Skip to main content
Log in

Flavonol glycosides from the aerial parts of Gynostemma pentaphyllum and their antioxidant activity

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

The phytochemical investigation of the aerial parts of Gynostemma pentaphyllum led to the isolation of a new flavonol glycoside, gynopentaphylloside (1), along with seven known compounds (28). The structure of the new compound was determined on the basis of 1D, 2D NMR and HRESIMS data as well as acid hydrolysis. The antioxidant activity of the isolates was evaluated by a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Abraham LCN, Masakuni T, Isao H, Hajime T (2008) Antioxidant flavonoid glycosides from the leaves of Ficus pumila L. Food Chem 109:415–420

    Article  Google Scholar 

  • Cheng TC, Lu JF, Wang JS, Lin LJ, Kuo HI, Chen BH (2011) Antiproliferation effect and apoptosis mechanism of prostate cancer cell PC-3 by flavonoids and saponins prepared from Gynostemma pentaphyllum. J Agric Food Chem 59:11319–11329

    Article  CAS  PubMed  Google Scholar 

  • Choi HS, Park MS, Kim SH, Hwang BY, Lee CK, Lee MK (2010) Neuroprotective effects of herbal ethanol extracts from Gynostemma pentaphyllum in the 6-hydroxydopamine-lesioned rat model of Parkinson’s disease. Molecules 15:2814–2824

    Article  CAS  PubMed  Google Scholar 

  • Gao D, Zhao M, Qi X, Liu Y, Li N, Liu Z, Bian Y (2016) Hypoglycemic effect of Gynostemma pentaphyllum saponins by enhancing the Nrf2 signaling pathway in STZ-inducing diabetic rats. Arch Pharm Res 39:221–230

    Article  CAS  PubMed  Google Scholar 

  • Hu LH, Chen ZL, Xie YY (1997) Dammarane-type glycosides from Gynostemma pentaphyllum. Phytochemistry 44:667–670

    Article  CAS  Google Scholar 

  • Im SA, Choi HS, Choi SO, Kim KH, Lee S, Hwang BY, Lee MK, Lee CK (2012) Restoration of electric footshock-induced immunosuppression in mice by Gynostemma pentaphyllum components. Molecules 17:7695–7708

    Article  CAS  PubMed  Google Scholar 

  • Iñigo RPA, Pomilio AB (1985) Flavonoids from Erythroxylon argentinum. Phytochemistry 24:347–349

    Article  Google Scholar 

  • Kao TH, Huang SC, Inbaraj BS, Chen BH (2008) Determination of flavonoids and saponins in Gynostemma pentaphyllum (Thunb.) Makino by liquid chromatography–mass spectrometry. Anal Chim Acta 626:200–211

    Article  CAS  PubMed  Google Scholar 

  • Kazuma K, Noda N, Suzuki M (2003) Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry 62:229–237

    Article  CAS  PubMed  Google Scholar 

  • Kijima H, Ide T, Otsuka H, Takeda Y (1995) Alangiflavoside, a new flavonol glycoside from the leaves of Alangium premnifolium. J Nat Prod 58:1753–1755

    Article  CAS  Google Scholar 

  • Lee HB, Kim EK, Park SJ, Bang SG, Kim TG, Chung DW (2010) Isolation and characterization of nicotiflorin obtained by enzymatic hydrolysis of two precursors in tea seed extract. J Agric Food Chem 58:4808–4813

    Article  CAS  PubMed  Google Scholar 

  • Lee C, Lee JW, Jin Q, Jang H, Jang HJ, Rho MC, Lee MK, Lee CK, Lee MK, Hwang BY (2015) Isolation and characterization of dammarane-type saponins from Gynostemma pentaphyllum and their inhibitory effects on IL-6-induced STAT3 activation. J Nat Prod 78:971–976

    Article  CAS  PubMed  Google Scholar 

  • Li B, Zhang X, Wang M, Jiao L (2015) Characterization and antioxidant activities of acidic polysaccharides from Gynostemma pentaphyllum (Thunb.) Markino. Carbohydr Polym 127:209–214

    Article  CAS  PubMed  Google Scholar 

  • Malek MA, Hoang MH, Jia Y, Lee JH, Jun HJ, Lee DH, Lee HJ, Lee C, Lee MK, Hwang BY, Lee SJ (2013) Ombuin-3-O-β-d-glucopyranoside from Gynostemma pentaphyllum is a dual agonistic ligand of peroxisome proliferator-activated receptors α and δ/β. Biochem Biophys Res Commun 430:1322–1328

