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1

Sfecci, Estelle, Thierry Lacour, Philippe Amade, and Mohamed Mehiri. "Polycyclic Guanidine Alkaloids from Poecilosclerida Marine Sponges." Marine Drugs 14, no. 4 (April 9, 2016): 77. http://dx.doi.org/10.3390/md14040077.

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2

Yasuda, Tetsuro, Atsushi Araki, Takaaki Kubota, Junji Ito, Yuzuru Mikami, Jane Fromont, and Jun’ichi Kobayashi. "Bromopyrrole Alkaloids from Marine Sponges of the GenusAgelas⊥." Journal of Natural Products 72, no. 3 (March 27, 2009): 488–91. http://dx.doi.org/10.1021/np800645q.

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3

Laville, Rémi, Olivier P. Thomas, Fabrice Berrué, Diana Marquez, Jean Vacelet, and Philippe Amade. "Bioactive Guanidine Alkaloids from Two Caribbean Marine Sponges." Journal of Natural Products 72, no. 9 (September 25, 2009): 1589–94. http://dx.doi.org/10.1021/np900244g.

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4

Elissawy, Ahmed M., Ebrahim Soleiman Dehkordi, Negin Mehdinezhad, Mohamed L. Ashour, and Pardis Mohammadi Pour. "Cytotoxic Alkaloids Derived from Marine Sponges: A Comprehensive Review." Biomolecules 11, no. 2 (February 10, 2021): 258. http://dx.doi.org/10.3390/biom11020258.

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Marine sponges (porifera) have proved to be a prolific source of unique bioactive secondary metabolites, among which the alkaloids occupy a special place in terms of unprecedented structures and outstanding biological activities. Identification of active cytotoxic alkaloids extracted from marine animals, particularly sponges, is an important strive, due to lack of knowledge on traditional experiential and ethnopharmacology investigations. In this report, a comprehensive survey of demospongian bioactive alkaloids in the range 1987–2020 had been performed with a special emphasis on the potent cytotoxic activity. Different resources and databases had been investigated, including Scifinder (database for the chemical literature) CAS (Chemical Abstract Service) search, web of science, Marin Lit (marine natural products research) database. More than 230 representatives of different classes of alkaloids had been reviewed and classified, different genera belonging to the phylum porifera had been shown to be a prolific source of alkaloidal molecules, including Agelas sp., Suberea sp., Mycale sp., Haliclona sp., Epipolasis sp., Monanchora sp., Crambe sp., Reniera sp., and Xestospongia sp., among others. The sufficient production of alkaloids derived from sponges is a prosperous approach that requires more attention in future studies to consider the constraints regarding the supply of drugs, attained from marine organisms.
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Tanaka, Naonobu, Rei Momose, Azusa Takahashi-Nakaguchi, Tohru Gonoi, Jane Fromont, and Jun'ichi Kobayashi. "Hyrtimomines, indole alkaloids from Okinawan marine sponges Hyrtios spp." Tetrahedron 70, no. 4 (January 2014): 832–37. http://dx.doi.org/10.1016/j.tet.2013.12.032.

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6

Tanaka, N., T. Kusama, Y. Kashiwada, and J. Kobayashi. "Agelamadins, bromopyrrole alkaloids from Okinawan marine sponges Agelas spp." Planta Medica 81, S 01 (December 14, 2016): S1—S381. http://dx.doi.org/10.1055/s-0036-1596645.

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7

Lee, Sanghoon, Naonobu Tanaka, Sakura Takahashi, Daisuke Tsuji, Sang-Yong Kim, Mareshige Kojoma, Kohji Itoh, Jun’ichi Kobayashi, and Yoshiki Kashiwada. "Agesasines A and B, Bromopyrrole Alkaloids from Marine Sponges Agelas spp." Marine Drugs 18, no. 9 (August 30, 2020): 455. http://dx.doi.org/10.3390/md18090455.

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Exploration for specialized metabolites of Okinawan marine sponges Agelas spp. resulted in the isolation of five new bromopyrrole alkaloids, agesasines A (1) and B (2), 9-hydroxydihydrodispacamide (3), 9-hydroxydihydrooroidin (4), and 9E-keramadine (5). Their structures were elucidated on the basis of spectroscopic analyses. Agesasines A (1) and B (2) were assigned as rare bromopyrrole alkaloids lacking an aminoimidazole moiety, while 3–5 were elucidated to be linear bromopyrrole alkaloids with either aminoimidazolone, aminoimidazole, or N-methylated aminoimidazole moieties.
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8

Li, Fengjie, Michelle Kelly, and Deniz Tasdemir. "Chemistry, Chemotaxonomy and Biological Activity of the Latrunculid Sponges (Order Poecilosclerida, Family Latrunculiidae)." Marine Drugs 19, no. 1 (January 9, 2021): 27. http://dx.doi.org/10.3390/md19010027.

