Natural prenylated resveratrol analogs arachidin-1 and -3 demonstrate improved glucuronidation profiles and have affinity for cannabinoid receptors

References

• Abbott JA, Medina-Bolivar F, Martin EM, Engelberth AS, Villagarcia H, Clausen EC, Carrier DJ. (2010). Purification of resveratrol, arachidin-1, and arachidin-3 from hairy root cultures of peanut (Arachis hypogaea) and determination of their antioxidant activity and cytotoxicity. Biotechnol Prog 26:1344–1351.
   PubMedGoogle Scholar
• Asensi M, Medina I, Ortega A, Carretero J, Baño MC, Obrador E, Estrela JM. (2002). Inhibition of cancer growth by resveratrol is related to its low bioavailability. Free Radic Biol Med 33:387–398.
   PubMed Web of Science ®Google Scholar
• Baur JA, Sinclair DA. (2006). Therapeutic potential of resveratrol: the in vivo evidence. Nat Rev Drug Discov 5:493–506.
   PubMed Web of Science ®Google Scholar
• Bifulco M, Santoro A, Laezza C, Malfitano AM. (2009). Cannabinoid receptor CB1 antagonists state of the art and challenges. Vitam Horm 81:159–189.
   PubMedGoogle Scholar
• Bouaboula M, Perrachon S, Milligan L, Canat X, Rinaldi-Carmona M, Portier M, Barth F, Calandra B, Pecceu F, Lupker J, Maffrand JP, Le Fur G, Casellas P. (1997). A selective inverse agonist for central cannabinoid receptor inhibits mitogen-activated protein kinase activation stimulated by insulin or insulin-like growth factor 1. Evidence for a new model of receptor/ligand interactions. J Biol Chem 272:22330–22339.
   PubMed Web of Science ®Google Scholar
• Brill SS, Furimsky AM, Ho MN, Furniss MJ, Li Y, Green AG, Bradford WW, Green CE, Kapetanovic IM, Iyer LV. (2006). Glucuronidation of trans-resveratrol by human liver and intestinal microsomes and UGT isoforms. J Pharm Pharmacol 58:469–479.
   PubMed Web of Science ®Google Scholar
• Calamini B, Ratia K, Malkowski MG, Cuendet M, Pezzuto JM, Santarsiero BD, Mesecar AD. (2010). Pleiotropic mechanisms facilitated by resveratrol and its metabolites. Biochem J 429:273–282.
   PubMed Web of Science ®Google Scholar
• Chang JC, Lai YH, Djoko B, Wu PL, Liu CD, Liu YW, Chiou RY. (2006). Biosynthesis enhancement and antioxidant and anti-inflammatory activities of peanut (Arachis hypogaea L.) arachidin-1, arachidin-3, and isopentadienylresveratrol. J Agric Food Chem 54:10281–10287.
   PubMed Web of Science ®Google Scholar
• Cheng Y, Prusoff WH. (1973). Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 22:3099–3108.
   PubMed Web of Science ®Google Scholar
• Condori J, Medrano G, Sivakumar G, Nair V, Cramer C, Medina-Bolivar F. (2009). Functional characterization of a stilbene synthase gene using a transient expression system in planta. Plant Cell Rep 28:589–599.
   PubMedGoogle Scholar
• Condori J, Sivakumar G, Hubstenberger J, Dolan MC, Sobolev VS, Medina-Bolivar F. (2010). Induced biosynthesis of resveratrol and the prenylated stilbenoids arachidin-1 and arachidin-3 in hairy root cultures of peanut: Effects of culture medium and growth stage. Plant Physiol Biochem 48:310–318.
   PubMedGoogle Scholar
• Cottart CH, Nivet-Antoine V, Laguillier-Morizot C, Beaudeux JL. (2010). Resveratrol bioavailability and toxicity in humans. Mol Nutr Food Res 54:7–16.
   PubMed Web of Science ®Google Scholar
• Cucciolla V, Borriello A, Oliva A, Galletti P, Zappia V, Della Ragione F. (2007). Resveratrol: From basic science to the clinic. Cell Cycle 6:2495–2510.
   PubMed Web of Science ®Google Scholar
• De Santi C, Pietrabissa A, Spisni R, Mosca F, Pacifici GM. (2000). Sulphation of resveratrol, a natural compound present in wine, and its inhibition by natural flavonoids. Xenobiotica 30:857–866.
