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Journal articles on the topic 'Sponge alkaloids'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

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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2

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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3

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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4

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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5

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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6

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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7

Wu, Qihao, Song-Wei Li, Nicole J. de Voogd, Hong Wang, Li-Gong Yao, Yue-Wei Guo, and Xu-Wen Li. "Marine alkaloids as the chemical marker for the prey–predator relationship of the sponge Xestospongia sp. and the nudibranch Jorunna funebris." Marine Life Science & Technology 3, no. 3 (March 29, 2021): 375–81. http://dx.doi.org/10.1007/s42995-021-00096-w.

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AbstractThe dietary relationship study between marine sponge Xestospongia sp. and its nudibranch predators Jorunna funebris based on the discovery of isoquinolinequinones has long been studied. In this study, chemical investigation of the sponge Xestospongia sp. and nudibranch J. funebris from the South China Sea yielded a new marine alkaloid neopetroside C (1), together with nine known alkaloids (2–10). The chemical structures of all the compounds were elucidated by extensive spectroscopic analysis. Neopetroside C (1) featured a riboside of nicotinic acid with a rare α-N glycosildic linkage and an acyl residue of (Z)-2-methylbut-2-enoic acid attached to C-5′. The plausible chemical ecology relationship between sponge Xestospongia sp. and its nudibranch predator J. funebris was proposed based on the biogenetic relationship of the common marine alkaloids. The observation of two structural fragments, (Z)-2-methylbut-2-enoyloxy and trigonelline groups in both sponge and nudibranch, indicated that nudibranch might uptake chemicals from sponge and then modify and transform them into chemical weapons to defend against predators.

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8

Putz, Annika, Anne Kloeppel, Martin Pfannkuchen, Franz Brümmer, and Peter Proksch. "Depth-Related Alkaloid Variation in Mediterranean Aplysina Sponges." Zeitschrift für Naturforschung C 64, no. 3-4 (April 1, 2009): 279–87. http://dx.doi.org/10.1515/znc-2009-3-421.

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Total amounts and patterns of bromoisoxazoline alkaloids of Aplysina sponges from Croatia (Mediterranean Sea) were analyzed along an underwater slope ranging from 1.8 to 38.5 m. Total amounts of alkaloids varied from sample to sample and showed no correlation with depth. In contrast, striking differences of alkaloid patterns were found between sponges from shallow sites (1.8 - 11.8 m) and those collected from deeper sites (11.8 - 38.5 m). Sponges from shallow depths consistently exhibited alkaloid patterns typical for Aplysina aerophoba with aerophobin-2 (2) and isofistularin-3 (3) as main constituents. Sponges from deeper sites (below 11.8 m) resembled Aplysina cavernicola with aerothionin (4) and aplysinamisin- 1 (1) as major compounds. The typical A. cavernicola pigment 3,4-dihydroxyquinoline- 2-carboxylic acid (6), however, could not be detected in A. aerophoba sponges but was replaced by the A. aerophoba pigment uranidine (5) which appeared to be present in all sponge samples analyzed. During transplantation experiments sponges from sites below 30 m featuring the A. cavernicola chemotype of bromoisoxazoline alkaloids were translocated to shallower habitats (10 m). The alkaloid patterns in transplanted sponges were found to be stable over a period of 12 months and unaffected by this change in depth. In a further experiment, clones of Aplysina sponges from shallow depths of 5 - 6 m resembling the A. aerophoba chemotype were either kept in situ under natural light conditions or artificially shaded by excluding photosynthetically active radiation (PAR). Neither 4 nor 1 were detected in artificially shaded sponges over an observation period of 12 months. In summary, two chemically distinct types of Aplysina sponges were discovered in this study that proved to be remarkably stable with regard to the bromoisoxazoline patterns and unaffected either by changing the light conditions or depth. It is not clear presently whether the Aplysina sponges collected from depths < 11.8 m represent a new chemotype of A. cavernicola lacking the pigment 6 or whether we have incidentally come across a so far undescribed species of the genus Aplysina.

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9

Park, Seung-Il, Yeon-Ju Lee, Hoshik Won, Ki-Bong Oh, and Hyi-Seung Lee. "Indole Alkaloids from Tropical Sponge Hyrtios sp. as Isocitrate Lyase Inhibitors." Natural Product Communications 13, no. 6 (June 2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300608.

