한국약용작물학회지 (Korean Journal of Medicinal Crop Science)

  • 제12권5호
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  • Pages.406-414
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  • 2004
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  • 1225-9306(pISSN)
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  • 2288-0186(eISSN)
한국약용작물학회 (The Korean Society of Medicinal Crop Science)
권호 표지

Isolation and Biological Activity of $Resveratrol-3-O-{\beta}-D-Glucoside$ in Transgenic Rehmannia glutinosa L. Transformed by Peanut Resveratrol Synthase Gene (RS3)

  • Lim, Jung-Dae (College of Agriculture & Life Sci., Kangwon Natl. Univ.) ;
  • Yang, Deok-Chun (College of Life Sci., Kyung Hee Univ.) ;
  • Yun, Song-Joong (Faculty of Biological Research Sci., Chonbuk Natl. Univ.) ;
  • Chung, Ill-Min (College of Life & Environment Sci., Konkuk Univ.) ;
  • Sung, Eun-Soo (Genome Research Center, KRIBB) ;
  • Kim, Myong-Jo (College of Agriculture & Life Sci., Kangwon Natl. Univ.) ;
  • Heo, Kweon (College of Agriculture & Life Sci., Kangwon Natl. Univ.) ;
  • Yu, Chang-Yeon (College of Agriculture & Life Sci., Kangwon Natl. Univ.)
  • 발행 : 2004.11.01
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초록

Resveratrol, which is both a phytoalexin with antifungal activity and a phytochemical associated with reduced cancer risk and reduced cardiovascular disease, is synthesized in a limited number of plant species including peanut. Resveratrol synthesis is catalyzed by the enzyme stilbene synthase including resveratrol synthase (RS). Resveratrol synthase gene (RS3) obtained from peanut, Arachis hypogaea, Fabaceae has been transferred into chinese foxglove, Rehmannia glutinosa by using Agrobacterium mediated transformation. RS t-DNA introduced to chinese foxglove (R. glutinosa L) by transformation and its reaction product, $resveratrol-3-O-{\beta}-D-glucoside$ was isolated and characterized using HPLC. Also its biological effects was tested in inhibition of the lipid peroxidation of mouse LDL by glycosylated stilbenes derivatives obtained from transgenic plants. $Resveratrol-3-O-{\beta}-D-glucoside$ isolated from transgenic R. glutinosa L. showed antimicrobial activity of the growth inhibition zone against Escherichia coli and Salmonella typhimurium. Therefore, this compound can be contributed to be useful as a phytoalexin for plant health as well as a phytochemical for human health.

