Gomisin N isolated from Schisandra chinensis significantly induces anti-proliferative and pro-apoptotic effects in hepatic carcinoma

Molecular Medicine Reports

Volumn 2, Issue 5, 2009, Pages 725-732

  Su, Youn Yim ^a   You, Jin Lee ^b   Yoen, Kyung Lee ^b   Seung, Eun Jung ^b   Ji, Ha Kim ^b   Ji, Eun Kim ^b   Hak, Jin Kim ^b   Beung, Gu Son ^b   Young, Hoon Park ^b   Young, Guen Lee ^b   Young, Whan Choi ^b   Dae, Youn Hwang ^b  

^a CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^b Pusan National University   (South Korea)

Author keywords

Anti proliferation; Apoptosis; Bax; Bcl 2; Gomisin N

Indexed keywords

GOMISIN; LIGNAN; PROTEIN BAX; PROTEIN BCL 2; PROTEIN P53; SCHISANDRA CHINENSIS EXTRACT; SCHISANDRIN; SCHISANDRIN C; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL ASSAY; CELL DEATH; CELL PROLIFERATION; CELL STRUCTURE; CHINESE MEDICINE; CONTROLLED STUDY; FLOW CYTOMETRY; HUMAN; HUMAN CELL; LIVER CARCINOMA; PROTEIN EXPRESSION; SCHISANDRA CHINENSIS; SCHISANDRACEAE; SIGNAL TRANSDUCTION;

SCHISANDRA CHINENSIS;

EID: 69249203689     PISSN: 17912997     EISSN: 17913004     Source Type: Journal    
DOI: 10.3892/mmr-00000163     Document Type: Article

References (51)

