Enantiospecific Analysis of 8-Prenylnaringenin in Biological Fluids by Liquid-Chromatography-Electrospray Ionization Mass Spectrometry: Application to Preclinical Pharmacokinetic Investigations

Chirality

Volumn 26, Issue 8, 2014, Pages 419-426

  Martinez, Stephanie E ^a   Lakowski, Ted M ^a   Davies, Neal M ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

8 Prenylnaringein; analysis; chiral; enantioseparation; enantiospecific; flavonoid; Humulus lupulus L; LC MS; phytoestrogen; preclinical pharmacokinetics

Indexed keywords

2 PROPANOL; 8 PRENYLNARINGENIN; AMMONIUM FORMATE; CARBAMAZEPINE; 8-PRENYLNARINGENIN; FLAVANONE DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; BLOOD SAMPLING; BODY FLUID; CALIBRATION; CIRCULAR DICHROISM; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DECOMPOSITION; DRUG DETERMINATION; DRUG DISPOSITION; DRUG HALF LIFE; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; ENANTIOSELECTIVITY; HUMULUS LUPULUS; ION MONITORING; KIDNEY CLEARANCE; KIDNEY CONCENTRATING CAPACITY; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; LIVER CLEARANCE; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; URINALYSIS; ANIMAL; BLOOD; BLOOD ANALYSIS; CHEMISTRY; LIMIT OF DETECTION; PROCEDURES; STATISTICAL MODEL; STEREOISOMERISM; URINE;

ANIMALS; BLOOD CHEMICAL ANALYSIS; CHROMATOGRAPHY, LIQUID; DRUG STABILITY; FLAVANONES; LIMIT OF DETECTION; LINEAR MODELS; MALE; RATS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; URINALYSIS;

EID: 84904786303     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22343     Document Type: Article

References (60)

