Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 31, 2017 - Issue 5
589
Views
10
CrossRef citations to date
0
Altmetric
Review

In vitro assays in natural products research – a matter of concentration and relevance to in vivo administration using resveratrol, α-mangostin/γ-mangostin and xanthohumol as examples

&
Pages 492-506 | Received 14 Feb 2016, Accepted 01 May 2016, Published online: 27 May 2016

References

  • Almeida L, Vaz-da-Silva M, Falcão A, Soares E, Costa R, Loureiro AI, Fernandes-Lopes C, Rocha JF, Nunes T, Wright L, et al. 2009. Pharmacokinetic and safety profile of trans-resveratrol in a rising multiple-dose study in healthy volunteers. Mol Nutr Food Res. 53 (Suppl 1):S7–S15.10.1002/mnfr.v53.5s
  • Autenrieth CS, Baumert J, Baumeister SE, Fischer B, Peters A, Döring A, Thorand B. 2011. Association between domains of physical activity and all-cause, cardiovascular and cancer mortality. Eur J Epidemiol. 26:91–99.10.1007/s10654-010-9517-6
  • Balunas MJ, Su B, Brueggemeier RW, Kinghorn AD. 2008. Xanthones from the botanical dietary supplement mangosteen (Garcinia mangostana) with aromatase inhibitory activity. J Nat Prod. 71:1161–1166.10.1021/np8000255
  • Bellavia A, Larsson SC, Bottai M, Wolk A, Orsini N. 2013. Fruit and vegetable consumption and all-cause mortality: a dose-response analysis. Am J Clin Nutr. 98:454–459.10.3945/ajcn.112.056119
  • Bo S, Ciccone G, Castiglione A, Gambino R, De Michieli F, Villois P, Durazzo M, Cavallo-Perin P, Cassader M. 2013. Anti-inflammatory and antioxidant effects of resveratrol in healthy smokers a randomized, double-blind, placebo-controlled, cross-over trial. Curr Med Chem. 20:1323–1331.10.2174/0929867311320100009
  • Bolca S, Li J, Nikolic D, Roche N, Blondeel P, Possemiers S, De Keukeleire D, Bracke M, Heyerick A, van Breemen RB, et al. 2010. Disposition of hop prenylflavonoids in human breast tissue. Mol Nutr Food Res. Jul;54 (Suppl 2):S284–S294.10.1002/mnfr.v54.7s
  • Bollmann F, Art J, Henke J, Schrick K, Besche V, Bros M, Li H, Siuda D, Handler N., Bauer F, et al. 2014. Resveratrol post-transcriptionally regulates pro-inflammatory gene expression via regulation of KSRP RNA binding activity. Nucleic Acids Res. 42:12555–12569.10.1093/nar/gku1033
  • Boocock DJ, Faust GE, Patel KR, Schinas AM, Brown VA, Ducharme MP, Booth TD, Crowell JA, Perloff M, Gescher AJ, et al. 2007. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol Biomarkers Prev. 16:1246–1252.10.1158/1055-9965.EPI-07-0022
  • Brown VA, Patel KR, Viskaduraki M, Crowell JA, Perloff M, Booth TD, Vasilinin G, Sen A, Schinas AM, Piccirilli G, et al. 2010. Repeat dose study of the cancer chemopreventive agent resveratrol in healthy volunteers: safety, pharmacokinetics, and effect on the insulin-like growth factor axis. Cancer Res. 70:9003–9011.10.1158/0008-5472.CAN-10-2364
  • Bulun SE, Lin Z, Zhao H, Lu M, Amin S, Reierstad S, Chen D. 2009. Regulation of aromatase expression in breast cancer tissue. Ann N Y Acad Sci. 1155:121–131.10.1111/j.1749-6632.2009.03705.x
  • 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. 429:273–282.10.1042/BJ20091857
  • Chachay VS, Macdonald GA, Martin JH, Whitehead JP, O’Moore-Sullivan TM, Lee P, Franklin M, Klein K, Taylor PJ, Ferguson M, et al. 2014. Resveratrol does not benefit patients with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2092–2103:e2091–e2096.10.1016/j.cgh.2014.02.024
  • Chang J. 2000. Medicinal herbs: drugs or dietary supplements? Biochem Pharmacol. 59:211–219.10.1016/S0006-2952(99)00243-9
  • Chitchumroonchokchai C, Riedl KM, Suksumrarn S, Clinton SK, Kinghorn AD, Failla ML. 2012. Xanthones in mangosteen juice are absorbed and partially conjugated by healthy adults. J Nutr. 142 :675–680.10.3945/jn.111.156992
