Curcumin Summary with useful bibliography
Curcumin Summary with useful bibliography
Curcumin has been used as an edible health-promoting substance for thousands of years as part of traditional medicinal practices in Asia. More recently, modern scientific methods have demonstrated that curcumin exhibits a broad spectrum of biological activities that may be beneficial to human health, including antioxidant, antimicrobial, anti-inflammatory, and antitumor activities. Even so, there are a number of challenges that have to be addressed when formulating curcumin-based functional foods or therapeutics, including its low water solubility, chemical stability, and bioavailability.
In this article, we highlighted some of the methods that can be used to overcome these problems, including antioxidant, encapsulation, and storage strategies. In particular, we focused on the utilization of colloidal delivery systems, such as micelles, liposomes, microemulsions, emulsions, solid lipid nanoparticles, biopolymer particles, and nature-derived colloidal particles. Each of these delivery systems has its own advantages and disadvantages for specific applications and it is important to select the most appropriate formulation. For instance, there are differences in the appearances, textures, mouthfeels, flavors, shelf-lives, and environmental histories of different curcumin-fortified functional food products (such as soft drinks, milky drinks, sauces, dressings, and bakery goods), which require different kinds of encapsulation technologies. In the future, it will be important to compare different formulations in terms of their cost, ease of manufacture, robustness, pharmacokinetics, bioavailability, bioactivity, sustainability, and environmental impact. The most suitable formulation for a specific application can then be selected.
Funding: This material was partly based upon work supported by the National Institute of Food and Agriculture, USDA, Massachusetts Agricultural Experiment Station (Project Number 831) and USDA, AFRI Grants (2016-08782).
Acknowledgments: This material was partly based upon work supported by the National Institute of Food and
Agriculture, USDA, Massachusetts Agricultural Experiment Station (Project Number 831).
Conflicts of Interest: The authors declare no conflict of interest.
Abbreviations
C4-2B C4-2 Bone metastatic
- coli Escherichia coli
- faecalis Enterococcus faecalis
HCT 116 Human Colorectal Carcinoma cell lines
IL Interleukin
LNCaP Lymph Node Carcinoma of the Prostate
NFkB Nuclear Factor Kappa B
- P. aeruginosa Pseudomonas aeruginosa Rko Rectal carcinoma cell line autrus Staphylococcus aureus
TNF-a Tumor Necrosis Factor Alpha
References
- Sharma, R.; Gescher, A.; Steward, W. Curcumin: The story so far. Eur. J. Cancer 2005, 41, 1955–1968. [CrossRef] [PubMed]
- Shahidi, F.; Naczk, M. Phenolics in Food and Nutraceuticals; CRC Press: Boca Raton, FL, USA, 2003.
- Heger, M.; van Golen, R.F.; Broekgaarden, M.; Michel, M.C. The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer. Pharmacol. Rev. 2014, 66, 222–307. [CrossRef] [PubMed]
- Priyadarsini, K.I. The chemistry of curcumin: From extraction to therapeutic agent. Molecules 2014, 19, 20091–20112. [CrossRef] [PubMed]
- Jurenka, J.S. Anti-inflammatory properties of curcumin, a major constituent of curcuma longa: A review of preclinical and clinical research. Altern. Med. Rev. 2009, 14, 141–153. [PubMed]
- Menon, V.P.; Sudheer, A.R. Antioxidant and anti-inflammatory properties of curcumin. In The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease; Springer: New York, NY, USA, 2007; pp. 105–125.
- Ak, T.; Gülçin, I˙. Antioxidant and radical scavenging properties of curcumin. Chem. Biol. Interact. 2008, 174, 27–37. [CrossRef] [PubMed]
- Zorofchian Moghadamtousi, S.; Abdul Kadir, H.; Hassandarvish, P.; Tajik, H.; Abubakar, S.; Zandi, K. A review on antibacterial, antiviral, and antifungal activity of curcumin. BioMed Res. Int. 2014, 2014, 1–12. [CrossRef] [PubMed]
- Martins, C.; Da Silva, D.; Neres, A.; Magalhaes, T.; Watanabe, G.; Modolo, L.; Sabino, A.; De Fátima, A.; De Resende, M. Curcumin as a promising antifungal of clinical interest. J. Antimicrob. Chemother. 2008, 63, 337–339. [CrossRef]
- Bar-Sela, G.; Epelbaum, R.; Schaffer, M. Curcumin as an anti-cancer agent: Review of the gap between basic and clinical applications. Curr. Med. Chem. 2010, 17, 190–197. [CrossRef]
- Naksuriya, O.; Okonogi, S.; Schiffelers, R.M.; Hennink, W.E. Curcumin nanoformulations: A review of pharmaceutical properties and preclinical studies and clinical data related to cancer treatment. Biomaterials 2014, 35, 3365–3383. [CrossRef]
- Anand, P.; Kunnumakkara, A.B.; Newman, R.A.; Aggarwal, B.B. Bioavailability of curcumin: Problems and promises. Mol. Pharm. 2007, 4, 807–818. [CrossRef]
- Tønnesen, H.H.; Másson, M.; Loftsson, T. Studies of curcumin and curcuminoids. Xxvii. Cyclodextrin complexation: Solubility, chemical and photochemical stability. Int. J. Pharm. 2002, 244, 127–135.
