Isolation and Structures of Axistatins 1–3 from the Republic of Palau Marine Sponge Agelas axifera Hentschel

Abstract

An investigation begun in 1979 directed at the Republic of Palau marine sponge Agelas axifera Hentschel for cancer cell growth inhibitory constituents subsequently led to the isolation of three new pyrimidine diterpenes designated axistatins 1 (1), 2 (2), and 3 (3), together with the previously reported formamides 4, 5 and agelasine F (6). The structures were elucidated by analysis of 2D-NMR spectra and by HRMS. All of the isolated compounds were found to be moderate inhibitors of cancer cell growth. Axistatins 1–3 (1–3), formamide 4, and agelasine F (6) also exhibited antimicrobial activity.

New diterpene alkaloids from the marine sponge Agelas mauritiana

“…Compound 1 was isolated as a pale yellow amorphous powder, and its molecular formula was deduced to be C 26 The relative conguration of 1 was deduced from NOESY spectroscopic data (Fig. 3) 27 ) suggested the absolute cong-uration of 1 was probably identical to agelasine B since they had the same relative stereochemistry and the same sign of specic rotation.…”

“…Compound 5, a pale yellow amorphous powder, had a molecular formula of C 26 NMR data (Tables 1 and 2) with those of compound 1. The rest 9, 10-seco-labdane skeleton was determined by analysis of 2D NMR data (Fig.…”

“…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.…”

Clerodane diterpenes: sources, structures, and biological activities

“…, 986 ) were isolated. 364 Other compounds from Agelas species possess both a 9 N -methyladenine moiety at C-15 as well as a 2-carboxy-4-bromopyrrole linked through an ester at C-18 ( e.g. , 990 ), whereas compound 991 with a C4/C18 exocyclic methylene has only the former moiety.…”

Anticancer agents from marine sponges

“…from marine sponge Agelas axifera Hentschel in the Republic of Palau. All of the isolated compounds were found to be significant inhibitors of P338 (murine lymphocytic leukemia), BXPC-3 (pancreatic adenocarcinoma), MCF-7 (breast adenocarcinoma), SF-268 (CNS glioblastoma), NCI-H460 (large-cell lung carcinoma), KML20L2 (colon adenocarcinoma), and DU-145 (prostate carcinoma) cell lines growth[28].Three new merosesquiterpenoids, metachromins U -W (50 -52)(Figure 22), were isolated from the marine sponge Thorecta reticulata collected from Hunter Island, Tasmania, Australia. The cytotoxiStructures of scalarane sesterterpenes(43 -45).…”