Use of 13C-NMR Chemical Shifts; Application of Principal Component Analysis for Categorizing Structurally Similar Methoxyflavones and Correlation Analysis between Chemical Shifts and Cytotoxicity
- 1 February 2021
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 69 (2), 199-202
- https://doi.org/10.1248/cpb.c20-00778
Abstract
The 13C-NMR spectral data for the 15-carbon flavonoid skeleton in eleven methoxyflavones isolated from Kaempferia parviflora (Zingiberaceae) were processed by principal component analysis (PCA). Based on the PCA score plots, the methoxyflavones were categorized into three groups according to their structural features. The cytotoxicities of the methoxyflavones toward 3T3-L1 murine preadipocyte cells were evaluated by 3-(4,5-dimethylthiazole-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTT) assay and found to differ according to structure. The relationship between the 13C-NMR chemical shifts of the methoxyflavones and their cytotoxicities was investigated using Pearson’s correlation analysis. The 13C-NMR signal at C-10, a quaternary carbon, was correlated with cytotoxicity. Based on these results, a structural design which lowers the 13C-NMR chemical shift at C-10 would be important for the development of cytotoxic compounds. Although quantitative structure–activity and structure–property relationships are well established paradigms for predicting trends among a series of compounds, quantitative property–activity relationships have been relatively unstudied. This approach offers a new strategy for directing structure–activity relationship research.Keywords
This publication has 6 references indexed in Scilit:
- 13C-NMR-Based Metabolomic Profiling of Typical Asian Soy SaucesMolecules, 2016
- Compositional differences among Chinese soy sauce types studied by 13C NMR spectroscopy coupled with multivariate statistical analysisTalanta, 2016
- Suppression of adipocyte hypertrophy by polymethoxyflavonoids isolated from Kaempferia parvifloraPhytomedicine, 2014
- Preventive effect of Kaempferia parviflora ethyl acetate extract and its major components polymethoxyflavonoid on metabolic diseasesFitoterapia, 2011
- Use of 13C NMR Chemical Shift as QSAR/QSPR DescriptorChemical Reviews, 2011
- α-Substituent effects on 13C NMR chemical shifts in some aliphatic compounds: Application of principal component analysis (PCA)Journal of Molecular Structure, 2009