Inhibiting effect of cytotoxic bromine-containing compounds from sponges (Aplysinidae) on Na+-K+-ATPase activity

Gorshkov, Boris A; Горшкова, И. А.; Makarieva, Tatiana N.; Stonik, Valentin A.

doi:10.1016/0041-0101(82)90113-1

Cited by 20 publications

(9 citation statements)

References 5 publications

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“…73,88,89,92 Some derivatives show antimigratory activity against the highly metastatic MDA-MB-231 human breast cancer cell line, 74,75 induce apoptosis in human breast tumor cells, 93 or inhibit Na + -K + -ATPase activity. 94 It can be assumed that some as yet unidentified components, possibly also dibromotyrosine derivatives, are responsible for the antimicrobial activity of the extracts. None of the four extracts of P. arabica investigated in our antimicrobial assay exhibited activity against the yeast Candida albicans.…”

Section: Pseudoceratina Arabicamentioning

confidence: 99%

Isolation and structure elucidation of natural products of three soft corals and a sponge from the coast of Madagascar

et al. 2017

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We investigated the three soft corals Sarcophyton stellatum, Capnella fungiformis and Lobophytum crassum and the sponge Pseudoceratina arabica, which have been collected at the coast of Madagascar. In addition to previously known marine natural products, S. stellatum provided the new (+)-enantiomer of the cembranoid (1E,3E,11E)-7,8-epoxycembra-1,3,11,15-tetraene (2). Capnella fungiformis afforded three new natural products, ethyl 5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-carboxylate (6), ethyl 5-[(1E,5E)-2,6-dimethylocta-1,5,7-trienyl]furan-3-carboxylate (7) and the diepoxyguaiane sesquiterpene oxyfungiformin (9a). The extracts of all three soft corals exhibited moderate activities against the malarial parasite Plasmodium falciparum. Extracts of the sponge Pseudoceratina arabica proved to be very active against a series of Gram-positive and Gram-negative bacteria.

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Section: Pseudoceratina Arabicamentioning

confidence: 99%

Isolation and structure elucidation of natural products of three soft corals and a sponge from the coast of Madagascar

et al. 2017

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“…A wide range of biological activities has been reported for some of these secondary metabolites, including antimicrobial, anti-enzymatic, cytotoxic and antiparasitic activities [11–13]. Previous studies on the sponge V. rigida led to the discovery of antimicrobial and enzymatic activity of its extracts [14,15] and the isolation and structure identification of bromotyrosine-derived compounds [8,16,17]. …”

Section: Introductionmentioning

confidence: 99%

Antiparasitic Bromotyrosine Derivatives from the Marine Sponge Verongula rigida

et al. 2011

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Nine bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Verongula rigida. Two of them, aeroplysinin-1 (1) and dihydroxyaerothionin (2), are known compounds for this species, and the other seven are unknown compounds for this species, namely: 3,5-dibromo-N,N,N-trimethyltyraminium (3), 3,5-dibromo-N,N,N, O-tetramethyltyraminium (4), purealidin R (5), 19-deoxyfistularin 3 (6), purealidin B (7), 11-hydroxyaerothionin (8) and fistularin-3 (9). Structural determination of the isolated compounds was performed using one- and two-dimensional NMR, MS and other spectroscopy data. All isolated compounds were screened for their in vitro activity against three parasitic protozoa: Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compounds 7 and 8 showed selective antiparasitic activity at 10 and 5 μM against Leishmania and Plasmodium parasites, respectively. Cytotoxicity of these compounds on a human promonocytic cell line was also assessed.

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“…These are the only bioassays which have been carried out. It is interesting that 3,5-dibromoverongiaquinol (lb) [2] [17] has been recently shown to possess cytotoxic activity [18].…”

Section: Discussionmentioning

confidence: 99%

Novel, racemic or nearly‐racemic antibacterial bromo‐ and chloroquinols and γ‐lactams of the verongiaquinol and the cavernicolin type from the marine sponge Aplysina (= Verongia) cavernicola

D’Ambrosio

Guerriero

Pietra

1984

Helvetica Chimica Acta

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Butanolic extracts of the Mediterranean sponge Aplysina ( = Verongiu) cavernicola have given, by reverse-phase HPLC, the antibacterial quinols (f)-3-bromoverongiaqui-no1 ( = (+)-3-bromo-I-hydroxy-4-oxo-2,5-cyclohexadiene-l-acetamide; ld) and (+)-3bromo-5-chloroverongiaquino1 ( = (f)-3-bromo-5-chloro-1-hydroxy-4-oxo-2,5-cyclohexadiene-I-acetamide; lc) besides the products of their formal cyclization 5-chlorocavernicolin ( = 5-chloro-3,3a,7,7a/3-tetrahydro-3aP-hydroxy-2,6( 1H)-indoledione; 6), the C(7)-epimerizing 7/3-bromo-5-chlorocavernicolin ( = 7P-bromo-5-chloro-3,3a,7,7aa-tetrahydro-3ap-hydroxy-2,6( 1 H)-indoledione; 4a) and 7cr -bromo-5-chlorocavernicolin (4b), and the C(7)-epimerizing 5-bromo-7~-chlorocavernicolin ( = 5-bromo-7~-chloro-3,3a,7,7a~-tetrahydro-3a~-hydroxy-2,6( 1H)-indoledione; 5a) and 5-bromo-7a -chlorocavernicolin (5b). The latter four were isolated as mixtures of C(7)-epimerizing monoacetates 4a'/4b' and 5a'/5b'. Both Id and l c proved to be racemic from NMR examination of their esterification products with (-)-menthyloxyacetic acid, whilst 6 had a ca. 6% enantiomeric purity as shown by a 'H-NMR study of its monoacetate 6' in the presence of a chiral shift reagent. These chiroptical data of the first chiral quinols from the Verongida and of 6 suggest phenol oxidative routes from tyrosine precursors for their formation. In view of their bioactivities, Id and l c have been synthesized from (p-hydroxypheny1)acetic acid by phenol oxidative routes.1. Introduction. -Marine sponges of the order Verongida are of much current biological [I] and organic-chemical interest [2]. Unusual fatty acids [3], sterols [4], carotenoids [5], and amino acids [6] have been isolated from members of this order. However, what makes these sponges unique organisms is their extraordinary ability to give a vast array of dibrominated metabolites of either proven, in certain cases [7], or likely origin from 3,5-dibromotyrosine. These dibrominated metabolites have been recently reviewed from both the chemical [2] and the chemotaxonomical [8] points of view. To

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Inhibiting effect of cytotoxic bromine-containing compounds from sponges (Aplysinidae) on Na+-K+-ATPase activity

Cited by 20 publications

References 5 publications

Isolation and structure elucidation of natural products of three soft corals and a sponge from the coast of Madagascar

Isolation and structure elucidation of natural products of three soft corals and a sponge from the coast of Madagascar

Antiparasitic Bromotyrosine Derivatives from the Marine Sponge Verongula rigida

Novel, racemic or nearly‐racemic antibacterial bromo‐ and chloroquinols and γ‐lactams of the verongiaquinol and the cavernicolin type from the marine sponge Aplysina (= Verongia) cavernicola

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