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A new β-carboline alkaloid, 3,4-dihydrohyrtiosulawesine (8), and fifteen known alkaloids were isolated from the tropical marine sponge Hyrtios sp. Among these known compounds, β-ketoserotonin (10) has been isolated for the first time from a natural source. The structures of the isolated compounds were determined by spectroscopic analyses and comparison with literature values. Compound 8 displayed potent inhibitory activities against isocitrate lyase (IC50: 92.9 μM) from Candida albicans.

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10

Kurimoto, Shin-ichiro, Taito Ohno, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Satoshi Ōmura, Jun’ichi Kobayashi, and Takaaki Kubota. "Ceratinadins E and F, New Bromotyrosine Alkaloids from an Okinawan Marine Sponge Pseudoceratina sp." Marine Drugs 16, no. 12 (November 23, 2018): 463. http://dx.doi.org/10.3390/md16120463.

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Two new bromotyrosine alkaloids, ceratinadins E (1) and F (2), were isolated from an Okinawan marine sponge Pseudoceratina sp. as well as a known bromotyrosine alkaloid, psammaplysin F (3). The gross structures of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by comparison of the NMR and ECD data with those of a known related bromotyrosine alkaloid, psammaplysin A (4). Ceratinadins E (1) and F (2) are new bromotyrosine alkaloids possessing an 8,10-dibromo-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol unit with two or three 11-N-methylmoloka’iamine units connected by carbonyl groups, respectively. Ceratinadin E (1) exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum (K1 and FCR3 strains, respectively).

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11

Akee, Rhone K., Tony R. Carroll, Wesley Y. Yoshida, Paul J. Scheuer, Thomas J. Stout, and Jon Clardy. "Two imidazole alkaloids from a sponge." Journal of Organic Chemistry 55, no. 6 (March 1990): 1944–46. http://dx.doi.org/10.1021/jo00293a048.

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12

Zhou, Yaming, Abdessamad Debbab, Attila Mándi, Victor Wray, Barbara Schulz, Werner E. G. Müller, Matthias Kassack, et al. "Alkaloids from the Sponge-Associated FungusAspergillussp." European Journal of Organic Chemistry 2013, no. 5 (December 11, 2012): 894–906. http://dx.doi.org/10.1002/ejoc.201201220.

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13

Inman, Wayne D., Mark O'Neill-Johnson, and Phillip Crews. "Novel marine sponge alkaloids. 1. Plakinidine A and B, anthelmintic active alkaloids from a Plakortis sponge." Journal of the American Chemical Society 112, no. 1 (January 1990): 1–4. http://dx.doi.org/10.1021/ja00157a001.

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14

Damayanti, Aspina, Asriani Ilyas, and Firnanelty Firnanelty. "Isolasi Senyawa Metabolit Sekunder Ekstrak Etanol Spons Stylotella sp Asal Kepulauan Selayar." ALCHEMY 8, no. 2 (October 31, 2020): 12–15. http://dx.doi.org/10.18860/al.v8i2.10213.

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Isolation of secondary metabolite compound has been conducted from sponge Stylotella sp., Selayar Island. Stylotella sp., one of Demospongiae class sponge, is found spreading in Selayar Island. This study aims to determine secondary metabolite compounds contained in the ethanol extract of Stylotella sp. sponge by extraction, fractionation and purification methods. The purity test was carried out by three eluent systems of TLC, namely chloroform:ethyl acetate (9:1), n-hexane:acetone (9:1), and chloroform:acetone (9:1). Each eluent produced a single spot. FTIR analysis of Stylotella sp. isolate showed that the pure isolates contained alkaloid compounds with the appearance of a typical functional group of alkaloid compounds. Keywords: Alkaloids, sponge Stylotella sp, extraction Telah dilakukan isolasi senyawa metabolit sekunder dari spons Stylotella sp. asal Kepulauan Selayar. Spons Stylotella sp merupakan spons kelas Demospongiae yang ditemukan penyebarannya di Perairan Pulau Selayar. Penelitian ini bertujuan untuk mengetahui golongan senyawa metabolit sekunder yang terdapat pada ekstrak etanol spons Stylotella sp. dengan metode ekstraksi, fraksinasi dan pemurnian. Uji kemurnian dilakukan dengan uji tiga sistem eluen pada KLT yaitu kloroform:etil asetat (9:1), n-heksan:aseton (9:1), dan kloroform:aseton (9:1). Masing-masing eluen menghasilkan noda tunggal. Isolat hasil analisis FTIR menunjukkan bahwa isolat murni mengandung senyawa alkaloid dengan munculnya gugus fungsi khas senyawa golongan alkaloid. Kata kunci: Alkaloid, spons Stylotella sp., ekstraksi

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15

An, Liang, Wenjuan Song, Xuli Tang, Nicole J. de Voogd, Qi wang, Meijun Chu, Pinglin Li, and Guoqiang Li. "Alkaloids and polyketides from the South China Sea sponge Agelas aff. nemoechinata." RSC Advances 7, no. 24 (2017): 14323–29. http://dx.doi.org/10.1039/c6ra27026c.