  • Choi YH, Han SY, Kim YJ, Kim YM, Chin YM. 2014. Absorption, tissue distribution, tissue metabolism and safety of α-mangostin in mangosteen extract using mouse models. Food Chem Toxicol. 66 :140–146.10.1016/j.fct.2014.01.028
  • Cristofoletti R, Dressman JB. 2014. Use of physiologically based pharmacokinetic models coupled with pharmacodynamic models to assess the clinical relevance of current bioequivalence criteria for generic drug products containing Ibuprofen. J Pharm Sci. 103:3263–3275.10.1002/jps.24076
  • Dildy T. 2015. Evidence for and against dietary recommendations to prevent cardiovascular disease. Tex Heart Inst J. 42:234–236.10.14503/THIJ-15-5072
  • Faghihzadeh F, Adibi P, Rafiei R, Hekmatdoost A. 2014. Resveratrol supplementation improves inflammatory biomarkers in patients with nonalcoholic fatty liver disease. Nutr Res. 34:837–843.10.1016/j.nutres.2014.09.005
  • Farzaneh V, Carvalho IS. 2015. A review of the health benefit potentials of herbal plant infusions and their mechanism of actions. Ind Crops Prod. 65:247–258.10.1016/j.indcrop.2014.10.057
  • Fernández-Mar MI, Mateos R, García-Parrilla MC, Puertas B, Cantos-Villar E. 2012. Bioactive compounds in wine: resveratrol, hydroxytyrosol and melatonin: a review. Food Chem. 130:797–813.10.1016/j.foodchem.2011.08.023
  • Garcea G, Berry DP, Jones DJ, Singh R, Dennison AR, Farmer PB, Sharma RA, Steward WP, Gescher AJ. 2005. Consumption of the putative chemopreventive agent curcumin by cancer patients: assessment of curcumin levels in the colorectum and their pharmacodynamic consequences. Cancer Epidemiol Biomarkers Prev. 14:120–125.
  • Goh KP, Lee HY, Lau DP, Supaat W, Chan YH, Koh AF. 2014. Effects of resveratrol in patients with type 2 diabetes mellitus on skeletal muscle SIRT1 expression and energy expenditure. Int J Sport Nutr Exerc Metab. 24:2–13.10.1123/ijsnem.2013-0045
  • Goldberg DM, Ng E, Yan J, Karumanchiri A, Soleas GJ, Diamandis EP. 1996. Regional differences in resveratrol isomer concentrations of wines from various cultivars. J Wine Res. 7:13–24.10.1080/09571269608718057
  • Goldberg DM, Yan J, Soleas GJ. 2003. Absorption of three wine-related polyphenols in three different matrices by healthy subjects. Clin Biochem. 36:79–87.10.1016/S0009-9120(02)00397-1
  • Gu X, Creasy L, Kester A, Zeece M. 1999. Capillary electrophoretic determination of resveratrol in wines. J Agric Food Chem. 47:3223–3227.10.1021/jf981211e
  • Gutierrez-Orozco F, Failla ML. 2013. Biological activities and bioavailability of mangosteen xanthones: a critical review of the current evidence. Nutrients. 5:3163–3183.10.3390/nu5083163
  • Hausenblas HA, Schoulda JA, Smoliga JM. 2015. Resveratrol treatment as an adjunct to pharmacological management in type 2 diabetes mellitus–systematic review and meta-analysis. Mol Nutr Food Res. 59:147–159.10.1002/mnfr.v59.1
  • Hoshino J, Park EJ, Kondratyuk TP, Marler L, Pezzuto JM, van Breemen RB, Mo S, Li Y, Cushman M. 2010. Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites. J Med Chem. 53:5033–5043.10.1021/jm100274c
  • Kalmar JM. 2005. The influence of caffeine on voluntary muscle activation. Med Sci Sports Exerc. 37:2113–2119.10.1249/01.mss.0000178219.18086.9e
  • Kondo M, Zhang L, Ji H, Kou Y, Ou B. 2009. Bioavailability and antioxidant effects of a xanthone-rich mangosteen (Garcinia mangostana) product in humans. J Agric Food Chem. 57:8788–8792.10.1021/jf901012f
  • Kopp P. 1998. Resveratrol, a phytoestrogen found in red wine. A possible explanation for the conundrum of the ‘French paradox’? Eur J Endocrinol. 138:619–620.10.1530/eje.0.1380619
  • Lambert JD, Lee MJ, Diamond L, Ju J, Hong J, Bose M, Newmark HL, Yang CS. 2006. Dose-dependent levels of epigallocatechin-3-gallate in human colon cancer cells and mouse plasma and tissues. Drug Metab Dispos. 34:8–11.
