Cytotoxic and apoptosis-inducing effect of ent-15-oxo-kaur-16-en-19-oic acid, a derivative of grandiflorolic acid from Espeletia schultzii

Phytochemistry

Volumn 69, Issue 2, 2008, Pages 432-438

  Ruiz, Yarimar ^a   Rodrígues, Juan ^b   Arvelo, Francisco ^b   Usubillaga, Alfredo ^c   Monsalve, Mariugenia ^c   Diez, Nardy ^a   Galindo Castro, Iván ^a  

^a Fundacion Instituto de Estudios Avanzados IDEA   (Venezuela)

^b UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

^c UNIVERSIDAD DE LOS ANDES   (Venezuela)

Author keywords

Apoptosis; ent 5 Oxo kaur 16 en 19 oic acid; ent Kaurenoids; Espeletia schultzii; Espeletiinae; Frailej n; PC 3 cell line

Indexed keywords

CASPASE 3; DITERPENE; ENT 15 OXO KAUR 16 EN 19 OIC ACID; ENT-15-OXO-KAUR-16-EN-19-OIC ACID; GRANDIFLOROLIC ACID; PROTEIN BCL 2; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; ASTERACEAE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENZYME ACTIVATION; GENETICS; HUMAN; METABOLISM; TUMOR CELL LINE;

APOPTOSIS; ASTERACEAE; CASPASE 3; CELL LINE, TUMOR; CELL SURVIVAL; DITERPENES; ENZYME ACTIVATION; HUMANS; MOLECULAR STRUCTURE; PROTO-ONCOGENE PROTEINS C-BCL-2;

ESPELETIA; ESPELETIA SCHULTZII;

EID: 37549007617     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.07.025     Document Type: Article

References (27)

