New antimicrobial bromotyrosine analogues from the sponge Pseudoceratina purpurea and its predator Tylodina corticalis

Marine Drugs

Volumn 13, Issue 3, 2015, Pages 1389-1409

  Gotsbacher, Michael P ^a   Karuso, Peter ^a  

^a MACQUARIE UNIVERSITY   (Australia)

Author keywords

Alkaloid; Antibiotics; Bromotyrosine; Marine natural products; Pseudoceratina; Sponge; Tylodina

Indexed keywords

16 DEBROMOAPLYSAMINE 4; AEROPHOBIN 2; ANTIINFECTIVE AGENT; APLYSAMINE 2; APLYSAMINE 8; BROMOTYROSINE DERIVATIVE; CERATINADIN D; HEXADELLIN A; NATURAL PRODUCT; PSEUDOCERATINA PURPUREA EXTRACT; PSEUDOCERATININ A; PUREALIN; TYLODINA CORTICALIS EXTRACT; UNCLASSIFIED DRUG; ALKALOID; BROMOTYROSINE; TYROSINE;

ANTIBACTERIAL ACTIVITY; ARTICLE; AUSTRALIA; BIOACCUMULATION; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; DRUG ISOLATION; DRUG STRUCTURE; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLLUSC; NONHUMAN; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOCERATINA PURPUREA; SPONGE (PORIFERA); STAPHYLOCOCCUS AUREUS; TYLODINA CORTICALIS; ULTRAVIOLET SPECTROSCOPY; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; FOOD CHAIN; GASTROPOD; ISOLATION AND PURIFICATION; METABOLISM;

MOLLUSCA; PSEUDOCERATINA; TYLODINA;

ALKALOIDS; ANIMALS; ANTI-INFECTIVE AGENTS; AUSTRALIA; FOOD CHAIN; GASTROPODA; PORIFERA; TYROSINE;

EID: 84925879078     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md13031389     Document Type: Article

References (58)

