Cytotoxic activity of aaptamines from suberitid marine sponges

Федореев, С. А.; Prokof'eva, N. G.; Denisenko, V. A.; Rebachuk, N. M.

doi:10.1007/bf00763625

Cited by 28 publications

(28 citation statements)

References 3 publications

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“…These were aaptamine (1), isoaaptamine (2), and their HCl salts. They were identified by comparison of their spectral properties with the literature [11,12]. Fractionation of the extract from Hyrtios sp.…”

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confidence: 99%

Antioxidant activityofaromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios SP.

Utkina

2009

Chem Nat Compd

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547.94+593.4Aaptamine (1) and isoaaptamine (2) were isolated from the marine sponge Aaptos aaptos; 6-bromo- 2′-de-N-methylaplysinopsin (3) from the marine sponge Hyrtios sp. Alkaloids 1-3 were tested for the ability to trap 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, to reduce Folin-Ciocalteau reagent (FCR), and to inhibit oxidation of linoleic acid (LA) induced by peroxide radicals. Compounds 1 (IC 50 18 μM), 2 (IC 50 16 μM), and 3 (IC 50 18 μM) reacted strongly with DPPH, comparable with trolox (IC 50 16 μM) and showed high reducing ability for FCR. The inhibition of LA oxidation by 1-3 was comparable with that of ionol (BHT). It was shown that the antioxidant activity of 1-3 was related to their ability to release both electrons and H atoms.Research on marine natural compounds, which began about 60 years ago, has shown that almost every class of marine organisms synthesizes a variety of molecules with unique structures that are not observed among natural compounds from terrestrial sources owing to the physical and chemical conditions of the marine environment [1,2]. Marine sponges are one of the most ancient classes of animals. The class Demospongiae contains about 95% of living species and is represented around the world by about 14,000-15,000 species [3]. Marine sponges, from which more than 50% of marine natural compounds have been isolated [2], are a rich source of compounds with cytotoxic and antitumor properties [4,5]. The antioxidant activity of compounds isolated from marine sponges is relatively little studied [6-9]. Avarol from the Mediterrean sponge Disydea avara is the only example of a well studied antioxidant from sponges. It is currently manufactured as a preparation against psoriasis [10].In continuation of the search for antioxidants from marine organisms, we investigated marine sponges Aaptos aaptos (Hadromerida, Suberitidae) and Hyrtios sp. (Dictyoceratida, Thorectidae), the alcohol extracts of which acted as strong traps for 2,2-diphenyl-1-picrylhydrazyl radical (DPPH). Our goal was to isolate the active metabolites from these species of marine sponges and study the antioxidant activity and mechanism of antioxidant activity of the obtained compounds.Fractionation of the extract from A. aaptos isolated compounds that were active traps for DPPH. These were aaptamine (1), isoaaptamine (2), and their HCl salts. They were identified by comparison of their spectral properties with the literature [11,12]. Fractionation of the extract from Hyrtios sp. isolated the active compound 6-bromo-2′-de-N-methylaplysinopsin (3), which was identified by comparison of spectral data with those published [13].

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Antioxidant activityofaromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios SP.

Utkina

2009

Chem Nat Compd

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“…The group of Fedoreev 28 unveiled in 1988 the isolation of 1, together with 3 and isoaaptamine (2) from a Suberites sp. sponge (Hadromerida, Suberitidae, sub-class Tetractinomorpha), collected in the Indian Ocean in 1985.…”

Section: The Isolation Of Aaptamine and Congenersmentioning

confidence: 99%

“…As shown in Scheme 2, the aaptamine skeleton can be assumed to be derived from S-3(3,4-dihydroxyphenyl) alanine (L-DOPA, 27) and a biosynthetic equivalent of b-alanine aldehyde (28), which is the formal Michael addition product of acrolein and ammonia. Both compounds are also precursors in Baldwin's hypothesis for the biosynthesis of manzamine alkaloids.…”

Section: Biosynthetic Considerationsmentioning

confidence: 99%

Aaptamine and related products. Their isolation, chemical syntheses, and biological activity

2009

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“…They are known to have a unique class of alkaloids as major components namely the aaptamines, which bear a unique 1H-benzo [de] [1,6] naphtyridines structure. Aaptamine (1) and isoaaptamine (2), the major metabolites of A. suberitoides, were first reported by Nakamura et al (1987) and Fedoreev et al (1989), respectively. Both compounds have been reported to possess anticancer activities against various cell lines i.e.…”

Section: Introductionmentioning

confidence: 99%

STUDY ON THE EFFECT OF POLLUTANTS ON THE PRODUCTION OF AAPTAMINES AND THE CYTOTOXICITY OF CRUDE EXTRACT FROM Aaptos suberitoides

Dewi

Hadi²,

Januar³

et al. 2013

Squalen Bull. Marine Fisheries Postharvest Biotech.

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This experiment was conducted to study the effects of anthropogenic stressor on the spatial variability of secondary metabolites from marine sponge Aaptos suberitoides. Samplings were conducted at 7 sites in Marine National Park of Thousand Islands that are extended within 30 km off Jakarta bay on late February 2011. Sponges were collected and quantified by means of liquid chromatography coupled with photo-diode array detection, whereas, cytotoxicity of sponges extracts was determined against T47D (breast) cancer cell lines. Results showed that the spatial production of aaptamine and isoaaptamine did not correlate with the quality of their surrounding habitat, despite nitrite and nitrate levels significantly affected the bioactivity of crude extracts.Keywords: A. suberitoides, aaptamines, spatial production, cytotoxicity, pollutants ABSTRAK Penelitian ini dilakukan untuk mempelajari efek tekanan antropogenik terhadap variabilitas spasial metabolit sekunder dari spons laut A. suberitoides. Kegiatan sampling dilakukan di tujuh titik yang berada di area Taman Nasional Kepulauan Seribu yang tersebar sepanjang 30 km dari wilayah Teluk Jakarta pada bulan Februari 2011. Spons dikoleksi dan dikuantifikasi menggunakan kromatografi cair yang dilengkapi deteksi photo-diode array sedangkan sitotoksisitas ekstrak spons diukur terhadap sel kanker T47D (payudara). Hasil penelitian menunjukkan bahwa produksi spasial dari aaptamin dan isoaaptamin tidak berkorelasi dengan kualitas dari habitat disekitarnya, meskipun kadar nitrit dan nitrat mempengaruhi bioaktivitas ekstrak pekat secara signifikan.

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Cytotoxic activity of aaptamines from suberitid marine sponges

Cited by 28 publications

References 3 publications

Antioxidant activityofaromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios SP.

Antioxidant activityofaromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios SP.

Aaptamine and related products. Their isolation, chemical syntheses, and biological activity

STUDY ON THE EFFECT OF POLLUTANTS ON THE PRODUCTION OF AAPTAMINES AND THE CYTOTOXICITY OF CRUDE EXTRACT FROM Aaptos suberitoides

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