Nomimicins B-D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

Zhiwei Zhang; Tao Zhou; Taehui Yang; Keisuke Fukaya; Enjuro Harunari; Shun Saito; Katsuhisa Yamada; Chiaki Imada; Daisuke Urabe; Yasuhiro Igarashi

doi:10.3762/bjoc.17.141

Nomimicins B-D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

Zhiwei Zhang, Tao Zhou, Taehui Yang, Keisuke Fukaya, Enjuro Harunari, Shun Saito, Katsuhisa Yamada, Chiaki Imada, Daisuke Urabe, Yasuhiro Igarashi

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

9 Citations (Scopus)

Abstract

Three new tetronate-class polyketides, nomimicins B, C, and D, along with nomimicin, hereafter named nomimicin A, were isolated from the culture extract of Actinomadura sp. AKA43 collected from floating particles in the deep-sea water of Sagami Bay, Japan. The structures of nomimicins B, C, and D were elucidated through the interpretation of NMR and MS analytical data, and the absolute configuration was determined by combination of NOESY/ROESY and ECD analyses. Nomimicins B, C, and D showed antimicrobial activity against Gram-positive bacteria, Kocuria rhizophila and Bacillus subtilis, with MIC values in the range of 6.5 to 12.5 μg/mL. Nomimicins B and C also displayed cytotoxicity against P388 murine leukemia cells with IC50 values of 33 and 89 μM, respectively.

Original language	English
Pages (from-to)	2194-2202
Number of pages	9
Journal	Beilstein Journal of Organic Chemistry
Volume	17
DOIs	https://doi.org/10.3762/bjoc.17.141
Publication status	Published - 2021
Externally published	Yes

Keywords

Actinomadura
Nomimicin
Polyketide
Spirotetronate

ASJC Scopus subject areas

Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3762/bjoc.17.141

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title = "Nomimicins B-D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura",

abstract = "Three new tetronate-class polyketides, nomimicins B, C, and D, along with nomimicin, hereafter named nomimicin A, were isolated from the culture extract of Actinomadura sp. AKA43 collected from floating particles in the deep-sea water of Sagami Bay, Japan. The structures of nomimicins B, C, and D were elucidated through the interpretation of NMR and MS analytical data, and the absolute configuration was determined by combination of NOESY/ROESY and ECD analyses. Nomimicins B, C, and D showed antimicrobial activity against Gram-positive bacteria, Kocuria rhizophila and Bacillus subtilis, with MIC values in the range of 6.5 to 12.5 μg/mL. Nomimicins B and C also displayed cytotoxicity against P388 murine leukemia cells with IC50 values of 33 and 89 μM, respectively.",

keywords = "Actinomadura, Nomimicin, Polyketide, Spirotetronate",

author = "Zhiwei Zhang and Tao Zhou and Taehui Yang and Keisuke Fukaya and Enjuro Harunari and Shun Saito and Katsuhisa Yamada and Chiaki Imada and Daisuke Urabe and Yasuhiro Igarashi",

note = "Publisher Copyright: {\textcopyright} 2021 Zhang et al.",

year = "2021",

doi = "10.3762/bjoc.17.141",

language = "English",

volume = "17",

pages = "2194--2202",

journal = "Beilstein Journal of Organic Chemistry",

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TY - JOUR

T1 - Nomimicins B-D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

AU - Zhang, Zhiwei

AU - Zhou, Tao

AU - Yang, Taehui

AU - Fukaya, Keisuke

AU - Harunari, Enjuro

AU - Saito, Shun

AU - Yamada, Katsuhisa

AU - Imada, Chiaki

AU - Urabe, Daisuke

AU - Igarashi, Yasuhiro

PY - 2021

Y1 - 2021

N2 - Three new tetronate-class polyketides, nomimicins B, C, and D, along with nomimicin, hereafter named nomimicin A, were isolated from the culture extract of Actinomadura sp. AKA43 collected from floating particles in the deep-sea water of Sagami Bay, Japan. The structures of nomimicins B, C, and D were elucidated through the interpretation of NMR and MS analytical data, and the absolute configuration was determined by combination of NOESY/ROESY and ECD analyses. Nomimicins B, C, and D showed antimicrobial activity against Gram-positive bacteria, Kocuria rhizophila and Bacillus subtilis, with MIC values in the range of 6.5 to 12.5 μg/mL. Nomimicins B and C also displayed cytotoxicity against P388 murine leukemia cells with IC50 values of 33 and 89 μM, respectively.

AB - Three new tetronate-class polyketides, nomimicins B, C, and D, along with nomimicin, hereafter named nomimicin A, were isolated from the culture extract of Actinomadura sp. AKA43 collected from floating particles in the deep-sea water of Sagami Bay, Japan. The structures of nomimicins B, C, and D were elucidated through the interpretation of NMR and MS analytical data, and the absolute configuration was determined by combination of NOESY/ROESY and ECD analyses. Nomimicins B, C, and D showed antimicrobial activity against Gram-positive bacteria, Kocuria rhizophila and Bacillus subtilis, with MIC values in the range of 6.5 to 12.5 μg/mL. Nomimicins B and C also displayed cytotoxicity against P388 murine leukemia cells with IC50 values of 33 and 89 μM, respectively.

KW - Actinomadura

KW - Nomimicin

KW - Polyketide

KW - Spirotetronate

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U2 - 10.3762/bjoc.17.141

DO - 10.3762/bjoc.17.141

M3 - Article

AN - SCOPUS:85113837523

SN - 1860-5397

VL - 17

SP - 2194

EP - 2202

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Nomimicins B-D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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