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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.)
Publication Information
Korean Journal of Medicinal Crop Science / v.12, no.5, 2004 , pp. 406-414 More about this Journal
Abstract
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.
Keywords
Rehmannia glutinosa L.; resveratrol synthase; $resveratrol-3-O-{\beta}-D-glucoside$;
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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 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   DOI   ScienceOn
3 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   DOI   ScienceOn
4 Goldberg DM (1995) 'Does wine work?' Clin. Chem. 41:14-16
5 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   DOI   PUBMED
6 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
7 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
8 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
9 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   DOI   ScienceOn
10 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   DOI   ScienceOn
11 Roggero JP, Archier P (1994) Quantitative determination of resveratrol and of one of its glycosides in wines. Sci. Aliments 14:99-107
12 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   DOI   ScienceOn
13 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   DOI   ScienceOn
14 Hostel W (1981) The Biochemistry of Plants, Vol. 7, 725-753, Academic Press, Inc., New York
15 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   DOI   ScienceOn
16 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   DOI   ScienceOn
17 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   DOI   ScienceOn
18 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
19 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   DOI   ScienceOn
20 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   DOI   ScienceOn
21 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   DOI   ScienceOn
22 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   DOI   ScienceOn
23 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   DOI   ScienceOn
24 Bertelli AAE (1998) Modulatory effect of resveratrol, a natural phytoalexin, on endothelial adhesion molecules and intracellular signal transduction. Pharmaceut. Biol. 36:44-52
25 Mock HP, Strack D (1993) Energetics ofuridine 5'-cliphosphoglucosehydroxy-cinnamic acid acyl-glucotransferase reaction. Phytochemistry 32:575-579   DOI   ScienceOn
26 Pflugmacher S, Sandennann H (1998) Taxonomic distribution of plant glucosyl- transferases acting on xenobiotics. Phytochemistry 49:507-511   DOI   ScienceOn
27 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   DOI   ScienceOn
28 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   DOI   ScienceOn
29 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   DOI   ScienceOn
30 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   DOI   ScienceOn
31 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   DOI   PUBMED   ScienceOn
32 Fremont L (2000) Biological effects of resveratrol. Life Sci. 66:663-673   DOI   PUBMED   ScienceOn
33 Siemann EH, Creasy LL (1992) Concentration of the phytoalexin resveratrol in wine. Am. J. Enol. Vitic 43:49-52
34 Sobolev VS, Cole RJ (1999) Trans-resveratrol content in commercial peanuts and peanut product. J. Agric. Food Chem. 47:14351439   DOI   ScienceOn
35 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   DOI   ScienceOn
36 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
37 Hanawa F, Tahara S, Mizutani I (1992) Antifungal stress Compounds from Veratrum grandifiorum leaves treated with cupric chloride. Phytochemistry 31:3005-3007   DOI   ScienceOn
38 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
39 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   DOI   ScienceOn
40 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   DOI   ScienceOn
41 Renauld S, De Lorgeril M (1992) Wine, alcohol, platelets, and the French paradox for coronary heart disease, Lancet, 339: 1523-1526   DOI   ScienceOn
42 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   DOI   ScienceOn
43 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
44 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   DOI   ScienceOn
45 Jeandet P, Bessis R, Sbaghi M, Meunier P (1994) Occurence of a resveratrol $\betaD-glucoside in wine; preliminary studies Vitis 33:183-184
46 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   DOI   ScienceOn