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Marine sponges are exceptionally prolific sources of natural products for the discovery and development of new drugs. Until now, sponges have contributed around 30% of all natural metabolites isolated from the marine environment. Family Latrunculiidae Topsent, 1922 (class Demospongiae Sollas, 1885, order Poecilosclerida Topsent, 1928) is a small sponge family comprising seven genera. Latrunculid sponges are recognized as the major reservoirs of diverse types of pyrroloiminoquinone-type alkaloids, with a myriad of biological activities, in particular, cytotoxicity, fuelling their exploration for anticancer drug discovery. Almost 100 pyrroloiminoquinone alkaloids and their structurally related compounds have been reported from the family Latrunculiidae. The systematics of latrunculid sponges has had a complex history, however it is now well understood. The pyrroloiminoquinone alkaloids have provided important chemotaxonomic characters for this sponge family. Latrunculid sponges have been reported to contain other types of metabolites, such as peptides (callipeltins), norditerpenes and norsesterpenes (trunculins) and macrolides (latrunculins), however, the sponges containing latrunculins and trunculins have been transferred to other sponge families. This review highlights a comprehensive literature survey spanning from the first chemical investigation of a New Zealand Latrunculia sp. in 1986 until August 2020, focusing on the chemical diversity and biological activities of secondary metabolites reported from the family Latrunculiidae. The biosynthetic (microbial) origin and the taxonomic significance of pyrroloiminoquinone related alkaloids are also discussed.
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9

Li, Fengjie, Michelle Kelly, and Deniz Tasdemir. "Chemistry, Chemotaxonomy and Biological Activity of the Latrunculid Sponges (Order Poecilosclerida, Family Latrunculiidae)." Marine Drugs 19, no. 1 (January 9, 2021): 27. http://dx.doi.org/10.3390/md19010027.

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Marine sponges are exceptionally prolific sources of natural products for the discovery and development of new drugs. Until now, sponges have contributed around 30% of all natural metabolites isolated from the marine environment. Family Latrunculiidae Topsent, 1922 (class Demospongiae Sollas, 1885, order Poecilosclerida Topsent, 1928) is a small sponge family comprising seven genera. Latrunculid sponges are recognized as the major reservoirs of diverse types of pyrroloiminoquinone-type alkaloids, with a myriad of biological activities, in particular, cytotoxicity, fuelling their exploration for anticancer drug discovery. Almost 100 pyrroloiminoquinone alkaloids and their structurally related compounds have been reported from the family Latrunculiidae. The systematics of latrunculid sponges has had a complex history, however it is now well understood. The pyrroloiminoquinone alkaloids have provided important chemotaxonomic characters for this sponge family. Latrunculid sponges have been reported to contain other types of metabolites, such as peptides (callipeltins), norditerpenes and norsesterpenes (trunculins) and macrolides (latrunculins), however, the sponges containing latrunculins and trunculins have been transferred to other sponge families. This review highlights a comprehensive literature survey spanning from the first chemical investigation of a New Zealand Latrunculia sp. in 1986 until August 2020, focusing on the chemical diversity and biological activities of secondary metabolites reported from the family Latrunculiidae. The biosynthetic (microbial) origin and the taxonomic significance of pyrroloiminoquinone related alkaloids are also discussed.
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10

Bjoersvik, Hans-Rene, and Alexander H. Sandtorv. "ChemInform Abstract: Synthesis of Imidazole Alkaloids Originated in Marine Sponges." ChemInform 45, no. 42 (October 2, 2014): no. http://dx.doi.org/10.1002/chin.201442268.

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11

Tanaka, Naonobu, Taishi Kusama, Yoshiki Kashiwada, and Jun’ichi Kobayashi. "Bromopyrrole Alkaloids from Okinawan Marine Sponges Agelas spp." Chemical and Pharmaceutical Bulletin 64, no. 7 (2016): 691–94. http://dx.doi.org/10.1248/cpb.c16-00245.

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12

Novanna, M., K. R. Ethiraj, and S. Kannadasan. "An Overview of Synthesis of Indole Alkaloids and Biological Activities of Secondary Metabolites Isolated from Hyrtios Species." Mini-Reviews in Medicinal Chemistry 19, no. 3 (January 11, 2019): 194–205. http://dx.doi.org/10.2174/1389557518666181102110537.

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Marine sponges are a rich source of more than 50% of marine natural compounds that have been isolated from marine organisms. This review article is focused on the importance of biologically active and pharmaceutically important secondary metabolites extracted from one of the important classes of marine sponge Hyrtios sp. This review also deals with reported synthetic routes of some indole alkaloids extracted from the marine sponge Hyrtios sp. A range of bioactivities displayed by indole-based alkaloids is described.
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13

Souza, Cássio R. M., Wallace P. Bezerra, and Janeusa T. Souto. "Marine Alkaloids with Anti-Inflammatory Activity: Current Knowledge and Future Perspectives." Marine Drugs 18, no. 3 (March 2, 2020): 147. http://dx.doi.org/10.3390/md18030147.