1. Harper, M. K.; Bugni, T. S.; Copp, B. R.; James, R. D.; Lindsay, B. S.; Richardson, A. D.; Schnabel, P. C.; Tasdemir, D.; Van Wagoner, R. M.; Verbitski, S. M.; et al. Introduction to the chemical ecology of marine natural products. In Marine Chemical Ecology; McClintock, J. B., Baker, B. J., Eds.; CRC Press LLC: Boca Raton, FL, USA, 2001; pp. 3-69.
2. Bergquist, P. R.; Wells, R. J. Chemotaxonomy of the Porifera: The development and current status of the field. In Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, NY, USA, 1983.
3. Bergquist, P. R.; Karuso, P.; Cambie, R. C.; Smith, D. J. Sterol composition and classification of the Porifera. 3. Biochem. Syst. Ecol. 1991, 19, 17-24.
4. Arabshahi, L.; Schmitz, F. J. Brominated tyrosine metabolites from an unidentified sponge. J. Org. Chem. 1987, 52, 3584-3586.
5. Teeyapant, R.; Kreis, P.; Wray, V.; Witte, L.; Proksch, P. Brominated secondary compounds from the marine sponge Verongia aerophoba and the sponge feeding gastropod Tylodina perversa. Z. Naturforsch. C: Biosci. 1993, 48, 640-644.
6. Shaala, L. A.; Bamane, F. H.; Badr, J. M.; Youssef, D. T. A. Brominated arginine-derived alkaloids from the red sea sponge Suberea mollis. J. Nat. Prod. 2011, 74, 1517-1520.
7. Salim, A. A.; Khalil, Z. G.; Capon, R. J. Structural and stereochemical investigations into bromotyrosine-derived metabolites from southern Australian marine sponges, Pseudoceratina spp. Tetrahedron 2012, 68, 9802-9807.
8. Jang, J.-H.; Van Soest, R. W. M.; Fusetani, N.; Matsunaga, S. Pseudoceratins A and B, antifungal bicyclic bromotyrosine-derived metabolites from the marine sponge Pseudoceratina purpurea. J. Org. Chem. 2007, 72, 1211-1217.
9. Kon, Y.; Kubota, T.; Shibazaki, A.; Gonoi, T.; Kobayashi, J. I.; Ceratinadins, A.-C. New bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp. Bioorg. Med. Chem. Lett. 2010, 20, 4569-4572.
10. 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, 1609-1612.
11. 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. 1995, 43, 403-407.
12. Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. Ceratinamides A and B: New antifouling dibromotyrosine derivatives from the marine sponge Pseudoceratina purpurea. Tetrahedron 1996, 52, 8181-8186.
13. Compagnone, R. S.; Avila, R.; Suarez, A. I.; Abrams, O. V.; Rangel, H. R.; Arvelo, F.; Pina, I. C.; Merentes, E. 11-Deoxyfistularin-3, a new cytotoxic metabolite from the Caribbean sponge Aplysina fistularis insularis. J. Nat. Prod. 1999, 62, 1443-1444.
14. Tabudravu, J. N.; Jaspars, M. Purealidin S and purpuramine J, bromotyrosine alkaloids from the Fijian marine sponge Druinella sp. J. Nat. Prod. 2002, 65, 1798-1801.
15. Kalaitzis, J. A.; De, A. L. P.; Hooper, J. N. A.; Quinn, R. J. Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp. Nat. Prod. Res. 2008, 22, 1257-1263.
16. Teruya, T.; Iwasaki, A.; Suenaga, K. 20-N-methylpurpuramine E: New bromotyrosine-derived metabolite from Okinawan marine sponge Pseudoceratina purpurea. Bull. Chem. Soc. Jpn. 2008, 81, 1026-1027.
17. Proksch, P.; Putz, A.; Ortlepp, S.; Kjer, J.; Bayer, M. Bioactive natural products from marine sponges and fungal endophytes. Phytochem. Rev. 2010, 9, 475-489.
18. Su, J.-H.; Chen, Y.-C.; El-Shazly, M.; Du, Y.-C.; Su, C.-W.; Tsao, C.-W.; Liu, L.-L.; Chou, Y.; Chang, W.-B.; Su, Y.-D.; et al. Towards the small and the beautiful: A small dibromotyrosine derivative from Pseudoceratina sp. sponge exhibits potent apoptotic effect through targeting IKK/NFκB signaling pathway. Mar. Drugs 2013, 11, 3168-3185.
