Les alcools aliphatiques sulfatés: nouveaux lipides polaires isolés de diverses fucacées

Liem, Pham Quang; Laur, Marie-Hélène

doi:10.1016/s0300-9084(77)80022-9

Cited by 9 publications

(3 citation statements)

References 18 publications

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“…Naturally occurring alkyl sulfates include methyl, ethyl, and propyl sulfate in avian eggs (9) and the long chain alkyl sulfates that have been found in membrane structures from unicellular algae (10) and seaweed (11). In aerobic soils, 40 -50% of the total sulfur is present as sulfate esters bound to the soil organic matter (12,13), although the molecular structure of these compounds has not yet been determined in detail.…”

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confidence: 99%

Characterization of a Sulfur-regulated Oxygenative Alkylsulfatase from Pseudomonas putida S-313

Kahnert

Kertesz

2000

Journal of Biological Chemistry

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The atsK gene of Pseudomonas putida S-313 was required for growth with alkyl sulfate esters as sulfur source. The AtsK protein was overexpressed in Escherichia coli and purified to homogeneity. Sequence analysis revealed that AtsK was closely related to E. coli taurine dioxygenase (38% amino acid identity). The AtsK protein catalyzed the ␣-ketoglutarate-dependent cleavage of a range of alkyl sulfate esters, with chain lengths ranging from C 4 to C 12 , required oxygen and Fe 2؉ for activity and released succinate, sulfate, and the corresponding aldehyde as products. Enzyme activity was optimal at pH 7 and was strongly stimulated by ascorbate. Unlike most other characterized ␣-ketoglutaratedependent dioxygenases, AtsK accepted a range of ␣-keto acids as co-substrates, including ␣-ketoglutarate (K m 140 M), ␣-ketoadipate, ␣-ketovalerate, and ␣-ketooctanoate. The measured K m values for hexyl sulfate and SDS were 40 and 34 M, respectively. The apparent M r of the purified enzyme of 121,000 was consistent with a homotetrameric structure, which is unusual for this enzyme superfamily, members of which are usually monomeric or dimeric. The properties and amino acid sequence of the AtsK enzyme thus define it as an unusual oxygenolytic alkylsulfatase and a novel member of the ␣-ketoglutarate-dependent dioxygenase family.Bacterial enzymes that cleave aliphatic sulfate esters to release the sulfate moiety have been the subject of considerable study, motivated originally by an awareness of the large scale release of synthetic alkyl sulfate esters into the environment. Due to their amphiphilic properties, long chain aliphatic sulfate esters such as sodium dodecyl sulfate (SDS) are in common use as components of surfactant formulations and are consequently discharged into wastewater. A range of bacterial strains able to degrade aliphatic sulfate esters has been isolated from contaminated sources such as sewage sludge on the basis of their ability to utilize aliphatic sulfate esters as carbon sources for growth (for a review, see Ref. 1). In most cases, degradation of alkyl sulfate esters was found to be initiated by alkylsulfatase enzymes that catalyze the hydrolytic cleavage of the ester bond to liberate inorganic sulfate. The resulting parent alcohol is further degraded (1) or incorporated into cellular lipids (2). Cleavage of the sulfate moiety has been studied in some detail, and several alkylsulfatase enzymes have been purified from cell extracts (3-7).The finding that many isolates from environmental sites that had not been contaminated by detergents also exhibit alkylsulfatase activity (8) suggests that such enzymes may play a role in natural environments as well. Naturally occurring alkyl sulfates include methyl, ethyl, and propyl sulfate in avian eggs (9) and the long chain alkyl sulfates that have been found in membrane structures from unicellular algae (10) and seaweed (11). In aerobic soils, 40 -50% of the total sulfur is present as sulfate esters bound to the soil organic matter (12, 13), although the molecular s...

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confidence: 99%

Characterization of a Sulfur-regulated Oxygenative Alkylsulfatase from Pseudomonas putida S-313

Kahnert

Kertesz

2000

Journal of Biological Chemistry

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“…In detailed studies on 0. danica by Haines and his colleagues (for review, see Haines, 1971), several different chlorinated and non-chlorinated disulphate esters (containing sulphated primary and secondary alcohol groups) have been characterized. Similarly a number of different disulphated longchain alcohols (containing both primary and secondary alkyl sulphate ester groups) have shown to be present (Liem & Laur, 1976) in a variety of brown seaweeds (Fucacae species). Sulphoconjugation of primary alcohols by mammals can also occur, both in vivo (Bostr6m & Vestermark, 1960) and in vitro (Spencer, 1960), and a similar conjugation mechanism has been recognized in the toad (Xenopus laevis) that is not identical with that involved in the formation of bile alcohol sulphates (Scully et al, 1970;Scully, 1971).…”

Section: Discussionmentioning

confidence: 99%

Specificity of P2 primary alkylsulphohydrolase induction in the detergent-degrading bacterium Pseudomonas C12B. Effects of alkanesulphonates, alkyl sulphates and other related compounds

Cloves¹,

Dodgson²,

White³

et al. 1980

Biochemical Journal

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Primary alkanesulphonates were shown to serve as non-metabolizable (gratuitous) inducers of the P2 primary alkylsulphohydrolase enzyme in resting cell suspensions of Pseudomonas C12B. The effects of increasing concentrations of inducer on the production of enzyme were complex and suggestive of a multiphasic phenomenon. However, it was possible to determine Kinducer constants (analogous to Km or Ki) for alkanesulphonates of chain length from C7 to c12. these decreased with increasing chain length in a manner characteristic of an homologous series. Primary alkyl sulphates also served as good inducers of alkylsulphohydrolase, but valid kinetic values could not be obtained because these esters are good substrates for the enzyme and are therefore appreciably hydrolysed during the induction period. Small amounts of enzyme were also produced when cyprinol sulphate, dodecyltriethoxy sulphate C12H23-[O-CH2-CH2]3-O-SO3-Na+), Crag herbicide and some secondary alkyl sulphates were tested as inducers.

