title: Induced Production of Halogenated Epidithiodiketopiperazines by a Marine-Derived Trichoderma cf. brevicompactum with Sodium Halides.
abstract: Marine-derived Trichoderma sp. TPU199 (cf. T. brevicompactum) produced gliovirin (1), pretrichodermamide A (2), and trichodermamide A (3) in a freshwater medium. Compounds 1 and 2 are rare epidithiodiketopiperazines possessing an unusual disulfide linkage. In the seawater medium, the strain biosynthesized the 5-chloro-5-deoxy derivatives (4 and 5) of 3 and 2. The production of 5 was proportional to the concentration of seawater (NaCl). Therefore, 5-bromo-5-deoxy (6) and 5-deoxy-5-iodo (7) derivatives were biosynthesized in the freshwater media supplemented with NaBr and NaI, respectively. The structure of a new iodo derivative (7) was elucidated on the basis of its spectroscopic data.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University , Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Yamazaki
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University , Aoba-ku, Sendai 981-8558, Japan.|Research Institute, University of Pembangunan Indonesia , Bahu, Manado 95115, Indonesia.
authors.forename: Henki
authors.initials: H
authors.lastname: Rotinsulu
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University , Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Reika
authors.initials: R
authors.lastname: Narita
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University , Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Takahashi
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University , Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Michio
authors.initials: M
authors.lastname: Namikoshi
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004151:Dipeptides / Q000737:chemistry / Q000302:isolation & purification*; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D019029:Palau; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification*; D000461:Rhodophyta / Q000382:microbiology; D012965:Sodium Chloride / Q000032:analysis; D014242:Trichoderma / Q000737:chemistry*
chemical_list: D004151:Dipeptides; D010879:Piperazines; C583251:epidithiodiketopiperazine; C519044:pretrichodermamide A; C476747:trichodermamide A; D012965:Sodium Chloride; C036710:gliovirin