Pharmacokinetics of pterostilbene in Sprague-Dawley rats: The impacts of aqueous solubility, fasting, dose escalation, and dosing route on bioavailability

Molecular Nutrition and Food Research

Volumn 57, Issue 6, 2013, Pages 1015-1025

  Yeo, Samuel Chao Ming ^a   Ho, Paul C ^a   Lin, Hai Shu ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Bioavailability; Dose manipulation; Pterostilbene; Solubility; Sublingual

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; 2-HYDROXYPROPYL-BETA-CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; PTEROSTILBENE; STILBENE DERIVATIVE;

ANIMAL; ARTICLE; BIOAVAILABILITY; CHEMISTRY; DIET RESTRICTION; DOSE RESPONSE; INTRAVENOUS ADMINISTRATION; MALE; ORAL DRUG ADMINISTRATION; RAT; SOLUBILITY; SPRAGUE DAWLEY RAT; SUBLINGUAL DRUG ADMINISTRATION;

ADMINISTRATION, INTRAVENOUS; ADMINISTRATION, ORAL; ADMINISTRATION, SUBLINGUAL; ANIMALS; BETA-CYCLODEXTRINS; BIOLOGICAL AVAILABILITY; DOSE-RESPONSE RELATIONSHIP, DRUG; FASTING; MALE; RATS; RATS, SPRAGUE-DAWLEY; SOLUBILITY; STILBENES;

RATTUS;

EID: 84878923206     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.201200651     Document Type: Article

References (66)