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“…Apresentam também, atividades farmacológicas 38,39 e são as mais estudadas substâncias sulfatadas de algas 31,32,40 . São conhecidos poucos metabólitos secundários sulfatados de algas que pertençam a outras classes químicas: apenas raros glicerídeos 41 , ribosídeos 42,43,44 , lipídeos 45 e esteróides 46 , além de um expressivo grupo de fenóis. Esses fenóis sulfatados são encontrados nas rodófitas e feófitas.…”

Section: Substâncias Sulfatadasunclassified

Fenóis halogenados e/ou sulfatados de macroalgas marinhas

Carvalho

Roque

2000

Quím. Nova

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Recebido em 8/10/99; aceito em 18/4/00 HALOGENATED AND/OR SULFATED PHENOLS FROM MARINE MACROALGAE. During the biological evolution, marine macroalgae have developed biochemicals tools in order to utilize components of seawater such as sulfates and halogens, to produce a variety of chemicals (secondary metabolites).This review shows and discuss the occurrence of sulfated and/or halogenated phenolic compounds in seaweeds.Keywords: seaweed; halogenated phenols; sulfated phenols. REVISÃO INTRODUÇÃOO oceano é resultado de uma gigantesca reação ácido -base, onde os ácidos que continuamente afloram do interior da terra são misturados com bases que estão sendo liberadas constantemente das rochas, pela ação do tempo. Suas águas são comparadas a um meio de cultura de composição praticamente constante, o que é verdadeiro para a quase totalidade de seus parâmetros, como por exemplo a porcentagem dos sais dissolvidos, que mantem-se em torno de 3,5%. Este equilíbrio é sustentado por uma série de reações químicas e de processos físico-químicos 1,2 . A vida teve origem nos oceanos. Nesse imenso laboratório, os organismos aquáticos e o ambiente abiótico estão interrelacionados e interagem entre si. Por isso, organismos marinhos adaptaram-se às altas concentrações de sais do meio e desenvolveram mecanismos para utilizar os solutos disponíveis 3,4,5 . Dentre os mais importantes íons presentes no ambiente marinho estão o sulfato, o cloreto, o brometo e o iodeto, em concentrações de 885, 19000, 65, e 0,06 mg.L -1 , respectivamente 1,2 . Portanto, não é de surpreender que os organismos marinhos produzam substâncias halogenadas e sulfatadas em abundância, com maior ou menor eficiência.De todos os organismos marinhos produtores dessas substâncias, sobressaem as algas vermelhas (Rhodophyta), capazes de sintetizar metabólitos halogenados da mais fascinante diversidade, que podem pertencer a praticamente todas as classes químicas, desde hidrocarbonetos de baixo peso molecular, cetonas simples, fenóis, acetogeninas até sofisticados terpenos 3 . Além disso, são eficientes na produção de polissacarídeos sulfatados, os carragenanos e o ágar, que chegam a representar mais de 70 % do seu peso seco e que têm razoá-vel valor comercial 6,7,8,9 . As algas marinhas pardas (Phaeophyta) e verdes (Chlorophyta) são menos eficientes na produção de substâncias halogenadas, sendo que ambas, e particularmente as pardas, apresentam polissacarídeos sulfatados 7,8 . As macroalgas marinhas pertencem ao grupo não homogêneo de organismos denominado "Algae", que se encontra subdividido entre os Reinos Monera e Protista. Esses organismos são fotossintetizantes, não vasculares, contêm clorofila a e apresentam estruturas reprodutivas simples, isto é, sem a proteção de células esteréis 8,10,11 .Enquadram-se nesse conceito desde corpús-culos unicelulares microscópicos até os gigantescos "kelps", algas pardas (Phaeophyta) gigantescas que podem alcançar 60m de comprimento. Tal variedade de organismos encontra-se distribuída por diferentes "habitats": oceanos, corpos de á...

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Les alcools aliphatiques sulfatés: nouveaux lipides polaires isolés de diverses fucacées

Cited by 9 publications

References 18 publications

Characterization of a Sulfur-regulated Oxygenative Alkylsulfatase from Pseudomonas putida S-313

Characterization of a Sulfur-regulated Oxygenative Alkylsulfatase from Pseudomonas putida S-313

Specificity of P2 primary alkylsulphohydrolase induction in the detergent-degrading bacterium Pseudomonas C12B. Effects of alkanesulphonates, alkyl sulphates and other related compounds

Fenóis halogenados e/ou sulfatados de macroalgas marinhas

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