二氢查尔酮葡萄糖苷的氧化寡聚产生的黄色色素及其反应机制。

Yellow pigments produced by oxidative oligomerization of dihydrochalcone glucoside and the reaction mechanism.

机构信息

Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan; Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guilin 541006, China.

Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.

出版信息

Food Chem. 2023 Nov 15;426:136671. doi: 10.1016/j.foodchem.2023.136671. Epub 2023 Jun 19.

DOI:10.1016/j.foodchem.2023.136671

PMID:37356249

Abstract

From the dried leaves of Lithocarpus polystachyus, yellow pigments, lithocarputins B (11) and C (12), were isolated with a colorless dihydrochalcone dimer, lithocarputin A (10). The pigments 11 and 12 are dimeric dihydrochalcone glycosides with bicyclo[3.2.1]octane structures. Each pigment is a diastereomeric mixture with enantiomeric aglycones that could not be separated. The production mechanisms of the pigments were proposed based on the in vitro enzymatic preparation from trilobatin (1), the major dihydrochalcone glucoside of L. polystachyus. The majority of the pigments in the dried leaves were the oligomers of the dihydrochalcone glycosides generated by a mechanism similar to dimerization. The pigments are probably artifacts produced in the drying process. This is the first report disclosing a detailed chemical mechanism for pigment formation from dihydrochalcone.

摘要

从石栎的干树叶中，分离出了黄色素石栎因 B（11）和 C（12），以及无色二氢查尔酮二聚体石栎因 A（10）。色素 11 和 12 是具有双环[3.2.1]辛烷结构的二聚二氢查尔酮糖苷。每种色素都是具有非对映异构体差向异构体的混合物，无法分离。根据从石栎的主要二氢查尔酮葡萄糖苷三叶苷（1）体外酶制备的结果，提出了色素的产生机制。干树叶中的大部分色素是二氢查尔酮糖苷的低聚物，其生成机制类似于二聚作用。这些色素可能是干燥过程中产生的人工产物。这是首次报道揭示了二氢查尔酮形成色素的详细化学机制。