Agelasine: A Novel Quaternary 9-Methyladenine from the Sponge <i>Agelas</i><i>dispar</i>

Cullen, Ernest; Devlin, John P.

doi:10.1139/v75-239

Cited by 31 publications

(22 citation statements)

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“…The IR bands at 3500, 1660, and 1600 cm −1 and UV absorptions at 262 and 225 nm were in agreement with literature values 9a,10 for the 6-amino-5-(formylamino)-4-(methylamino)-1,3-diazine unit. The 1 H NMR spectrum contained signals at δ 7.96 (1H, s) and 8.14 (1H, s), assigned to the formamide and C-2′ protons.…”

Section: Resultssupporting

confidence: 91%

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

et al. 2013

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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.

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Section: Resultssupporting

confidence: 91%

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

et al. 2013

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“…[1] Since some bromo-pyrrole derivatives were isolated from the sponge Agelas oroides in 1971, [2] and the report of agelasine, a quaternary 9-methyladenine derivative of an unidentified diterpene isolated from the sponge Agelas dispar in 1975, [3] many bioactive metabolites of different biogenetic origins have been found in the genus of Agelas. [1] Since some bromo-pyrrole derivatives were isolated from the sponge Agelas oroides in 1971, [2] and the report of agelasine, a quaternary 9-methyladenine derivative of an unidentified diterpene isolated from the sponge Agelas dispar in 1975, [3] many bioactive metabolites of different biogenetic origins have been found in the genus of Agelas.…”

Section: Introductionmentioning

confidence: 99%

“…Marine sponges of the genus Agelas (class Demospongiae, order Agelasida, family Agelasidae) represent rich structure diversities in pyrrole and diterpene alkaloids. [1] Since some bromo-pyrrole derivatives were isolated from the sponge Agelas oroides in 1971, [2] and the report of agelasine, a quaternary 9-methyladenine derivative of an unidentified diterpene isolated from the sponge Agelas dispar in 1975, [3] many bioactive metabolites of different biogenetic origins have been found in the genus of Agelas. [4] There were 20 species of the genus Agelas that have been studied.…”

Section: Introductionmentioning

confidence: 99%

Pyrrole Derivatives and Diterpene Alkaloids from the South China Sea Sponge Agelas nakamurai

Chu

Tang

Qin

et al. 2017

Chemistry & Biodiversity

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Two pairs of new non-brominated racematic pyrrole derivatives, (±)-nakamurine D (1) and (±)-nakamurine E (2), two new diterpene alkaloids, isoagelasine C (16) and isoagelasidine B (21), together with 13 known pyrrole derivatives ((±)-3 - 15), five known diterpene alkaloids (17 - 20, 22) were isolated from the South China Sea sponge Agelas nakamurai. The racemic mixtures, compounds 1 - 4, were resolved into four pairs of enantiomers, (+)-1 and (-)-1, (+)-2 and (-)-2, (+)-3 and (-)-3, and (+)-4 and (-)-4, by chiral HPLC. The structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses, quantum chemical calculations, quantitative measurements of molar rotations, application of van't Hoff's principle of optical superposition, and comparison with the literature data. The NMR and MS data of compound 3 are reported for the first time, as the structure was listed in SciFinder Scholar with no associated reference. These non-brominated pyrrole derivatives were found in this species for the first time. Compound 18 showed valuable cytotoxicities against HL-60, K562, and HCT-116 cell lines with IC values of 12.4, 16.0, and 19.8 μm, respectively. Compounds 16 - 19, 21, and 22 showed potent antifungal activities against Candida albicans with MIC values ranging from 0.59 to 4.69 μg/ml. Compounds 16 - 19 exhibited moderate antibacterial activities against Proteusbacillus vulgaris (MIC values ranging from 9.38 to 18.75 μg/ml).

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“…N o attempts have been made on the complete structure determination of agelasine (1). However, recently the isolation of several quaternary 9-methyladenine derivatives of bicyclic diterpenes, agelasines A-D (2-5) (2), ageline B (6) (3), and also 9-methyladenine derivatives of the monocyclic diterpenes, agelasine E (7) (4) and ageline A (agelasine F)' (8) (3,4), has been reported.…”

Section: Introductionmentioning

confidence: 99%

Biologically active metabolites from Agelas mauritiana

Fathi-Afshar¹,

Allen²

1988

Can. J. Chem.

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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.

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Agelasine: A Novel Quaternary 9-Methyladenine from the Sponge Agelasdispar

Abstract: The isolation of a novel quaternary 9-methyladenine from the sponge Agelasdispar is described. The constitution (1) is assigned on the basis of degradative and spectroscopic data.

Cited by 31 publications

References 0 publications

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

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

Pyrrole Derivatives and Diterpene Alkaloids from the South China Sea Sponge Agelas nakamurai

Biologically active metabolites from Agelas mauritiana

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