Artículo

Cano, L.P.P.; Bartolotta, S.A.; Casanova, N.A.; Siless, G.E.; Portmann, E.; Schejter, L.; Palermo, J.A.; Carballo, M.A. "Isolation of acetylated bile acids from the sponge Siphonochalina fortis and DNA damage evaluation by the comet assay" (2013) Steroids. 78(10):982-986
El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

From the organic extracts of the sponge Siphonochalina fortis, collected at Bahia Bustamante, Chubut, Argentina, three major compounds were isolated and identified as deoxycholic acid 3, 12-diacetate (1), cholic acid 3, 7, 12-triacetate (2) and cholic acid, 3, 7, 12-triacetate. (3). This is the first report of acetylated bile acids in sponges and the first isolation of compound 3 as a natural product. The potential induction of DNA lesions by the isolated compounds was investigated using the comet assay in lymphocytes of human peripheral blood as in vitro model. The results showed that the administration of the bile acid derivatives would not induce DNA damages, indicating that acetylated bile acids are nontoxic metabolites at the tested concentrations. Since the free bile acids were not detected, it is unlikely that the acetylated compounds may be part of the sponge cells detoxification mechanisms. These results may suggest a possible role of acetylated bile acids as a chemical defense mechanism, product of a symbiotic relationship with microorganisms, which would explain their seasonal and geographical variation, and their influence on the previously observed genotoxicity of the organic extract of S. fortis. © 2013 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:Isolation of acetylated bile acids from the sponge Siphonochalina fortis and DNA damage evaluation by the comet assay
Autor:Cano, L.P.P.; Bartolotta, S.A.; Casanova, N.A.; Siless, G.E.; Portmann, E.; Schejter, L.; Palermo, J.A.; Carballo, M.A.
Filiación:UMYMFOR, Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad, Universitaria Pab. 2, 1428 Buenos Aires, Argentina
CIGETOX (Citogenética Humana y Genética Toxicológica), INFIBIOC (Instituto de Fisiopatología y Bioquímica Clínica), Universidad de Buenos Aires (UBA), Junín 956, 1113 CABA Buenos Aires, Argentina
Laboratorio de Bentos, Instituto Nacional de Investigación y Desarrollo Pesquero, Paseo Victoria Ocampo 1, B7602HSA Mar del Plata, Argentina
Palabras clave:Acetylated bile acids; Bacteria; Chemical defense; Comet assay; DNA damage; Marine sponges; bile acid; cholic acid 3,7 diacetate; cholic acid 3,7,12 triacetate; deoxycholic acid 3,12 diacetate; unclassified drug; acetylation; article; cell viability; comet assay; controlled study; detoxification; DNA damage; in vitro study; metabolite; nonhuman; peripheral lymphocyte; Siphonochalina fortis; sponge (Porifera); Bacteria (microorganisms); Siphonochalina; Acetylated bile acids; Bacteria; Chemical defense; Comet assay; DNA damage; Marine sponges; Animals; Cell Survival; Cells, Cultured; Cholic Acids; Comet Assay; DNA Damage; Drug Evaluation, Preclinical; Humans; Lymphocytes; Mutagens; Porifera
Año:2013
Volumen:78
Número:10
Página de inicio:982
Página de fin:986
DOI: http://dx.doi.org/10.1016/j.steroids.2013.05.020
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n10_p982_Cano

Referencias:

  • Thomas, T.R., Kavlekar, D.P., Loka Bharathi, P.A., Marine drugs from sponge-microbe association - A review (2010) Mar Drugs, 8 (4), pp. 1417-1468
  • Thakur, N.L., Muller, W.E.G., Biotechnological potential of marine sponges (2004) Curr Sci, 86, pp. 1506-1512
  • Wang, G., Diversity and biotechnological potential of the sponge-associated microbial consortia (2006) J Ind Microbiol Biotechnol, 33, pp. 545-551
  • Faimali, M., Sepcić, K., Turk, T., Geraci, S., Non-toxic antifouling activity of polymeric 3-alkylpyridinium salts from the Mediterranean sponge Reniera sarai (Pulitzer-Finali) (2003) Biofouling, 19 (1), pp. 47-56
  • Qian, P.Y., Xu, Y., Fusetani, N., Natural products as antifouling compounds: Recent progress and future perspectives (2010) Biofouling, 26, pp. 223-234
  • Bartolotta, S.A., Scuteri, M.A., Hick, A.S., Palermo, J., Rodriguez Brasco, M.F., Hajdu, E., Et Alcarballo, M.A., Evaluation of genotoxic biomarkers in extracts of marine sponges from Argentinean South Sea (2009) JEMBE, 369, pp. 144-147
  • Lievens, S.C., Hope, H., Molinski, T.F., New 3-oxo-chol-4-en-24-oic acids from the marine soft coral Eleutherobia sp (2004) J Nat Prod, 67, pp. 2130-2132
  • Sung, P.J., Fang, L.S., Chen, Y.P., Chen, W.C., Hu, W.P., Ho, C.L., 5b-Steroids from the gorgonian coral Junceella fragilis (Ellisellidae) (2006) Biochem Syst Ecol, 34, pp. 64-70
  • Chen, W.C., Sheu, J.H., Fang, L.S., Hu, W.P., Sung, P.J., 3a,7a,12a-Triacetoxy-5b-cholanic acid, a steroid from the Formosan soft coral Alcyonium sp (2006) (Alcyoniidae). Nat Prod Res, 20, pp. 748-753
  • Lu, Z., Van Wagoner, R.M., Harper, M.K., Hooper, J.N., Ireland, C.M., Two ring-Aaromatized bile acids from the marine sponge Sollasella moretonensis (2010) Nat Prod Commun, 5 (10), pp. 1571-1574
  • Maneerat, S., Nitoda, T., Kanzaki, H., Kawai, F., Bile acids are new products of a marine bacterium, Myroides sp (2005) Strain SM1. Appl Microbiol Biotechnol, 67, pp. 679-683
  • Dixon, D., Pruski, A., Dixon, L., Jha, A., Marine invertebrate eco-genotoxicology: A methodological overview (2002) Mutagenesis, 17 (6), pp. 495-507
  • Sharma, U., Srivastava, K., Puri, S.K., Singh, C., Amino steroids as antimalarial agents (2008) Med Chem Res, 17, pp. 326-334
  • Brossard, D., El Kihel, L., Clement, M., Sebbahi, W., Khalid, M., Roussakis, Ch., Synthesis of bile acid derivatives and in vitro cytotoxic activity with proapoptotic process on multiple myeloma (KMS-11), glioblastoma multiforme (GBM), and colonic carcinoma (HCT-116) human cell lines (2010) Eur J Med Chem, 45, pp. 2912-2918
  • Tochtrop, G.P., Dekoster, G.T., Cistola, D.P., Covey, D.F., A simple efficient synthesis of 23 24-13C2-labeled bile salts as NMR probes of protein-ligand interactions (2002) Bioorg Med Chem Lett, 12, pp. 433-435
  • Hill, R.A., Kirk, D.N., Makin, H.L., Murphy, G.M., (1991) Dictionary of Steroids, Chemical Data, Structures and Bibliographies, p. 879. , Chapman Hall
  • Mc Gahon, A.S., Martin, R., Bissonnette, A., Mahboubi, Y., Shi, R., Mogil, W., The end of the (cell) line methods for the study of apoptosis in vitro (1995) Method Cell Biol, 46, pp. 153-185
  • Singh, N.M., McCoy, M., Schneider, E., A simple technique for quantitation of low levels of DNA damage in individual cells (1988) Exp Cell Res, 175, pp. 184-191
  • Thakur, N.L., Hentschel, U., Krasko, A., Anil, A.C., Muller, W.E.G., Antibacterial activity of the sponge Suberites domuncula and its primmorphs: Potentia basis for chemical defense (2003) Aqua Microbiol Ecol, 31, pp. 77-83
  • Muller, W.E.G., Schroder, H.C., Wiens, M., Perovic-Ottstadt, S., Batel, R., Muller, I.M., Traditional and modern biomedical prospecting: Part II - The benefits approaches for a sustainable exploitation of biodiversity (secondary metabolites and biomaterials from sponges) (2004) Evid Based Complement Alternat Med, 1 (2), pp. 133-144. , http://dx.doi.org/10.1093/ecam/neh030
  • Thoms, C., Schupp, P., Chemical defense strategies in sponges: A review (2007) Porifera Research: Biodiversity, Innovation and Sustainability, 28. , Custodio MR, Hajdu G, Lobo-Hajdu E, Muricy G, editors. Museu Nacional, Rio de Janeiro: Serie Livros
  • De Flora, S., Bagnasco, M., Bennicelli, C., Camoirano, A., Bojnemirski, A., Kurelec, B., Biotransformation of genotoxic agents in marine sponges. Mechanisms and modulation (1995) Mutagenesis, 10 (4), pp. 357-364
  • Kurelec, B., Krca, S., Pivcevic, B., Ugarković, D., Bachmann, M., Imsiecke, G., Expression of P-glycoprotein gene in marine sponges. Identification and characterization of the 1 125 kDa drug-binding glycoprotein (1992) Carcinogenesis, 13, pp. 69-76
  • Kim, D., Lee, J.S., Kim, J., Kang, S.J., Yoon, J.H., Kim, W.G., Biosynthesis of bile acids in a variety of marine bacterial taxa (2007) J Microbiol Biotechnol, 17, pp. 403-407
  • Sera, Y., Adachi, K., Shizuri, Y., A new epidioxy sterol as an antifouling substance from a palauan marine sponge, Lendenfeldia chondrodes (1999) J Nat Prod, 62 (1), pp. 152-154
  • Singh, K.S., Kaminsky, W., Isolation and X-ray structure of deoxycholic acid from the Sponge Ircinia sp (2011) Nat Prod Commun, 6 (9), pp. 1237-1238
  • Li, H., Shinde, P., Lee, H.J., Yoo, E.S., Lee, C.O., Hong, J., Bile acid derivatives from a sponge-associated Phychrobacter sp (2009) Arch Pharm Res, 32 (6), pp. 857-862
  • Carballo, M.A., Lopez Nigro, M., (2006) Genetica Toxicologica., , De Los Cuatro Vientos (Ed.). Buenos Aires, Argentina

