Login Register Cart 0
Review Article

海绵中卤代成分的结构和生物活性研究

卷 27, 期 14, 2020

页: [2335 - 2360] 页: 26

弟呕挨: 10.2174/0929867325666181112092159

价格: $65

Open Access Journals Promotions 2
摘要

海洋生物是生物活性天然产物的丰富来源。 在海绵及其相关微生物群落产生的代谢产物中，卤化天然化合物由于其强大的生物活性而占重要地位。 本综述更新和汇总了过去三十年中分离出的258种卤代有机化合物，特别是来自31属海洋海绵的溴化衍生物。 这些化合物可分为以下几类：溴化多不饱和脂质，氮化合物，溴化酪氨酸衍生物和其他卤化化合物。 列出了这些物质及其来源生物，结构和生物活性。 为此，参考了84篇参考文献。

关键词: 卤化，海绵，海洋，分离物，构成，活性。

« Previous Next »
[1]
Woo, S.Y.; Win, N.N.; Wong, C.P.; Ito, T.; Hoshino, S.; Ngwe, H.; Aye, A.A.; Han, N.M.; Zhang, H.; Hayashi, F.; Abe, I.; Morita, H. Two new pyrrolo-2-aminoimidazoles from a Myanmarese marine sponge, Clathria prolifera. J. Nat. Med., 2018, 72(3), 803-807.
[http://dx.doi.org/10.1007/s11418-018-1205-y] [PMID: 29569222]
[2]
Öztürk, B.; de Jaeger, L.; Smidt, H.; Sipkema, D. Culture-dependent and independent approaches for identifying novel halogenases encoded by Crambe crambe (marine sponge) microbiota. Sci. Rep., 2013, 3(6153), 2780-2787.
[http://dx.doi.org/10.1038/srep02780] [PMID: 24071658]
[3]
Li, T.; Wang, B.; De Voogd, N.J.; Tang, X.L. Two new diterpene alkaloids from the South China sea sponge Agelas aff. Nemoechinata. Chin. Chem. Lett., 2016, 47(7), 1048-1051.
[http://dx.doi.org/10.1016/j.cclet.2016.05.017]
[4]
Carté, B.K. Biomedical potential of marine natural products. Bioscience, 1996, 46(4), 271-286.
[http://dx.doi.org/10.2307/1312834]
[5]
Gribble, G.W. Recently discovered naturally occurring heterrocyclic organohalogen compounds. Heterocycles, 2012, 84(1), 157-207.
[http://dx.doi.org/10.3987/REV-11-SR(P)5]
[6]
Gribble, G.W. The diversity of naturally produced organohalogens. Chemosphere, 2003, 52(2), 289-297.
[http://dx.doi.org/10.1016/S0045-6535(03)00207-8] [PMID: 12738253]
[7]
Vetter, W.; Janussen, D. Halogenated natural products in five species of Antarctic sponges: compounds with POP-like properties? Environ. Sci. Technol., 2005, 39(11), 3889-3895.
[http://dx.doi.org/10.1021/es0484597] [PMID: 15984761]
[8]
Laport, M.S.; Santos, O.C.; Muricy, G. Marine sponges: potential sources of new antimicrobial drugs. Curr. Pharm. Biotechnol., 2009, 10(1), 86-105.
[http://dx.doi.org/10.2174/138920109787048625] [PMID: 19149592]
[9]
Lira, N.S.; Montes, R.C.; Tavares, J.F.; da Silva, M.S.; da Cunha, E.V.; de Athayde-Filho, P.F.; Rodrigues, L.C.; da Silva Dias, C.; Barbosa-Filho, J.M. Brominated compounds from marine sponges of the genus Aplysina and a compilation of their 13C NMR spectral data. Mar. Drugs, 2011, 9(11), 2316-2368.
[http://dx.doi.org/10.3390/md9112316] [PMID: 22163189]
[10]
Laus, G. Biological activities of natural halogen compounds. Stud. Nat. Prod. Chem., 2001, 25, 757-809.
