Haneummycin, a new 22-membered macrolide lactam antibiotic, produced by marine-derived Streptomyces sp. KM77-8

Moeka Uemura; Keisuke Kobayashi; Noriko Sato; Kenichiro Nagai; Reiko Seki; Michiya Kamio; Takashi Fukuda; Taishi Tsubouchi; Hiroshi Tomoda; Taichi Ohshiro; Takeshi Kobayashi; Takeshi Terahara

doi:10.1038/s41429-023-00648-5

Haneummycin, a new 22-membered macrolide lactam antibiotic, produced by marine-derived Streptomyces sp. KM77-8

J Antibiot (Tokyo). 2023 Nov;76(11):650-657. doi: 10.1038/s41429-023-00648-5. Epub 2023 Sep 19.

Authors

Moeka Uemura¹, Keisuke Kobayashi^{2

3}, Noriko Sato³, Kenichiro Nagai³, Reiko Seki³, Michiya Kamio¹, Takashi Fukuda⁴, Taishi Tsubouchi^{5

6}, Hiroshi Tomoda², Taichi Ohshiro^{2

3}, Takeshi Kobayashi¹, Takeshi Terahara⁷

Affiliations

¹ Graduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo, 108-8477, Japan.
² Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
³ Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
⁴ Department of Fisheries, Faculty of Agriculture and Agricultural Technology and Innovation Research Institute, Kindai University, 3327-204 Nakamachi, Nara, 631-8505, Japan.
⁵ Department of Bacteriology, Osaka Metropolitan University, Graduate School of Medicine, 1-4-3 Asahi-machi, Abeno-ku, Osaka, 545-8585, Japan.
⁶ Research Center for Infectious Disease Sciences, Osaka Metropolitan University, Graduate School of Medicine, 1-4-3 Asahi-machi, Abeno-ku, Osaka, 545-8585, Japan.
⁷ Graduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo, 108-8477, Japan. terahara@kaiyodai.ac.jp.

PMID: 37726436
DOI: 10.1038/s41429-023-00648-5

Abstract

A new antibiotic named haneummycin (1) was isolated from a culture broth of marine-derived Streptomyces sp. KM77-8 by solvent extraction and HPLC using a C4 column. The structure of 1 was elucidated including relative stereochemistry as a new 22-membered macrolide lactam associated with a cyclopentanone and three sugars by various spectroscopic analyses, such as MS and NMR. Compound 1 displayed significant antibacterial activities against Gram-positive bacteria including vancomycin-resistant Enterococcus faecium (VRE) and methicillin-resistant Staphylococcus aureus (MRSA) with both MIC values of 8.0 µg ml^-1.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemistry
Lactams / pharmacology
Macrolides / pharmacology
Methicillin-Resistant Staphylococcus aureus*
Microbial Sensitivity Tests
Streptomyces* / chemistry

Substances

Lactams
Anti-Bacterial Agents
Macrolides