Identification of known chemicals and their metabolites from Alpinia oxyphylla fruit extract in rat plasma using liquid chromatography/tandem mass spectrometry (LC-MS/MS) with selected reaction monitoring

Journal of Pharmaceutical and Biomedical Analysis

Volumn 97, Issue , 2014, Pages 166-177

  Chen, Feng ^a,b   Li, Hai Long ^a,b   Tan, Yin Feng ^a,b   Li, Yong Hui ^a,b   Lai, Wei Yong ^a,b   Guan, Wei Wei ^a,b   Zhang, Jun Qing ^a,b   Zhao, Yuan Sheng ^c   Qin, Zhen Miao ^a,b  

^a HAINAN MEDICAL UNIVERSITY   (China)

^b Hainan Provincial Key Laboratory of R and D of Tropical Herbs   (China)

^c HAMNER INSTITUTES FOR HEALTH SCIENCES   (United States)

Author keywords

Diarylheptanoids; Flavonoids; LC MS MS; Target analysis; Yizhi extract

Indexed keywords

APIGENIN 4,7 DIMETHYLETHER; CHINESE DRUG; CHRYSIN; DRUG METABOLITE; ESSENTIAL OIL; FLAVONOID; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; HEPTANE DERIVATIVE; IZALPININ; KAEMPFERIDE; METHANOL; MONOGLUCURONIDE; NOOTKATONE; OXIDOREDUCTASE; OXYPHYLLACINOL; PLANT EXTRACT; SESQUITERPENE; SUOQUAN CAPSULE; SUOQUAN PILL; TECTOCHRYSIN; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE; YAKUCHINONE A; YAKUCHINONE B; YIZHI EXTRACT; FRUIT EXTRACT, ALPINIA OXYPHYLLA; PLANT MEDICINAL PRODUCT;

ALPINIA; ALPINIA OXYPHYLLA; ANIMAL EXPERIMENT; ANTIDIARRHEAL ACTIVITY; ARTICLE; BLOOD SAMPLING; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CAPSULE; DRUG HYDROLYSIS; DRUG IDENTIFICATION; DRUG RETENTION; DRUG STRUCTURE; DRUG TRANSFORMATION; FRUIT; LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; PILL; PRECIPITATION; PRIORITY JOURNAL; RAT; TANDEM MASS SPECTROMETRY; TRADITIONAL MEDICINE; ANIMAL; BIOTRANSFORMATION; BLOOD; CHEMISTRY; METABOLISM; ORAL DRUG ADMINISTRATION; PROCEDURES;

ADMINISTRATION, ORAL; ANIMALS; BIOTRANSFORMATION; CHROMATOGRAPHY, LIQUID; MALE; PHYTOCHEMICALS; PLANT EXTRACTS; RATS; TANDEM MASS SPECTROMETRY;

EID: 84901456992     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2014.04.037     Document Type: Article

References (31)