- Kharat, M.; Du, Z.; Zhang, G.; McClements, D.J. Physical and chemical stability of curcumin in aqueous solutions and emulsions: Impact of ph, temperature, and molecular environment. J. Agric. Food Chem. 2017, 65, 1525–1532. [CrossRef]
- McClements, D.J.; Decker, E.A.; Park, Y.; Weiss, J. Structural design principles for delivery of bioactive components in nutraceuticals and functional foods. Crit. Rev. Food Sci. Nutr. 2009, 49, 577–606. CrossRef]
- Garti, N. Delivery and Controlled Release of Bioactives in Foods and Nutraceuticals; Elsevier: Amsterdam, The Netherlands, 2008.
- Zhang, Z.; Zhang, R.; Decker, E.A.; McClements, D.J. Development of food-grade filled hydrogels for oral delivery of lipophilic active ingredients: Ph-triggered release. Food Hydrocoll. 2015, 44, 345–352. [CrossRef]
- McClements, D.; Decker, E.; Weiss, J. Emulsion-based delivery systems for lipophilic bioactive components.Food Sci. 2007, 72, R109–R124. [CrossRef] [PubMed]
- Lee, W.-H.; Loo, C.-Y.; Bebawy, M.; Luk, F.; Mason, R.S.; Rohanizadeh, R. Curcumin and its derivatives: Their application in neuropharmacology and neuroscience in the 21st century. Curr. Neuropharmacol. 2013, 11, 338–378. [CrossRef] [PubMed]
- Bhatia, N.K.; Kishor, S.; Katyal, N.; Gogoi, P.; Narang, P.; Deep, S. Effect of ph and temperature on conformational equilibria and aggregation behaviour of curcumin in aqueous binary mixtures of ethanol. RSC Adv. 2016, 6, 103275–103288. [CrossRef]
- Manolova, Y.; Deneva, V.; Antonov, L.; Drakalska, E.; Momekova, D.; Lambov, N. The effect of the water on the curcumin tautomerism: A quantitative approach. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2014, 132, 815–820. [CrossRef] [PubMed]
- Murugan, P.; Pari, L. Influence of tetrahydrocurcumin on hepatic and renal functional markers and protein levels in experimental type 2 diabetic rats. Basic Clin. Pharmacol. Toxicol. 2007, 101, 241–245. [CrossRef]
- Willcox, J.K.; Ash, S.L.; Catignani, G.L. Antioxidants and prevention of chronic disease. Crit. Rev. Food Sci. Nutr. 2004, 44, 275–295. [CrossRef] [PubMed]
- Barclay, L.R.C.; Vinqvist, M.R.; Mukai, K.; Goto, H.; Hashimoto, Y.; Tokunaga, A.; Uno, H. On the antioxidant mechanism of curcumin: Classical methods are needed to determine antioxidant mechanism and activity. Org. Lett. 2000, 2, 2841–2843. [CrossRef] [PubMed]
- Jayaprakasha, G.; Rao, L.J.; Sakariah, K. Antioxidant activities of curcumin, demethoxycurcumin and bisdemethoxycurcumin. Food Chem. 2006, 98, 720–724. [CrossRef]
- Goel, A.; Kunnumakkara, A.B.; Aggarwal, B.B. Curcumin as “curecumin”: From kitchen to clinic. Biochem. Pharmacol. 2008, 75, 787–809. [CrossRef] [PubMed]
- Arun, N.; Nalini, N. Efficacy of turmeric on blood sugar and polyol pathway in diabetic albino rats. Plant Foods Hum. Nutr. 2002, 57, 41–52. [CrossRef] [PubMed]
- Chandran, B.; Goel, A. A randomized, pilot study to assess the efficacy and safety of curcumin in patients with active rheumatoid arthritis. Phytother. Res. 2012, 26, 1719–1725. [CrossRef]
- Anna, K.T.; Suhana, M.; Das, S.; Faizah, O.; Hamzaini, A. Anti-inflammatory effect of curcuma longa (turmeric) on collagen-induced arthritis: An anatomico-radiological study. Clin. Ter. 2011, 162, 201–207.
