New acyclic bis phenylpropanoid and neolignans, from Myristica fragrans Houtt., exhibiting PARP-1 and NF-κB inhibitory effects.
2016 (English)In: Food Chemistry, ISSN 0308-8146, E-ISSN 1873-7072, Vol. 202, p. 269-275Article in journal (Refereed) Published
Sustainable development
SDG 3: Ensure healthy lives and promote well-being for all at all ages
Abstract [en]
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).
Place, publisher, year, edition, pages
Elsevier, 2016. Vol. 202, p. 269-275
Keywords [en]
Acyclic bisphenyl propanoids, K-Ras, Mace, Myristica fragrans, NF-κB, Neolignans, PARP-1
National Category
Medicinal Chemistry Organic Chemistry Cancer and Oncology Food Science
Research subject
Natural Science, Biomedical Sciences; Chemistry, Biochemistry; Chemistry, Medical Chemistry; Chemistry, Organic Chemistry; Humanities, English literature
Identifiers
URN: urn:nbn:se:lnu:diva-101814DOI: 10.1016/j.foodchem.2016.01.060ISI: 000370810000036PubMedID: 26920294Scopus ID: 2-s2.0-84957097450OAI: oai:DiVA.org:lnu-101814DiVA, id: diva2:1541012
Funder
NIH (National Institute of Health), P01 CA125066-S22021-03-302021-03-302022-10-31Bibliographically approved