RESUMO
A new andirobin, thaimoluccensin A (1), and two new phragmalin-type limonoids, thaimoluccensins B (2) and C (3), were isolated from seeds of a Thai mangrove plant, Xylocarpus moluccensis, together with eight known compounds. The structures of these compounds were elucidated on the basis of spectroscopic data. Only 7-deacetylgedunin (7), a gedunin-type limonoid, exhibited significant inhibitory activity against nitric oxide production from activated macrophages with IC(50) value less than 10 µM, suggesting that the compound has anti-inflammatory activity.
Assuntos
Anti-Inflamatórios/química , Cumarínicos/química , Limoninas/química , Meliaceae/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Humanos , Limoninas/isolamento & purificação , Limoninas/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Espectroscopia de Ressonância Magnética , Conformação Molecular , Óxido Nítrico/metabolismo , Sementes/química , TailândiaRESUMO
THE TITLE COMPOUND [SYSTEMATIC NAME: (1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(furan-3-yl)-5-hy-droxy-4b,7,7,10a,12a-penta-methyl-4b,5,6,6a,7,10a,10b,11,12,12a-deca-hydro-naphtho-[2,1-f]oxireno[2,3-d]isochromene-3,8(1H,3aH)-dione], C(26)H(32)O(6), which is a limonoid-type triterpene isolated from the seeds of X. moluccensis, crystallizes with three independent mol-ecules with very similar geometries in the asymmetric unit. In each mol-ecule, the four fused six-membered rings of the genudin core adopt distorted half-chair, chair, twist-boat and twisted half-chair conformations. In the crystal, inter-molecular O-Hâ¯O hydrogen bonds link the mol-ecules into helical chains propagated in [100]. Weak non-classical C-Hâ¯O contacts further consolidate the crystal packing.
