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Trivirensols: Selectively Bacteriostatic Sesquiterpene Trimers from the Australian Termite Nest-Derived Fungus Trichoderma virens CMB-TN16
journal contribution
posted on 2019-10-18, 01:29 authored by Wei-Hua Jiao, Angela A. Salim, Zeinab G. Khalil, Pradeep Dewapriya, Hou-Wen Lin, Mark S. Butler, Robert J. CaponThe termite nest-derived fungus Trichoderma virens CMB-TN16 cultivated on rice-based media
produced seven new first-in-class trimeric sesquiterpenes, trivirensols
A–G (11–17). Structures inclusive
of absolute configurations were assigned by detailed spectroscopic
analysis and biosynthetic considerations. Although trivirensols exhibit
no cytotoxicity to mammalian carcinoma cells, selected examples are
bacteriostatic against vancomycin-resistant Enterococcus faecalis (VRE). Structure–activity relationship (SAR) investigations
combined with in situ chemical stability studies
documented bacteriostatic activity for trivirensols A (11) and B (12) and the co-metabolite divirensols A (4), B (5), and G (10), all of which
share a common terminal butenolide. Significantly, SAR studies also
revealed bacteriostatic activity for trivirensols C (13) and G (17) and the co-metabolite divirensol C (6), all of which share a common hydrated butenolide terminal.
Of note, when exposed to VRE cell cultures, the hydrated butenolides 6, 13, and 17 undergo rapid in situ dehydration to corresponding butenolides, suggesting
hydrated butenolides are a pro-drug form of the butenolide VRE bacteriostatic
pharmacophore.
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SARVRE cell culturesvancomycin-resistant Enterococcus faecalisbacteriostatic activityco-metabolite divirensol Cfirst-in-class trimeric sesquiterpenesSelectively Bacteriostatic Sesquiterpene Trimerschemical stability studiesbutenolide VRE bacteriostatic pharmacophoretrivirensoltermite nest-derived fungus Trichoderma virens CMB-TN 16Australian Termite Nest-Derived Fungus Trichoderma virens CMB-TN 16
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