- Yang, Q.Q.; Farha, A.K.; Kim, G.; Gul, K.; Gan, R.Y.; Corke, H. Antimicrobial and anticancer applications and related mechanisms of curcumin-mediated photodynamic treatments. Trends Food Sci. Technol. 2020, 97, 341–354. [CrossRef]
- Gupta, S.C.; Sung, B.; Kim, J.H.; Prasad, S.; Li, S.Y.; Aggarwal, B.B. Multitargeting by turmeric, the golden spice: From kitchen to clinic. Mol. Nutr. Food Res. 2013, 57, 1510–1528. [CrossRef]
- Vaughn, A.R.; Haas, K.N.; Burney, W.; Andersen, E.; Clark, A.K.; Crawford, R.; Sivamani, R.K. Potential role of curcumin against biofilm-producing organisms on the skin: A review. Phytother. Res. 2017, 31, 1807–1816. [CrossRef]
- Tyagi, P.; Singh, M.; Kumari, H.; Kumari, A.; Mukhopadhyay, K. Bactericidal activity of curcumin i is associated with damaging of bacterial membrane. PLoS ONE 2015, 10, e0121313. [CrossRef]
- Tomeh, M.A.; Hadianamrei, R.; Zhao, X. A review of curcumin and its derivatives as anticancer agents. Int. J. Mol. Sci. 2019, 20, 1033. [CrossRef] [PubMed]
- Arbiser, J.L.; Klauber, N.; Rohan, R.; van Leeuwen, R.; Huang, M.-T.; Fisher, C.; Flynn, E.; Byers, H.R. Curcumin is an in vivo inhibitor of angiogenesis. Mol. Med. 1998, 4, 376–383. [CrossRef] [PubMed]
- Teiten, M.-H.; Gaascht, F.; Eifes, S.; Dicato, M.; Diederich, M. Chemopreventive potential of curcumin in prostate cancer. Genes Nutr. 2010, 5, 61. [CrossRef] [PubMed]
- Dorai, T.; Dutcher, J.P.; Dempster, D.W.; Wiernik, P.H. Therapeutic potential of curcumin in prostate cancer—IV: Interference with the osteomimetic properties of hormone refractory c4-2b prostate cancer cells. Prostate 2004, 60, 1–17. [CrossRef]
- Liu, Q.; Loo, W.T.; Sze, S.; Tong, Y. Curcumin inhibits cell proliferation of mda-mb-231 and bt-483 breast cancer cells mediated by down-regulation of nfκb, cyclind and mmp-1 transcription. Phytomedicine 2009, 16, 916–922. [CrossRef]
- Mudduluru, G.; George-William, J.N.; Muppala, S.; Asangani, I.A.; Kumarswamy, R.; Nelson, L.D.; Allgayer, H. Curcumin regulates mir-21 expression and inhibits invasion and metastasis in colorectal cancer. Biosci. Rep. 2011, 31, 185–197. [CrossRef]
- Kunnumakkara, A.B.; Bordoloi, D.; Harsha, C.; Banik, K.; Gupta, S.C.; Aggarwal, B.B. Curcumin mediates anticancer effects by modulating multiple cell signaling pathways. Clin. Sci. 2017, 131, 1781–1799. [CrossRef]
- Zhou, H.Y.; Beevers, C.S.; Huang, S.L. The targets of curcumin. Curr. Drug Targets 2011, 12, 332–347. [CrossRef]
- Cheng, A.-L.; Hsu, C.-H.; Lin, J.-K.; Hsu, M.-M.; Ho, Y.-F.; Shen, T.-S.; Ko, J.-Y.; Lin, J.-T.; Lin, B.-R.; Ming-Shiang, W. Phase i clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 2001, 21, 2895–2900.
- Lao, C.D.; Ruffin, M.T.; Normolle, D.; Heath, D.D.; Murray, S.I.; Bailey, J.M.; Boggs, M.E.; Crowell, J.; Rock, C.L.; Brenner, D.E. Dose escalation of a curcuminoid formulation. BMC Complementary Altern. Med. 2006, 6, 10. [CrossRef]
- Rodriguez, J.C.; Santibanez, D.; Narayanan, S.; Dave, A. Ginger and curcumin in cancer prevention and health promotion. Bot. Med. Clin. Pract. 2008, 321.
- Authority, E.F.S. Refined exposure assessment for curcumin (e 100). EFSA J. 2014, 12, 3876. [CrossRef]
- Hewlings, S.; Kalman, D. Curcumin: A review of its’ effects on human health. Foods 2017, 6, 92. [CrossRef] [PubMed]
- DiSilvestro, R.A.; Joseph, E.; Zhao, S.; Bomser, J. Diverse effects of a low dose supplement of lipidated curcumin in healthy middle aged people. Nutr. J. 2012, 11, 79. [CrossRef] [PubMed]
- Cianfruglia, L.; Minnelli, C.; Laudadio, E.; Scire, A.; Armeni, T. Side effects of curcumin: Epigenetic and antiproliferative implications for normal dermal fibroblast and breast cancer cells. Antioxidants 2019, 8, 382. [CrossRef] [PubMed]
- Araiza-Calahorra, A.; Akhtar, M.; Sarkar, A. Recent advances in emulsion-based delivery approaches for curcumin: From encapsulation to bioaccessibility. Trends Food Sci. Technol. 2018, 71, 155–169. [CrossRef]
- Grynkiewicz, G.; S´lifirski, P. Curcumin and curcuminoids in quest for medicinal status. Acta Biochim. Pol. 2012, 59, 201–212. [CrossRef]
- Bernabé-Pineda, M.; Ram´lrez-Silva, M.a.T.; Romero-Romo, M.; González-Vergara, E.; Rojas-Hernández, A. Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2004, 60, 1091–1097. [CrossRef]