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Alkaloids are nitrogenous compounds with various biological activities. Alkaloids with anti-inflammatory activity are commonly found in terrestrial plants, but there are few records of the identification and characterization of the activity of these compounds in marine organisms such as fungi, bacteria, sponges, ascidians, and cnidarians. Seaweed are a source of several already elucidated bioactive compounds, but few studies have described and characterized the activity of seaweed alkaloids with anti-inflammatory properties. In this review, we have gathered the current knowledge about marine alkaloids with anti-inflammatory activity and suggest future perspectives for the study and bioprospecting of these compounds.
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14

Tanaka, Naonobu, Rei Momose, Azusa Takahashi-Nakaguchi, Tohru Gonoi, Jane Fromont, and Jun'ichi Kobayashi. "ChemInform Abstract: Hyrtimomines, Indole Alkaloids from Okinawan Marine Sponges Hyrtios spp." ChemInform 45, no. 28 (June 26, 2014): no. http://dx.doi.org/10.1002/chin.201428215.

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15

Salmoun, Mostafa, Christine Devijver, Désiré Daloze, Jean-Claude Braekman, and Rob W. M. van Soest. "5-Hydroxytryptamine-Derived Alkaloids from Two Marine Sponges of the GenusHyrtios." Journal of Natural Products 65, no. 8 (August 2002): 1173–76. http://dx.doi.org/10.1021/np020009+.

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16

Braekman, J. C., D. Daloze, R. Tavares, E. Hajdu, and R. W. M. Van Soest. "Novel Polycyclic Guanidine Alkaloids from Two Marine Sponges of the GenusMonanchora." Journal of Natural Products 63, no. 2 (February 2000): 193–96. http://dx.doi.org/10.1021/np990403g.

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17

Lee, Yeon-Ju, Yeonwoo Cho, and Huynh Nguyen Khanh Tran. "Secondary Metabolites from the Marine Sponges of the Genus Petrosia: A Literature Review of 43 Years of Research." Marine Drugs 19, no. 3 (February 25, 2021): 122. http://dx.doi.org/10.3390/md19030122.

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Sponges are prolific sources of various natural products that have provided the chemical scaffolds for new drugs. The sponges of the genus Petrosia inhabit various regions and contain a variety of biologically active natural products such as polyacetylenes, sterols, meroterpenoids, and alkaloids. This review aims to provide a comprehensive summary of the chemical structures and biological activities of Petrosia metabolites covering a period of more than four decades (between 1978 and 2020). It is also described in this review that the major groups of metabolites from members of the genus Petrosia differed with latitude. The polyacetylenes were identified to be the most predominant metabolites in Petrosia sponges in temperate regions, while tropical Petrosia species were sources of a greater variety of metabolites, such as meroterpenoids, sterols, polyacetylenes, and alkaloids.
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18

Hu, Jin-Feng, Jiangnan Peng, Abul B. Kazi, Michelle Kelly, and Mark T. Hamann. "Bromopyrrole Alkaloids from the Jamaican Sponge Didiscus Oxeata." Journal of Chemical Research 2005, no. 7 (July 2005): 427–28. http://dx.doi.org/10.3184/030823405774309113.

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Three bromopyrrole alkaloids (1–3) were isolated from the acetone extracts of Didiscus oxeata during chemical and biological investigation of Caribbean and Indo-Pacific marine sponges. The structures were established by spectroscopic methods. Mukanadin D (3) was obtained for the first time as a naturally-occurring C11 bromopyrrole alkaloid.
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19

Sahidin, Idin, Carla W. Sabandar, Wahyuni, Rini Hamsidi, Sandra Aulia Mardikasari, Wa Ode Sitti Zubaydah, Baru Sadarun, Wa Ode Sitti Musnina, Ahmad Darmawan, and Andini Sundowo. "Investigation of Compounds and Biological Activity of Selected Indonesian Marine Sponges." Natural Products Journal 10, no. 3 (June 16, 2020): 312–21. http://dx.doi.org/10.2174/2210315509666190627105237.

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Background: Marine sponges provided a great source of natural products with promising biological activity. This study was aimed to investigate the chemical constituents of methanol extracts of selected Indonesian marine sponges (Callyspongia sp., Clathria sp., Melophlus sarasinorum, and Xestospongia sp.), collected from the Saponda Islands, Southeast Sulawesi, Indonesia as well as to evaluate their antimicrobial and antioxidant activities. Methods: LCMS/MS analysis used to identify the compounds. Agar well diffusion and DPPH assays were used to evaluate the antimicrobial and antioxidant activities. Results: Chemical screening reported alkaloids, terpenoids, steroids, and saponins from all investigated sponges. The LC-MS/MS analysis identified various compounds which mainly contained steroids. Antimicrobial activity (against Bacillus subtilis, Escherichia coli, Salmonella enterica, and Candida albicans) was only shown by the Xestospongia sp. extract. Meanwhile, extracts of M. sarasinorum, Xestospongia sp., and Callyspongia sp. exhibited potent radical scavenging activity. Conclusion: The study concluded that the selected sponges could provide various groups of compounds. Methanol extracts of these sponges could be used as sources of antimicrobial and antioxidant agents.
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20

El-Naggar, Mohamed, and Robert J. Capon. "Discorhabdins Revisited: Cytotoxic Alkaloids from Southern Australian Marine Sponges of the GeneraHigginsiaandSpongosorites†." Journal of Natural Products 72, no. 3 (March 27, 2009): 460–64. http://dx.doi.org/10.1021/np8007667.

