Characterization of cyclonerodiol isolated from corn infested by fusarium moniliforme sheld.: One‐ and two‐dimensional ¹H and ¹³C NMR study

Abstract

A metabolite extracted from maize culture was identified as cyclonerodiol. Its 1H and 13C NMR spectra have been fully analysed, and some literature assignments have been reversed.

Nitrogenous cyclonerane sesquiterpenes from an algicolous strain of Trichoderma asperellum

“…Cyclonerane-type sesquiterpenes, represented by the first member cyclonerodiol, 1 with a monocyclic carbon skeleton have been found in a broad spectrum of fungal species, such as those of the genera Ascotricha, 2 Aspergillus, 3 Botrytis, 4 Epichloe, [5][6][7] Fusarium (Gibberella), [8][9][10][11] Myrothecium, 12 Paecilomyces, 13 Trichoderma, [14][15][16][17][18][19] and Trichothesium. 1 Several molecules possess antibacterial, 3,14 antifungal, [5][6][7] and antiinflammatory 17 activities and have also attracted much attention for chemical synthesis, 20 biosynthesis, 21 and biotransformation.…”

“…23,24 However, most of the hydroxamic acids possess a N 5 -acyl-N 5 -hydroxyornithine structural unit, 25,26 and none of them are derived from cycloneranes. During our ongoing search for new and bioactive secondary metabolites from marine algicolous Trichoderma fungi, [14][15][16] a detailed examination of the endophytic T. asperellum A-YMD-9-2 obtained from the marine red alga Gracilaria verrucosa led to the iso-lation of eleven cyclonerane derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11) (Fig. 1), especially including two unexpected hydroxamic acids (1 and 2) and other six nitrogenous derivatives (3)(4)(5)(6)(7)(8).…”

Three nitrogen-containing metabolites from an algicolous isolate of Trichoderma asperellum

“…On account of the NOE correlation between H-2′ and H 2 -4′ and the similar NMR data with those of deoxycyclonerins (Song et al 2019), the E-geometry was appointed to the vinyl group at C-2′. The relative configurations at C-2, C-3, C-6, and C-7 were certified by the identical 1 H and 13 C NMR data with those of cyclonerane derivatives (Langhanki et al 2014;Laurent et al 1990;Song et al 2018b). The absolute configurations at C-2, C-3, C-6, and C-7 were deduced to be uniform with its analogues according to biogenic consideration (Song et al 2019).…”

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

“…Compound (1) has been also identified in a number of other fungus species, namely, a marine algicolous Botrytis sp [4], Epicloë festucae a endophytic fungus from Festuca sp [5], Fusarium culmorum [6], different species of Fusarium, [7], F. fujikuroi [8], F. moniliforme [9], two marine Mirothecium sp [10], the marine Trichoderma reesei [11], the parasitic fungi Trichoderma koningii [12] and the parasitic wheat root fungus Trichoderma harzianum [13].…”

“…[4,[5][6][7][8][9][10][11][12][13] C 2 ]-Mevalonolactone(25) was prepared via LDAinduced condensation of labelled ethyl acetate with 4,4-dimethoxybutan-2-one, reduction of the ester with lithium aluminium hydride, hydrolysis of the acetal group and oxidation of the resulting aldehyde with bromine. The incubation of [4,5-13 C 2 ]-mevalonolactone with Fusarium culmorum led then to the isolation of cyclonerodiol and cyclonerotriol, isotopically labelled in the proper positions as shown inFig.…”