Oral bioavailability of curcumin: problems and advancements

References

• Alexander A, Qureshi A, Kumari L. Role of herbal bioactives as a potential bioavailability enhancer for active pharmaceutical ingredients. Fitoterapia 2014;97:1–14.
   PubMed Web of Science ®Google Scholar
• Aggarwal BB, Sundaram C, Malani N. Curcumin: the Indian solid gold [M]//The molecular targets and therapeutic uses of curcumin in health and disease. New York: Springer; 2007:1–75.
   Google Scholar
• Thiyagarajan M, Sharma SS. Neuroprotective effect of curcumin in middle cerebral artery occlusion induced focal cerebral ischemia in rats. Life Sci 2004;74:969–85.
   PubMed Web of Science ®Google Scholar
• Motterlini R, Foresti R, Bassi R. Curcumin, an antioxidant and anti-inflammatory agent, induces heme oxygenase-1 and protects endothelial cells against oxidative stress. Free Radic Biol Med 2000;28:1303–12.
   PubMed Web of Science ®Google Scholar
• Chen A, Xu J, Johnson AC. Curcumin inhibits human colon cancer cell growth by suppressing gene expression of epidermal growth factor receptor through reducing the activity of the transcription factor Egr-1. Oncogene 2006;25:278–87.
   PubMed Web of Science ®Google Scholar
• Bhattacharyya S, Mandal D, Sen GS, et al. Tumor-induced oxidative stress perturbs nuclear factor-kappaB activity-augmenting tumor necrosis factor-alpha-mediated T-cell death: protection by curcumin. Cancer Res 2007;67:362–70.
   PubMed Web of Science ®Google Scholar
• Barthelemy S, Vergnes L, Moynier M. Curcumin and curcumin derivatives inhibit Tat-mediated transactivation of type 1 human immunodeficiency virus long terminal repeat. Res Virol 1998;149:43–52.
   PubMedGoogle Scholar
• Aggarwal BB, Harikumar KB. Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. Int J Biochem Cell Biol 2009;41:40–59.
   PubMed Web of Science ®Google Scholar
• Ono K, Hasegawa K, Naiki H. Curcumin has potent anti-amyloidogenic effects for Alzheimer’s beta-amyloid fibrils in vitro. J Neurosci Res 2004;75:742–50.
   PubMed Web of Science ®Google Scholar
• Shishodia S, Sethi G, Aggarwal BB. Curcumin: getting back to the roots. Ann N Y Acad Sci 2005;1056:206–17.
   PubMed Web of Science ®Google Scholar
• Kunnumakkara AB, Anand P, Aggarwal BB. Curcumin inhibits proliferation, invasion, angiogenesis and metastasis of different cancers through interaction with multiple cell signaling proteins. Cancer Lett 2008;269:199–225.
   PubMed Web of Science ®Google Scholar
• Yang KY, Lin LC, Tseng TY. Oral bioavailability of curcumin in rat and the herbal analysis from Curcuma longa by LC-MS/MS. J Chromatogr B 2007;853:183–9.
   PubMed Web of Science ®Google Scholar
• Pan MH, Huang TM, Lin JK. Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab Dispos 1999;27:486–94.
   PubMed Web of Science ®Google Scholar
• Lao CD, Ruffin MT, Normolle D. Dose escalation of a curcuminoid formulation. BMC Complement Altern Med 2006;6:10.
   PubMedGoogle Scholar
• Cai X, Fang Z, Dou J. Bioavailability of quercetin: problems and promises. Curr Med Chem 2013;20:2572–82.
   PubMed Web of Science ®Google Scholar
• Zhang L, Zhu W, Yang C. A novel folate-modified self-microemulsifying drug delivery system of curcumin for colon targeting. Int J Nanomed 2012;7:151.
   PubMed Web of Science ®Google Scholar
• Tønnesen HH, Karlsen J. Studies on curcumin and curcuminoids. Zeitschrift für Lebensmittel-Untersuchung und Forschung 1985;180:402–4.
   PubMedGoogle Scholar
• Palanikumar L, Panneerselvam N. Curcumin: a putative chemopreventive agent. J Life Sci 2009;3:47–53.
   Google Scholar
• Hoehle SI, Pfeiffer E, Solyom AM, et al. Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver. J Agric Food Chem 2006;54:756–64.
   PubMed Web of Science ®Google Scholar
• Ireson C, Orr S, Jones DJL. Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Cancer Res 2001;61:1058–64.
   PubMed Web of Science ®Google Scholar
• Ireson CR, Jones DJL, Orr S. Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol Biomarkers Prev 2002;11:105–11.