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16

Pech-Puch, Dawrin, Mar Pérez-Povedano, Marta Martinez-Guitian, Cristina Lasarte-Monterrubio, Juan Carlos Vázquez-Ucha, Germán Bou, Jaime Rodríguez, Alejandro Beceiro, and Carlos Jimenez. "In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa." Marine Drugs 18, no. 6 (June 23, 2020): 326. http://dx.doi.org/10.3390/md18060326.

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The pyrrole-imidazoles, a group of alkaloids commonly found in marine sponges belonging to the genus Agelas, display a wide range of biological activities. Herein, we report the first chemical study of the secondary metabolites of the sponge A. dilatata from the coastal area of the Yucatan Peninsula (Mexico). In this study, we isolated eight known alkaloids from an organic extract of the sponge. We used NMR and MS analysis and comparison with existing databases to characterize the alkaloids: ageliferin (1), bromoageliferin (2), dibromoageliferin (3), sceptrin (4), nakamuric acid (5), 4-bromo-1H-pyrrole-2-carboxylic acid (6), 4,5-dibromopyrrole-2-carboxylic acid (7) and 3,7-dimethylisoguanine (8). We also evaluated, for the first time, the activity of these alkaloids against the most problematic multidrug-resistant (MDR) pathogens, i.e., the Gram-negative bacteria Pseudomonas aeruginosa, Klebsiella pneumoniae and Acinetobacter baumannii. Bromoageliferin (2) displayed significant activity against P. aeruginosa. Comparison of the antibacterial activity of ageliferins 1–3 (of similar structure) against P. aeruginosa revealed some relationship between structure and activity. Furthermore, in in vitro assays, 2 inhibited growth and biofilm production in clinical strains of P. aeruginosa. Moreover, 2 increased the survival time in an in vivo Galleria mellonella model of infection. The findings confirm bromoageliferin (2) as a potential lead for designing new antibacterial drugs.

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17

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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18

Kwon, Oh-Seok, Donghwa Kim, Heegyu Kim, Yeon-Ju Lee, Hyi-Seung Lee, Chung Sim, Dong-Chan Oh, Sang Lee, Ki-Bong Oh, and Jongheon Shin. "Bromopyrrole Alkaloids from the Sponge Agelas kosrae." Marine Drugs 16, no. 12 (December 17, 2018): 513. http://dx.doi.org/10.3390/md16120513.

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Two new sceptrin derivatives (1,2) and eight structurally-related known bromopyrrole-bearing alkaloids were isolated from the tropical sponge Agelas kosrae. By a combination of spectroscopic methods, the new compounds, designated dioxysceptrin (1) and ageleste C (2), were determined to be structural analogs of each other that differ at the imidazole moiety. Dioxysceptrin was also found to exist as a mixture of α-amido epimers. The sceptrin alkaloids exhibited weak cytotoxicity against cancer cells. Compounds 1 and 2 also moderately exhibited anti-angiogenic and isocitrate lyase-inhibitory activities, respectively.

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19

Carroll, AR, BF Bowden, and JC Coll. "New Imidazole Alkaloids From the Sponge Leucetta sp. and the Associated Predatory Nudibranch Notodoris gardineri." Australian Journal of Chemistry 46, no. 8 (1993): 1229. http://dx.doi.org/10.1071/ch9931229.

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Three new imidazole alkaloids, naamidines Eand F and clathridine C, have been isolated from a sponge Leucetta sp., together with the known imidazole alkaloids naamidine A, pyronaamidine, clathridine and kealiiquinone. The predatory nudibranch Notodoris gardineri, which was found feeding on the sponge, contained the known metabolite clathridine. The structures of all compounds were delineated on the basis of one-dimensional and two-dimensional n.m.r. experiments at 300 MHz.

