Chemical Composition and Active Antioxidants of Eucommia ulmoides Oliv. Bark

  • Qu, Guan-Zheng (School of Biotechnology, Kangwon National University) ;
  • Si, Chuan-Ling (Tianjin Key Laboratory of Pulp & Paper, Tianjin University of Science & Technology) ;
  • Yin, Yu (School of Biotechnology, Kangwon National University) ;
  • Wang, Myeong-Hyeon (School of Biotechnology, Kangwon National University)
  • Published : 2006.11.30

Abstract

Chemical composition of the Eucommia ulmoides bark, including extractives, proximate, mineral, fatty acid and monosaccharide compositions, was studied The most abundant mineral was calcium (533.17 mg/l00 g). $\alpha-linolenic$ acid (24.7%) and linoleic acid (24.3%), showed higher contents among the fatty acids. Major monosaccharides of E. ulmoides balk were arabinose (13.94 mg/g), xylose (18.91 mg/g) and glucose (119.7 mg/g). From the bark of E ulmoides, four compounds were isolated and their structures were elucidated as caffeic acid (I), kaempferol (II), quercetin (III) and isoquercitrin (IV) by spectroscopic analysis such as NMR and MS, including cellulose TLC and other chemical evidence such as hydrolyzation and acetylation. The antioxidant activities of four isolated compounds were evaluated by DPPH free radical scavenging, hydroxyl scavenging and reducing power assays. The results indicated that all the isolated compounds showed higher DPPH radical scavenging activity than $\alpha-tocopherol$ and BHT that were used as positive controls and these four compounds exhibited considerable reducing power and hydroxyl radical (OH) scavenging activity. Considering from the results above, it suggests that the E. ulmoides bark is a potential natural source of antioxidant material.