1. Panossian A and Wikman G: Pharmacology of Schisandra chinensis Bail.: an overview of Russian research and uses in medicine. J Ethnopharmacol 118: 183-212, 2008.
2. Azzam HS, Goertz C, Fritts M and Jonas WB: Natural products and chronic hepatitis C virus. Liver Int 27: 17-25, 2007. (Pubitemid 46139424)
3. Panossian AG: Effects of heavy physical exercise and adaptogens on nitric oxide content in human saliva. Phytomedicine 6: 17-26, 1999.
4. Chiu PY, Mak DH and Poon MK: In vivo antioxidant action of a lignan-enriched extract of Schisandra fruit and an anthraquinone-containing extract of Polygonum root in comparison with schisandrin B and emodin. Planta Med 68: 951-956, 2002.
5. Ko KM: schisandrin B protects against tert-butylhydroperoxide-induced cerebral toxicity by enhancing glutathione antioxidant status in mouse brain. Mol Cell Biochem 238: 181-186, 2002.
6. Nakamura K, Yoshida M and Uchiwa H: Down-regulation of melanin synthesis by a biphenyl derivative and its mechanism. Pigment Cell Res 16: 494-500, 2003. (Pubitemid 37093026)
7. Yim TK and Ko KM: schisandrin B protects against myocardial ischemia-reperfusion injury by enhancing myocardial glutathione antioxidant status. Mol Cell Biochem 196: 151-156, 1999.
8. Baek MS, Kim JY and Myung SW: Metabolism of dimethyl-4,4′- dimethoxy-5,6,5′,6′-dimethylene dioxybiphenyl-2,2′- dicarboxylate (DDB) by human liver microsomes: characterization of metabolic pathways and of cytochrome P450 isoforms involved. Drug Metab Dispos 29: 381-388, 2001.
9. Iwata H, Tezuka Y and Kadota S: Identification and characterization of potent CYP3A4 inhibitors in Schisandra fruit extract. Drug Metab Dispos 32: 1351-1358, 2004. (Pubitemid 39564554)
10. Chang HF, Lin YH, Chu CC, Wu SJ, Tsai YH and Chao JC: Protective effects of Ginkgo biloba, Panax ginseng, and Schisandra chinensis extract on liver injury in rats. Am J Chin Med 35: 995-1009, 2007.
11. Ko KM, Ip SP, Poon MK, Wu SS, Che CT, Ng KH and Kong YC: Effect of a lignan-enriched fructus schisandrae extract on hepatic glutathione status in rats: protection against carbon tetrachloride toxicity. Planta Med 61: 134-137, 1995.
12. Chen N, Chiu PY and Ko KM: schisandrin B enhances cerebral mitochondrial antioxidant status and structural integrity, and protects against cerebral ischemia/reperfusion injury in rats. Biol Pharm Bull 31: 1387-1391, 2008. (Pubitemid 351930652)
13. Kubo S, Ohkura Y, Mizoguchi Y, Matsui-Yuasa I, Otani S, Morisawa S, Kinoshita H, Takeda S, Aburada M and Hosoya E: Effect of gomisin A (TJN-101) on liver regeneration. Planta Med 58: 489-492, 1992. (Pubitemid 23074532)
14. Choi YW, Takamatsu S, Khan SI, Srinivas PV, Ferreira D, Zhao J and Khan IA: Schisandrene, a dibenzocyclooctadiene lignan from Schisandra chinensis: structure-antioxidant activity relationships of dibenzocyclooctadiene lignans. J Nat Prod 69: 356-359, 2006.
15. Avula B, Dentali S and Khan IA: Simultaneous identification and quantification by liquid chromatography of benzethonium chloride, methyl paraben and triclosan in commercial products labeled as grapefruit seed extract. Pharmazie 62: 593-596, 2007. (Pubitemid 47326164)
16. Seo SM, Lee HJ, Park YK, Lee MK, Park JI and Paik KH: Lignans from the fruits of Schizandra chinensis and their inhibitory effects on dopamine content in PC12 cells. Nat Prod Sci 10: 104-108, 2004.
17. Ikeya Y, Taguchi H, Yosioka I and Kobayashi H: The constituents of Schizandra chinensis Baill. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin. Chem Pharm Bull 27: 1383-1394, 1979.
18. Ikeya Y, Taguchi H, Yosioka I and Kobayashi H: The constituents of Schizandra chinensis Baill. III. The structures of four new lignans, gomisin H and its derivatives, angeloyl-, tigloyl- and benzoyl-gomisin H. Chem Pharm Bull 27: 1576-1582, 1979.
19. Park JY, Lee SJ, Yun MR, Seo KW, Bae SS, Park JW, Lee YJ, Shin WJ, Choi YW and Kim CD: gomisin A from Schisandra chinensis induces endothelium-dependent and direct relaxation in rat thoracic aorta. Planta Med 73: 1537-1542, 2007.
20. Andree HA, Reutelingsperger CP, Hauptmann R, Hemker HC, Hermens WT and Willems GM: Binding of vascular anticoagulant alpha (VAC alpha) to planar phospholipid bilayers. J Biol Chem 265: 4923-4928, 1990. (Pubitemid 20117129)
21. Casciola-Rosen L, Rosen A, Petri M and Schlissel M: Surface blebs on apoptotic cells are sites of enhanced procoagulant activity: implications for coagulation events and antigenic spread in systemic lupus erythematosus. Proc Natl Acad Sci USA 93: 1624-1629, 1996. (Pubitemid 26075176)
22. Tsujimoto Y: Role of Bcl-2 family proteins in apoptosis: apoptosomes or mitochondria? Genes Cells 3: 697-707, 1998.
23. Tsujimoto Y and Shimizu S: Bcl-2 family: life-or-death switch. FEBS Lett 466: 6-10, 2000.
24. Bosch FX, Ribes J, Díaz M and Cléries R: Primary liver cancer: worldwide incidence and trends. Gastroenterology 127: S5-S16, 2004. (Pubitemid 39423365)
25. Adami A, Hunter D and Trichopoulos D: Cancer of the liver and biliary tract. In: Textbook of Cancer Epidemiology. 2nd edition. Oxford University Press, Oxford, pp308-332, 2008.
26. El-Serag HB and Mason AC: Risk factors for the rising rates of primary liver cancer in the United States. Arch Intern Med 60: 3227-3230, 2000.