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20

Bartik, Kristin, Jean-Claude Braekman, Désiré Daloze, Catherine Stoller, Joëlle Huysecom, Gysèle Vandevyver, and Robert Ottinger. "Topsentins, new toxic bis-indole alkaloids from the marine sponge Topsentiagenitrix." Canadian Journal of Chemistry 65, no. 9 (September 1, 1987): 2118–21. http://dx.doi.org/10.1139/v87-352.

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Three new bis-indole alkaloids, topsentin-A (1), -B1 (2), and -B2 (3) have been isolated from the Mediterranean sponge Topsentiagenitrix and their structure determined by spectroscopic methods. These compounds are weakly toxic for fish and for dissociated cells of the freshwater sponge Ephydatiafluviatilis and thus might be partially responsible for the chemical defense of the sponge.

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21

Olatunji, Opeyemi, and Anuchit Plubrukarn. "Bromotyrosine-Derived Alkaloids from the Sponge SP." Open Conference Proceedings Journal 4, no. 1 (March 1, 2013): 263. http://dx.doi.org/10.2174/2210289201304010263.

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22

Kim, Chang-Kwon, Riswanto Riswanto, Tae Hyung Won, Heegyu Kim, Berna Elya, Chung J. Sim, Dong-Chan Oh, Ki-Bong Oh, and Jongheon Shin. "Manzamine Alkaloids from an Acanthostrongylophora sp. Sponge." Journal of Natural Products 80, no. 5 (April 28, 2017): 1575–83. http://dx.doi.org/10.1021/acs.jnatprod.7b00121.

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23

Perry, Nigel B., Laurent Ettouati, Marc Litaudon, John W. Blunt, Murray H. G. Munro, Sean Parkin, and Hakon Hope. "Alkaloids from the antarctic sponge Kirkpatrickia varialosa." Tetrahedron 50, no. 13 (March 1994): 3987–92. http://dx.doi.org/10.1016/s0040-4020(01)89673-3.

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24

Miyake, Fumiko Y., Kenichi Yakushijin, and David A. Horne. "Synthesis of Marine Sponge Bisindole Alkaloids Dihydrohamacanthins." Organic Letters 4, no. 6 (March 2002): 941–43. http://dx.doi.org/10.1021/ol020002j.

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25

Guinchard, Xavier, Yannick Vallée, and Jean-Noël Denis. "Total Syntheses of Brominated Marine Sponge Alkaloids." Organic Letters 9, no. 19 (September 2007): 3761–64. http://dx.doi.org/10.1021/ol701626m.

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26

Liu, Yonghong, Jee H. Jung, and Si Zhang. "Indole alkaloids from a sponge Sarcotragus species." Biochemical Systematics and Ecology 34, no. 5 (May 2006): 453–56. http://dx.doi.org/10.1016/j.bse.2005.11.010.

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27

Li, Peifer, Janussen, and Tasdemir. "New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis." Marine Drugs 17, no. 8 (July 25, 2019): 439. http://dx.doi.org/10.3390/md17080439.

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The sponge genus Latrunculia is a prolific source of discorhabdin type pyrroloiminoquinone alkaloids. In the continuation of our research interest into this genus, we studied the Antarctic deep-sea sponge Latrunculia biformis that showed potent in vitro anticancer activity. A targeted isolation process guided by bioactivity and molecular networking-based metabolomics yielded three known discorhabdins, (−)-discorhabdin L (1), (+)-discorhabdin A (2), (+)-discorhabdin Q (3), and three new discorhabdin analogs (−)-2-bromo-discorhabdin D (4), (−)-1-acetyl-discorhabdin L (5), and (+)-1-octacosatrienoyl-discorhabdin L (6) from the MeOH-soluble portion of the organic extract. The chemical structures of 1–6 were elucidated by extensive NMR, HR-ESIMS, FT-IR, [α]D, and ECD (Electronic Circular Dichroism) spectroscopy analyses. Compounds 1, 5, and 6 showed promising anticancer activity with IC50 values of 0.94, 2.71, and 34.0 µM, respectively. Compounds 1–6 and the enantiomer of 1 ((+)-discorhabdin L, 1e) were docked to the active sites of two anticancer targets, topoisomerase I-II and indoleamine 2,3-dioxygenase (IDO1), to reveal, for the first time, the binding potential of discorhabdins to these proteins. Compounds 5 and 6 are the first discorhabdin analogs with an ester function at C-1 and 6 is the first discorhabdin bearing a long-chain fatty acid at this position. This study confirms Latrunculia sponges to be excellent sources of chemically diverse discorhabdin alkaloids.

