Skip to main content
Log in

Synthesis and biological evaluation of flavonol-glucose conjugates for cosmeceutical development

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

Abstract

Quercetin and kaempferol, two well-known flavonols, were chemically conjugated with glucose to produce the corresponding flavonol glucosides, and the following biological activities were evaluated for cosmeceutical development: antioxidant activity, ability to increase collagen synthesis, and moisturizing activity. Among the synthetic flavonol glucosides, quercetin-3-O-β-D-glucoside significantly enhanced collagen synthesis (60 %) compared to quercetin. Kaempferol-3,7-di-O-β-D-glucoside showed promising skin-moisturizing effects, inducing a sixfold increase in the expression of aquaporin-3. Thus, both quercetin-3-O-β-D-glucoside and kaempferol-3,7-di-O-β-D-glucoside were shown to possess interesting biological activities which warrant their further development as cosmetic ingredients.

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
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Ardhaoui M, Falcimaigne A, Ognier S, Engasser JM, Moussou P, Pauly G, Ghoul M (2004) Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids. J Biotechnol 110:265–271

    Article  CAS  Google Scholar 

  • Boury-Jamot M, Sougrat R, Tailhardat M, Le Varlet B, Bonte F, Dumas M, Verbavatz JM (2006) Expression and function of aquaporins in human skin: is aquaporin-3 just a glycerol transporter? Biochim Biophys Acta 1758:1034–1042

    Article  CAS  Google Scholar 

  • Caldwell ST, Petersson HM, Farrugia LJ, Mullen W, Crozier A, Hartley RC (2006) Isotopic labelling of quercetin 3-glucoside. Tetrahedron 62:7257–7265

    Article  CAS  Google Scholar 

  • Chang Q, Zuo Z, Chow MSS, Ho WKK (2005) Difference in absorption of the two structurally similar flavonoid glycosides, hyperoside and isoquercitrin in rats. Eur J Pharm Biopharm 59:549–555

    Article  CAS  Google Scholar 

  • Chondrogianni N, Kapeta S, Chinou I, Vassilatou K, Papassideri I, Gonos ES (2010) Anti-ageing and rejuvenating effects of quercetin. Exp Gerontol 45:763–771

    Article  CAS  Google Scholar 

  • Chuarienthong P, Lourith N, Leelapornpisid P (2010) Clinical efficacy comparison of anti-wrinkle cosmetics containing herbal flavonoids. Int J Cosmet Sci 32:99–106

    Article  CAS  Google Scholar 

  • dal Belo SE, Gaspar LR, Maia Campos PM, Marty JP (2009) Skin penetration of epigallocatechin-3-gallate and quercetin from green tea and Ginkgo biloba extracts vehiculated in cosmetic formulations. Skin Pharmacol Physiol 22:299–304

    Article  CAS  Google Scholar 

  • Haapasaari K, Rossi O, Risteli J, Oikarinen A (1998) Effects of long-term inhaled corticosteroids on skin collagen synthesis and thickness in asthmatic patients. Eur Respir J 11:139–143

    Article  CAS  Google Scholar 

  • Hashimoto T, Ueda Y, Oi N, Sakakibara H, Piao C, Ashida H, Goto M, Kanazawa K (2006) Effects of combined administration of quercetin, rutin, and extract of white radish sprout rich in kaempferol glycosides on the metabolism in rats. Biosci Biotechnol Biochem 70:279–281

    Article  CAS  Google Scholar 

  • Kubo I, Nitoda T, Nihei K (2007) Effects of quercetin on mushroom tyrosinase and B16-F10 melanoma cells. Molecules 12:1045–1056

    Article  CAS  Google Scholar 

  • Lee EJ, Ji GE, Sung MK (2010) Quercetin and kaempferol suppress immunoglobulin E-mediated allergic inflammation in RBL-2H3 and Caco-2 cells. Inflamm Res 59:847–854

    Article  CAS  Google Scholar 

  • Li G, Zeng X, Xie Y, Cai Z, Moore JC, Yuan X, Cheng Z, Ji G (2012) Pharmacokinetic properties of isorhamnetin, kaempferol and quercetin after oral gavage of total flavones of Hippophae rhamnoides L. in rats using a UPLC-MS method. Fitoterapia 83:182–191

    Article  CAS  Google Scholar 

  • Murota K, Mitsukuni Y, Ichikawa M, Tsushida T, Miyamoto S, Terao J (2004) Quercetin-4′-glucoside is more potent than quercetin-3-glucoside in protection of rat intestinal mucosa homogenates against iron ion-induced lipid peroxidation. J Agric Food Chem 52:1907–1912

    Article  CAS  Google Scholar 

  • Nirmala P, Ramanathan M (2011) Effect of kaempferol on lipid peroxidation and antioxidant status in 1,2-dimethyl hydrazine induced colorectal carcinoma in rats. Eur J Pharmacol 654:75–79

    Article  CAS  Google Scholar 

  • Pang JL, Ricupero DA, Huang S, Fatma N, Singh DP, Romero JR, Chattopadhyay N (2006) Differential activity of kaempferol and quercetin in attenuating tumor necrosis factor receptor family signaling in bone cells. Biochem Pharmacol 71:818–826

    Article  CAS  Google Scholar 

  • Ranger CM, Singh AP, Johnson-Cicalese J, Polavarapu S, Vorsa N (2007) Intraspecific variation in aphid resistance and constitutive phenolics exhibited by the wild blueberry Vaccinium darrowi. J Chem Ecol 33:711–729

    Article  CAS  Google Scholar 

  • Vuorinen H, Maatta K, Torronen R (2000) Content of the flavonols myricetin, quercetin, and kaempferol in finnish berry wines. J Agric Food Chem 48:2675–2680

    Article  CAS  Google Scholar 

  • Walgren RA, Lin JT, Kinne RK, Walle T (2000) Cellular uptake of dietary flavonoid quercetin 4′-beta-glucoside by sodium-dependent glucose transporter SGLT1. J Pharmacol Exp Ther 294:837–843

    CAS  Google Scholar 

  • Zhang WL, Chen JP, Lam KY, Zhan JY, Yao P, Dong TT, Tsim KW (2014) Hydrolysis of glycosidic flavonoids during the preparation of danggui buxue tang: an outcome of moderate boiling of chinese herbal mixture. Evid Based Complement Alternat Med 2014:608721–608731

    Google Scholar 

Download references

Acknowledgments

This research was supported by Konkuk University in 2014.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Youhoon Chong.

Additional information

Kwang-Su Park, Hyungmi Kim, have 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

Park, KS., Kim, H., Kim, M.K. et al. Synthesis and biological evaluation of flavonol-glucose conjugates for cosmeceutical development. J Korean Soc Appl Biol Chem 58, 317–323 (2015). https://doi.org/10.1007/s13765-015-0049-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13765-015-0049-3

Keywords

Navigation