Theonellamide G, a potent antifungal and cytotoxic bicyclic glycopeptide from the red sea marine sponge Theonella swinhoei

Marine Drugs

Volumn 12, Issue 4, 2014, Pages 1911-1923

  Youssef, Diaa T A ^a   Shaala, Lamiaa A ^a,b   Mohamed, Gamal A ^a,c   Badr, Jihan M ^a,d   Bamanie, Faida H ^e   Ibrahim, Sabrin R M ^f,g  

^a KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^b Suez Canal University Hospital   (Egypt)

^c Al Azhar University   (Egypt)

^d Suez Canal University   (Egypt)

^e Aziz University   (Saudi Arabia)

^f Assiut University   (Egypt)

^g TAIBAH UNIVERSITY   (Saudi Arabia)

Author keywords

Antifungal activity; Cytotoxic activity; Glycopeptide; Theonella swinhoei; Theonellamide G

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; CYTOTOXIC AGENT; ETOPOSIDE; GLYCOPEPTIDE; THEONELLAMIDE G; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CYCLOPEPTIDE;

ADENOCARCINOMA CELL LINE; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE (PORIFERA); THEONELLA SWINHOEI; ADENOCARCINOMA; ANIMAL; CHEMISTRY; COLONIC NEOPLASMS; DRUG EFFECTS; HCT116 CELL LINE; IC50; INDIAN OCEAN; ISOLATION AND PURIFICATION; PATHOLOGY; THEONELLA;

ADENOCARCINOMA; ANIMALS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; CANDIDA ALBICANS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLONIC NEOPLASMS; GLYCOPEPTIDES; HCT116 CELLS; HUMANS; INDIAN OCEAN; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES, CYCLIC; THEONELLA;

EID: 84900400406     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12041911     Document Type: Article

References (25)