1. Available from: http://www.fda.gov/downloads/drugs/guidancecomplianceregulatoryinformation/guidances/ucm070491.pdf.
2. Chinese Pharmacopoeia Commission, Pharmacopoeia of the People's Republic of China 2010, vol. 1:274. China Medical Science and Technology Press, Beijing.
3. Alpinia oxyphylla. International Collation of Traditional and Folk Medicine: Northeast Asia, Part II 1997, 202-203. World Scientific, Singapore. P.P.H. But, T. Kimura, J.X. Guo, C.K. Sung (Eds.).
4. Lin R.J., Yen C.M., Chou T.H., Chiang F.Y., Wang G.H., Tseng Y.P., Wang L., Huang T.W., Wang H.C., Chan L.P., Ding H.Y., Liang C.H. Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla. BMC Complement. Altern. Med. 2013, 13:237.
5. Chen F., Li H.L., Li Y.H., Tan Y.F., Zhang J.Q. Quantitative analysis of the major constituents in Chinese medicinal preparation SuoQuan formulae by ultra fast high performance liquid chromatography/quadrupole tandem mass spectrometry. Chem. Cent. J. 2013, 7:131.
6. Qiu J. Traditional medicine: a culture in the balance. Nature 2007, 448:126-128.
7. Chun K.S., Kang J.Y., Kimo H., Kang H., Surh Y.J. Effects of yakuchinone A and yakuchinone B on the ester-induced expression of COX-2 and NO and activation of NF-kappa B in mouse skin. J. Environ. Pathol. Toxicol. Oncol. 2002, 21:131-139.
8. Chun K.S., Park K.K., Lee J., Kang M., Surh Y.J. Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae). Oncol. Res. 2002, 13:37-45.
9. Shin T.Y., Won J.H., Kim H.M., Kim S.H. Effect of Alpinia oxyphylla fruit extract on compound 48/80-induced anaphylactic reactions. Am. J. Chin. Med. 2001, 29:293-302.
10. Yamahara J., Li Y.H., Tamai Y. Anti-ulcer effect in rats of bitter cardamom constituents. Chem. Pharm. Bull. 1990, 38:3053-3054.
11. Yu X.Y., An L.J., Wang Y.Q., Zhao H., Gao C.Z. Neuroprotective effect of Alpinia oxyphylla Miq. fruits against glutamate-induced apoptosis in cortical neurons. Toxicol. Lett. 2003, 144:205-212.
12. Zhang Z.J., Cheang L.C., Wang M.W., Li G.H., Chu I.K., Lin Z.X., Lee S.M. Ethanolic extract of fructus Alpinia oxyphylla protects against 6-hydroxydopamine-induced damage of PC12 cells in vitro and dopaminergic neurons in zebrafish. Cell. Mol. Neurobiol. 2012, 32:27-40.
13. Chen F., Li H.L., Tan Y.F., Guan W.W., Zhang J.Q., Li Y.H., Zhao Y.S., Qin Z.M. Different accumulation profiles of multiple components between pericarp and seed of Alpinia oxyphylla capsular fruit as determined by UFLC-MS/MS. Molecules 2014, 19:4510-4523.
14. Li Y.H., Chen F., Wang J.F., Wang Y., Zhang J.Q., Guo T. Analysis of nine compounds from Alpinia oxyphylla fruit at different harvest time using UFLC-MS/MS and an extraction method optimized by orthogonal design. Chem. Cent. J. 2013, 7:134.
15. Zhang J.Q., Wang S., Li Y.H., Xu P., Chen F., Tan Y.F., Duan J.A. Anti-diarrheal constituents of Alpinia oxyphylla. Fitoterapia 2013, 89:149-156.
16. Chen F., Li H.L., Tan Y.F., Guan W.W., Li Y.H., Zhang J.Q. Validated method to measure yakuchinone A in plasma by LC-MS/MS and its application to a pharmacokinetic study in rats. Chem. Cent. J. 2014, 8:2.
17. Lu T., Yang J.L., Gao X.M., Chen P., Du F.F., Sun Y., Wang F.Q., Xu F., Shang H.C., Huang Y.H., Wang Y., Wan R.Z., Liu C.X., Zhang B.L., Li C. Plasma and urinary tanshinol from Salvia miltiorrhiza (Danshen) can be used as pharmacokinetic markers for cardiotonic pills, a cardiovascular herbal medicine. Drug Metab. Dispos. 2008, 36:1578-1586.
18. Liu H.F., Yang J.L., Du F.F., Gao X.M., Ma X.T., Huang Y.H., Xu F., Niu W., Wang F.Q., Mao Y., Sun Y., Lu T., Liu C., Zhang B., Li C. Absorption and disposition of ginsenosides after oral administration of Panax notoginseng extract to rats. Drug Metab. Dispos. 2009, 37:2290-2298.
19. Cheng C., Liu X.W., Du F.F., Li M.J., Xu F., Wang F.Q., Liu Y., Li C., Sun Y. Sensitive assay for measurement of volatile borneol, isoborneol, and the metabolite camphor in rat pharmacokinetic study of Borneolum (Bingpian) and Borneolum syntheticum (synthetic Bingpian). Acta Pharmacol. Sin. 2013, 34:1337-1348.
20. Zhao Y., Sun Y., Li C. Simultaneous determination of ginkgo flavonoids and terpenoids in plasma: ammonium formate in LC mobile phase enhancing electrospray ionization efficiency and capacity. J. Am. Soc. Mass Spectrom. 2008, 19:445-449.
21. Chen F., Li L., Xu F., Sun Y., Du F.F., Ma X.T., Zhong C.C., Li X.X., Wang F.Q., Zhang N.T., Li C. Systemic and cerebral exposure to and pharmacokinetics of flavonols and terpene lactones after dosing standardized Ginkgo biloba leaf extracts to rats via different routes of administration. Br. J. Pharmacol. 2013, 170:440-457.
22. Shia C.S., Hou Y.C., TsaiY.S.Y., Huieh P.H., Leu Y.L., Chao P.D. Differences in pharmacokinetics and ex vivo antioxidant activity following intravenous and oral administrations of emodin to rats. J. Pharm. Sci. 2010, 99:2185-2195.
23. Sharma R.A., Gescher A.J., Steward W.P. Curcumin: the story so far. Eur. J. Cancer 2005, 41:1955-1968.
24. Griffiths L.A., Smith G.E. Metabolism of apigenin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro. Biochem. J. 1972, 128:901-911.
25. De Santi C., Pietrabissa A., Spisni R., Mosca F., Pacifici G.M. Sulphation of resveratrol, a natural compound present in wine, and its inhibition by natural flavonoids. Xenobiotica 2000, 30:857-866.
26. Walle U.K., Galijatovic A., Walle T. Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2. Biochem. Pharmacol. 1999, 58:431-438.
27. Ung D., Nagar S. Variable sulfation of dietary polyphenols by recombinant human sulfotransferase (SULT) 1A1 genetic variants and SULT1E1. Drug Metab. Dispos. 2007, 35:740-746.
28. Galijatovic A., Otake Y., Walle U.K., Walle T. Extensive metabolism of the flavonoid chrysin by human Caco-2 and Hep G2 cells. Xenobiotica 1999, 29:1241-1256.
29. Pan M.H., Huang T.M., Lin J.K. Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab. Dispos. 1999, 27:486-494.
30. Ireson C., Orr S., Jones D.J., Verschoyle R., Lim C.K., Luo J.L., Howells L., Plummer S., Jukes R., Williams M., Steward W.P., Gescher A. Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Cancer Res. 2001, 61:1058-1064.
31. Ireson C.R., Jones D.J., Orr S., Coughtrie M.W., Boocock D.J., Williams M.L., Farmer P.B., Steward W.P., Gescher A.J. Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol. Biomarkers Prev. 2002, 11:105-111.