Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research

Marine Drugs

Volumn 11, Issue 11, 2013, Pages 4451-4463

  Teta, Roberta ^a   Irollo, Elena ^b   Della Sala, Gerardo ^a   Pirozzi, Giuseppe ^b   Mangoni, Alfonso ^a   Costantino, Valeria ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b NATIONAL CANCER INSTITUTE   (Italy)

Author keywords

Antitumor activity; Marine natural products; Peptide polyketides hybrids; Smenospongia aurea; Structure elucidation

Indexed keywords

ANTINEOPLASTIC AGENT; DOLAPYRROLIDINONE; RNA 16S; SMENAMIDE A; SMENAMIDE B; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BACTERIAL METABOLISM; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYANOBACTERIUM; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; HUMAN; HUMAN CELL; LUNG CANCER; METABOLITE; METAGENOMICS; NONHUMAN; SMENOSPONGIA AUREA; SPONGE (PORIFERA); SYNECHOCOCCUS SPONGIARUM;

CYANOBACTERIA; SMENOSPONGIA AUREA; SYNECHOCOCCUS SPONGIARUM;

ANIMALS; ANTINEOPLASTIC AGENTS; BASE SEQUENCE; CARIBBEAN REGION; CELL LINE, TUMOR; CYANOBACTERIA; DRUG SCREENING ASSAYS, ANTITUMOR; HALOGENATION; HUMANS; MOLECULAR SEQUENCE DATA; PEPTIDES; POLYKETIDES; PORIFERA; RNA, RIBOSOMAL, 16S;

EID: 84889260237     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11114451     Document Type: Article

References (22)

1. Lamoral-Theys, D.; Fattorusso, E.; Mangoni, A.; Perinu, C.; Kiss, R.; Costantino, V. Evaluation of the Antiproliferative Activity of Diterpene Isonitriles from the Sponge Pseudoaxinella flava in Apoptosis-sensitive and Apoptosis-resistant Cancer Cell Lines. J. Nat. Prod. 2011, 74, 2299-2303.
2. Costantino, V.; Fattorusso, E.; Mangoni, A.; Perinu, C.; Cirino, G.; De Gruttola, L.; Roviezzo, F. Tedanol: A potent anti-inflammatory ent-pimarane diterpene from the Caribbean Sponge Tedania ignis. Bioorg. Med. Chem. 2009, 17, 7542-7547.
3. Bialonska, D.; Zjawiony, J.K. Aplysinopsins-Marine Indole Alkaloids: Chemistry, Bioactivity and Ecological Significance. Mar. Drugs 2009, 7, 166-183.
4. Song, J.; Jeong, W.; Wang, N.; Lee, H.-S.; Sim, C. J.; Oh, K.-B.; Shin, J. Scalarane Sesterterpenes from the Sponge Smenospongia sp. J. Nat. Prod. 2008, 71, 1866-1871.
5. Djura, P.; Stierle, D.B.; Sullivan, B.; Faulkner, D.J.; Arnold, E.V.; Clardy, J. Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (=Polyfibrospongia) echina. J. Org. Chem. 1980, 45, 1435-1441.
6. Aiello, A.; Fattorusso, E.; Menna, M. A new antibiotic chloro-sesquiterpene from the Caribbean sponge Smenospongia aurea. Z. Naturforsch. B 1993, 48, 209-212.
7. Bourguet-Kondracki, M.L.; Martin, M.T.; Guyot, M. Smenoqualone, a novel sesquiterpenoid from the marine sponge Smenospongia sp. Tetrahedron Lett. 1992, 33, 8079-8080.
8. Kazlauskas, R.; Murphy, P.T.; Quinn, R.J.; Wells, R.J. Aplysinopsin, a new tryptophan derivative from a sponge. Tetrahedron Lett. 1977, 18, 61-64.
9. Hollenbeak, K.H.; Schmitz, F.J. Aplysinopsin: Antineoplastic tryptophan derivative from the marine sponge Verongia spengelii. Lloydia 1977, 10, 479-481.
10. Pretsch, E.; Büelhmann, P.; Affolter, M. Structure Determination of Organic Compounds. In Tables of Spectral Data, 3rd ed.; Springer-Verlag Berlin: Heidelberg, Germany, 2000; pp. 83 and 225.
11. Pettit, G.R.; Kamano, Y.; Dufresne, C.; Cerny, R.L.; Herald, C.L.; Schmidt, J.M. Isolation and Structure of the Cytostatic Linear Depsipeptide Dolastatin 15. J. Org. Chem. 1989, 54, 6005-6006.
12. Ghisalberti, E.L. Bioactive tetramic acid metabolites. Stud. Nat. Prod. Chem. 2003, 28, 109-163.
13. Phuwapraisirisan, P.; Matsunaga, S.; Fusetani, N. Mycapolyols A-F, New Cytotoxic Metabolites of Mixed Biogenesis from the Marine Sponge Mycale izuensis. Organic Lett. 2005, 7, 2233-2236.
14. Simmons, T.L.; McPhail, K.L.; Ortega-Barría, E.; Mooberry, S.L.; Gerwick, W.H. Belamide A, a new antimitotic tetrapeptide from a Panamanian marine cyanobacterium. Tetrahedron Lett. 2006, 47, 3387-3390.
15. Edwards, D.J.; Marquez, B.L.; Nogle, L.M.; McPhail, K.; Goeger, D.E.; Roberts, M.A.; Gerwick, W.H. Structure and Biosynthesis of the Jamaicamides, New Mixed Polyketide-Peptide Neurotoxins from the Marine Cyanobacterium Lyngbya majuscula. Chem. Biol. 2004, 11, 817-833.
16. Prawat, H.; Mahidol, C.; Kaweetripob, W.; Wittayalai, S.; Ruchirawat, S. Iodo-sesquiterpene hydroquinone and brominated indole alkaloids from the Thai sponge Smenospongia sp. Tetrahedron 2012, 68, 6881-6886.
17. Boutte, C.; Grubisic, S.; Balthasart, P.; Wilmotte, A. Testing of primers for the study of cyanobacterial molecular diversity by DGGE. J. Microbiol. Methods 2006, 65, 542-550.
18. Erwin, P.M.; Thacker, R.W. Cryptic diversity of the symbiotic cyanobacterium Synechococcus spongiarum among sponge hosts. Mol. Ecol. 2008, 17, 2937-2947.
19. Nakabachi, A.; Ueoka, R.; Oshima, K.; Teta, R.; Mangoni, A.; Gurgui, M.; Oldham, N.J.; van Echten-Deckert, G.; Okamura, K.; Yamamoto, K.; et al. Defensive Bacteriome Symbiont with a Drastically Reduced Genome. Curr. Biol. 2013, 23, 1478-1484.
20. Erwin, P.M.; López-Legentil, S.; Turon, X. Ultrastructure, molecular phylogenetics, and chlorophyll a content of novel cyanobacterial symbionts in temperate sponges. Microb. Ecol. 2012, 64, 771-783.
21. Pettit, G.R.; Kamano, Y.; Herald, C.L.; Tuinman, A.A.; Boettner, F.E.; Kizu, H.; Schmidt, J.M.; Baczynskyj, L.; Tomer, K.B.; Bontems, R.J. The isolation and structure of a remarkable marine animal antineoplastic constituent: Dolastatin 10. J. Am. Chem. Soc. 1987, 109, 6883-6885.
22. Newman, D.J.; Giddings, L.A. Natural products as leads to antitumor drugs. Phytochem. Rev. 2013, 12, 293-304.