RSS-Feed abonnieren
DOI: 10.1055/s-2008-1074506
© Georg Thieme Verlag KG Stuttgart · New York
New Bioactive Bromotyrosine-Derived Alkaloid from a Marine Sponge Aplysinella sp.
Publikationsverlauf
Received: July 4, 2007
Revised: February 6, 2008
Accepted: March 12, 2008
Publikationsdatum:
10. April 2008 (online)

Abstract
A new bromotyrosine-derived alkaloid, (+)-aplysinillin (1), together with seven known compounds, was isolated from the crude organic extract of the marine sponge Aplysinella sp. collected from the Federated States of Micronesia. The structure of 1 was deduced by NMR and mass spectral techniques. Compounds 1 - 8 were evaluated for their inhibitory activity with the hyphae formation inhibition assay in Streptomyces 85E. Compounds 1 and 8 exhibited antiproliferative activities against the human breast adenocarcinoma cancer cell line MCF-7.
Key words
Bromotyrosine alkaloids - protein phosphorylation inhibitors - marine sponge, Aplysinella sp. - hyphae formation inhibition
References
- 1 Waters B, Saxena G, Wanggui Y, Kau D, Wrigley S, Stokes R. et al . Identification of protein kinase inhibitors using an assay based on inhibition of aerial hyphae formation in Streptomyces. J Antibiot. 2002; 55 407-16
- 2 Hong S K, Matsumota A, Horinochi S, Beppu T. Effects of protein kinase inhibitors on in vitro protein phosphorylation and cellular differentiation of Streptomyces griseus. Mol Gen Genet. 1993; 236 347-54
- 3 Ichiba T, Scheuer P J, Kelly-Borges M. Three bromotyrosine derivatives, one terminating in an unprecedented diketocyclopentanylidene enamine. J Org Chem. 1993; 58 4149-50
- 4 Rao M R, Venkatesham U, Sridevi K V, Venkateswarlu Y. Chemical constituents and their biological activities of the sponge family Aplysinellidae: A review. Indian J Chem. 2000; 39B 723-33
- 5 Gao H, Kelly M, Hamann M T. Bromotyrosine-derived metabolites from the sponge Aiolochroia crassa. Tetrahedron. 1999; 55 9717-26
- 6 Gillies R J, Didier N, Denton M. Determination of cell number in monolayer cultures. Anal Biochem. 1986; 159 109-13
- 7 Ciminiello P, Costantino V, Fattorusso E, Magno S, Mangoni A. Chemistry of Verongida sponges, II. Constituents of the Caribbean sponge Aplysina fistularis form a fulva. J Nat Prod. 1994; 57 705-12
- 8 Ciminiello P, Dell’Aversano C, Fattorusso E, Magno S, Carrano L, Pansini M. Chemistry of Verongida sponges. VII Bromocompounds from the Caribbean sponge Aplysina archeri. Tetrahedron. 1996; 52 9863-8
- 9 Konig M G, Wright A D. Agelorins A and B, and 11-epi-fistularin-3, three new antibacterial fistularin-3 derivatives from the tropical marine sponge Agelas oroides. Heterocycles. 1993; 36 1351-9
- 10 Ogamino T, Obata R, Nishiyama S. Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative. Tetrahedron Lett. 2006; 47 727-31
- 11 McMillan J A, Paul I C, Goo Y M, Rinehart KL J r. An x-ray study of aerothionin from Aplysina fistularis (Pallas). Tetrahedron Lett. 1981; 22 39-42
- 12 Moody K, Thomson R H, Fattorusso E, Minale L, Sodano G. Aerothionin and homoaerothionin: two tetrabromo spirocyclohexadienylisoxazoles from Verongia sponges. J Chem Soc [Perkin I] 1972: 18-24
- 13 Roll D M, Chang C WJ, Scheuer P J, Gray G A, Shoolery J N, Matsumoto G K. et al . Structure of the psammaplysins. J Am Chem Soc. 1985; 107 2916-20
- 14 Rotem M, Carmely S, Kashman Y, Loya Y. Two new antibiotics from the red sea sponge Psammaplysilla purpurea. Tetrahedron. 1983; 39 667-76
- 15 Longeon A, Guyot M, Vacelet J. Araplysillins-I and II: Biologically active dibromotyrosine derivatives from the sponge Psammaplysilla arabica. Experientia. 1990; 46 548-50
- 16 Capon R J, MacLeod J K. Two epimeric dibromo nitriles from the Australian sponge Aplysina laevis. Aust J Chem. 1987; 40 341-6
- 17 D’Ambroiso M, Guerriero A, Traldi P, Pietra F. Cavernicolin-1 and cavernicolin-2, two epimeric dibromolactams from the Mediterranean sponge Aplysina (Verongia) cavernicola. Tetrahedron Lett. 1982; 23 4430-506
- 18 Kijjio A, Watanadilok R, Sonchaeng P, Sawangwong P, Pedro M, Nascimento M SJ. et al . Further halotyrosine derivatives from the marine sponge Suberea aff. Praetensa. Z Naturforsch. 2002; 57 732-8
- 19 Sharma G M, Burkholder P R. Studies on the antimicrobial substances of the sponges II. Structure and synthesis of a bromine-containing antibacterial compound from a marine sponge. Tetrahedron Lett. 1967; 42 4147-50
Dr. Leng Chee Chang
College of Pharmacy
University of Hawaii Hilo
60 Nowelo St., Suite 101
Hilo
HI, 96720
USA
Telefon: +1-808-443-5900
Fax: +1 808-443-5903
eMail: lengchee@hawaii.edu