Agelasine G, a New Antileukemic Alkaloid from the Okinawan Marine Sponge Agelas sp.

Ishida, Keisuke; Ishibashi, Masami; Shigemori, Hideyuki; Sasaki, Takuma; Kobayashi, Jun’ichi

doi:10.1248/cpb.40.766

Cited by 61 publications

(45 citation statements)

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“…Ageline B and agelasine G have the general agelasine structure with a pyrrole hererocycle at diterpene moiety [37]. …”

Section: Alkylpurine Structuresmentioning

confidence: 99%

“…Agelasine G was isolated from Agelas sp. collected off Konbu, Okinawa [37]. Epi -agelasine C was isolated from Agelas mauritiana [64].…”

Section: Sources Of Agelasines Asmarines and Related Compoundsmentioning

confidence: 99%

“…Such compounds have attracted the attention of researchers because of their potent biological activities, which have been reported to include antimicrobial [34,35], antiproliferative [36], antileukemic [37], cytotoxic [34,38], antiprotozoal [39,40] and antituberculosis properties [41] and inhibitory effects on the enzymatic reactions of Na + ,K + -ATPase [42]. Another reason that led to the evaluation of genera of sponges is that a significant number of sponge metabolites show promising activities in antifouling assays [43].…”

Section: Introductionmentioning

confidence: 99%

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Terpenyl-Purines from the Sea

Gordaliza

2009

Marine Drugs

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Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity against a variety of species, including Mycobacterium tuberculosis, and also an important cytotoxic activity against several cancer cell lines, including multidrug-resistant ones. Of particular interest in this context are the asmarines (tetrahydro[1,4]diazepino[1,2,3-g,h]purines), which have shown potent antiproliferative activity against several types of human cancer cell lines. This review summarizes the sources of isolation, chemistry and bioactivity of marine alkylpurines and their bioactive derivatives.

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“…Ageline B and agelasine G have the general agelasine structure with a pyrrole hererocycle at diterpene moiety [37]. …”

Section: Alkylpurine Structuresmentioning

confidence: 99%

“…Agelasine G was isolated from Agelas sp. collected off Konbu, Okinawa [37]. Epi -agelasine C was isolated from Agelas mauritiana [64].…”

Section: Sources Of Agelasines Asmarines and Related Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Terpenyl-Purines from the Sea

Gordaliza

2009

Marine Drugs

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“…We describe here the isolation and structure Considerable research effort is currently being focused on determination of these two novel alkaloids as well as their sigdiscovery of new marine animal antineoplastic and (or) cytonificant cancer cell growth inhibitory activity. toxic constituents based on nitrogen, oxygen, and (or) sulfur heterocyclic systems (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Among the nitrogen heterocyclic compounds, dolastatins 10 (16) (1) and 15 (17) (2), ecteinascidin 729 (9) (3), and cephalostatin 1 (4) (18) are especially noteworthy.…”

Section: Introductionmentioning

confidence: 99%

Antineoplastic agents 285. Isolation and structures of cephalostatins 14 and 15

Pettit

Ichihara

et al. 1994

Can. J. Chem.

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,2260 (1994).The tube-inhabiting marine worm, Cephalodiscus gilchristi has been found to produce a series of cytotoxic and antineoplastic disteroidal alkaloids. A substantial study concerned with discovery of new cell growth inhibitory constituents of this marine animal has led to isolation of cephalostatins 14 (50) and 15 (5b). The structures were determined by interpretation of spectral data, principally high-field (400 and 500 MHz) NMR and HRFABMS combined with NMR spectral relationships to cephalostatin 1 (4) where the structure was previously assigned by X-ray crystal structure analysis. The stereochemical assignments were established employing the ROESY NMR technique. Both new cephalostatins significantly inhibited growth of the P388 lymphocytic leukemia and a selection of human cancer cell lines. The two new cephalostatins further enhance knowledge of structure-activity parameters for these potentially important steroidal alkaloids. On a trouvC que le ver marin habitant un tube, Cephalodiscus gilchristi, produit une sCrie d'alcaloi'des distCroi'daux cytotoxiques et antinCoplastiques. Une Ctude importante relative B la dCcouverte de nouveaux constituants de cet animal marin inhibants la croissance de nouvelles cellules a conduit B I'isolement des cephalostatines 14 (50) et 15 (5b). On a dCtermini le structures par I'interprCtation des donnCes spectrales obtenues principalement par RMN A champ ClevC (400 et 500 MHz) et par HRFABMS combink avec des relations spectrales avec la ctphalostatine 1 (4) dont la structure a Cte attribuCe anterieurernent par diffraction des rayons X. Les attributions stCrkochimiques ont Ct C faites par la technique REOSY de la RMN. Les deux nouvelles cCphalostatines inhibent fortement la croissance de la leuctmie lymphocytaire P388 ainsi qu'une selection de cellules humaines can&reuses. Les deux nouvelles ~Cphalostatines augmentent nos connaissances sur les paramktres structure-activitC de ces alcaloi'des stCroi'daux potentiellement importants.[Traduit par la ridaction]

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“…Agelotoxime D has been isolated from Indonesian Agelas sponges. Agelasimines A and B were isolated from the Solomon Islands orange marine sponge Agelas mauritiana [15,16]. Asmarines A-F were isolated from the marine sponge Raspailia sp.…”

Section: Terpene-purinesmentioning

confidence: 99%