[http://dx.doi.org/10.1016/S1572-5995(01)80022-3]
[11]
Lebouvier, N.; Jullian, V.; Desvignes, I.; Maurel, S.; Parenty, A.; Dorin-Semblat, D.; Doerig, C.; Sauvain, M.; Laurent, D. Antiplasmodial activities of homogentisic acid derivative protein kinase inhibitors isolated from a Vanuatu marine sponge Pseudoceratina sp. Mar. Drugs, 2009, 7(4), 640-653.
[http://dx.doi.org/10.3390/md7040640] [PMID: 20098604]
[12]
Aiello, A.; Fattorusso, E.; Imperatore, C.; Menna, M.; Müller, W.E. Iodocionin, a cytotoxic iodinated metabolite from the Mediterranean ascidian Ciona edwardsii. Mar. Drugs, 2010, 8(2), 285-291.
[http://dx.doi.org/10.3390/md8020285] [PMID: 20390106]
[13]
Jiang, W.; Liu, D.; Deng, Z.W.; De Voogd, N.J.; Proksch, P.; Lin, W. Brominated polyunsaturated lipids and their stereochemistry from the Chinese marine sponge Xestospongia testudinaria. Tetrahedron, 2011, 67(1), 58-68.
[http://dx.doi.org/10.1016/j.tet.2010.11.045]
[14]
Pham, N.B.; Butler, M.S.; Hooper, J.N.A.; Moni, R.W.; Quinn, R.J. Isolation of xestosterol esters of brominated acetylenic fatty acids from the marine sponge xestospongia testudinaria. J. Nat. Prod., 1999, 62(10), 1439-1442.
[http://dx.doi.org/10.1021/np9901635] [PMID: 10543913]
[15]
Keffer, J.L.; Plaza, A.; Bewley, C.A. Motualevic acids A-F, antimicrobial acids from the sponge Siliquariaspongia sp. Org. Lett., 2009, 11(5), 1087-1090.
[http://dx.doi.org/10.1021/ol802890b] [PMID: 19191563]
[16]
Liang, L.F.; Wang, T.; Cai, Y.S.; He, W.F.; Sun, P.; Li, Y.F.; Huang, Q.; Taglialatela-Scafati, O.; Wang, H.Y.; Guo, Y.W. Brominated polyunsaturated lipids from the Chinese sponge Xestospongia testudinaria as a new class of pancreatic lipase inhibitors. Eur. J. Med. Chem., 2014, 79, 290-297.
[http://dx.doi.org/10.1016/j.ejmech.2014.04.003] [PMID: 24747066]
[17]
Akiyama, T.; Takada, K.; Oikawa, T.; Matsuura, N.; Ise, Y.; Okada, S.; Matsunaga, S. Stimulators of adipogenesis from the marine sponge Xestospongia testudinaria. Tetrahedron, 2013, 69(32), 6560-6564.
[http://dx.doi.org/10.1016/j.tet.2013.06.007]
[18]
Davis, R.A.; Duffy, S.; Avery, V.M.; Camp, D.; Hooper, J.N.A.; Quinn, R.J. (+)-7-Bromotrypargine: an antimalarial β-carboline from the Australian marine sponge Ancorina sp. Tetrahedron Lett., 2010, 51(4), 583-585.
[http://dx.doi.org/10.1016/j.tetlet.2009.11.055]
[19]
Dai, J.; Jiménez, J.I.; Kelly, M.; Williams, P.G. Dictazoles: potential vinyl cyclobutane biosynthetic precursors to the dictazolines. J. Org. Chem., 2010, 75(7), 2399-2402.
[http://dx.doi.org/10.1021/jo902566n] [PMID: 20222695]
[20]
Watts, K.R.; Morinaka, B.I.; Amagata, T.; Robinson, S.J.; Tenney, K.; Bray, W.M.; Gassner, N.C.; Lokey, R.S.; Media, J.; Valeriote, F.A.; Crews, P. Biostructural features of additional jasplakinolide (jaspamide) analogues. J. Nat. Prod., 2011, 74(3), 341-351.
[http://dx.doi.org/10.1021/np100721g] [PMID: 21241058]
[21]
Gala, F.; D’auria, M.V.; De Marino, S.; Sepe, V.; Zollo, F.; Smith, C.D.; Keller, S.N.; Zampella, A. Jaspamides M-P: new tryptophan modified jaspamide derivatives from the sponge Jaspis splendans. Tetrahedron, 2009, 65, 51-56.
