Conversion Rule of Rare Ginsenosides Produced from Major Ginsenosides by Confined Microiwave Promoted Degradation Method†

doi:10.7503/cjcu20140641

Abstract

Abstract:

In order to prepare the rare ginsenosides which were considered to have higher bioactivities, confined microwave method to promote the degradation of 7 kinds of major ginsenosides(Rb₁, Rb₂, Rb₃, Rc, Rd, Re, Rg₁) to rare ginsenosides were adopted. Comparing with the degradation products of non-microwave method at the same condition, the rules of conversion about the structures and ingredients of degradation products were concluded by HPLC analysis. The results indicated that confined microwave method can completely degrade all the major ginsenosides, while nearly no major ginsenosides can be degraded under the same condition of non-microwave method. Protopanaxadiol-type ginsenosides were easily deglycosylated at C20, where the conformational changes would take place. It would generate 20(S)-Rg₃ and 20(R)-Rg₃ among which the R-type was the superior configuration. Dehydration effect of the hydroxyl at C20 made 20(S/R)-Rg₃ convert to Rk₁ and Rg₅, meanwhile the losing of glucose of 20(S/R)-Rg₃ at C3 position made the generation of 20(S/R)-Rh₂. After further dehydration at C20 position, 20(S/R)-Rh₂ converted to Rk₂ and Rh₃. Moreover, the configurations of glycosyls at C20 of ginsenosides would affect the proportion and composition of rare ginse-nosides in degradation products, but Rg₅ reached highest content in all confined microwave degradation products of 7 kinds of protopanaxadiol-type ginsenosides. Protopanaxatriol-type ginsenosides had similar rules with protopanaxadiol-type ginsenosides by the confined microwave degradation method, and the products of Re and Rg₁ were determined in the highest content of Rh₄.

Key words: Microwave degradation, High performance liquid chromatography(HPLC), Rare ginsenoside, Conversion

CLC Number:

O657
O629

TrendMD:

YAO Hua, JIN Yongri, YANG Jie, LI Lanjie, SUN Ting, SHI Xiaolei, LI Xuwen. Conversion Rule of Rare Ginsenosides Produced from Major Ginsenosides by Confined Microiwave Promoted Degradation Method^†[J]. Chem. J. Chinese Universities, 2014, 35(11): 2317.

Figures/Tables 5

Fig.1 HPLC chromatogram of major ginsenosides Peak: 1. Rg1; 2. Re; 3. Rb1; 4. Rc;5. Rb2; 6. Rb3; 7. Rd.

Fig.2 HPLC chromatogram of rare ginsenosides Peak: 1. 20(S)-Rh1; 2. 20(R)-Rh1; 3. Rg6; 4. F4; 5. Rk3; 6. Rh4; 7. 20(S)-Rg3; 8. 20(R)-Rg3; 9. Rk1; 10. Rg5; 11. 20(S)-Rh2; 12. Rk2; 13. Rh3.

Fig.3 HPLC chromatograms of major ginsenosides treated by high temperature and pressure method a. Rg1; b. Rb1; c. Re; d. Rd; e. Rb2; f. Rb3; g. Rc. Peak: 1. Rg1; 2. Re; 3. Rb1; 4. Rc; 5. Rb2; 6. Rb3; 7. Rd; 8. 20(S)-Rg3; 9. 20(R)-Rg3; 10. Rk1; 11. Rg5.

Fig.4 HPLC chromatograms of major ginsenosides treated by confined microwave method a. Rb1; b. Rb2; c. Re; d. Rg1; e. Rb3; f. Rc; g. Rd. Peak: 1. 20(S)-Rh1; 2. 20(R)-Rh1; 3. Rg6; 4. F4; 5. Rk3; 6. Rh4; 7. 20(S)-Rg3; 8. 20(R)-Rg3; 9. Rk1; 10. Rg5; 11. 20(S)-Rh2; 12. Rk2; 13. Rh3.

Fig.5 Peak areas of major ginsenosides degradation products of confined microwave() and high temperature and pressure() method (A) Rb1. a. Rb1, b. 20(S)-Rg3, c. 20(R)-Rg3, d. Rk1, e. Rg5, f. Rh2, g. Rk2, h. Rh3; (B) Rb2. a. Rb2, b. 20(S)-Rg3, c. 20(R)-Rg3, d. Rk1, e. Rg5, f. Rh2, g. Rk2, h. Rh3; (C) Rb3. a. Rb3, b. 20(S)-Rg3, c. 20(R)-Rg3, d. Rk1, e. Rg5, f. Rh2, g. Rk2, h. Rh3; (D) Rc. a. Rc, b. 20(S)-Rg3, c. 20(R)-Rg3, d. Rk1, e. Rg5, f. Rh2, g. Rk2, h. Rh3; (E) Rd. a. Rd, b. 20(S)-Rg3, c. 20(R)-Rg3, d. Rk1, e. Rg5, f. Rh2, g. Rk2, h. Rh3; (F) Re. a. Re, b. 20(S)-Rh1, c. 20(R)-Rh1, d. Rg6, e. F4, f. Rk3, g. Rh4, h. Rg2; (G) Rg1. a. Rg1, b. 20(S)-Rh1, c. 20(R)-Rh1, d. Rg6, e. F4, f. Rk3, g. Rh4.

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