CHEMICAL AND FUNCTIONAL CHARACTERIZATION OF ANTIMICROBIAL METABOLITES ISOLATED FROM THE ASCIDIAN RHOPALAEA BIRKELANDI
DOI:
https://doi.org/10.15359/revmar.3.9Keywords:
Antibiotic activity, ascidians, biological activity, bioactive extractsAbstract
Marine ecosystems have a very large diversity of resources, most of them still partially unknown, and a few others exploited for development of new industrial and toxicological products. The objective of this investigation was to determine whether the acetone extract of the ascidia R. birkelandi from the Pacific coast of Costa Rica showed qualitative antimicrobial activity against the S. aureus bacteria and the G. candidum fungus, and to verify their main secondary metabolites in the active extract using chromatographic and spectroscopic techniques. Ascidians were collected at Tambor, Guanacaste, Costa Rica, between December 2007 and March 2008. Activity against the Gram positive bacteria and fungi was evaluated using ethanolic (95%) and acetonic extracts. Both extracts showed activity against G. candidum; however, only the acetonic extract showed activity against S. aureus. A coumarin and a hydroxyanthraquinone were isolated from a crude extract of R. birkelandi as metabolites present in the active fraction. Purification and isolation were performed by chromatographic techniques and solid phase extraction. Structural information was obtained by spectroscopic analyses: Ultraviolet (UV-Visible), Fourier Transform Infrared (FT-IR), Liquid Chromatography Tandem Mass Spectrometry (LC/MS/MS), Gas Chromatography Mass Spectrometry (GC/MS), Proton Nuclear Magnetic Resonance (1HNMR), and Carbon-13 Magnetic Resonance (13C-NMR). Further studies are recommended for characterization and quantification of the active components of this extract and the possible elucidation of the mechanisms of action.
References
AL-Zereini, W. (2006). Natural products from marine bacteria. (Unpublished doctoral dissertation). University of Kaiserslautern, Germany.
Caccamese, S. R., Azzolina, G., Furnari, M., Cormaci, M., & Grasso S. (1980). Antimicrobial and antiviral activities of extracts from Mediterranean algae. Bot. Mar., 23, 285-288.
Carballo, J. L. (2006). Aportación al conocimiento de la fauna de Ascidias del litoral Pacífico de México. (Informe final SNIB-CONABIO proyecto No. BC005). Universidad Nacional Autónoma de México, Mexico D.F.
Davidson, B. S. (1993). Ascidians: producers of amino acid-derived metabolites. Chem. Rev., 93(5), 1771-1791.
Davies-Coleman, M. T. & Beukes, D. R. (2004). Ten years of marine natural products research at Rhodes University. S. Afr. J. Sci., 100(11, 12), 539-544.
De Lara-Isassi, G. & Ponce-Márquez, M. E. (1991). Detección de la actividad antibacteriana de algunas algas de Playa Paraíso, Veracruz, México. BIOTAM, 3(1), 20-26.
De Lara-Isassi, G., Álvarez-Hernández, S., & Lozano-Ramírez, C. (1996). Actividad antibacteriana de algas marinas de Oaxaca, Pacífico Tropical Mexicano. Rev. Biol. Trop., 44(2), 895-898.
González, F. & Silva, M. (2001). Biodiversidad Química de Macroalgas Marinas. In K. Alveal & T. Antezana (Eds.), Sustentabilidad de la biodiversidad un problema actual bases científico-técnicas, teorizaciones y proyecciones (pp.415-496). Concepción, Chile: Universidad de Concepción.
Hooper, G. J., Davies-Coleman, M. T., & Coetzee, P. S. (1995). New antimicrobial C14 and C13 amines from a South African marine ascidian. Nat. Prod. Lett., 6(1), 31-35.
Issa, H. H., Tanaka, J., Rachmat, R., & Higa, T. (2003). Floresolides, new metacyclophane hydroquinone lactones from an ascidian, Aplidium sp. Tetrahedron Lett., 44(6), 1243-1245.
Jorgensen, J. H., Turnidge, J. D., & Washington, J. A. (1999). Antibacterial susceptibility tests: dilution and disk diffusion methods. In P. R. Murray, E. J. Baron, M. A. Pfaller, F. C. Tenover, & R. H. Yolken (Eds.), Manual of Clinical Microbiology (pp.1526-1543). Washington, DC: American Society for Microbiology.
Joullié, M. M., Leonard, M. S., Portonovo, P., Liang, B., Ding, X., & La Clair, J. J. (2003). Chemical defense in ascidians of the didemnidae family. Bioconjug. Chem., 14(1), 30-37.