[http://dx.doi.org/10.1016/j.tet.2008.10.076]
[22]
Plaza, A.; Keffer, J.L.; Lloyd, J.R.; Colin, P.L.; Bewley, C.A. Paltolides A--C, anabaenopeptin-type peptides from the palau sponge Theonella swinhoei. J. Nat. Prod., 2010, 73(3), 485-488.
[http://dx.doi.org/10.1021/np900728x] [PMID: 20078073]
[23]
Lu, Z.; Van Wagoner, R.M.; Harper, M.K.; Baker, H.L.; Hooper, J.N.; Bewley, C.A.; Ireland, C.M. Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa. J. Nat. Prod., 2011, 74(2), 185-193.
[http://dx.doi.org/10.1021/np100613p] [PMID: 21280591]
[24]
Buchanan, M.S.; Carroll, A.R.; Wessling, D.; Jobling, M.; Avery, V.M.; Davis, R.A.; Feng, Y.; Hooper, J.N.; Quinn, R.J. Clavatadines C-E, guanidine alkaloids from the Australian sponge Suberea clavata. J. Nat. Prod., 2009, 72(5), 973-975.
[http://dx.doi.org/10.1021/np8008013] [PMID: 19379003]
[25]
El-Naggar, M.; Capon, R.J. Discorhabdins revisited: cytotoxic alkaloids from southern australian marine sponges of the genera Higginsia and Spongosorites. J. Nat. Prod., 2009, 72(3), 460-464.
[http://dx.doi.org/10.1021/np8007667] [PMID: 19226152]
[26]
Grkovic, T.; Copp, B.R. New natural products in the discorhabdin A- and B-series from New Zealand-sourced Latrunculia spp. sponges. Tetrahedron, 2009, 65(32), 6335-6340.
[http://dx.doi.org/10.1016/j.tet.2009.06.012]
[27]
Na, M.; Ding, Y.; Wang, B.; Tekwani, B.L.; Schinazi, R.F.; Franzblau, S.; Kelly, M.; Stone, R.; Li, X.C.; Ferreira, D.; Hamann, M.T. Anti-infective discorhabdins from a deep-water alaskan sponge of the genus Latrunculia. J. Nat. Prod., 2010, 73(3), 383-387.
[http://dx.doi.org/10.1021/np900281r] [PMID: 20337497]
[28]
Hertiani, T.; Edrada-Ebel, R.; Ortlepp, S.; van Soest, R.W.; de Voogd, N.J.; Wray, V.; Hentschel, U.; Kozytska, S.; Müller, W.E.; Proksch, P. From anti-fouling to biofilm inhibition: new cytotoxic secondary metabolites from two Indonesian Agelas sponges. Bioorg. Med. Chem., 2010, 18(3), 1297-1311.
[http://dx.doi.org/10.1016/j.bmc.2009.12.028] [PMID: 20061160]
[29]
Appenzeller, J.; Tilvi, S.; Martin, M.T.; Gallard, J.F. EI-bitar, H.; Dau, E.T.; Debitus; Laurent, D.; Moriou, C.; AI-Mourabit, A. Benzosceptrins A (Ia) and B (Ib) with a unique benzocyclobutane skeleton and nagelamide S (II) and T (III) from pacific sponges. Org. Lett., 2010, 11(21), 4874-4877.
[http://dx.doi.org/10.1021/ol901946h] [PMID: 19863148]
[30]
Tilvi, S.; Moriou, C.; Martin, M.T.; Gallard, J.F.; Sorres, J.; Patel, K.; Petek, S.; Debitus, C.; Ermolenko, L.; Al-Mourabit, A. Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge Agelas dendromorpha. J. Nat. Prod., 2010, 73(4), 720-723.
[http://dx.doi.org/10.1021/np900539j] [PMID: 20166736]
[31]
D’ambrosio, M.; Guerriero, A.; Pietra, F.; Ripamonti, M.; Debitus, C.; Waikedre, J.; Pietra, F. The active centres of agelastatin A, a strongly cytotoxic alkaloid of the coral sea axinellid sponge Agelas dendromorpha, as determined by comparative bioassays with semisynthetic derivatives. Helv. Chim. Acta, 1996, 79(3), 727-735.
