Marine natural products have attracted the attention of scientists to isolate novel biologically active metabolites. Several promising metabolites were discovered from marine sponges with different biological activities including antimicrobial and anticancer. By far, more than 36% of the metabolites discovered from marine organisms were isolated from sponges. In this study, the alkaloids isolated from marine sponges with antimicrobial activity were described

Althunibat, Osama

Idid, Syed

Majali, Ibrahim

Qaralleh, Haitham

Saad, Shahbudin

Susanti, Deny

English

Journal of Basic and Applied Research in Biomedicine

 1   Qaralleh et al., 2016 J. basic appl. Res 2(1): 1-7                INTRODUCTION  Secondary metabolites are very wide-ranging groups of compounds produced by organisms under certain conditions such as nutrient limitation, defence mechanisms, and regulator molecules (Samuelsson, 2004; Castillo, 2008). In fact, organisms producing secondary metabolites have attracted scientists from different disciplines such as chemistry, pharmacology, and biology. The studies conducted by chemists, pharmacologist, and biologist on secondary metabolites have led to the discovery of thousands of secondary metabolites with promising biological activities (Mayer et al., 2011; Adam and Abdull Rasad, 2015; Majali et al., 2015).   Traditionally, terrestrial plants were the main sources of drugs. Presently, plants still provide many new potent drugs. Until 1950, the research on the chemistry of natural products was limited mainly to the investigation of terrestrial plants. After that, the search for bioactive compounds was extended to microorganisms. For more than 30 years, marine natural products have attracted the attention of scientists to isolate novel biologically active metabolites (Fusetani, 2010; Qaralleh et al., 2010; Shawa et al., 2015).   Marine organisms are not widely used in traditional medicine, but currently they represent an enormous resource for the development of potential therapeutic agents (Pomponi, 1999).  Most of the marine organisms are soft-bodied and they are not able to use mechanical defence mechanisms like shelter or ability to escape, thus they need chemical defence mechanisms to survive (Debitus, 1998). Therefore, they have created an efficient defence mechanism that helps them to survive during evolution and to avoid extinction (Muller et al., 1999). This mechanism encompasses the ability to synthesise or accumulate toxic metabolites and the secretion of highly toxic metabolites as they are rapidly diluted in the ocean water (Haefner, 2003). The metabolites secreted by marine organisms are characterised by the presence of halogen unlike the terrestrial secondary metabolites (Rinehart, 1992; Faulkner, 2002). For these reasons, and because of the high biological diversity in the sea (Mayer and Lehmann, 2000; Proksch et al., 2002), marine organisms have attracted researchers to find useful drugs for mankind (Satheeshkumar et al., 2010).  Therefore, the aim of this paper is to review the antimicrobial alkaloids isolated from marine sponges, primarily focusing on their phytochemical characteristics.  Sponges Sponges represent the major rich organisms with promising active pharmaceutical metabolites. The interest for drugs discovery in sponges has started since 1950s due to the discovery of the nucleosides spongothymidine and spongouridine from the marine sponge Cryptotethya crypta (Laport et al., 2009). Both metabolites were later developed to ara-C, the first marine-derived anticancer agent, and the antiviral drug ara-A (Proksch et al., 2002). Later, several promising metabolites were discovered from marine sponges with different biological activities including antimicrobial and anticancer (Kobayashi, 2000). By far, more than 36% of the metabolites discovered from marine organisms were isolated from sponges. Sponge crude extracts showed variable antimicrobial activities against terrestrial pathogenic bacteria, and against marine bacteria. Reports have shown that terrestrial microbes are more sensitive than marine microbes (Becerro et al., 1994; Newbold et al., 1999). Due to the presence of antimicrobial substances, sponges are rarely infected by exogenous microbes (Newbold et al., 1999). Antimicrobial alkaloids isolated from marine sponges-MINIREVIEW   Haitham Qaralleh1*, Syed Z. Idid2, Shahbudin Saad3, Deny Susanti2, Osama Y. Althunibat4, Ibrahim Majali5  1Department of Medical Support, Al-karak University College, Al-Balqa' Applied University, Jordan. 2Department of Biomedical Science, Faculty of Science, International Islamic University Malaysia, Kuantan, Pahang, Malaysia 3Institute of Oceanography and Maritime Studies, Faculty of Science, International Islamic University Malaysia, Kuantan, Pahang, Malaysia 4Department of Laboratory Medical Sciences, Princess Aisha Bent Al-Hussein Faculty of Nursing & Health Sciences, Al Hussein bin Talal University, Jordan.  5Al-Ghad International College for Applied Medical Sciences, Tabuk, Saudia Arabia.  *corresponding author: haithym2006@yahoo.com   Abstract: Marine natural products have attracted the attention of scientists to isolate novel biologically active metabolites. Several promising metabolites were discovered from marine sponges with different biological activities including antimicrobial and anticancer. By far, more than 36% of the metabolites discovered from marine organisms were isolated from sponges. In this study, the alkaloids isolated from marine sponges with antimicrobial activity were described.  