- Schneider, C.; Gordon, O.N.; Edwards, R.L.; Luis, P.B. Degradation of curcumin: From mechanism to biological implications. J. Agric. Food Chem. 2015, 63, 7606–7614. [CrossRef]
- Wang, Y.-J.; Pan, M.-H.; Cheng, A.-L.; Lin, L.-I.; Ho, Y.-S.; Hsieh, C.-Y.; Lin, J.-K. Stability of curcumin in buffer solutions and characterization of its degradation products. J. Pharm. Biomed. Anal. 1997, 15, 1867–1876. [CrossRef]
- Zheng, B.; Peng, S.; Zhang, X.; McClements, D.J. Impact of delivery system type on curcumin bioaccessibility: Comparison of curcumin-loaded nanoemulsions with commercial curcumin supplements. J. Agric. Food Chem. 2018, 66, 10816–10826. [CrossRef]
- Nelson, K.M.; Dahlin, J.L.; Bisson, J.; Graham, J.; Pauli, G.F.; Walters, M.A. The essential medicinal chemistry of curcumin: Miniperspective. J. Med. Chem. 2017, 60, 1620–1637. [CrossRef] [PubMed]
- Priyadarsini, K.I. Photophysics, photochemistry and photobiology of curcumin: Studies from organic solutions, bio-mimetics and living cells. J. Photochem. Photobiol. C Photochem. Rev. 2009, 10, 81–95. [CrossRef]
- Wright, L.; Frye, J.B.; Gorti, B.; Timmermann, B.N.; Funk, J.L. Bioactivity of turmeric-derived curcuminoids and related metabolites in breast cancer. Curr. Pharm. Des. 2013, 19, 6218–6225. [CrossRef] [PubMed]
- Ogiwara, T.; Satoh, K.; Kadoma, Y.; Murakami, Y.; Unten, S.; Atsumi, T.; Sakagami, H.; Fujisawa, S. Radical scavenging activity and cytotoxicity of ferulic acid. Anticancer Res. 2002, 22, 2711–2717. [PubMed]
- Tai, A.; Sawano, T.; Yazama, F.; Ito, H. Evaluation of antioxidant activity of vanillin by using multiple antioxidant assays. Biochim. Biophys. Acta 2011, 1810, 170–177. [CrossRef]
- Gordon, O.N.; Schneider, C. Vanillin and ferulic acid: Not the major degradation products of curcumin. Trends Mol. Med. 2012, 18, 361–363. [CrossRef]
- Gordon, O.N.; Luis, P.B.; Sintim, H.O.; Schneider, C. Unraveling curcumin degradation autoxidation proceeds through spiroepoxide and vinylether intermediates en route to the main bicyclopentadione. J. Biol. Chem. 2015, 290, 4817–4828. [CrossRef]
- Griesser, M.; Pistis, V.; Suzuki, T.; Tejera, N.; Pratt, D.A.; Schneider, C. Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin. J. Biol. Chem. 2011, 286, 1114–1124. [CrossRef]
- Sanidad, K.Z.; Zhu, J.; Wang, W.; Du, Z.; Zhang, G. Effects of stable degradation products of curcumin on cancer cell proliferation and inflammation. J. Agric. Food Chem. 2016, 64, 9189–9195. [CrossRef]
- McClements, D.J.; Li, F.; Xiao, H. The nutraceutical bioavailability classification scheme: Classifying nutraceuticals according to factors limiting their oral bioavailability. Annu. Rev. Food Sci. Technol. 2015, 6, 299–327. [CrossRef] [PubMed]
- Ravindranath, V.; Chandrasekhara, N. Absorption and tissue distribution of curcumin in rats. Toxicology 1980, 16, 259–265. [CrossRef]
- Sanidad, K.Z.; Sukamtoh, E.; Xiao, H.; McClements, D.J.; Zhang, G.D. Curcumin: Recent advances in the development of strategies to improve oral bioavailability. Annu. Rev. Food Sci. Technol. 2019, 10, 597–617.[CrossRef]
- Jain, G.; Patil, U.K. Strategies for enhancement of bioavailability of medicinal agents with natural products. Int. J. Pharm. Sci. Res. 2015, 6, 5315–5324.
- Mollazadeh, S.; Sahebkar, A.; Hadizadeh, F.; Behravan, J.; Arabzadeh, S. Structural and functional aspects of p-glycoprotein and its inhibitors. Life Sci. 2018, 214, 118–123. [CrossRef] [PubMed]
- Zhou, S.F.; Lim, L.Y.; Chowbay, B. Herbal modulation of p-glycoprotein. Drug Metab. Rev. 2004, 36, 57–104. [CrossRef]
- Singh, D.V.; Godbole, M.M.; Misra, K. A plausible explanation for enhanced bioavailability of p-gp substrates in presence of piperine: Simulation for next generation of p-gp inhibitors. J. Mol. Modeling 2013, 19, 227–238. [CrossRef]
- Prasad, S.; Tyagi, A.K.; Aggarwal, B.B. Recent developments in delivery, bioavailability, absorption and metabolism of curcumin: The golden pigment from golden spice. Cancer Res. Treat. 2014, 46, 2–18. [CrossRef]
- Ireson, C.R.; Jones, D.J.; Orr, S.; Coughtrie, M.W.; Boocock, D.J.; Williams, M.L.; Farmer, P.B.; Steward, W.P.; Gescher, A.J. Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol. Prev. Biomark. 2002, 11, 105–111.
- Ireson, C.; Orr, S.; Jones, D.J.; Verschoyle, R.; Lim, C.-K.; Luo, J.-L.; Howells, L.; Plummer, S.; Jukes, R.; Williams, M. 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, 1058–1064.