1. Roupe, K. A., Remsberg, C. M., Yanez, J. A., Davies, N. M., Pharmacometrics of stilbenes: seguing towards the clinic. Curr. Clin. Pharmacol. 2006, 1, 81-101.
2. Ruiz, M. J., Fernandez, M., Pico, Y., Manes, J. et al., Dietary administration of high doses of pterostilbene and quercetin to mice is not toxic. J. Agric. Food Chem. 2009, 57, 3180-3186.
3. Baur, J. A., Sinclair, D. A., Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov. 2006, 5, 493-506.
4. Smoliga, J. M., Baur, J. A., Hausenblas, H. A., Resveratrol and health-a comprehensive review of human clinical trials. Mol. Nutr. Food Res. 2011, 55, 1129-1141.
5. Remsberg, C. M., Yanez, J. A., Ohgami, Y., Vega-Villa, K. R. et al., Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, anticancer, antiinflammatory, antioxidant and analgesic activity. Phytother. Res. 2008, 22, 169-179.
6. Joseph, J. A., Fisher, D. R., Cheng, V., Rimando, A. M. et al., Cellular and behavioral effects of stilbene resveratrol analogues: implications for reducing the deleterious effects of aging. J. Agric. Food Chem. 2008, 56, 10544-10551.
7. Pan, M. H., Lai, C. S., Tsai, M. L., Wu, J. C. et al., Molecular mechanisms for anti-aging by natural dietary compounds. Mol. Nutr. Food Res. 2012, 56, 88-115.
8. Zhang, L., Zhou, G., Song, W., Tan, X. et al., Pterostilbene protects vascular endothelial cells against oxidized low-density lipoprotein-induced apoptosis in vitro and in vivo. Apoptosis: Int. J. Program. Cell Death 2012, 17, 25-36.
9. Zhang, L., Cui, L., Zhou, G., Jing, H. et al., Pterostilbene, a natural small-molecular compound, promotes cytoprotective macroautophagy in vascular endothelial cells. J. Nutr. Biochem. 2013, doi: 10.1016/j.jnutbio.2012.06.008.
10. McCormack, D., McFadden, D., Pterostilbene and cancer: current review. J. Surg. Res. 2012, 173, e53-e61.
11. Rimando, A. M., Suh, N., Biological/chemopreventive activity of stilbenes and their effect on colon cancer. Planta Med. 2008, 74, 1635-1643.
12. Pari, L., Satheesh, M. A., Effect of pterostilbene on hepatic key enzymes of glucose metabolism in streptozotocin- and nicotinamide-induced diabetic rats. Life Sci. 2006, 79, 641-645.
13. Satheesh, M. A., Pari, L., Effect of pterostilbene on lipids and lipid profiles in streptozotocin-nicotinamide induced type 2 diabetes mellitus. J. Appl. Biomed. 2008, 6, 31-37.
14. Rimando, A. M., Nagmani, R., Feller, D. R., Yokoyama, W., Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. J. Agric. Food Chem. 2005, 53, 3403-3407.
15. Manickam, M., Ramanathan, M., Jahromi, M. A., Chansouria, J. P. et al., Antihyperglycemic activity of phenolics from Pterocarpus marsupium. J. Nat. Prod. 1997, 60, 609-610.
16. Amarnath Satheesh, M., Pari, L., The antioxidant role of pterostilbene in streptozotocin-nicotinamide-induced type 2 diabetes mellitus in Wistar rats. J. Pharm. Pharmacol. 2006, 58, 1483-1490.
17. Kuo, P. L., Hsu, Y. L., Tsai, M. J., Huang, M. S., Pterostilbene suppresses benzo[a]pyrene-induced airway remodeling. J. Agric. Food Chem. 2011, 59, 8028-8035.
18. Macickova, T., Drabikova, K., Nosal, R., Bauerova, K. et al., In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis. Neuro. Endocrinol Lett. 2010, 31 Suppl 2, 91-95.
19. Pan, M. H., Chang, Y. H., Tsai, M. L., Lai, C. S. et al., Pterostilbene suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages. J. Agric. Food Chem. 2008, 56, 7502-7509.
20. Cichocki, M., Paluszczak, J., Szaefer, H., Piechowiak, A. et al., Pterostilbene is equally potent as resveratrol in inhibiting 12-O-tetradecanoylphorbol-13-acetate activated NFkappaB, AP-1, COX-2, and iNOS in mouse epidermis. Mol. Nutr. Food Res. 2008, 52 (Suppl 1), S62-S70.
21. Qureshi, A. A., Guan, X. Q., Reis, J. C., Papasian, C. J. et al., Inhibition of nitric oxide and inflammatory cytokines in LPS-stimulated murine macrophages by resveratrol, a potent proteasome inhibitor. Lip. Health Dis. 2012, 11, 76.
22. McCormack, D., McDonald, D., McFadden, D., Pterostilbene ameliorates tumor necrosis factor alpha-induced pancreatitis in vitro. J. Surg. Res. 2012, 178, 28-32.
23. Hsu, C. L., Lin, Y. J., Ho, C. T., Yen, G. C., Inhibitory effects of garcinol and pterostilbene on cell proliferation and adipogenesis in 3T3-L1 cells. Food Funct. 2012, 3, 49-57.