1. Stevens JF, Ivancic M, Hsu VL, Deinzer ML,. Prenylflavonoids from Humulus lupulus. Phytochemistry 1997; 44: 1575-1585. (Pubitemid 27142313)
2. Milligan SR, Kalita JC, Heyerick A, Rong H, De Cooman L, De Keukeleire D,. Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J Clin Endocrinol Metab 1999; 83: 2249-2252. (Pubitemid 30647064)
3. Matsuo K, Ito M, Honda G, Qui KT, Kiuchi F,. Trypanocidal flavonoids from Sophora flavescens. Nat Med 2003; 57: 253-255. (Pubitemid 38186136)
4. Zhang Y, Zhang P, Cheng Y,. Structural characterization of isoprenylated flavonoids from Kushen by electrospray ionization multistage tandem mass spectrometry. J Mass Spectrom 2008; 43: 1421-1431.
5. Komatsu M, Yokoe I, Shirataki Y,. Studies on the constituents of Sophora species. XII. Constituents of the aerial parts of Sophora tomentosa L. Chem Pharm Bull 1978; 26: 1274-1278.
6. Komatsu M, Yokoe I, Shirataki Y,. Studies on the constituents of Sophora species. XIII. Constituents of the aerial parts of Sophora tomentosa L. Chem Pharm Bull 1978; 26: 3863-3870. (Pubitemid 9109358)
7. Tanaka T, Iinuma M, Asai F, Ohyama M, Burandt CL,. Flavonoids from the root and stem of Sophora tomentos. Phytochemistry 1997; 46: 1431-1437. (Pubitemid 28005392)
8. Shirataki Y, Yokoe I, Noguchi M, Tomimori T, Komatsu M,. Studies on the constituents of Sophora species. XXII. Constituents of the root of Sophora moorcroftiana benth. ex Baker. Chem Pharm Bull 1988; 36: 2220-2225.
9. Kitaoka M, Kadokawa H, Sugano M, Ichikawa K, Taki M, Takaish S, Iijima Y, Tsutsumi S, Boriboon M, Akiyama T,. Prenylflavonoids: A new class of non-steroidal phytoestrogen. (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure-activity relationship. Planta Med 1998; 64: 511-515. (Pubitemid 28383882)
10. Fukai T, Cai B-S, Maruno K, Miyakawa Y, Konishi M, Nomura T,. An isoprenylated flavanone from Glycyrrhiza glabra and rec-assay of licorice phenols. Phytochemistry 1998; 49: 2005-2013. (Pubitemid 28563811)
11. Jang DS, Cuendet M, Hawthorne ME, Kardono LBS, Kawanishi K, Fong HHS, Mehta RG, Pezzuto JM, Knghorn AD,. Prenylated flavonoids of the leaves of Macaranga conifera with inhibitory activity against cyclooxygenase-2. Phytochemistry 2002; 61: 867-872. (Pubitemid 35439923)
12. Versiani MA, Diyabalanage T, Ratnayake R, Henrich CJ, Bates SE, McMahon JB, Gustafson KR,. Flavonoids from eight tropical plant species that inhibit the multidrug resistance transporter ABCG2. J Nat Prod 2011; 74: 262-266.
13. Sasaki H, Kashiwada Y, Shibata H, Takaishi Y,. Prenylated flavonoids from Desmodium caudatum and evaluation of their anti-MRSA activity. Phytochemistry 2012; 82: 136-142.
14. Nakahara K, Roy MK, Ono H, Maeda I, Trakoontivakorn G,. Prenylated flavanones isolated from flowers of Azadirachta indica (the neem tree) as antimutagenic constituents against heterocyclin amines. J Agric Food Chem 2003; 51: 6456-6460.
15. Ito C, Mizuno T, Matsuoka M, Kumura Y, Sato K, Kajiura I, Huybrechts I, Omura M, Ju-Ichi M, Furukawa H,. A new flavonoid and other new components from citrus plants. Chem Pharm Bull 1988; 36: 3292-3295.
16. Auzi AA, Harley TG, Waterman PG,. Distribution of Flavonoids, Alkaloids, Acetophenones and Phloroglucinols in the Genus Bosistoa (Rutaceae). Biochem Syst Ecol. 1997; 25: 611-617. (Pubitemid 27481250)
17. Bohlmann F, Zdero C, King RM, Robinson H,. New prenylflavanoids from Marshallia grandiflora. Phytochemistry 1979; 18: 1246-1247.
18. Bohlmann F, Zdero C, Robinson H, King RM,. A diterpene, a sesquiterpene qunone and flavanones from Wyethia helenioides. Phytochemistry 1981; 20: 2245-2248.
19. McCormick S, Robson K, Bohm B,. Flavonoids from Wyethia glabra. Phytochemistry 1985; 24: 1614-1616.
20. McCormick S, Robson K, Bohm B,. Flavonoids of Wyethia angustrifolia and W. helenioides. Phytochemistry 1986; 25: 1986.
21. McCormick S, Robson K, Bohm B,. Flavonoids of Wyethia section agnorhiza. Phytochemistry 1987; 26: 2421-2422.