[http://dx.doi.org/10.1002/hlca.19960790315]
[32]
Hong, T.W.; Jímenez, D.R.; Molinski, T.F. Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A. J. Nat. Prod., 1998, 61(1), 158-161.
[http://dx.doi.org/10.1021/np9703813] [PMID: 9461668]
[33]
Yasuda, T.; Araki, A.; Kubota, T.; Ito, J.; Mikami, Y.; Fromont, J.; Kobayashi, J. Bromopyrrole alkaloids from marine sponges of the genus Agelas. J. Nat. Prod., 2009, 72(3), 488-491.
[http://dx.doi.org/10.1021/np800645q] [PMID: 19209898]
[34]
Patel, K.; Laville, R.; Martin, M.T.; Tilvi, S.; Moriou, C.; Gallard, J.F.; Ermolenko, L.; Debitus, C.; Al-Mourabit, A. Unprecedented stylissazoles A-C from Stylissa carteri: another dimension for marine pyrrole-2-aminoimidazole metabolite diversity. Angew. Chem. Int. Ed. Engl., 2010, 49(28), 4775-4779.
[http://dx.doi.org/10.1002/anie.201000444] [PMID: 20514657]
[35]
Sauleau, P.; Retailleau, P.; Nogues, S.; Carletti, I.; Marcourt, L.; Raux, R.; Mourabit, A.I.A.; Debitus, C.A.; Debitus, C. Dihydrohymenialdisines, new pyrrole-2-amino-imidazole alkaloids from the marine sponge Cymbastela cantharella. Tetrahedron Lett., 2011, 52, 2676-2678.
[http://dx.doi.org/10.1016/j.tetlet.2011.03.073]
[36]
Ebada, S.S.; Edrada-Ebel, R.; de Voogd, N.J.; Wray, V.; Proksch, P. Dibromopyrrole alkaloids from the marine sponge Acanthostylotella sp. Nat. Prod. Commun., 2009, 4(1), 47-52.
[http://dx.doi.org/10.1177/1934578X0900400112] [PMID: 19370874]
[37]
Hu, J.F.; Peng, J.; Kazi, A.B.; Kelly, M.; Hamann, M.T. Bromopyrrole alkaloids from the Jamaican sponge Didiscus oxeata. J. Chem. Res., 2005, 36(50), 427-428.
[http://dx.doi.org/10.3184/030823405774309113]
[38]
Umeyama, A.; Ito, S.; Yuasa, E.; Arihara, S.; Yamada, T. A new bromopyrrole alkaloid and the optical resolution of the racemate from the marine sponge homaxinella sp. J. Nat. Prod., 1998, 61(11), 1433-1434.
[http://dx.doi.org/10.1021/np980207u] [PMID: 9834174]
[39]
König, G.M.; Wright, A.D.; Linden, A.; Linden, A. Antiplasmodial and cytotoxic metabolites from the Maltese sponge Agelas oroides. Planta Med., 1998, 64(5), 443-447.
[http://dx.doi.org/10.1055/s-2006-957477] [PMID: 9690346]
[40]
Fattorusso, E.; Taglialatela-Scafati, O. Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides. Tetrahedron Lett., 2000, 41(50), 9917-9922.
[http://dx.doi.org/10.1016/S0040-4039(00)01764-0]
[41]
Parra, L.L.L.; Bertonha, A.F.; Severo, I.R.M.; Aguiar, A.C.C.; de Souza, G.E.; Oliva, G.; Guido, R.V.C.; Grazzia, N.; Costa, T.R.; Miguel, D.C.; Gadelha, F.R.; Ferreira, A.G.; Hajdu, E.; Romo, D.; Berlinck, R.G.S. Isolation, derivative synthesis, and structure-activity relationships of antiparasitic bromopyrrole alkaloids from the marine sponge Tedania brasiliensis. J. Nat. Prod., 2018, 81(1), 188-202.
[http://dx.doi.org/10.1021/acs.jnatprod.7b00876] [PMID: 29297684]
[42]
Dalisay, D.S.; Molinski, T.F. Structure elucidation at the nanomole scale. 3. Phorbasides G-I from Phorbas sp. J. Nat. Prod., 2010, 73(4), 679-682.
