Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Sep 3;28(17):6415.
doi: 10.3390/molecules28176415.

The Content and Principle of the Rare Ginsenosides Produced from Gynostemma pentaphyllum after Heat Treatment

Xin-Can Li  1 , Fang-Fang Li  1 , Wen-Jing Pei  1 , Jing Yang  1 , Yu-Long Gu  1 , Xiang-Lan Piao  1
Affiliations

The Content and Principle of the Rare Ginsenosides Produced from Gynostemma pentaphyllum after Heat Treatment

Xin-Can Li et al. Molecules. .

Abstract

Ginsenoside Rg3, Rk1, and Rg5, rare ginsenosides from Panax ginseng, have many pharmacological effects, which have attracted extensive attention. They can be obtained through the heat treatment of Gynostemma pentaphyllum. In this study, scanning electron microscopy (SEM) and thermal gravity-differential thermal gravity (TG-DTG) were employed to investigate this process and the content change in ginsenosides was analyzed using liquid chromatography-mass spectrometry (LC-MS). SEM and TG-DTG were used to compare the changes in the ginsenosides before and after treatment. In SEM, the presence of hydrogen bond rearrangement was indicated by the observed deformation of vascular bundles and ducts. The before-and-after changes in the peak patterns and peaks values in TG-DTG indicated that the content of different kinds of compounds produced changes, which all revealed that the formation of new saponins before and after the heat treatment was due to the breakage or rearrangement of chemical bonds. Additionally, the deformation of vascular bundles and vessels indicated the presence of hydrogen bond rearrangement. The glycosidic bond at the 20 positions could be cleaved by ginsenoside Rb3 to form ginsenoside Rd, which, in turn, gave rise to ginsenoside Rg3(S) and Rg3(R). They were further dehydrated to form ginsenoside Rk1 and Rg5. This transformation process occurs in a weak acidic environment provided by G. pentaphyllum itself, without the involvement of endogenous enzymes. In addition, the LC-MS analysis results showed that the content of ginsenoside Rb3 decreased from 2.25 mg/g to 1.80 mg/g, while the contents of ginsenoside Rk1 and Rg5 increased from 0.08 and 0.01 mg/g to 3.36 and 3.35 mg/g, respectively. Ginsenoside Rg3(S) and Rg3(R) were almost not detected in G. pentaphyllum, and the contents of them increased to 0.035 and 0.23 mg/g after heat treatment. Therefore, the rare ginsenosides Rg3(S), Rg3(R), Rk1, and Rg5 can be obtained from G. pentaphyllum via heat treatment.

Keywords: Gynostemma pentaphyllum; LC-MS; SEM; TG-DTG; ginsenoside.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Scanning electron micrographs (SEM) for G. pentaphyllum leaves before (A,B) and after (C,D) heat treatment.
Figure 2
Figure 2
TG-DTG curves of leaves of G. pentaphyllum before (A) and after (B) heat treatment.
Figure 3
Figure 3
Total ion chromatograms of G. pentaphyllum. Extract of G. pentaphyllum before (A) and after (B) heat treatment. Reference standards ginsenoside Rg3(S) (C), Rg3(R) (D), Rk1 (E), and Rg5 (F).
Figure 4
Figure 4
Total ion chromatogram of ginsenoside Rb3 and Rd before and after heat treatment. (A) 100 μg/mL of ginsenoside Rb3 solution was injected 1 μL to LC-MS. (B) 100 μg/mL of Rb3 solution was steamed for 3 h at 120 °C, 0.24 MPa and injected 1 μL to LC-MS. (C) 100 μg/mL of ginsenoside Rd solution was injected 1 μL to LC-MS. (D) 100 μg/mL of Rd solution was steamed for 3 h at 120 °C, 0.24 MPa and injected 1 μL to LC-MS.
Figure 5
Figure 5
Multi ion chromatogram (MIC) of G. pentaphyllum mixed with polar ginsenosides. In total, 100 mg of G. pentaphyllum was mixed with 500 μL of 100 μg/mL of ginsenoside Rb3 (A) or 100 μg/mL of Rd (C) and extracted with 80% methanol to a volume of 20 mL. In total, 100 mg of G. pentaphyllum was mixed with 500 μL of 100 μg/mL of Rb3 (B) or 100 μg/mL of Rd (D) and steamed for 3 h at 120 °C, 0.24 MPa, and extracted with 80% methanol to a volume of 20 mL. The extracts were filtered through 0.22 μm microporous membranes.
Figure 6
Figure 6
Proposed pathway of ginsenosides of G. pentaphyllum after heat treatment.
Figure 7
Figure 7
LC-MRM-MS of the extract of G. pentaphyllum. (A) Mixed standard reference solution. (B) Extract of G. pentaphyllum. (C) Extract of heat-processed G. pentaphyllum.
See this image and copyright information in PMC

References

    1. Man S., Luo C., Yan M., Zhao G., Ma L., Gao W. Treatment for liver cancer: From sorafenib to natural products. Eur. J. Med. Chem. 2021;224:113690. doi: 10.1016/j.ejmech.2021.113690. - DOI - PubMed
    1. Lu H., Yin H., Qu L., Ma X., Fu R., Fan D. Ginsenoside Rk1 regulates glutamine metabolism in hepatocellular carcinoma through inhibition of the ERK/c-Myc pathway. Food Funct. 2022;13:3793–3811. doi: 10.1039/D1FO03728E. - DOI - PubMed
    1. Liu Y., Fan D. The Preparation of Ginsenoside Rg5, Its Antitumor Activity against Breast Cancer Cells and Its Targeting of PI3K. Nutrients. 2020;12:246. doi: 10.3390/nu12010246. - DOI - PMC - PubMed
    1. Liu H., Zhao J., Fu R., Zhu C., Fan D. The ginsenoside Rk3 exerts anti-esophageal cancer activity in vitro and in vivo by mediating apoptosis and autophagy through regulation of the PI3K/Akt/mTOR pathway. PLoS ONE. 2019;14:e0216759. doi: 10.1371/journal.pone.0216759. - DOI - PMC - PubMed
    1. Ni J., Liu Z., Jiang M., Li L., Deng J., Wang X., Su J., Zhu Y., He F., Mao J., et al. Ginsenoside Rg3 ameliorates myocardial glucose metabolism and insulin resistance via activating the AMPK signaling pathway. J. Ginseng Res. 2022;46:235–247. doi: 10.1016/j.jgr.2021.06.001. - DOI - PMC - PubMed

LinkOut - more resources