- Asai, A.; Miyazawa, T. Occurrence of orally administered curcuminoid as glucuronide and glucuronide/sulfate conjugates in rat plasma. Life Sci. 2000, 67, 2785–2793. [CrossRef]
- Sharma, R.A.; Euden, S.A.; Platton, S.L.; Cooke, D.N.; Shafayat, A.; Hewitt, H.R.; Marczylo, T.H.; Morgan, B.; Hemingway, D.; Plummer, S.M. Phase i clinical trial of oral curcumin: Biomarkers of systemic activity and compliance. Clin. Cancer Res. 2004, 10, 6847–6854. [CrossRef] [PubMed]
- Dubey, S.K.; Sharma, A.K.; Narain, U.; Misra, K.; Pati, U. Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties. Eur. J. Med. Chem. 2008, 43, 1837–1846. [CrossRef] [PubMed]
- Huang, Y.; Cao, S.; Zhang, Q.; Zhang, H.; Fan, Y.; Qiu, F.; Kang, N. Biological and pharmacological effects of hexahydrocurcumin, a metabolite of curcumin. Arch. Biochem. Biophys. 2018, 646, 31–37. [CrossRef] [PubMed]
- Srimuangwong, K.; Tocharus, C.; Chintana, P.Y.; Suksamrarn, A.; Tocharus, J. Hexahydrocurcumin enhances inhibitory effect of 5-fluorouracil on ht-29 human colon cancer cells. World J. Gastroenterol. 2012, 18, 2383. [CrossRef]
- Chen, C.-Y.; Yang, W.-L.; Kuo, S.-Y. Cytotoxic activity and cell cycle analysis of hexahydrocurcumin on sw 480 human colorectal cancer cells. Nat. Prod. Commun. 2011, 6, 1671–1672. [CrossRef]
- Zhang, Z.; Luo, D.; Xie, J.; Lin, G.; Zhou, J.; Liu, W.; Li, H.; Yi, T.; Su, Z.; Chen, J. Octahydrocurcumin, a final hydrogenated metabolite of curcumin, possesses superior anti-tumor activity through induction of cellular apoptosis. Food Funct. 2018, 9, 2005–2014. [CrossRef]
- Luo, D.-D.; Chen, J.-F.; Liu, J.-J.; Xie, J.-H.; Zhang, Z.-B.; Gu, J.-Y.; Zhuo, J.-Y.; Huang, S.; Su, Z.-R.; Sun, Z.-H. Tetrahydrocurcumin and octahydrocurcumin, the primary and final hydrogenated metabolites of curcumin, possess superior hepatic-protective effect against acetaminophen-induced liver injury: Role of cyp2e1 and keap1-nrf2 pathway. Food Chem. Toxicol. 2019, 123, 349–362. [CrossRef]
- Shoji, M.; Nakagawa, K.; Watanabe, A.; Tsuduki, T.; Yamada, T.; Kuwahara, S.; Kimura, F.; Miyazawa, T. Comparison of the effects of curcumin and curcumin glucuronide in human hepatocellular carcinoma hepg2 cells. Food Chem. 2014, 151, 126–132. [CrossRef]
- Shen, L.; Liu, C.-C.; An, C.-Y.; Ji, H.-F. How does curcumin work with poor bioavailability? Clues from experimental and theoretical studies. Sci. Rep. 2016, 6, 20872. [CrossRef]
- Perkins, S.; Verschoyle, R.D.; Hill, K.; Parveen, I.; Threadgill, M.D.; Sharma, R.A.; Williams, M.L.; Steward, W.P.; Gescher, A.J. Chemopreventive efficacy and pharmacokinetics of curcumin in the min/+ mouse, a model of familial adenomatous polyposis. Cancer Epidemiol. Prev. Biomark. 2002, 11, 535–540.
- Suresh, D.; Srinivasan, K. Tissue distribution & elimination of capsaicin, piperine & curcumin following oral intake in rats. Indian J. Med. Res. 2010, 131, 682–691. [PubMed]
- Ravindranath, V.; Chandrasekhara, N. Metabolism of curcumn-studies with [3 h] curcumin. Toxicology 1981, 22, 337–344. [CrossRef]
- Pan, M.-H.; Huang, T.-M.; Lin, J.-K. Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab. Dispos. 1999, 27, 486–494. [PubMed]
- Kakran, M.; Sahoo, N.G.; Tan, I.-L.; Li, L. Preparation of nanoparticles of poorly water-soluble antioxidant curcumin by antisolvent precipitation methods. J. Nanoparticle Res. 2012, 14, 757. [CrossRef]
- Yadav, D.; Kumar, N. Nanonization of curcumin by antisolvent precipitation: Process development, characterization, freeze drying and stability performance. Int. J. Pharm. 2014, 477, 564–577. [CrossRef]
- Patel, A.; Hu, Y.; Tiwari, J.K.; Velikov, K.P. Synthesis and characterisation of zein-curcumin colloidal particles. Soft Mater 2010, 6, 6192–6199. [CrossRef]
- Khan, F.I.; Ghoshal, A.K. Removal of volatile organic compounds from polluted air. J. Loss Prev. Process Ind. 2000, 13, 527–545. [CrossRef]
- Mozafari, M.R. Liposomes: An overview of manufacturing techniques. Cell. Mol. Biol. Lett. 2005, 10, 711.