[http://dx.doi.org/10.1021/np1000297] [PMID: 20184337]
[43]
Xu, S.; Yoshimura, H.; Maru, N.; Ohno, O.; Arimoto, H.; Uemura, D. Pinnarine, another member of the halichlorine family. Isolation and preparation from pinnaic acid. J. Nat. Prod., 2011, 74(5), 1323-1326.
[http://dx.doi.org/10.1021/np200031d] [PMID: 21410164]
[44]
Esposito, G.; Bourguet-Kondracki, M.L.; Mai, L.H.; Longeon, A.; Teta, R.; Meijer, L.; Van Soest, R.; Mangoni, A.; Costantino, V. Chloromethylhalicyclamine B, a marine-derived protein kinase CK1δ/ε inhibitor. J. Nat. Prod., 2016, 79(11), 2953-2960.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00939] [PMID: 27933894]
[45]
Shaala, L.A.; Youssef, D.T.A.; Badr, J.M.; Sulaiman, M.; Khedr, A.E.I.; Sayed, K.A. Bioactive alkaloids from the Red Sea marine Verongid sponge Pseudoceratina arabica. Tetrahedron, 2015, 71(41), 7837-7841.
[http://dx.doi.org/10.1016/j.tet.2015.08.024]
[46]
Cruz, P.G.; Martínez Leal, J.F.; Daranas, A.H.; Pérez, M.; Cuevas, C. On the mechanism of action of dragmacidins I and J, two new representatives of a new class of protein phosphatase 1 and 2A inhibitors. ACS Omega, 2018, 3(4), 3760-3767.
[http://dx.doi.org/10.1021/acsomega.7b01786] [PMID: 30023878]
[47]
Campos, P.E.; Wolfender, J.L.; Queiroz, E.F.; Marcourt, L. AI-Mourabit, A.; De Voogd, N.; Illien, B.; Gauvin-Bialecki, A. Amphimedonoic acid and psammaplysene E, novel brominated alkaloids from Amphimedon sp. Tetrahedron Lett., 2017, 58(40), 3901-3904.
[http://dx.doi.org/10.1016/j.tetlet.2017.08.072]
[48]
Maru, N.; Koyama, T.; Ohno, O.; Kaoru, K.; Uemura, D. Sunabedine, a novel toxic bromotyrosine-derivative alkaloid from Okinawan sponge, order Verongida. Heterocycles, 2010, 82(1), 371-375.
[http://dx.doi.org/10.3987/COM-10-S(E)7]
[49]
Feng, Y.; Davis, R.; Sykes, M.; Avery, V.; Camp, D.; Quinn, R. Pseudoceratinazole A: a novel bromotyrosine alkaloid from the Australian sponge Pseudoceratina sp. Tetrahedron Lett., 2010, 51(37), 4847-4850.
[http://dx.doi.org/10.1016/j.tetlet.2010.07.052]
[50]
Yang, X.; Davis, R.A.; Buchanan, M.S.; Duffy, S.; Avery, V.M.; Camp, D.; Quinn, R.J. Antimalarial bromotyrosine derivatives from the Australian marine sponge Hyattella sp. J. Nat. Prod., 2010, 73(5), 985-987.
[http://dx.doi.org/10.1021/np900834g] [PMID: 20462236]
[51]
Xu, M.; Andrews, K.T.; Birrell, G.W.; Tran, T.L.; Camp, D.; Davis, R.A.; Quinn, R.J. Psammaplysin H, a new antimalarial bromotyrosine alkaloid from a marine sponge of the genus Pseudoceratina. Bioorg. Med. Chem. Lett., 2011, 21(2), 846-848.
[http://dx.doi.org/10.1016/j.bmcl.2010.11.081] [PMID: 21190857]
[52]
Kon, Y.; Kubota, T.; Shibazaki, A.; Gonoi, T.; Kobayashi, J. Ceratinadins A-C, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp. Bioorg. Med. Chem. Lett., 2010, 20(15), 4569-4572.
