Anti-Proliferative Acyl Phenols and Arylnonanoids from the Fruit Rind of Myristica malabarica Lam.

Phytochemical investigation of the methanol extract of the fruit rind of Myristica malabarica led to the isolation of eight known compounds that were identified as malabaricones A-D, promalabaricones B and C, 1-(2,6-dihydroxyphenyl)tetradecan-1-one, and ericanone by comparison with literature spectroscopic data. The structures of malabaricones A-D, promalabaricone B, and 1-(2,6-dihydroxyphenyl)tetradecan-1-one were confirmed by X-ray crystallography. In vitro assay of the isolated phenols indicated that they exhibited moderate anti-proliferative activity against the A2780 human ovarian cancer cell. Compounds (1, 3, 5, 6 and 7) had the most potent activities, whereas the anti-proliferative activities of compounds 2 and 4 were less potent.

Crystal structure of an aryl cyclo-hexyl nona-noid, an anti-proliferative mol-ecule isolated from the spice Myristica malabarica.

The title compound, C21H26O5, an aryl cyclo-hexyl nona-noid {systematic name: 3,5-dihy-droxy-2-[9-(4-hy-droxy-phen-yl)nona-noyl]cyclo-hexa-2,4-dien-1-one}, extracted from the spice plant Myristica malabarica comprises two ring components, a 4-hy-droxy-phenyl moiety and a 3,5-di-hydroxy-cyclo-hexa-2,4-dienone moiety linked by a nona-noyl chain. The mol-ecule has an extended essentially planar conformation stabilized by an intra-molecular hy-droxy O-H⋯Ocarbon-yl hydrogen bond, giving a dihedral angle between the two ring systems of 6.37 (15)°. The C, O and H atoms associated with one of the hy-droxy groups of the cyclo-hexa-dienone component are disordered over two sets of sites with site occupancies of 0.6972 and 0.3028. In the crystal, hy-droxy O-H⋯O hydrogen bonds to carbonyl O-atom acceptors form large centrosymmetric R22(36) cyclic dimers, which are further extended into supra-molecular one-dimensional ribbon structures along [1-11].