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21

Hassan, Wafaa, Ehab S. Elkhayat, Ru AnGelie Edrada, Rainer Ebel, and Peter Proksch. "New Bromopyrrole Alkaloids from the Marine Sponges Axinella Damicornis and Stylissa Flabelliformis." Natural Product Communications 2, no. 11 (November 2007): 1934578X0700201. http://dx.doi.org/10.1177/1934578x0700201121.

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Investigation of the tropical sponges Axinella damicornis and Stylissa flabelliformis, family Axinillidae, afforded five new bromopyrrole alkaloids (1–5) and thirteen known compounds (6–18). Semi synthesis of 5 was carried out in order to confirm its structure. The structures of the isolated compounds were elucidated using 1D- and 2D-NMR spectroscopy and mass spectrometry. The cytotoxicity, antimicrobial and protein-kinase inhibition activities were tested for the isolated compounds.
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22

Silva, Siguara B. L., François Oberhänsli, Marie-Aude Tribalat, Grégory Genta-Jouve, Jean-Louis Teyssié, Marie-Yasmine Dechraoui-Bottein, Jean-François Gallard, Laurent Evanno, Erwan Poupon, and Olivier P. Thomas. "Insights into the Biosynthesis of Cyclic Guanidine Alkaloids from Crambeidae Marine Sponges." Angewandte Chemie 131, no. 2 (December 6, 2018): 530–35. http://dx.doi.org/10.1002/ange.201809539.

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23

Silva, Siguara B. L., François Oberhänsli, Marie-Aude Tribalat, Grégory Genta-Jouve, Jean-Louis Teyssié, Marie-Yasmine Dechraoui-Bottein, Jean-François Gallard, Laurent Evanno, Erwan Poupon, and Olivier P. Thomas. "Insights into the Biosynthesis of Cyclic Guanidine Alkaloids from Crambeidae Marine Sponges." Angewandte Chemie International Edition 58, no. 2 (December 6, 2018): 520–25. http://dx.doi.org/10.1002/anie.201809539.

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24

Utkina, N. K. "Antioxidant activityofaromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios SP." Chemistry of Natural Compounds 45, no. 6 (November 2009): 849–53. http://dx.doi.org/10.1007/s10600-010-9490-z.

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25

Supriyono, A., B. Schwarz, V. Wray, L. Witte, W. E. G. Müller, R. van Soest, W. Sumaryono, and P. Proksch. "Bioactive Alkaloids from the Tropical Marine Sponge Axinella carteri." Zeitschrift für Naturforschung C 50, no. 9-10 (October 1, 1995): 669–74. http://dx.doi.org/10.1515/znc-1995-9-1012.

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Abstract Analysis of the tropical marine sponge Axinella carteri afforded six unusual alkaloids, including the new brominated guanidine derivative 3-bromo-hymenialdisine. The structure elucidation of the new alkaloid is described. The alkaloid patterns of sponges collected in Indonesia or in the Philippines were shown to be qualitatively identical suggesting de novo synthesis by the sponge or by endosymbiontic microorganisms rather than uptake by filterfeeding. All alkaloids were screened for insecticidal activity as well as for cytotoxicity. The guanidine alkaloids hymenialdisine and debromohymenialdisine exhibited insecticidal activity towards neonate larvae of the polyphagous pest insect Spodoptera littoralis (LD50s of 88 and 125 ppm, respectively), when incorporated into artificial diet and offered to the larvae in a chronic feeding bioassay. The remaining alkaloids, including the new compound, were inactive in this bioassay. Cytotoxicity was studied in vitro using L5178y mouse lymphoma cells. Debromohymenialdisine was again the most active compound (ED50 1.8 μg/ml) followed by hymenialdisine and 3-bromohymenialdisine, which were essentially equitoxic and exhibited ED50s of 3.9 μg/ml in both cases. The remaining alkaloids were inactive against this cell line
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26

KELECOM, ALPHONSE. "Secondary metabolites from marine microorganisms." Anais da Academia Brasileira de Ciências 74, no. 1 (March 2002): 151–70. http://dx.doi.org/10.1590/s0001-37652002000100012.

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After 40 years of intensive research, chemistry of marine natural products has become a mature field. Since 1995, there are signals of decreased interest in the search of new metabolites from traditional sources such as macroalgae and octocorals, and the number of annual reports on marine sponges stabilized. On the contrary, metabolites from microorganisms is a rapidly growing field, due, at least in part, to the suspicion that a number of metabolites obtained from algae and invertebrates may be produced by associated microorganisms. Studies are concerned with bacteria and fungi, isolated from seawater, sediments, algae, fish and mainly from marine invertebrates such as sponges, mollusks, tunicates, coelenterates and crustaceans. Although it is still to early to define tendencies, it may be stated that the metabolites from microorganisms are in most cases quite different from those produced by the invertebrate hosts. Nitrogenated metabolites predominate over acetate derivatives, and terpenes are uncommon. Among the latter, sesquiterpenes, diterpenes and carotenes have been isolated; among nitrogenated metabolites, amides, cyclic peptides and indole alkaloids predominate.
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27

Cedeño Ramos, Raúl, Haydelba D´Armas, María Amaro, and Rosa Martínez. "Secondary metabolites, letalithy and antimicrobial activity of six marine sponges from Mochima Bay, Sucre state, Venezuela." UNED Research Journal 7, no. 2 (December 15, 2015): 225–32. http://dx.doi.org/10.22458/urj.v7i2.1149.

