Metabolism of saikosaponin a in rats: Diverse oxidations on the aglycone moiety in liver and intestine in addition to hydrolysis of glycosidic bondss

Drug Metabolism and Disposition

Volumn 41, Issue 3, 2013, Pages 622-633

  Liu, Guoqiang ^a   Tian, Yuan ^a   Li, Geng ^a   Xu, Lei ^a   Song, Rui ^a   Zhang, Zunjian ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; DRUG METABOLITE; PROSAIKOGENIN F; SAIKOGENIN F; SAIKOSAPONIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CARBOXYLATION; CONTROLLED STUDY; DEHYDROGENATION; DRUG BILE LEVEL; DRUG BLOOD LEVEL; DRUG DISPOSITION; DRUG EXCRETION; DRUG FECES LEVEL; DRUG HYDROLYSIS; DRUG HYDROXYLATION; DRUG METABOLISM; DRUG OXIDATION; DRUG STRUCTURE; DRUG URINE LEVEL; HYDRATION; IN VIVO STUDY; INTESTINE; LIQUID CHROMATOGRAPHY; LIVER; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; TIME OF FLIGHT MASS SPECTROMETRY;

ADMINISTRATION, ORAL; ANIMALS; BILE; BIOTRANSFORMATION; CHROMATOGRAPHY, LIQUID; DRUGS, CHINESE HERBAL; FECES; HYDROLYSIS; INJECTIONS, INTRAVENOUS; INTESTINES; LIVER; MALE; MOLECULAR STRUCTURE; OLEANOLIC ACID; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; SAPONINS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 84874077681     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.048975     Document Type: Article

References (49)

