Three new guaiane sesquiterpene lactones from rhizomes of Curcuma wenyujin

Abstract

Three new guaiane sesquiterpene lactones (4S)-4-hydroxy-gweicurculactone (1), zedoalactone G (2), and (1R, 4R, 5S, 10S)-zedoalactone B (3), and three known guaiane sesquiterpene lactones, including zedoarolide B (4), zedoalactone B (5), and a new natural product (+)-zedoalactone A (6), were isolated from the rhizomes of Curcuma wenyujin Y.H. Chen et C. Ling. The structures were elucidated by spectroscopic methods including 1D and 2D NMR and HR-ESI-MS. The absolute configuration of 2 was determined via the calculated electronic circular dichroism (ECD), whereas the absolute configurations of 1 and 3 were determined via the ECD data of the [Rh₂(OCOCF₃)₄] complex and [Mo₂(OAc)₄] complex, respectively. The inhibitory effects of compounds 1–6 on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. All of them exhibited weak anti-inflammatory activity.

Keywords:

• Curcuma wenyujin
• guaiane-type sesquiterpenes
• (4S)-4-hydroxy-gweicurculactone
• zedoalactone G
• (1R, 4R, 5S, 10S)-zedoalactone B
• (+)-zedoalactone A

Acknowledgements

The authors acknowledge the National Natural Science Foundation of China (No. 30901961), the Fundamental Research Funds for the Central public welfare research institutes (No. ZZ20092015 and No. ZZ070833) and National Science and Technology Special Project for New Drugs Innovation (No. 2009ZX09301-005 and 2009ZX09308-003) for their financial support to this work. The support of the Supercomputing Center, CNIC, CAS for computer time is acknowledged, too.