Qualitative variation of alkaloids in color morphs of Cystodytes (Ascidiacea)

López‐Legentil, Susanna; Dieckmann, Ralf; Bontemps-Subielos, Nataly; Turon, Xavier; Banaigs, Bernard

doi:10.1016/j.bse.2005.03.011

Cited by 39 publications

(38 citation statements)

References 58 publications

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“…Meridianins are present both in inner and outer tissues, even if they seem to be more concentrated in outer zones [13]. Apart from these two species, a seeming lack of within-specimen defense allocation was detected in S. adareanum (O) 2, as has also been observed in other ascidians [38]. Rossinone B was proven to take part in the whole-colony chemical defense of A. fuegiense , repelling both sea stars and amphipods, but it was predominant in internal regions.…”

Section: Discussionmentioning

confidence: 92%

Natural Products from Antarctic Colonial Ascidians of the Genera Aplidium and Synoicum: Variability and Defensive Role

et al. 2012

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Ascidians have developed multiple defensive strategies mostly related to physical, nutritional or chemical properties of the tunic. One of such is chemical defense based on secondary metabolites. We analyzed a series of colonial Antarctic ascidians from deep-water collections belonging to the genera Aplidium and Synoicum to evaluate the incidence of organic deterrents and their variability. The ether fractions from 15 samples including specimens of the species A. falklandicum, A. fuegiense, A. meridianum, A. millari and S. adareanum were subjected to feeding assays towards two relevant sympatric predators: the starfish Odontaster validus, and the amphipod Cheirimedon femoratus. All samples revealed repellency. Nonetheless, some colonies concentrated defensive chemicals in internal body-regions rather than in the tunic. Four ascidian-derived meroterpenoids, rossinones B and the three derivatives 2,3-epoxy-rossinone B, 3-epi-rossinone B, 5,6-epoxy-rossinone B, and the indole alkaloids meridianins A–G, along with other minoritary meridianin compounds were isolated from several samples. Some purified metabolites were tested in feeding assays exhibiting potent unpalatabilities, thus revealing their role in predation avoidance. Ascidian extracts and purified compound-fractions were further assessed in antibacterial tests against a marine Antarctic bacterium. Only the meridianins showed inhibition activity, demonstrating a multifunctional defensive role. According to their occurrence in nature and within our colonial specimens, the possible origin of both types of metabolites is discussed.

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Section: Discussionmentioning

confidence: 92%

Natural Products from Antarctic Colonial Ascidians of the Genera Aplidium and Synoicum: Variability and Defensive Role

et al. 2012

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“…The selective detection of alkaloids by MALDI-TOF has been intensively discussed in the literature [17][18][19][20][21][22][23][24], certainly because alkaloids represent highly active natural and/or synthetic substances. Compounds such codeine and its derivatives are commonly used in medicinal applications, while others like strychnine, emetine, and aconitine exhibit severe toxic effects.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, their precise and accurate identification in crude plant material, medicinal preparations, or dietary supplements is highly demanded and a subject of contemporary research. While some aromatic alkaloids such as ascididemin can be ionized by simple LD [23], most reports mention CHCA and TER as preferred matrices for MALDI experiments [17, 20-22, 24, 25]. Additionally, 7-mercapto-4-methylcoumarin has been described for the detection of arecoline and arecaidine, but no further alkaloids were tested [18].…”

Section: Resultsmentioning

confidence: 99%

Selective detection of alkaloids in MALDI-TOF: the introduction of a novel matrix molecule

et al. 2012

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The current manuscript presents 3-[5'-(methylthio)-2,2'-bithiophen-5-ylthio]propanenitrile (MT3P), as a novel matrix molecule, which facilitates the selective ionization of alkaloids in matrix-assisted laser desorption/ionization mass spectrometry. Exhibiting strong ionizing properties at low levels of laser energy, MT3P was evaluated on 55 compounds belonging to various chemical families. The observed molecular ion yields induced by MT3P were compared with those obtained by commercially available matrices such as 1,8-dihydroxy-9,10-dihydroanthracen-9-one, α-cyano-4-hydroxycinnamic acid, 2,2':5',2"-terthiophene and 2,5-dihydroxybenzoic acid. In conclusion, MT3P displayed excellent ionization properties for 23 out of 25 investigated alkaloids, while showing little to no interaction with compounds from different chemical origin. Further, in comparison to other tested matrices, MT3P generally facilitated better ionization of alkaloids. Eventually, levels of laser energy were adjusted to obtain spectra with significantly reduced matrix noise.

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“…These compounds are ascididemins, 11-hydroxyascididemin, cystodytins A-I, shermilamine B, kuanoniamine D, and sebastianines A and B [20,22,25,28,32,35,[43][44][45], some of which showed antitumor properties [25][26][27][28][29]. However, only ascididemin, 11-hydroxyascididemin and sebastianines A and B have been detected in the blue colonies [20,21,29].…”

Section: T98gmentioning

confidence: 99%

“…In addition, the tunic contains calcium carbonate spicules that protect the zooids of the colony and accumulate different cytotoxic compounds: mainly pyridoacridine alkaloids [20,22], as well as diterpenes [23], sphingosines and ceramides [24]; some of which have antileukemic properties [25][26][27][28][29]. These cytotoxicity and acidity mechanisms of the tunic of C. dellechiajei are defence strategies to deter predators and competitors [21,[30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity of the Ascidian Cystodytes dellechiajei Against Tumor Cells and Study of the Involvement of Associated Microbiota in the Production of Cytotoxic Compounds

Martínez‐García

2007

Mar. Drugs

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Many cytotoxic compounds of therapeutic interest have been isolated from marine invertebrates, and some of them have been reported to be of microbial origin. Pyridoacridine alkaloids are the main compounds extracted from the ascidian Cystodytes dellechiajei. Here we describe the in vitro antiproliferative activity against different tumor cell lines of the ascidian extracts and provide some insights on the role of the microbial community associated with the tunicate in the production of these compounds. C. dellechiajei extracts showed remarkably high antiproliferative activity (IC 50 ≤5 µg/mL) in human lung carcinoma A-549, colon adenocarcinoma H-116, pancreatic adenocarcinoma PSN-1 and breast carcinoma SKBR3 cell lines. Moreover, we found that the maximum activity was located in the tunic tissue of the colony, which harbours a microbial community. In order to ascertain the involvement of this community in the synthesis of the bioactive compounds different approachs that included culture and culture independent methods were carried out. We undertook a screening for antiproliferative activities of the bacterial isolates from the ascidian, as well as a comprative analysis of the cytotoxic activities and the microbial communities from two color morphs of the ascidian, green and blue. In addition, the changes of the antiproliferative activities and the composition of the microbial communities were studied from ascidians kept in aquaria and treated with antibiotics for one month. Our

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Qualitative variation of alkaloids in color morphs of Cystodytes (Ascidiacea)

Cited by 39 publications

References 58 publications

Natural Products from Antarctic Colonial Ascidians of the Genera Aplidium and Synoicum: Variability and Defensive Role

Natural Products from Antarctic Colonial Ascidians of the Genera Aplidium and Synoicum: Variability and Defensive Role

Selective detection of alkaloids in MALDI-TOF: the introduction of a novel matrix molecule

Cytotoxicity of the Ascidian Cystodytes dellechiajei Against Tumor Cells and Study of the Involvement of Associated Microbiota in the Production of Cytotoxic Compounds

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