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he specimens of the sponges Aplysina lacunosa, Aplysina fulva, Cliona varians, Cinachyrella kuekenthali, Amphimedon viridis and Aaptos pernucleata, were collected in Mochima Bay, Venezuela, in October 2009 with the purpose of identifying families of secondary metabolites and evaluating the antibacterial properties, antifungal and brine shrimp lethal study of the ethyl acetate soluble fractions of these sponges. The chemical evaluation showed the presence of alkaloids, sterols, triterpenes, methylene ketone and tannins. The ethyl acetate soluble fractions of A. pernucleata, A. fulva and A. lacunosa sponges were the only ones that showed antibacterial activity against Staphylococcus aureus, Listeria monocytogenes, and Escherichia coli; the soluble fraction of A. lacunosa showed the highest inhibition zones. The antifungal activity was not significant, except for A. pernucleata sponge wich showed mild activity against Candida albicans. The most prominent lethal activity in Artemia salina, were observed for C. kuekenthali, A. viridis and A. pernucleata sponges, with LC50 values of 4,10, 1,13 and < 0,01µg/mL respectively. These results allow profiling the sponges A. lacunosa, A. pernucleata and A. fulva as promising sources of antimicrobial compounds and the sponges C. kuekenthali, A. viridis and A. pernucleata as sources of antitumor compounds.
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28

Bickmeyer, Ulf, Christoph Drechsler, Matthias Köck, and Michael Assmann. "Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation." Toxicon 44, no. 1 (July 2004): 45–51. http://dx.doi.org/10.1016/j.toxicon.2004.04.001.

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29

Gunawardana, Geewananda P., Shigeo Kohmoto, and Neal S. Burres. "New cytotoxic acridine alkaloids from two deep water marine sponges of the family." Tetrahedron Letters 30, no. 33 (January 1989): 4359–62. http://dx.doi.org/10.1016/s0040-4039(00)99360-2.

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30

He, Qianqian, Shuang Miao, Na Ni, Yuqing Man, and Kaikai Gong. "A Review of the Secondary Metabolites From the Marine Sponges of the Genus Aaptos." Natural Product Communications 15, no. 9 (September 1, 2020): 1934578X2095143. http://dx.doi.org/10.1177/1934578x20951439.

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Marine sponges, which belong to the phylum Porifera (Metazoa), are considered the single best source of marine natural products. Among them, members of the genus Aaptos are attractive targets for marine natural product research owing to their abundant biogenetic ability to produce aaptamine derivatives. Apart from aaptamine alkaloids, there are also reports of other compounds from Aaptos sponges. This work reviews the secondary metabolites isolated from Aaptos species from 1982 to 2020, with 46 citations referring to 62 compounds (47 for aaptamines and 15 for others). The emphasis is placed on the structure of the organic molecules, relevant biological activities, chemical ecology aspects, and biosynthesis studies, which are described in the classifications of aaptamines and other compounds in the order of the published year.
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Kashman, Yoel, Amira Rudi, and Doron Pappo. "Recent heterocyclic compounds from marine invertebrates: Structure and synthesis." Pure and Applied Chemistry 79, no. 4 (January 1, 2007): 491–505. http://dx.doi.org/10.1351/pac200779040491.

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A large variety of unique heterocyclic natural marine products, without terrestrial counterparts, have been isolated from marine invertebrates, mainly sponges, ascidians, and soft corals. Many of these compounds display interesting biological activity. In this review, we report our recent studies on nitrogen-containing heterocyclic compounds ("alkaloids"), as well as some containing sulfur and oxygen, which have been isolated from Red Sea and Indo-Pacific organisms, and discuss progress on the synthesis of these natural products and structural analogs.
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32

Zhang, Wenhan, and Joseph M. Ready. "Total synthesis of the dictyodendrins as an arena to highlight emerging synthetic technologies." Natural Product Reports 34, no. 8 (2017): 1010–34. http://dx.doi.org/10.1039/c7np00018a.

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The dictyodendrins are a family of alkaloids isolated from marine sponges, Dictyodendrilla verongiformis and Ianthella sp., which possess a highly substituted pyrrolo[2,3-c]carbazole core at the phenol or quinone oxidation states. This review discusses the many diverse approaches used to synthesize these complex natural products.
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33

Mudianta, I. Wayan, Andrew M. White, Peter L. Katavic, Rahul R. Krishnaraj, Anne E. Winters, Ernesto Mollo, Karen L. Cheney, and Mary J. Garson. "Chemoecological studies on marine natural products: terpene chemistry from marine mollusks." Pure and Applied Chemistry 86, no. 6 (June 18, 2014): 995–1002. http://dx.doi.org/10.1515/pac-2013-1111.

