Bullatacin, a potent antitumor Annonaceous acetogenin, induces apoptosis through a reduction of intracellular cAMP and cGMP levels in human hepatoma 2.2.15 cells

Biochemical Pharmacology

Volumn 65, Issue 3, 2003, Pages 319-327

  Chiu, Hui Fen ^a,b   Chih, Tsai Tung ^c   Hsian, Yun Mei ^a   Tseng, Chih Hua ^a   Wu, Ming Jung ^b   Wu, Yang Chang ^b  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^c FOOYIN UNIVERSITY   (Taiwan)

Author keywords

Annonaceous acetogenin; Apoptosis; Bullatacin; cAMP; cGMP; Hepatoma 2.2.15 cells

Indexed keywords

ACETOGENIN; ANTINEOPLASTIC AGENT; APOPTOSIS INHIBITOR; BULLATACIN; CYCLIC AMP; CYCLIC GMP; FLUORESCEIN ISOTHIOCYANATE; FORSKOLIN; LIPOCORTIN 5; PROPIDIUM IODIDE; S NITROSOGLUTATHIONE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL DESTRUCTION; CELL LEVEL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENCY; HEPATOMA CELL; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STAINING;

ANNEXIN A5; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARCINOMA, HEPATOCELLULAR; CYCLIC AMP; CYCLIC GMP; DRUG INTERACTIONS; FLUORESCEIN-5-ISOTHIOCYANATE; FORSKOLIN; FURANS; HUMANS; S-NITROSOGLUTATHIONE; TUMOR CELLS, CULTURED;

EID: 0037299758     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(02)01554-X     Document Type: Article

References (47)

