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Halogenated Alkaloids of Agelas Sponges

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Halogenated Alkaloids of Agelas Sponges Indonesian J. Pharm. Vol. 25 No. 4 : 199 – 222 ISSN-p : 2338-9427 DOI: 10.14499/indonesianjpharm25iss4pp199 Review Article NEW HOPE ON DRUG LEADS DEVELOPMENT FROM DEEP OCEAN: HALOGENATED ALKALOIDS OF AGELAS SPONGES Triana Hertiani Faculty of Pharmacy, ABSTRACT Universitas Gadjah Mada, Agelas sponge is found in abundancy from Indonesia’s Sekip Utara, Yogyakarta, ocean. This sponge produces an important chemotaxonomic group Indonesia 55281 of compounds, derived from pyrrole-imidazole alkaloids. This group of compounds is one of those exclusively found from marine Submitted: 04-05-2014 environment. Marine sponges are reported to be promising drug Revised: 05-07-2014 lead producers having unique chemical structures of which many Accepted: 08-09-2014 have no terrestrial counterparts. The objective of this report is to give an overview of the reported attempts from up to down stream *Corresponding author to develop pyrrole-imidazole alkaloids as new drug lead. Literatures Triana Hertiani up to 2013 reporting this group of compounds from Agelas sponges were studied. Discussion on the halogenated alkaloids covers the Email : [email protected] producers, description of high chemical diversity, identification, biosynthesis and ecological relevance as well as their role as a promising drug candidate. Alternatives to provide continous supplies for drug development are also discussed considering that wild harvesting of the sponge producers can lead to ecological damage in the future . Broad range of interesting pharmacological importance as well as several success in developing synthetic route for production supports its development as drug candidate. Key words: Agelas, halogenated alkaloids, drug lead, sponge INTRODUCTION also clinical trials which can be expected that A coverage of almost 75% of the Earth‟s the number will increase in the near future surface has positioned the ocean as the major (Amador et al., 2003). producer of natural products (Whitehead, According to Proksch and co-workers 1999). Unlike its terrestrial counterpart, unique (2002), the majority of marine natural products structures has been encountered and the currently in clinical trial or under clinical utilization has lack of ethno-medical history. evaluation are produced by invertebrates. The This issue together with technical difficulties in soft bodied, sessile or slow-moving marine collecting marine organisms held back the invertebrates having lack of morphological development of marine-derived natural products defense structure in form of spines or a as therapeutic agents. Nevertheless, synergism protective shell make them more vulnerable for collaboration involving pharmaceutical predation which justifies the ecological companies, academic institutions, governmental importance of utilizing chemical constituents and so non-governmental agencies, has made a for surveillance in the respective invertebrates significant progress in form of systemic (Proksch et al., 2002). investigations directed towards the collection Database provided by MarinLit (2002) and characterizations of marine natural shows that the source of new marine natural products, as well as the evaluation of their products is dominated by sponges (37%) biological activity (Christian et al., 1997; followed by coelenterates (21%). Blunt et al. in Amador et al., 2003). Large numbers of novel a review of marine natural products (2005) and marine-derived compounds reported in the Hu et al. (2011) supported the above mentioned literatures in the last decades exhibit the statement. This data somehow define the role positive development (Mayer and Gustafson, of marine invertebrates as a potential source of 2003; Amador et al., 2003). Some promising new drug candidates. Up to now more than agents which are naturally derived or the 17,000 marine products have been described synthetic derivates have entered preclinical and (MarinLit, 2006) of which sponges are Volume 25 Issue 4 (2014) 199 Halogenated Alkaloids of Agelas Sponges responsible for more than 5300 different Murti, 2006; Eder et al., 1999), and A. products (Faulkner 2000, 2001, 2002). nemoecinata (Pedradab, 2005) were examples of Moreover, the chemical diversity of sponge secondary metabolite producers from the products is remarkable, in addition to the Agelas collected from Indonesia sea, of which unusual nucleosides, bioactive terpenes, sterols, A. nakamurai as the most reported sponge from cyclic peptides, alkaloids, fatty acids, peroxides, this genus (Hertiani et al., 2010; Murti, 2001, and amino acid derivatives (which are 2006; Sapar et al., 2013; Eder et al., 1999; frequently halogenated) (Sipkema et al., 2005). Trianto, 2005). Several other reports on this