Isolation and Identification of Pentalenolactone Analogs from Streptomyces sp. NRRL S-4

Molecules

Wenhui Wu¹  Huanhuan Li²  Hongji Li²  Peng Sun²  Shuo Chen² 

[1] Department of Marine Bio-Pharmacology, College of Food Science and Technology, Shanghai Ocean University, 999 Huchenghuan Road, Shanghai 201306, China;Department of Phytochemistry, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, China;

关键词: Streptomyces;    pentalenolactone;    terpenoid;    genome mining;    secondary metabolites;   

DOI  :  10.3390/molecules26237377

来源: DOAJ

【 摘 要 】

Terpene synthases are widely distributed in Actinobacteria. Genome sequencing of Streptomyces sp. NRRL S-4 uncovered a biosynthetic gene cluster (BGC) that putatively synthesizes pentalenolactone type terpenes. Guided by genomic information, the S-4 strain was chemically investigated, resulting in the isolation of two new sesquiterpenoids, 1-deoxy-8α-hydroxypentalenic acid (1) and 1-deoxy-9β-hydroxy-11-oxopentalenic acid (2), as shunt metabolites of the pentalenolactone (3) biosynthesis pathway. Their structures and absolute configurations were elucidated by analyses of HRESIMS and NMR spectroscopic data as well as time-dependent density functional theory/electronic circular dichroism (TDDFT/ECD) calculations. Compounds 1 and 2 exhibited moderate antimicrobial activities against Gram-positive and Gram-negative bacteria. These results confirmed that the pentalenolactone pathway was functional in this organism and will facilitate efforts for exploring Actinobacteria using further genome mining strategies.

【 授权许可】

Unknown