1. Landolt J.L., Ahammadsahib K.I., Hollingworth R.M., Barr R., Crane F.L., Buerck N.L., McCabe G.P., McLaughlin J.L. Determination of structure-activity relationships of Annonaceous acetogenins by inhibition of oxygen uptake in rat liver mitochondria. Chem. Biol. Interact. 98:1995;1-13.
2. Alali F.Q., Liu X.X., McLaughlin J.L. Annonaceous acetogenins: recent progress. J. Nat. Prod. 62:1999;504-540.
3. Jolad S.D., Hoffmann J.J., Schram K.H., Cole J.R. Uvaricin, a new antitumor agent from Uvaria accuminata (Annonaceae). J. Org. Chem. 47:1982;3151-3153.
4. Zafra-Polo M.C., Figadere B., Gallardo T., Tormo J.R., Cortes D. Natural acetogenins from Annonaceae, synthesis and mechanisms of action. Phytochemistry. 48:1998;1087-1117.
5. Wu Y.C., Chang F.R., Duh C.Y., Wang S.K. Annoreticuin and isoannoreticuin - 2 new cytotoxic acetogenins from Annona reticulata. Heterocycles. 34:1992;667-674.
6. Wu Y.C., Chang F.R., Chen K.S., Liang S.C., Lee M.R. Diepoxymontin, a novel acetogenin from Annona montana. Heterocycles. 38:1994;1475-1478.
7. Chang F.R., Chen J.L., Chiu H.F., Wu M.J., Wu Y.C. Acetogenins from seeds of Annona reticulata. Phytochemistry. 47:1998;1057-1061.
8. Tsai S.H., Hsieh P.C., Wei L.L., Chiu H.F., Wu Y.C. Synthesis of a hydroxylated muricatacin analog related to squamocin. Tetrahedron Lett. 40:1999;1975-1976.
9. Chen C.Y., Chang F.R., Chiu H.F., Wu M.J., Wu Y.C. Aromin-A, an Annonaceous acetogenin from Annona cherimola. Phytochemistry. 51:1999;429-433.
10. Liaw C.C., Chang F.R., Chen Y.Y., Chiu H.F., Wu M.J., Wu Y.C. New Annonaceous acetogenins from Rollinia mucosa. J. Nat. Prod. 62:1999;1613-1617.
11. Chang F.R., Chen J.L., Lin C.Y., Chiu H.F., Wu M.J., Wu Y.C. Bioactive acetogenins from the seeds of Annona atemoya. Phytochemistry. 51:1999;883-889.
12. Chih H.W., Chiu H.F., Tang K.S., Chang F.R., Wu Y.C. Bullatacin, a potent antitumor Annonaceous acetogennin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction. Life Sci. 69:2001;1321-1331.
13. Chang F.R., Wu Y.C. Novel cytotoxic Annonaceous acetogenins from Annona muricata. J. Nat. Prod. 64:2001;925-931.
14. Liaw C.C., Chang F.R., Lin C.Y., Chou C.J., Chiu H.F., Wu M.J., Wu Y.C. New cytotoxic monotetrahydrofuran Annonaceous acetogenins from Annona muricata. J. Nat. Prod. 65:2002;470-475.
15. Oberlies N.H., Chang C.J., McLaughlin J.L. Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells. J. Med. Chem. 40:1997;2102-2106.
16. Rupprecht J.K., Hui Y.H., McLaughlin J.L. Annonaceous acetogenins: a review. J. Nat. Prod. 53:1990;237-278.
17. Fang X.P., Rieser M.J., Gu Z.M., Zhao G.X., McLaughlin J.L. Annonaceous acetogenins: an update review. Phytochem. Anal. 4:1993;27-48.
18. Ahammadsahib K.I., Hollingworth R.M., McGovren J.P., Hui Y.H., McLaughlin J.L. Mode of action of bullatacin: a potent antitumor and pesticidal Annonaceous acetogenin. Life Sci. 53:1993;1113-1120.
19. Morre D.J., de Cabo R., Farley C., Oberlies N.H., McLaughlin J.L. Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes. Life Sci. 56:1995;343-348.
20. Ayoola E.A., Balayan M.S., Deinhardt F., Gust I., Kureshi A.W., Maynard J.E., Nayak N.C., Schatzmayr H.G., Zhuang H., Bradley D.W., Ferguson M., Melnick J., Purcell R.H., Zuckerman A.J. Progress in the control of viral hepatitis: memorandum from a WHO Meeting. Bull. World Health Organ. 66:1988;443-455.
21. Beasley R.P., Hwang L.Y., Lin C.C., Chien C.S. Hepatocellular carcinoma and hepatitis B virus, a prospective study of 22,707 men in Taiwan. Lancet. 2:1981;1129-1133.
22. Sells M.A., Chen M.L., Acs G. Production of hepatitis B virus particles in Hep G2 cells transfected with cloned hepatitis B virus DNA. Proc. Natl. Acad. Sci. U.S.A. 84:1987;1005-1009.
23. Sells M.A., Zelent A.Z., Shvartsman M., Acs G. Replicative intermediates of hepatitis B virus in HepG2 cells that produce infectious virions. J. Virol. 62:1988;2836-2844.
24. Muhl H., Nitsch D., Sandau K., Brune B., Varga Z., Pfeilschifter J. Apoptosis is triggered by cyclic AMP signalling pathway in renal mesangial cells. FEBS Lett. 382:1996;271-275.