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Prasad, Pritesh, Angela A. Salim, Shamsunnahar Khushi, Zeinab G. Khalil, Michelle Quezada, and Robert J. Capon. "Solvolysis Artifacts: Leucettazoles as Cryptic Macrocyclic Alkaloid Dimers from a Southern Australian Marine Sponge, Leucetta sp." Marine Drugs 17, no. 2 (February 9, 2019): 106. http://dx.doi.org/10.3390/md17020106.

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29

Li, Fengjie, Dorte Janussen, Christian Peifer, Ignacio Pérez-Victoria, and Deniz Tasdemir. "Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity." Marine Drugs 16, no. 8 (August 2, 2018): 268. http://dx.doi.org/10.3390/md16080268.

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The Antarctic deep-sea sponge Latrunculia (Latrunculia) biformis Kirkpatrick, 1908 (Class Demospongiae Sollas, Order Poecilosclerida Topsent, Latrunculiidae Topsent) was selected for chemical analyses due to its potent anticancer activity. Metabolomic analysis of its crude extract by HRMS/MS-based molecular networking showed the presence of several clusters of pyrroloiminoquinone alkaloids, i.e., discorhabdin and epinardin-type brominated pyridopyrroloquinolines and tsitsikammamines, the non-brominated bis-pyrroloiminoquinones. Molecular networking approach combined with a bioactivity-guided isolation led to the targeted isolation of the known pyrroloiminoquinone tsitsikammamine A (1) and its new analog 16,17-dehydrotsitsikammamine A (2). The chemical structures of the compounds 1 and 2 were elucidated by spectroscopic analysis (one-dimensional (1D) and two-dimensional (2D) NMR, HR-ESIMS). Due to minute amounts, molecular modeling and docking was used to assess potential affinities to potential targets of the isolated compounds, including DNA intercalation, topoisomerase I-II, and indoleamine 2,3-dioxygenase enzymes. Tsitsikammamines represent a small class of pyrroloiminoquinone alkaloids that have only previously been reported from the South African sponge genus Tsitsikamma Samaai & Kelly and an Australian species of the sponge genus Zyzzya de Laubenfels. This is the first report of tsitsikammamines from the genus Latrunculia du Bocage and the successful application of molecular networking in the identification of comprehensive chemical inventory of L. biformis followed by targeted isolation of new molecules. This study highlights the high productivity of secondary metabolites of Latrunculia sponges and may shed new light on their biosynthetic origin and chemotaxonomy.

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Kobayashi, Jun'ichi. "Chemistry and biology of Okinawan marine natural products." Pure and Applied Chemistry 81, no. 6 (May 5, 2009): 1009–18. http://dx.doi.org/10.1351/pac-con-08-08-22.

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Marine macro- and micro-organisms collected in Okinawa are good sources of compounds with intriguing structures and interesting biological activities. Synthetic hybrid molecules of caffeine and eudistomin D from tunicates Eudistoma sp. were found to show better potency as adenosine receptor ligands than caffeine, and one of them exhibits potent activity for adenosine receptors tested, especially for A3 subtype. Potent cytotoxic polyene macrolides from a tunicate Cystodytes sp. were found to be potent osteoclast inhibitors and to inhibit vacuolar type H+-ATPase (V-ATPase) of both mammalian and yeast cells. Amphidinolactones A and B are new macrolides from a dinoflagellate Amphidinium sp., and a potent cytotoxic macrolide from another strain was found to target actin cytoskeleton. Theonezolide A, a long-chain polyketide from a sponge Theonella sp., induces a drastic shape change in platelets by reorganization of microtubules. The stereochemistry of many chiral centers in theonezolide A was elucidated by spectral data and chemical means. Metachromins L-Q are new sesquiterpenoid quinones with an amino acid residue, while nakijiquinones E and F were the first dimeric sesquiterpenoid quinones possessing a 3-aminobenzoate moiety. Halichonadin E is the first hetero-dimeric sesquiterpenoid with eudesmane and aromadendrane skeletons linked through a urea fragment isolated from a sponge Halichondria sp. Pyrinadine A and nakinadine A are novel bis-pyridine alkaloids from sponges, while nagelamides are new bromopyrrole alkaloids from a sponge Agelas sp. Here, the structures and bioactivities of these interesting marine natural products will be described.

