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Hydrolysis patterns of enzymatically modified steviol glycosides
Myeong Ji Kim1, Jeong-Eun Lee1, Young-Sam Keum1
1College of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Goyang 10326, Republic of Korea.
Abstract:
Enzymatically modified steviol glycosides (EMS) are structurally enhanced derivatives designed to improve palatability. This study investigates the acidic degradation of EMS, revealing a significant alternative pathway compared to natural stevia. While natural glycosides primarily yield isosteviol, acid-hydrolyzed EMS produces a distinct byproduct identified as ent-13-hydroxykaur-15-en-19-oic acid (1). Structural characterization via HRMS, NMR, and X-ray diffraction confirmed its identity, with formation being highly pH and time-dependent. Comparative HPLC analysis showed that while compound 1 is minimal in natural stevia, it is substantially pronounced in EMS. These findings indicate that extensive glucosylation alters the chemical behavior of the steviol backbone under acidic conditions. These results suggest that incorporating this byproduct into the current analytical framework for steviol equivalents could provide a more precise assessment for products containing EMS.
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