In Vitro Evaluation of Potential Bitterness-Masking Terpenoids from the Canada Goldenrod (Solidago canadensis)
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- 作者：Jie Li ; Li Pan ; Joshua N. Fletcher ; Wei Lv ; Ye Deng ; Michael A. Vincent ; Jay P. Slack ; T. Scott McCluskey ; Zhonghua Jia ; Mark Cushman ; A. Douglas Kinghorn
- 刊名：Journal of Natural Products
- 出版年：2014
- 出版时间：July 25, 2014
- 年：2014
- 卷：77
- 期：7
- 页码：1739-1743
- 全文大小：272K
- ISSN：1520-6025
文摘
In a screening of extracts of selected plants native to Ohio against the human bitterness receptor hTAS2R31, a chloroform-soluble extract of the aerial parts of Solidago canadensis (Canada goldenrod) was determined to have hTAS2R31 antagonistic activity and, thus, was fractionated for isolation of potential bitterness-masking agents. One new labdane diterpenoid, solidagol (1), and six known terpenoids, including two labdane diterpenoids (2 and 3), three clerodane diterpenoids (6尾-angeloyloxykolavenic acid, 6尾-tigloyloxykolavenic acid, and crotonic acid), and a triterpenoid (longispinogenin), were isolated. Among these compounds, 3尾-acetoxycopalic acid (2) was found to be the first member of the labdane diterpene class shown to have inhibitory activity against hTAS2R31 activation (IC50 8 渭M). A homology model of hTAS2R31 was constructed, and the molecular docking of 2 to this model indicated that this diterpenoid binds well to the active site of hTAS2R31, whereas this was not the case for the closely structurally related compound 3 (sempervirenic acid). The content of 2 in the chloroform-soluble portion of the methanolic extract of S. canadensis was up to 2.24 g/100 g dry weight, as determined by HPLC.