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Rompis, Abrianto A. O., Fitje Losung, Deiske A. Sumilat, Agung B. Windarto, Stenly Wullur, and Laurentius T. X. Lalamentik. "The Antibacterial Activity Of Several Sponges From The Waters Of Tasik Ria Against Escherichia coli And Staphylococcus aureus bacteria." JURNAL ILMIAH PLATAX 7, no. 1 (October 29, 2018): 1. http://dx.doi.org/10.35800/jip.7.1.2019.21435.

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The sponge is one of the sea organisms that has a prospect as a source of natural compounds including peptides, steroids, asetogenin, terpenoids, alkaloids, cyclic halide and nitrogen. This research was directed to obtain several species of sponges from the waters of Tasik Ria as well as testing the antibacterial activity of extracts from some of the sponge against the bacteria Escherichia coli and Staphylococcus aureus. From the identification, seven species of sponges were found, which consists of: Amphimedon sp., Axinosa sp., Aaptos sp., Theonella sp., Cribochalina sp., Hyrtios sp., and Lendenfeldia sp. The tests of antibacterial activity of the extracts from these sponges against test bacteria E. coli and S. aureus showed some positive results. Extract from Axinosa sp. sponge(16 mm) showed the strongest antibacterial activity on Escherichia coli bacteria. Followed by Hyrtios sp. extract (13.5 mm), Aaptos sp. extract (13 mm), Lendenfeldia sp. extract (13 mm) and Cribochalinai sp. extract(10.5 mm). While the the tests on Staphylococcus aureus bacteria showed that the strongest antibacterial activity was found from Axinosa sp. sponge extract (16.5 mm), followed by the extract from Aaptos sp. (15 mm), Lendenfeldia sp. extract (14.5 mm), Hyrtios sp. extract(13.5 mm) and Cribochalina sp. extract (11 mm).Keywords: Sponge, antibacterial, Escherichia coli, Staphylococcus aureus ABSTRAK Spons merupakan salah satu biota laut yang sangat prospektif sebagai sumber senyawa bahan-bahan alami antara lain peptide, terpenoid, steroid, asetogenin, alkaloid, halide siklik dan senyawa nitrogen. Penelitian ini diarahkan untuk mendapatkan beberapa spesies spons dari perairan Tasik Ria serta menguji aktivitas antibakteri dari beberapa ekstrak spons terhadap bakteri Escherichia coli dan bakteri Staphylococcus aureus. Hasil identifikasi spons ditemukan sebanyak tujuh spesies yang terdiri dari: Amphimedon sp., Axinosa sp., Aaptos sp., Theonella sp., Hyrtios sp., Cribochalina sp. dan Lendenfeldia sp.. Aktivitas antibakteri dari beberapa ekstrak spons terhadap bakteri uji E. coli dan S. aureus terdapat diameter zona hambat bervariasi yaitu bakteri Escherichia coli menunjukkan aktivitas antibakteri ekstrak spons terkuat pada spons Axinosa sp (16 mm), disusul ekstrak spons Hyrtios sp. (13,5 mm), ekstrak spons Aaptos sp. (13 mm), ekstrak spons Lendenfeldia sp. (13 mm) dan ekstrak spons Cribochalinai sp. (10,5 mm). Sedangkan pada bakteri Staphylococcus aureus menunjukkan aktivitas antibakteri ekstrak spons terkuat yaitu: ekstrak spons Axinosa sp. (16,5 mm), disusul ekstrak spons Aaptos sp. (15 mm), ekstrak spons Lendenfeldia sp. (14,5 mm), ekstrak spons Hyrtios sp. (13,5 mm) dan ekstrak spons Cribochalina sp.(11mm).Kata Kunci : Spons, Antibakteri, Escherichia coli, Staphylococcus aureus

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Cychon, Christine, Ellen Lichte, and Matthias Köck. "The marine sponge Agelas citrina as a source of the new pyrrole–imidazole alkaloids citrinamines A–D and N-methylagelongine." Beilstein Journal of Organic Chemistry 11 (October 29, 2015): 2029–37. http://dx.doi.org/10.3762/bjoc.11.220.

