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Genome-Guided Discovery of Pretilactam from Actinosynnema pretiosum ATCC 31565

1
NHC Key Laboratory of Biotechnology of Antibiotics, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
2
CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(12), 2281; https://doi.org/10.3390/molecules24122281
Received: 9 May 2019 / Revised: 12 June 2019 / Accepted: 18 June 2019 / Published: 19 June 2019
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Abstract

Actinosynnema is a small but well-known genus of actinomycetes for production of ansamitocin, the payload component of antibody-drug conjugates against cancers. However, the secondary metabolite production profile of Actinosynnema pretiosum ATCC 31565, the most famous producer of ansamitocin, has never been fully explored. Our antiSMASH analysis of the genomic DNA of Actinosynnema pretiosum ATCC 31565 revealed a NRPS–PKS gene cluster for polyene macrolactam. The gene cluster is very similar to gene clusters for mirilactam and salinilactam, two 26-membered polyene macrolactams from Actinosynnema mirum and Salinispora tropica, respectively. Guided by this bioinformatics prediction, we characterized a novel 26-membered polyene macrolactam from Actinosynnema pretiosum ATCC 31565 and designated it pretilactam. The structure of pretilactam was elucidated by a comprehensive analysis of HRMS, 1D and 2D-NMR, with absolute configuration of chiral carbons predicted bioinformatically. Pretilactam features a dihydroxy tetrahydropyran moiety, and has a hexaene unit and a diene unit as its polyene system. A preliminary antibacterial assay indicated that pretilactam is inactive against Bacillus subtilis and Candida albicans. View Full-Text
Keywords: Actinosynnema pretiosum ATCC 31565; polyene macrolactam; pretilactam; antiSMASH Actinosynnema pretiosum ATCC 31565; polyene macrolactam; pretilactam; antiSMASH
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Wang, J.; Hu, X.; Sun, G.; Li, L.; Jiang, B.; Li, S.; Bai, L.; Liu, H.; Yu, L.; Wu, L. Genome-Guided Discovery of Pretilactam from Actinosynnema pretiosum ATCC 31565. Molecules 2019, 24, 2281.

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