From a methanolic extract of the aril of Myristica fragrans HOUTT. (mace), the following new threo and erythro acyclic bis-phenylpropanoids were isolated: threo -2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propan-1-ol (la), erythro-2-(4-allyl-2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropane (2b), erythro-2-(4-allyl-2,6-dimethoxyphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-ol (3b), 2-(4-allyl-2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propane (4), erythro-2-(4-allyl-2-methoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propan-1-ol (5b), threo-1-(4-hydroxy-3, 5-dimethoxyphenyl)-2-[2-methoxy-4-(1(E)-propenyl)phenoxy]propan-1-ol (6a) and erythro-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(3-hydroxy-4,5-dimethoxyphenyl)propan-1-ol (7b). Contrary to a previous finding that Myristica species contain only an erythro type of acyclic bis-phenylpropanoids, we isolated both threo and erythro derivatives. Keywords •\ acyclic bis-phenylpropanoid; mace; Myristicaceae; Myristica fragrans; neolignanThe aril of Myristica fragrans HOUTT. (Myristicaceae), mace, has been widely used as a spice and a valuable remedy in Ayurvedic medicine for treatment in the low stage of fever, in consumptive complaints, humoral asthma, and when mixed with aromatics, in wasting and long-term bowel complaints.2) There have been numerous reports on the constituents of mace as well as nutmeg (the seed kernels of Myristica fragrans) in the literature. These include essential oils,3) fats, glycerides,4) cyclic and acyclic bis-phenylpropanoids5) and a pigment.6) Pharmacological studies have also been conducted by many workers as to hallucinogenic effect,7) and inhibitory effects on the growth of silkworm larvae, Bombyx mori,5a,b) and on prostaglandin biosynthesis.8) Recently, we have reported that dehydrodiisoeugenol and 5 '-methoxydehydrodiisoeugenol from mace have antibacterial action against a primary cariogenic bacterium, Streptococcus mutans.9) In a continuation of this investigation, we report the isolation of new threo and erythro diastereomers of acyclic bis -phenylpropanoids (1a, 2b, 3b, 5b, 6a and 7b; but with a = threo and b = erythro), as well as 4.
Results and DiscussionA methanolic extract of the aril of Myristica fragrans was subjected to solvent fractionation and silica gel column chromatography. This procedure led to the isolation of new compounds (1a, 2b, 3b, 4, 5b, 6a and 7b) along with the known 4-propenylphenols, dehydrodiisoeugenol derivatives, guaiacin,9) and acyclic bis-phenylpropanoids.9) The structures of the new compounds were determined as follows:Compound la was isolated as an oily substance with the molecular formula C21 H26O6. The proton nuclear magnetic resonance (1 H-NMR) spectrum (in CD3COOD) showed signals
