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Research Article

New dammarane-type triterpenoids from hydrolyzate of total Gynostemma pentaphyllum saponins with protein tyrosine phosphatase 1B inhibitory activity

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Article: 2281263 | Received 21 Sep 2023, Accepted 05 Nov 2023, Published online: 15 Nov 2023

References

  • Cloete L. Diabetes mellitus: an overview of the types, symptoms, complications and management. Nurs Stand. 2022;37(1):61–66.
  • Sun Y, Tao Q, Wu X, Zhang L, Liu Q, Wang L. The utility of exosomes in diagnosis and therapy of diabetes mellitus and associated complications. Front Endocrinol. 2021;12:756581.
  • Liu R, Mathieu C, Berthelet J, Zhang W, Dupret JM, Rodrigues Lima F. Human protein tyrosine phosphatase 1B (PTP1B): from structure to clinical inhibitor perspectives. Int J Mol Sci. 2022;23 (13):7027.
  • Tamrakar AK, Maurya CK, Rai AK. PTP1B inhibitors for type 2 diabetes treatment: a patent review (2011–2014). Expert Opin Ther Pat. 2014;24(10):1101–1115.
  • Nandi S, Saxena M. Potential inhibitors of protein tyrosine phosphatase (PTP1B) enzyme: promising target for type-II diabetes mellitus. Curr Top Med Chem. 2020;20(29):2692–2707.
  • Hussain H, Green IR, Abbas G, Adekenov SM, Hussain W, Ali I. Protein tyrosine phosphatase 1B (PTP1B) inhibitors as potential anti-diabetes agents: patent review (2015–2018). Expert Opin Ther Pat. 2019;29(9):689–702.
  • Teimouri M, Hosseini H, ArabSadeghabadi Z, Babaei-Khorzoughi R, Gorgani-Firuzjaee S, Meshkani R. The role of protein tyrosine phosphatase 1B (PTP1B) in the pathogenesis of type 2 diabetes mellitus and its complications. J Physiol Biochem. 2022;78(2):307–322.
  • Tan D, Wang J, Cao L, Yang D, Lu Y, Wu D, Zhao Y, Wu X, Fan Q, Yang Z, et al. UDP-glycosyltransferases play a crucial role in the accumulation of alkaloids and sesquiterpene glycosides in Dendrobium nobile. Arabian J Chem . 2023;16(5):104673.
  • Yin F, Hu L, Lou F, Pan R. Dammarane-type glycosides from Gynostemma pentaphyllum. J Nat Prod. 2004;67(6):942–952.
  • Yang F, Shi H, Zhang X, Yu LL. Two novel anti-inflammatory 21-nordammarane saponins from tetraploid Jiaogulan (Gynostemma pentaphyllum). J Agric Food Chem. 2013;61(51):12646–12652.
  • Zhou T, Cao L, Du Y, Qin L, Lu Y, Zhang Q, He Y, Tan D. Gypenosides ameliorate high-fat diet-induced nonalcoholic fatty liver disease in mice by regulating lipid metabolism. PeerJ. 2023;11:e15225.
  • Razmovski-Naumovski V, Huang HW, Tran VH, Li GQ, Duke CC, Roufogalis BD. Chemistry and Pharmacology of Gynostemma pentaphyllum. Phytochem Rev. 2005;4(2–3):197–219.
  • Zhang X, Shi G, Sun Y, Wu X, Zhao Y. Triterpenes derived from hydrolyzate of total Gynostemma pentaphyllum saponins with anti-hepatic fibrosis and protective activity against H(2)O(2)-induced injury. Phytochemistry. 2017;144:226–232.
  • Wang J, Ha TKQ, Shi YP, Oh WK, Yang JL. Hypoglycemic triterpenes from Gynostemma pentaphyllum. Phytochemistry. 2018;155:171–181.
  • Cui WY, Jin Y, Liu H, Zu ML, Zhai XF, Yang C, Gu YL, Cheng Y, Piao XL. Dammarane-type saponins from Gynostemma pentaphyllum and their cytotoxicities. Nat Prod Res. 2021;35(22):4433–4441.
  • Lee C, Lee JW, Jin Q, Jang H, Jang HJ, Rho MC, Lee MK, Lee CK, Lee MK, Hwang BY. Isolation and characterization of dammarane-type saponins from Gynostemma pentaphyllum and their inhibitory effects on IL-6-induced STAT3 activation. J Nat Prod. 2015;78(5):971–976.
  • Wang J, Yang JL, Zhou PP, Meng XH, Shi YP. Further new gypenosides from Jiaogulan (Gynostemma pentaphyllum). J Agric Food Chem. 2017;65(29):5926–5934.
