Sesquiterpene and Sorbicillinoid Glycosides from the Endophytic Fungus Trichoderma longibrachiatum EN-586 Derived from the Marine Red Alga Laurencia obtusa

Abstract

An unusual sesquiterpene glycoside trichoacorside A (1) and two novel sorbicillinoid glycosides sorbicillisides A (2) and B (3), together with a known compound sorbicillin (4), were isolated and identified from the culture extract of an endophytic fungus Trichoderma longibrachiatum EN-586, obtained from the marine red alga Laurencia obtusa. Trichoacorside A (1) is the first representative of a glucosamine-coupled acorane-type sesquiterpenoid. Their structures were elucidated based on detailed interpretation of NMR and mass spectroscopic data. The absolute configurations were determined by X-ray crystallographic analysis, chemical derivatization, and DP4+ probability analysis. The antimicrobial activities of compounds 1–4 against several human, aquatic, and plant pathogens were evaluated.

Marine natural products

“…254 Culture of a Trametes strain yielded spiromeroterpenoids 793 and 794 (ref. 255) and cultures of various Trichoderma strains were the source of trichothecanes 795 – 798 , 256 α-pyrone 799 and decalin 800 , 257 sesquiterpene glycoside 801 and sorbicillinoid glycosides 802 and 803 , 258 β-carboline alkaloids 804 – 807 ( 805 and 806 , known synthetics but new NPs), 259 and polyketides 808 , 809 , 260 810 – 814 . 261 …”

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

“…49 Trichoacorside A (135), isolated from T. longibrachiatum EN-586, was characterized as the first example of a glucosamine-coupled acorane-type sesquiterpenoid, and the bioassay results revealed that compound 135 demonstrated a broad spectrum of antimicrobial activity against methicillinresistant Staphylococcus aureus and the aquatic pathogenic bacterium V. harveyi, as well as multiple plant-pathogenic fungi. 75 The structures of acorane sesquiterpenes 133−135 and the representative bioactive compounds are shown in Figure S6 and Figure 3, respectively. Drimane Sesquiterpenes.…”

“…109 Eight new sorbicillinoids, saturnispols A−H (262−269), were isolated from the endophytic fungus T. saturnisporum DI-IA originating from the marine sponge Dictyonellaincise. 110 A series of new sorbicillinoid derivatives and a new natural compound, including spirosorbicillinol D (294), 2′,3′-dihydroepoxysorbicillinol (295), 113 trichoreesin A (296), 114 2,3dihydro 2-hydroxyvertinolide(297), (−)-trichodermatone (298), 115 and sorbicillisides A (299) and B (300), 75 were discovered from T. longibrachiatum SFC100166, T. reesei Z56-8, Trichoderma sp. FM652 and T. longibrachiatum EN-586, respectively.…”

“…Compound 292 was subjected to testing against the three cancer cell lines A549, MCF-7, and HCT 116 cell lines and exhibited inhibition activity with IC 50 values of 5.1, 9.5, and 13.7 μM, respectively. A series of new sorbicillinoid derivatives and a new natural compound, including spirosorbicillinol D ( 294 ), 2′,3′-dihydro-epoxysorbicillinol ( 295 ), trichoreesin A ( 296 ), 2,3-dihydro 2-hydroxyvertinolide­( 297 ), (−)-trichodermatone ( 298 ), and sorbicillisides A ( 299 ) and B ( 300 ), were discovered from T. longibrachiatum SFC100166, T.…”

Use of CRISPR‐Cas tools to engineer Trichoderma species

“…Moreover, relatively little is known regarding the nature of biosynthetic gene clusters. Thus, the CRISPR‐Cas system would appear to be an ideal platform for mining novel natural products associated with cryptic and uncharacterized biosynthetic gene clusters from these newly isolated Trichoderma species (Wang et al, 2022 ).…”