Skip to main content
SpringerLink
Log in

Isolation and identification of α-glucosidase inhibitors from the stem bark of the nutgall tree (Rhus javanica Linné)

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

Abstract

Ethyl acetate (EtOAc) layer obtained after the solvent fractionation of hot water extracts from nutgall tree (Rhus javanica) stem bark showed higher α-glucosidase inhibition activity than other layers. A novel acetophenone glucoside (4) and six known phenolic compounds were isolated from the EtOAc layer. The structure of 4 was determined to be 3,4,5-trihydroxyacetophenone 4-O-β-d-glucopyranoside. The six known compounds were identified as gallic acid (1), 5-methylresorcinol (2), methylgallate (3), 3-hydroxy-5-methylphenol 1-O-β-d-(6′-galloyl)glucopyranoside (5), scopoletin (6), and phlorizin (7). Their chemical structures were determined by electrospray ionization mass spectrometry and nuclear magnetic resonance analyses. Compound 5 was newly identified from this plant. Compounds 6 and 7 showed significantly higher α-glucosidase inhibition activity than other compounds.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Benalla W, Bellahcen S, and Bnouham M (2010) Antidiabetic medicinal plants as a source of alpha glucosidase inhibitors. Curr Diabetes Rev 6, 247–254.

    Article  CAS  Google Scholar 

  • Cho JY, Ji SH, Moon JH, Lee KH, Jung KH, and Park KH (2008) A novel benzoyl glucoside and phenolic compounds from the leaves of Camellia japonica. Food Sci Biotechnol 17, 1060–1065.

    CAS  Google Scholar 

  • Chun CS, Kim JH, Lim HA, Sohn HY, Son KH, Kim YK et al. (2004) Antioxidative effect of Rhus javanica Linne extract against hydrogen peroxide or menadione induced oxidative stress and DNA damage in HepG2 cells. J Food Sci Nutr 9, 150–155.

    Article  Google Scholar 

  • Chung SC, Hwang BY, Oh GJ, Kang SJ, Kim MJ, Choi WH et al. (1999) Chemical components from the stem bark of Rhus javanica L. Kor J Pharmacogn 30, 295–300.

    CAS  Google Scholar 

  • Goldstein BJ (2003) Insulin resistance: from benign to type 2 diabetes mellitus. Rev Cardiovasc Med 4,suppl 6, S3–S10.

    Google Scholar 

  • Gu Q, Wang RR, Zhang XM, Wang YH, Zheng YT, Zhou J et al. (2007) A new benzofuranone and anti-HIV constituents from the stems of Rhus chinensis. Plant Med 73, 279–282.

    Article  CAS  Google Scholar 

  • Hanefeld M, Schaper F, and Koehler C (2008) Effect of acarbose on vascular disease in patients with abnormal glucose tolerance. Cardiovasc Drugs Ther 22, 225–231.

    Article  CAS  Google Scholar 

  • Islam MN, Jung HA, Sohn HS, Kim HM, and Choi JS (2013) Potent α-glucosidase and protein tyrosine phosphatase 1B inhibitors from Artemisia capillaris. Arch Pharm Res 35, 542–552.

    Article  Google Scholar 

  • Iwakawa T, Tanaka Y, and Takashima A (2001) A new galloylglucoside from Cleyera ochnacea DC. Chem Pharm Bull 49, 1498–1499.

    Article  CAS  Google Scholar 

  • Karaca M, Magnan C, and Kargar C (2009) Functional pancreatic beta-cell mass: Involvement in type 2 diabetes and therapeutic intervention. Diabetes & Metabolism 35, 77–84.

    Article  CAS  Google Scholar 

  • Kim SH, Park HH, Lee SY, Jun CD, Choi BJ, Kim SY et al. (2005) The antianaphylactic effect of the gallo of Rhus javanica is mediated through inhibition of histamine release and inflammatory cytokine secretion. Int Immunopharmacol 5, 1820–1829.

    Article  CAS  Google Scholar 

  • Kumar S, Narwal S, Kumar V, and Prakash O (2011) α-Glucosidase inhibitors from plants: A natural approach to treat diabetes. Pharm Rev 5, 19–29.

    Article  CAS  Google Scholar 

  • Kurokawa M, Basnet P, Ohsugi M, Hozumi T, Kadota S, Namba T et al. (1999) Anti-herpes simplex virus activity of moronic acid purified from Rhus javanica in vitro and in vivo. J Pharm Exp Ther 289, 72–78.

