Article: Chemical constituents from acid hydrolyzates of total saponins and their inhibition activity to α-glycosidase and protein tyrosine phosphatase 1B

Objective: To investigate the hypoglycemic components from the acid hydrolyzates of total saponins, and screen the active compounds by inhibitory activities to α-glycosidase enzymes and protein tyrosine phosphatase-1B (PTP1B).

Methods: The hydrolyzates were chromatographed repeatedly over silica gel column, and the structures of the compounds were determined by means of NMR. The bioassay was performed through the inhibitory effects on α-glucosidase or/and PTP1B.

Results: Eight compounds were isolated, which identified as 20()-panaxadiol (), (20,24)-dammarane-20,24-epoxy-3β,6α,12β,25-tetraol (), 20()-dammarane-3β,12β,20,25-tetraol (), 20()-dammarane-3β,6α,12β,20,25-pentol (), 20()-dammarane-3β,12β,20,25-tetrahydroxy-3β--β--glucopyranoside (), β-sitosterol (), oleanolic acid () and 20()-protopanaxadiol (). Compound was ginseng triterpenoid isolated from the acid hydrolysates of total saponins from for the first time. In this paper, the possible inhibitory activities were investigated. Compound exhibited significantly inhibitory activity against α-glucosidase, and the IC value [(0.22 ± 0.21) µmol/L] was about 43-fold lower than positive control. For the PTP1B inhibition assay, compound indicated the strongest inhibitory effect with IC of (5.91 ± 0.38) µmol/L, followed by compound with IC of (6.21 ± 0.21) µmol/L, which were all showed competitive inhibitory pattern by using a Lineweaver-Burk plot.

Conclusion: These results supported the potential application of dammaranes from acid hydrolyzates of total saponins can be used as ingredients of ancillary anti-diabetic agent or functional factor.

Citing Articles

Optimization of saponin extraction from the leaves of and and evaluation of their antioxidant, antihypertensive, hypoglycemic and anti-inflammatory activities.

Liang Z, Guan Y, Lv Z, Yang S, Zhang G, Zhao Y Food Chem X. 2024; 23:101642.

PMID: 39113743 PMC: 11304882. DOI: 10.1016/j.fochx.2024.101642.

Research progress of Chinese herbal medicine compounds and their bioactivities: Fruitful 2020.

Gu X, Hao D, Xiao P Chin Herb Med. 2022; 14(2):171-186.

PMID: 36117669 PMC: 9476823. DOI: 10.1016/j.chmed.2022.03.004.

Integrating Enhanced Profiling and Chemometrics to Unveil the Potential Markers for Differentiating among the Leaves of , and by Ultra-High Performance Liquid Chromatography/Ion Mobility-Quadrupole Time-of-Flight Mass Spectrometry.

Yang F, Chen B, Jiang M, Wang H, Hu Y, Wang H Molecules. 2022; 27(17).

PMID: 36080314 PMC: 9458027. DOI: 10.3390/molecules27175549.

A review for discovering bioactive minor saponins and biotransformative metabolites in L.

Yang Z, Deng J, Liu M, He C, Feng X, Liu S Front Pharmacol. 2022; 13:972813.

PMID: 35979234 PMC: 9376941. DOI: 10.3389/fphar.2022.972813.

Rapid Identification of Characteristic Chemical Constituents of , , and Using UPLC-Q-TOF/MS.

Jinbiao L, Xinyue Z, Shenshen Y, Shuo W, Chengcheng L, Bin Y J Anal Methods Chem. 2022; 2022:6463770.

PMID: 35340764 PMC: 8947929. DOI: 10.1155/2022/6463770.

References

1.

Wang J, Li W, Sha Y, Tezuka Y, Kadota S, Li X . Triterpenoid saponins from leaves and stems of Panax quinquefolium L. J Asian Nat Prod Res. 2001; 3(2):123-30. DOI: 10.1080/10286020108041379. View

2.

Vuksan V, Sievenpiper J, Koo V, Francis T, Xu Z, Vidgen E . American ginseng (Panax quinquefolius L) reduces postprandial glycemia in nondiabetic subjects and subjects with type 2 diabetes mellitus. Arch Intern Med. 2000; 160(7):1009-13. DOI: 10.1001/archinte.160.7.1009. View

3.

Xiao T, Guo Z, Sun B, Zhao Y . Identification of Anthocyanins from Four Kinds of Berries and Their Inhibition Activity to α-Glycosidase and Protein Tyrosine Phosphatase 1B by HPLC-FT-ICR MS/MS. J Agric Food Chem. 2017; 65(30):6211-6221. DOI: 10.1021/acs.jafc.7b02550. View

4.

Cho N, Shaw J, Karuranga S, Huang Y, da Rocha Fernandes J, Ohlrogge A . IDF Diabetes Atlas: Global estimates of diabetes prevalence for 2017 and projections for 2045. Diabetes Res Clin Pract. 2018; 138:271-281. DOI: 10.1016/j.diabres.2018.02.023. View

5.

Qi L, Wang C, Yuan C . American ginseng: potential structure-function relationship in cancer chemoprevention. Biochem Pharmacol. 2010; 80(7):947-54. DOI: 10.1016/j.bcp.2010.06.023. View

6.

Elchebly M, Payette P, Michaliszyn E, Cromlish W, Collins S, Loy A . Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science. 1999; 283(5407):1544-8. DOI: 10.1126/science.283.5407.1544. View

7.

Tao Y, Zhang Y, Cheng Y, Wang Y . Rapid screening and identification of α-glucosidase inhibitors from mulberry leaves using enzyme-immobilized magnetic beads coupled with HPLC/MS and NMR. Biomed Chromatogr. 2012; 27(2):148-55. DOI: 10.1002/bmc.2761. View

8.

Imam K . Clinical features, diagnostic criteria and pathogenesis of diabetes mellitus. Adv Exp Med Biol. 2013; 771:340-55. DOI: 10.1007/978-1-4614-5441-0_25. View

9.

Liu J, Tian X, Liu H, Zhang Q, Lu D, Li P . Two novel dammarane-type compounds from the leaves and stems of Panax quinquefolium L. J Asian Nat Prod Res. 2013; 15(9):974-8. DOI: 10.1080/10286020.2013.794416. View

10.

Meng Y, Su A, Yuan S, Zhao H, Tan S, Hu C . Evaluation of Total Flavonoids, Myricetin, and Quercetin from Hovenia dulcis Thunb. As Inhibitors of α-Amylase and α-Glucosidase. Plant Foods Hum Nutr. 2016; 71(4):444-449. DOI: 10.1007/s11130-016-0581-2. View

11.

Wang P, Bi X, Xu J, Yuan H, Piao H, Zhao Y . Synthesis and anti-tumor evaluation of novel 25-hydroxyprotopanaxadiol analogs incorporating natural amino acids. Steroids. 2012; 78(2):203-9. DOI: 10.1016/j.steroids.2012.09.012. View

Chemical Constituents from Acid Hydrolyzates of Total Saponins and Their Inhibition Activity to α-glycosidase and Protein Tyrosine Phosphatase 1B