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AbstractSome species of nudibranchs (Mollusca) protect themselves from predatory attacks by storing defensive terpene chemicals acquired from dietary sponges (Porifera) in specialized body parts called MDFs (mantle dermal formations), often advertising their unpalatability to potential predators by means of bright coloration patterns. Consequently, the survival of these trophic specialist species is closely related to the possibility of obtaining the defensive tools from sponges that live in their immediate vicinity; therefore, it is important to determine as precisely as possible the chemical composition of nudibranch extracts prior to any ecological studies addressing issues that involve their alimentary behavior and their defensive strategies, including the significance of their color patterns. Some of our recent studies on the chemical composition of terpene extracts from nudibranchs belonging to the genera Chromodoris and Hypselodoris are summarized. We also report the development of a method to assay extracts and purified metabolites for their feeding deterrent activity against co-occurring generalist predators. In a recent chemoecological study, showing that repugnant terpene chemicals are accumulated at extremely high concentrations in exposed parts of the nudibranchs’ bodies, the feeding deterrence assays were carried out on the generalist marine shrimp Palaemon elegans, very common in the Mediterranean. We have modified this assay for use with the Australian shrimp species P. serenus, and confirmed the ecological validity of the assay by analysis of extracts from species of sponges and mollusks that live in the same habitat as P. serenus. The deterrent properties of haliclonacyclamine alkaloids isolated from the sponge Haliclona sp. were demonstrated, with the alkaloid mixture demonstrating palatability deterrence at concentrations as low as 0.05 mg/mL, and complete deterrence at 0.75 mg/mL. In contrast, the diterpene thuridillin metabolites from the sacoglossan mollusk Thuridilla splendens did not deter feeding by P. serenus.
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34

Thoms, Carsten, Rainer Ebel, Ute Hentsche, and Peter Proksch. "Sequestration of Dietary Alkaloids by the Spongivorous Marine Mollusc Tylodina perversa." Zeitschrift für Naturforschung C 58, no. 5-6 (June 1, 2003): 426–32. http://dx.doi.org/10.1515/znc-2003-5-623.

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Abstract Specimens of the spongivorous Mediterranean opisthobranch Tylodina perversa that had been collected while feeding on Aplysina aerophoba were shown to sequester the brominated isoxazoline alkaloids of their prey. Alkaloids were stored in the hepatopancreas, mantle tissues, and egg masses in an organ-specific manner. Surprisingly, the known sponge alkaloid aerothionin which is found only in A. cavernicola but not in A. aerophoba was also among the metabolites identified in wild caught specimens of T. perversa as well as in opisthobranchs with a documented feeding history on A. aerophoba. Mollusc derived aerothionin is postulated to be derived from a previous feeding encounter with A. cavernicola as T. perversa was found to freely feed on both Aplysina sponges in aquarium bioassays. The possible ecological significance of alkaloid sequestration by T. perversa is still unknown.
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35

Anisimov, Mikhail M., Elena L. Chaikina, and Natalia K. Utkina. "Alkaloids from Marine Sponges as Stimulators of Initial Stages of Development of Agricultural Plants." Natural Product Communications 9, no. 4 (April 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900405.

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Damirone A (1), damirone B (2), makaluvamine G (3), debromohymenialdisine (4), and dibromoagelaspongin (5) were examined for their ability to stimulate growth of seedling roots of barley (Hordeum vulgare L.), buckwheat (Fagopyrum esculentum Moench), corn (Zea mays L.), soy {Glycine max (L.) Merr.}, and wheat (Triticum aestivum L.). It was shown that the stimulatory effects depend on the chemical structure of the alkaloids and on the plant species. Compounds 1, 3, and 4 are efficient for growth of seedling roots of barley, compounds 2-5, at different concentrations, stimulate growth of buckwheat roots, and compound 5 stimulates growth of wheat roots. These compounds can be recommended for field study as plant growth stimulators.
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36

Nicacio, Karen J., Laura P. Ióca, Adriana M. Fróes, Luciana Leomil, Luciana R. Appolinario, Christiane C. Thompson, Fabiano L. Thompson, et al. "Cultures of the Marine Bacterium Pseudovibrio denitrificans Ab134 Produce Bromotyrosine-Derived Alkaloids Previously Only Isolated from Marine Sponges." Journal of Natural Products 80, no. 2 (February 13, 2017): 235–40. http://dx.doi.org/10.1021/acs.jnatprod.6b00838.

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37

Timm, Christoph, Thorsten Mordhorst, and Matthias Köck. "Synthesis of 3-Alkyl Pyridinium Alkaloids from the Arctic Sponge Haliclona viscosa." Marine Drugs 8, no. 3 (March 5, 2010): 483–97. http://dx.doi.org/10.3390/md8030483.

