1,733
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Natural products derived from tea on the solubility of hesperidin by LC-TOF/MS and NMR

, , , &
Pages S270-S278 | Received 09 Nov 2016, Accepted 11 Feb 2017, Published online: 17 May 2017

References

  • Garg, A.; Garg, S.; Zaneveld, L.J.D.; Singla, A.K. Chemistry and Pharmacology of the Citrus Bioflavonoid Hesperidin. Phytotherapy Research 2001, 15, 655–669.
  • Ho, S.; Su, M.; Lin, C. Comparison of Peroxynitrite-Scavenging Capacities of Several Citrus Fruit Peels. International Journal of Food Properties 2014, 17, 111–124.
  • Galati, E.M.; Monforte, M.T.; Kirjavainen, S.; Forestieri, A.M.; Trovato, A.; Tripodo, M.M. Biological Effects of Hesperidin, a Citrus Flavonoid. (Note I): Antiinflammatory and Analgesic Activity. Farmaco 1994, 40, 709–712.
  • Roohbakhsh, A.; Parhiz, H.; Soltani, F.; Iranshahi, R.; Iranshahi, M. Molecular Mechanisms behind the Biological Effects of Hesperidin and Hesperetin for the Prevention of Cancer and Cardiovascular Diseases. Life Sciences 2015, 124, 64–74.
  • Pinho-Ribeiro, F.A.; Hohmann, M.S.N.; Borghi, S.M.; Zarpelon, A.C.; Guazelli, C.F.S.; Manchope, M.F.; Casagrande, R.; Waldiceu, A.V.J. Protective Effects of the Flavonoid Hesperidin Methyl Chalcone in Inflammation and Pain in Mice: Role of TRPV1, Oxidative Stress, Cytokines and NF-κB. Chemico-Biological Interactions 2015, 228, 88–99.
  • Vallejo, F.; Larrosa, M.; Escudero, E.; Zafrilla, M.P.; Cerda, B.; Boza, J.; et al. Concentration and Solubility of Flavanones in Orange Beverages Affect Their Bioavailability in Humans. Journal of Agricultural and Food Chemistry 2010, 58, 6516–6524.
  • Walle, T. Methylation of Dietary Flavones Greatly Improves Their Hepatic Metabolic Stability and Intestinal Absorption. Molecular Pharmacology 2007, 4, 826–832.
  • Kometani, T.; Terada, Y.; Nishimura, T.; Takii, H.; Okada, S. Transglycosylation to Hesperidin by Cyclodextrin Glucanotransferase from an Alkalophilic Bacillus Species in Alkaline pH and Properties of Hesperidin Glycosides. Bioscience, Biotechnology, and Biochemistry 1994, 58, 1990–1994.
  • Majumdar, S.; Srirangam, R. Solubility, Stability, Physicochemical Characteristics and in Vitro Ocular Tissue Permeability of Hesperidin: A Natural Bioflavonoid. Pharmaceutical Research 2009, 26, 1217–1225.
  • Nakayama, H.; Tanaka, T.; Miyata, Y.; Saito, Y.; Matsui, T.; Aramaki, S.; et al. Development of Soluble Hesperidin-Containing Fermented Tea Made from Unripe Mandarin Orange Fruits and Third Crop Green Tea Leaves. Journal of Japan Society of Nutrition and Food Sciences 2014, 67, 95−103.
  • Cao, R.; Kobayashi, Y.; Nonaka, A.; Miyata, Y.; Tanaka, K.; Tanaka, T.; Matsui, T. NMR Spectroscopic and Quantum Mechanical Analyses of Enhanced Solubilization of Hesperidin by Theasinensin A. Pharmaceutical Research 2015, 32, 2301–2309.
  • Afaq, F.; Adhami, V.M.; Ahmad, N.; Mukhtar, H. Health Benefits of Tea Consumption. Tropical Journal of Pharmaceutical Research 2007, 6, 785–792.
  • Yang, C.S.; Chen, G.; Wu, Q. Recent Scientific Studies of a Traditional Chinese Medicine, Tea, on Prevention of Chronic Diseases. Journal of Traditional and Complementary Medicine 2014, 4:17–23.
  • Kobayashi, M.; Kawano, T.; Ukawa, Y.; Sagesaka, Y.M.; Fukuhara, I. Green Tea Beverages Enriched with Catechins with a Galloyl Moiety Reduce Body Fat in Moderately Obese Adults: A Randomized Double-Blind Placebo-Controlled Trial. Food & Function 2016, 7, 498–507.
  • Fujiki, H.; Imai, K.; Nakachi, K.; Sueoka, E.; Watanabe, T.; Suganuma, M. Innovative Strategy of Cancer Treatment with the Combination of Green Tea Catechins and Anticancer Compounds. Cancer Cell & Microenvironment 2015, 2, e886.
  • Barnes, P.J. Theophylline. American Journal of Respiratory and Critical Care Medicine 2013, 188, 901–906.