Citas:

---------- APA ----------
Cano, L.P.P., Bartolotta, S.A., Casanova, N.A., Siless, G.E., Portmann, E., Schejter, L., Palermo, J.A.,..., Carballo, M.A. (2013) . Isolation of acetylated bile acids from the sponge Siphonochalina fortis and DNA damage evaluation by the comet assay. Steroids, 78(10), 982-986.
http://dx.doi.org/10.1016/j.steroids.2013.05.020
---------- CHICAGO ----------
Cano, L.P.P., Bartolotta, S.A., Casanova, N.A., Siless, G.E., Portmann, E., Schejter, L., et al. "Isolation of acetylated bile acids from the sponge Siphonochalina fortis and DNA damage evaluation by the comet assay" . Steroids 78, no. 10 (2013) : 982-986.
http://dx.doi.org/10.1016/j.steroids.2013.05.020
---------- MLA ----------
Cano, L.P.P., Bartolotta, S.A., Casanova, N.A., Siless, G.E., Portmann, E., Schejter, L., et al. "Isolation of acetylated bile acids from the sponge Siphonochalina fortis and DNA damage evaluation by the comet assay" . Steroids, vol. 78, no. 10, 2013, pp. 982-986.
http://dx.doi.org/10.1016/j.steroids.2013.05.020
---------- VANCOUVER ----------
Cano, L.P.P., Bartolotta, S.A., Casanova, N.A., Siless, G.E., Portmann, E., Schejter, L., et al. Isolation of acetylated bile acids from the sponge Siphonochalina fortis and DNA damage evaluation by the comet assay. Steroids. 2013;78(10):982-986.
http://dx.doi.org/10.1016/j.steroids.2013.05.020