  • Legette L, Karnpracha C, Reed RL, Choi J, Bobe G, Christensen JM, Rodriguez-Proteau R, Purnell JQ, Stevens JF. 2014. Human pharmacokinetics of xanthohumol, an antihyperglycemic flavonoid from hops. Mol Nutr Food Res. 58:248–255.10.1002/mnfr.v58.2
  • Li S, Bouzar C, Cottet-Rousselle C, Zagotta I, Lamarche F, Wabitsch M, Tokarska-Schlattner M, Fischer-Posovszky P, Schlattner U, Rousseau D. 2016. Resveratrol inhibits lipogenesis of 3 T3-L1 and SGBS cells by inhibition of insulin signaling and mitochondrial mass increase. Biochim Biophys Acta. 1857:643–652.
  • Liang Y, Tian W, Ma X. 2013. Inhibitory effects of grape skin extract and resveratrol on fatty acid synthase. BMC Complement Altern Med. 13:361.10.1186/1472-6882-13-361
  • Lindstrom A, Ooyen C, Lynch ME, Blumenthal M, Kawa K. 2014. Sales of herbal dietary supplements increase by 7.9% in 2013, marking a decade of rising sales: turmeric supplements climb to top ranking in natural channel. Available from: http://cms.herbalgram.org/press/2014/2013_Herb_Market_Report.html?ts=1455394693&signature=5de88c798ce97e94358b796894af4e7f.
  • Lyles JT, Negrin A, Khan SI, He K, Kennelly EJ. 2014. In vitro antiplasmodial activity of benzophenones and xanthones from edible fruits of Garcinia species. Planta Med. 80:676–681.
  • Magyar K, Halmosi R, Palfi A, Feher G, Czopf L, Fulop A, Battyany I, Sumegi B, Toth K, Szabados E. 2012. Cardioprotection by resveratrol: a human clinical trial in patients with stable coronary artery disease. Clin Hemorheol Microcirc. 50:179–187.
  • Monteiro R, Becker H, Azevedo I, Calhau C. 2006. Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity. J Agric Food Chem. 54:2938–2943.10.1021/jf053162t
  • Monteiro R, Faria A, Azevedo I, Calhau C. 2007. Modulation of breast cancer cell survival by aromatase inhibiting hop (Humulus lupulus L.) flavonoids. J Steroid Biochem Mol Biol. 105:124–130.10.1016/j.jsbmb.2006.11.026
  • Nakagawa K, Miyazawa T. 1997. Absorption and distribution of tea catechin, (-)-epigallocatechin-3-gallate, in the rat. J Nutr Sci Vitaminol (Tokyo). 43:679–684.10.3177/jnsv.43.679
  • Ornstrup MJ, Harsløf T, Kjær TN, Langdahl BL, Pedersen SB. 2014. Resveratrol increases bone mineral density and bone alkaline phosphatase in obese men: a randomized placebo-controlled trial. J Clin Endocrinol Metab. 99:4720–4729.10.1210/jc.2014-2799
  • Patel KR, Brown VA, Jones DJ, Britton RG, Hemingway D, Miller AS, West KP, Booth TD, Perloff M, Crowell JA, et al. 2010. Clinical pharmacology of resveratrol and its metabolites in colorectal cancer patients. Cancer Res. 70:7392–7399.10.1158/0008-5472.CAN-10-2027
  • Péry AR, Brochot C, Zeman FA, Mombelli E, Desmots S, Pavan M, Fioravanzo E, Zaldívar JM2013. Prediction of dose-hepatotoxic response in humans based on toxicokinetic/toxicodynamic modeling with or without in vivo data: a case study with acetaminophen. Toxicol Lett. 220:26–34.10.1016/j.toxlet.2013.03.032
  • Petyaev IM, Bashmakov YK. 2012. Could cheese be the missing piece in the French paradox puzzle? Med Hypotheses. 79:746–749.10.1016/j.mehy.2012.08.018
  • Pirola L, Fröjdö S. 2008. Resveratrol: one molecule, many targets. IUBMB Life. 60:323–332.10.1002/(ISSN)1521-6551
  • Poulin P, Burczynski FJ, Haddad S. 2015. The role of extracellular binding proteins in the cellular uptake of drugs: impact on quantitative in vitro-to-in vivo extrapolations of toxicity and efficacy in physiologically based pharmacokinetic-pharmacodynamic research. J Pharm Sci. 105:497–508.
