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Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin

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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.

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Reaction coupling separation for isosteviol production catalyzed by acidic ion-exchange resin.

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Acknowledgements

Financial support from National Natural Science Foundation of China (31772017, 31371837), the national first-class discipline program of Light Industry Technology and Engineering (LITE2018-03), and the project of outstanding scientific & technological innovation group of Jiangsu Province are gratefully appreciated.

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Authors and Affiliations

  1. State Key Laboratory of Food Science and Technology, School of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Avenue, Wuxi, 214122, Jiangsu, China

    Xueyi Hu, Zhuoyu Zhou, Zongying Zhang, Xiaoxia Wang, Xiaochen Sui, Junming Chen & Yongmei Xia

  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

    Xueyi Hu, Zhuoyu Zhou, Zongying Zhang, Xiaoxia Wang, Xiaochen Sui, Junming Chen & Yongmei Xia

  3. Key Laboratory of Nuclear Medicine of Ministry of Health, Jiangsu Institute of Nuclear Medicine, Wuxi, 214063, Jiangsu, China

    Jue Zhang & Jianguo Lin

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  1. Xueyi Hu
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Correspondence to Yongmei Xia.

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Hu, X., Zhou, Z., Zhang, Z. et al. Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin. Bioprocess Biosyst Eng 44, 151–159 (2021). https://doi.org/10.1007/s00449-020-02431-4

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