27. Thomas MB and Zhu AX: Hepatocellular carcinoma: the need for progress. J Clin Oncol 23: 2892-2899, 2005.
28. Bruix J and Sherman M: Management of hepatocellular carcinoma. Hepatology 42: 1208-1236, 2005.
29. He XG, Lian L-Z and Lin L-Z: Electrospray high performance liquid chromatography-mass spectrometry in phytochemical analysis of kava (Piper methysticum) extract. Plant Med 63: 70-74, 1997.
30. Chen DF, Zhang SX, Kozuka M, Sun QZ, Feng J, Wang Q, Mukainaka T, Nobukuni Y, Tokuda H, Nishino H, Wang HK, Morris-Natschke SL and Lee KH: Interiotherins C and D, two new lignans from Kadsura interior and antitumor-promoting effects of related neolignans on Epstein-Barr virus activation. J Nat Prod 65: 1242-1245, 2002.
31. Yasukawa K, Ikeya Y, Mitsuhashi H, Iwasaki M, Aburada M, Nakagawa S, Takeuchi M and Takido M: gomisin A inhibits tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin. Oncology 49: 68-71, 1992.
32. Ohtaki Y, Hida T, Hiramatsu K, Kanitani M, Ohshima T, Nomura M, Wakita H, Aburada M and Miyamoto KI: Deoxycholic acid as an endogenous risk factor for hepatocarcinogenesis and effects of gomisin A, a lignan component of Schizandra fruits. Anticancer Res 16: 751-755, 1996. (Pubitemid 26182005)
33. Nomura M, Nakachiyama M, Hida T, Ohtaki Y, Sudo K, Aizawa T, Aburada M and Miyamoto KI: gomisin A, a lignan component of Schizandora fruits, inhibits development of preneoplastic lesions in rat liver by 3′-methyl-4- dimethylamino-azobenzene. Cancer Lett 76: 11-18, 1994. (Pubitemid 124010716)
34. Wu MD, Huang RL, Kuo LM, Hung CC, Ong CW and Kuo YH: The anti-HBsAg (human type B hepatitis, surface antigen) and anti-HBeAg (human type B hepatitis, e antigen) C18 dibenzocyclooctadiene lignans from Kadsura matsudai and Schizandra arisanensis. Chem Pharm Bull 51: 1233-1236, 2003.
35. Chen DF, Zhang SX, Xie L, Xie JX, Chen K, Kashiwada Y, Zhou BN, Wang P Cosentino LM and Lee KH: Anti-AIDS agents. XXVI. Structure-activity correlations of gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues. Bioorg Med Chem 5: 1715-1723, 1997.
36. Lu H and Liu GT: Anti-oxidant activity of dibenzocyclooctene lignans isolated from Schisandraceae. Planta Med 58: 311-313, 1992.
37. Li XY: Bioactivity of neolignans from fructus Schizandrae. Mem Inst Oswaldo Cruz 86: 31-37, 1991.
38. Ip SP, Poon MK, Wu SS, Che CT, Ng KH, Kong YC and Ko KM: Effect of schisandrin B on hepatic glutathione antioxidant system in mice: protection against carbon tetrachloride toxicity. Planta Med 61: 398-401, 1995.
39. Ip SP and Ko KM: The crucial antioxidant action of schisandrin B in protecting against carbon tetrachloride hepatotoxicity in mice: a comparative study with butylated hydroxytoluene. Biochem Pharmacol 52: 1687-1693, 1996.
40. Chiu PY, Leung HY, Poon MK, Mak DH and Ko KM: (-) schisandrin B is more potent than its enantiomer in enhancing cellular glutathione and heat shock protein production as well as protecting against oxidant injury in H9c2 cardiomyocytes. Mol Cell Biochem 289: 185-191, 2006.
41. Li L, Lu Q, Shen Y and Hu X: schisandrin B enhances doxorubicin-induced apoptosis of cancer cells but not normal cells. Biochem Pharmacol 71: 584-595, 2006. (Pubitemid 43121992)
42. 2+-induced mitochondrial permeability transition and mitochondrial membrane potential in H9c2 cardiomyocytes. Life Sci 82: 1092-1101, 2008.
43. Schwartz LM, Smitho SW, Jones MEE and Osborne BA: Do all programmed cell deaths occur via apoptosis? Proc Nati Acad Sci USA 90: 980-984, 1993.
44. Bursch W, Ellinger A, Gerner C, Fröhwein U and Schulte-Hermann R: Programmed cell death (PCD). Apoptosis, autophagic PCD, or others? Ann NY Acad Sci 926: 1-12, 2000.
45. Homburg CH, De Haas M, von dem Borne AE, Verhoeven AJ, Reutelingsperger CP and Roos D: Human neutrophils lose their surface Fc gamma RIII and acquire Annexin V binding sites during apoptosis in vitro. Blood 85: 532-540, 1995.
46. Koopman G, Reutelingsperger CP, Kuijten GA, Keehnen RM, Pals ST and van Oers MH: Annexin V for flow cytometric detection of phosphatidylserine expression on B cells undergoing apoptosis. Blood 84: 1415-1420, 1994. (Pubitemid 24273007)
47. Apakama I, Robinson MC, Walter NM, Charlton RG, Royds JA, Fuller CE, Neal DE and Hamdy FC: Bcl-2 overexpression combined with p53 accumulation correlates with hormone refractory prostate cancer. Br J Urol 74: 1258-1262, 1996.
48. Joensuu H, Pylkkänen L and Toikkanen S: Bcl-2 protein expression and long-term survival in breast cancer. Am J Pathol 145: 1191-1198, 1994. (Pubitemid 24345666)
49. Baekelandt M, Holm R, Nesland JM, Tropé CG and Kristensen GB: Expression of apoptosis-related proteins is an independent determinant of patient prognosis in advanced ovarian cancer. J Clin Oncol 18: 3745-3747, 2000. (Pubitemid 30846223)
50. Harima Y, Nagata K, Harima K, Oka A, Ostapenko VV, Shikata N, Ohnishi T and Tanaka Y: Bax and bcl-2 protein expression following radiation therapy versus radiation plus thermoradiotherapy in stage IIIB cervical carcinoma. Cancer 88: 132-138, 2000. (Pubitemid 30027688)
51. Ito T, Fujieda S, Tsuzuki H, Sunaga H, Fan G, Sugimoto C, Fukuda M and Saito H: Decreased expression of bax is correlated with poor prognosis in oral and oropharyngeal carcinoma. Cancer Lett 140: 81-91, 1999. (Pubitemid 29251317)