Received: 20-12-2015 Revised: 14-1-2016 Published: 17-1-2016   Keywords: Alkaloids,  Sponges,  Antimicrobial activity  Qaralleh et al., 2016, J. basic appl. Res 2(1): 1-7  2  Table 1: Antimicrobial alkaloids isolated from marine sponges Metabolites Inhibited Microorganisms References Arenosclerins A, B, C (1-3) and haliclonacyclamine E (4) S. aureus  Torres et al. (2002) Nagelamide A (5) Micrococcus luteus, Bacillus subtilis, and E. coli  Endo et al. (2004) Cribrostatin 6 (6) S. pneumoniae  Pettit et al. (2004) Purpuramine L (7)  S. aureus, B. subtilis, and Chromobacterium violaceum  Goud et al. (2003) Ptilocaulis guanidine (8) S. aureus  Yang et al. (2003a) Isoaaptamine (9) S. aureus  Jang et al. (2007a) Deoxytopsentin (10) S. aureus  Oh et al. (2005) Hamacanthin A (11) S. aureus  Oh et al. (2005) Batzellaside A (12) Staphylococcus epidermidis  Segraves and Crews, (2005) Dendridine A (13)  B. subtilis and Micrococcus luteus  Tsuda et al. (2005) Batzelladine L and M (14, 15)  S. aureus and methicillin resistant S. aureus  Hua et al. (2007) Massadine (16) C. albicans  Nishimura et al. (2003) Naamine G (17) Cladosporium herbarum  Hassan et al. (2004)  The studies on screenings of marine organisms for antimicrobial activity lead to the isolation and characterisation of a wide range of bioactive metabolites.   More than 800 antibiotic metabolites have been isolated from marine sponges (Torres et al., 2002), and new metabolites are being discovered every year. A total of 62 metabolites from marine sponges with potent antimicrobial activity were reported in the literature within the period of 2001 to 2008 (Mayer and Hamann, 2005; Mayer et al., 2007; 2009; 2011; Majali et al., 2015). As the secondary metabolite composition of sponges is dominated by alkaloid and terpenes metabolites, it is not surprising that antimicrobial sponge natural products are also dominated by polyketide and sterol-derived metabolites.    ALKALOIDS  Heterocyclic nitrogen compounds are called alkaloids. Alkaloids are well-known for their antimicrobial activity. The occurrence of active antimicrobial alkaloids in sponges is widespread. As shown in Table 1, many potent antimicrobial alkaloids were isolated from marine sponges.  Torres et al. (2002) reported that the metabolites of arenosclerins A, B, C (1-3) and haliclonacyclamine E (4) were isolated from Arenosclera brasiliensis. These isolated alkaloids showed potent antibiotic activity against antibiotic-resistant S. aureus (MIC = 5 - 400 µg/mL).   NNHHOH  Arenosclerin A (1)   A dimeric bromopyrrole alkaloid, nagelamide G (5) was isolated from Agelas sp. (Endo et al., 2004). Nagelamide G exhibited antibacterial activity against M. luteus, B. subtilis, and E. coli. Gram-positive alkaloid inhibitor was reported for cribrostatin 6 (6), which was isolated from Cribochalina sp. sponge (Pettit et al., 2004). The maximum activity for Cribostatin 6 was reported against Streptococcus pneumoniae (MIC = 0.5 μg/mL).    Qaralleh et al., 2016, J. basic appl. Res 2(1): 1-7  3   NNHHOH Arenosclerin B (2)  NNHH Arenosclerin C (3) NNHHOH  Haliclonacyclamine E (4)   NHBrBrNHONHBrBrNHONNHNH2NHNNH2 Nagelamide (5)  NNOOO Cribrostatin 6 (6)    Goud et al. (2003) reported the isolation of purpuramine L (7) from Psammaplysilla purpurea. This alkaloid showed potent inhibition activity against S. aureus, B. subtilis, and C. violaceum.    Yang et al. (2003a) reported bicyclic guanidine alkaloid (8) from Ptilocaulis spiculifer. Interestingly, the inhibition activity of 50 μg guanidine alkaloid was as potent as 10 μg gentamicin.   Jang et al. (2007a) reported the isolation of the alkaloid isoaaptamine (9) from the marine sponge Aaaptos aaptos. Isoaaptamine showed potent antimicrobial activity against S. aureus.          Qaralleh et al., 2016, J. basic appl. Res 2(1): 1-7  4   BrNN OBrBr NH2OOHMeO  Purpuramine L (7)   NONNNH2ONHNH2H    Guanidine alkaloid (8) MeNNOHMeO Isoaaptamine (9)  The bis(indole) alkaloids deoxytopsentin (10) and hamacanthin A (11) showed potent antibacterial activity against S. aureus (MIC = 3.12 - 6.35 μg/mL). These alkaloids were isolated from the marine sponge Spongosorites sp (Oh et al., 2005).   NHNHONHN deoxytopsentin (10) NHNNHNHBrOBr Hamacanthin A (11)  Potent marine antibacterial alkaloid was reported from the sponge Batzella sp. The isolated batzellaside A (12) showed promising antimicrobial activity against several antibiotic-resistant bacterial strains with MICs less than 10 μg/mL (Segraves and Crews, 2005).   Three other alkaloids were reported with MIC less than 10 μg/mL including dendridine A (13) that were isolated from the sponge Dictyodendrilla sp. (Tsuda et al., 2005) and the alkaloids batzelladines L and M (14, 15) isolated from the Caribbean sponge Monanchora unguifera.  OHOHOHNHOH Batzellaside A (12)    Qaralleh et al., 2016, J. basic appl. Res 2(1): 1-7  5   NH OHBrNHNH2BrNH2OH     Dendridine A (13)  NHNNH HNHNNOOH(CH2)8CH3H Batzelladines L (14)  NHNNOOH(CH2)6CH3NHNNH H Batzelladines M (15)   Only two alkaloids that showed antifungal activities were isolated from marine sponge in the period between 2001 and 2008.   The alkaloid massadine (16), which was isolated from the marine sponge Stylissa aff. massa, showed promising inhibition activity against C. albicans.   Imidazole alkaloid named naamine G (17) was isolated from the sponge Leucetta chagosensis. Naamine G exhibited strong antifungal activity against Cladosporium herbarum (Hassan et al., 2004). 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Antimicrobial alkaloids isolated from marine sponges-MINIREVIEW

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Antimicrobial alkaloids isolated from marine sponges-MINIREVIEW

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