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

Takuji Nakashima; Rei Miyano; Masato Iwatsuki; Tatsuya Shirahata; Toru Kimura; Yukihiro Asami; Yoshinori Kobayashi; Kazuro Shiomi; George A. Petersson; Yoko Takahashi; Satoshi Omura

doi:10.1038/ja.2015.142

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

Takuji Nakashima^*, Rei Miyano, Masato Iwatsuki, Tatsuya Shirahata, Toru Kimura, Yukihiro Asami, Yoshinori Kobayashi, Kazuro Shiomi, George A. Petersson, Yoko Takahashi, Satoshi Omura

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

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 IC₅₀ values of 43 and 36 μM, respectively.

Original language	English
Pages (from-to)	611-615
Number of pages	5
Journal	Journal of Antibiotics
Volume	69
Issue number	8
DOIs	https://doi.org/10.1038/ja.2015.142
Publication status	Published - 2016 Aug 1
Externally published	Yes

ASJC Scopus subject areas

Pharmacology
Drug Discovery

Access to Document

10.1038/ja.2015.142

Cite this

@article{56d21f9c5546402ba0904d6cbd35f4e1,

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

abstract = "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 IC50 values of 43 and 36 μM, respectively.",

author = "Takuji Nakashima and Rei Miyano and Masato Iwatsuki and Tatsuya Shirahata and Toru Kimura and Yukihiro Asami and Yoshinori Kobayashi and Kazuro Shiomi and Petersson, {George A.} and Yoko Takahashi and Satoshi Omura",

note = "Publisher Copyright: {\textcopyright} 2016 Japan Antibiotics Research Association.",

year = "2016",

month = aug,

day = "1",

doi = "10.1038/ja.2015.142",

language = "English",

volume = "69",

pages = "611--615",

journal = "Journal of Antibiotics",

issn = "0021-8820",

publisher = "Japan Antibiotics Research Association",

number = "8",

}

TY - JOUR

T1 - Iminimycin A, the new iminium metabolite produced by Streptomyces griseus OS-3601

AU - Nakashima, Takuji

AU - Miyano, Rei

AU - Iwatsuki, Masato

AU - Shirahata, Tatsuya

AU - Kimura, Toru

AU - Asami, Yukihiro

AU - Kobayashi, Yoshinori

AU - Shiomi, Kazuro

AU - Petersson, George A.

AU - Takahashi, Yoko

AU - Omura, Satoshi

PY - 2016/8/1

Y1 - 2016/8/1

N2 - 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 IC50 values of 43 and 36 μM, respectively.

AB - 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 IC50 values of 43 and 36 μM, respectively.

UR - http://www.scopus.com/inward/record.url?scp=84984817806&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84984817806&partnerID=8YFLogxK

U2 - 10.1038/ja.2015.142

DO - 10.1038/ja.2015.142

M3 - Article

C2 - 26758492

AN - SCOPUS:84984817806

SN - 0021-8820

VL - 69

SP - 611

EP - 615

JO - Journal of Antibiotics

JF - Journal of Antibiotics

IS - 8

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this