Structurally diverse glycosides of secoiridoid, bisiridoid, and triterpene-bisiridoid conjugates from the flower buds of two Caprifoliaceae plants and their ATP-citrate lyase inhibitory activities.

The ethanolic extracts of the dried flower buds of two Caprifoliaceae plants, Lonicera japonica and Abelia × grandiflora, showed considerable inhibitory activities against adenosine triphosphate (ATP)-citrate lyase (ACL), a new promising drug target for the treatment of metabolic disorders. Bioassay-guided purification in conjunction with HPLC-PDA profiling led to the isolation and characterization of thirty-five (1-35) and fourteen (1'-14') structurally diverse compounds from the above two plant extracts, respectively. Compounds 1-9 and 1'-6' are previously undescribed glycosides. Their structures were elucidated on the basis of spectroscopic data, electronic circular dichroism (ECD), and single crystal X-ray diffraction analyses. In particular, lonicejaposide A (1) has an unprecedented skeleton generated through the coupling of C-7 in secologanin with C-2'' in phenylacetaldehyde via an aldol condensation. Abeliflorosides A (1') and B (2') are hitherto unknown glycosides of triterpene and bisiridoid conjugates constructed through the formation of a 1,3-dioxane moiety. All the isolates were evaluated for their inhibitory activities against ACL. Compounds 9, 25-28, 31, 1', 2', and 14' displayed significant inhibitory effects, with IC

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