Cipadonoid A, a Novel Limonoid with an Unprecedented Skeleton, from Cipadessa cinerasecns

Abstract

Cipadonoid A ( 1), a novel limonoid with an unprecedented skeleton, was isolated from the leaves of Cipadessa cinerasecns. Its structure and relative configuration were determined by spectroscopic analysis and computer modeling. 1 represents a new type of limonoid, characterized by a rearranged tetrahydropyranyl ring B incorporating usually exocyclic C-30. A possible biosynthetic pathway of 1 was also proposed.

Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata

“…The absolute configuration of the compound was determined by applying the CD excitation chirality method 17. 2c The CD spectrum exhibited a positive split (231 nm, Δ ε =−0.48; 250 nm, Δ ε =6.56) due to the excitation coupling between the two chromophores of the 2‐en‐1‐one and 12‐en‐11‐one systems;17 this result indicated a clockwise orientation of the transition dipole moments of the two chromophores (see Figure S16 b). Thus, the absolute configuration of this compound, perforalactone C ( 3 ), a C 20 quassinoid with a 19‐OAc group, was determined and is identical to that of 1 and 2 .…”

16-nor Limonoids from Harrisonia perforata as promising selective 11β-HSD1 inhibitors

“…Recently, unprecedented quassinoids and limonoid derivatives with notable biological properties have been discovered and evaluated by our group141516. As part of our continuous effort to search for bioactive natural products17181920, two new 16-nor limonoids, harperspinoids A and B ( 1 and 2 ), with a unique 7/5/5/6/5 ring system, as well as a known one, Harperforin G ( 3 ), were isolated from the aerial parts of the title plant (Fig. 1).…”

Natural product sciences: an integrative approach to the innovations of plant natural products

“…Harrpenoid B has a rearranged spirocyclic moiety (Yan et al, 2011). Cipadonoid A is a novel limonoid with a rearranged tetrahydropyranyl ring B containing an unusual C-30 exomethylene from leaves of Cipadessa cinerascens (Fang et al, 2008). From the same plant, six more new limonoids, namely cipadonoids B-G belonging to rings B,D-seco-type, were isolated ( Figure 6) (Fang et al, 2009).…”