New polycyclic tetramate macrolactams with antimycobacterial activity produced by marine-derived Streptomyces sp. KKMA-0239

Satoru Shigeno; Miyu Kadowaki; Kenichiro Nagai; Kanji Hosoda; Takeshi Terahara; Tomoyasu Nishimura; Naoki Hasegawa; Hiroshi Tomoda; Taichi Ohshiro

doi:10.1038/s41429-024-00710-w

New polycyclic tetramate macrolactams with antimycobacterial activity produced by marine-derived Streptomyces sp. KKMA-0239

Satoru Shigeno
, Miyu Kadowaki
, Kenichiro Nagai
, Kanji Hosoda
, Takeshi Terahara
, Tomoyasu Nishimura
, Naoki Hasegawa
, Hiroshi Tomoda
, Taichi Ohshiro

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

9 Citations (Scopus)

Abstract

During our screening for anti-mycobacterial agents against Mycobacterium avium complex (MAC), two new polycyclic tetramate macrolactams (PTMs), named hydroxycapsimycin (1) and brokamycin (2), were isolated along with the known PTM, ikarugamycin (3), from the culture broth of marine-derived Streptomyces sp. KKMA-0239. The relative structures of 1 and 2 were elucidated by spectroscopic data analyses, including 1D and 2D NMR. Furthermore, the absolute configuration of 1 was confirmed by a single-crystal X-ray diffraction analysis. Compounds 2 and 3 exhibited moderate antimycobacterial activities against MAC, including clinically isolated drug-resistant M. avium.

Original language	English
Pages (from-to)	265-271
Number of pages	7
Journal	Journal of Antibiotics
Volume	77
Issue number	5
DOIs	https://doi.org/10.1038/s41429-024-00710-w
Publication status	Published - 2024 May

UN SDGs

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

SDG 14 Life Below Water

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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10.1038/s41429-024-00710-w

Cite this

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title = "New polycyclic tetramate macrolactams with antimycobacterial activity produced by marine-derived Streptomyces sp. KKMA-0239",

abstract = "During our screening for anti-mycobacterial agents against Mycobacterium avium complex (MAC), two new polycyclic tetramate macrolactams (PTMs), named hydroxycapsimycin (1) and brokamycin (2), were isolated along with the known PTM, ikarugamycin (3), from the culture broth of marine-derived Streptomyces sp. KKMA-0239. The relative structures of 1 and 2 were elucidated by spectroscopic data analyses, including 1D and 2D NMR. Furthermore, the absolute configuration of 1 was confirmed by a single-crystal X-ray diffraction analysis. Compounds 2 and 3 exhibited moderate antimycobacterial activities against MAC, including clinically isolated drug-resistant M. avium.",

author = "Satoru Shigeno and Miyu Kadowaki and Kenichiro Nagai and Kanji Hosoda and Takeshi Terahara and Tomoyasu Nishimura and Naoki Hasegawa and Hiroshi Tomoda and Taichi Ohshiro",

note = "Publisher Copyright: {\textcopyright} The Author(s), under exclusive licence to the Japan Antibiotics Research Association 2024.",

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doi = "10.1038/s41429-024-00710-w",

language = "English",

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pages = "265--271",

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T1 - New polycyclic tetramate macrolactams with antimycobacterial activity produced by marine-derived Streptomyces sp. KKMA-0239

AU - Shigeno, Satoru

AU - Kadowaki, Miyu

AU - Nagai, Kenichiro

AU - Hosoda, Kanji

AU - Terahara, Takeshi

AU - Nishimura, Tomoyasu

AU - Hasegawa, Naoki

AU - Tomoda, Hiroshi

AU - Ohshiro, Taichi

PY - 2024/5

Y1 - 2024/5

N2 - During our screening for anti-mycobacterial agents against Mycobacterium avium complex (MAC), two new polycyclic tetramate macrolactams (PTMs), named hydroxycapsimycin (1) and brokamycin (2), were isolated along with the known PTM, ikarugamycin (3), from the culture broth of marine-derived Streptomyces sp. KKMA-0239. The relative structures of 1 and 2 were elucidated by spectroscopic data analyses, including 1D and 2D NMR. Furthermore, the absolute configuration of 1 was confirmed by a single-crystal X-ray diffraction analysis. Compounds 2 and 3 exhibited moderate antimycobacterial activities against MAC, including clinically isolated drug-resistant M. avium.

AB - During our screening for anti-mycobacterial agents against Mycobacterium avium complex (MAC), two new polycyclic tetramate macrolactams (PTMs), named hydroxycapsimycin (1) and brokamycin (2), were isolated along with the known PTM, ikarugamycin (3), from the culture broth of marine-derived Streptomyces sp. KKMA-0239. The relative structures of 1 and 2 were elucidated by spectroscopic data analyses, including 1D and 2D NMR. Furthermore, the absolute configuration of 1 was confirmed by a single-crystal X-ray diffraction analysis. Compounds 2 and 3 exhibited moderate antimycobacterial activities against MAC, including clinically isolated drug-resistant M. avium.

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U2 - 10.1038/s41429-024-00710-w

DO - 10.1038/s41429-024-00710-w

M3 - Article

C2 - 38531967

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SN - 0021-8820

VL - 77

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IS - 5

ER -

New polycyclic tetramate macrolactams with antimycobacterial activity produced by marine-derived Streptomyces sp. KKMA-0239

Abstract

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