Membrane-structuring properties of bacterial long-chain alkylresorcinols

The occurrence of various amounts of 5-n-alkylresorcinols was shown in lipids extracted from 14 bacterial strains of Azotobacter chroococcum as well as from strains of Pseudomonas aureofaciens, P. chlororapsis, and P. fluorescens. The amount of alkylresorcinols found varied from 2.3 to 56.2 g/mg (dry weight) of cells in A. chroococcum and from 0.2 to 0.8 g/mg (dry weight) of cells in Pseudomonas spp. Strains of both genera produce saturated homologs with C 13 to C 27 side chains. C 19 , C 21 , and C 23 homologs are predominant in and characteristic for A. chroococum strains, the C 15 homolog is predominant in and characteristic for P. chlororapsis and P. fluorescens, and the C 17 homolog is predominant in and characteristic for P. aureofaciens. The presence of 5-n-(2-ketoalkyl)resorcinols, not previously observed, was demonstrated in lipids isolated from the cells of A. chroococum Az5.Alkylresorcinols-long-chain, odd-numbered homologs of orcinol (1,3-dihydroxy-5-methylbenzene)-were demonstrated initially only in the plant kingdom. First, their occurrence in plants from the families Anacardiaceae (Anacardium occidentale [cashew]) and Ginkgoaceae (Ginkgo biloba) was demonstrated (24). In these plants mostly unsaturated homologs of 5-n-pentadecylresorcinol were found. Later, homologs with longer side chains and their derivatives were demonstrated in various species of Gramineae, including cereals and several other plant families such as Proteaceae, Myrsinaceae, Myristicaceae, Liliaceae, and Leguminosae (1, 24; also, references therein). Reusch and Sadoff (15,16) Further experiments showed that during encystment of A. vinelandii over 70% of lipids were replaced with resorcinolic and other phenolic lipids (19). Alkylresorcinols consisted of half of these phenolic compounds. In contrast to plant sources, the alkyl chains of hitherto identified bacterial alkylresorcinols are exclusively saturated.The biological role of these compounds in bacterial organisms is not known yet. Their increasing level during encystment and alteration of cellular metabolism suggest that they are autoregulatory anabiotic compounds (3, 13).Although occurrence of resorcinolic lipids in single strains of Azotobacter and Pseudomonas spp. was indicated, there were no data concerning the abundance of these compounds in various strains from these genera. In this paper we present data indicating that the occurrence of 5-n-alkylresorcinol homologs of various chain lengths is also a characteristic feature in various Azotobacter and Pseudomonas strains and species. MATERIALS AND METHODS Microorganisms.Azotobacter strains were isolated from the organic layer of arable land collected near Wrocl ͞aw. They were identified by the method of Thompson and Skerman (20) at the Department of Agricultural Microbiology, Agricultural University at Wrocl ͞aw. There were 14 strains of A. chroococcum: Az1, Az4, Az5, Az7, Az6, Az8, Az9, Az10, Az11, Az12, Az13, Az15, Az17, and Az18. Three strains from the genus Pseudomonas were used for the study. P. aureofaciens PGS12...

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“…Their increasing level during encystment and alteration of cellular metabolism suggest that they are autoregulatory anabiotic compounds (3,13).…”

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confidence: 99%

Alkylresorcinols are abundant lipid components in different strains of Azotobacter chroococcum and Pseudomonas spp

1996

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“…Tal es el caso de AR aislados de una bacteria del género Azotobacter los cuales se asocian con los fosfolípidos de las membranas formando complejos poliméricos y oligoméricos, modificando la estabilidad y las propiedades fisicoquímicas de las membranas. Adicionalmente se reporta que inhiben la respiración mitocondrial en presencia de sustratos dependientes del NAD, pero la activan en presencia de succinato como sustrato (Bitkov et al, 1992).…”

Section: Propuestas Reportadas De Mecanismos De Acción De Arunclassified

“…Estos metabolitos han sido encontrados en varios organismos de plantas, hongos, bacterias y esponjas marinas (Barrow y Capon, 1991; Kozubek et al, 1996; Kozubek y Tyman, 1999; Zarnowski et al, 1999;Zarnowski et al, 2000a). Los lípidos resorcinólicos estructuralmente están definidos por una molécula con características anfipáticas debido a que en su estructura tiene una cadena alquil hidrofóbica derivada de la biosíntesis de los ácidos grasos y un anillo resorcinol hidrofílico proveniente de la vía biosintética de los policétidos; tal estructura le confiere numerosas propiedades, asociadas a la conformación de la bicapa lipídica, respiración mitocondrial, bioquímica celular, y estructura de la membrana, afectando las propiedades físico-químicas de microorganismos patógenos, (Kozubek y Tyman, 1999;Zarnowski et al, 2002;Bitkov et al, 1992). Esta característica anfipática le proporciona la capacidad de modular la actividad de las enzimas que interactúan con la membrana, por lo que le facilita la fluidez con o entre los lípidos de la membrana (Kieleczawa et al, 1987).…”

