Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin
- PDF / 1,484,825 Bytes
- 9 Pages / 595.276 x 790.866 pts Page_size
- 90 Downloads / 188 Views
RESEARCH PAPER
Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion‑exchange resin Xueyi Hu1,2 · Zhuoyu Zhou1,2 · Zongying Zhang1,2 · Xiaoxia Wang1,2 · Xiaochen Sui1,2 · Junming Chen1,2 · Yongmei Xia1,2 · Jue Zhang3 · Jianguo Lin3 Received: 17 December 2019 / Accepted: 17 August 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Isosteviol, a prodrug used to be obtained via Wagner–Meerwein rearrangement from steviol with low yield and long reaction time. Herein, an in-situ separation-coupling-reaction is presented to prepare isosteviol from the natural sweetener stevioside. Simply with in-situ water-washing, the product containing 92.98% purity of isosteviol was obtained with a stevioside conversion of 97.23% from a packet bed reactor without further separation. Within the assayed inorganic acid, organic acids and acidic ionic liquids, the acidic ion-exchange resins provided higher product specificity towards isosteviol. Furthermore, comparing to 5-Fluorouracil, the product presented similar and even stronger inhibition on proliferation of the assayed human cancer cells in a time and dose-dependence by causing cell phase arrest. Isosteviol treatment caused G1 arrest on SGC-7901, HCT-8 and HCT-116 cells, S arrest on HepG2, Huh-7 and HepG3B cells, and G2 arrest on MGC-803 cells, respectively. Graphic abstract Reaction coupling separation for isosteviol production catalyzed by acidic ion-exchange resin.
Keywords Isosteviol · Stevioside · Hydrolysis · Cation-exchange resin · Anticancer · Ionic liquid Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00449-020-02431-4) contains supplementary material, which is available to authorized users. * Yongmei Xia [email protected] 1
State Key Laboratory of Food Science and Technology, School of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Avenue, Wuxi 214122, Jiangsu, China
2
Key Laboratory of Synthetic and Biological Colloids (Ministry of Education), School of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Avenue, Wuxi 214122, Jiangsu, China
3
Key Laboratory of Nuclear Medicine of Ministry of Health, Jiangsu Institute of Nuclear Medicine, Wuxi 214063, Jiangsu, China
Introduction Isosteviol, (4α, 8β, 13β)-13-Methyl-16-oxo-17-norkauran18-oic acid, was reported on its structure, stereochemistry [1] and absolute configuration in 1960s [2]. To date, isosteviol has been mostly recognizing as a popular starting material for drug synthesis [3–7]; for instance, as precursors of synthetic drugs for the treatment of cancer and inflammation [8, 9]. Recently, isosteviol itself has gained intensive interests as it possesses various biological activities [10], such as reducing vasoconstriction [11], improving glucose and insulin sensitivity, lowering plasma triglycerides and weight,
13
Vol.:(0123456789)
and regulating the gene expression profile of key insulin regulatory genes for the treatment of type II dia
Data Loading...