   PubMed Web of Science ®Google Scholar
• Deadwyler SA, Hampson RE, Bennett BA, Edwards TA, Mu J, Pacheco MA, Ward SJ, Childers SR. (1993). Cannabinoids modulate potassium current in cultured hippocampal neurons. Recept Channels 1:121–134.
   PubMedGoogle Scholar
• Diaz P, Xu J, Astruc-Diaz F, Pan HM, Brown DL, Naguib M. (2008). Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain. J Med Chem 51:4932–4947.
   PubMed Web of Science ®Google Scholar
• Djoko B, Chiou RY, Shee JJ, Liu YW. (2007). Characterization of immunological activities of peanut stilbenoids, arachidin-1, piceatannol, and resveratrol on lipopolysaccharide-induced inflammation of RAW 264.7 macrophages. J Agric Food Chem 55:2376–2383.
   PubMed Web of Science ®Google Scholar
• Doerge DR, Chang HC, Churchwell MI, Holder CL. (2000). Analysis of soy isoflavone conjugation in vitro and in human blood using liquid chromatography-mass spectrometry. Drug Metab Dispos 28:298–307.
   PubMed Web of Science ®Google Scholar
• Fraga CG. (2007). Plant polyphenols: How to translate their in vitro antioxidant actions to in vivo conditions. IUBMB Life 59:308–315.
   PubMed Web of Science ®Google Scholar
• Gutierrez T, Farthing JN, Zvonok AM, Makriyannis A, Hohmann AG. (2007). Activation of peripheral cannabinoid CB1 and CB2 receptors suppresses the maintenance of inflammatory nociception: A comparative analysis. Br J Pharmacol 150:153–163.
   PubMed Web of Science ®Google Scholar
• Hampson AJ, Grimaldi M, Axelrod J, Wink D. (1998). Cannabidiol and (-)Delta9-tetrahydrocannabinol are neuroprotective antioxidants. Proc Natl Acad Sci USA 95:8268–8273.
   PubMed Web of Science ®Google Scholar
• Han YS, Bastianetto S, Dumont Y, Quirion R. (2006). Specific plasma membrane binding sites for polyphenols, including resveratrol, in the rat brain. J Pharmacol Exp Ther 318:238–245.
   PubMed Web of Science ®Google Scholar
• Huang CP, Au LC, Chiou RY, Chung PC, Chen SY, Tang WC, Chang CL, Fang WH, Lin SB. (2010). Arachidin-1, a Peanut Stilbenoid, Induces Programmed Cell Death in Human Leukemia HL-60 Cells. J Agric Food Chem <Volume>:.
   Google Scholar
• Humphrey W, Dalke A, Schulten K. (1996). VMD: Visual molecular dynamics. J Mol Graph 14:33–8, 27.
   PubMedGoogle Scholar
• Joseph JA, Fisher DR, Cheng V, Rimando AM, Shukitt-Hale B. (2008). Cellular and behavioral effects of stilbene resveratrol analogues: Implications for reducing the deleterious effects of aging. J Agric Food Chem 56:10544–10551.
   PubMed Web of Science ®Google Scholar
• Kapetanovic IM, Muzzio M, Huang Z, Thompson TN, McCormick DL. (2010). Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats. Cancer Chemother Pharmacol <Volume>:.
   Web of Science ®Google Scholar
• Klein TW. (2005). Cannabinoid-based drugs as anti-inflammatory therapeutics. Nat Rev Immunol 5:400–411.
   PubMed Web of Science ®Google Scholar
• Kunos G, Osei-Hyiaman D, Bátkai S, Sharkey KA, Makriyannis A. (2009). Should peripheral CB(1) cannabinoid receptors be selectively targeted for therapeutic gain? Trends Pharmacol Sci 30:1–7.
   PubMed Web of Science ®Google Scholar
• Kurkela M, García-Horsman JA, Luukkanen L, Mörsky S, Taskinen J, Baumann M, Kostiainen R, Hirvonen J, Finel M. (2003). Expression and characterization of recombinant human UDP-glucuronosyltransferases (UGTs). UGT1A9 is more resistant to detergent inhibition than other UGTs and was purified as an active dimeric enzyme. J Biol Chem 278:3536–3544.
