Muñoz Acuña Ulyana, Carcache Peter J Blanco, Matthew Susan, Carcache de Blanco Esperanza J
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.
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.
Food Chem. 2016 Jul 1;202:269-75. doi: 10.1016/j.foodchem.2016.01.060. Epub 2016 Jan 15.
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).
对肉豆蔻（肉豆蔻香料）假种皮进行生物测定导向的分级分离，得到了五种酚类化合物，一种新的无环双苯基丙烷类化合物（1）和四种先前已知的酚类化合物：化合物（1）（S）1-（3,4,5-三甲氧基苯基）-2-（3-甲氧基-5-（丙-1-基）苯基）-丙-1-醇，（2）苯甲醇；α-[1-[2,6-二甲氧基-4-（2-丙烯-1-基）苯氧基]乙基]-3,4-二甲氧基-1-乙酸酯，（3）去甲异土木香内酯A，苯酚，4-[(2S,3S)-2,3-二氢-7-甲氧基-3-甲基-5-（1E）-1-丙烯基-2-苯并呋喃基]-2,6-二甲氧基，（4）1,3-苯并二恶唑-5-甲醇，α-[1-[2,6-二甲氧基-4-（2-丙烯基）苯氧基]乙基]-乙酸酯，（5）里卡林C；苯并呋喃，2,3-二氢-7-甲氧基-3-甲基-5-（1E）-1-丙烯基-2-（3,4,5-三甲氧基苯基）。采用核磁共振管莫舍尔酯反应来表征和确定新分离的手性醇（1）的绝对构型归属。对化合物（1）（IC50 = 3.04μM）、化合物（2）（IC50 = 0.001μM）、化合物（4）（IC50 = 22.07μM）和化合物（5）（IC50 = 3.11μM）进行了PARP-1抑制活性评估。此外，对分离得到的次生代谢产物进行了NF-κB和K-Ras抑制活性测试。在p65测定中进行测试时，化合物（2）和（4）表现出强效的NF-κB抑制作用（IC50分别为1.5 nM和3.4 nM）。
