Metabolism of (2S)-pterosin A: Identification of the phase I and phase II metabolites in rat urine

Drug Metabolism and Disposition

Volumn 40, Issue 8, 2012, Pages 1566-1574

  Lee, Yung Ping ^a   Hsu, Feng Lin ^b   Kang, Jaw Jou ^a   Chen, Chien Kuang ^a   Lee, Shoei Sheng ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b TAIPEI MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

14 O GLUCURONYLPTEROSIN A; 2 HYDROXYMETHYLPTEROSIN E; ANTIDIABETIC AGENT; DRUG METABOLITE; PTEROSIN A; PTEROSIN E; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DECARBOXYLATION; DRUG EXCRETION; DRUG GLUCURONIDATION; DRUG METABOLISM; DRUG STRUCTURE; LACTONIZATION; MALE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT; URINE;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDANS; MAGNETIC RESONANCE SPECTROSCOPY; RATS; SESQUITERPENES;

RATTUS;

EID: 84863918839     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.045039     Document Type: Article

References (31)

1. Boyd GW, Young RJ, Harvey RG, Coombs MM, and Ioannides C (1993) The metabolism and activation of 15,16-dihydrocyclopenta[a]phenanthren-17-one by cytochrome P-450 proteins. Eur J Pharmacol 228:275-282.
2. De Brant V and Remon JP (1991) A simple method for the intragastic administration of drugs to fully conscious guinea pigs. Lab Anim 25:308-309.
3. Brunel P, Hornych A, Guyene TT, Sioufi A, Turri M, and Ménard J (1995) Renal and endocrine effects of flosulide, after single and repeated administration to healthy volunteers. Eur J Clin Pharmacol 49:193-201.
4. Burton KI, Everett JR, Newman MJ, Pullen FS, Richards DS, and Swanson AG (1997) On-line liquid chromatography coupled with high field NMR and mass spectrometry (LC-NMR-MS): a new technique for drug metabolite structure elucidation. J Pharm Biomed Anal 15:1903-1912.
5. Castillo UF, Wilkins AL, Lauren DR, Smith BL, and Alonso-Amelot M (2003) Pteroside A2-a new illudane-type sesquiterpene glucoside from pteridium caudatum L. Maxon, and the spectrometric characterization of caudatodienone. J Agric Food Chem 51:2559-2564.
6. Chen YH, Chang FR, Lu MC, Hsieh PW, Wu MJ, Du YC, and Wu YC (2008) New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis Burm. Molecules 13:255-266.
7. Coombs MM, Russell JC, Jones JR, and Ribeiro O (1985) A comparative examination of the in vitro metabolism of five cyclopenta[a]phenathrenes of varying carcinogenic potential. Carcinogenesis 6:1217-1222.
8. Fukuoka M, Kuroyanagi M, Toyama M, Yoshihira K, and Natori S (1972) Pterosins K, J, and L and six acylated pterosins from bracken, Pteridium-aquilinum var Latiusculum. Chem Pharm Bull 20:2282-2285.
9. Fukuoka M, Kuroyanagi M, Yoshihira K, and Natori S (1978) Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum II. Structures of pterosins, sesquiterpenes having 1-indanone skeleton. Chem Pharm Bull 26:2365-2385.
10. Fukuoka M, Yoshihira K, Natori S, Mihashi K, and Nishi M (1983) Carbon-13 nuclear magnetic resonance spectra of pterosin-sesquiterpenes and related indan-1-one derivatives. Chem Pharm Bull 31:3113-3128.
11. Godejohann M, Tseng LH, Braumann U, Fuchser J, and Spraul M (2004) Characterization of a paracetamol metabolite using on-line LC-SPE-NMR-MS and a cryogenic NMR probe. J Chromatogr A 1058:191-196.
12. House HO (1972) Modern Synthetic Reactions, 2nd ed, p. 511, in the organic chemistry monograph series (Ronald Breslow ed). W.A. Benjamin, Inc., Menlo Park, CA.
13. Hsu FL, Liu SH, and Uang BJ (2010) inventors; Taipei Medical University, National Taiwan University, National Tsing Hua University, and DCB-USA LLC, assignee. Use of pterosin compounds for treating diabetes and obesity. Taiwan Patent No. TW201039836. 2010 July 29.