- Lesoin, L.; Crampon, C.; Boutin, O.; Badens, E. Preparation of liposomes using the supercritical anti-solvent (sas) process and comparison with a conventional method. J. Supercrit. Fluids 2011, 57, 162–174. [CrossRef]
- Ginty, P.J.; Whitaker, M.J.; Shakesheff, K.M.; Howdle, S.M. Drug delivery goes supercritical. Mater. Today 2005, 8, 42–48. [CrossRef]
- Peng, S.; Li, Z.; Zou, L.; Liu, W.; Liu, C.; McClements, D.J. Enhancement of curcumin bioavailability by encapsulation in sophorolipid-coated nanoparticles: An in vitro and in vivo study. J. Agric. Food Chem. 2018, 66, 1488–1497. [CrossRef]
- Cheng, C.; Peng, S.; Li, Z.; Zou, L.; Liu, W.; Liu, C. Improved bioavailability of curcumin in liposomes prepared using a ph-driven, organic solvent-free, easily scalable process. RSC Adv. 2017, 7, 25978–25986. [CrossRef]
- Pan, K.; Luo, Y.; Gan, Y.; Baek, S.J.; Zhong, Q. Ph-driven encapsulation of curcumin in self-assembled casein nanoparticles for enhanced dispersibility and bioactivity. Soft Matter 2014, 10, 6820–6830. [CrossRef] [PubMed]
- Zhou, M.; Wang, T.; Hu, Q.; Luo, Y. Low density lipoprotein/pectin complex nanogels as potential oral delivery vehicles for curcumin. Food Hydrocoll. 2016, 57, 20–29. [CrossRef]
- Zheng, B.; Zhang, X.; Peng, S.; McClements, D.J. Impact of delivery system format on curcumin bioaccessibility: Nanocrystals, nanoemulsion droplets, and natural oil bodies. Food Funct. 2019, 10, 4339–4349. [CrossRef] [PubMed]
- Cabrera-Trujillo, M.A.; Sotelo-Díaz, L.I.; Quintanilla-Carvajal, M.X. Effect of amplitude and pulse in low frequency ultrasound on oil/water emulsions. DYNA 2016, 83, 63–68. [CrossRef]
- Kim, H.N.; Suslick, K.S. The effects of ultrasound on crystals: Sonocrystallization and sonofragmentation. Crystals 2018, 8, 280. [CrossRef]
- Zou, L.; Zheng, B.; Zhang, R.; Zhang, Z.; Liu, W.; Liu, C.; Xiao, H.; McClements, D.J. Food matrix effects on nutraceutical bioavailability: Impact of protein on curcumin bioaccessibility and transformation in nanoemulsion delivery systems and excipient nanoemulsions. Food Biophys. 2016, 11, 142–153. [CrossRef]
- Zou, L.; Zheng, B.; Zhang, R.; Zhang, Z.; Liu, W.; Liu, C.; Zhang, G.; Xiao, H.; McClements, D.J. Influence of lipid phase composition of excipient emulsions on curcumin solubility, stability, and bioaccessibility. Food Biophys. 2016, 11, 213–225. [CrossRef]
- Zhu, J.L.; Sanidad, K.Z.; Sukamtoh, E.; Zhang, G.D. Potential roles of chemical degradation in the biological activities of curcumin. Food Funct. 2017, 8, 907–914. [CrossRef] [PubMed]
- Kharat, M.; Skrzynski, M.; Decker, E.A.; McClements, D.J. Enhancement of chemical stability of curcumin- enriched oil-in-water emulsions: Impact of antioxidant type and concentration. Food Chem. 2020, 320, 126653. [CrossRef] [PubMed]
- Zou, L.Q.; Zheng, B.J.; Zhang, R.J.; Zhang, Z.P.; Liu, W.; Liu, C.M.; Xiao, H.; McClements, D.J. Food-grade nanoparticles for encapsulation, protection and delivery of curcumin: Comparison of lipid, protein, and phospholipid nanoparticles under simulated gastrointestinal conditions. RSC Adv. 2016, 6, 3126–3136. [CrossRef]
- Dai, L.; Zhou, H.L.; Wei, Y.; Gao, Y.X.; McClements, D.J. Curcumin encapsulation in zein-rhamnolipid composite nanoparticles using a ph-driven method. Food Hydrocoll. 2019, 93, 342–350. [CrossRef]
- Yallapu, M.M.; Jaggi, M.; Chauhan, S.C. Curcumin nanoformulations: A future nanomedicine for cancer. Drug Discov. Today. 2012, 17, 71–80. [CrossRef]
- del Castillo, M.L.R.; Lopez-Tobar, E.; Sanchez-Cortes, S.; Flores, G.; Blanch, G.P. Stabilization of curcumin against photodegradation by encapsulation in gamma-cyclodextrin: A study based on chromatographic and spectroscopic (raman and uv-visible) data. Vib. Spectrosc. 2015, 81, 106–111. [CrossRef]
- Price, L.C.; Buescher, R.W. Decomposition of turmeric curcuminoids as affected by light, solvent and oxygen. Food Biochem. 1996, 20, 125–133. [CrossRef]
- Higaki, K.; Yata, T.; Sone, M.; Ogawara, K.; Kimura, T. Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine. Res. Commun. Mol. Pathol. Pharmacol. 2001, 109, 231–240.
- Aungst, B.J. Intestinal permeation enhancers. J. Pharm. Sci. 2000, 89, 429–442. [CrossRef]
- Patra, A.K.; Amasheh, S.; Aschenbach, J.R. Modulation of gastrointestinal barrier and nutrient transport function in farm animals by natural plant bioactive compounds—A comprehensive review. Crit. Rev. Food Sci. Nutr. 2019, 59, 3237–3266. [CrossRef]
- McClements, D.J. Nanoparticle- and Microparticle-Based Delivery Systems: Encapsulation, Protection and Release of Active Components; CRC Press: Boca Raton, FL, USA, 2014.
