Quantitative analysis of hydroxylated polymethoxyflavones by high-performance liquid chromatography

Biomedical Chromatography

Volumn 24, Issue 8, 2010, Pages 838-845

  Li, Shiming ^a   Wang, Yu ^b   Wang, Zhenyu ^c   Xiao, Hang ^d   Lo, Chih Yu ^e   Rawson, Nancy ^a   Ho, Chi Tang ^b  

^a WellGen Inc ^*  (United States)

^b RUTGERS UNIVERSITY   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

^d UNIVERSITY OF MASSACHUSETTS   (United States)

^e NATIONAL CHIAYI UNIVERSITY   (Taiwan)

Author keywords

High performance liquid chromatography; Hydroxylated polymethoxyflavones; Orange peel extracts; Polymethoxyflavones

Indexed keywords

CITRUS FRUITS; HYDROXYLATION; MAMMALS; QUALITY CONTROL; RESEARCH LABORATORIES;

ANTI-INFLAMMATORY ACTIVITY; CITRUS PEEL; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATED POLYMETHOXYFLAVONE; NUTRACEUTICALS; ORANGE PEEL EXTRACT; ORANGE PEELS; POLYMETHOXYFLAVONES; POTENT ACTIVITY;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

5 HYDROXY 3,6,7,3',4' PENTAMETHOXYFLAVONE; 5 HYDROXY 3,6,7,8,3',4' HEXAMETHOXYFLAVONE; 5 HYDROXY 6,7,4' TRIMETHOXYFLAVONE; 5 NORNOBILETIN; 5 NORSINESETIN; 5 NORTANGERETIN; FLAVONE DERIVATIVE; POLYMETHOXYFLAVONE; UNCLASSIFIED DRUG; FLAVONOID; PLANT EXTRACT;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CITRUS FRUIT; DRUG ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; NONHUMAN; ORANGE (FRUIT); QUANTITATIVE ANALYSIS; ULTRAVIOLET RADIATION; CHEMISTRY; EVALUATION STUDY; PROCEDURES; SWEET ORANGE;

CITRUS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS SINENSIS; FLAVONOIDS; HYDROXYLATION; PLANT EXTRACTS;

EID: 77954711218     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1372     Document Type: Article

References (25)