1. Abe H, Odashima S, and Arichi S (1978a) The effects of saikosaponins on biological membranes. 2. Changes in electron spin resonance spectra from spin-labelled erythrocyte and erythrocyte ghost membranes. Planta Med 34:287-290.
2. Abe H, Sakaguchi M, Konishi H, Tani T, and Arichi S (1978b) The effects of saikosaponins on biological membranes. 1. The relationship between the structures of saikosaponins and haemolytic activity. Planta Med 34:160-166.
3. Abe H, Sakaguchi M, Yamada M, Arichi S, and Odashima S (1980) Pharmacological actions of saikosaponins isolated from Bupleurum falcatum. 1. Effects of saikosaponins on liver function. Planta Med 40:366-372.
4. Abrahams HE and Robinson D (1969) b-D-Glucosidases and related enzymic activities in pig kidney. Biochem J 111:749-755.
5. Ahn BZ and Sok DE (2006) Pharmacological activity of saikosaponins, in Bupleurum Species: Scientific Evaluation and Clinical Applications (Pan SL ed) pp 151-157, Taylor and Francis Group, Boca Raton, FL
6. Ahn BZ, Yoon YD, Lee YH, Kim BH, and Sok DE (1998) Inhibitory effect of bupleuri radix saponins on adhesion of some solid tumor cells and relation to hemolytic action: screening of 232 herbal drugs for anti-cell adhesion. Planta Med 64:220-224.
7. Bermejo Benito P, Abad Martínez MJ, Silván Sen AM, Sanz Gómez A, Fernández Matellano L, Sánchez Contreras S, and Díaz Lanza AM (1998) In vivo and in vitro antiinflammatory activity of saikosaponins. Life Sci 63:1147-1156.
8. Brunton L, Parker K, Blumenthal D, and Buxton I (2008) Goodman & Gilman's Manual of Pharmacology and Therapeutics, 11th ed, McGraw-Hill, San Diego, CA. Chen SM, Sato N, Yoshida M, Satoh N, and Ueda S (2008) Effects of Bupleurum scorzoneraefolium, Bupleurum falcatum, and saponins on nephrotoxic serum nephritis in mice. J Ethnopharmacol 116:397-402.
9. Cheng PW, Ng LT, Chiang LC, and Lin CC (2006) Antiviral effects of saikosaponins on human coronavirus 229E in vitro. Clin Exp Pharmacol Physiol 33:612-616.
10. Chiang LC, Ng LT, Liu LT, Shieh DE, and Lin CC (2003) Cytotoxicity and anti-hepatitis B virus activities of saikosaponins from Bupleurum species. Planta Med 69:705-709.
11. Daniels LB, Coyle PJ, Chiao YB, Glew RH, and Labow RS (1981) Purification and characterization of a cytosolic broad specificity beta-glucosidase from human liver. J Biol Chem 256: 13004-13013.
12. Fan J, Li X, Li P, Li N, Wang T, Shen H, Siow Y, Choy P, and Gong Y (2007) Saikosaponind attenuates the development of liver fibrosis by preventing hepatocyte injury. Biochem Cell Biol 85:189-195.
13. Fujiwara K and Ogihara Y (1986) Pharmacological effects of oral saikosaponin a may differ depending on conditions of the gastrointestinal tract. Life Sci 39:297-301.
14. Glew RH, Peters SP, and Christopher AR (1976) Isolation and characterization of betaglucosidase from the cytosol of rat kidney cortex. Biochim Biophys Acta 422:179-199.
15. Hattori T, Nishimura H, Kase Y, and Takeda S (2008) Saireito and saikosaponin D prevent urinary protein excretion via glucocorticoid receptor in adrenalectomized WKY rats with heterologous-phase anti-GBM nephritis. Nephron Physiol 109:19-27.
16. Hsu MJ, Cheng JS, and Huang HC (2000) Effect of saikosaponin, a triterpene saponin, on apoptosis in lymphocytes: association with c-myc, p53, and bcl-2 mRNA. Br J Pharmacol 131: 1285-1293.
17. Hsu YL, Kuo PL, and Lin CC (2004) The proliferative inhibition and apoptotic mechanism of Saikosaponin D in human non-small cell lung cancer A549 cells. Life Sci 75: 1231-1242.
18. Huang HQ, Zhang X, Lin M, Shen YH, Yan SK, and Zhang WD (2008) Characterization and identification of saikosaponins in crude extracts from three Bupleurum species using LC-ESIMS. J Sep Sci 31:3190-3201.
19. Kaminsky LS and Zhang QY (2003) The small intestine as a xenobiotic-metabolizing organ. Drug Metab Dispos 31:1520-1525.
20. Kida H, Akao T, Meselhy MR, and Hattori M (1998) Metabolism and pharmacokinetics of orally administered saikosaponin b1 in conventional, germ-free and Eubacterium sp. A-44-infected gnotobiote rats. Biol Pharm Bull 21:588-593.
21. Kida H, Nakamura N, Meselhy MR, Akao T, and Hattori M (1997) Isolation and identification of human intestinal bacteria capable of hydrolyzing saikosaponins. J Tradit Med 14:34-40.
22. Kim BM and Hong SH (2011) Sequential caspase-2 and caspase-8 activation is essential for saikosaponin a-induced apoptosis of human colon carcinoma cell lines. Apoptosis 16: 184-197.
23. Kubota T and Hinoh H (1968) Triterpenoids from bupleurum falcatum L.-III: Isolation of genuine sapogenins, Saikogenins E, F and G. Tetrahedron 24:675-686.
24. Kubota T, Tonami F, and Hinoh H (1966) The structure of saikogenins A, B, C and D, triterpenoid alcohols of bupleurum falcatum L. Tetrahedron Lett 7:701-710.