1. Winder, P.L.; Pomponi, S.A.; Wright, A.E. Natural Products from the Lithistida: A Review of the Literature since 2000. Mar. Drugs 2011, 9, 2643-2682.
2. Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.G.H.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2013, 30, 237-323.
3. Schmidt, E.W.; Harper, M.K.; Faulkner, D.J. Mozamides A and B, cyclic peptides from a Theonellid sponge from Mozambique. J. Nat. Prod. 1997, 60, 779-782. (Pubitemid 27372000)
4. Hamada, T.; Suyawara, T.; Matsunaga, S.; Fusetani, N. Polytheonamides, unprecedented highly cytotoxic polypeptides from the marine sponge Theonella swinhoei 2. Structure elucidation. Tetrahedron Lett. 1994, 35, 609-612.
5. Nakao, Y.; Oku, N.; Matsunaga, S.; Fusetani, N. Cyclotheonamides E2 and E3, new potent serine protease inhibitors from the marine sponge of the genus Theonella. J. Nat. Prod. 1998, 61, 667-670. (Pubitemid 28262042)
6. Kobayashi, M.; Kanzaki, K.; Katayama, S.; Ohashi, K.; Okada, H.; Ikegami, S.; Kitagawa, I. Marine natural products. XXXIII. Theonellapeptolide IId, a new tridecapeptide lactone from the Okinawan marine sponge Theonella swinhoei. Chem. Pharm. Bull. 1994, 42, 1410-1415. (Pubitemid 24244084)
7. Matsunaga, S.; Fusetani, N. Theonellamides A-E, cytotoxic bicyclic peptides, from a marine sponge Theonella sp. J. Org. Chem. 1995, 60, 1177-1181.
8. Bewley, C.A.; Faulkner, D.J. Theonegramide, an antifungal glycopeptides from the Philippine Lithistid Sponge Theonella swinhoei. J. Org. Chem. 1994, 59, 4849-4852. (Pubitemid 24291842)
9. Kobayashi, J.; Itagaki, F.; Shigemori, H.; Takao, T.; Shimonishi, Y. Keramamides E, G, H, and J, new cyclic peptides containing an oxazole or a thiazole ring from a Theonella sponge. Tetrahedron 1995, 51, 2525-2532.
10. de Silva, E.D.; Williams, D.E.; Andersen, R.J.; Klix, H.; Holmes, C.F.B.; Allen, T.M. A potent protein phosphatase inhibitor isolated from the Papau New Guinea sponge Theonella swinhoei Gray. Tetrahedron Lett. 1992, 33, 1561-1564.
11. Schmidt, E.W.; Faulkner, D.J. Microsclerodermins C-E, antifungal cyclic peptides from the lithistid sponges Theonella sp. and Microscleroderma sp. Tetrahedron 1998, 54, 3043-3056. (Pubitemid 28153289)
12. Bonnington, L.S.; Tanaka, J.; Higa, T.; Kimura, J.; Yoshimura, Y.; Nakao, Y.; Yoshida, W.Y.; Scheuer, P.J. Cupolamide A: A cytotoxic cyclic heptapeptide from two samples of the sponge Theonella cupola. J. Org. Chem. 1997, 62, 7765-7767. (Pubitemid 127494425)
13. Chill, L.; Kashman, Y.; Schleyer, M. Oriamide, a new cytotoxic cyclic peptide containing a novel amino acid from the marine sponge Theonella sp. Tetrahedron 1997, 53, 16147-16152. (Pubitemid 27496093)
14. Clark, D.P.; Carroll, J.; Naylor, S.; Crews, P. An antifungal cyclodepsipeptide, cyclolithistide A from the sponge Theonella swinhoei. J. Org. Chem. 1998, 63, 8757-8764. (Pubitemid 28557527)
15. Schmidt, E.W.; Bewley C.A.; Faulkner, D.J. Theopalauamide, a bicyclic glycopeptide from filamentous bacterial symbionts of the Lithistid sponge Theonella swinhoei from Palau and Mozambique. J. Org. Chem. 1998, 63, 1254-1258. (Pubitemid 128499790)
16. Ford, P.W.; Gustafson, K.R.; McKee, T.C.; Shigematsu, N.; Maurizi, L.K.; Pannell, L.K.; Williams, D.E.; de Silva, E.D.; Lassota, P.; Allen, T.M.; et al. Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei collected in Papua New Guinea. J. Am. Chem. Soc. 1999, 121, 5899-5909.
17. Youssef, D.T.A.; Mooberry, S.L. Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the Red Sea sponge Theonella swinhoei. J. Nat. Prod. 2006, 69, 154-157. (Pubitemid 43241777)
18. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Wälchlit, M. Theonellamide F. A novel antifungal bicyclic peptide from a marine sponge Theonella sp. J. Am. Chem. Soc. 1989, 111, 2582-2588.
19. Nishimura, S.; Arita, Y.; Honda, M.; Iwamoto, K.; Matsuyama, A.; Shirai, A.; Kawasaki, H.; Kakeya, H.; Kobayashi, T.; Matsunaga, S.; et al. Marine antifungal theonellamides target 3β-hydroxysterol to activate Rho1 signaling. Nat. Chem. Biol. 2010, 6, 519-526.
20. Espiritu, R.A.; Matsumori, N.; Murata, M.; Nishimura, S.; Kakeya, H.; Matsunaga, S.; Yoshida, M. Interaction between the marine sponge cyclic peptide theonellamide A and sterols in lipid bilayers as viewed by surface plasmon resonance and solid-state (2)H nuclear magnetic resonance. Biochemistry 2013, 52, 2410-2418.
21. Nishimura, S.; Ishii, K.; Iwamoto, K.; Arita, Y.; Matsunaga, S.; Ohno-Iwashita, Y.; Sato, S.B.; Kakeya, H.; Kobayashi, T.; Yoshida, M. Visualization of sterol-rich membrane domains with fluorescently-labeled theonellamides. PLoS One 2013, 8, e83716.
22. Ibrahim, S.R.M.; Min, C.C.; Teuscher, F.; Ebel, R.; Kakoschke, C.; Lin, W.; Wray, V.; Edrada-Ebel, R.; Proksch, P. Callyaerins A-F and H, new cytotoxic cyclic peptides from the Indonesian marine sponge Callyspongia aerizusa. Bioorg. Med. Chem. 2010, 18, 4947-4956.
23. Ibrahim, S.R.M.; Edrada-Ebel, R.; Mohamed, G.A.; Youssef, D.T.A.; Wray, V.; Proksch, P. Callyaerin G, a new cytotoxic cyclic peptide from the marine sponge Callyspongia aerizusa. ARKIVOC 2008, 2008, 164-171.
24. Soria-Mercado, I.E.; Prieto-Davo, A.; Jensen, P.R.; Fenical, W. Antibiotic terpenoid chlorodihydroquinones from a new marine actinomycete. J. Nat. Prod. 2005, 68, 904-910. (Pubitemid 41017505)
25. Clinical and Laboratory Standards Institute (CLSI). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 8th ed.; CLSI Document M7-A8; CLSI: Wayne, PA, USA, 2009.