Keywords

References

  1. Halliwell B, Gutteridge JM. Free radicals in biology and medicine, Oxford University press, Oxford, 1999
  2. Chen FA, Wu AB, Shieh P, Kuo DH, Hsieh CY. Evaluation of the antioxidant activity of Ruellia tuberose. Food Chem 94:14-18, 2006 https://doi.org/10.1016/j.foodchem.2004.09.046
  3. Ames BN, Shigenaga MK, Hagen TM. Oxidants, antioxidants, and the degenerative diseases of aging. Proc Natl Acad Sci U.S.A. 90:7915-7922, 1993
  4. Ito N, Fukushima S, Hagiwara A, Shibata M, Ogiso T. Carcinogenicity of butylated hydroxyanisole in F344 rats. J Natl Cancer Inst 70:343-352, 1983
  5. Villano D, Fernandez-Pachon MS, Troncoso AM, GarciaParrida MC Influence of enological practices on the antioxidant activity of wines. Food Chem 95:394-404, 2006 https://doi.org/10.1016/j.foodchem.2005.01.005
  6. Duan XJ, Zhang WW, Li XP, Wang BG. Evaluation of antioxidant property of extract and fractions obtained from a red alga. Polysiphonia ukceolata Food Chem 95:37-43, 2006
  7. Nara K, Miyoshi T, Houma T, Koga H. Antioxidative activity of bond-form phenolics in potato red. Biosci Biotechnol Biochem 70:1489-1491, 2006
  8. Li ZL, Cui KM, Yuan ZD, Liu S. Regeneration of recovered bark in Eucommia ulmoides. Chem Biol Agric Med Earth Sci 26:33-40, 1983
  9. Kwan CY, Zhang WB, Deyarna T, Nishibe S. Endotheliumdependent vascular relaxation induced by Eucommia ulmoides Olivo bark extract is mediated by NO and EDHF in small vessels. Naunyn Schmiedebergs Arch Pharmacol 369:206-211, 2004 https://doi.org/10.1007/s00210-003-0822-4
  10. Lee MK, Kim MJ, Cho SY, Park SA, Park KK, Jung UJ, Park HM, Choi MS. Hypoglycemic effect of Du-zhong (Eucommia ulmoides Oliv.) leaves in streptozotocin-induced diabetic rats. Diabetes Res Clin Pract 67:22-28, 2005 https://doi.org/10.1016/j.diabres.2004.05.013
  11. AOAC. Official methods of analysis of AOAC international, 17th edn. Gaitherburg, MD, Association of Official Analytical Chemists (AOAC) International, USA, 2000
  12. Blakeney AB, Harris PJ, Henry RJ, Stone BA. A simple and rapid preparation of alditol acetates for monosaccharide analysis. Carbohydr Res 113:291-299, 1983 https://doi.org/10.1016/0008-6215(83)88244-5
  13. Yoshida T, Mori K, Hatano T, Okumura T, Uehara I, Komagoe K, Fujita Y, Okuda T. Study on inhibition mechanism of autooxidation by tannins and flavonoids. V. Radical scavenging effects of tannins and related polyphenols on 1,1-diphenyl-2-picrylhydrazyl radical. Chem Pharm Bull 37:1919-1921, 1989 https://doi.org/10.1248/cpb.37.1919
  14. Chung SK, Osawa T, Kawakishi S. Hydroxyl radical scavenging effects of spieces and scavenger from Brown Mustard (Brassica nigra). Biosci Biotechnol Biochem 61:118-123, 1997 https://doi.org/10.1271/bbb.61.118
  15. Ordonez AAL, Gomez JD, Vattuone MA, Isla MI. Antioxidant activities of Sechium edule (Jacq.) Swartz extracts. Food Chem 97:452-458, 2006 https://doi.org/10.1016/j.foodchem.2005.05.024
  16. Rural Nutrition Institute. Food composition table, 4th edn. Rural Development Administration. Korea, 1991
  17. Tomoda M, Gonda R, Shimizu N, Kanari M. A reticuloendothelial system-activating glycan from the barks of Eucommia ulmoides. Phytochemistry 29:3091-3094, 1990 https://doi.org/10.1016/0031-9422(90)80163-B
  18. Kelley DS, Branch LB, Love JE, Taylor PC, Rivera YM, Iacono JM. Dietary alpha-linolenic acid and immunocompetence in humans. Am J Clin Nutr 53:40-46, 1991 https://doi.org/10.1093/ajcn/53.1.40
  19. Cheminat A, Zawatzky R, Becker H, Brouillard R. Caffeoyl conjugates from Echinacea species: Structures and biological activity. Phytochemistry 27:2787-2794, 1988 https://doi.org/10.1016/0031-9422(88)80664-2
  20. Markham KR, Ternai B, Stanly R, Geiger H, Mabry TJ. Carbon-13 NMR studies of flavonoids-III: Naturally occurring flavonoid glycosides and their acetylated derivatives. Tetrahedron 34:1389-1397, 1978 https://doi.org/10.1016/0040-4020(78)88336-7
  21. Okuyama T, Hosoyama K, Hiragam Y, Kurono G, Takemoto T. The constituents of Osmunda spp: A new flavonol glycoside of Osmunda asiatica. Chem Pharm Bull 26:3071-3074, 1978 https://doi.org/10.1248/cpb.26.3071
  22. Ternai B, Markham KR. Carbon-13 NMR studies of flavonoids-I: flavones and flavonols. Tetrahedron 32:565-569, 1976 https://doi.org/10.1016/S0040-4020(01)93772-X
  23. Wenkert E, Gottlieb HE. Carbon-13 nuclear magnetic resonance spectroscopy of flavonoid and isoflavonoid compounds. Phytochemistry 16:1811-1816, 1977 https://doi.org/10.1016/0031-9422(71)85095-1
  24. Fernandez J, Reyes R, Ponce H, Oropeza M, Vancalstereri MR, Jankowski C, Campos MG. Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4incuced contraction in guinea-pig airways. Eur J Pharmacol 522:108-115, 2005 https://doi.org/10.1016/j.ejphar.2005.08.046
  25. Takeshi D, Sansei N, Yoshihisa N. Constituents and pharmacological effects of Eucommia and Siberian ginseng. Acta Pharmacol Sin 22:1057-1070, 2001
  26. Kim HY, Moon BH, Lee HJ, Choi DH. Flavonol glycosides from the leaves of Eucommia ulmoides O. with glycation inhibitory activity. J Ethnopharmacol 93:227-230, 2004 https://doi.org/10.1016/j.jep.2004.03.047
  27. Cho EJ, Yokozawa T, Rhyu DY, Kim SC, Shibahara N, Park JC. Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2picrylphdrazyl radical. Phytomedicine 10:544-551, 2003 https://doi.org/10.1078/094471103322331520
  28. Kumaran A, Karunakaran RJ. Activity-guided isolation and identification of free radical-scavenging components from an aqueous extract of Coleus aromaticus. Food Chem 100:356-361, 2007 https://doi.org/10.1016/j.foodchem.2005.09.051
  29. Jayaprakasha GK, Singh RP, Sakariah KK. Antioxidant activity of grape seed (Vitis vinifera) extracts on peroxidation models in vitro. Food Chem 73:285-290, 2001 https://doi.org/10.1016/S0308-8146(00)00298-3