Skip to main content
Log in

Rhodiosin, an Antioxidant Flavonol Glycoside from Rhodiola rosea

  • Published:
Journal of the Korean Society for Applied Biological Chemistry Submit manuscript

Abstract

The EtOAc fraction of Rhodiola rosea ethanolic extracts showed a strong antioxidant activity. Through activity-guided fractionation and purification, we isolated two flavonol glycosides, which were identified as the well known flavonoids, rhodionin (1) and rhodiosin (2). To compare their antioxidant activities, we used an authentic aglycone compound, herbacetin (3). Among the compounds tested, rhodiosin (2) exhibited strong antioxidant activity, with IC50 values of 0.21 and 0.15 μM against •OH and •O- 2, respectively. Rhodiosin (2) (100 mg/kg) reduced MDA content in the liver induced by irradiation when given prior to exposure of γ-radiation.

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.

Similar content being viewed by others

Abbreviations

HPLC:

high pressure liquid chromatography

MDA:

malondialdehyde

NMR:

nuclear magnetic resornance

UWLA:

ultraweak chemiluminescence

References

  • Akgul Y, Ferreira D, Abourashed EA, and Khan IA (2004) Lotaustralin from Rhodiola rosea roots. Fitoterapia 75, 612–614.

    Article  CAS  Google Scholar 

  • Bass DA, Parce JW, Dechatelet LR, Szejda P, Seeds MC, and Thomas M (1983) Flow cytometric studies of oxidative product formation by neutrophils: A graded response to membrane stimulation. J Immunol 130, 1910–1917.

    CAS  Google Scholar 

  • Beuge JA and Aust SD (1978) Microsomal lipid peroxidation. Method Enzymol 12, 302–310.

    Article  Google Scholar 

  • Butterfield DA, Castenga A, Pocernich CB, Drake J, Scapagnini G, and Calabrese V (2002) Nutritional approaches to combat oxidative stress in Alzheimer’s disease. J Nurt Biochem 13, 444–461.

    Article  CAS  Google Scholar 

  • Cynamon HA, Isenberg JN, and Nguyen CH (1985) Erythrocyte malondialdehyde release in vitro: a functional measure of vitamin E status. Clin Chim Acta 151, 169–176.

    Article  CAS  Google Scholar 

  • Debashis DD, Bhattacharjee BM, and Banerjee RK (1997) Hydroxyl radicals is the major causative factor in stress-induced gastric ulceration. Free Radical Bio Med 23, 8–18.

    Article  Google Scholar 

  • Heo SJ, Park EJ, Lee KW, and Jeon YJ (2005) Antioxidant activities of enzymatic extracts from brown seaweeds. Bioresource Technol 96, 1613–1623.

    Article  CAS  Google Scholar 

  • Kergonou JF, Bernard P, Braquet M, and Rocquet G (1981) Effect of whole-body gamma irradiation on lipid peroxi-dation in rat tissues. Biochimie 63, 555–559.

    Article  CAS  Google Scholar 

  • Kurkin VA (2003) Phenylpropanoids from medicinal plants: distribution, classification, structural analysis and biological activity. Chem Nat Comp 39, 123–153.

    Article  CAS  Google Scholar 

  • Kurkin VA, Zapesochanaya GG, Gorbunov YN, Nukhimovskii EL, Shreter AI, and Shchavlinskii AN (1986) Chemical investigations on some species of Rhodiola L. and Sedum L. genera and problems of their chemotaxonomy. Rastitelney Resursy 22, 310–319.

    CAS  Google Scholar 

  • Kurkin VA, Zapesochanays GG, and Shchavlinskii AN (1984) Flavonoids of the rhizomes of Rhodiola rosea III. Chem Nat Comp 20, 367–368.

    Article  Google Scholar 

  • Lee MW, Lee YA, Park HM, Toh SH, Lee EJ, Jang HD, and Kim YH (2000) Antioxidative phenolic compounds from the roots of Rhoiola sachalinensis A. Bor. Arch Pharm Res 23, 455–458.