  • Poulsen MM, Vestergaard PF, Clasen BF, Radko Y, Christensen LP, Stodkilde-Jorgensen H, Moller N, Jessen N, Pedersen SB, Jorgensen JO. 2013. High-dose resveratrol supplementation in obese men: an investigator-initiated, randomized, placebo-controlled clinical trial of substrate metabolism, insulin sensitivity, and body composition. Diabetes. 62:1186–1195.10.2337/db12-0975
  • Rana J, Diwakar G, Saito L, Scholten JD, Mulder T. 2013. Inhibition of melanin content by Punicalagins in the super fruit pomegranate (Punica granatum). J Cosmet Sci. 64:445–453.
  • Rayalam S, Yang JY, Della-Fera MA, Park HJ, Ambati S, Baile CA. 2009. Anti-obesity effects of xanthohumol plus guggulsterone in 3T3-L1 adipocytes. J Med Food. 12:846–853.10.1089/jmf.2008.0158
  • Renaud S, de Lorgeril M. 1992. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet. 339:1523–1526.10.1016/0140-6736(92)91277-F
  • Rossi T, Gallo C, Bassani B, Canali S, Albini A, Bruno A. 2014. Drink your prevention: beverages with cancer preventive phytochemicals. Pol Arch Med Wewn. 124:713–722.
  • Sahebkar A. 2013. Effects of resveratrol supplementation on plasma lipids: a systematic review and meta-analysis of randomized controlled trials. Nutr Rev. 71:822–835.10.1111/nure.2013.71.issue-12
  • Sale S, Verschoyle RD, Boocock D, Jones DJ, Wilsher N, Ruparelia KC, Potter GA, Farmer PB, Steward WP, Gescher AJ. 2004. Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans 3,4,5,4’-tetramethoxystilbene. Br J Cancer. 90:736–744.10.1038/sj.bjc.6601568
  • Samitz G, Egger M, Zwahlen M. 2011. Domains of physical activity and all-cause mortality: systematic review and dose-response meta-analysis of cohort studies. Int J Epidemiol. 40:1382–1400.10.1093/ije/dyr112
  • Samsami-Kor M, Daryani NE, Asl PR, Hekmatdoost A. 2015. Anti-inflammatory effects of resveratrol in patients with ulcerative colitis: a randomized, double-blind, placebo-controlled pilot study. Arch Med Res. 46:280–285.
  • Savouret JF, Quesne M. 2002. Resveratrol and cancer: a review. Biomed Pharmacother. 56:84–87.10.1016/S0753-3322(01)00158-5
  • da Silva Santos V, de Almeida Teixeira GH, Barbosa F Jr. 2014. Acai (Euterpe oleracea Mart.): a tropical fruit with high levels of essential minerals-especially manganese-and its contribution as a source of natural mineral supplementation. J Toxicol Environ Health A. 77:80–89.10.1080/15287394.2014.866923
  • Stevens JF, Page JE. 2004. Xanthohumol and related prenylflavonoids from hops and beer: to your good health!. Phytochem. 65:1317–1330.10.1016/j.phytochem.2004.04.025
  • Stevens JF, Taylor AW, Deinzer ML. 1999. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J Chromatogr A. 832:97–107.10.1016/S0021-9673(98)01001-2
  • Tagawa N, Kubota S, Kato I, Kobayashi Y. 2013. Resveratrol inhibits 11beta-hydroxysteroid dehydrogenase type 1 activity in rat adipose microsomes. J Endocrinol. 218:311–320.10.1530/JOE-13-0066
  • Thazhath SS, Wu T, Bound MJ, Checklin HL, Standfield S, Jones KL, Horowitz M, Rayner CK. 2016. Administration of resveratrol for 5 wk has no effect on glucagon-like peptide 1 secretion, gastric emptying, or glycemic control in type 2 diabetes: a randomized controlled trial. Am J Clin Nutr. 103:66–70.10.3945/ajcn.115.117440
  • Timmers S, Konings E, Bilet L, Houtkooper RH, van de Weijer T, Goossens GH, Hoeks J, van der Krieken S, Ryu D, Kersten S, et al. 2011. Calorie restriction-like effects of 30 days of resveratrol supplementation on energy metabolism and metabolic profile in obese humans. Cell Metab. 14:612–622.10.1016/j.cmet.2011.10.002
  • van der Made SM, Plat J, Mensink RP. 2015. Resveratrol does not influence metabolic risk markers related to cardiovascular health in overweight and slightly obese subjects: a randomized, placebo-controlled crossover trial. PLOS ONE. 10:e0118393.10.1371/journal.pone.0118393
  • Vidavalur R, Otani H, Singal PK, Maulik N. 2006. Significance of wine and resveratrol in cardiovascular disease: French paradox revisited. Exp Clin Cardiol. 11:217–225.