- McClements, D.J. Enhancing nutraceutical bioavailability through food matrix design. Curr. Opin. Food Sci. 2015, 4, 1–6. [CrossRef]
- Dordevic, V.; Balanc, B.; Belscak-Cvitanovic, A.; Levic, S.; Trifkovic, K.; Kalusevic, A.; Kostic, I.; Komes, D.; Bugarski, B.; Nedovic, V. Trends in encapsulation technologies for delivery of food bioactive compounds. Food Eng. Rev. 2015, 7, 452–490. [CrossRef]
- Wang, Z.L. Bioavailability of organic compounds solubilized in nonionic surfactant micelles. Appl. Microbiol. Biotechnol. 2011, 89, 523–534. [CrossRef] [PubMed]
- Kimpel, F.; Schmitt, J.J. Review: Milk proteins as nanocarrier systems for hydrophobic nutraceuticals. Food Sci. 2015, 80, R2361–R2366. [CrossRef]
- Livney, Y.D. Milk proteins as vehicles for bioactives. Curr. Opin. Colloid Interface Sci. 2010, 15, 73–83. [CrossRef]
- Richtering, W. Rheology and shear induced structures in surfactant solutions. Curr. Opin. Colloid Interface Sci. 2001, 6, 446–450. [CrossRef]
- Torchilin, V.P. Micellar nanocarriers: Pharmaceutical perspectives. Pharm. Res. 2007, 24, 1–16. [CrossRef]
- Wang, X.Y.; Gao, Y. Effects of length and unsaturation of the alkyl chain on the hydrophobic binding of curcumin with tween micelles. Food Chem. 2018, 246, 242–248. [CrossRef]
- Pan, K.; Zhong, Q.; Baek, S.J. Enhanced dispersibility and bioactivity of curcumin by encapsulation in casein nanocapsules. J. Agric. Food Chem. 2013, 61, 6036–6043. [CrossRef]
- Schiborr, C.; Kocher, A.; Behnam, D.; Jandasek, J.; Toelstede, S.; Frank, J. 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, 516–527. [CrossRef]
- Akbarzadeh, A.; Rezaei-Sadabady, R.; Davaran, S.; Joo, S.W.; Zarghami, N.; Hanifehpour, Y.; Samiei, M.; Kouhi, M.; Nejati-Koshki, K. Liposome: Classification, preparation, and applications. Nanoscale Res. Lett. 2013, 8, 102. [CrossRef] [PubMed]
- Chen, X.; Zou, L.-Q.; Niu, J.; Liu, W.; Peng, S.-F.; Liu, C.-M. The stability, sustained release and cellular antioxidant activity of curcumin nanoliposomes. Molecules 2015, 20, 14293–14311. [CrossRef] [PubMed]
- Jin, H.-H.; Lu, Q.; Jiang, J.-G. Curcumin liposomes prepared with milk fat globule membrane phospholipids and soybean lecithin. J. Dairy Sci. 2016, 99, 1780–1790. [CrossRef] [PubMed]
- Takahashi, M.; Uechi, S.; Takara, K.; Asikin, Y.; Wada, K. Evaluation of an oral carrier system in rats: Bioavailability and antioxidant properties of liposome-encapsulated curcumin. J. Agric. Food Chem. 2009, 57, 9141–9146. [CrossRef] [PubMed]
- Li, C.; Zhang, Y.; Su, T.; Feng, L.; Long, Y.; Chen, Z. Silica-coated flexible liposomes as a nanohybrid delivery system for enhanced oral bioavailability of curcumin. Int. J. Nanomed. 2012, 7, 5995. [CrossRef] [PubMed]
- Bergonzi, M.; Hamdouch, R.; Mazzacuva, F.; Isacchi, B.; Bilia, A. Optimization, characterization and in vitro evaluation of curcumin microemulsions. LWT Food Sci. Technol. 2014, 59, 148–155. [CrossRef]
- Setthacheewakul, S.; Mahattanadul, S.; Phadoongsombut, N.; Pichayakorn, W.; Wiwattanapatapee, R. Development and evaluation of self-microemulsifying liquid and pellet formulations of curcumin, and absorption studies in rats. Eur. J. Pharm. Biopharm. 2010, 76, 475–485. [CrossRef] [PubMed]
- Hu, L.; Jia, Y.; Niu, F.; Jia, Z.; Yang, X.; Jiao, K. Preparation and enhancement of oral bioavailability of curcumin using microemulsions vehicle. J. Agric. Food Chem. 2012, 60, 7137–7141. [CrossRef] [PubMed]
- McClements, D.J. Food Emulsions: Principles, Practices, and Techniques; CRC Press: Boca Raton, FL, USA, 2015.
