Structure, amount and composition of sulfuric, sulfonic and phosphoric esters of glycosyldiglycerides of three fucacea]

The mono and polyester glycosyl sulfates or phosphate diglycerides account for a group of polar lipids which is found in large amounts in the three fucacae that are studied: Pelvetia canaliculata (L) Deen and Thur, Fucus vesiculosus (L), Fucus serratus (L). These polar lipids have been shown to have complex structures, most of them are unknown in the present nomenclature. Both quantity and composition of these polar lipids are species characteristics, forming the equipment of polar lipids for every species of algae. Glycosyl ester sulfate and phosphate diglycerides are very unstable substances when pure, moreover photolabile and thremodegradable. This extreme fragility caused many difficulties in the determination of molecular structures which require a very high purity of isolated substances, The determination of the structures, studies of quantities and composition cytological localization of these polar lipids should allow to define clearly their physiological function and importance from the biochemical and ecological point of view.     

Aliphatic alcohol sulfates: new polar lipids isolated from various Fucacea]

Four new sulfolipids have been found in the three Fucacea from the coast of Britany P. canaliculata (L) Deen et Thur, F. vesiculosus (L), F. serratus (L). These four polar lipids form a separate group, their structures being very different from those of the glyceride by-products already known. By acid hydrolysis of these substances the aliphatic mono and dialcohols can be separated. The aliphatic hydrocarbons studied by gas chromatography and spectrometric methods (IR, MASS), have been established as being saturated C30 mono or dialcohols, saturated C18 and C20 monoinsaturated dialcohols. SAA are the only substances found: there was no sulfonate or phosphate ester in the three algae studied. The quantity and composition of SAA are not characteristic of the species. Their variations depend on the physiological and biochemical states of the thallus and on the conditions of extraction and purification.     

Examination of the structures of several glycerolipids from marine macroalgae by NMR and GC‐MS

Several classes of glycerolipids were isolated from the total lipids of the algae Saccharina cichorioides, Eualaria fistulosa, Fucus evanescens, Sargassum pallidum, Silvetia babingtonii (Ochrophyta, Phaeophyceae), Tichocarpus crinitus, and Neorhodomela larix (Rhodophyta, Florideophyceae). The structures of these lipids were examined by nuclear magnetic resonance (NMR) spectroscopy, including 1D (¹H and ¹³C) and 2D (COSY, HSQC and HMBC) experiments. All of the investigated algae included common galactolipids and sulfonoglycolipids as the major glycolipids. Minor glycolipids isolated from S. cichorioides, T. crinitus, and N. laris were identified as lyso‐galactolipids with a polar group consisted of the galactose. Comparison of the ¹H NMR data of minor nonpolar lipids isolated from the extracts of the brown algae S. pallidum and F. evanescens with the ¹H NMR data of other lipids allowed them to be identified as diacylglycerols. The structures of betaine lipids isolated from brown algae were confirmed by NMR for the first time. The fatty acid compositions of the isolated lipids were determined by gas chromatography‐mass spectrometry.     

<Emphasis Type="Italic">Halorubrum cibi</Emphasis> sp. nov., an extremely halophilic archaeon from salt-fermented seafood

Strain B31^T is a Gram-staining-negative, motile, and extremely halophilic archaeon that was isolated from salt-fermented seafood. Its morphology, physiology, biochemical features, and 16S rRNA gene sequence were determined. Phylogenetic analysis of its 16S rRNA gene sequence and composition of its major polar lipids placed this archaeon in the genus Halorubrum of the family Halobacteriaceae. Strain B31^T showed 97.3, 97.2, and 96.9 % 16S rRNA similarity to the type strains of Halorubrum alkaliphilum, Hrr. tibetense, and Hrr. vacuolatum, respectively. Its major polar lipids were phosphatidylglycerol (PG), phosphatidylglycerol phosphate methyl ester (PGP-Me) and sulfated diglycosyl diether (S-DGD). Genomic DNA from strain B31^T has a 61.7 mol% G+C content. Analysis of 16S rRNA gene sequences, as well as physiological and biochemical tests, identified genotypic and phenotypic differences between strain B31^T and other Halorubrum species. The type strain of the novel species is B31^T (=JCM 15757^T =DSM 19504^T).     

Etude comparee des lipides et de la fixation passive du calcium dans les racines et les fractions subcellulaires du Lupinus luteus et de la Vicia faba

In both lupin and broad bean, the root lipids contain paraffins, triglycerides, diglycerides, free fatty acids and polar lipids (phospholipids and galactolipids). The polar lipids and the triglycerides are the more abundant classes. The root galactolipids are mono- and di-galactosyldiglycerides; two steryl glycosides are also present. The phospholipids in both species are: phosphatidylinositol, phosphatidylcholine, phosphatidylglycerol, phosphatidylserine, phosphatidylethanolamine, diphosphatidylglycerol and phosphatidic acid. This last phospholipid represents 8·3% of total lipid phosphorus in Lupinus against 2·3% in Vicia. The other acidic phospholipids represent 30·4% in Lupinus against 20·9% in Vicia. The lipids of Lupinus are rich in linolenic acid whereas those found in Vicia are richer in linoleic acid. The various subcellular fractions prepared from the roots of both species have an homogeneous lipid composition, reflecting exactly that of entire cells. The calcium passive fixation capacity in microsomes and mitochondria of Lupinus roots is more important than that in the same organelles of Vicia faba roots. Thus a relationship is suggested between the amount of phospholipids in membranes and the passive fixation of calcium.     