키워드

참고문헌

  1. Adrian M, Jeandet P, Breuil ACe, Levite D, Deborg S, Bessis R (2000) Assay of resveratrol and derivative stilbenes in wine by direct injection high performance liquid chromatography. Am. J. Enol. Vitic., 51(1):37-41
  2. Belguendouz L, Fremont L, Linard A (1997) Resveratrol inhibits metal ion-dependent and independent peroxidation of porcine low-density lipoproteins. Biochem. Pharmacol. 53:1347-1355 https://doi.org/10.1016/S0006-2952(96)00820-9
  3. Bertelli AAE, Giovaninn L, De Caterina F, Miglioni M, Bernini W, Fregoni M, Bavaresco J, Trevisan M, Bertelli A (1995) Antiplatelet activity of synthetic and natural resveratrol in red wine. Int. J. Tiss. React., 17:1-3
  4. Bertelli AAE (1998) Modulatory effect of resveratrol, a natural phytoalexin, on endothelial adhesion molecules and intracellular signal transduction. Pharmaceut. Biol. 36:44-52
  5. Cadenas S, Barja G (1999) Resveratrol, melatonin, vitamin E, and PBN protect against renal oxidative DNA damage induced by the kidney carcinogen KBrO$_3$. Free Rad. Biol. Med. 26:1531-1537 https://doi.org/10.1016/S0891-5849(99)00019-2
  6. Carbo N, Costelli P, Baccino FM, Lopez-Soriano FJ, Argiles JM (1999) Resveratrol, a natural product present in wine, decreases tumour growth in a rat tumour model. Biochem. Biophys. Res. Commun. 254:739-743 https://doi.org/10.1006/bbrc.1998.9916
  7. Frankel EN, Waterhouse AL, Teissedre PL (1995) Principal phenolic phytochemicals in selected California wines and their antioxidant activity in inhibiting oxidation of human low density lipoproteins.J. Agr. Food Chem. 43:890-894 https://doi.org/10.1021/jf00052a008
  8. Fremont L (2000) Biological effects of resveratrol. Life Sci. 66:663-673 https://doi.org/10.1016/S0024-3205(99)00410-5
  9. Gehm BD, McAndrews JM, Chien PY, Jameson JL (1997) Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc. Natl Acad. Sci. USA 94:14138-14143 https://doi.org/10.1073/pnas.94.25.14138
  10. Gker H, Tuncbilek M, Ayhan G, Altanlar N (1998) Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity, Il. Farmaco, 53:415-420 https://doi.org/10.1016/S0014-827X(98)00045-7
  11. Goldberg DM (1995) 'Does wine work?' Clin. Chem. 41:14-16
  12. GonzaJez-Candelas L, Gil JV, Lamuela-Ravent6s RM, Ram6n D (2000) The use of transgenic yeast expressing a gene encoding a glycosyl-hydrolase as a tool to increase resveratrol content in wine, International J. of Food microbiology 59: 179-183 https://doi.org/10.1016/S0168-1605(00)00354-8
  13. Gu XL, Chub Qy, ODwyer M, Zeece M (2000) Analysis of resveratrol in wine by capillary electrophoresis. J Chromatogr. A 881(1-2):421-481
  14. Hain R, Bieseler B, Kindl H, Schrder G, Stocker R (1990) Expression of a stilbene synthase gene in Nicotiana tabacum results in synthesis of the phytoalexin resveratrol. Plant Mol Biol 15:325-335 https://doi.org/10.1007/BF00036918
  15. Hain R, Reif HJ, Krause E, Langebartels R, Kindl H, Vornam B, Wiese W, Schmelzer E, Schreier PH, Stker RH, Thornzik JE, Stenzel K (1993) Disease resistance results from foreign phytoalexin expression in a novel plant. Nature 361:153-156 https://doi.org/10.1038/361153a0
  16. Hale AJ, Smith CA, Sutherland LC, Stoneman YEA, Longthome VL, Culhane AC, Williams GT (1996) Apoptosis: Molecular regulation of cell death. Eur. J. Biochem. 236:1-26 https://doi.org/10.1111/j.1432-1033.1996.00001.x
  17. Hanawa F, Tahara S, Mizutani I (1992) Antifungal stress Compounds from Veratrum grandifiorum leaves treated with cupric chloride. Phytochemistry 31:3005-3007 https://doi.org/10.1016/0031-9422(92)83436-3
  18. Hasegawa T, Koike K, Takahashi S, Ariyoshi U (1982) Constituents of leaves and roots of Kailei Jio (Rehmammia glutinosa Libosch. Forma hueichingensis Hsiao). Shoyakugaku Zasshi. 36:1-5
  19. Hostel W (1981) The Biochemistry of Plants, Vol. 7, 725-753, Academic Press, Inc., New York
  20. Huang C, Ma WY, Goranson A, Dong Z (1999) Resveratrol suppresses cell transfo=ation and induces apoptosis through a p53-dependent pathway. Carcinogenesis 20:237-242 https://doi.org/10.1093/carcin/20.2.237
  21. Inamori Y, Ogawa M, Tsujibo H, Baba K, Kozawa M, Nakamura H (1991) The biological activities of podophyllotoxin compounds. Chem. Pharm. Bull. 39:805-807 https://doi.org/10.1248/cpb.39.805
  22. Jang M, Cal L, Udeani GO, Slowing KY, Thomas CF, Beecher CWW, Fong HHS, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC, PezzutoJM (1997) Cancer chemoprotective activity of resveratrol, a natural product derived from grapes. Science 275:218-220 https://doi.org/10.1126/science.275.5297.218
  23. Jeandet P, Bessis R, Sbaghi M, Meunier P (1994) Occurence of a resveratrol $\betaD-glucoside in wine; preliminary studies Vitis 33:183-184
  24. Jeandet P, Bessis R, Maume BF, Meunier P, Peyron D, Trollat P (1995) Effect of enological pratices on the resveratrol isomer content of wine. J. Agric. Food Chem. 41:521-523 https://doi.org/10.1021/jf00028a001
