New acyclic bis-phenylpropanoids from the aril of Myristica fragrans.

Abstract

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

Crystal structures of three 1-arylpropane-1,2-diol 2-aryl ether derivatives and the acetate of 2,6-dimethoxy-4-(1-(E)-propenyl)phenol

“…In addition to those referred to in our previous paper (Wallis et al, 1991) further guaiacyl and syringyl ~-ether neolignans have been isolated. Thus several erythro-guaiacyl ~-ethers were found; 3a from Krameria cystisoides (Achenbach et al, 1987), 3b from Nardostachys jatamansi (Bagchi et al, 1991), and 3c and 3d from Myristica fragrans (Hattori et al, 1987). The threo-guaiacyl ~-ether 2c was isolated from Myristica fragrans (Hada et al, 1988 syringyl ~-ethers were obtained from Myristica fragrans, compounds 4a and 5b by Hattori et al (1987) and 5c and 5d by the same group .…”

“…Thus several erythro-guaiacyl ~-ethers were found; 3a from Krameria cystisoides (Achenbach et al, 1987), 3b from Nardostachys jatamansi (Bagchi et al, 1991), and 3c and 3d from Myristica fragrans (Hattori et al, 1987). The threo-guaiacyl ~-ether 2c was isolated from Myristica fragrans (Hada et al, 1988 syringyl ~-ethers were obtained from Myristica fragrans, compounds 4a and 5b by Hattori et al (1987) and 5c and 5d by the same group . Green et al (1991) recently reported the unusual erythro monomethoxy/~-ether 6 as a constituent of Piper capense.…”

Gymnasterkoreayne G, a New Inhibitory Polyacetylene against NFAT Transcription Factor from Gymnaster koraiensis

“…Moreover, empirically, the coupling constant of protons in the erythro-configuration is smaller than that in the threo-configuration. 10,11) Before gymnasterkoreayne E having large coupling constant (Jϭ4.1 Hz) was reported 3) as erythro-configuration by only comparison of coupling constant by literature, 12) but it might be assigned incorrectly due to the lack of both isomers. This time both isomers were isolated from the same plant and determined to configuration having large coupling constant as threo-and small coupling constant as erythro-.…”

Tyrosinase Inhibitory Activities of Safrole fromMyristica fragransHoutt.

“…M. fragrans is also prescribed for medicinal purposes in Asia to treat many diseases such as rheumatism, muscle spasm, decreased appetite, and diarrhea (Nguyen et al, 2010). It contains 25-30% fixed oils, 5-15% volatile oils, phenylpropanoids, lignans, and neolignans (Davis and Graham, 1982;Hattori et al, 1987;Hada et al, 1988) and has antitumor, antimicrobial, antiviral, antifungal, anti-atherosclerotic and anti-inflammatory properties (Orabi et al, 1991;Yang et al, 2006;Cho et al, 2007). Previously, novel dibenzylbutane lignan, 7-methyl ether dibenzylbutane lignan, and six known lignans, were characterized as LDL antioxidant agents from the seed of M. fragrans (Kwon et al, 2008).…”