Crucigasterins A–E, antimicrobial amino alcohols from the Mediterranean colonial ascidian Pseudodistoma crucigaster

Ciavatta, Maria Letizia; Manzo, Emiliano; Nuzzo, Genoveffa; Villani, Guido; Varcamonti, Mario; Gavagnin, Margherita

doi:10.1016/j.tet.2010.07.056

Cited by 22 publications

(25 citation statements)

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“…As with many sessile invertebrates, colonial ascidians are known to produce secondary metabolites to avoid predation and surface colonization by other organisms [ 36 , 37 , 72 , 73 ]. Members of the genus Pseudodistoma are known to be rich in cytotoxic alkaloids, amino alcohols, tryptophan-related compounds, alkyl amines and nucleosides [ 74 – 81 ]. In particular, P. crucigaster produces amino alcohols with strong antimicrobial activity [ 75 , 81 ].…”

Section: Discussionmentioning

confidence: 99%

“…Members of the genus Pseudodistoma are known to be rich in cytotoxic alkaloids, amino alcohols, tryptophan-related compounds, alkyl amines and nucleosides [ 74 – 81 ]. In particular, P. crucigaster produces amino alcohols with strong antimicrobial activity [ 75 , 81 ]. These compounds were obtained after extraction of the full organism; therefore, it is unknown whether the animal, a microbial symbiont or both are responsible of their synthesis.…”

Section: Discussionmentioning

confidence: 99%

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Feeding cessation alters host morphology and bacterial communities in the ascidian Pseudodistoma crucigaster

2016

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BackgroundAscidians can associate with abundant and diverse consortia of microbial symbionts, yet these communities remain unexamined for the majority of host ascidians and little is known about host-symbiont interactions.MethodsWe coupled electron microscopy and 16S rRNA gene tag pyrosequencing to investigate the bacterial communities associated with the colonial ascidian Pseudodistoma crucigaster, a species endemic to the Mediterranean Sea that has a life cycle with two phases: actively-filtering (active) and non-filtering (resting) forms.ResultsResting colonies exhibited a reduced branchial sac (feeding apparatus) and a thickened cuticle. Electron microscope images also suggested higher abundance of colonizing microorganisms on surfaces of resting colonies. Accordingly, bacterial sequences associated with environmental sources (sediment and biofilms, >99 % similarity) were detected exclusively in resting colonies. Bacterial communities of P. crucigaster colonies (active and resting) were dominated by 3 core taxa affiliated (>94 % similarity) with previously described symbiotic Alphaproteobacteria in marine invertebrates. Shifts in rare bacteria were detected when ascidians entered the resting phase, including the appearance of strictly anaerobic lineages and nitrifying bacterial guilds.ConclusionsThese findings suggest that physical (thickened cuticle) and metabolic (feeding cessation) changes in host ascidians have cascading effects on associated bacteria, where modified oxygen concentrations and chemical substrates for microbial metabolism may create anaerobic microhabitats and promote colonization by environmental microorganisms.Electronic supplementary materialThe online version of this article (doi:10.1186/s12983-016-0134-4) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Feeding cessation alters host morphology and bacterial communities in the ascidian Pseudodistoma crucigaster

2016

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“…The acyclic highly unsaturated crucigasterins 9-12 and obscuraminol A 13 ( Fig. 2) are assumed to be biosynthetically derived from L-or D-alanine and the corresponding unsaturated fatty acids via a pathway similar to that of sphingosine biosynthesis [10][11][12]. It is reasonable to assume that these linear compounds as well as other as yet unisolated and unknown aminoalcohol lipids are engaged in the biosynthetic machinery that produces a set of diverse cyclic C-18 amino alcohols: the tetrahydroindane based amaminols A and B, the decahydroquinoline based lepadins 1-8, the quinolizidine based pictamine (17), and the piperidine based, plant derived prosafrinine (18) [13][14][15].…”

