Bioactive Carotanes from Trichoderma virens

Abstract

Four new metabolites with carotane skeletons, trichocaranes A (1), B (2), C (3), and D (4), were isolated from Trichoderma virens and their structures established by the interpretation of NMR and mass spectroscopic data. The trichocaranes significantly inhibited the growth of etiolated wheat coleoptiles: 40% at 10(-4) M with 1 and 2 and 86% at 10(-3) M with 3.

Novel Sorbicillin Derivatives with an Unprecedented Carbon Skeleton from the Sponge‐Derived Fungus Trichoderma Species

“…[14] This class of hexaketides and dimers thereof have been found to exhibit a broad range of biological activities including inhibition of lipopolysaccharideinduced production of tumor necrosis factor alpha (TNF-α) in human monocytes, [15] radical scavenging [16] and cytotoxicity. [17] Results Accurate mass measurement and 1 H and 13 C NMR analysis of compound 1 showed it to have the molecular formula C 21 H 28 O 8 . Its 13 C NMR spectroscopic data allowed five of the eight elements of double-bond unsaturation to be attributed to three carbon-carbon double bonds and two carbonyl groups (Table 1); the molecule thus had to be tricyclic.…”

“…are noted for their diverse secondary metabolite chemistry that is not characterised by any clear pattern concerning the structural types encountered. To date, around 500 compounds have been reported from fungi belonging to this genus, including the bicyclic dodecanone koninginin G, [7] the carotane derivatives trichocaranes A-D, [8] and the cyclopentenones pentenocins A and B. [9] The current secondary metabolite investigation was focused on a marine Trichoderma sp., isolated from the Caribbean sponge Agelas dispar, collected from waters around the Island of Dominica, Windward Islands.…”

“…The fungus was cultivated on a solid glucose biomalt medium containing artificial sea water (ASW). Successive fractionation of the ethyl acetate extract by vacuum liquid chromatography (VLC) and HPLC yielded four novel sorbicillinoid polyketide derivatives, compounds 1-4, the known sorbicillinoid monomer vertinolide (5), [10] the dimers trichodimerol (6), [5,11] bislongiquinolide (7), [6] bisvertinol (8), [12] and the monomer rezishanone C (9), a possible product of a DielsAlder reaction between sorbicillinol and a dienophile not related to the sorbicillinoids (Figure 1). [13] [a] Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany E-mail: g.koenig@uni-bonn.…”

Secondary metabolites from species of the biocontrol agent Trichoderma

“…3), were isolated from T. virens, their relative structures being elucidated by spectral analysis. These compounds significantly inhibited the growth of etiolated wheat coleoptiles (Macias et al 2000).…”

Cyclopentane Sesquiterpenes from Fungi: Ocurrence-Bioactivity, Biosynthesis and Chemical Synthesis

“…Cyclonerotriol (2) was found in Fusarium culmorum [6] and Trichoderma virens [14]. Cyclonerodiol oxide (3), 10-epi-cyclonerodiol oxide (4) and 7-epi-cyclonerodiol oxide (5) were identified in the endophytic fungus Epicloë typhina [15,16].…”