    CAS  Google Scholar 

  • Kwon EJ, Kim YC, Kwon MS, Kim CS, Kang WW, Lee JB et al. (2001) Antioxidative activity of solvent fraction and isolation of antioxidant compound from chestnut husk. J Korean Soc Food Sci Nutr 30, 726–731.

    CAS  Google Scholar 

  • Lee IS, Oh SR, Ahn KS, and Lee HK. (2001) Semialactone, isofouquierone peroxide and fouquierone, three new dammarane triterpenes form Rhus javanica. Chem Pharm Bull 49, 1024–1026

    Article  CAS  Google Scholar 

  • Lee SK, Hwang JY, Song JH, Jo JR, Kim MJ, Kim ME et al. (2007) Inhibitory activity of Euonymus alatus against alpha-glucosidase in vitro and in vivo. Nutr Res Pract 1, 184–188.

    Article  Google Scholar 

  • Lin CN, Chen HL, and Yen MH (2008) Flavonoids with DNA strand-scission activity from Rhus javanica var. roxburghiana. Fitoterapia 79, 32–36.

    Article  CAS  Google Scholar 

  • Luo H, Imoto T, and Hiji Y (2001) Inhibitory effect of voglibose and gymnemic acid on maltose absorption in vivo. World J Gastroenterol 7, 270–274.

    CAS  Google Scholar 

  • Najafian M, Jahromi MZ, Nowroznejhad MJ, Khajeaian P, Kargar MM, Sadeghi M et al. (2012) Phloridzin reduces blood glucose levels and improves lipids metabolism in streptozotocin-induced diabetic rats. Mol Biol Rep 39, 5299–5306.

    Article  CAS  Google Scholar 

  • Oh JY, Choi U, Kim YS, and Shin DH (2003) Isolation and identification of antioxidative components from bark of Rhus javanica Linne. Korean J Food Sci Technol 35, 726–732.

    Google Scholar 

  • Reaven GM (1988) Role of insulin resistance in human disease. Diabetes 37, 1595–1607.

    Article  CAS  Google Scholar 

  • Rossetti L, Smith D, Shulman GI, Papachristou D, and DeFronzo RA (1987) Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats. J Clin Invest 79, 1510–1515.

    Article  CAS  Google Scholar 

  • Scheen AJ (2007) Antidiabetic agents in subjects with mild dysglycemia: prevent or early treatment of type 2 diabetes? Diabetes & Metabolism 33, 3–12.

    Article  CAS  Google Scholar 

  • Shim YJ, Doo HK, Ahn SY, Kim YS, Seong JK, Park IS et al. (2003) Inhibitory effect of aqueous extract from the gall of Rhus chinensis on alpha-glucosidase activity and postprandial blood glucose. J Ethnopharmacol 85, 35–37.

    Article  Google Scholar 

  • Standle E and Schnell O (2012) Alpha-glucosidase inhibitors 2012-Cardiovascular considerations and trial evaluation. Diab Vasc Dis Res 9, 163–169.

    Article  Google Scholar 

  • Wang RR, Gu Q, Wang YH, Zhang XM, Yang LM, Zhou J et al. (2008) Anti-HIV activities of compounds isolated from the medicinal plant Rhus chinensis. J Ethnopharmacol 117, 249–256.

    Article  CAS  Google Scholar 

  • Wansi JD, Lallemand MC, Chizem DD, Toze FAA, Mbaze LM, Naharkhan S et al. (2007) α-Glucosidase inhibitory constituents from stem bark of Terminalia superba (Combretaceae). Phytochemistry 68, 2096–2100.

    Article  CAS  Google Scholar 

  • Weihmeier UF and Piepersberg W (2004) Biotechnology and molecular biology of alpha-glucosidase inhibitor acarbose. Microbiol Biotechnol 63, 613–625.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Science & Biotechnology and Solar Salt Biotechnology Research Center, Mokpo National University, Muan, Jeonnam, 534-729, Republic of Korea

    Jeong-Yong Cho, Kang-Deok Lee, Sun-Young Park, Won Chul Jeong & Kyung-Sik Ham

  2. Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University, Gwangju, 500-757, Republic of Korea

    Jae-Hak Moon

Authors
  1. Jeong-Yong Cho
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kang-Deok Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sun-Young Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Won Chul Jeong
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jae-Hak Moon
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Kyung-Sik Ham
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kyung-Sik Ham.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cho, JY., Lee, KD., Park, SY. et al. Isolation and identification of α-glucosidase inhibitors from the stem bark of the nutgall tree (Rhus javanica Linné). J Korean Soc Appl Biol Chem 56, 547–552 (2013). https://doi.org/10.1007/s13765-013-3140-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13765-013-3140-7

Keywords

Search

Navigation