22. Bohlmann F, Ates N,. Three prenylated flavonoids from Helichrysum athrixiifolium. Phytochemistry 1984; 23: 1338-1339.
23. Cano A, Espinoza M, Ramos C, Delgado G,. New prenylated flavanones from Esenbeckia berlandieri ssp. acapulcensis. J Mex Chem Soc 2006; 50: 71-75.
24. Lukaseder B, Vajrodaya S, Hehenberger T, Seger C, Nagl M, Lutz-Kutschera G, Robien W, Greger H, Hofer O,. Prenylated flavanones and flavanonols as chemical markers in Glycosmis species (Rutaceae). Phytochemistry 2009; 70: 1030-1037.
25. Miron T, Plaza M, Bahrim G, Ibáñez E, Herrero M,. Chemical composition of bioactive pressurized extracts of Romanian aromatic plants. J Chromatogr A 2011; 1218: 4918-4927.
26. Stevens JF, Page JE,. Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Phytochemistry 2004; 65: 1317-1330. (Pubitemid 38844716)
27. Stevens JF, Taylor AW, Deinzer ML,. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatogrpahy-tandem mass spectrometry. J Chromatogr A 1999; 832: 97-107. (Pubitemid 29073728)
28. Tekel J, De Keukeleire D, Rong H, Daeseleire E, Van Peteghem C,. Determination of the hop-derived phytoestrogen 8-prenylnaringenin, in beer by gas chromatogrpahy/mass spectrometry. J Agric Food Chem 1999; 47: 5059-5063. (Pubitemid 30016938)
29. Rong H, Zhao Y, Lazou K, De Keukeleire D, Milligan SR, Sandra P,. Quantitation of 8-prenylnaringenin, a novel phytoestrogen in hops (Humulus lupulus L.), hop products, and beers, by benchtop HPLC-MS using electrospray ionization. Chromatogrpahia 2000; 51: 545-552. (Pubitemid 30353201)
30. Maragou NC, Rosenberg E, Thomaidis NS, Koupparis MA,. Direct determination of the estrogenic compounds 8-prenylnaringenin, zearalenone, alpha- and beta-zearalenol in beer by liquid chromatography-mass spectrometry. J Chromatogr A 2008; 1202: 47-57.
31. Ceslová L, Holcapek M, Fidler M, Drsticková J, Lísa M,. Characterization of prenylflavonoids and hop bitter acids in various classes of Czech beers and hop extracts using high-performance liquid chromatography-mass spectrometry. J Chromatogr A 2009; 1216: 7249-57.
32. Mudura E, Paucean A, Tofana M, Socaci S,. The evaluation of prenylflavonoids compounds in Romanian beer. Bull Univ Agric Sci Vet Med Cluj-Napoca Agric 2011; 68: 333-338.
33. Intelmann D, Haseleu G, Dunkel A, Lagemann A, Stephan A, Hofmann T,. Comprehensive sensomics analysis of hop-derived bitter compounds during storage of beer. J Agric Food Chem 2011; 59: 1939-1053.
34. Possemiers S, Heyerick A, Robbens V, De Keukeleire D, Verstraete W,. Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin. J Agric Food Chem 2005; 53: 6281-6288. (Pubitemid 41169374)
35. Possemiers S, Bolca S, Grootaert C, Heyerick A, Decroos K, Dhooge W, De Keukeleire D, Rabot S, Verstraete W, Van der Wiele T,. The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine. J Nutr 2006; 136: 1862-1867. (Pubitemid 43973589)
36. Possemiers S, Rabot S, Espín JC, Bruneau A, Philippe C, González-Sarrías A, Heyerick A, Tomás-Barberán FA, De Keukeleire D, Verstraete W,. Eubacterium Limosum activates isoxanthohumol from hops (Humulus lupulus L.) into the potent phytoestrogen 8-prenylnaringenin in vitro and in rat intestine. J Nutr 2008; 138: 1310-1316. (Pubitemid 351930995)
37. Bolca S, Possemiers S, Verstraete W, Van de Wiele T, Heyerick A, De Keukeleire D, Huybrechts I, De Henauw S, Depypere H, Bracke M,. Microbial and dietary factors associated with the equol and 8-prenylnaringenin producer phenotypes. Acta Hortic 2009; 848: 235-246.
38. Hanske L, Loh G, Sczensy S, Blaut M, Braune A,. Recovery and metabolism of xanthohumol in germ-gree and human microbiota-associated rats. Mol Nutr Food Res 2010; 54: 1405-1413.
39. Guo J, Nikolic D, Chadwick LR, Pauli GF, van Breeman RB,. Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.). Drug Metab Dispos 2006; 34: 1152-1159.