- McClements, D.J. Nanoemulsions versus microemulsions: Terminology, differences, and similarities. Soft Matter 2012, 8, 1719–1729. [CrossRef]
- Zheng, B.; Lin, H.; Zhang, X.; McClements, D.J. Fabrication of curcumin-loaded dairy milks using the ph-shift method: Formation, stability, and bioaccessibility. J. Agric. Food Chem. 2019, 67, 12245–12254. [CrossRef] [PubMed]
- Ma, P.; Zeng, Q.; Tai, K.; He, X.; Yao, Y.; Hong, X.; Yuan, F. Preparation of curcumin-loaded emulsion using high pressure homogenization: Impact of oil phase and concentration on physicochemical stability. LWT 2017, 84, 34–46. [CrossRef]
- Zou, L.; Zheng, B.; Liu, W.; Liu, C.; Xiao, H.; McClements, D.J. Enhancing nutraceutical bioavailability using excipient emulsions: Influence of lipid droplet size on solubility and bioaccessibility of powdered curcumin. J. Funct. Foods 2015, 15, 72–83. [CrossRef]
- Onodera, T.; Kuriyama, I.; Andoh, T.; Ichikawa, H.; Sakamoto, Y.; Lee-Hiraiwa, E.; Mizushina, Y. Influence of particle size on the in vitro and in vivo anti-inflammatory and anti-allergic activities of a curcumin lipid nanoemulsion. Int. J. Mol. Med. 2015, 35, 1720–1728. [CrossRef] [PubMed]
- Mishra, V.; Bansal, K.K.; Verma, A.; Yadav, N.; Thakur, S.; Sudhakar, K.; Rosenholm, J.M. Solid lipid nanoparticles: Emerging colloidal nano drug delivery systems. Pharmaceutics 2018, 10, 191. [CrossRef] [PubMed]
- Müller, R.H.; Radtke, M.; Wissing, S.A. Solid lipid nanoparticles (sln) and nanostructured lipid carriers (nlc) in cosmetic and dermatological preparations. Adv. Drug Deliv. Rev. 2002, 54, S131–S155. [CrossRef]
- Helgason, T.; Salminen, H.; Kristbergsson, K.; McClements, D.J.; Weiss, J. Formation of transparent solid lipid nanoparticles by microfluidization: Influence of lipid physical state on appearance. J. Colloid Interface Sci. 2015, 448, 114–122. [CrossRef]
- Xue, J.; Wang, T.; Hu, Q.; Zhou, M.; Luo, Y. Insight into natural biopolymer-emulsified solid lipid nanoparticles for encapsulation of curcumin: Effect of loading methods. Food Hydrocoll. 2018, 79, 110–116. [CrossRef]
- Kakkar, V.; Singh, S.; Singla, D.; Kaur, I.P. Exploring solid lipid nanoparticles to enhance the oral bioavailability of curcumin. Mol. Nutr. Food Res. 2011, 55, 495–503. [CrossRef]
- Sadegh Malvajerd, S.; Azadi, A.; Izadi, Z.; Kurd, M.; Dara, T.; Dibaei, M.; Sharif Zadeh, M.; Akbari Javar, H.; Hamidi, M. Brain delivery of curcumin using solid lipid nanoparticles and nanostructured lipid carriers: Preparation, optimization, and pharmacokinetic evaluation. ACS Chem. Neurosci. 2018, 10, 728–739. [CrossRef]
- Gota, V.S.; Maru, G.B.; Soni, T.G.; Gandhi, T.R.; Kochar, N.; Agarwal, M.G. Safety and pharmacokinetics of a solid lipid curcumin particle formulation in osteosarcoma patients and healthy volunteers. J. Agric. Food Chem. 2010, 58, 2095–2099. [CrossRef]
- McClements, D.J. Recent progress in hydrogel delivery systems for improving nutraceutical bioavailability. Food Hydrocoll. 2017, 68, 238–245. [CrossRef]
- Zheng, B.; Zhang, Z.; Chen, F.; Luo, X.; McClements, D.J. Impact of delivery system type on curcumin stability: Comparison of curcumin degradation in aqueous solutions, emulsions, and hydrogel beads. Food Hydrocoll. 2017, 71, 187–197. [CrossRef]
- Mohammadian, M.; Salami, M.; Momen, S.; Alavi, F.; Emam-Djomeh, Z. Fabrication of curcumin-loaded whey protein microgels: Structural properties, antioxidant activity, and in vitro release behavior. LWT 2019, 103, 94–100. [CrossRef]
- Zhang, Z.; Zhang, R.; Zou, L.; Chen, L.; Ahmed, Y.; Al Bishri, W.; Balamash, K.; McClements, D.J. Encapsulation of curcumin in polysaccharide-based hydrogel beads: Impact of bead type on lipid digestion and curcumin bioaccessibility. Food Hydrocoll. 2016, 58, 160–170. [CrossRef]
- Esmaili, M.; Ghaffari, S.M.; Moosavi-Movahedi, Z.; Atri, M.S.; Sharifizadeh, A.; Farhadi, M.; Yousefi, R.; Chobert, J.-M.; Haertlé, T.; Moosavi-Movahedi, A.A. Beta casein-micelle as a nano vehicle for solubility enhancement of curcumin; food industry application. LWT Food Sci. Technol. 2011, 44, 2166–2172. [CrossRef]
- Purpura, M.; Lowery, R.P.; Wilson, J.M.; Mannan, H.; Münch, G.; Razmovski-Naumovski, V. Analysis of different innovative formulations of curcumin for improved relative oral bioavailability in human subjects. Eur. J. Nutr. 2018, 57, 929–938. [CrossRef] [PubMed]
- Zheng, B.; Zhang, X.; Lin, H.; McClements, D.J. Loading natural emulsions with nutraceuticals using the ph-driven method: Formation & stability of curcumin-loaded soybean oils bodies. Food Funct. 2019, 10, 5473–5484.