Section: Introductionunclassified

“…Esta característica anfipática le proporciona la capacidad de modular la actividad de las enzimas que interactúan con la membrana, por lo que le facilita la fluidez con o entre los lípidos de la membrana (Kieleczawa et al, 1987). Adicionalmente se ven involucrados en asociaciones con los fosfolípidos para formar complejos oligoméricos y poliméricos, provocando así modificaciones en la estructura y propiedades de la bicapa lipídica, así como la propiedad de suprimir la respiración mitocondrial en presencia de substratos dependientes del dinucleótido de adenina y nicotinamida (NAD) (Bitkov et al, 1992).…”

Section: Introductionunclassified

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Alquilresorcinoles: Compuestos Naturales con Importancia Biológica

Suaza-García

Coy-Barrera

2014

Rev. Fac. Cienc. Básicas

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RESUMENLos alquilresorcinoles (AR) son un grupo de metabolitos secundarios no isoprenoides, pertenecientes a la familia de los fenoles, a los que se les confieren propiedades biológicamente importantes tales como: antifúngica, antibacterial, citotóxica, antitumoral, antioxidante y como biomarcadores. Estos metabolitos han sido encontrados en diferentes organismos tales como: plantas, hongos, metazoos y bacterias; siendo las rizobacterias una fuente importante de AR. En la presente revisión se presentan algunas de las características más importantes de estos metabolitos con un enfoque descriptivo con el propósito de reseñar la importancia biológica de estos compuestos naturales.Palabras clave: Alquilresorcinoles, Lípidos resorcinólicos, fuentes de alquilresorcinoles, identificación de alquilresorcinoles.ABSTRACT Alkylresorcinols (ARs) are a group of non-isoprenoid secondary metabolites, belonging to the family of phenols. They exhibit important biological properties such as antifungical, antibacterial, cytotoxic, antitumor, antioxidant, and as biomarkers. These metabolites have been found in different organisms such as plants, fungi, metazoan, and bacteria; being rhizobacteria an important source of ARs. In this review, we present some of the most important features of these metabolites with a descriptive approach in order to notice about the biological importance of these natural compounds.

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“…31 Thus this type of study can serve as a prototype example in understanding the oscillatory behavior in biological systems. [32][33][34][35] Moreover, it exhibited dynamic behavior in aqueous acid medium over a wide range of concentrations in the BZ reaction systems. The ion analyzer (ELICO LI-126) having pH as well as mV option was calibrated in ORP mode with the standard solutions, using Platinum electrode as the indicator and Calomel (SCE) as the reference electrodes.…”

Section: Introductionmentioning

confidence: 99%

Catalyst, Co-ion and the media effect on the oscillatory behavior of resorcinol in the BZ reaction

Ganaie¹,

Peerzada²

2009

J. Braz. Chem. Soc.

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O estudo diz respeito ao comportamento oscilatório de resorcinol como substrato orgânico na reação de Belousov-Zhabotinsky (BZ) em presença de diferentes íons metálicos como catalisadores no meio aquoso ácido. ). On varying the aqueous acid media, it is observed that protonated species with respect to organic substrate (resorcinol) is more easily formed in aqueous sulfuric acid, owing to which maximum number of oscillations are observed in this medium. Moreover, the effect of different anions like acetate, carbonate and sulfate associated with the same metal ion (Mn 2+ ) as catalyst on the oscillatory behavior of the reaction system was also studied. Mixed mode oscillations are seen while changing concentration of aqueous sulfuric acid medium.

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Membrane-structuring properties of bacterial long-chain alkylresorcinols

Cited by 22 publications

References 14 publications

Alkylresorcinols are abundant lipid components in different strains of Azotobacter chroococcum and Pseudomonas spp

Alkylresorcinols are abundant lipid components in different strains of Azotobacter chroococcum and Pseudomonas spp

Alquilresorcinoles: Compuestos Naturales con Importancia Biológica

Catalyst, Co-ion and the media effect on the oscillatory behavior of resorcinol in the BZ reaction

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