Simplexidine, a 4-alkylpyridinium alkaloid from the Caribbean sponge Plakortis simplex

Molecules

Volumn 13, Issue 7, 2008, Pages 1465-1471

  Fattorusso, Ernesto ^a   Romano, Adriana ^a   Scala, Fernando ^a   Taglialatela Scafati, Orazio ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Alkaloids; NMR; Plakortis; Pyridinium; Simplexidin

Indexed keywords

ALKALOID; PYRIDINIUM DERIVATIVE; SIMPLEXIDINE;

ANIMAL; ARTICLE; CENTRAL AMERICA; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLAKORTIS;

ALKALOIDS; ANIMALS; CARIBBEAN REGION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; PLAKORTIS; PYRIDINIUM COMPOUNDS;

EID: 48849112566     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13071465     Document Type: Article

References (15)

1. Costantino, V.; Fattorusso, E.; Menna, M.; Taglialatela-Scafati, O. Chemical Diversity of Bioactive Marine Natural Products: An Illustrative Case Study. Curr. Med. Chem. 2004, 11, 1671-1692.
2. Laroche, M.; Imperatore, C.; Grozdanov, L.; Costantino, V.; Mangoni, A.; Hentschel, U.; Fattorusso, E. Cellular localization of secondary metabolites isolated from the Caribbean sponge Plakortis simplex. Mar. Biol. 2007, 151, 1365-1373.
3. Costantino, V.; Fattorusso, E.; Mangoni, A.; Di Rosa, M.; Ianaro, A. Glycolipids from sponges. 6. Plakoside A and B, two unique prenylated glycosphingolipids with immunosuppressive activity from the marine sponge Plakortis simplex. J. Am. Chem. Soc. 1997, 119, 12465-12470.
4. Costantino, V.; Fattorusso, E.; Mangoni, A.; Di Rosa, M.; Ianaro, A. Glycolipids from sponges. VII. Simplexides, novel immunosuppressive glycolipids from the Caribbean sponge Plakortis simplex. Bioorg. Med. Chem. Lett. 1999, 9, 271-276.
5. Cafieri, F.; Fattorusso, E.; Taglialatela-Scafati, O.; Ianaro, A. Metabolites from the sponge Plakortis simplex. Determination of absolute stereochemistry of plakortin. Isolation and stereostructure of three plakortin related compounds. Tetrahedron 1999, 55, 7045-7056.
6. Campagnuolo, C.; Fattorusso, E.; Romano, A.; Taglialatela-Scafati, O.; Basilico, N.; Parapini, S.; Taramelli, D. Antimalarial polyketide cycloperoxides from the marine sponge Plakortis simplex. Eur. J. Org. Chem. 2005, 23, 5077-5083.
7. Fattorusso, E.; Parapini, S.; Campagnuolo, C.; Basilico, N.; Taglialatela-Scafati, O.; Taramelli, D. Activity against Plasmodium falciparum of cycloperoxide compounds obtained from the sponge Plakortis simplex. J. Antimicrob. Chemother. 2002, 50, 883-888.
8. Campagnuolo, C.; Fattorusso, E.; Taglialatela-Scafati, O. Plakohypaphorines A-C, iodinecontaining alkaloids from the Caribbean sponge Plakortis simplex. Eur. J. Org. Chem. 2003, 2, 284-287.
9. Borrelli, F.; Campagnuolo, C.; Capasso, R.; Fattorusso, E.; Taglialatela-Scafati, O. Iodinated indole alkaloids from Plakortis simplex-New plakohypaphorines and an evaluation of their antihistamine activity. Eur. J. Org. Chem. 2004, 15, 3227-3232.
10. Campagnuolo, C.; Fattorusso, C.; Fattorusso, E.; Ianaro, A.; Pisano, B.; Taglialatela-Scafati, O. Simplakidine A, a unique pyridinium alkaloid from the Caribbean sponge Plakortis simplex. Org. Lett. 2003, 5, 673-676.
11. Sciuto, S.; Chillemi, R.; Piattelli, M. Onium compounds from the red alga Pteroclaudia capillacea. J. Nat. Prod. 1988, 51, 322-325.
12. Laville, R.; Thomas, O. P.; Berrue, F.; Reyes, F.; Amade, P. Pachychalines A-C: novel 3-alkylpyridinium salts from the marine sponge Pachychalina sp. Eur. J. Org. Chem. 2008, 121-125.
13. Schmitz, F. J.; Hollenbeak, K. H.; Campbell, D. C. Marine natural products: Halitoxin, toxic complex of several marine sponges of the genus Haliclona. J. Org. Chem. 1978, 43, 3916-3922.
14. Turk, T.; Frangez, R.; Sepcic, K. Mechanism of toxicity of 3-alkylpyridinium polymers from marine sponge Reniera sarai. Mar. Drugs 2007, 5, 157-167.
15. Kubanek, J.; Andersen, R. J. Evidence for the incorporation of intact butyrate units in the biosynthesis of triophamine. Tetrahedron Lett. 1997, 38, 6327-6330.