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Determination of flavonoids in Acer okamotoanum and their aldose reductase inhibitory activities

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Abstract

Plants in the genus Acer include medicinal plants and deciduous tree species in which several bioactive compounds have been isolated. In this study, flavonoids were isolated from the aerial parts of Acer okamotoanum by open column chromatography and identified by spectroscopic analysis as afzelin, quercitrin, and isoquercitrin. Among these flavonoids, quercitrin and isoquercitrin exhibited potent aldose reductase inhibitory activity (IC50 value of 0.40 and 0.63 μM, respectively). Almost all studied tissues of Acer spp. contained high amounts of quercitrin. The leaf of A. mono had the highest amount of quercitrin (61.90 μg g−1). Our results demonstrated that Acer species contain high concentrations of flavonoids with promising aldose reductase inhibitory activity that could be utilized to develop novel therapeutics for diabetic disorders.

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References

  • Abou-zaid MM, Nozzolillo C, Tonon A, Coppens M, Lombardo DA (2008) High-performance liquid chromatography characterization and identification of antioxidant polyphenols in maple syrup. Pharm Biol 46:117–125

    Article  CAS  Google Scholar 

  • Amado NG, Cerqueira DM, Menezes FS, da Silva JF, Neto VM, Abreu JG (2009) Isoquercitrin isolated from Hyptis fasciculate reduces glioblastoma cell proliferation and changes beta-catenin cellular localization. Anticancer Drug 20:543–552

    Article  CAS  Google Scholar 

  • Apati P, Szentmihályi K, Balázs A, Baumann D, Hamburger M, Kristó TS, Szőke E, Kéry A (2002) HPLC Analysis of the flavonoids in pharmaceutical preparations from Canadian goldenrod (Solidago canadensis). Chromatographia 56:65–68

    Article  Google Scholar 

  • Bhandari SR, Bashyal U, Lee Y-S (2016) Variations in proximate nutrients, phytochemicals, and antioxidant activity of field-cultivated red pepper fruits at different harvest times. Hort Environ Biotechnol 57:493–503

    Article  CAS  Google Scholar 

  • Bolingon AA, Feltrin AC, Machado MM, Javonik V, Athayde ML (2009) HPLC analysis and phytoconstituents isolated from ethyl acetate fraction of Scutia buxifolia Reiss. leaves. Lat Am J Pharm 28:121–124

    Google Scholar 

  • Chang SW, Kim KH, Lee IK, Choi SU, Ryu SY, Lee KR (2009) Phytochemical constituents of Bistoria manshuriensis. Nat Prod Sci 15:234–240

    CAS  Google Scholar 

  • Choi SY, Lee J, Lee DG, Lee S, Cho EJ (2017) Acer okamotoanum improves cognition and memory function in Ab25–35-induced Alzheimer’s mice model. Appl Biol Chem 60:1–9

    Article  Google Scholar 

  • Constantino L, Rastelli G, Vianello P, Cignarella G, Barlocco D (1999) Diabetes complications and their potential prevention: aldose reductase inhibition and other approaches. Med Res Rev 19:3–23

    Article  Google Scholar 

  • De la fuente JA, Manzanaro S (2003) Aldose reductase inhibitors from natural sources. Nat Prod Rep 20:243–251

    Article  CAS  PubMed  Google Scholar 

  • Drel VR, Pacher P, Ali TK, Shin J, Julius U, El-Remessy AB, Obrosova IG (2008) Aldose reductase inhibitor fidarestat counteracts diabetes-associated cataract formation, retinal oxidative-nitrosative stress, glial activation, and apoptosis. Int J Mol Med 21:667–676

    CAS  PubMed  PubMed Central  Google Scholar 

  • Gasparotto Junior A, Gasparotto FM, Lourenço EL, Crestani S, Stefanello ME, Salvador MJ, da Silva-Santos JE, Marques MC, Kassuya CA (2011) Antihypertensive effects of isoquercitrin and extracts from Tropaeolum majus L.: evidence for the inhibition of angiotensin converting enzyme. J Ethnopharmacol 134:363–372

