New derivatives of ursolic acid through the biotransformation by Bacillus megaterium CGMCC 1.1741 as inhibitors on nitric oxide production

  • Bioorg Med Chem Lett. 2017 Jun 1;27(11):2575-2578. doi: 10.1016/j.bmcl.2017.03.076.
Chao Zhang  1 ,  Shao-Hua Xu  1 ,  Bai-Ling Ma  2 ,  Wei-Wei Wang  2 ,  Bo-Yang Yu  2 ,  Jian Zhang  3
Affiliations
  • 1. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, Jiangsu 210009, China.
  • 2. Jiangsu Key Laboratory of TCM Evaluation and Translational Research, China Pharmaceutical University, Nanjing, Jiangsu 211198, China.
  • 3. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, Jiangsu 210009, China. Electronic address: [email protected].
PMID: 28427811 DOI: 10.1016/j.bmcl.2017.03.076
Abstract

Microbial transformation of ursolic acid (1) by Bacillus megaterium CGMCC 1.1741 was investigated and yielded five metabolites identified as 3-oxo-urs-12-en-28-oic acid (2); 1β,11α-dihydroxy-3-oxo-urs-12-en-28-oic acid (3); 1β-hydroxy-3-oxo-urs-12-en-28, 13-lactoe (4); 1β,3β, 11α-trihydroxyurs-12-en-28-oic acid (5) and 1β,11α-dihydroxy-3-oxo-urs-12-en-28-O-β-d-glucopyranoside (6). Metabolites 3, 4, 5 and 6 were new natural products. Their nitric oxide (NO) production inhibitory activity was assessed in lipopolysaccharide (LPS) - stimulated RAW 264.7 cells. Compounds 3 and 4 exhibited significant activities with the IC50 values of 1.243 and 1.711μM, respectively. A primary structure-activity relationship was also discussed.

Keywords
Bacillus megaterium CGMCC 1.1741; Microbial transformation; Nitric oxide production; Ursolic acid.