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Significance and Transformation of 3-Alkyl-2-Methoxypyrazines Through Grapes to Wine: Olfactory Properties, Metabolism, Biochemical Regulation, and the HP–MP Cycle

by Xianfang Zhao 1,2,†, Yanlun Ju 1,†, Xiaofeng Wei 1, Shuo Dong 1, Xiangyu Sun 1,* and Yulin Fang 1,*
1
College of Enology, Heyang Viti-Viniculture Station, Northwest A&F University, Yangling 712100, China
2
Life School of Science and Technology, Henan Institute of Science and Technology, Xinxiang 453003, China
*
Authors to whom correspondence should be addressed.
Both authors contributed equally.
Molecules 2019, 24(24), 4598; https://doi.org/10.3390/molecules24244598
Received: 25 November 2019 / Revised: 12 December 2019 / Accepted: 13 December 2019 / Published: 16 December 2019
3-Alkyl-2-methoxypyrazines (MPs) contribute to the herbaceous flavor characteristics of wine and are generally considered associated with poor-quality wine. To control the MPs in grapes and wine, an accurate understanding of MP metabolism is needed. This review covers factors affecting people in the perception of MPs. Also, the history of O-methyltransferases is revisited, and the present review discusses the MP biosynthesis, degradation, and biochemical regulation. We propose the existence of a cycle between MPs and 3-alkyl-2-hydropyrazines (HPs), which proceeds via O-(de)methylation steps. This cycle governs the MP contents of wines, which make the cycle the key participant in MP regulation by genes, environmental stimuli, and microbes. In conclusion, a comprehensive metabolic pathway on which the HP–MP cycle is centered is proposed after gaining insight into their metabolism and regulation. Some directions for future studies on MPs are also proposed in this paper. View Full-Text
Keywords: 3-alkyl-2-methoxypyrazines; Vitis vinifera; wine; O-methyltransferase; O-demethylation 3-alkyl-2-methoxypyrazines; Vitis vinifera; wine; O-methyltransferase; O-demethylation
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Zhao, X.; Ju, Y.; Wei, X.; Dong, S.; Sun, X.; Fang, Y. Significance and Transformation of 3-Alkyl-2-Methoxypyrazines Through Grapes to Wine: Olfactory Properties, Metabolism, Biochemical Regulation, and the HP–MP Cycle. Molecules 2019, 24, 4598.

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