    Article  CAS  Google Scholar 

  • Ma G, Li W, Dou D, Chang X, Bai H, Satou T, Li J, Sun D, Kang T, Nikaido T, and Koike K (2006) Rhodiolosides A-E, monoterpene glycosides from Rhodiola rosea. Chem Pharm Bull 54, 1229–1233.

    Article  CAS  Google Scholar 

  • Markert M, Andrews PC, and Babior BM (1984) Measurement of O- 2 production by human neutrophils. The preparation and assay of NADPH oxidase-containing particles from human neutrophils. Method Enzymol 105, 358–365.

    Article  CAS  Google Scholar 

  • Ohkawa H, Ohishi N, and Yagi K (1979) Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 95, 351–358.

    Article  CAS  Google Scholar 

  • Ohsugi M, Fan W, and Hase K (1999) Active-oxygen scavenging activity of traditional nourishing-tonic herbal medicines and active constituents of Rhodiola sacra. J Ethnopharmacol 67, 111–119.

    Article  CAS  Google Scholar 

  • Petsalo A, Jalonen J, and Tolonen A (2006) Identification of flavonoids of Rhodiola rosea by liquid chromatography-tandem mass spectrometry. J Chromatogr A 1112, 224–231.

    Article  CAS  Google Scholar 

  • Rosenkranz AR, Schmaldienst S, Stuhlmeier KM, Chen W, Knapp W, and Zlabinger GJ (1992) A microplate assay for the detection of oxidative products using 2,7-dichlorofluorescin-diacetate. J Immunol Methods 156, 39–45.

    Article  CAS  Google Scholar 

  • Ryu KY, Kang, WS, and Lee MW (1998) Antioxidant effects of the rhizome Rhodiola sachalinensis. Yakhak Hoeji 42, 312–318.

    CAS  Google Scholar 

  • Sussman MS and Bulkley GB (1990) Oxygen derived free radicals in reperfusion. Method Enzymol 186, 711–723.

    Article  CAS  Google Scholar 

  • Tolonen A, Pakonen M, Hohtola A, and Jalonen J (2003) Phenylpropanoid glycosides from Rhodiola rosea. Chem Pharm Bull 51, 467–470.

    Article  CAS  Google Scholar 

  • Tsai, H, Chang C, and Chiou F (2001) Rapid and Specific detection of hydroxyl radical using an ultraweak chemiluminescence analyzer and low-level chemiluminescence emitter: application to hydroxyl radical-scavenging ability of aqueous extracts of food constituents. J Food Drug Anal 49, 2137–2141.

    CAS  Google Scholar 

  • Tsai H, Chang C, and Chiou F (2003) Improved superoxide-generating system suitable for the assessment of the superoxide-scavenging ability of aqueous extracts of food constituents using ultraweak chemiluminescence. J Food Drug Anal 51, 58–62.

    CAS  Google Scholar 

  • Vajragupta O, Boonchoong P, and Wongkrajang Y (2000) Comparative quantitative structure-activity study or radical scavengers. Bioorg Med Chem 8, 2617–2628.

    Article  CAS  Google Scholar 

  • Varshiney R and Kale RK (1990) Effects of calmodulin antagonists on radiation-induced lipid peroxidation in microsomes. Int J Radiat Biol 58, 733–743.

    Article  Google Scholar 

  • Yu WS, Chen XM, Li H, and Yang L (1993) Polyphenols from Rhodiola crenulara. Planta Med 59, 80–83.

    Article  CAS  Google Scholar 

  • Zapesochnaya GG and Kurkin VA (1983) The flavonoids of the rhizomes Rhoidiola rosea. Khim Prir Soedin 19, 23–32

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

These authors contributed equally.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kwon, HJ., Ryu, Y.B., Jeong, H.J. et al. Rhodiosin, an Antioxidant Flavonol Glycoside from Rhodiola rosea . J. Korean Soc. Appl. Biol. Chem. 52, 486–492 (2009). https://doi.org/10.3839/jksabc.2009.083

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.3839/jksabc.2009.083

Key words

Navigation