25. Kumazawa Y, Kawakita T, Takimoto H, and Nomoto K (1990) Protective effect of saikosaponin A, saikosaponin D and saikogenin D against Pseudomonas aeruginosa infection in mice. Int J Immunopharmacol 12:531-537.
26. Kumazawa Y, Takimoto H, Nishimura C, Kawakita T, and Nomoto K (1989) Activation of murine peritoneal macrophages by saikosaponin a, saikosaponin d and saikogenin d. Int J Immunopharmacol 11:21-28.
27. Leung CY, Liu L, Wong RN, Zeng YY, Li M, and Zhou H (2005) Saikosaponin-d inhibits T cell activation through the modulation of PKCtheta, JNK, and NF-kappaB transcription factor. Biochem Biophys Res Commun 338:1920-1927.
28. Li P, Gong Y, Zu N, Li Y, Wang B, and Shimizu F (2005) Therapeutic mechanism of Saikosaponin-d in anti-Thy1 mAb 1-22-3-induced rat model of glomerulonephritis. Nephron, Exp Nephrol 101:e111-e118.
29. Motoo Y and Sawabu N (1994) Antitumor effects of saikosaponins, baicalin and baicalein on human hepatoma cell lines. Cancer Lett 86:91-95.
30. Nose M, Amagaya S, and Ogihara Y (1989a) Corticosterone secretion-inducing activity of saikosaponin metabolites formed in the alimentary tract. Chem Pharm Bull (Tokyo) 37: 2736-2740.
31. Nose M, Amagaya S, and Ogihara Y (1989b) Effects of saikosaponin metabolites on the hemolysis of red blood cells and their adsorbability on the cell membrane. Chem Pharm Bull (Tokyo) 37:3306-3310.
32. Robinson D (1956) The fluorimetric determination of beta-glucosidase: its occurrence in the tissues of animals, including insects. Biochem J 63:39-44.
33. Segal R, Shud F, and Milo-Goldzweig I (1978) Hemolytic properties of synthetic glycosides. J Pharm Sci 67:1589-1592.
34. Shimizu K, Amagaya S, and Ogihara Y (1984) Quantitative analysis of the metabolites of saikosaponin a using high-performance liquid chromatography. J Chromatogr A 307:488-492.
35. Shimizu K, Amagaya S, and Ogihara Y (1985a) Structural transformation of saikosaponins by gastric juice and intestinal flora. J Pharmacobiodyn 8:718-725.
36. Shimizu K, Amagaya S, and Ogihara Y (1985b) New derivatives of saikosaponins. Chem Pharm Bull (Tokyo) 33:3349-3355.
37. Sun Y, Cai TT, Zhou XB, and Xu Q (2009) Saikosaponin a inhibits the proliferation and activation of T cells through cell cycle arrest and induction of apoptosis. Int Immunopharmacol 9:978-983.
38. Tang YH, Zhang YY, Zhu HY, and Huang CG (2007) A high-performance liquid chromatographic method for saikosaponin a quantification in rat plasma. Biomed Chromatogr 21: 458-462.
39. Tsai YJ, Chen IL, Horng LY, and Wu RT (2002) Induction of differentiation in rat C6 glioma cells with Saikosaponins. Phytother Res 16:117-121.
40. Wang P, Ren J, Tang J, Zhang D, Li B, and Li Y (2010b) Estrogen-like activities of saikosaponind in vitro: a pilot study. Eur J Pharmacol 626:159-165.
41. Wang Q, Zheng XL, Yang L, Shi F, Gao LB, Zhong YJ, Sun H, He F, Lin Y, and Wang X (2010a) Reactive oxygen species-mediated apoptosis contributes to chemosensitization effect of saikosaponins on cisplatin-induced cytotoxicity in cancer cells. J Exp Clin Cancer Res 29: 159-166.
42. Wen-Sheng W (2003) ERK signaling pathway is involved in p15INK4b/p16INK4a expression and HepG2 growth inhibition triggered by TPA and Saikosaponin a. Oncogene 22: 955-963.
43. Wu SJ, Lin YH, Chu CC, Tsai YH, and Chao JC (2008) Curcumin or saikosaponin a improves hepatic antioxidant capacity and protects against CCl4-induced liver injury in rats. J Med Food 11:224-229.
44. Xu L, Song R, Tian JX, Tian Y, Liu GQ, and Zhang ZJ (2012) Analysis of saikosaponins in rat plasma by anionic adducts-based liquid chromatography tandem mass spectrometry method. Biomed Chromatogr 26:808-815.
45. Yokoyama H, Hiai S, and Oura H (1981) Chemical structures and corticosterone secretioninducing activities of saikosaponins. Chem Pharm Bull (Tokyo) 29:500-504.
46. Yu Y, Yang WX, Wang H, Zhang WZ, Liu BH, and Dong ZY (2002) Characteristics and mechanism of enzyme secretion and increase in [Ca2+]i in Saikosaponin(I) stimulated rat pancreatic acinar cells. World J Gastroenterol 8:524-527.
47. Zhang H, Zhang D, Ray K, and ZhuM(2009)Mass defect filter technique and its applications to drug metabolite identification by high-resolution mass spectrometry. J Mass Spectrom 44:999-1016.
48. Zhang QY, Kaminsky LS, Dunbar D, Zhang J, and Ding X (2007) Role of small intestinal cytochromes p450 in the bioavailability of oral nifedipine. Drug Metab Dispos 35:1617-1623.
49. ZhuM, Ma L, ZhangD, Ray K, ZhaoW,HumphreysWG, SkilesG, SandersM, and Zhang H (2006) Detection and characterization of metabolites in biological matrices using mass defect filtering of liquid chromatography/high resolution mass spectrometry data. Drug Metab Dispos 34:1722-1733.