Section: Biosynthetic Considerationsmentioning

confidence: 99%

Stereocontrolled construction of decahydro quinoline ring systems: the case of lepadin alkaloids (Review)

Pelšs

Koskinen

2013

Chem Heterocycl Comp

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In this review the marine derived decahydroquinoline alkaloid chemistry and biology is described. A proposal is made for the biosynthetic relationships between acyclic and cyclic C-18 amino alcohol natural products.Keywords: amino alcohols, decahydroquinolines, asymmetric synthesis, biosynthesis, total synthesis. Decahydroquinoline (DHQ) alkaloids are unique natural products that can be divided into three distinct sets. The first group (more than 50 members) of these alkaloids are simple 2,5-disubstituted DHQs isolated from dart poison frogs and ants with the parent member being alkaloid cis-195A, also known as pumiliotoxin C [1]. These diverse cis-or trans-fused decahydroquinolines are equipped with various short alkyl and alkenyl side chains. The structurally related but biologically different lepadins 1-8 (Fig. 1) are on the other hand marine alkaloids isolated from three distinct ascidians: Clavelina lepadiformis (found in the North Sea), Didemnum, and Aplidium tabascum (both found in the Great Barrier Reef) [2][3][4][5]. The third group consists of more complex polycyclic alkaloids that besides the DHQ ring system, can contain several other heterocyclic ring systems fused into one molecule. Representative members of this group are gephyrotoxin and Lycopodium alkaloids [6,7]. This review will focus solely on the second group of DHQ alkaloids which, as distinct from the other two groups of DHQ-containing alkaloids, have not been reviewed in full so far [8]. Lepadin alkaloids differ from dendrobatin frog alkaloids in additional oxygenation at position 3, where the substituent may be a hydroxy or acyloxy group, as well as having eight-carbon long side chains of variable oxidation level at position 5 of the DHQ ring. There are three stereochemical groups of lepadins, each derived from distinct tunicate species (Fig. 1). Lepadin F is an exception, being present in both ascidians from the Great Barrier Reef. Lepadins possess some interesting biological activities: lepadins A and B -cytotoxicity against cancer cell lines, lepadins D-F -antiplasmodal and antitrypanosomal activity. Lately, lepadin B together with pictamine was found to block neuronal nicotinic acetylcholine receptors α4β2 and α7. However, the availability of only small quantities of these natural products has precluded further studies on the development into potential leads for nicotinic based therapies [9].

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“…12), foram isolados da ascídia do Mediterrâneo Pseudodistoma crucigaster. Em particular, a crucigasterina B se mostrou ativa frente a Escherichia coli e Candida albicans a 50 µg/mL, enquanto a crucigasterina E foi ativa frente a E. coli a 100 µg/mL (Ciavatta et al, 2010). Estudos químicos realizados com ascídias levaram ao isolamento de um menor número de compostos, quando comparado com as esponjas marinhas, por exemplo.…”

Section: Figura 10: Fotos Das Ascídias Ascidia Mentulaunclassified

“…13) (Yondelis®) que se encontra atualmente em uso médico no tratamento de sarcomas, enquanto outros, como a didemnina B (43) e aplidina (44) ( Fig. 13), encontram-se na Fase II de testes pré-clínicos (Molinski et al, 2009;Ciavatta et al, 2010).…”

Section: Figura 10: Fotos Das Ascídias Ascidia Mentulaunclassified

Metabólitos secundários bioativos e mediadores de relação predador/presa de invertebrados marinhos

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Crucigasterins A–E, antimicrobial amino alcohols from the Mediterranean colonial ascidian Pseudodistoma crucigaster

Cited by 22 publications

References 29 publications

Feeding cessation alters host morphology and bacterial communities in the ascidian Pseudodistoma crucigaster

Feeding cessation alters host morphology and bacterial communities in the ascidian Pseudodistoma crucigaster

Stereocontrolled construction of decahydro quinoline ring systems: the case of lepadin alkaloids (Review)

Metabólitos secundários bioativos e mediadores de relação predador/presa de invertebrados marinhos

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