   PubMed Web of Science ®Google Scholar
• Kurita T, Makino Y. Novel curcumin oral delivery systems. Anticancer Res 2013;33:2807–21.
   PubMed Web of Science ®Google Scholar
• Helson L. Curcumin (diferuloylmethane) delivery methods: a review. Biofactors 2013;39:21–6.
   PubMed Web of Science ®Google Scholar
• Citernesi U, Sciacchitano M. Phospholipid/active ingredient complexes. Cosmetics Toiletries 1995;110:57–68.
   Google Scholar
• Kidd PM. Phosphatidylcholine, a superior protectant against liver damage. Altern Med Rev 1996;1:258–74.
   Google Scholar
• Barzaghi N, Crema F, Gatti G. Pharmacokinetic studies on IdB 1016, a silybin-phosphatidylcholine complex, in healthy human subjects. Eur J Drug Metab Pharmacokinet 1990;15:333–8.
   PubMed Web of Science ®Google Scholar
• Buzzelli G, Moscarella S, Giusti A. A pilot study on the liver protective effect of silybin-phosphatidylcholine complex (IdB1016) in chronic active hepatitis. Int J Clin Pharmacol 1993;31:456–60.
   PubMed Web of Science ®Google Scholar
• Liu A, Lou H, Zhao L. Validated LC/MS/MS assay for curcumin and tetrahydrocurcumin in rat plasma and application to pharmacokinetic study of phospholipid complex of curcumin. J Pharm Biomed Anal 2006;40:720–7.
   PubMed Web of Science ®Google Scholar
• Maiti K, Mukherjee K, Gantait A, et al. Curcumin-phospholipid complex: preparation, therapeutic evaluation and pharmacokinetic study in rats. Int J Pharm 2007;330:155–63.
   PubMed Web of Science ®Google Scholar
• Gupta NK, Dixit VK. Bioavailability enhancement of curcumin by complexation with phosphatidyl choline. J Pharm Sci 2011;100:1987–95.
   PubMed Web of Science ®Google Scholar
• Lawrence MJ, Rees GD. Microemulsion-based media as novel drug delivery systems. Adv Drug Deliv Rev 2000;45:89–121.
   PubMed Web of Science ®Google Scholar
• Strey R. Microemulsion microstructure and interfacial curvature. Colloid Polym Sci 1994;272:1005–19.
   Web of Science ®Google Scholar
• Kesisoglou F, Panmai S, Wu Y. Application of nanoparticles in oral delivery of immediate release formulations. Curr Nanosci 2007;3:183–90.
   Web of Science ®Google Scholar
• Moulik SP, Paul BK. Structure, dynamics and transport properties of microemulsions. Adv Colloid Interface Sci 1998;78:99–195.
   Web of Science ®Google Scholar
• Yin YM, Cui FD, Mu CF. Docetaxel microemulsion for enhanced oral bioavailability: preparation and in vitro and in vivo evaluation. J Control Release 2009;140:86–94.
   PubMed Web of Science ®Google Scholar
• Neslihan GR, Benita S. Self-emulsifying drug delivery systems (SEDDS) for improved oral delivery of lipophilic drugs. Biomed Pharmacother 2004;58:173–82.
   PubMed Web of Science ®Google Scholar
• Wu X, Xu J, Huang X. Self-microemulsifying drug delivery system improves curcumin dissolution and bioavailability. Drug Dev Ind Pharm 2011;37:15–23.
   PubMed Web of Science ®Google Scholar
• Narang AS, Delmarre D, Gao D. Stable drug encapsulation in micelles and microemulsions. Int J Pharm 2007;345:9–25.
   PubMed Web of Science ®Google Scholar
• Ahmed K, Li Y, McClements DV, et al. Nanoemulsion- and emulsion-based delivery systems for curcumin: encapsulation and release properties. Food Chem 2012;132:799–807.
   Web of Science ®Google Scholar
• Wang X, Jiang Y, Wang YW. Enhancing anti-inflammation activity of curcumin through O/W nanoemulsions. Food Chem 2008;108:419–24.
   PubMed Web of Science ®Google Scholar
• Jang DJ, Kim ST, Oh E. Enhanced oral bioavailability and antiasthmatic efficacy of curcumin using redispersible dry emulsion. Biomed Mater Eng 2014;24:917–30.
   PubMed Web of Science ®Google Scholar
• Bergonzi MC, Hamdouch R, Mazzacuva F. Optimization, characterization and in vitro evaluation of curcumin microemulsions. LWT-Food Sci Technol 2014;59:148–55.
