Norcyperone, a Novel Skeleton Norsesquiterpene from Cyperus rotundus L.

• Main Authors: Zhong-Mei Zou, Ying Chang, Yang Lu, Chang-Yuan Yu, Hong-Wu Zhang, Yan Xu
• Format: Article
• Language: English
• Published: MDPI AG 2008-10-01
• Series: Molecules
• Subjects: Cyperus rotundus L.; norsesquiterpene; norcyperone; bicyclo[5.3.1]undecane-3-one
• Online Access: http://www.mdpi.com/1420-3049/13/10/2474/

A novel norsesquiterpene, named norcyperone (1), and three known compounds: (-)-clovane-2,9-diol (2), rosenonolactone (3), and 5a,8a-epidioxy-(20S,22E,24R)-ergosta-6,22-dien-3β-ol (4) were isolated from the rhizomes of Cyperus rotundus L. The structure of 1 was elucidated as 8,11,11-trimethylbicyclo[5.3.1]undecane-5a, 8a-epoxy-3-one on the basis of extensive spectroscopic analyses, including 1D- and 2D-NMR, MS experiments, and single-crystal X-ray diffraction. This is the first report of a 8,11,11-trimethyl- bicyclo[5.3.1]undecane-3-one type norsesquiterpene with a tetrahydrofuran ring at C-5 and C-8.