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The chemical investigation of the Caribbean sponge Agelas citrina revealed four new pyrrole–imidazole alkaloids (PIAs), the citrinamines A–D (1–4) and the bromopyrrole alkaloid N-methylagelongine (5). All citrinamines are dimers of hymenidin (6) which was also isolated from this sponge as the major metabolite. Citrinamines A (1) and B (2) are derivatives of the PIA dimer mauritiamine (7), whereas citrinamine C (3) is derived from the PIA dimer nagelamide B (8). Citrinamine D (4) shows an uncommon linkage between the imidazole rings of both monomeric units as it is only observed in the benzocyclobutane ring moiety of benzosceptrins A–C (9–11). Compound 5 is the N-methyl derivative of agelongine (12) which consist of a pyridinium ring and an ester linkage instead of the aminoimidazole moiety and the common amide bond in PIAs.

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33

Hassan, Wafaa, RuAngelie Edrada, Rainer Ebel, Victor Wray, and Peter Proksch. "New Alkaloids from the Mediterranean Sponge Hamigera hamigera." Marine Drugs 2, no. 3 (August 25, 2004): 88–100. http://dx.doi.org/10.3390/md203088.

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34

Bao, Baoquan, Ping Zhang, Yoonmi Lee, Jongki Hong, Chong-O. Lee, and Jee Jung. "Monoindole Alkaloids from a Marine Sponge Spongosorites sp." Marine Drugs 5, no. 2 (June 25, 2007): 31–39. http://dx.doi.org/10.3390/md502031.

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35

Regalado, Erik L., Abilio Laguna, Judith Mendiola, Olivier P. Thomas, and Clara Nogueiras. "Bromopyrrole alkaloids from the caribbean sponge Agelas cerebrum." Química Nova 34, no. 2 (2011): 289–91. http://dx.doi.org/10.1590/s0100-40422011000200022.

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36

Ali, A., H. Hassanean, Ehab Elkhayat, Ru Edrada, Rainer Ebel, and Peter Proksch. "IMIDAZOLE ALKALOIDS FROM THE INDOPACIFIC SPONGE PERICHARAX HETERORAPHIS." Bulletin of Pharmaceutical Sciences. Assiut 30, no. 2 (December 1, 2007): 149–57. http://dx.doi.org/10.21608/bfsa.2007.64196.

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37

Hooper, Gregory J., Michael T. Davies-Coleman, Michelle Kelly-Borges, and Philip S. Coetzee. "New alkaloids from a South African latrunculid sponge." Tetrahedron Letters 37, no. 39 (September 1996): 7135–38. http://dx.doi.org/10.1016/0040-4039(96)01560-2.

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38

Takahashi, Yohei, Naonobu Tanaka, Takaaki Kubota, Haruaki Ishiyama, Azusa Shibazaki, Tohru Gonoi, Jane Fromont, and Jun’ichi Kobayashi. "Heteroaromatic alkaloids, nakijinamines, from a sponge Suberites sp." Tetrahedron 68, no. 41 (October 2012): 8545–50. http://dx.doi.org/10.1016/j.tet.2012.08.018.

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39

Jurek, Jaroslaw, Paul J. Scheuer, and Michelle Kelly-Borges. "Two Steroidal Alkaloids from a Sponge, Corticium Sp." Journal of Natural Products 57, no. 7 (July 1994): 1004–7. http://dx.doi.org/10.1021/np50109a022.

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40

Yang, Aimin, Bill J. Baker, Julia Grimwade, Alan Leonard, and James B. McClintock. "Discorhabdin Alkaloids from the Antarctic Sponge Latrunculia apicalis." Journal of Natural Products 58, no. 10 (October 1995): 1596–99. http://dx.doi.org/10.1021/np50124a020.

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41

Zuleta, Ignacio A., Marı́a Laura Vitelli, Ricardo Baggio, Marı́a Teresa Garland, Alicia M. Seldes, and Jorge A. Palermo. "Novel pteridine alkaloids from the sponge Clathria sp." Tetrahedron 58, no. 22 (May 2002): 4481–86. http://dx.doi.org/10.1016/s0040-4020(02)00392-7.

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42

Hassan, Wafaa H. B., Areej M. Al-Taweel, and Peter Proksch. "Two new imidazole alkaloids from Leucetta chagosensis sponge." Saudi Pharmaceutical Journal 17, no. 4 (October 2009): 295–98. http://dx.doi.org/10.1016/j.jsps.2009.10.006.

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43

Zhou, Bing-Nan, Carla Slebodnick, Randall K. Johnson, Michael R. Mattern, and David G. I. Kingston. "New Cytotoxic Manzamine Alkaloids from a Palaun Sponge." Tetrahedron 56, no. 32 (August 2000): 5781–84. http://dx.doi.org/10.1016/s0040-4020(00)00534-2.