   Web of Science ®Google Scholar
• Cui J, Yu B, Zhao Y. Enhancement of oral absorption of curcumin by self-microemulsifying drug delivery systems. Int J Pharm 2009;371:148–55.
   PubMed Web of Science ®Google Scholar
• Setthacheewakul S, Mahattanadul S, Phadoongsombut N. Development and evaluation of self-microemulsifying liquid and pellet formulations of curcumin, and absorption studies in rats. Eur J Pharm Biopharm 2010;76:475–85.
   PubMed Web of Science ®Google Scholar
• Yu H, Huang Q. Improving the oral bioavailability of curcumin using novel organogel-based nanoemulsions. J Agric Food Chem 2012;60:5373–9.
   PubMed Web of Science ®Google Scholar
• Yu H, Shi K, Liu D. Development of a food-grade organogel with high bioaccessibility and loading of curcuminoids. Food Chem 2012;131:48–54.
   Web of Science ®Google Scholar
• Li L, Braiteh FS, Kurzrock R. Liposome-encapsulated curcumin: in vitro and in vivo effects on proliferation, apoptosis, signaling, and angiogenesis. Cancer 2005;104:1322–31.
   PubMed Web of Science ®Google Scholar
• Kreilgaard M. Influence of microemulsions on cutaneous drug delivery. Adv Drug Deliv Rev 2002;54:S77–98.
   PubMed Web of Science ®Google Scholar
• Chen H, Wu J, Sun M. N-trimethyl chitosan chloride-coated liposomes for the oral delivery of curcumin. J Liposome Res 2012;22:100–9.
   PubMed Web of Science ®Google Scholar
• Takahashi M, Uechi S, Takara K. Evaluation of an oral carrier system in rats: bioavailability and antioxidant properties of liposome-encapsulated curcumin. J Agric Food Chem 2009;57:9141–6.
   PubMed Web of Science ®Google Scholar
• Kakkar V, Singh S, Singla D. Exploring solid lipid nanoparticles to enhance the oral bioavailability of curcumin. Mol Nutr Food Res 2011;55:495–503.
   PubMed Web of Science ®Google Scholar
• Cuomo J, Appendino G, Dern AS. Comparative absorption of a standardized curcuminoid mixture and its lecithin formulation. J Nat Prod 2011;74:664–9.
   PubMed Web of Science ®Google Scholar
• Mohanty C, Das M, Sahoo SK. Emerging role of nanocarriers to increase the solubility and bioavailability of curcumin. Expert Opin Drug Deliv 2012;9:1347–64.
   PubMed Web of Science ®Google Scholar
• Hussain N, Jaitley V, Florence AT. Recent advances in the understanding of uptake of microparticulates across the gastrointestinal lymphatics. Adv Drug Deliv Rev 2001;50:107–42.
   PubMed Web of Science ®Google Scholar
• Yuan H, Chen J, Du YZ. Studies on oral absorption of stearic acid SLN by a novel fluorometric method. Colloids Surf B Biointerfaces 2007;58:157–64.
   PubMed Web of Science ®Google Scholar
• Lim SJ, Lee MK, Kim CK. Altered chemical and biological activities of all-trans retinoic acid incorporated in solid lipid nanoparticle powders. J Control Release 2004;100:53–61.
   PubMed Web of Science ®Google Scholar
• Lee WH, Loo CY, Young PM. Recent advances in curcumin nanoformulation for cancer therapy. Expert Opin Drug Deliv 2014;11:1183–201.
   PubMed Web of Science ®Google Scholar
• Allen TM. Liposomal drug formulations. Drugs 1998;56:747–56.
   PubMed Web of Science ®Google Scholar
• Yang C, Fu ZX. Liposomal delivery and polyethylene glycol-liposomal oxaliplatin for the treatment of colorectal cancer (Review). Biomed Rep 2014;2:335–9.
   PubMedGoogle Scholar
• Bégu S, Pouëssel AA, Lerner DA. Liposil, a promising composite material for drug storage and release. J Control Release 2007;118:1–6.
   PubMed Web of Science ®Google Scholar
• Li C, Zhang Y, Su T. Silica-coated flexible liposomes as a nanohybrid delivery system for enhanced oral bioavailability of curcumin. Int J Nanomed 2012;7:5995–6002.
   PubMed Web of Science ®Google Scholar
• Cabral H, Kataoka K. Progress of drug-loaded polymeric micelles into clinical studies. J Control Release 2014;190:465–76.
   PubMed Web of Science ®Google Scholar
• Lu Y, Park K. Polymeric micelles and alternative nanonized delivery vehicles for poorly soluble drugs. Int J Pharm 2013;453:198–214.