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3-Alkyl pyridinium alkaloids (3-APAs) are common secondary metabolites in marine sponges of the order Haplosclerida. In recent years, our laboratory has isolated and synthesized several new members of this family such as haliclamines C–F, viscosamine, viscosaline and a cyclic monomer. All of them were isolated from the Arctic sponge Haliclona viscosa collected in Spitsbergen, Norway. In this article we report the syntheses of these secondary metabolites from Haliclona viscosa and related compounds and give a short overview of the bioactivity.
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38

Shady, Nourhan, Mostafa Fouad, Mohamed Salah Kamel, Tanja Schirmeister, and Usama Abdelmohsen. "Natural Product Repertoire of the Genus Amphimedon." Marine Drugs 17, no. 1 (December 30, 2018): 19. http://dx.doi.org/10.3390/md17010019.

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Marine sponges are a very attractive and rich source in the production of novel bioactive compounds. The sponges exhibit a wide range of pharmacological activities. The genus Amphimedon consists of various species, such as viridis, compressa, complanata, and terpenensis, along with a handful of undescribed species. The Amphimedon genus is a rich source of secondary metabolites containing diverse chemical classes, including alkaloids, ceramides, cerebrososides, and terpenes, with various valuable biological activities. This review covers the literature from January 1983 until January 2018 and provides a complete survey of all the compounds isolated from the genus Amphimedon and the associated microbiota, along with their corresponding biological activities, whenever applicable.
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39

El-Naggar, Mohamed, and Robert J. Capon. "Discorhabdins Revisited: Cytotoxic Alkaloids from Southern Australian Marine Sponges of the Genera Higginsia and Spongosorites." Journal of Natural Products 72, no. 7 (July 24, 2009): 1368. http://dx.doi.org/10.1021/np9003596.

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40

Vassas, A., G. Bourdy, J. Paillard, J. Lavayre, M. Païs, J. Quirion, and C. Debitus. "Naturally Occurring Somatostatin and Vasoactive Intestinal Peptide Inhibitors. Isolation of Alkaloids from Two Marine Sponges." Planta Medica 62, no. 01 (February 1996): 28–30. http://dx.doi.org/10.1055/s-2006-957790.

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41

Hodnik, Žiga, Tihomir Tomašić, Lucija Peterlin Mašič, Fiona Chan, Robert W. Kirby, David J. Madge, and Danijel Kikelj. "Novel state-dependent voltage-gated sodium channel modulators, based on marine alkaloids from Agelas sponges." European Journal of Medicinal Chemistry 70 (December 2013): 154–64. http://dx.doi.org/10.1016/j.ejmech.2013.07.034.

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42

Zhang, Bin, Ting Zhang, Jianzhou Xu, Jian Lu, Panpan Qiu, Tingting Wang, and Lijian Ding. "Marine Sponge-Associated Fungi as Potential Novel Bioactive Natural Product Sources for Drug Discovery: A Review." Mini-Reviews in Medicinal Chemistry 20, no. 19 (December 28, 2020): 1966–2010. http://dx.doi.org/10.2174/1389557520666200826123248.

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Marine sponge-associated fungi are promising sources of structurally interesting and bioactive secondary metabolites. Great plenty of natural products have been discovered from spongeassociated fungi in recent years. Here reviewed are 571 new compounds isolated from marine fungi associated with sponges in 2010-2018. These molecules comprised eight different structural classes, including alkaloids, polyketides, terpenoids, meroterpenoids, etc. Moreover, most of these compounds demonstrated profoundly biological activities, such as antimicrobial, antiviral, cytotoxic, etc. This review systematically summarized the structural diversity, biological function, and future potential of these novel bioactive natural products for drug discovery.
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43

Kong, Yew Rong, Kai Ching Tay, Yi Xiang Su, Choon Kwang Wong, Wen Nee Tan, and Kooi Yeong Khaw. "Potential of Naturally Derived Alkaloids as Multi-Targeted Therapeutic Agents for Neurodegenerative Diseases." Molecules 26, no. 3 (January 30, 2021): 728. http://dx.doi.org/10.3390/molecules26030728.

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Alkaloids are a class of secondary metabolites that can be derived from plants, fungi and marine sponges. They are widely known as a continuous source of medicine for the management of chronic disease including cancer, diabetes and neurodegenerative diseases. For example, galanthamine and huperzine A are alkaloid derivatives currently being used for the symptomatic management of neurodegenerative disease. The etiology of neurodegenerative diseases is polygenic and multifactorial including but not limited to inflammation, oxidative stress and protein aggregation. Therefore, natural-product-based alkaloids with polypharmacology modulation properties are potentially useful for further drug development or, to a lesser extent, as nutraceuticals to manage neurodegeneration. This review aims to discuss and summarise recent developments in relation to naturally derived alkaloids for neurodegenerative diseases.
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44

Ebada, Sherif S., Mai Hoang Linh, Arlette Longeon, Nicole J. de Voogd, Emilie Durieu, Laurent Meijer, Marie-Lise Bourguet-Kondracki, Abdel Nasser B. Singab, Werner E. G. Müller, and Peter Proksch. "Dispacamide E and other bioactive bromopyrrole alkaloids from two Indonesian marine sponges of the genus Stylissa." Natural Product Research 29, no. 3 (August 12, 2014): 231–38. http://dx.doi.org/10.1080/14786419.2014.947496.