[http://dx.doi.org/10.1016/j.bmcl.2010.06.015] [PMID: 20584605]
[53]
Calcul, L.; Inman, W.D.; Morris, A.A.; Tenney, K.; Ratnam, J.; McKerrow, J.H.; Valeriote, F.A.; Crews, P. Additional insights on the bastadins: isolation of analogues from the sponge Ianthella cf. reticulata and exploration of the oxime configurations. J. Nat. Prod., 2010, 73(3), 365-372.
[http://dx.doi.org/10.1021/np9005986] [PMID: 20102170]
[54]
Fujiwara, T.; Hwang, J.H.; Kanamoto, A.; Nagai, H.; Takagi, M.; Shin-Ya, K. JBIR-44, a new bromotyrosine compound from a marine sponge Psammaplysilla purpurea. J. Antibiot. (Tokyo), 2009, 62(7), 393-395.
[http://dx.doi.org/10.1038/ja.2009.49] [PMID: 19557033]
[55]
Wright, A.E.; Roth, G.P.; Hoffman, J.K.; Divlianska, D.B.; Pechter, D.; Sennett, S.H.; Guzmán, E.A.; Linley, P.; McCarthy, P.J.; Pitts, T.P.; Pomponi, S.A.; Reed, J.K. Isolation, synthesis, and biological activity of aphrocallistin, an adenine-substituted bromotyramine metabolite from the Hexactinellida sponge Aphrocallistes beatrix. J. Nat. Prod., 2009, 72(6), 1178-1183.
[http://dx.doi.org/10.1021/np900183v] [PMID: 19459694]
[56]
Nakamura, H.; Wu, H.; Kobayashi, J.I.; Nakamura, Y.; Ohizumi, Y.; Hirat, Y. Purealin, a novel enzyme activator from the Okinawan marine sponge Psammaplysilla purea. Tetrahedron Lett., 1985, 26(37), 4517-4520.
[http://dx.doi.org/10.1016/S0040-4039(00)88945-5]
[57]
Takito, J.; Nakamura, H.; Kobayashi, J.; Ohizumi, Y.; Ebisawa, K.; Nonomura, Y. Purealin, a novel enzyme activator from the Okinawan marine sponge Psammaplysilla purea. Tetrahedron Lett., 1986, 26(37), 4517-4520.
[58]
Jumaryatno, P.; Blanchfield, J.; Garson, M. New bromotyrosine derivative from Australian sponge 27th International Symposium on the Chemistry of Natural Products and 7th International Conference on Biodiversity, Queensland, Australia, 2011, pp. 10-15.
[59]
Wu, H.; Nakamura, H.; Kobayashi, J.; Ohizumi, Y.; Hirata, Y. Lipopurealins, novel bromotyrosine derivatives with long chain acyl groups, from the marine sponge Psammaplysilla purea. Cell. Mol. Life Sci., 1986, 42(7), 855-856.
[http://dx.doi.org/10.1007/BF01941553]
[60]
Kobayashi, J.; Honma, K.; Tsuda, M.; Kosaka, T. Lipopurealins D and E and purealidin H, new bromotyrosine alkaloids from the Okinawan marine sponge Psammaplysilla purea. J. Nat. Prod., 2004, 58(3), 197-200.
[http://dx.doi.org/10.1021/np50117a022]
[61]
Ishibashi, M.; Tsuda, M.; Ohizumi, Y.; Sasaki, T.; Kobayashi, J. Purealidin A, a new cytotoxic bromotyrosine-derived alkaloid from the Okinawan marine sponge Psammaplysilla purea. Experientia, 1991, 47(3), 299-300.
[http://dx.doi.org/10.1007/BF01958166] [PMID: 2009943]
[62]
Kobayashi, J.I.; Tsuda, M.; Agemi, K.; Shigemori, H.; Ishibashi, M.; Sasaki, T. Purealidins B and C, new bromotyrosine alkaloids from the Okinawan marine sponge Psammaplysilla purea. Tetrahedron, 1991, 47(33), 6617-6622.
[http://dx.doi.org/10.1016/S0040-4020(01)82314-0]
[63]
Tsuda, M.; Shigemori, H.; Ishibashi, M.; Kobayashi, J. Purealidin D, a new pyridine alkaloid from the okinawan marine sponge Psammaplysilla purea. Tetrahedron Lett., 1992, 33(18), 2597-2598.