24. Chakraborty, A., Gupta, N., Ghosh, K., Roy, P., In vitro evaluation of the cytotoxic, anti-proliferative and anti-oxidant properties of pterostilbene isolated from Pterocarpus marsupium. Toxicol. In Vitro Int. J. Publ. Assoc. BIBRA 2010, 24, 1215-1228.
25. Mikstacka, R., Ignatowicz, E., [Chemopreventive and chemotherapeutic effect of trans-resveratrol and its analogues in cancer]. Pol. Merkur Lekarski 2010, 28, 496-500.
26. Perecko, T., Drabikova, K., Rackova, L., Ciz, M. et al., Molecular targets of the natural antioxidant pterostilbene: effect on protein kinase C, caspase-3 and apoptosis in human neutrophils in vitro. Neuro. Endocrinol. Lett. 2010, 31 Suppl 2, 84-90.
27. Kim, J. S., Ha, T. Y., Ahn, J., Kim, H. K. et al., Pterostilbene from Vitis coignetiae protect H2O2-induced inhibition of gap junctional intercellular communication in rat liver cell line. Food Chem. Toxicol. 2009, 47, 404-409.
28. Rimando, A. M., Cuendet, M., Desmarchelier, C., Mehta, R. G. et al., Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. J. Agric. Food Chem. 2002, 50, 3453-3457.
29. Perecko, T., Jancinova, V., Drabikova, K., Nosal, R. et al., Structure-efficiency relationship in derivatives of stilbene. Comparison of resveratrol, pinosylvin and pterostilbene. Neuro. Endocrinol. Lett. 2008, 29, 802-805.
30. Shi, Y. W., Wang, C. P., Liu, L., Liu, Y. L. et al., Antihyperuricemic and nephroprotective effects of resveratrol and its analogues in hyperuricemic mice. Mol. Nutr. Food. Res. 2012, 56, 1433-1444.
31. Meng, X. L., Yang, J. Y., Chen, G. L., Wang, L. H. et al., Effects of resveratrol and its derivatives on lipopolysaccharide-induced microglial activation and their structure-activity relationships. Chem. Biol. Interact 2008, 174, 51-59.
32. Chang, J., Rimando, A., Pallas, M., Camins, A. et al., Low-dose pterostilbene, but not resveratrol, is a potent neuromodulator in aging and Alzheimer's disease. Neurobiol. Aging 2012, 33, 2062-2071.
33. Riche, D. M., Deschamp, D., Griswold, M. E., McEwen, C. L. et al., Impact of pterostilbene on blood pressure and other metabolic parameters in adults. Hypertension 2012, 60, A617.
34. Lin, J. H., Lu, A. Y., Role of pharmacokinetics and metabolism in drug discovery and development. Pharmacol Rev. 1997, 49, 403-449.
35. Scott, E., Steward, W. P., Gescher, A. J., Brown, K., Resveratrol in human cancer chemoprevention-choosing the 'right' dose. Mol. Nutr. Food Res. 2012, 56, 7-13.
36. Cottart, C. H., Nivet-Antoine, V., Laguillier-Morizot, C., Beaudeux, J. L., Resveratrol bioavailability and toxicity in humans. Mol. Nutr. Food Res. 2010, 54, 7-16.
37. Kapetanovic, I. M., Muzzio, M., Huang, Z., Thompson, T. N. et al., Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats. Cancer Chemother. Pharmacol. 2011, 68, 593-601.
38. Lin, H. S., Yue, B. D., Ho, P. C., Determination of pterostilbene in rat plasma by a simple HPLC-UV method and its application in pre-clinical pharmacokinetic study. Biomed. Chromatogr. 2009, 23, 1308-1315.
39. Chiou, Y. S., Tsai, M. L., Nagabhushanam, K., Wang, Y. J. et al., Pterostilbene is more potent than resveratrol in preventing azoxymethane (AOM)-induced colon tumorigenesis via activation of the NF-E2-related factor 2 (Nrf2)-mediated antioxidant signaling pathway. J. Agric. Food Chem. 2011, 59, 2725-2733.
40. Nutakul, W., Sobers, H. S., Qiu, P., Dong, P. et al., Inhibitory effects of resveratrol and pterostilbene on human colon cancer cells: a side-by-side comparison. J. Agric. Food Chem. 2011, 59, 10964-10970.
41. Mikstacka, R., Przybylska, D., Rimando, A. M., Baer-Dubowska, W., Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by trans-resveratrol methyl ethers. Mol. Nutr. Food Res. 2007, 51, 517-524.
42. Zhang, W., Sviripa, V., Kril, L. M., Chen, X. et al., Fluorinated N, N-dialkylaminostilbenes for Wnt pathway inhibition and colon cancer repression. J. Med. Chem. 2011, 54, 1288-1297.
43. Hagiwara, K., Kosaka, N., Yoshioka, Y., Takahashi, R. U. et al., Stilbene derivatives promote Ago2-dependent tumour-suppressive microRNA activity. Sci. Rep. 2012, 2, 314.
44. Mena, S., Rodriguez, M. L., Ponsoda, X., Estrela, J. M. et al., Pterostilbene-induced tumor cytotoxicity: a lysosomal membrane permeabilization-dependent mechanism. PLoS One 2012, 7, e44524.
45. Das, S., Lin, H. S., Ho, P. C., Ng, K. Y., The impact of aqueous solubility and dose on the pharmacokinetic profiles of resveratrol. Pharm. Res. 2008, 25, 2593-2600.