   PubMed Web of Science ®Google Scholar
• Kuuranne T, Kurkela M, Thevis M, Schänzer W, Finel M, Kostiainen R. (2003). Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. Drug Metab Dispos 31:1117–1124.
   PubMed Web of Science ®Google Scholar
• Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D, Pertwee R, Makriyannis A. (1999). Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J Med Chem 42:769–776.
   PubMedGoogle Scholar
• Lançon A, Hanet N, Jannin B, Delmas D, Heydel JM, Lizard G, Chagnon MC, Artur Y, Latruffe N. (2007). Resveratrol in human hepatoma HepG2 cells: Metabolism and inducibility of detoxifying enzymes. Drug Metab Dispos 35:699–703.
   PubMed Web of Science ®Google Scholar
• Lee HK, Choi EB, Pak CS. (2009). The current status and future perspectives of studies of cannabinoid receptor 1 antagonists as anti-obesity agents. Curr Top Med Chem 9:482–503.
   PubMed Web of Science ®Google Scholar
• Lekli I, Szabo G, Juhasz B, Das S, Das M, Varga E, Szendrei L, Gesztelyi R, Varadi J, Bak I, Das DK, Tosaki A. (2008). Protective mechanisms of resveratrol against ischemia-reperfusion-induced damage in hearts obtained from Zucker obese rats: The role of GLUT-4 and endothelin. Am J Physiol Heart Circ Physiol 294:H859–H866.
   PubMed Web of Science ®Google Scholar
• Li YY, Li YN, Ni JB, Chen CJ, Lv S, Chai SY, Wu RH, Yüce B, Storr M. (2010). Involvement of cannabinoid-1 and cannabinoid-2 receptors in septic ileus. Neurogastroenterol Motil 22:350–e88.
   PubMedGoogle Scholar
• Little JM, Kurkela M, Sonka J, Jäntti S, Ketola R, Bratton S, Finel M, Radominska-Pandya A. (2004). Glucuronidation of oxidized fatty acids and prostaglandins B1 and E2 by human hepatic and recombinant UDP-glucuronosyltransferases. J Lipid Res 45:1694–1703.
   PubMed Web of Science ®Google Scholar
• Mackie K, Hille B. (1992). Cannabinoids inhibit N-type calcium channels in neuroblastoma-glioma cells. Proc Natl Acad Sci USA 89:3825–3829.
   PubMed Web of Science ®Google Scholar
• Matsuda LA, Lolait SJ, Brownstein MJ, Young AC, Bonner TI. (1990). Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346:561–564.
   PubMed Web of Science ®Google Scholar
• Mechoulam R, Ben-Shabat S, Hanus L, Ligumsky M, Kaminski NE, Schatz AR, Gopher A, Almog S, Martin BR, Compton DR. (1995). Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol 50:83–90.
   PubMed Web of Science ®Google Scholar
• Medina-Bolivar F, Condori J, Rimando AM, Hubstenberger J, Shelton K, O’Keefe SF, Bennett S, Dolan MC. (2007). Production and secretion of resveratrol in hairy root cultures of peanut. Phytochemistry 68:1992–2003.
   PubMed Web of Science ®Google Scholar
• Medina-Bolivar F, Dolan M, Bennett S, Condori J, Hubstenberger J; 2010. Production of stilbenes in plant hairy root cultures. patent U.S. Patent 7,666,677.
   Google Scholar
• Miksits M, Maier-Salamon A, Vo TP, Sulyok M, Schuhmacher R, Szekeres T, Jäger W. (2010). Glucuronidation of piceatannol by human liver microsomes: Major role of UGT1A1, UGT1A8 and UGT1A10. J Pharm Pharmacol 62:47–54.
   PubMed Web of Science ®Google Scholar
• Munro S, Thomas KL, Abu-Shaar M. (1993). Molecular characterization of a peripheral receptor for cannabinoids. Nature 365:61–65.
   PubMed Web of Science ®Google Scholar
• Nie J, Lewis DL. (2001). Structural domains of the CB1 cannabinoid receptor that contribute to constitutive activity and G-protein sequestration. J Neurosci 21:8758–8764.