  25. Lim JD, Yun SJ, Lee SJ, Chung IM, Kim MJ, Heo K, Yu CY (2004a) Comparison of Resveratrol Contents in Medicinal Plants. Korean J. Medicinal Crop Sci. 12(2):163-170
  26. Lim JD, Yang DC, Yun SJ, Chung IM, Sung ES, Kim MJ, Heo K, Yu CY (2004b) Agrobacterium-mediated Transformation of Rehmannia glutinosa L. with Resveratrol Gene (RS3) of Peanut. Korean J. Medicinal Crop Sci. 12(2):171-178
  27. Kimura Y, Okuda H (2003) Effects of Naturally Occurring Stilbene Glucosides from Medicinal Plants and Wine, on Tumour Growth and Lung Metastasis in Lewis Lung CarcinomaBearing Mice. Journal of Pharmacy and Pharmacology, 52(10):1287-1296 https://doi.org/10.1211/0022357001777270
  28. Kitanaka S, Ikezawa T, Yasukawa K, Yamanouchi S, Takido M, Sung H, Kim I (1990) Alpha-viniferin, an anti-inflammatory compound from Caragana chamlagu root Chem. Pharm. Bull. 38:432-435 https://doi.org/10.1248/cpb.38.432
  29. Maccarrone M, Lorenzon T, Guerrieri P, Agro AF (1999) Resveratrol prevents apoptosis in K562 cells by inhibiting lipoxygenase and cyclooxygenase activity. Eur. J. Biochem. 265:27-34 https://doi.org/10.1046/j.1432-1327.1999.00630.x
  30. Mattivi F, Reniero F, Korhammer S (1995) Isolation, characterization and evolution in red wine vinification of resveratrol monomers. J. Agric. Food Chemistry 43:1820-1823 https://doi.org/10.1021/jf00055a013
  31. Melzoch K, Filip V, Buckiov D, Hanzlikova I, Smidrkal J (2000) Resveratrol occurrence in wine originating from Czech Vineyard regions and effect on human health. Czech J Food Sci. 18(1):35-40
  32. Mock HP, Strack D (1993) Energetics ofuridine 5'-cliphosphoglucosehydroxy-cinnamic acid acyl-glucotransferase reaction. Phytochemistry 32:575-579 https://doi.org/10.1016/S0031-9422(00)95139-2
  33. Murakami S, Arai I, Muramatsu M, Olomo S, Baba K, Kido T, Kozawa M (1992) Effect of stilbene derivatives on gastric H+,K+-ATPASE. Biochem. Pharmacol. 44(10):1947-1951 https://doi.org/10.1016/0006-2952(92)90096-2
  34. Norren KV, Borggreven JMPM, Hovingh A, Willems HL, Boo TD, Elving LD, Berden JHM, Pont JJHHMD (1997) Antioxidant activity the stilbene astringin, newly extracted from Vitis vinifera cell cultures. Clinical Chemistry 43(6): 1092-1093
  35. Pace-Asciak CR, Hahn S, Diamandis EP, Soleas G, Goldberg DM (1995) The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis; implications for protection against coronary heart disease. Clin. Chim. Acta. 235:207-219 https://doi.org/10.1016/0009-8981(95)06045-1
  36. Palomino O, G6mez-Serranillos MP, Slowing K, Carretero E, Villar A (2000) Study of polyphenols in grape berries by reversed-phase high-performance liquid chromatography. J. Chromo A. 870:449-451 https://doi.org/10.1016/S0021-9673(99)01225-X
  37. Pflugmacher S, Sandennann H (1998) Taxonomic distribution of plant glucosyl- transferases acting on xenobiotics. Phytochemistry 49:507-511 https://doi.org/10.1016/S0031-9422(98)00139-3
  38. Ray PS, Maulik G, Cordis GA, Bertelli AAE, Bertelli A, Das DK (1999) The red wine antioxidant resveratrol protects isolated rat hearts from ischemia reperfusion injury. Free Rad. Biol. Med. 27:160-169 https://doi.org/10.1016/S0891-5849(99)00063-5
  39. Renauld S, De Lorgeril M (1992) Wine, alcohol, platelets, and the French paradox for coronary heart disease, Lancet, 339: 1523-1526 https://doi.org/10.1016/0140-6736(92)91277-F
  40. Roggero JP, Archier P (1994) Quantitative determination of resveratrol and of one of its glycosides in wines. Sci. Aliments 14:99-107
  41. Romero-Prez AI, Lamuela-Ravents RM, Buxaderas R, de la Torre-Boronat MC (1996) Resveratrol and piceid as varietal markers of white wines.J. Agric. Food Chem. 44:1975-1978 https://doi.org/10.1021/jf960211g
  42. Siemann EH, Creasy LL (1992) Concentration of the phytoalexin resveratrol in wine. Am. J. Enol. Vitic 43:49-52
  43. Sobolev VS, Cole RJ (1999) Trans-resveratrol content in commercial peanuts and peanut product. J. Agric. Food Chem. 47:14351439 https://doi.org/10.1021/jf9809885
  44. Stark Lorenzen, Nelke B, Hanbler G, Muhlbach HP, Thornzik JE (1997) Transfer of a grapevine stilbene synthase gene to rice (Oryza sativa L.). Plant Cell Rep. 16:668-673 https://doi.org/10.1007/s002990050299
  45. Thornzik JE, Stenzel K, Stocker R, Schreier PH, Hairr R, Stahl DJ (1997) Synthesis of a grapevine phytoalexin in transgenic tomatoes (Lycopersicon esculentum Mill.) conditions resistance against Phytophthora infestations. Physiol. Mol. Plant Pathol. 51:265-278 https://doi.org/10.1006/pmpp.1997.0123
  46. Zhu Y, Coury LA, Long H, Duda CT, Kissinger CB, Kissinger PT (2000) Liquid chromatography with multichanel electrochemical detection for the determination of resveratrol in wine, grape juice, and grape seed capsulen with automated solid phase extraction.J. Liq. Chromo Rel. Technol. 23(10):1555-1564 https://doi.org/10.1081/JLC-100100434