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Identification of Unstable Ellagitannin Metabolites in the Leaves of <i>Quercus dentata</i> by Chemical Derivatization
oleh: Zhang-Bin Liu, Yosuke Matsuo, Yoshinori Saito, Yong-Lin Huang, Dian-Peng Li, Takashi Tanaka
Format: | Article |
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Diterbitkan: | MDPI AG 2023-01-01 |
Deskripsi
The identification of unstable metabolites of ellagitannins having ortho-quinone structures or reactive carbonyl groups is important to clarify the biosynthesis and degradation of ellagitannins. Our previous studies on the degradation of vescalagin, a major ellagitannin of oak young leaves, suggested that the initial step of the degradation is regioselective oxidation to generate a putative quinone intermediate. However, this intermediate has not been identified yet. In this study, young leaves of <i>Quercus dentata</i> were extracted with 80% acetonitrile containing 1,2-phenylenediamine to trap unstable ortho-quinone metabolites, and subsequent chromatographic separation afforded a phenazine derivative of the elusive quinone intermediate of vescalagin. In addition, phenylenediamine adducts of liquidambin and dehydroascorbic acid were obtained, which is significant because liquidambin is a possible biogenetic precursor of C-glycosidic ellagitannins and ascorbic acid participates in the production of another C-glycosidic ellagitannin in matured oak leaves.