471-80-7Relevant articles and documents
Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin
Hu, Xueyi,Zhou, Zhuoyu,Zhang, Zongying,Wang, Xiaoxia,Sui, Xiaochen,Chen, Junming,Xia, Yongmei,Zhang, Jue,Lin, Jianguo
, p. 151 - 159 (2020/09/01)
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.[Figure not available: see fulltext.]
A complete specific cleavage of glucosyl and ester linkages of stevioside for preparing steviol with a β-galactosidase from Sulfolobus solfataricus
Chen, Jun-Ming,Xia, Yong-Mei,Wan, Hui-Da,Wang, Hai-Jun,Liu, Xiang
, p. 126 - 131 (2014/06/10)
β-Galactosidases from Sulfolobus solfataricus have been used to synthesize galactooligosaccharide and lactulose. In this work, a β-galactosidase from S. solfataricus with weak β-glucosidase activity but high lipase activity was employed as catalyst to assist hydrolysis of stevioside to obtain steviol, an important starting reagent of synthetic bioactive materials and the main metablite of stevioside in human digistion. The β-galactosidase presented a strict substrate specifity on converting stevioside to steviol in a stoichiometric yield. The β-galactosidase favors the cleavage of glycoside linkages prior to cleavage of glycosyl ester linkage. The hydrolysis is external diffusion controlled and hence has to bear low substrate concentration in regular process, but this can be solved with product removal or enzyme immobilization. The immobilization of the β-galactosidase onto cross-linked chitosan microspheres did not enhance the enzyme's thermal or pH stability but eliminated the external diffusion, and therefore speeded the hydrolysis in 3 folds. The relative reaction activity dropped only 1.75% after 6 runs of using the immobilized β-galactosidase.
Minor diterpenoid glycosides from the leaves of Stevia rebaudiana
Chaturvedula, Venkata Sai Prakash,Clos, John F.,Rhea, Joshua,Milanowski, Dennis,Mocek, Ulla,Dubois, Grant E.,Prakash, Indra
experimental part, p. 209 - 212 (2012/05/04)
From the commercial extract of the leaves of Stevia rebaudiana, three new diterpenoid glycosides were isolated besides eight known steviol glycosides including stevioside, rebaudiosides A-F and dulcoside A. The structures of the three compounds were identified as 13-[(2-O-β-d-glucopyranosyl-β-d- glucopyranosyl) oxy]-kaur-16-en-18-oic acid-(6-O-β-d-xylopyranosyl-β- d-glucopyranosyl) ester (1), 13-[(2-O-β-d-glucopyranosyl-β-d- glucopyranosyl) oxy]-17-hydroxy-kaur-15-en-18-oic acid β-d-glucopyranosyl ester (2), and 13-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]-17-oxo-kaur-15-en-18-oic acid β-d-glucopyranosyl ester (3) on the basis of extensive NMR and MS spectral studies. Another known diterpenoid glycoside, 13-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]-kaur-15-en-18-oic acid β-d-glucopyranosyl ester (4) was also isolated and its complete NMR spectral assignments were made on the basis of COSY, HSQC and HMBC spectral data.