1. Bianchini JP and Gaydou EM. Separation of polymethoxylated flavones by straight-phase high-performance liquid chromatography. Journal of Chromatography 1980; 190: 233.
2. Bianchini JP, Gaydou EM, Siouffi AM, Mazerolles G, Mathieu D and Phan Tan Luu R. Optimization of the separation of polymethoxylated flavones in reversed phase liquid chromatography. Chromatographia 1987; 23: 15.
3. Bovicelli P, D'Angelo V, Collalto D, Verzina A, D'Antona N and Lambusta D. Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones. Journal of Pharmacy and Pharmacology 2007; 59(12): 1697.
4. Dandan W, Jian W, Xuehui H, Ying Y and Kunyi N. Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques. Journal of Pharmaceutical and Biomedical Analysis 2007; 44: 63.
5. Dugo P, Mondello L, Dugo G, Heaton DM, Bartle KD, Clifford AA and Myers PJ. Rapid analysis of polymethoxylated flavones from citrus oil by supercritical fluid chromatography. Agriculture and Food. Chemistry 1996; 44: 3900.
6. Heimhuber B, Galensa R and Herrmann KJ. High-performance liquid chromatographic determination of polymethoxylated flavones in orange juice after solid-phase extraction Chromatography 1988; 439: 481.
7. Hirata T, Fujii M, Akita K, Yanaka N, Ogawa K, Kuroyanagi M and Hongo D. Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer. Bioorganic and Medical Chemistry 2009; 17: 25.
8. ICH, International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH) Q2(R1): Validation of Analytical Procedures: Text and Methodology, 2005.
9. Lai CS, Li S, Chai CY, Lo CY, Ho CT, Wang YJ and Pan MH. Inhibitory effect of citrus 5-hydroxy-3,6,7,8,3′,4′-hexamethoxyflavone on 12-Otetradecanoylphorbol 13-acetate-induced skin inflammation and tumor promotion in mice. Carcinogenesis 2007; 28: 2581.
10. Lai CS, Li S, Chai CY, Lo CY, Dushenkov S, Ho CT, Pan MH and Wang YJ. Anti-inflammatory and antitumor promotional effects of a novel urinary metabolite, 3′,4′-didemethylnobiletin, derived from nobiletin. Carcinogenesis 2008; 29: 2415.
11. Li S, Lo CY and Ho CT. Hydroxylated polymethoxyflavones and methylated flavonoids in sweet orange (Citrus sinensis) peel. Journal of Agriculture and Food Chemistry 2006a; 20: 133.
12. Li S, Wang Z, Sang S, Huang MT and Ho CT. Identification of nobiletin metabolites in mouse urine. Molecular Nutrition and Food Research 2006b; 50: 291.
13. Li S, Pan MH, Lai CS, Lo CY, Dushenkov S and Ho CT. Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines. Bioorganic and Medical Chemistry 2007a; 15: 3381. (Pubitemid 46529267)
14. Li S, Sang S, Pan MH, Lai CS, Lo CY, Yang CS and Ho CT. Anti-inflammatory property of nobiletin metabolites in mouse urine. Bioorganic and Medical Chemistry Letters 2007b; 17: 5177. (Pubitemid 47259653)
15. Li S, Pan MH, Lo CY, Tan D, Wang Y, Shahidi F and Ho CT. Chemistry and health effects of polymethoxyflavones and hydroxylated polymethoxyfl avones. Journal of Functional Foods 2009; 1: 2.
16. Manthey JA and Buslig BS. HPLC-MS analysis of methoxylated flavanones in orange oil residue. Proceedings of Florida State Horticultural Society 2003; 116: 410.
17. Morin P, Gallois A and Richard H. Fast separation of polymethoxylated flavones by carbon dioxide supercritical fluid chromatography. Journal of Chromatography 1991; 586: 171.
18. Okuno Y and Miyazawa M. Apoptosis-inducing activity of hydroxylated polymethoxyflavones and polymethoxyflavones from orange peel in human breast cancer cells. Journal of Natural Products 2004; 67: 1876.
19. 2+-mediated apoptosis in breast cancer cells. Life Science 2005; 80: 245.
20. Sergeev IN, Ho CT, Li S, Colby J and Dushenkov S. Apoptosis-inducing activity of hydroxylated polymethoxyflavones and polymethoxyflavones from orange peel in human breast cancer cells. Molecular Nutrition and Food Research 2007; 51: 1478.
21. Stremple P. GC/MS analysis of polymethoxyflavones in citrus oil. Journal of High Resolution Chromatgraphy 1998; 21: 587. (Pubitemid 28535572)
22. Tsukayama M, Kusunoki E, Hossain MM, Kawamura Y and Hayashi Y. Microwave-assisted efficient synthesis of polymethoxyacetophenones and natural polymethoxyflavones, and their inhibitory effects on melanogenesis. Heterocycles 2007; 71: 1589.
23. Wang Z, Li S, Ferguson S, Goodnow R and Ho CT. Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts. Journal of Separation Science 2008; 31(1): 30. (Pubitemid 351227886)
24. Weber B, Hartmann B, Stockigt D, Schreiber K, Roloff M, Bertram H-J and Schmidt CO. Liquid chromatography/mass spectrometry and liquid chromatography/nuclear magnetic resonance as complementary analytical techniques for unambiguous identification of polymethoxylated flavones in residues from molecular distillation of orange peel oils (Citrus sinensis). Journal of Agriculture and Food Chemistry 2006; 54: 274.
25. Xiao H, Yang CS, Li S, Jin H, Ho CT and Patel T. Monodemethylated polymethoxyfl avones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis. Molecular Nutrition and Food Research 2009; 53, 398.