Development and validation of a highly sensitive LC-MS/MS-ESI method for the determination of nobiletin in rat plasma: Application to a pharmacokinetic study

Biomedical Chromatography

Volumn 26, Issue 12, 2012, Pages 1464-1471

  Kumar, Avinash ^a   Devaraj, V C ^a   Giri, Kalpesh C ^a   Giri, Sanjeev ^a   Rajagopal, Sriram ^a   Mullangi, Ramesh ^a  

^a JUBILANT BIOSYS LTD   (India)

Author keywords

LC MS MS; Method validation; Nobiletin; Pharmacokinetics; Rat plasma

Indexed keywords

BODY FLUIDS; ELECTROSPRAY IONIZATION; EXTRACTION; HIGH PRESSURE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POSITIVE IONS; RATS;

ASSAY METHODS; INTERNAL STANDARDS; LC-MS-MS; LC.MS/MS; LIQUID CHROMATOGRAPHY COUPLED TO TANDEM MASS SPECTROMETRY; METHOD VALIDATIONS; NOBILETIN; PHARMACOKINETIC STUDIES; RAPID ASSAY; RAT PLASMA;

PHARMACOKINETICS;

NOBILETIN;

ACCURACY; ARTICLE; DRUG BLOOD LEVEL; DRUG STRUCTURE; ELECTROSPRAY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRACTICE GUIDELINE; RAT; SENSITIVITY ANALYSIS; VALIDATION STUDY;

RATTUS;

EID: 84867723564     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.2717     Document Type: Article

References (32)

