrafish eggs, embryos, or larvae. Taken together, sorbicillinoid derivatives (6, 9, and 10) from H. jecorina H8 displayed low toxicity and high anti-tea pathogenic fungus potential.

Marine natural products

“…298 Sorbicinol derivatives 832 , 833 , 834 and two dimeric sorbicinols 835 and 836 were isolated from sediment-derived Hypocrea jecorina . 299 Sediment-derived Nigrospora camelliae-sinensis yielded two simple diketopiperazines nigrosporaamides A 837 and B 838 . 300 A thiodiketopiperazine, adametizine C 839 and alkane derivatives 840 – 844 were reported from sediment-derived Penicillium ludwigii .…”

Use of CRISPR‐Cas tools to engineer Trichoderma species

“…Recently, researchers have begun to focus on Trichoderma species isolated from specific habitats, which are abundant but rarely investigated fungal sources to produce a wide range of natural products with diverse bioactivities (Liu, Song et al, 2022 ; Liu, Xu et al, 2022 ). Moreover, relatively little is known regarding the nature of biosynthetic gene clusters.…”

“…In Pichia pastoris , CRISPRa/CRISPRi technology has facilitated the more precise regulation of gene expression. Furthermore, when used in conjunction with synthetic promoters in P. pastoris , CRISPRa‐based gene expression represents a novel “plug‐and‐play” platform that can be applied to produce customized hosts with high‐level expression that responds to defined signals (Liu, Song et al, 2022 ; Liu, Xu et al, 2022 ). However, CRISPRa/CRISPRi systems are yet to be developed for editing the Trichoderma genome.…”

Hyposterolactone A, a 3α‐Hydroxy Steroidal Lactone from the Deep‐Sea‐Derived FungusHypocreasp. ZEN14

“…[3][4][5][6][7] The Hypocrea (also called Trichoderma) species are soilborne or wood-decaying fungi known as opportunistic pathogens of immunocompromised humans as well as producers of industrial enzymes and biocontrol agents against plant pathogens. [8] Up to now, a broad spectrum of secondary metabolites were isolated from the species, including sorbicillinoids, [9] sesquiterpenes, [10,11] alkaloids, [12] polyketides, [13] naphthalenes, [14] and so on. These compounds exhibited various bioactivities, including anticancer, [11,14,15] antimicrobial, [9,11,16] and antioxidant etc.…”

“…[8] Up to now, a broad spectrum of secondary metabolites were isolated from the species, including sorbicillinoids, [9] sesquiterpenes, [10,11] alkaloids, [12] polyketides, [13] naphthalenes, [14] and so on. These compounds exhibited various bioactivities, including anticancer, [11,14,15] antimicrobial, [9,11,16] and antioxidant etc. [17] In our unremitting investigation of bioactive secondary metabolites from deep-sea-derived fungi, we have taken advantage of the OSMAC strategy to explore a wide range of fungal species.…”