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44

Ebada, Sherif Saeed, RuAngelie Edrada-Ebel, Nicole J. de Voogd, Victor Wray, and Peter Proksch. "Dibromopyrrole Alkaloids from the Marine Sponge Acanthostylotella sp." Natural Product Communications 4, no. 1 (January 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400112.

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Fourteen dibromopyrrole alkaloids were isolated from the marine sponge Acanthostylotella sp. collected in Indonesia. In addition to the known compounds 4,5-dibromo-N-(methoxy-methyl)-1 H-pyrrole-2-carboxamide (7), 4,5-dibromo-1 H-pyrrole-2-carboxamide (8), mukanadin D (9), (±)-longamide B methyl ester (10), (±)-longamide B (11), (±)-longamide (12), 3,4-dibromo-1 H-pyrrole-2-carboxamide (13), 2-cyano-4,5-dibromo-1 H-pyrrole (14), six compounds were isolated that proved to be new natural products including acanthamides A – D (1 – 4), methyl 3,4-dibromo-1 H-pyrrole-2-carboxylate (5) and 3,5-dibromo-1 H-pyrrole-2-carboxylic acid (6). The structures of the new compounds were unequivocally identified based on one and two dimensional NMR and on HRFTMS as well as by comparison with the literature.

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45

Shubina, Larisa K., Anatoly I. Kalinovsky, Sergey N. Fedorov, Oleg S. Radchenko, Vladimir A. Denisenko, Pavel S. Dmitrenok, Sergey A. Dyshlovoy, Vladimir B. Krasokhin, and Valentin A. Stonik. "Aaptamine Alkaloids from the Vietnamese Sponge Aaptos sp." Natural Product Communications 4, no. 8 (August 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400813.

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A series of aaptamines, including one new alkaloid (1), were isolated from the marine sponge Aaptos sp. collected in Vietnamese waters. The structure of 1 was elucidated using NMR and HRESIMS, as well as by chemical transformation of 1 to the previously known aaptamine and established as 3-N-morpholinyl-9-demethyl(oxy)aaptamine. The isolated compounds showed a potential cancer preventive activity.

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Kusama, Taishi, Naonobu Tanaka, Azusa Takahashi-Nakaguchi, Tohru Gonoi, Jane Fromont, and Jun’ichi Kobayashi. "Bromopyrrole Alkaloids from a Marine Sponge Agelas sp." Chemical and Pharmaceutical Bulletin 62, no. 5 (2014): 499–503. http://dx.doi.org/10.1248/cpb.c14-00077.

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Bobzin, Steven C., and D. John Faulkner. "Aromatic alkaloids from the marine sponge Chelonaplysilla sp." Journal of Organic Chemistry 56, no. 14 (July 1991): 4403–7. http://dx.doi.org/10.1021/jo00014a015.

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48

Fendert, Thomas, Victor Wray, Rob W. M. van Soest, and Peter Proksch. "Bromoisoxazoline Alkaloids from the Caribbean Sponge Aplysina insularis." Zeitschrift für Naturforschung C 54, no. 3-4 (April 1, 1999): 246–52. http://dx.doi.org/10.1515/znc-1999-3-415.

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Abstract An investigation of a specimen of the Caribbean sponge Aplysina insularis resulted in the isolation of fourteen bromoisoxazoline alkaloids (1 - 14), of which 14-oxo-aerophobin-2 (1)* is a novel derivative. Structure elucidation of the compounds have been established from spectral studies and data for 1 are reported. Constituents 2 to 6 and 11 to 14 have not been identified sofar in Aplysina insularis species. The presence of the known compounds 7 to 9 in Aplysina insularis indicates that their use for chemotaxonomical purposes is questionable.

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Wang, Ru-Ping, Hou-Wen Lin, Ling-Zhi Li, Pin-Yi Gao, Ying Xu, and Shao-Jiang Song. "Monoindole alkaloids from a marine sponge Mycale fibrexilis." Biochemical Systematics and Ecology 43 (August 2012): 210–13. http://dx.doi.org/10.1016/j.bse.2012.03.016.

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Hanif, Novriyandi, Kaoru Yamada, Makoto Kitamura, Yoshinori Kawazoe, Nicole J. de Voogd, and Daisuke Uemura. "New Indole Alkaloids from the Sponge Plakortis sp." Chemistry of Natural Compounds 51, no. 6 (November 2015): 1130–33. http://dx.doi.org/10.1007/s10600-015-1508-0.

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