25. Lomo J., Blomhoff H.K., Beiske K., Stokke T., Smeland E.B. TGF-β1 and cyclic AMP promote apoptosis in resting human B lymphocytes. J. Immunol. 154:1995;1634-1643.
26. Aharoni D., Dantes A., Oren M., Amsterdam A. cAMP-mediated signals as determinants for apoptosis in primary granulosa cells. Exp. Cell Res. 218:1995;271-282.
27. Loweth A.C., Williams G.T., Scarpello J.H.B., Morgan N.G. Evidence for the involvement of cGMP and protein kinase G in nitric oxide-induced apoptosis in the pancreatic B-cell line, HIT-T15. FEBS Lett. 400:1997;285-288.
28. Wu C.F., Bisphopric N.H., Pratt R.E. Atrial natriuretic peptide induces apoptosis in neonatal rat cardiac myocytes. J. Biol. Chem. 272:1997;14860-14866.
29. Genaro A.M., Hortelano S., Alvarez A., Martínez A.C., Boscá L. Splenic B lymphocyte programmed cell death is prevented by nitric oxide release through mechanisms involving sustained Bcl-2 levels. J. Clin. Invest. 95:1995;1884-1890.
30. Martin S.J., Reutelingsperger C.P.M., McGahon A.J., Rader J.A., Schie R.C.A.A., LaFace D.M., Green D.R. Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl. J. Exp. Med. 182:1995;1545-1556.
31. Vermes I., Haanen C., Steffens-Nakken H., Reutelingsperger C. A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled Annexin V. J. Immunol. Methods. 184:1995;39-51.
32. Fadok V.A., Voelker D.R., Campbell P.A., Cohen J.J., Bratton D.L., Henson M.P. Exposure of phosphatidylserine on the surface of apoptotic lymphocytes triggers specific recognition and removal by macrophages. J. Immunol. 148:1992;2207-2216.
33. Verhoven B., Schlegel R.A., Williamson P. Mechanisms of phosphatidylserine exposure, a phagocyte recognition signal, on apoptotic T lymphocytes. J. Exp. Med. 182:1995;1597-1601.
34. Parvathenani L.K., Buescher E.S., Chacon-Cruz E., Beebe S.J. Type I cAMP-dependent protein kinase delays apoptosis in human neutrophils at a site upstream of caspase-3. J. Biol. Chem. 273:1998;6736-6743.
35. Williams G.T. Programmed cell death: apoptosis and oncogenesis. Cell. 65:1991;1097-1098.
36. Martin S.J., Green D.R. Apoptosis as a goal of cancer therapy. Curr. Opin. Oncol. 6:1994;616-621.
37. Wolvetang E.J., Johnson K.L., Krauer K., Ralph S.J., Linnane A.W. Mitochondrial respiratory chain inhibitors induce apoptosis. FEBS Lett. 339:1994;40-44.
38. Tormo J.R., González M.C., Cortes D., Estornell E. Kinetic characterization of mitochondrial complex I inhibitors using Annonaceous acetogenins. Arch. Biochem. Biophys. 369:1999;119-126.
39. Shimada H., Grutzner J.B., Kozlowski J.F., McLaughlin J.L. Membrane conformation and their relation to cytotoxicity of asimicin and its analogues. Biochemistry. 37:1998;854-866.
40. Rossi A.G., Cousin J.M., Dransfield I., Lawson M.F., Chilvers E.R., Haslett C. Agents that elevate cAMP inhibit human neutrophil apoptosis. Biochem. Biophys. Res. Commun. 217:1995;892-899.
41. Garcia-Bermejo L., Perez C., Vilaboa N.E., Blas E.D., Aller P. cAMP increasing agents attenuate the generation of apoptosis by etoposide in promonocytic leukemia cells. J. Cell Sci. 111:1998;637-644.
42. Beauvais F., Michel L., Dubertret L. The nitric oxide donors, azide and hydroxylamine, inhibit the programmed cell death of cytokine-deprived human eosinophils. FEBS Lett. 361:1995;229-232.
43. Kim Y.M., Talanian R.V., Billiar T.R. Nitric oxide inhibits apoptosis by preventing increases in caspase-3-like activity via two distinct mechanisms. J. Biol. Chem. 272:1997;31138-31148.
44. Garbers D.L. Guanylyl cyclase receptors and their endocrine, paracrine, and autocrine ligands. Cell. 71:1992;1-4.
45. Schmidt H.H., Walter U. NO at work. Cell. 78:1994;919-925.
46. Lincoln T.M., Cornwell T.L. Intracellular cyclic GMP receptor proteins. FASEB J. 7:1993;328-338.
47. Martín-Sanz P., Díaz-Guerra M.J.M., Casado M., Boscá L. Bacterial lipopolysaccharide antagonizes transforming growth factor β1-induced apoptosis in primary cultures of hepatocytes. Hepatology. 23:1996;1200-1207.