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45

Tsukamoto, Sachiko, Motohiko Takahashi, Shigeki Matsunaga, Nobuhiro Fusetani, and Rob W. M. van Soest. "Hachijodines A−G: Seven New Cytotoxic 3-Alkylpyridine Alkaloids from Two Marine Sponges of the GeneraXestospongiaandAmphimedon1." Journal of Natural Products 63, no. 5 (May 2000): 682–84. http://dx.doi.org/10.1021/np9905766.

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46

Khushi, Shamsunnahar, Laizuman Nahar, Angela A. Salim, and Robert J. Capon. "Trachycladindoles H–M: Molecular Networking Guided Exploration of a Library of Southern Australian Marine Sponges." Australian Journal of Chemistry 73, no. 4 (2020): 338. http://dx.doi.org/10.1071/ch19567.

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A global natural product social (GNPS) molecular network guided search of a library of 960 southern Australian marine sponge extracts successfully detected a deep-water Great Australian Bight sponge, Geodia sp. (CMB-01063), as a new source of a rare class of indolo-imidazole alkaloids previously believed to be unique to a single specimen of Trachycladus laevispirulifer (CMB-03397). Chemical analysis of CMB-01063 detected the known trachycladindoles A–G (1–7), and led to the isolation, characterisation, and structure elucidation of the new trachycladindoles H–M (8–13). Structures for 8–13 were assigned on the basis of detailed spectroscopic analysis, with comparison to authentic standards of 1–7.
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47

Sandjo, Louis P., Victor Kuete, and Maique W. Biavatti. "Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity." Beilstein Journal of Organic Chemistry 11 (September 18, 2015): 1667–99. http://dx.doi.org/10.3762/bjoc.11.183.

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This review focuses on pyridoacridine-related metabolites as one biologically interesting group of alkaloids identified from marine sources. They are produced by marine sponges, ascidians and tunicates, and they are structurally comprised of four to eight fused rings including heterocycles. Acridine, acridone, dihydroacridine, and quinolone cores are features regularly found in these alkaloid skeletons. The lack of hydrogen atoms next to quaternary carbon atoms for two or three rings makes the chemical shift assignment a difficult task. In this regard, one of the aims of this review is the compilation of previously reported, pyridoacridine 13C NMR data. Observations have been made on the delocalization of electrons and the presence of some functional groups that lead to changes in the chemical shift of some carbon resonances. The lack of mass spectra information for these alkaloids due to the compactness of their structures is further discussed. Moreover, the biosynthetic pathways of some of these metabolites have been shown since they could inspire biomimetic synthesis. The synthesis routes used to prepare members of these marine alkaloids (as well as their analogues), which are synthesized for biological purposes are also discussed. Pyridoacridines were found to have a large spectrum of bioactivity and this review highlights and compares the pharmacophores that are responsible for the observed bioactivity.
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48

Lichota, Anna, and Krzysztof Gwozdzinski. "Anticancer Activity of Natural Compounds from Plant and Marine Environment." International Journal of Molecular Sciences 19, no. 11 (November 9, 2018): 3533. http://dx.doi.org/10.3390/ijms19113533.

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This paper describes the substances of plant and marine origin that have anticancer properties. The chemical structure of the molecules of these substances, their properties, mechanisms of action, their structure–activity relationships, along with their anticancer properties and their potential as chemotherapeutic drugs are discussed in this paper. This paper presents natural substances from plants, animals, and their aquatic environments. These substances include the vinca alkaloids, mistletoe plant extracts, podophyllotoxin derivatives, taxanes, camptothecin, combretastatin, and others including geniposide, colchicine, artesunate, homoharringtonine, salvicine, ellipticine, roscovitine, maytanasin, tapsigargin, and bruceantin. Compounds (psammaplin, didemnin, dolastin, ecteinascidin, and halichondrin) isolated from the marine plants and animals such as microalgae, cyanobacteria, heterotrophic bacteria, invertebrates (e.g., sponges, tunicates, and soft corals) as well as certain other substances that have been tested on cells and experimental animals and used in human chemotherapy.
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49

Jaspars, Marcel, Topul Rali, Maureen Laney, Randall C. Schatzman, Maria Cristina Diaz, Francis J. Schmitz, Evamarie O. Pordesimo, and Phillip Crews. "The search for inosine 5′-Phosphate dehydrogenase (IMPDH) inhibitors from marine sponges. Evaluation of the bastadin alkaloids." Tetrahedron 50, no. 25 (1994): 7367–74. http://dx.doi.org/10.1016/s0040-4020(01)90467-3.

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50

Segraves, Nathaniel L., Suzette Lopez, Tyler A. Johnson, Sadri A. Said, Xiong Fu, Francis J. Schmitz, Halina Pietraszkiewicz, Frederick A. Valeriote, and Phillip Crews. "Structures and cytotoxicities of fascaplysin and related alkaloids from two marine phyla—Fascaplysinopsis sponges and Didemnum tunicates." Tetrahedron Letters 44, no. 17 (April 2003): 3471–75. http://dx.doi.org/10.1016/s0040-4039(03)00671-3.

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