Three new iodinated tryptophan derivatives, plakohypaphorines D-F (4-6), have been isolated from the Caribbean sponge Plakortis simplex. Their structures have been determined by application of spectroscopic methods and microwave-assisted selective dehalogenation. Compound 5 is the first naturally occurrung triiodinated indole, while compound 6 is a unique metabolite in possessing both chlorine and iodine atoms on the indole nucleus. Anti-histamine activity for the whole series of plakohypaphorines A-F has been evaluated and only the diiodinated analogues proved to be active, showing a specific antagonism of the non-competitive type.
Iodinated indole alkaloids from Plakortis simplex - New plakohypaphorines and an evaluation of their antihistamine activity / Borrelli, Francesca; Campagnuolo, C.; Capasso, Raffaele; Fattorusso, Ernesto; TAGLIALATELA SCAFATI, Orazio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2004), pp. 3227-3232. [10.1002/ejoc.200400181]
Iodinated indole alkaloids from Plakortis simplex - New plakohypaphorines and an evaluation of their antihistamine activity.
BORRELLI, FRANCESCA;CAPASSO, RAFFAELE;FATTORUSSO, ERNESTO;TAGLIALATELA SCAFATI, ORAZIO
2004
Abstract
Three new iodinated tryptophan derivatives, plakohypaphorines D-F (4-6), have been isolated from the Caribbean sponge Plakortis simplex. Their structures have been determined by application of spectroscopic methods and microwave-assisted selective dehalogenation. Compound 5 is the first naturally occurrung triiodinated indole, while compound 6 is a unique metabolite in possessing both chlorine and iodine atoms on the indole nucleus. Anti-histamine activity for the whole series of plakohypaphorines A-F has been evaluated and only the diiodinated analogues proved to be active, showing a specific antagonism of the non-competitive type.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.