HYDANTOCIDIN: A NEW COMPOUND WITH HERBICIDAL ACTIVITY FROM Streptomyces hygroscopicus

• Published in: Journal of antibiotics Vol. 44; no. 3; pp. 293 - 300
• Main Authors: NAKAJIMA, MUTSUO, ITOI, KAZUKO, TAKAMATSU, YASUYUKI, KINOSHITA, TAKESHI, OKAZAKI, TAKAO, KAWAKUBO, KATSUHIKO, SHINDO, MASAHIRO, HONMA, TOYOKUNI, TOHJIGAMORI, MANABU, HANEISHI, TATSUO
• Format: Journal Article
• Language: English
• Published: Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1991; Japan Antibiotics Research Association
• Subjects: Agronomy. Soil science and plant productions; Animals; Biological and medical sciences; Chemical control; Culture Media; Fundamental and applied biological sciences. Psychology; Herbicides - chemistry; Herbicides - isolation & purification; Herbicides - pharmacology; Herbicides - toxicity; Hydantoins - chemistry; Hydantoins - pharmacology; Hydantoins - toxicity; Magnetic Resonance Spectroscopy; Mice; Microscopy, Electron, Scanning; Molecular Structure; Parasitic plants. Weeds; Phytopathology. Animal pests. Plant and forest protection; Plants - drug effects; Poecilia; Seeds - drug effects; Soil Microbiology; Spectrophotometry, Infrared; Spores, Bacterial - metabolism; Spores, Bacterial - ultrastructure; Streptomyces - classification; Streptomyces - growth & development; Streptomyces - metabolism; Streptomyces - ultrastructure; Streptomyces hygroscopicus; Weeds; Monocotyledones; Molecular structure; Nitrogen heterocycle; Perennial plant; Identification; Chemical isolation; Oxygen heterocycle; Actinomycetales; Dicotyledones; Angiospermae; Bicyclic compound; Bacteria; Streptomyces hygroscopicus; Streptomycetaceae; Weed; New product; Biochemical compound; Annual plant; Hydantoins; Biological activity; Herbicide; Microbial herbicide; Antibiotic; Microbial origin; Actinomycetes; Spermatophyta
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.44.293

Hydantocidin, a new compound with potent non-selective herbicidal activity, was found in a submerged culture of Streptomyces hygroscopicus SANK 63584. It was isolated from the culture filtrate by the following successive treatments comprised of activated carbon, Diaion HP-20, Dowex 50WX4, and Avicel column chromatographies. Finally it was crystallized as colorless needles from acetone. The molecular formula, C7H10N2O6, was determined by analyses of HRFAB mass spectrum in conjunction with 13C NMR spectrometry. The structural elucidation revealed that it has a unique structure with a spiro-bond between ribose and hydantoin moieties in the molecule. The characteristic herbicidal activities against annuals as well as perennials, including monocotyledonous and dicotyledonous weeds, were observed.