  • Kanehara, M.; Yokoyama, A.; Tomoda, Y.; Shiota, N.; Iwamoto, H.; Ishikawa, N.; Taooka, Y.; Haruta, Y.; Hattori, N.; Kohno, N. Anti-Inflammatory Effects and Clinical Efficacy of Theophylline and Tulobuterol in Mild-to-Moderate Chronic Obstructive Pulmonary Disease. Pulmonary Pharmacology and Therapeutics 2008, 21, 874–878.
  • Zu, M.; Yang, F.; Zhou, W.; Liu, A.; Du, G.; Zheng, L. In Vitro Anti-Influenza Virus and Anti-Inflammatory Activities of Theaflavin Derivatives. Antiviral Research 2012, 94, 217–224.
  • de Oliveira, A.; Prince, D.; Lo, C.Y.; Lee, L.H.; Chu, T.C. Antiviral Activity of Theaflavin Digallate against Herpes Simplex Virus Type 1. Antiviral Research 2015, 118, 56–67.
  • Teng. Q. Structural Biology: Practical NMR Applications; Springer: New York, 2005.
  • Zhang, J.; Tozuka, Y.; Uchiyama, H.; Higashi, K.; Moribe, K.; Takeuchi, H.; Yamamoto, K. NMR Investigation of a Novel Excipient, α-Glucosylhesperidin, as a Suitable Solubilizing Agent for Poorly Water-Soluble Drugs. Journal of Pharmaceutical Sciences 2011, 100, 4421–4431.
  • Johnson, J.C.S. Diffusion Ordered Nuclear Magnetic Resonance Spectroscopy: Principles and Applications. Progress in Nuclear Magnetic Resonance Spectroscopy 1999, 34, 203–256.
  • Brand, T.; Cabrita, E.J.; Berger, S. Intermolecular Interaction as Investigated by NOE and Diffusion Studies. Progress in Nuclear Magnetic Resonance Spectroscopy 2005, 46, 159–196.
  • Nishizawa, M.; Hosoya, T.; Hirokawa, T.; Shin-ya, K.; Kumazawa, S. NMR Spectroscopic Characterization of Inclusion Complexes of Theaflavin Digallate and Cyclodextrins. Food Science and Technology Research 2014, 20, 663–670.
  • Caligiani, A.; Acquotti, D.; Palla, G.; Bocchi, V. Identification and Quantification of the Main Organic Components of Vinegars by High Resolution 1H NMR Spectroscopy. Analytica Chimica Acta 2007, 585, 110−119.
  • Lucas, L.H.; Otto, W.H.; Larive, C.K. The 2D-J-DOSY Experiment: Resolving Diffusion Coefficients in Mixtures. Journal of Magnetic Resonance 2002, 156:138−145.
  • Divakar, S.; Agric, J. Structure of a Beta-Cyclodextrin-Vanillin Inclusion Complex. Food Chemistry 1990, 38, 940−944.
  • Cai, Y.; Gaffney, S.H.; Lilley, T.H.; Magnolato, D.; Martin, R.; Spencer, C.M.; et al. Polyphenol Interactions. Part 4. Model Studies with Caffeine and Cyclodextrins. Journal of the Chemical Society, Perkin Transactions 1990, 2, 2197−2209.
  • Maltese, F.; Erkelens, C.; der. Kooy, F.V.; Choi, Y.H.; Verpoorte, R. Identification of Natural Epimeric Flavanone Glycosides by NMR Spectroscopy. Food Chemistry 2009, 116, 575–579.
  • Baranac-Stojanović, M.; Koch, A.; Kleinpeter, E. Is the Conventional Interpretation of the Anisotropic Effects of C=C Double Bonds and Aromatic Rings in NMR Spectra in Terms of the π-Electron Shielding/Deshielding Contributions Correct? Chemistry - A European Journal 2012, 18, 370−376.
  • Ficarra, R.; Tommasini, S.; Raneri, D.; Calabro, M.L.; Di Bella, M.R.; Rustichelli, C.; et al. Study of Flavonoids/β-Cyclodextrins Inclusion Complexes by NMR, FT-IR, DSC, X-ray Investigation. Journal of Pharmaceutical and Biomedical Analysis 2002, 29, 1005–1014.
  • Rasool, A.A.; Hussain, A.A.; Dittert, L.W. Solubility Enhancement of Some Water-Insoluble Drugs in the Presence of Nicotinamide and Related Compounds. Journal of Pharmaceutical Sciences 1991, 80, 387–393.
  • Cao, R.; Nonaka, A.; Komura, F.; Matsui, T. Application of Diffusion Ordered-1H-Nuclear Magnetic Resonance Spectroscopy to Quantify Sucrose in Beverages. Food Chemistry 2015, 171, 8–12.
  • Cao, R,; Komura, F.; Nonaka, A.; Kato, T.; Fukumashi, J.; Matsui, T. Quantitative Analysis of D-(+)-Glucose in Fruit Juices Using Diffusion Ordered-1H Nuclear Magnetic Resonance Spectroscopy. Analytical Sciences 2014, 30, 383–388.
  • Cabrita, E.J.; Berger, S. DOSY Studies of Hydrogen Bond Association: Tetramethylsilane as a Reference Compound for Diffusion Studies. Magnetic Resonance in Chemistry 2001, 39, S142–148.
  • Sherrill, C.D. Energy Component Analysis of π Interactions. Accounts of Chemical Research 2013, 46, 1020–1028.

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.