    Article  CAS  PubMed  Google Scholar 

  • Niu Y, Shang P, Chen L, Zhang H, Gong L, Zhang X, Yu W, Xu Y, Wang Q, Yu LL (2014) Characterization of a novel alkali-soluble heteropolysaccharide from tetraploid Gynostemma pentaphyllum Makino and its potential anti-inflammatory and antioxidant properties. J Agric Food Chem 62:3783–3790

    Article  CAS  PubMed  Google Scholar 

  • Park SY, Kim JS, Lee SY, Bae KH, Kang SS (2008) Chemical constituents of Lathyrus davidii. Nat Prod Sci 14:281–288

    CAS  Google Scholar 

  • Razmovski-Naumovski V, Huang THW, Tran VH, Li GQ, Duke CC, Roufogalis BD (2005) Chemistry and pharmacology of Gynostemma pentaphyllum. Phytochem Rev 4:197–219

    Article  CAS  Google Scholar 

  • Scheer T, Wichtl M (1987) On the occurrence of Kaempferol-4′-O-beta-d-glucopyranoside in Filipendula ulmaria and Allium cepa. Planta Med 53:573–574

    Article  CAS  PubMed  Google Scholar 

  • Selenge E, Murata T, Kobayashi K, Batkhuu J, Yoshizaki F (2013) Flavone tetraglycosides and benzyl alcohol glycosides from the Mongolian medicinal plant Dracocephalum ruyschiana. J Nat Prod 76:186–193

    Article  CAS  PubMed  Google Scholar 

  • Shin KS, Zhao TT, Choi HS, Hwang BY, Lee CK, Lee MK (2014) Effects of gypenosides on anxiety disorders in MPTP-lesioned mouse model of Parkinson’s disease. Brain Res 1567:57–65

    Article  CAS  PubMed  Google Scholar 

  • Suntararuks S, Yoopan N, Rangkadilok N, Worasuttayangkurn L, Nookabkaew S, Satayavivad J (2008) Immunomodulatory effects of cadmium and Gynostemma pentaphyllum herbal tea on rat splenocyte proliferation. J Agric Food Chem 56:9305–9311

    Article  CAS  PubMed  Google Scholar 

  • Tang W, Eisenbrand G (2011) Handbook of Chinese medicinal plants: chemistry, pharmacology, toxicology, vol 1. Wiley-VCH, Weinheim

    Google Scholar 

  • Tsai YC, Lin CL, Chen BH (2010a) Preparative chromatography of flavonoids and saponins in Gynostemma pentaphyllum and their antiproliferation effect on hepatoma cell. Phytomedicine 18:2–10

    Article  CAS  PubMed  Google Scholar 

  • Tsai YC, Wu WB, Chen BH (2010b) Preparation of carotenoids and chlorophylls from Gynostemma pentaphyllum (Thunb.) Makino and their antiproliferation effect on hepatoma cell. J Med Food 13:1431–1442

    Article  CAS  PubMed  Google Scholar 

  • Tsui KC, Chiang TH, Wang JS, Lin LJ, Chao WC, Chen BH, Lu JF (2014) Flavonoids from Gynostemma pentaphyllum exhibit differential induction of cell cycle arrest in H460 and A549 cancer cells. Molecules 19:17663–17681

    Article  PubMed  Google Scholar 

  • Xie Z, Zhao Y, Chen P, Jing P, Yue J, Yu LL (2011) Chromatographic fingerprint analysis and rutin and quercetin compositions in the leaf and whole-plant samples of di- and tetraploid Gynostemma pentaphyllum. J Agric Food Chem 59:3042–3049

    Article  CAS  PubMed  Google Scholar 

  • Yan H, Wang X, Niu J, Wang Y, Wang P, Liu Q (2014) Anti-cancer effect and the underlying mechanisms of gypenosides on human colorectal cancer SW-480 cells. PLoS One 9:e95609

    Article  PubMed  PubMed Central  Google Scholar 

  • Yin F, Hu L, Pan R (2004) Novel dammarane-type glycosides from Gynostemma pentaphyllum. Chem Pharm Bull 52:1440–1444

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

This research was financially supported by the Ministry of Trade, Industry & Energy (MOTIE) and Korea Institute for Advancement of Technology (KIAT) through the Inter-ER Cooperation Projects (R0002021). The authors acknowledge the Korea Basic Science Institute for the NMR measurements.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Bang Yeon Hwang.

Ethics declarations

Conflict of interest

The authors have declared no conflict of interest.

Additional information

Hari Jang and Jin Woo Lee contributed equally to this work.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jang, H., Lee, J.W., Lee, C. et al. Flavonol glycosides from the aerial parts of Gynostemma pentaphyllum and their antioxidant activity. Arch. Pharm. Res. 39, 1232–1236 (2016). https://doi.org/10.1007/s12272-016-0793-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-016-0793-x

Keywords

Navigation