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Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae

Mondol, Muhammad Abdul Mojid, Surovy, Musrat Zahan, Islam, M. Tofazzal, Schuffler, Anja, Laatsch, Hartmut
Journal of agricultural and food chemistry 2015 v.63 no.40 pp. 8777-8786
Candida albicans, Myrothecium roridum, Phytophthora nicotianae, Rhizomucor miehei, cytotoxicity, diketopiperazines, metabolites, rice, roridins, spectroscopy, zoospores
The cytotoxicity of the extract obtained from Myrothecium roridum M10 and a characteristic 1H signal at δH ∼8 led to the assumption that verrucarin/roridin-type compounds were present. Upscaling on rice medium led to the isolation of four new metabolites: verrucarins Y (1) and Z (6) (macrocyclic trichothecenes), bilain D (12) (a diketopiperazine derivative), and hamavellone C (14) (an unusual cyclopropyl diketone). In addition, nine known trichothecenes [verrucarin A (3), 16-hydroxyverrucarin A (5), verrucarin B (7), 16-hydroxyverrucarin B (8), verrucarin J (2), verrucarin X (4), roridin A (9), roridin L-2 (10), and trichoverritone (11)] and a bicyclic lactone [myrotheciumone A (15)] were identified. Their structures and configurations were determined by spectroscopic methods, published data, Mosher’s method, and considering biosyntheses. Some trichothecenes showed motility inhibition followed by lysis of the zoospores against devastating Phytophthora nicotianae within 5 min. Compounds 2, 3, 7, and 9 also exhibited potent activities against Candida albicans and Mucor miehei.