    Article  CAS  PubMed  Google Scholar 

  • Hasan MS, Ahmed MI, Mondal S, Uddin SJ, Masud MM, Sadhu SK, Ishibashi M (2006) Antioxidant, antinociceptive activity and general toxicity study of Dendrophthoe falcata and isolation of quercitrin as the major component. Orient Pharm Exp Med 6:355–360

    Article  Google Scholar 

  • Hong CO, Lee HA, Rhee CH, Choung SY, Lee KW (2013) Seperation of the antioxidant compound quercitrin from Lindera obtusiloba blume and its antimelanogenic effect on B16F10 melanoma cells. Biosci Biotechnol Biochem 77:58–64

    Article  CAS  PubMed  Google Scholar 

  • Hotta N, Akanuma Y, Kawamori R, Matsuoka K, Oka Y, Shichiri M, Toyata T, Nakashima M, Yoshimura I, Sakamoto N, Shigeta Y (2006) Long-term clinical effects of epalrestat, an aldose reductase inhibition, on diabetic peripheral neuropathy. Diabetes Care 29:1538–1544

    Article  CAS  PubMed  Google Scholar 

  • Jin WY, Min BS, Youn UJ, Hung TM, Song KS, Seong YH, Bae KH (2006) Chemical constituents from the leaf and twig of Acer okamotoanum Nakai and their cytotoxicity. Kor J Med Crop Sci 14:77–81

    Google Scholar 

  • Jin WY, Min BS, Lee JP, Thuong PT, Lee HK, Song KS, Seong YH, Bae KH (2007) Isolation of constituents and anti-complement activity from Acer okamotoanum. Arch Pharm Res 30:172–176

    Article  CAS  PubMed  Google Scholar 

  • Jung HA, Kim YS, Choi JS (2009) Quantitative HPLC analysis of two key flavonoids and inhibitory activities against aldose reductase from different parts of the Korean thistle, Cirsium maackii. Food Chem Toxicol 47:2790–2797

    Article  CAS  PubMed  Google Scholar 

  • Kim HJ, Woo ER, Shin CG, Park H (1998) A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase. J Nat Prod 61:145–148

    Article  CAS  PubMed  Google Scholar 

  • Kim JK, Lee YS, Kim SH, Bae YS, Lim SS (2011) Inhibition of aldose reductase by phenylethanoid glycoside isolated from the seeds of Paulownia coreana. Biol Pharm Bull 34:160–163

    Article  CAS  PubMed  Google Scholar 

  • Kim HM, Lee DG, Lee S (2015) Plant-derived molecules from Saussurea grandifolia as inhibitors of aldose reductase. J Korean Soc Appl Biol Chem 58:365–371

    Article  CAS  Google Scholar 

  • Lee TB (1982) Illustrated flora of Korea. Hyangmunsa. pp. 522-524

  • Lee SY, So YJ, Shin MS, Cho JY, Lee J (2014) Antibacterial effects of afzelin isolated from Cornus macrophylla on Pseudomonas aeruginosa, a leading cause of illness in Immunocompromised indivisuals. Molecules 19:3173–3180

    Article  PubMed  Google Scholar 

  • Li J, Wang ZW, Zhang L, Liu X, Chen XH, Bi KS (2008) HPLC analysis and pharmacokinetic study of quercitrin and isoquercitrin in rat plasma after administration of Hypericum japonicum Thunb. extract. Biomed Chromatogr 22:374–378

    Article  CAS  PubMed  Google Scholar 

  • Matsumoto T, Ono Y, Kurono M, Kuromiya A, Nakamura K, Bril V (2008) Ranirestat (AS-3201), a potent aldose reductase inhibitor, reduces sorbitol levels and improves motor nerve conduction velocity in streptozotocin-diabetic rats. J Pharmacol Sci 107:231–237

    Article  CAS  PubMed  Google Scholar 

  • Miyazaki K, Ishizawa S, Nagumo S, Inoue T, Nagai M (1991) Studies on the constituents of Aceraceae plants. IX. Constituents of Acer cissifolium. Yakugaku Zasshi 45:333–335

    CAS  Google Scholar 

  • Mok SY, Lee S (2013) Identification of flavonoids and flavonoid rhamnosides from Rhododendron mucronulatum for. Albiflorum and their inhibitory activities against aldose reductase. Food Chem 136:969–974