[http://dx.doi.org/10.1016/S0040-4039(00)92253-6]
[64]
Tsuda, M.; Shigemori, H.; Ishibashi, M.; Kobayashi, J. Purealidins E-G, New bromotyrosine alkaloids from the Okinawan marine sponge Psammaplysilla purea. J. Nat. Prod., 1992, 55(9), 1325-1327.
[http://dx.doi.org/10.1021/np50087a026]
[65]
Kobayashi, J.I.; Honma, K.; Sasaki, T.; Tsuda, M. Purealidins J-R, new bromotyrosine alkaloids from the Okinawan marine sponge Psammaplysilla purea. Chem. Pharm. Bull. (Tokyo), 1995, 43(3), 403-407.
[http://dx.doi.org/10.1248/cpb.43.403]
[66]
Tabudravu, J.N.; Jaspars, M. Purealidin S and purpuramine J, bromotyrosine alkaloids from the Fijian marine sponge Druinella sp. J. Nat. Prod., 2002, 65(12), 1798-1801.
[http://dx.doi.org/10.1021/np020275n] [PMID: 12502317]
[67]
Roll, D.M.; Chang, C.W.J.; Scheuer, P.J.; Gray, G.A.; Shoolery, J.N.; Matsumoto, G.K.; Van Duyne, G.D.; Clardy, J. Structure of the psammaplysins. J. Am. Chem. Soc., 1985, 107(10), 2916-2920.
[http://dx.doi.org/10.1021/ja00296a014]
[68]
Yagi, H.; Matsunaga, S.; Fusetani, N. Purpuramines A-I, new bromotyrosine-derived metabolites from the marine sponge Psammaplysilla purpurea. Tetrahedron, 1993, 49(18), 3749-3754.
[http://dx.doi.org/10.1016/S0040-4020(01)90227-3]
[69]
Jurek, J.; Yoshida, W.Y.; Scheuer, P.J.; Kelly-Borges, M. Three new bromotyrosine-derived metabolites of the sponge Psammaplysilla purpurea. J. Nat. Prod., 1993, 56(9), 1609-1612.
[http://dx.doi.org/10.1021/np50099a025]
[70]
Longeon, A.; Guyot, M.; Vacelet, J. Araplysillins-I and-II: biologically active dibromotyrosine derivatives from the sponge Psammaplysilla arabica. Cell. Mol. Life Sci., 1990, 46(5), 548-550.
[http://dx.doi.org/10.1007/BF01954262]
[71]
Gunasekera, M.; Gunasekera, S.P. Dihydroxyaerothionin and aerophobin 1. Two brominated tyrosine metabolites from the deep water marine sponge Verongula rigida. J. Nat. Prod., 1989, 52(4), 753-756.
[http://dx.doi.org/10.1021/np50064a014] [PMID: 2530314]
[72]
Carroll, A.R.; Kaiser, S.M.; Davis, R.A.; Moni, R.W.; Hooper, J.N.; Quinn, R.J. A bastadin with potent and selective delta-opioid receptor binding affinity from the Australian sponge Ianthella flabelliformis. J. Nat. Prod., 2010, 73(6), 1173-1176.
[http://dx.doi.org/10.1021/np100010z] [PMID: 20575589]
[73]
Niemann, H.; Lin, W.; Müller, W.E.; Kubbutat, M.; Lai, D.; Proksch, P. Trimeric hemibastadin congener from the marine sponge Ianthella basta. J. Nat. Prod., 2013, 76(1), 121-125.
[http://dx.doi.org/10.1021/np300764u] [PMID: 23249297]
[74]
Carney, J.R.; Scheuer, P.J.; Kelly-Borges, M. A new bastadin from the sponge Psammaplysilla purpurea. J. Nat. Prod., 1993, 56(1), 153-157.
[http://dx.doi.org/10.1021/np50091a025] [PMID: 8383731]
[75]
Coll, J.C.; Kearns, P.S.; Rideout, J.A.; Sankar, V. Bastadin 21, a novel isobastarane metabolite from the Great Barrier Reef marine sponge Ianthella quadrangulata. J. Nat. Prod., 2002, 65(5), 753-756.