  • 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. 49:495–504.10.1002/(ISSN)1613-4133
  • Vitrac X, Desmoulière A, Brouillaud B, Krisa S, Deffieux G, Barthe N, Rosenbaum J, Mérillon JM. 2003. Distribution of [14C]-trans-resveratrol, a cancer chemopreventive polyphenol, in mouse tissues after oral administration. Life Sci. 72:2219–2233.10.1016/S0024-3205(03)00096-1
  • 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. 32:1377–1382.10.1124/dmd.104.000885
  • Wang LX, Heredia A, Song H, Zhang Z, Yu B, Davis C, Redfield R. 2004. Resveratrol glucuronides as the metabolites of resveratrol in humans: Characterization, synthesis, and anti-HIV activity. J Pharm Sci. 93:2448–2457.10.1002/jps.20156
  • Wang Y, Lee KW, Chan FL, Chen S, Leung LK. 2006. The red wine polyphenol resveratrol displays bilevel inhibition on aromatase in breast cancer cells. Toxicol Sci. 92:71–77.10.1093/toxsci/kfj190
  • Wang X, Ouyang Y, Liu J, Zhu M, Zhao G, Bao W, Hu FB. 2014. Fruit and vegetable consumption and mortality from all causes, cardiovascular disease, and cancer: systematic review and dose-response meta-analysis of prospective cohort studies. BMJ. 349:g4490.10.1136/bmj.g4490
  • Warburton DE, Nicol CW, Bredin SS. 2006. Health benefits of physical activity: the evidence. CMAJ. 174:801–809.10.1503/cmaj.051351
  • Wollschlaeger B. 2003. The dietary supplement and health education act and supplements: dietary and nutritional supplements need no more regulations. Int J Toxicol. 22:387–390.10.1177/109158180302200509
  • Wong RH, Berry NM, Coates AM, Buckley JD, Bryan J, Kunz I, Howe PR. 2013. Chronic resveratrol consumption improves brachial flow-mediated dilatation in healthy obese adults. J Hypertens. 31:1819–1827.10.1097/HJH.0b013e328362b9d6
  • Xiang L, Xiao L, Wang Y, Li H, Huang Z, He X. 2014. Health benefits of wine: don’t expect resveratrol too much. Food Chem. 156:258–263.10.1016/j.foodchem.2014.01.006
  • Xie Z, Sintara M, Chang T, Ou B. 2015. Daily consumption of a mangosteen-based drink improves in vivo antioxidant and anti-inflammatory biomarkers in healthy adults: a randomized, double-blind, placebo-controlled clinical trial. Food Sci Nutr. 3:342–348.10.1002/fsn3.225
  • Yang JY, Della-Fera MA, Rayalam S, Baile CA. 2007. Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis. Apoptosis. 12:1953–1963.10.1007/s10495-007-0130-4
  • Yoon M, Campbell JL, Andersen ME, Clewell HJ. 2012. Quantitative in vitro to in vivo extrapolation of cell-based toxicity assay results. Crit Rev Toxicol. 42:633–652.10.3109/10408444.2012.692115
  • Yoshino J, Conte C, Fontana L, Mittendorfer B, Imai S, Schechtman KB, Gu C, Kunz I, Fanelli F, Patterson BW, et al. 2012. Resveratrol supplementation does not improve metabolic function in nonobese women with normal glucose tolerance. Cell Metab. 16:658–664.10.1016/j.cmet.2012.09.015
  • Zheng H, Yde CC, Clausen MR, Kristensen M, Lorenzen J, Astrup A, Bertram HC. 2015. Metabolomics investigation to shed light on cheese as a possible piece in the french paradox puzzle. J Agric Food Chem. 63:2830–2839.10.1021/jf505878a
  • Zortea K, Franco VC, Francesconi LP, Cereser KM, Lobato MI, Belmonte-de-Abreu PI. 2016. Resveratrol supplementation in schizophrenia patients: a randomized clinical trial evaluating serum glucose and cardiovascular risk factors. Nutrients. 8:73–82.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.