46. Lin, H. S., Ho, P. C., Preclinical pharmacokinetic evaluation of resveratrol trimethyl ether in Sprague-Dawley rats: the impacts of aqueous solubility, dose escalation, food and repeated dosing on oral bioavailability. J. Pharm. Sci. 2011, 100, 4491-4500.
47. Bethune, S. J., Schultheiss, N., Henck, J. O., Improving the poor aqueous solubility of nutraceutical compound pterostilbene through cocrystal formation. Cryst. Growth Des. 2011, 11, 2817-2823.
48. Lin, H. S., Spatafora, C., Tringali, C., Ho, P. C., Determination of trans-2, 4, 3', 4', 5'-pentamethoxystilbene in rat plasma and its application to a pharmacokinetic study. J. Pharm. Biomed. Anal. 2012, 57, 94-98.
49. Lin, H. S., Sviripa, V. M., Watt, D. S., Liu, C. M. et al., Quantification of trans-2, 6-Difluoro-4'-N, N-dimethylaminostilbene in rat plasma: application to a pharmacokinetic study. J. Pharm. Biomed. Anal. 2013, 72, 115-120.
50. Davis, M. E., Brewster, M. E., Cyclodextrin-based pharmaceutics: past, present and future. Nat. Rev. Drug Discov. 2004, 3, 1023-1035.
51. National Advisory Committee for Laboratory Animal Research, Guidelines on the Care and Use of Animals for Scientific Purposes, Singapore, 2004.
52. Lin, H. S., Leong, W. W., Yang, J. A., Lee, P. et al., Biopharmaceutics of 13-cis-retinoic acid (isotretinoin) formulated with modified beta-cyclodextrins. Int. J. Pharm. 2007, 341, 238-245.
53. Lin, H. S., Chan, S. Y., Low, K. S., Shoon, M. L. et al., Kinetic study of a 2-hydroxypropyl-beta-cyclodextrin-based formulation of all-trans-retinoic acid in Sprague-Dawley rats after oral or intravenous administration. J. Pharm. Sci. 2000, 89, 260-267.
54. Hurst, S., Loi, C. M., Brodfuehrer, J., El-Kattan, A., Impact of physiological, physicochemical and biopharmaceutical factors in absorption and metabolism mechanisms on the drug oral bioavailability of rats and humans. Exp. Opin. Drug Metab. Toxicol. 2007, 3, 469-489.
55. Chan, O. H., Stewart, B. H., Physicochemical and drug-delivery considerations for oral drug bioavailability. Drug Discov. Today 1996, 1, 461-473.
56. Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02. September 26, 2012.
57. Suh, N., Paul, S., Hao, X., Simi, B. et al., Pterostilbene, an active constituent of blueberries, suppresses aberrant crypt foci formation in the azoxymethane-induced colon carcinogenesis model in rats. Clin. Cancer Res. 2007, 13, 350-355.
58. Pan, M. H., Chiou, Y. S., Chen, W. J., Wang, J. M. et al., Pterostilbene inhibited tumor invasion via suppressing multiple signal transduction pathways in human hepatocellular carcinoma cells. Carcinogenesis 2009, 30, 1234-1242.
59. Chiou, Y. S., Tsai, M. L., Wang, Y. J., Cheng, A. C. et al., Pterostilbene inhibits colorectal aberrant crypt foci (ACF) and colon carcinogenesis via suppression of multiple signal transduction pathways in azoxymethane-treated mice. J. Agric. Food Chem. 2010, 58, 8833-8841.
60. Chen, R. J., Tsai, S. J., Ho, C. T., Pan, M. H. et al., Chemopreventive effects of pterostilbene on urethane induced lung carcinogenesis in mice via the inhibition of EGFR mediated pathways and the induction of apoptosis and autophagy. J. Agric. Food Chem. 2012, 60, 11533-11541.
61. Tsai, M. L., Lai, C. S., Chang, Y. H., Chen, W. J. et al., Pterostilbene, a natural analogue of resveratrol, potently inhibits 7, 12-dimethylbenz[a]anthracene (DMBA)/12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse skin carcinogenesis. Food Funct. 2012, 3, 1185-1194.
62. Paul, S., DeCastro, A. J., Lee, H. J., Smolarek, A. K. et al., Dietary intake of pterostilbene, a constituent of blueberries, inhibits the beta-catenin/p65 downstream signaling pathway and colon carcinogenesis in rats. Carcinogenesis 2010, 31, 1272-1278.
63. Siegel, R., Naishadham, D., Jemal, A., Cancer statistics, 2012. CA Cancer J. Clin. 2012, 62, 10-29.
64. Petersen, P. E., Oral cancer prevention and control-the approach of the World Health Organization. Oral Oncol. 2009, 45, 454-460.
65. Hong, W. K., Endicott, J., Itri, L. M., Doos, W. et al., 13-cis-retinoic acid in the treatment of oral leukoplakia. N. Engl. J. Med. 1986, 315, 1501-1505.
66. Pettit, G. R., Grealish, M. P., Jung, M. K., Hamel, E. et al., Antineoplastic agents. 465. Structural modification of resveratrol: sodium resverastatin phosphate. J. Med. Chem. 2002, 45, 2534-2542.