Iminimycin A, the new iminium metabolite produced by Streptomyces griseus OS-3601

• Published in: Journal of antibiotics Vol. 69; no. 8; pp. 611 - 615
• Main Authors: Nakashima, Takuji, Miyano, Rei, Iwatsuki, Masato, Shirahata, Tatsuya, Kimura, Toru, Asami, Yukihiro, Kobayashi, Yoshinori, Shiomi, Kazuro, Petersson, George A, Takahashi, Yōko, Ōmura, Satoshi
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 01.08.2016; Springer Nature; Nature Publishing Group
• Subjects: 631/154; 631/154/1435; Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Bacillus subtilis - drug effects; Bacteriology; Biomedical and Life Sciences; Bioorganic Chemistry; Biotechnology & Applied Microbiology; Chromatography, High Pressure Liquid - methods; Circular Dichroism; HeLa Cells; Humans; Immunology; Indolizidines - chemistry; Indolizidines - isolation & purification; Indolizidines - pharmacology; Inhibitory Concentration 50; Jurkat Cells; Life Sciences; Life Sciences & Biomedicine; Liquid chromatography; Magnetic Resonance Spectroscopy; Medicinal Chemistry; Metabolites; Microbiology; Micrococcaceae - drug effects; Organic Chemistry; original-article; Pharmacology & Pharmacy; Science & Technology; Silica; Streptomyces griseus - metabolism; Xanthomonas campestris - drug effects; MANGROMICINS; CIRCULAR-DICHROISM; GENOME SEQUENCE; ENDOPHYTIC ACTINOMYCETE; AGENTS; STRAIN; CULTURE BROTH; ALKALOIDS; FAMILY
• ISSN: 0021-8820; 1881-1469
• DOI: 10.1038/ja.2015.142

A new natural product, designated iminimycin A, was isolated from the cultured broth of a streptomycin-producing microbial strain, Streptomyces griseus OS-3601, via a physicochemical screening method using HP-20, silica gel and ODS column chromatographies and subsequent preparative HPLC. Iminimycin A is an indolizidine alkaloid, containing of an unusual iminium group and a cyclopropane ring with a triene side chain. The absolute configuration of iminimycin A was elucidated by NMR studies and electronic circular dichroism analysis. Iminimycin A shows anti-bacterial activity against Bacillus subtilis , Kocuria rhizophila and Xanthomonas campestris pv. orizae , and cytotoxic activity against HeLa S3 and Jurkat cells with IC 50 values of 43 and 36 μ M , respectively.