   PubMed Web of Science ®Google Scholar
• Reddy B, Yadav HKS, Nagesha DK. Polymeric micelles as novel carriers for poorly soluble drugs – a review. J Nanosci Nanotechnol 2015;15:4009–18.
   PubMed Web of Science ®Google Scholar
• Maitra A, Feldmann G, Bisht S. Water-dispersible oral, parenteral, and topical formulations for poorly water soluble drugs using smart polymeric nanoparticles: U.S. Patent 8,715,741[P]. 2014-5-6.
   Google Scholar
• Gaucher G, Satturwar P, Jones MC. Polymeric micelles for oral drug delivery. Eur J Pharm Biopharm 2010;76:147–58.
   PubMed Web of Science ®Google Scholar
• Letchford K, Liggins R, Burt H. Solubilization of hydrophobic drugs by methoxy poly (ethylene glycol)-block-polycaprolactone diblock copolymer micelles: theoretical and experimental data and correlations. J Pharm Sci 2008;97:1179–90.
   PubMed Web of Science ®Google Scholar
• Zhao L, Du J, Duan Y, et al. Curcumin loaded mixed micelles composed of pluronic P123 and F68: preparation, optimization and in vitro characterization. Colloids Surf B Biointerfaces 2012;97:101–8.
   PubMed Web of Science ®Google Scholar
• Ma Z, Shayeganpour A, Brocks DR, et al. High-performance liquid chromatography analysis of curcumin in rat plasma: application to pharmacokinetics of polymeric micellar formulation of curcumin. Biomed Chromatogr 2007;21:546–52.
   PubMed Web of Science ®Google Scholar
• Schiborr C, Kocher A, Behnam D. The oral bioavailability of curcumin from micronized powder and liquid micelles is significantly increased in healthy humans and differs between sexes. Mol Nutr Food Res 2014;58:516–27.
   PubMed Web of Science ®Google Scholar
• Cheng AL, Hsu CH, Lin JK, et al. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res 2001;21:2895–900.
   PubMed Web of Science ®Google Scholar
• Bala I, Bhardwaj V, Hariharan S. Sustained release nanoparticulate formulation containing antioxidant-ellagic acid as potential prophylaxis system for oral administration. J Drug Target 2006;14:27–34.
   PubMed Web of Science ®Google Scholar
• Ji H, Tang J, Li M. Curcumin-loaded solid lipid nanoparticles with Brij78 and TPGS improved in vivo oral bioavailability and in situ intestinal absorption of curcumin. Drug Deliv 2016;23:459–70.
   PubMed Web of Science ®Google Scholar
• Ramalingam P, Ko YT. Enhanced oral delivery of curcumin from N-trimethyl chitosan surface-modified solid lipid nanoparticles: pharmacokinetic and brain distribution evaluations. Pharm Res 2015;32:389–402.
   PubMed Web of Science ®Google Scholar
• Shaikh J, Ankola DD, Beniwal V. Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur J Pharm Sci 2009;37:223–30.
   PubMed Web of Science ®Google Scholar
• Xie X, Tao Q, Zou Y. PLGA nanoparticles improve the oral bioavailability of curcumin in rats: characterizations and mechanisms. J Agric Food Chem 2011;59:9280–9.
   PubMed Web of Science ®Google Scholar
• Bansal T, Mishra G, Jaggi M. Effect of P-glycoprotein inhibitor, verapamil, on oral bioavailability and pharmacokinetics of irinotecan in rats. Eur J Pharm Sci 2009;36:580–90.
   PubMed Web of Science ®Google Scholar
• Holder GM, Plummer JL, Ryan AJ. The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat. Xenobiotica 1978;8:761–8.
   PubMed Web of Science ®Google Scholar
• Shoba G, Joy D, Joseph T. Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Med 1998;64:353–6.
   PubMed Web of Science ®Google Scholar
• Anand P, Kunnumakkara AB, Newman RA. Bioavailability of curcumin: problems and promises. Mol Pharm 2007;4:807–18.
   PubMed Web of Science ®Google Scholar
• Grill AE, Koniar B, Panyam J. Co-delivery of natural metabolic inhibitors in a self-microemulsifying drug delivery system for improved oral bioavailability of curcumin. Drug Deliv Trans Res 2014;4:344–52.
   PubMed Web of Science ®Google Scholar
• Salem M, Rohani S, Gillies ER. Curcumin, a promising anti-cancer therapeutic: a review of its chemical properties, bioactivity and approaches to cancer cell delivery. RSC Adv 2014;4:10815–29.
   Web of Science ®Google Scholar