  • Hung TM, Thu CV, Cuong TD, Hung NP, Kwack SJ, Huh JI, Min BS, Choi JS, Lee HK, Bae K. Dammarane-type glycosides from Gynostemma pentaphyllum and their effects on IL-4-induced eotaxin expression in human bronchial epithelial cells. J Nat Prod. 2010;73(2):192–196.
  • Huang TH, Razmovski-Naumovski V, Salam NK, Duke RK, Tran VH, Duke CC, Roufogalis BD. A novel LXR-alpha activator identified from the natural product Gynostemma pentaphyllum. Biochem Pharmacol. 2005;70(9):1298–1308.
  • Circosta C, De Pasquale R, Occhiuto F. Cardiovascular effects of the aqueous extract of Gynostemma pentaphyllum Makino. Phytomedicine. 2005;12(9):638–643.
  • Xie Z, Liu W, Huang H, Slavin M, Zhao Y, Whent M, Blackford J, Lutterodt H, Zhou H, Chen P, et al. Chemical composition of five commercial Gynostemma pentaphyllum samples and their radical scavenging, antiproliferative, and anti-inflammatory properties. J Agric Food Chem. 2010;58(21):11243–11249.
  • Lin CC, Huang PC, Lin JM. Antioxidant and hepatoprotective effects of Anoectochilus formosanus and Gynostemma pentaphyllum. Am J Chin Med. 2000;28(1):87–96.
  • Li N, Wu CF, Xu XY, Liu ZY, Li X, Zhao YQ. Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum. Eur J Med Chem. 2012;50:173–178.
  • Zhang XS, Bi XL, Wan X, Cao JQ, Xia XC, Diao YP, Zhao YQ. Protein tyrosine phosphatase 1B inhibitory effect by dammarane-type triterpenes from hydrolyzate of total Gynostemma pentaphyllum saponins. Bioorg Med Chem Lett. 2013;23(1):297–300.
  • Xu JQ, Shen Q, Li J, Hu LH. Dammaranes from Gynostemma pentaphyllum and synthesis of their derivatives as inhibitors of protein tyrosine phosphatase 1B. Bioorg Med Chem. 2010;18(11):3934–3939.
  • Zhou X, Wang LL, Tang WJ, Tang B. Astragaloside IV inhibits protein tyrosine phosphatase 1B and improves insulin resistance in insulin-resistant HepG2 cells and triglyceride accumulation in oleic acid (OA)-treated HepG2 cells. J Ethnopharmacol. 2021;268:113556.
  • Varadi M, Anyango S, Deshpande M, Nair S, Natassia C, Yordanova G, Yuan D, Stroe O, Wood G, Laydon A, et al. AlphaFold protein structure database: massively expanding the structural coverage of protein-sequence space with high-accuracy models. Nucleic Acids Res. 2022;50(D1):D439–D444.
  • Jumper J, Evans R, Pritzel A, Green T, Figurnov M, Ronneberger O, Tunyasuvunakool K, Bates R, Žídek A, Potapenko A, et al. Highly accurate protein structure prediction with AlphaFold. Nature. 2021;596(7873):583–589.
  • Montalibet J, Skorey K, McKay D, Scapin G, Asante-Appiah E, Kennedy BP. Residues distant from the active site influence protein-tyrosine phosphatase 1B inhibitor binding. J Biol Chem. 2006;281(8):5258–5266.
  • Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017;7(1):42717.
  • Gan M, Liu M, Gan L, Lin S, Liu B, Zhang Y, Zi J, Song W, Shi J. Dammarane glycosides from the root of Machilus yaoshansis. J Nat Prod. 2012;75(7):1373–1382.
  • Barford D, Flint AJ, Tonks NK. Crystal structure of human protein tyrosine phosphatase 1B. Science. 1994;263(5152):1397–1404.
  • Tautz L, Critton DA, Grotegut S. Protein tyrosine phosphatases: structure, function, and implication in human disease. Methods Mol Biol. 2013;1053:179–221.
  • Sympli HD. Estimation of drug-likeness properties of GC-MS separated bioactive compounds in rare medicinal Pleione maculata using molecular docking technique and SwissADME in silico tools. Netw Model Anal Health Inform Bioinform. 2021;10(1):14.
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 2001;46(1–3):3–26.
  • Azman M, Sabri AH, Anjani QK, Mustaffa MF, Hamid KA. Intestinal absorption study: challenges and absorption enhancement strategies in improving oral drug delivery. Pharmaceuticals. 2022;15(8):975.