title: Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae.
abstract: The cytotoxicity of the extract obtained from Myrothecium roridum M10 and a characteristic (1)H 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.
authors: Institute for Organic and Biomolecular Chemistry, Georg-August-University Göttingen , Tammannstrasse 2, D-37077 Göttingen, Germany.
authors: Muhammad Abdul Mojid
authors: MA
authors: Mondol
authors: Department of Biotechnology, Bangabandhu Sheikh Mujibur Rahman Agricultural University , Gazipur 1706, Bangladesh.
authors: Musrat Zahan
authors: MZ
authors: Surovy
authors: Department of Biotechnology, Bangabandhu Sheikh Mujibur Rahman Agricultural University , Gazipur 1706, Bangladesh.
authors: M Tofazzal
authors: MT
authors: Islam
authors: Institute of Biotechnology and Drug Research , D-67663 Kaiserslautern, Germany.
authors: Anja
authors: A
authors: Schüffler
authors: Institute for Organic and Biomolecular Chemistry, Georg-August-University Göttingen , Tammannstrasse 2, D-37077 Göttingen, Germany.
authors: Hartmut
authors: H
authors: Laatsch
mesh_terms: D006999:Hypocreales / Q000737:chemistry*; D015394:Molecular Structure; D010838:Phytophthora / Q000166:cytology / Q000187:drug effects*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013170:Spores / Q000166:cytology / Q000187:drug effects*; D014255:Trichothecenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014675:Vegetables / Q000737:chemistry*
chemical_list: D010936:Plant Extracts; D014255:Trichothecenes
keywords: Phytophthora; antibiotic activity; roridin; structure elucidation; verrucarin