1. Ben-Aziz A. Nobiletin is main fungistat in tangerines resistant to Mal Secco. Science 1967; 155: 1026-1027.
2. Bonfiglio R, King RC, Olah TV and Merkle K. The effects of sample preparation methods on the variability of the electrospray ionization response for model drug compounds. Rapid Communications in Mass Spectrometry 1999; 13: 1175-1185.
3. Choi SY, Hwang JH, Ko HC, Park JG and Kim SJ. Nobiletin from citrus fruit peel inhibits the DNA-binding activity of NF-kappaβ and ROS production in LPS- activated RAW 264.7 cells. Journal of Ethnopharmacology 2007; 113: 149-155.
4. Cui Y, Wu J, Jung SC, Park DB, Maeng YH, Hong JY, Kim SJ, Lee SR, Kim SJ, Kim SJ and Eun SY. Anti-neuroinflammatory activity of nobiletin on suppression of microglial activation. Biological and Pharmaceutical Bulletin 2010; 33: 1814-1821.
5. Eguchi A, Murakami A and Ohigashi H. Nobiletin, a citrus flavonoid, suppresses phorbol ester-induced expression of multiple scavenger receptor genes in THP-1 human monocytic cells. FEBS Letters 2006; 580: 3321-3328.
6. Hirata Y, Masuda Y, Kakutani H, Higuchi T, Takada K, Ito A, Nakagawa Y and Ishii H. Sp1 is an essential transcription factor for LPS-induced tissue factor expression in THP-1 monocytic cells, and nobiletin represses the expression through inhibition of NF-kappaB, AP-1, and Sp1 activation. Biochemical Pharmacology 2008; 75: 1504-1514.
7. Horowitz RM and Gentili B. Flavonoid constituents of citrus. In Citrus Science and Technology, Vol. 1. Avi: Westport, CT, 1977; 397-426.
8. Ishiwa J, Sato T, Mimaki Y, Sashida Y, Yano M and Ito A. A citrus flavonoid, nobiletin, suppresses production and gene expression of matrix metalloproteinase 9/gelatinase B in rabbit synovial fibroblasts. The Journal of Rheumatology 2000; 27: 20-25.
9. Ito A, Ishiwa J, Sato T, Mimaki Y and Sashida Y. The citrus flavonoid nobiletin suppresses the production and gene expression of matrix metalloproteinases-9/gelatinase B in rabbit synovial cells. Annals of the New York Academy of Sciences 1999; 878: 632-634.
10. Koga N, Matsuo M, Ohta C, Haraguchi K, Matsuoka M, Kato Y, Ishii T, Yano M and Ohta H. Comparative study of nobiletin metabolism with liver microsomes from rats, guinea pigs and hamsters and rat cytochrome P450. Biological and Pharmaceutical Bulletin 2007; 30: 2317-2323.
11. Li S, Wang Z, Sang S, Huang MT and Ho CT. Identification of nobiletin metabolites in mouse urine. Molecular Nutrition and Food Research 2006; 50: 291-299.
12. Li S, Sang S, Pan MH, Lai CS, Lo CY, Yang CS and Ho CT. Anti-inflammatory property of the urinary metabolites of nobiletin in mouse. Bioorganic and Medicinal Chemistry Letters 2007; 17: 5177-5181.
13. Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M and Ito A. Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochemical Pharmacology 2003; 65: 2065-2071.
14. Luo G, Guan X and Zhou L. Apoptotic effect of citrus fruit extract nobiletin on lung cancer cell line A549 in vitro and in vivo. Cancer Biology and Therapy 2008; 7: 966-973.
15. Manthey JA, Cesar TB, Jackson E and Mertens-Talcott S. Pharmacokinetic study of nobiletin and tangeretin in rat serum by high-performance liquid chromatography-electrospray ionization-mass spectrometry. Journal of Agricultural and Food Chemistry 2011; 59: 145-151.
16. Matsuzaki K, Yamakuni T, Hashimoto M, Haque AM, Shido O, Mimaki Y, Sashida Y and Ohizumi Y. Nobiletin restoring β-amyloid-impaired CREB phosphorylation rescues memory deterioration in Alzheimer's disease model rats. Neuroscience Letters 2006; 400: 230-234.
17. Matsuzaki K, Miyazaki K, Sakai S, Yawo H, Nakata N, Moriguchi S, Fukunaga K, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T and Ohizumi Y. Nobiletin, a citrus flavonoid with neurotrophic action, augments protein kinase A-mediated phosphorylation of the AMPA receptor subunit, GluR1, and the postsynaptic receptor response to glutamate in murine hippocampus. European Journal of Pharmacology 2008; 578: 194-200.
18. Minagawa A, Otani Y, Kubota T, Wada N, Furukawa T, Kumai K, Kameyama K, Okada Y, Fujii M, Yano M, Sato T, Ito A and Kitajima M. The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. Japanese Journal of Cancer Research 2001; 92: 1322-1328.
19. Miyamoto S, Yasui Y, Tanaka T, Ohigashi H and Murakami A. Suppressive effects of nobiletin on hyperleptinemia and colitis-related colon carcinogenesis in male ICR mice. Carcinogenesis 2008; 29: 1057-1063.
20. Miyata Y, Sato T, Yano M and Ito A. Activation of protein kinase C betaII/epsilon-c-Jun NH2-terminal kinase pathway and inhibition of mitogen-activated protein/ extracellular signal-regulated kinase 1/2 phosphorylation in antitumor invasive activity induced by the polymethoxy flavonoid, nobiletin. Molecular Cancer Therapeutics 2004; 3: 839-847.
21. Miyata Y, Sato T, Imada K, Dobashi A, Yano M and Ito A. A citrus polymethoxyflavonoid, nobiletin, is a novel MEK inhibitor that exhibits antitumor metastasis in human fibrosarcoma HT-1080 cells. Biochemical and Biophysical Research Communications 2008; 366: 168-173.
22. Mulvihill EE, Assini JM, Lee JK, Allister EM, Sutherland BG, Koppes JB, Sawyez CG, Edwards JY, Telford DE, Charbonneau A, St-Pierre P, Marette A and Huff MW. Nobiletin attenuates VLDL overproduction, dyslipidemia, and atherosclerosis in mice with diet-induced insulin resistance. Diabetes 2011; 60: 1446-1457.
23. Murakami A, Kuwahara S, Takahashi Y, Ito C, Furukawa H, Ju-Ichi M, Koshimizu K and Ohigashi H. Bioscience, Biotechnology, and Biochemistry 2001; 65: 194-197.
24. Murakami A, Song M, Katsumata S, Uehara M, Suzuki K and Ohigashi H. Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1J mice: possible involvement of receptor activator of NF-kappaβ ligand (RANKL)-induced osteoclastogenesis regulation. Biofactors 2007; 30: 179-192.
25. Nagase H, Omae N, Omori A, Nakagawasai O, Tadano T, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T and Ohizumi Y. Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities. Biochemical and Biophysical Research Communications 2005a; 337: 1330-1336.
26. Nagase H, Yamakuni T, Matsuzaki K, Maruyama Y, Kasahara J, Hinohara Y, Kondo S, Mimaki Y, Sashida Y, Tank AW, Fukunaga K and Ohizumi Y. Mechanism of neurotrophic action of nobiletin in PC12D cells. Biochemistry 2005b; 44: 13683-13691.
27. Nakajima A, Yamakuni T, Haraguchi M, Omae N, Song SY, Kato C, Nakagawasai O, Tadano T, Yokosuka A, Mimaki Y, Sashida Y and Ohizumi Y. Nobiletin, a citrus flavonoid that improves memory impairment, rescues bulbectomy-induced cholinergic neurodegeneration in mice. Journal of Pharmacology Sciences 2007a; 105: 122-126.
28. Nakajima A, Yamakuni T, Matsuzaki K, Nakata N, Onozuka H, Yokosuka A, Sashida Y, Mimaki Y and Ohizumi Y. Nobiletin, a citrus flavonoid, reverses learning impairment associated with N-methyl- d-aspartate receptor antagonism by activation of extracellular signal-regulated kinase signaling. Journal of Pharmacology and Experimental Therapeutics 2007b; 321: 784-790.
29. Onozuka H, Nakajima A, Matsuzaki K, Shin RW, Ogino K, Saigusa D, Tetsu N, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T and Ohizumi Y. Nobiletin, a citrus flavonoid, improves memory impairment and Abeta pathology in a transgenic mouse model of Alzheimer's disease. Journal of Pharmacology and Experimental Therapeutics 2008; 326: 739-744.
30. Sato T, Koike L, Miyata Y, Hirata M, Mimaki Y, Sashida Y, Yano M and Ito A. Inhibition of activator protein-1 binding activity and phosphatidylinositol 3-kinase pathway by nobiletin, a polymethoxy flavonoid, results in augmentation of tissue inhibitor of metalloproteinases-1 production and suppression of production of matrix metalloproteinases-1 and -9 in human fibrosarcoma HT-1080 cells. Cancer Research 2002; 62: 1025-1029.
31. US DHHS, FDA and CDER. Guidance for Industry: Bioanalytical Method Validation. US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research and Center for Veterinary Medicine, 2001. Available at: http://www/fda.gov/cder/ guidance/index.htm
32. Yasuda T, Yoshimura Y, Yabuki H, Nakazawa T, Ohsawa K, Mimaki Y and Sashida Y. Urinary metabolites of nobiletin orally administered to rats. Chemical and Pharmaceutical Bulletin 2003; 51: 1426-1428.