19. Shaala, L. A.; Youssef, D. T. A.; Sulaiman, M.; Behery, F. A.; Foudah, A. I.; El Sayed, K. A. Subereamolline A as a potent breast cancer migration, invasion and proliferation inhibitor and bioactive dibrominated alkaloids from the Red Sea sponge Pseudoceratina arabica. Mar. Drugs 2012, 10, 2492-2508.
20. Niemann, H.; Lin, W.; Mueller, W. E. G.; Kobbutat, M.; Lai, D.; Proksch, P. Trimeric hemibastadin congener from the marine sponge Ianthella basta. J. Nat. Prod. 2013, 76, 121-125.
21. Tran, T. D.; Pham, N. B.; Fechner, G.; Hooper, J. N. A.; Quinn, R. J. Bromotyrosine alkaloids from the Australian marine sponge Pseudoceratina verrucosa. J. Nat. Prod. 2013, 76, 516-523.
22. 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, 846-848.
23. Galeano, E.; Thomas, O. P.; Robledo, S.; Munoz, D.; Martinez, A. Antiparasitic bromotyrosine derivatives from the marine sponge Verongula rigida. Mar. Drugs 2011, 9, 1902-1913.
24. Mani, L.; Jullian, V.; Mourkazel, B.; Valentin, A.; Dubois, J.; Cresteil, T.; Folcher, E.; Hooper, J. N. A.; Erpenbeck, D.; Aalbersberg, W.; et al. New antiplasmodial bromotyrosine derivatives from Suberea ianthelliformis Lendenfeld, 1888. Chem. Biodivers. 2012, 9, 1436-1451.
25. Karuso, P. Chemical ecology of the nudibranchs. Bioorg. Mar. Chem. 1987, 1, 31-60.
26. Hao, E.; Fromont, J.; Jardine, D.; Karuso, P. Natural products from sponges of the genus Agelas-on the trail of a [2 + 2]-photoaddition enzyme. Molecules 2001, 6, 130-141.
27. Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. Pseudoceratidine: A new antifouling spermidine derivative from the marine sponge Pseudoceratina purpurea. Tetrahedron Lett. 1996, 37, 1439-1440.
28. Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. Pseudoceramine: An unprecedented antifouling cyanoformamide from the marine sponge Pseudoceratina purpurea. J. Org. Chem. 1996, 61, 2936-2937.
29. Fusetani, N.; Masuda, Y.; Nakao, Y.; Matsunaga, S.; Van Soest, R. W. M. Three new bromotyrosine derivatives lethal to crab from the marine sponge, Pseudoceratina purpurea. Tetrahedron 2001, 57, 7507-7511.
30. Takada, N.; Watanabe, R.; Suenaga, K.; Yamada, K.; Ueda, K.; Kita, M.; Uemura, D. Zamamistatin, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea. Tetrahedron Lett. 2001, 42, 5265-5267.
31. Peng, X.; Deng, S.; Xiao, D.; Wu, H. Chemical constituents of the marine sponge Pseudoceratina purpurea from South China Sea (I). Guangzhou Huaxue 2003, 28, 1-4.
32. Peng, X.; Deng, S.; Xiao, D.; Ma, W.; Wu, H. Studies on the active constituents of the marine sponge Pseudoceratina purpurea from the South China Sea. Zhongguo Haiyang Yaowu 2004, 23, 11-13.
33. Kijjoa, A.; Bessa, J.; Wattanadilok, R.; Sawangwong, P.; Nascimento, M. S. J.; Pedro, M.; Silva, A. M. S.; Eaton, G.; Van Soest, R.; Herz, W. Dibromotyrosine derivatives, a maleimide, aplysamine-2 and other constituents of the marine sponge Pseudoceratina purpurea. Z. Naturforsch. B Chem. Sci. 2005, 60, 904-908.
34. Hertiani, T.; Edrada, R.; Van, S. R. W. M.; Mueller, W. E. G.; Sudarsono Proksch, P. Chemical investigation on Pseudoceratina purpurea collected from Banyuwangi Indonesia. Indonesian J. Pharm. 2009, 20, 17-26.
35. McCulloch, M. W. B.; Coombs, G. S.; Banerjee, N.; Bugni, T. S.; Cannon, K. M.; Harper, M. K.; Veltri, C. A.; Virshup, D. M.; Ireland, C. M. Psammaplin A as a general activator of cell-based signaling assays via HDAC inhibition and studies on some bromotyrosine derivatives. Biorg. Med. Chem. 2009, 17, 2189-2198.
36. Faulkner, D.; Ghiselin, M. Chemical defense and evolutionary ecology of dorid nudibranchs and some other opisthobranch gastropods. Mar. Ecol. 1983, 13, 295-301.