Lehrer, R. I., Tincu, J. A., Taylor, S. W., Menzel, L. P., & Waring, A. L. (2003). Natural peptide antibiotics from tunicates: structures, functions and potential uses. Integr. Comp. Biol., 43, 313-322.
Liu, H., Fujiwara, T., Nishikawa, T., Mishima, Y., Nagai, H., Shida, T., Tachibana, K., Kobayashi, H., Mangindaan, R. E. P., & Namikoshi, M. (2005). Lissoclibadins 1-3, three new polysulfur alkaloids, from the ascidian Lissoclinum cf. badium. Tetrahedron Lett., 61(36), 8611-8615.
Makarieva, T. N., Stonik, V. A., Dmitrenok, A. S., Grebnev, B. B., Isakov, V. V., Rebachyk, N M., &. Rashkes, Y. W. (1995). Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycztor sp. J. Nat. Prod., 58(2), 254-258.
McClintock, J. B. & Baker, B. J. (2001). Secondary metabolites from Antarctic marine organisms and their ecological implications. In J. B. McClintock & B. J. Baker (Eds.), Marine Chemical Ecology (pp. 23-25). Florida, USA: CRC Press.
Murti, Y. & Agrawal, T. (2010). Marine derived pharmaceuticals-development of natural health products from marine biodiversity. Int. J. ChemTech Res., 2(4), 2198-2217.
O’Neil, M. J. (2006). The Merck index- an encyclopedia of chemicals, drugs, and biologicals. (14th. ed.) New Jersey, USA: Merck.
Pavia, D. L., Lampman, G. M., Kriz, G. S., & Vyvyan, J. R. (2009). Introduction to spectroscopy. (4rd. ed.). Belmont, CA, USA: Brooks Cole, Cengage, Learning.
Pesando, D. & Caram, B. (1984). Screening of marine algae from the French Mediterranean coast for antibacterial and antifungal activity. Bot. Mar., 27(8), 381-386.
Poumale, H. M. P., Ngadjui, B. T., Helmke, E., & Laatsch, H. (2006). New anthraquinones from a marine Streptomycetes sp. -Isolation, structure determination and biological activities. Z. Naturforsch., 61b(11), 1450-1454.
Proksch, P., Ebel, R., Edrada, R. A., Schupp, P., Lin, W. H., Wray, V., & Steube, K. (2003). Detection of pharmacologically active natural products using ecology. Pure Appl. Chem., 75(2, 3), 343-352.
Rao, P. S. & Parekh, K. S. (1981). Antibacterial activity of Indian seaweed extracts. Bot. Mar., 24(11), 577-582.
Reddy, M. V., Rao, M. R., Rhodes, D., Hansen, M. S., Rubins, K., Bushman, F. D., Venkateswarlu, Y., & Faulkner, D. J. (1999). Lamellarin α 20-sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture. J. Med. Chem., 42(11), 1901-1907.
Rojas, N., Chaves, N., & García, F. (2006). Bacteriología diagnóstica. San José, Costa Rica: Editorial UCR.
Silverstein, R. M., Webster, F. X., & Kiemle, D. J. (2004). Spectrometric identification of organic compounds. (7th ed.). New York, USA: Wiley.
Socha, A. M., García, D., Scheffer, R., & Rowley, D. C. (2006). Antibiotic bisanthraquinone produced by a Streptomycetes isolated from a cyanobacterium associated with Ecteinascidia turbinata. J. Nat. Prod., 69(7), 1070-1073.
Van Name, W. G. (1945). The North and South American ascidians. Bull. Amer. Mus. Nat. Hist., 84, 1-476.
Vidyavathi, N. & Sridhar, K. R. (1991). Seasonal and geographical variation in the antimicrobial activity of seaweeds from the Mangalore coast of India. Bot. Mar., 34(4), 279-284.
Wahl, M., Jensen, P. R., & Fenical, W. (1994). Chemical control of bacterial epibiosis on ascidians. Mar. Ecol. Prog. Ser., 110, 45- 57.
Published
How to Cite
Issue
Section
License
General terms and conditions
Revista Ciencias Marinas y Costeras by Universidad Nacional is located under a Licencia Creative Commons Atribución-NoComercial-SinDerivadas 3.0 Costa Rica.
The journal is hosted in open-access repositories such as the Repositorio Institucional de la Universidad Nacional, the Repositorio Kimuk de Costa Rica and la Referencia.
The editorial source of the journal must be acknowledged. For this purpose, use the doi identifier of the publication.
Self-archiving policy: The journal allows the self-archiving of articles in their refereed version, edited and approved by the Editorial Board of the Journal so that they are available in Open Access through the Internet. More information at the following link: https://v2.sherpa.ac.uk/id/publication/28915
