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Triconoids A-D, Four Limonoids Possess Two Rearranged Carbon Skeletons from Trichilia connaroides
Guo-Cai Wang1, Yao-Yue Fan1, Sajan L Shyaula2
1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
Abstract:
Four limonoids, triconoids A-C (1-3) possessing a new rearranged mexicanolide skeleton and triconoid D (4) furnishing a new rearranged 1,2-seco-phragmalin skeleton, were isolated from the Nepalese plant Trichilia connaroides. Two rearranged limonoid skeletons sharing an F ring of methyl 5-oxotetrahydrofuran-2-carboxylate were postulated to be formed biosynthetically via a very unique chemical cascade. Their structures were fully accomplished by spectroscopic data, single-crystal X-ray diffraction, and electrostatic circular dichroism analysis.