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.
Highlights
Trichoderma longibrachiatum EN-586, which was obtained from the inner tissue of the marine red alga Laurencia obtusa, attracted our attention due to its unique secondary metabolite profile
Chemical investigation on the culture extract of T. longibrachiatum EN-586 resulted in the isolation and identification of an unusual sesquiterpene glycoside, trichoacorside
Thin-layer chromatography (TLC) plates were carried out using precoated silica gel plates GF254 (Qingdao Haiyang Chemical Factory) and analytical HPLC were performed using a Dionex system equipped with P680 pump, ASI-100 automated sample injector, and UVD340U multiple wavelength detector controlled by Chromeleon software
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. Marine-derived fungi have shown great potential for structurally unique secondary metabolites with interesting biological and pharmacological properties [6,7], among which algicolous fungi represent an important source of active metabolites [7,8]. Trichoderma longibrachiatum EN-586, which was obtained from the inner tissue of the marine red alga Laurencia obtusa, attracted our attention due to its unique secondary metabolite profile. Chemical investigation on the culture extract of T. longibrachiatum EN-586 resulted in the isolation and identification of an unusual sesquiterpene glycoside, trichoacorside. 586 resulted in the isolation and identification of 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). Of wecompounds report the chemical investigation of a structure elucidation, andsorbicillin biological (4). Rice-based culture of T. longibrachiatum EN-586 including the isolation, structure elucidation, and biological
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