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Food Chem. 2016 Jul 1;202:269-75. doi: 10.1016/j.foodchem.2016.01.060. Epub 2016 Jan 15.

New acyclic bis phenylpropanoid and neolignans, from Myristica fragrans Houtt., exhibiting PARP-1 and NF-κB inhibitory effects.

Author information

1
Division of Pharmacy Practice and Science, College of Pharmacy, The Ohio State University, 141N Parks Hall, 500 W. 12th Avenue, Columbus, OH 43210, United States; Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 141N Parks Hall, 500 W. 12th Avenue, Columbus, OH 43210, United States.
2
Division of Pharmacy Practice and Science, College of Pharmacy, The Ohio State University, 141N Parks Hall, 500 W. 12th Avenue, Columbus, OH 43210, United States.
3
Division of Pharmacy Practice and Science, College of Pharmacy, The Ohio State University, 141N Parks Hall, 500 W. 12th Avenue, Columbus, OH 43210, United States; Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 141N Parks Hall, 500 W. 12th Avenue, Columbus, OH 43210, United States. Electronic address: carcache-de-blan.1@osu.edu.

Abstract

The bioassay-guided fractionation of the aril of Myristica fragrans (mace spice) yielded five phenolic compounds, one new acyclic bis phenylpropanoid (1) and four previously known phenolic compounds: compounds (1) (S) 1-(3,4,5-trimethoxyphenyl)-2-(3-methoxy-5-(prop-1-yl) phenyl)-propan-1-ol, (2) benzenemethanol; α-[1-[2,6-dimethoxy-4-(2-propen-1-yl)phenoxy]ethyl]-3,4-dimethoxy-1-acetate, (3) odoratisol A, phenol, 4-[(2S,3S)-2,3-dihydro-7-methoxy-3-methyl-5-(1E)-1-propenyl-2-benzofuranyl]-2,6-dimethoxy, (4) 1,3-benzodioxate-5-methanol,α-[1-[2,6-dimethoxy-4-(2-propenyl)phenoxy]ethyl]-acetate, (5) licarin C; benzofuran,2,3-dihydro-7-methoxy-3-methyl-5-(1E)-1-yl-2-(3,4,5-trimethoxyphenyl). An NMR tube Mosher ester reaction was used in an approach to characterize and determine the assignment of the absolute configuration of the new isolated chiral alcohol (1). The PARP-1 inhibitory activity was evaluated for compound (1) (IC50=3.04μM), compound (2) (IC50=0.001μM), compound (4) (IC50=22.07μM) and compound (5) (IC50=3.11μM). Furthermore, the isolated secondary metabolites were tested for NF-κB and K-Ras inhibitory activities. When tested in the p65 assay, compounds (2) and (4) displayed potent NF-κB inhibition (IC50=1.5 nM and 3.4nM, respectively).

KEYWORDS:

Acyclic bisphenyl propanoids; K-Ras; Mace; Myristica fragrans; NF-κB; Neolignans; PARP-1

PMID:
26920294
PMCID:
PMC4770456
DOI:
10.1016/j.foodchem.2016.01.060
[Indexed for MEDLINE]
Free PMC Article

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