Biologically active metabolites from Agelas mauritiana

Abstract

Two novel bicyclic diterpenoides, agelasimine-A (9), and agelasimine-B (10), have been isolated from the orange sponge Agelas mauritiana. Also, a new bromine-containing alkaloid, 5-debromomidpacamide (12), along with midpacamide (13) and methyl N-methyl-4,5-dibromopyrrole-2-carboxylate (11), has been isolated. The structures were determined by interpretation of their spectral data. Agelasimine-A and -B exhibit a wide range of interesting biological activities such as cytotoxicity, inhibition of adenosine transfer into rabbit erythrocytes, Ca2+-channel antagonistic action, and α1 adrenergic blockade.

Dibromopyrrole Alkaloids from the Marine Sponge Acanthostylotella sp

“…The 13 C NMR spectrum showed 6 signals representing one methoxy group and five sp 2 carbons including one methine group and four fully substituted carbons. 1 H and 13 C NMR data of 5 (Table 2) were similar to those of the known related compounds methyl 4,5-dibromo-1H-pyrrole-2carboxylate (5A) [12,16], and methyl N-methyl-4,5dibromopyrrole-2-carboxylate [19]. The structure of 5 was further confirmed by interpretation of 1 H-1 H COSY, and HMBC spectra.…”

New diterpene alkaloids from the marine sponge Agelas mauritiana

“…in 1983, an array of terpenoid alkaloids have been reported to date. 10 These terpenoid derivatives are listed as agelasidines, [10][11][12][13][14][15] agelines, 16 agelasines, 5,15,[17][18][19][20][21][22][23][24] agelasimines, 25 gelasines, 18 and axistatins, 26 which show interesting biological effects, such as cyctotoxic, 14,18,25,26 anti-malarial, 23 anti-microbial, [11][12][13][14]16,22,24,26 antifouling, 19 antifungal, 15 as well as inhibitory effects on Na + /K + -ATPase. 11,17,20 Our previous chemical investigation of the sponge Agelas mauritiana led to the isolation of four new antimicrobial alkaloids, in which (À)-8 0 -oxo-agelasine D was the rst and the only 8 0 -oxo-agelasine reported to date.…”

Synthesis, Antimicrobial and Antineoplastic Activities for Agelasine and Agelasimine Analogs with a β‐Cyclocitral Derived Substituent

“…Agelasines [1 -7] and agelasimines [8,9] are antimicrobial and cytotoxic purine derivatives isolated from marine sponges (Agelas sp.). In both classes of compounds, there is a diterpenoid substituent in the purine 7-position.…”