Studies on the Composition and Glycoside Hydrolysis of Glycosides of 3-Oxo-ionol in Loquat Leaves

Yuan Lin; Yuchen Zhou; Yongjiang Wang; Li Zhang; Shengxiong Huang

doi:10.6919/ICJE.202504_11(4).0012

Authors

Yuan Lin
Yuchen Zhou
Yongjiang Wang
Li Zhang
Shengxiong Huang

DOI:

https://doi.org/10.6919/ICJE.202504_11(4).0012

Keywords:

3-oxo-ionol; 3-oxo-ionol Glycosides; Loquat Leaves; Acidic Hydrolysis; Enzymatic Hydrolysis.

Abstract

3-Oxo-ionol, a flavor compound with low natural abundance, serves as a distinctive flavoring agent in various products such as wine and cigarettes. To find an alternative resource of 3-oxo-ionol, six 3-oxo-α-ionol glycosides and their analogs were isolated from loquat leaves. These compounds were identifies as (6R,7E,9R)-9-hydroxy-4,7-megastigmadien-3-one 9-O-β-D-glucopyranoside (1), (Z)-6-[9-(β-D-glucopyranosyloxy)butylidene]-5,1,1-trimethyl-4-cyclohexen-3-one (2), (6R,7E,9S)-9-hydroxy-4,7-megastigmadien-3-one 9-O-β-D-glucopyranoside (3), blumeol C glucoside (4), (6S,9R) roseoside (6), and (6S,9S) roseoside (7). Among them, compounds 2 and 4 were isolated from loquat leaves for the first time. Comparison of acid and enzymatic hydrolysis revealed that acid hydrolysis is more practical for hydrolyzing 3-oxo-α-ionol glycosides. After optimizing acid concentrations, compound 3 reached a hydrolysis efficiency of 35.6% with 2.0 M HCl. This method was applicable to other 3-oxo-α-ionol glycosides, offering a solution for the production of 3-oxo-ionol. This study not only presented a method for obtaining 3-oxo-ionol, but also expanded its production strategies, facilizing further research and application of these valuable compounds.

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