1. Alonso R. Synthetic diterpene derivatives from kaura-9(11),16-dien-19-oic acid: cytostatic and cytotoxic activity against human cancer cell lines. Khim.-Farm. Zh. 40 (2006) 14-17
2. Aristeguieta L. Flora de venezuela, edicion especial del instituto botánico de venezuela. Compositae X (1964) 447-448
3. Brieskorn C., and Pöhlmann E. Diterpene vom kaurantyp aus der composite Espeletia schultzii (wedd). Tetrahedron Lett. 54 (1968) 5661-5664
4. Castrillo A., De las Heras B., Hortelano S., Rodríguez B., Villars A., and Boscá L. Inhibition of the nuclear factor κB (NFκB) pathway by tetracyclic kaurene diterpene in macrophages. J. Biol. Chem. 276 (2001) 15854-15860
5. Cory S., and Adams J. The Bcl2 family: regulators of the cellular life-or-death switch. Nature Rev. Cancer 2 (2002) 647-656
6. Cuatrecasas J. A new subtribe in the Heliantheae (Compositae) Espeletiinae. Phytologia 35 (1976) 43-61
7. Denizot F., and Lang R. Rapid colorimetric assay for cell grow and survival modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Meth. 89 (1986) 271-277
8. Ghisalberti E.L. The biological activity of naturally occurring kaurene diterpenes. Fitoterapia LXVIII (1997) 303-325
9. Honda T., Shunsuke K., Spurgers K., Gjertsen B., Roth J., Fang B., Lowe S., Norris J., Meyn R., and McDonnell T. A recombinant adenovirus expressing wild-type Bax induces apoptosis in prostate cancer cells independently of their Bcl-2 status and androgen sensitivity. Cancer Biol. Ther. 1 (2002) 163-167
10. Jemal A., Murray T., Ward E., Samuels A., Tiwari R., Ghafoor A., Feuer E., and Thun M. Cancer statistics, 2005. Cancer J. Clin. 55 (2005) 10-30
11. Johnstone R., Ruefli A., and Lowe S. Apoptosis: a link between cancer genetics and chemotherapy. Cell 108 (2002) 153-164
12. Kaur S., Hushem M., Arora S., Härkönen P., and Kumar S. The in vitro cytotoxic and apoptotic activity of Triphala, an Indian herbal drug. J. Ethnopharmacol. 97 (2005) 15-20
13. Lee J., Koo T., Hwang B., and Lee L. Kaurene diterpene, Kamebakaurin, inhibits NF-(B by directly targeting the DNA-binding activity of p50 and blocks the expression of antiapoptotic NF-κB target genes. J. Biol. Chem. 277 (2002) 18411-18420
14. Li X., Xiao W., Pu J., Ban L., Shen Y., Weng Z., Li S., and Sun H. Cytotoxic ent-kaurene diterpenoids from Isodon phyllostachys. Phytochemistry 67 (2006) 1336-1340
15. Ling Y.-H., Jiang J.-D., Holland J., and Perez-Soler R. Arsenic trioxide produces polymerization of microtubules and mitotic arrest before apoptosis in human tumor cell lines. Mol. Pharmacol. 62 (2002) 529-538
16. Morales A., Pérez P., Mendoza R., Compagnone R., Suárez A., Arvelo F., Ramirez J., and Galindo-Castro I. Cytotoxic and propapoptotic activity of ent-16β-17α-dihydroxykaurane on human mammary carcinoma cell line MCF-7. Cancer Lett. 218 (2005) 109-116
17. Nagashima F., Kondoh M., Kawase M., Simizu S., Osada H., Watanabe M., Sato M., and Asakawa Y. Apoptosis-inducing properties of ent -kaurene-type diterpenoids from the liverwort Jungermannia truncate. Planta Med. 69 (2003) 377-379
18. Nguyen J., and Wells A. Direct activation of the apoptotic machinery as a mechanism to target cancer cells. Proc. Natl. Acad. Sci. USA 100 (2003) 7533-7538
19. Piozzi F., Sprio V., Passannanti S., and Mondelli R. Structura dell'acido gradiflorolico. Gazz. Chim. Ital. 98 (1968) 907-910
20. Rundle N., Nelson J., Flory M., Joseph J., Th́ng J., Aebersold R., Dasso M., Andersen R., and Roberge M. An ent-kaurene that inhibits mitotic chromososme movement and binds the kinetochore protein Ran-binding protein 2. ASC Chem. Biol. 7 (2006) 443-450
21. Sasaki J., Ramesh R., Chada S., Gomyo Y., Roth J., and Mukhopadhyay T. The anthelmintic drug mebendazole induces mitotic arrest and apoptosis by depolymerizing tubulin in non-small cell lung cancer cells. Mol. Cancer Ther. 1 (2002) 1201-1209
22. Taylor P., Cesari I., Arsenak M., Ballen D., Abad M., Fernández A., Milano B., Ruiz M., Williams B., and Michelangeli F. Evaluation of Venezuelan medicinal plant extracts for antitumor and antiprotease activities. Pharm. Biol. 44 (2006) 1-14
23. Tilley W., Wilson M., Marcelli M., and McPhaul M. Androgen receptor gene expression in human prostate carcinoma cell lines. Cancer Res. 50 (1990) 5382-5386
24. Usubillaga A., Romero M., and Aparicio R. Kaurenic acid in Espeletiinae. Acta Hort. 597 (2003) 129-130
25. Vieira H., Takahashi J., Pimenta L., and Boaventura M. Effects of kaurane diterpene derivatives on germination and growth of Lactuca sativa seedlings. Z. Naturforsch. C 60 (2005) 72-78
26. Winter R., Kramer A., Borkowski A., and Kyprianou N. Loss of caspase-1 and caspase-3 protein expression in human prostate cancer. Cancer Res. 61 (2001) 1227-1232
27. Xiang W., Li R.-T., Wang Z.-Y., Li S.-H., Zhao Q.-S., Zhang H.-J., and Sun H.-D. ent-kaurene diterpenoids from Isodon aresbius. Phytochemistry 65 (2004) 1173-1177