World Journal of Organic Chemistry
ISSN (Print): 2372-2150 ISSN (Online): 2372-2169 Website: https://www.sciepub.com/journal/wjoc Editor-in-chief: Subrata Shaw
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World Journal of Organic Chemistry. 2016, 4(1), 13-16
DOI: 10.12691/wjoc-4-1-3
Open AccessArticle

Constituents of the Jamaican Sponge Iotrochota birotulata

Monique N. Thompson1 and Winklet A. Gallimore1,

1Department of Chemistry, University of the West Indies, Mona Campus, Kingston, Jamaica

Pub. Date: August 19, 2016

Cite this paper:
Monique N. Thompson and Winklet A. Gallimore. Constituents of the Jamaican Sponge Iotrochota birotulata. World Journal of Organic Chemistry. 2016; 4(1):13-16. doi: 10.12691/wjoc-4-1-3

Abstract

Iotrochota birotulata, an abundantly occurring sponge collected off the coast of Port Royal, Jamaica was investigated to identify its main constituents and evaluate the bioactivity associated with its crude extracts. The compounds renierapurpurin and the tyrosine derivative 1,3-dibromo-5-{2-[(p-hydroxyphenyl)-acetamido]ethyl}-2-[3-(-methyl-2-butenamido)-propoxy] benzene were isolated from the crude extract along with the common steroid β-sitosterol. The carotenoid derivative renierapurpurin was identified in this species for the first time. The structures of these compounds were elucidated using spectral analysis. When the crude extracts of the sponge were tested against the sweet potato weevil Cylas formicarius elegantulus, 100% mortality was observed at a concentration of 2 µg/mL after 72 hours.

Keywords:
Iotrochota birotulata bioassay zebrafish sweet potato weevil

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References:

[1]  Martin, J. V., Koenig, M., McClure, W., Purification and characterization of iotrochotin, a novel toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes, Toxicon, 30(9), 1001-1010, 1992.
 
[2]  Costantino, V., Fattorusso, E., Mangoni, A., Pansini, M., Three New Brominated and Iodinated Tyrosine Derivatives from Iotrochota birotulata, a Non-Verongida Sponge, J. Nat. Prod., 57(11), 1552-1556, 1994.
 
[3]  Muralidhar, P.; Krishna, N., Kumar, M., Rao, C. B., Rao D. V. New Sphingolipids from Marine Sponge Iotrochota baculifera Chem. Pharm. Bull., 51(10), 1193-1195, 2003.
 
[4]  Blunt, J. W., Copp, B. R., Munro, M. H. G., Northcote, P. T., Prinsep, M. R., Marine Natural Products, Nat. Prod. Rep., 20(1), 1-48, 2003.
 
[5]  Faulkner, D. J., Marine Natural Products, Nat. Prod. Rep., 19(1), 1-48, 2002.
 
[6]  Willemsen, P. R., The Screening of Sponge Extracts for Antifouling Activity using a Bioassay with Laboratory-reared Cyprid Larvae of the Barnacle Balanus amphitrite, Int. Biodeterior. Biodegrad. 34(3-4), 361-373, 1994.
 
[7]  Facey, P.C., Porter, R.B., Reese, P. B., Williams, L.A.D., Biological Activity and Chemical Composition of the Essential Oil from Jamaican Hyptis verticillata. J. Agri. Food Chem., 53(12), 4774 -4777, 2005.
 
[8]  Yamaguchi, M., Total Synthesis of Renieratene and Renierapurpurin, Bull. Chem. Soc. Japan, 33(11), 1560-1562, 1960.
 
[9]  Okukado, N. The Structure of Tedanin, A New Carotenoid of Tedania digitata (O. Schmidt), Bull. Chem. Soc. Japan, 48, 1061-1062, 1975.
 
[10]  Dattelbaum, J, Sieg, D., Manieri, C., Thomson, G., Hill, M., Plasticity of Acquired Secondary Metabolites in Clathria prolifera (Demospongia: Poecilosclerida): Putative Photoprotective Role of Carotenoids in a Temperate Intertidal Sponge, The Open Mar. Biol. J., 4(1), 87-95, 2010.
 
[11]  Liaaen-Jensen S., Renstrom, B., Ramdahl, T., Hallenstvet, M., Berquist, P., Carotenoids of Marine Sponges, Biochem. Syst. Ecol., 10(2), 167-174, 1982.