Volvalerenone A, a new type of mononorsesquiterpenoid with an unprecedented 3,12-oxo bridge from Valeriana officinalis

• Published in: Tetrahedron letters Vol. 51; no. 41; pp. 5451 - 5453
• Main Authors: Wang, Peng-Cheng, Ran, Xin-Hui, Chen, Rui, Li, Liang-Chun, Xiong, Shan-Shan, Liu, Yu-Qing, Luo, Huai-Rong, Zhou, Jun, Zhao, You-Xing
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 13.10.2010; Elsevier
• Subjects: AChE inhibitory activity; Bridges (structures); Chemistry; Chemistry, Organic; Esterases; Growth factors; Mononorsesquiterpenoid; Pathways; Physical Sciences; Roots; Science & Technology; Spectroscopy; Tetrahedrons; Valeriana officinalis; Valerianacae; Volvalerenone A; X-rays; Valeriana officinalis; Valerianacae; AChE inhibitory activity; Mononorsesquiterpenoid; Volvalerenone A; VALERENIC ACID; IRIDOIDS; ROOTS; INHIBITOR; SESQUITERPENOIDS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2010.08.023

Volvalerenone A ( 1), a new type of mononorsesquiterpenoid with an unprecedented 5/6/6 tricyclic ring system, was isolated from the roots of Valeriana officinalis. Volvalerenone A ( 1), a new type of mononorsesquiterpenoid with an unprecedented 5/6/6 tricyclic ring system, was isolated from the roots of Valeriana officinalis, the official species of valerian used in Europe. The structure of volvalerenone A was elucidated based on its spectroscopic and single-crystal X-ray crystallography data. The absolute configuration was assigned by the computational method. A possible biosynthetic pathway of volvalerenone A was also proposed. Preliminary biological studies showed that volvalerenone A had weak inhibitory activity on acetylcholine esterase (AChE), and no enhancing activity on nerve growth factor (NGF)-mediated neurite outgrowth in PC12 cells was observed at 50 μM.