Pharmaceutical interest in sponges itself particular sponge are also derived from the was aroused in the early 1950s by the discovery neighbour sea, Papua New Guinea (Iwagawa et of the unusual nucleosides spongothymidine al., 1998). Many pharmacological-interesting and spongouridine in the marine sponge compounds found in these particular sponges Cryptotethia crypta (Bergmann and Feeney, 1950, including the marine specific halogenated 1951). These nucleosides were the basis for the alkaloids. synthesis of Ara-C, the first marine-derived anticancer agent, and the antiviral drug Ara-A Halogen containing metabolites (Prokch et al., 2002). Marine sponges are a rich source of As also found in terrestrial metabolites, highly halogenated compounds. They may many of marine natural products act as function to resist feeding by fish and fouling by regulators of specific biological functions. barnacles, bacteria, and fungi (Gribble, 2004). Some of them have pharmacological activity One of the widest group of halogenated due to their specific interactions with receptors alkaloids are bromine-containing alkaloids and enzymes which are not found in their (Dembitsky and Tolstikov, 2003). High halogen terestral counterpart. Marine metabolites face concentration in sea water has a consequence the problem that they become immediately of its contribution in the biosynthesis of some diluted by large volumes of seawater of which marine metabolites. Catalyzed by haloperoxi- requires a highly potency on a molecular basis dases, halogenide anions from sea-water are and retains a relatively low solubility oxidized (Hoffmann and Lindel, 2003) and (McConnel et al., 1994). It has been repeatedly then incorporated into organic compounds by shown that the accumulation of toxic or specific halogenases (Van Pee, 2001). distasteful natural product is an effective Enormous reactivity towards electrophilic strategy to repel potential predators (e.g. fishes) halogenation reactions is probably the cause or in a competition for living space (Proksch et why heteroatom containing secondary al., 2002; Proksch and Ebel, 1998; Proksch, metabolites such as pyrroles, indoles, phenols, 1999; McClintock and Baker, 2001). These and tyrosines are commonly found to be secondary metabolites, which are produced as a halogenated in sponges. Despite the relative result of evolutionary pressures to reserve or concentrations of chloride, bromide and iodide enhance an organisms ecological success ions exist in sea water (559mM, 0.86mM and (Proksch, 1999), have evolved into structurally 0.45M respectively); marine organisms oxidize diverse and usually stereo-chemically complex more bromide than chloride for incorporation compounds with specific biological activity into organic compounds (Faulkner, 1995). This (Edrada et al., 2000) many of which belong to may reflect the higher importance of novel chemical groups solely found in marine bromoperoxidase (BPO) relative to chloro- environment (Carte, 1993). peroxidase (CPO) in marine life, and underline The Agelas sponges classification falls the fact that chlorine cannot be oxidized to into phylum Porifera; class Demospongiae; active chlorine by BPO (Gribble, 1996b, 1998). order Agelasida; family Agelasidae and genus Therefore bromide ions have greater ease to be Agelas. This sponge found in abundance in oxidized and give bromonium species which Indonesia suggesting evolutionary fittness. react readily as electrophils with unsaturated Agelas linnaei, A. nakamurai (Hertiani et al., 2010; species (Whitehead, 1999). 200 Volume 25 Issue 4 (2014) Triana Hertiani Brominated pyrroles have been isolated A distinct pseudomolecular ion pattern on several occasions as major constituents of of brominated compounds in LC/MS is very marine sponges. Many of the simpler members important for preliminary characterization. This of this class of compounds are structurally method can easily distinguish the presence of related as they comprise two heterocyclic rings different brominated metabolites from sponge linked by a linear chain (Whitehead, 1999). crude extracts. In LC/MS, after having the Over the last thirty years, numerous similar HPLC separation, the resulted peaks are alkaloids with various structures and interesting detected by the UV detector and mass biological activities have been isolated spectrometer. As more compounds can share essentially (but not exclusively) from various the same UV pattern, the possibility of sharing species of Agelasidae, Hymeniacidonidae and the same molecular weight is less. In the case of Axinellidae (Williams and Faulkner, 1996). brominated compounds, it is very rare to find different compounds having the same Characterization of halogenated molecular weight with the same degree of alkaloids by LC/MS bromination. The presence of bromine and chlorine in a molecule can
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