Structure of Sesquiterpenoids from Celastrus angulatus

Abstract

Three new ß-dihydroagarofuran sesquiterpene polyol esters were isolated from the seed oil of Celastrus angulatus. Their structures have been elucidated, on the basis of uv, ir, mass, and ID and 2D nmr spectroscopy, as 6aacetoxy-1 ß,8ß, 98-tribenzoyloxy-ß-dihydroagarofuran [1], 1ß,8ß, 13-ttiacetoxy-9ß-benzoyloxy-ß-dihydroagarofuran [2], and 1ß,8 , 13triacetoxy-98-benzoyloxy^-dihydroagarofuran [31. Celastrus angulatus Max. (Celastraceae) is widely distributed in China, where its root bark and leaves are used traditionally as natural insecticides ( 1). An insecticidal ß-dihydroagarofuran polyol ester of the root bark has been isolated (2) which is similar in structure to those isolated from other species of Celastraceae plants (3,4).

Two New β-Dihydroagarofuran Sesquiterpenes from Celastrus orbiculatus Thunb and Their Anti-Proliferative Activity

“…The relative configuration of Compound 1 was established by the coupling constants of the key proton signals and the NOESY spectrum. Generally, naturally occurring β-dihydroagarofuran sesquiterpenes exhibit β-orientations for H 2 -13 and H-7 [ 15 , 16 ]. The NOESY correlations of H 2 -13 and H 3 -12, H 2 -13 and H-9, H-6 and H 3 -12, and H 3 -15 and H-7 suggested that H 3 -12, H-9, H-6, and H-15 were in the β-orientation, while the α-orientation of H 3 -14 and H-1 were determined on the basis of NOESY correlations between H-4 and H 3 -14 and between H-1 and H-4 [ 17 ].…”