One-Step Semisynthesis of a Segetane Diterpenoid from a Jatrophane Precursor via a Diels-Alder Reaction
Luo-Sheng Wan1, Li-Dong Shao1, Liangbing Fu2
1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.
Abstract:
A novel segetane diterpenoid (1) and four jatrophane diterpenoids (2-5) were isolated from an acetone extract of Euphorbia peplus. Due to quantity limitations, we prepared 1 via a Diels-Alder reaction, an approach motivated by this compound's biosynthetic pathway and successfully performed X-ray analysis of 1. Furthermore, in an in vitro activity test, 1 exhibited moderate anti-inflammatory activity, whereas both its precursor (2) and the relevant intermediate (2a, IC50 = 1.56 μM) exhibited significant anti-inflammatory activity.
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