40. Keiler AM, Zierau O, Kretzschmar G,. Hop extracts and hop substances in treatment of menopause complaints. Planta Med 2013; 79: 576-579.
41. Schiller H, Forster A, Vonhoff C, Hegger M, Biller A, Winterhoff H,. Sedating effects of Humulus lupulus L. extracts. Phytomedicine 2006; 13: 535-541.
42. Coldham N, Sauer M,. Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement. Food Chem Toxicol 2001; 39: 1211-1224. (Pubitemid 33030233)
43. Cornu C, Remontet L, Noel-Baron F, Nicolas A, Feugier-Favier N, Roy P, l Claustrat B, Saadatian-Elahi M, Kassaï B,. A dietary supplement to improve the quality of sleep: a randomized placebo controlled trial. BMC Complement Altern Med 2010; 10: 29.
44. Chen W, Becker T, Qian F, Ring J,. Beer and beer compounds: physiological effects on skin health. J Eur Acad Dermatol Venereol 2013; 28: 142-150.
45. Milligan S, Kalita J, Pocock V, Heyerick A, De Cooman L, Rong H, De Keukeleire D,. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction 2002; 123: 235-242. (Pubitemid 34144673)
46. Schaefer O, Humpel M, Fritzemeir K, Bohlmann R, Schleuning D,. 8-Prenylnaringenin is a potent ERalpha selective phytoestrogen present in hops and beer. J Steroid Biochem Mol Biol 2003; 84: 359-360. (Pubitemid 36514851)
47. Yáñez JA, Andrews PK, Davies NM,. Methods of analysis and separation of chiral flavonoids. J Chromatogrpahy B 2007; 848: 159-181. (Pubitemid 46453303)
48. Shah RR, Midgley JM, Branch SK,. Stereochemical origin of some clinically significant drug safety concerns: lessons for future drug development. Adverse Drug React Toxicol Rev 1998; 17: 145-190. (Pubitemid 28508604)
49. Hutt AJ,. Chirality and pharmacokinetics: an area of neglected dimensionality? Drug Metabol Drug Interact 2007; 17: 79-112. (Pubitemid 47215866)
50. Nikolic̈ D, van Breemen RB,. Analytical methods for quantitation of prenylated flavonoids from hops. Curr Anal Chem 2013; 9: 71-85.
51. Kodama S, Kemmel T, Yamashita T, Takayanagi N,. Enantioseparation of 8-prenylnaringenin, a phytoestrogen, by hydroxypropyl-γ-cyclodextrin- modified micellar electrokinetic chromatographic method. Toyama-ken Eisei Kenkyusho Nenpo 2008; 31: 185-186.
52. Rad M, Hümpel M, Schaefer O, Schoemaker RC, Schleuning WD, Cohen AF, Burggraaf J,. Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral dose to postmenopausal women. Br J Pharmacol. 2006; 62: 288-296. (Pubitemid 44215528)
53. Gaffield W,. Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides. Tetrahedron 1970; 26: 4093-4108.
54. Yang C, Tsai S, Chao PLEE, Yen H, Chien T, Hsiu S,. Determination of hesperetin and its conjugate metabolites in serum and urine. J Food Drug Anal. 2002; 10: 143-148. (Pubitemid 35355989)
55. Roupe K, Remsberg CM, Yáñez J, Davies NM,. Pharmacometrics of stilbenes: seguing towards the clinic. Curr Clin Pharmacol 2006; 1: 81-101.
56. Roupe KA, Yáñez JA, Teng XW, Davies NM,. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. J Pharm Pharmacol 2006; 58: 1443-50. (Pubitemid 44785532)
57. Charles River Laboratories International. Vascular catheterizations: handling instructions; 2012: 1-2. Available at: http://www.criver.com/files/ pdfs/surgery/ss-r-vascular-catheterizations-handling.aspx.
58. Hansel R, Shultz J,. Desmethylxanthohumol: Isolierung aus Hopfen und Cyclisierung zu Flavanonen. Arch Pharm (Weinheim) 1988; 321: 37-40.
59. Quifer-Rada P, Martínez-Huélamo M, Jáuregui O, Chiva-Blanch G, Estruch R, Lamuela-Raventõs R,. Analytical condition setting a crucial step in the quantification of unstable polyphenols in acidic conditions: analyzing prenyl flavanoids in biological samples by liquid chromatography - electrospray ionization triple quadruple mass spectrometry. Anal Chem. 2013; 85: 5547-54.
60. Gerlowski LE, Jain RK,. Physiologically based pharmacokinetic modeling: principles and applications. J Pharm Sci. 1983; 72: 1103-1127. (Pubitemid 13013622)