Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin.,Bioprocess and Biosystems Engineering

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Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin.
Bioprocess and Biosystems Engineering ( IF 3.8 ) Pub Date : 2020-08-28 , DOI: 10.1007/s00449-020-02431-4
Xueyi Hu _{1,

2} , Zhuoyu Zhou _{1,

2} , Zongying Zhang _{1,

2} , Xiaoxia Wang _{1,

2} , Xiaochen Sui _{1,

2} , Junming Chen _{1,

2} , Yongmei Xia _{1,

2} , Jue Zhang ₃ , Jianguo Lin ₃

Affiliation

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.

中文翻译：

酸性离子交换树脂催化甜菊糖生产异甜菊醇的反应偶联分离

摘要

异甜菊醇是一种前药，过去通过 Wagner-Meerwein 重排从甜菊醇中获得，收率低，反应时间长。在此，提出了一种原位分离-偶联-反应，以从天然甜味剂甜菊糖中制备异甜菊醇。简单地通过原位水洗，从包床反应器中获得含有 92.98% 纯度异甜菊醇的产品，甜菊糖苷转化率为 97.23%，无需进一步分离。在测定的无机酸、有机酸和酸性离子液体中，酸性离子交换树脂对异甜菊醇提供了更高的产品特异性。此外，与 5-氟尿嘧啶相比，该产品通过引起细胞相位停滞，在时间和剂量依赖性方面对所测定的人类癌细胞的增殖具有相似甚至更强的抑制作用。