[http://dx.doi.org/10.1021/np010520n] [PMID: 12027760]
[76]
Mukai, H.; Kubota, T.; Aoyama, K.; Mikami, Y.; Fromont, J.; Kobayashi, J. Tyrokeradines A and B, new bromotyrosine alkaloids with an imidazolyl-quinolinone moiety from a verongid sponge. Bioorg. Med. Chem. Lett., 2009, 19(5), 1337-1339.
[http://dx.doi.org/10.1016/j.bmcl.2009.01.056] [PMID: 19201605]
[77]
El-Demerdash, A.; Moriou, C.; Toullec, J.; Besson, M.; Soulet, S.; Schmitt, N.; Petek, S.; Lecchini, D.; Debitus, C.; Al-Mourabit, A. Bioactive Bromotyrosine-Derived Alkaloids from the Polynesian Sponge Suberea ianthelliformis. Mar. Drugs, 2018, 16(5)E146
[http://dx.doi.org/10.3390/md16050146] [PMID: 29702602]
[78]
Zhang, H.; Conte, M.M.; Capon, R.J. Franklinolides A-C from an Australian marine sponge complex: phosphodiesters strongly enhance polyketide cytotoxicity. Angew. Chem. Int. Ed. Engl., 2010, 49(51), 9904-9906.
[http://dx.doi.org/10.1002/anie.201005883] [PMID: 21082643]
[79]
Sirirath, S.; Tanaka, J.; Ohtani, I.I.; Ichiba, T.; Rachmat, R.; Ueda, K.; Usui, T.; Osada, H.; Higa, T. Bitungolides A-F, new polyketides from the Indonesian sponge Theonella cf. swinhoei. J. Nat. Prod., 2002, 65(12), 1820-1823.
[http://dx.doi.org/10.1021/np0200865] [PMID: 12502321]
[80]
Utkina, N.K.; Fedoreyev, S.A.; Ilyin, S.G.; Antipin, M.Y. 3,5-Dibromo-2-methoxybenzoic acid from sea sponge Didiscus sp. Russ. Chem. Bull., 1998, 47(11), 2292-2294.
[http://dx.doi.org/10.1007/BF02494298]
[81]
Liu, H.; Lohith, K.; Rosario, M.; Pulliam, T.H.; O’Connor, R.D.; Bell, L.J.; Bewley, C.A. Polybrominated diphenyl ethers: structure determination and trends in antibacterial activity. J. Nat. Prod., 2016, 79(7), 1872-1876.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00229] [PMID: 27399938]
[82]
Sun, S.; Canning, C.B.; Bhargava, K.; Sun, X.; Zhu, W.; Zhou, N.; Zhang, Y.; Zhou, K. Polybrominated diphenyl ethers with potent and broad spectrum antimicrobial activity from the marine sponge Dysidea. Bioorg. Med. Chem. Lett., 2015, 25(10), 2181-2183.
[http://dx.doi.org/10.1016/j.bmcl.2015.03.057] [PMID: 25863431]
[83]
Yamazaki, H.; Sumilat, D.A.; Kanno, S.; Ukai, K.; Rotinsulu, H.; Wewengkang, D.S.; Ishikawa, M.; Mangindaan, R.E.; Namikoshi, M. A polybromodiphenyl ether from an Indonesian marine sponge Lamellodysidea herbacea and its chemical derivatives inhibit protein tyrosine phosphatase 1B, an important target for diabetes treatment. J. Nat. Med., 2013, 67(4), 730-735.
[http://dx.doi.org/10.1007/s11418-012-0735-y] [PMID: 23274914]
[84]
Utkina, N.K.; Denisenko, V.A.; Scholokova, O.V.; Virovaya, M.V.; Gerasimenko, A.V.; Popov, D.Y.; Krasokhin, V.B.; Popov, A.M. Spongiadioxins A and B, two new polybrominated dibenzo-p-dioxins from an Australian marine sponge Dysidea dendyi. J. Nat. Prod., 2001, 64(2), 151-153.
[http://dx.doi.org/10.1021/np0003544] [PMID: 11434317]

Rights & Permissions Print Cite
Article Metrics
49
2
Wayfinder Image
Open Access Journals Promotions
World Antimicrobial Awareness Week
© 2024 Bentham Science Publishers | Privacy Policy