   PubMed Web of Science ®Google Scholar
• Pavón FJ, Serrano A, Pérez-Valero V, Jagerovic N, Hernández-Folgado L, Bermúdez-Silva FJ, Macías M, Goya P, de Fonseca FR. (2008). Central versus peripheral antagonism of cannabinoid CB1 receptor in obesity: Effects of LH-21, a peripherally acting neutral cannabinoid receptor antagonist, in Zucker rats. J Neuroendocrinol 20 Suppl 1:116–123.
   PubMed Web of Science ®Google Scholar
• Pertwee RG. (2005). Inverse agonism and neutral antagonism at cannabinoid CB1 receptors. Life Sci 76:1307–1324.
   PubMed Web of Science ®Google Scholar
• Pervaiz S, Holme AL. (2009). Resveratrol: Its biologic targets and functional activity. Antioxid Redox Signal 11:2851–2897.
   PubMed Web of Science ®Google Scholar
• Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE. (2004). UCSF Chimera–a visualization system for exploratory research and analysis. J Comput Chem 25:1605–1612.
   PubMed Web of Science ®Google Scholar
• Reggio PH. (2010). Endocannabinoid binding to the cannabinoid receptors: What is known and what remains unknown. Curr Med Chem 17:1468–1486.
   PubMed Web of Science ®Google Scholar
• Sabolovic N, Humbert AC, Radominska-Pandya A, Magdalou J. (2006). Resveratrol is efficiently glucuronidated by UDP-glucuronosyltransferases in the human gastrointestinal tract and in Caco-2 cells. Biopharm Drug Dispos 27:181–189.
   PubMed Web of Science ®Google Scholar
• Sali A, Blundell TL. (1993). Comparative protein modelling by satisfaction of spatial restraints. J Mol Biol 234:779–815.
   PubMed Web of Science ®Google Scholar
• Shen T, Wang XN, Lou HX. (2009). Natural stilbenes: An overview. Nat Prod Rep 26:916–935.
   PubMed Web of Science ®Google Scholar
• Shoemaker JL, Joseph BK, Ruckle MB, Mayeux PR, Prather PL. (2005). The endocannabinoid noladin ether acts as a full agonist at human CB2 cannabinoid receptors. J Pharmacol Exp Ther 314:868–875.
   PubMed Web of Science ®Google Scholar
• Sivakumar G, Medina-Bolivar F, Lay JO Jr, Dolan MC, Condori J, Grubbs SK, Wright SM, Baque MA, Lee EJ, Paek KY. (2011). Bioprocess and bioreactor: Next generation technology for production of potential plant-based antidiabetic and antioxidant molecules. Curr Med Chem 18:79–90.
   PubMed Web of Science ®Google Scholar
• Surh YJ, Kundu JK, Na HK, Lee JS. (2005). Redox-sensitive transcription factors as prime targets for chemoprevention with anti-inflammatory and antioxidative phytochemicals. J Nutr 135:2993S–3001S.
   PubMed Web of Science ®Google Scholar
• Vitaglione P, Sforza S, Galaverna G, Ghidini C, Caporaso N, Vescovi PP, Fogliano V, Marchelli R. (2005). Bioavailability of trans-resveratrol from red wine in humans. Mol Nutr Food Res 49:495–504.
   PubMed Web of Science ®Google Scholar
• Walle T, Hsieh F, DeLegge MH, Oatis JE Jr, Walle UK. (2004). High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos 32:1377–1382.
   PubMed Web of Science ®Google Scholar
• Wang YJ, He F, Li XL. (2003). [The neuroprotection of resveratrol in the experimental cerebral ischemia]. Zhonghua Yi Xue Za Zhi 83:534–536.
   PubMedGoogle Scholar
• Weiss JN. (1997). The Hill equation revisited: Uses and misuses. FASEB J 11:835–841.
   PubMed Web of Science ®Google Scholar
• Wenzel E, Somoza V. (2005). Metabolism and bioavailability of trans-resveratrol. Mol Nutr Food Res 49:472–481.
   PubMed Web of Science ®Google Scholar
• Wittwer E, Kern SE. (2006). Role of morphine’s metabolites in analgesia: Concepts and controversies. AAPS J 8:E348–E352.
   PubMed Web of Science ®Google Scholar
• Yazaki K, Sasaki K, Tsurumaru Y. (2009). Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry 70:1739–1745.
   PubMed Web of Science ®Google Scholar