14. Kuroyanagi M, Fukuoka M, Yoshihira K, and Natori S (1979a) Circular dichroism and conformations of pterosins, 1-indanone derivatives from bracken. Chem Pharm Bull 27:731-741.
15. Kuroyanagi M, Fukuoka M, Yoshihira K, and Natori S (1979b) Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. III. Further characterization of pterosins and pterosides, sesquiterpenes and the glucosides having 1-indanone skeleton from the rhizomes. Chem Pharm Bull 27:592-601.
16. Lai YC, Kuo TF, Chen CK, Tsai HJ, and Lee SS (2010) Metabolism of dicentrine: identification of the phase I and phase II metabolites in miniature pig urine. Drug Metab Dispos 38:1714-1722.
17. Lam SH, Wang CY, Chen CK, and Lee SS (2007) Chemical investigation of Phyllanthus reticulatus by HPLC-SPE-NMR and conventional methods. Phytochem Anal 18:251-255.
18. Lee SS, Lai YC, Chen CK, Tseng LH, and Wang CY (2007) Characterization of isoquinoline alkaloids from Neolitsea sericea var. aurata by HPLC-SPE-NMR. J Nat Prod 70:637-642.
19. Lioi MB, Barbieri R, Borzacchiello G, Dezzi S, Roperto S, Santoro A, Russo V, and Roperto F (2004) Chromosome aberrations in cattle with chronic enzootic haematuria. J Comp Pathol 131:233-236.
20. Ojika M, Sugimoto K, Okazaki T, and Yamada K (1989) Modification and cleavage of DNA by ptaquiloside. A new potent carcinogen isolated from bracken fern. J Chem Soc Chem Commun 22:1775-1777.
21. Ouyang DW, Ni X, Xu HY, Chen J, Yang PM, and Kong DY (2010) Pterosins from Pteris multifida. Planta Med 76:1896-1900.
22. Pamukcu AM, Price JM, and Bryan GT (1976) Naturally occurring and braken-fern-induced bovine urinary bladder tumors. Clinical and morphological characteristics. Vet Pathol 13:110-122.
23. Sandvoss M, Bardsley B, Beck TL, Lee-Smith E, North SE, Moore PJ, Edwards AJ, and Smith RJ (2005) HPLC-SPE-NMR in pharmaceutical development: capabilities and applications. Magn Reson Chem 43:762-770.
24. Sengupta P, Sen M, and Niyogi SK (1976) Isolation and structure of wallichoside, a novel pteroside from Pteris wallichiana. Phytochemistry 15:995-998.
25. Spraul M, Freund AS, Nast RE, Withers RS, Maas WE, and Corcoran O (2003) Advancing NMR sensitivity for LC-NMR-MS using a cryoflow probe: application to the analysis of acetaminophen metabolites in urine. Anal Chem 75:1536-1541.
26. Wang CY and Lee SS (2005) Analysis and identification of lignans in Phyllanthus urinaria by HPLC-SPE-NMR. Phytochem Anal 16:120-126.
27. Wu Z (1990) XinHuaBenCaoGangYao, Vol. 3, p. 654, Shanghai Press of Science and Technology, Shanghai.
28. Yi P, Hadden C, Kulanthaivel P, Calvert N, Annes W, Brown T, Barbuch RJ, Chaudhary A, Ayan-Oshodi MA, and Ring BJ (2010) Disposition and metabolism of semagacestat, a {gamma}-secretase inhibitor, in humans. Drug Metab Dispos 38:554-565.
29. Yoo HH, Chung HJ, Lee J, Lee CS, Kang MJ, and Kim DH (2008) Enzymatic C-demethylation of 1-[2-(5-tert-butyl-[1,3,4]oxadiazole-2-carbonyl)-4-fluoro- pyrrolidin-1-yl]-2-(2-hydroxy-1,1-dimethylethylamino)-ethanone (LC15-0133) in rat liver. Drug Metab Dispos 36:485-489.
30. Yoshihira K, Fukuoka M, Kuroyanagi M, and Natori S (1971) 1-Indanone derivatives from bracken, Pteridium aquilinum var. latiusculum. Chem Pharm Bull 19:1491-1495.
31. Yoshihira K, Fukuoka M, Kuroyanagi M, Natori S, Umeda M, Morohoshi T, Enomoto M, and Saito M (1978) Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. 1. Introduction, extraction and fractionation of constituents, and toxicological studies including carcinogenicity tests. Chem Pharm Bull 26:2346-2364.