    Article  CAS  PubMed  Google Scholar 

  • Mok SY, Shin HC, Lee S (2012) Screening of aldose reductase inhibitory activity of white-color natural products. CNU J Agric Sci 39:69–73

    Article  CAS  Google Scholar 

  • Moon HS, Kwon SD (2004) Sap collection and major components of Acer okamotoanum Nakai in Ullungdo. Kor J Med Crop Sci 12:249–254

    Google Scholar 

  • Ohta Y, Torii H, Okada H, Hattori H, Majima Y, Ishiguro I (1996) Involvement of oxidative stress in d-xylose-induced cataractogenesis in cultured rat lenses. Curr Eye Res 15:1–7

    Article  CAS  PubMed  Google Scholar 

  • Okuda J, Miwa I, Inagaki K, Horie T, Nakayama M (1984) Inhibition of aldose reductase by 3′, 4′-dihydroxyflavones. Chem Pharm Bull 32:767–772

    Article  CAS  PubMed  Google Scholar 

  • Oliveira TTD, Nagem TJ, Miranda LCGD, Paula VFD, Texeira MA (1997) Inhibitory action on aldose reductase by soybean flavonoids. Soc Bras Química 8:211–213

    Google Scholar 

  • Park JC, Kim SH (1995) Seasonal variation of flavonoid contents in the leaves of Cedrela sinensis. J Korean Soc Food Nutr 24:578–581

    CAS  Google Scholar 

  • Park EK, Ahn SR, Kim DH, Lee EW, Kwon HJ, Kim BW, Kim TH (2014) Effects of unripe apple polyphenols on the expression of matrix metalloproteinase-1 and type-1 procollagen in ultraviolet irradiated human skin fibroblasts. J Korean Soc Appl Biol Chem 57:449–455

    Article  CAS  Google Scholar 

  • Park S-A, Lee A-Y, Lee G-J, Kim D-S, Kim WS, Shoemaker CA, Son K-C (2016) Horticultural activity interventions and outcomes: a review. Korean Soc Hort Sci 34:513–527

    Google Scholar 

  • Reddy GB, Muthenna P, Akileshwari C, Saraswat M, Petrash JM (2011) Inhibition of aldose reductase and sorbitol accumulation by dietary rutin. Curr Sci 101:1191–1197

    CAS  Google Scholar 

  • Sato S, Kador PF (1990) Inhibition of aldehyde reductase by aldose reductase. Biochem Pharmacol 40:1033–1042

    Article  CAS  PubMed  Google Scholar 

  • Sun W, Oates PJ, Coutcher JB, Gerhardinger C, Lorenzi M (2006) A selective aldose reductase inhibitor of a new structural class prevents or reverses early retinal abnormalities in experimental diabetic retinopathy. Diabetes 55:2757–2762

    Article  CAS  PubMed  Google Scholar 

  • Takayama K, Sun BY, Stuessy TF (2013) Anagentic speciation in Ullung island, Korea: genetic diversity and structure in the island endemic species, Acer takesimense (Sapindaceae). J Plant Res 126:323–333

    Article  PubMed  Google Scholar 

  • Varma SD, Mikuni I, Kinoshita JH (1975) Flavonoids as inhibitors of lens aldose reductase. Science 188:1215–1216

    Article  CAS  PubMed  Google Scholar 

  • Wen YJ, Thuong PT, Su ND, Min BS, Son KH, Chang HW, Kim HP, Kang SS, Sok DE, Bae KH (2007) Antioxidant activity of cleomiscosins A and C isolated from Acer okamotoanum. Arch Pharm Res 30:275–281

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the Chung-Ang University Research Grants in 2017 and Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2015R1D1A1A01058868).

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Correspondence to Sanghyun Lee.

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Lee, J., Lee, DG., Rodriguez, J.P. et al. Determination of flavonoids in Acer okamotoanum and their aldose reductase inhibitory activities. Hortic. Environ. Biotechnol. 59, 131–137 (2018). https://doi.org/10.1007/s13580-018-0014-2

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  • DOI: https://doi.org/10.1007/s13580-018-0014-2

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