37. Ebel, R.; Marin, A.; Proksch, P. Organ-specific distribution of dietary alkaloids in the marine opisthobranch Tylodina perversa. Biochem. Syst. Ecol. 1999, 27, 769-777.
38. Thoms, C.; Ebel, R.; Hentschel, U.; Proksch, P. Sequestration of dietary alkaloids by the spongivorous marine mollusk Tylodina perversa. Z. Naturforsch. C: Biosci. 2003, 58, 426-432.
39. Thoms, C.; Ebel, R.; Proksch, P. Sequestration and possible role of dietary alkaloids in the sponge-feeding mollusk Tylodina perversa. Prog. Mol. Subcell. Biol. 2006, 43, 261-275.
40. Ciminiello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Pansini, M. Chemistry of verongida sponges. VIII. Bromo compounds from the Mediterranean sponges Aplysina aerophoba and Aplysina cavernicola. Tetrahedron 1997, 53, 6565-6572.
41. Encarnacion, R. D.; Sandoval, E.; Malmstrom, J.; Christophersen, C. Calafianin, a bromotyrosine derivative from the marine sponge Aplysina gerardogreeni. J. Nat. Prod. 2000, 63, 874-875.
42. Fendert, T.; Wray, V.; Van Soest, R. W. M.; Proksch, P. Bromoisoxazoline alkaloids from the Caribbean sponge Aplysina insularis. Z. Naturforsch. C: Biosci. 1999, 54, 246-252.
43. Venkateswarlu, Y.; Rao, M. R.; Venkatesham, U. A new dibromotyrosine-derived metabolite from the sponge Psammaplysilla purpurea. J. Nat. Prod. 1998, 61, 1388-1389.
44. Cimino, G.; De Rosa, S.; De Stefano, S.; Spinella, A.; Sodano, G. The zoochrome of the sponge Verongia aerophoba ("Uranidine"). Tetrahedron Lett. 1984, 25, 2925-2928.
45. Benharref, A.; Pais, M.; Debitus, C. Bromotyrosine alkaloids from the sponge Pseudoceratina verrucosa. J. Nat. Prod. 1996, 59, 177-180.
46. Cimino, G.; Rosa, S. D.; Stefano, S. D.; Self, R.; Sodano, G. The bromo-compounds of the true sponge Verongia aerophoba. Tetrahedron Lett. 1983, 24, 3029-3032.
47. Morris, S. A.; Andersen, R. J. Nitrogenous metabolites from the deep water sponge Hexadella sp. Can. J. Chem. 1989, 67, 677-681.
48. Xynas, R.; Capon, R. J. Two new bromotyrosine-derived metabolites from an Australian marine sponge, Aplysina sp. Aust. J. Chem. 1989, 42, 1427-1433.
49. Pakrashi, S. C.; Achari, B.; Dutta, P. K.; Chakrabarti, A. K.; Giri, C.; Saha, S.; Basa, S. C. Marine products from bay of Bengal: Constituents of the sponge. Tetrahedron 1994, 50, 12009-12014.
50. Nakamura, H.; Wu, H.; Kobayashi, J.; Nakamura, Y.; Ohizumi, Y.; Hirata, Y. Purealin, a novel enzyme activator from the Okinawan marine sponge Psammaplysilla purea. Tetrahedron Lett. 1985, 26, 4517-4520.
51. Peng, J.; Li, J.; Hamann, M. T. The marine bromotyrosine derivatives. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, CA, USA, 2005; Volume 61, pp. 59-262.
52. 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, 1337-1339.
53. Gershenzon, J.; Dudareva, N. The function of terpene natural products in the natural world. Nat. Chem. Biol. 2007, 3, 408-414.
54. Willan, R. C. A review of the diets in the Notaspidea (Mollusca: Opisthobranchia). J. Malacol. Soc. Aust. 1984, 6, 125-142.
55. Thoms, C.; Schupp, P. J. Activated chemical defense in marine sponges-A case study on Aplysinella rhax. J. Chem. Ecol. 2008, 34, 1242-1252.
56. Becerro, M. A.; Turon, X.; Uriz, M. J.; Templado, J. Can a sponge feeder be a herbivore? Tylodina perversa (Gastropoda) feeding on Aplysina aerophoba (Demospongiae). Biol. J. Linn. Soc. 2003, 78, 429-438.
57. Cimino, G.; Sodano, G. Biosynthesis of secondary metabolites in marine mollusks. Top. Curr. Chem. 1993, 167, 77-115.
58. Hooper, J. N. A. "Sponguide". Guide to Sponge Collection and Identification; Queensland Museum: Brisbane, Australia, 2000.