Physiological studies on Phymatotrichum omnivorum VI. Lipid composition of mycelium and sclerotia

The lipid composition of the mycelium and sclerotia ofPhymatotrichum omnivorum was compared. The lipids of the mycelium contained 47.9 % polar lipids as compared to 21.4 % in the sclerotia. Sterols represented 10 % of the lipids in sclerotia as contrasted to 3.6 % of the mycelium. More monoglycerides (17.5 %) were detected in the sclerotia as compared to the mycelium (1.6 %). Fatty acid analysis indicated that linoleic acid was the predominant fatty acid in the total fatty acids fraction in both the mycelium and the sclerotia. Palmitic acid was the major free fatty acid in the mycelium, whereas myristic acid was the predominant free fatty acid in the sclerotia. In the fatty acids of the diglycerides of sclerotia, palmitic acid represented 71 % of that fraction, as compared to 6.6 % of the fatty acids of the diglycerides in the mycelium. The major fatty acid in the diglycerides of the mycelium was oleic acid.     

The effect of changing the composition of phosphatidylglycerol from thylakoid polar lipids of oleander and cucumber on the temperature of the transition related to chilling injury

The composition and phase behavior of some lipid classes and mixtures of thylakoid polar lipids were measured to investigate their role as determinants of the temperature of the transition associated with chilling injury. For Nerium oleander L., a plant which acclimates to growth temperature, a mixture of the phosphatidylglycerol (PG) and sulfoquinovosyldiacylglycerol (SQDG) showed transition temperatures of 22° and 10° C for plants grown at 45° and 20° C, respectively. This difference was similar to the 9 Celsius degrees differential in the transition of the polar lipids and indicated that the PG and-or the PG-SQDG mixture could be the major determinants of the transition temperature. Reconstitution of the PG-SQDG mixture from 20°-grown oleander with the galactolipids from 45°-grown plants, however, reduced the transition temperature by only 4 Celsius degrees. This indicates that some, low-melting-point lipids, which are structurally capable of forming a co-gel with the high-melting-point lipids, also play a role in determining the temperature of the transition and that the composition of these low-melting-point lipids also changes with growth temperature. More specific information on the role of PG was obtained using polar lipids from Cucumis sativus L., a chilling-sensitive plant. For this material the transition in the polar lipids was reduced from 9° to 5° and 4° C when the transition of the PG was reduced from 32° to 25° and 22° C. This was accomplished by reducing the proportion of disaturated molecular species in PG from 78 to 56 and 44 mol% by the addition of a fraction of the PG enriched in unsaturated molecular species. The data indicate that the transition temperature of the polar lipids of cucumber would be reduced to below 0° C, typical of a chillinginsensitive plant, when the transition temperature of PG was reduced to 15° C and this would occur at 21 mol% of disaturated molecular species. It is concluded that the transition in the thylakoid polar lipids, associated with chilling injury, involves both high- and low-meltingpoint lipids but can be reduced when the transition temperature of the high-melting-point component is reduced.Abbreviations DGDG digalactosyldiacylglycerol - MGDG monogalactosyldiacylglycerol - PG phosphatidylglycerol - SQDG sulfoquinovosyldiacylglycerol     

The Polyunsaturated Fatty Acids of Marine and Freshwater Cryptomonads1

SYNOPSIS Fatty acids were examined of photosynthetic and non-photosynthetic marine and freshwater cryptomonads cultured as photoauxotrophs, photoheterotrophs and heterotrophs at various incubation temperatures and constant light intensity. Photo-synthetic marine and freshwater forms contained octadecatrienoic, octadecatetraenoic, eicosapentaenoic and docosahexaenoic (all-cis, ω3 acids) as the major polyunsaturates, and a freshwater heterotroph contained mostly the octadecatrienoic acid. The polar lipids of a marine, photosynthetic form, Cryptomonas sp., included the usual thylakoid membrane lipids of the chloroplasts of eukaryotic, photosynthetic cells: galactosyl diglycerides, phosphatidyl glycerol and a sulfolipid. Also present were 2 choline-containing phospholipids: phosphatidyl choline and an unknown. Ninhydrin-positive and inositol-containing lipids were not detected. Octadecatetraenoic acid comprised 75% of the total fatty acids of the monogalactosyl diglyceride fraction. The phosphatidyl glycerol was acylated mostly by ω13 trans-hexadecaenoic acid and the eicosapentaenoic acid. Evolutionary relationships of cryptomonads as mirrored in lipid composition are discussed.     

Occurrence of arsenic species in the seagrass <Emphasis Type="Italic">Posidonia oceanica</Emphasis> and in the marine algae <Emphasis Type="Italic">Lessonia nigrescens</Emphasis> and <Emphasis Type="Italic">Durvillaea antarctica</Emphasis>

The seagrass Posidonia oceanica from the Mediterranean coast and the brown algae Durvillaea antarctica and Lessonia nigrescens from the Chilean coast were analysed for total arsenic and for arsenic species. Arsenic species were extracted with water and measured by high-performance liquid chromatography–inductive coupled plasma mass spectrometry. Arsenite, arsenate, methylarsonate, dimethylarsinate, sulfonate sugar, sulphate sugar and phosphate sugar were analysed with an anion exchange column. Arsenobetaine, arsenocholine and glycerol sugar were separated with a cation exchange column. An extract of Fucus serratus was used to assign the arsenosugar peaks in the chromatograms from the sample extracts. In addition to the four common arsenosugars found in algae, inorganic arsenic was also measured in some samples, with the highest content found in L. nigrescens. The certified reference material (CRM) NIES no. 9 Sargassum fullvellum was analysed for quality assessment of total arsenic, and moreover, arsenosugars were also determined in this CRM.     

Structures of archaebacterial membrane lipids

Structural data on archaebacterial lipids is presented with emphasis on the ether lipids of the methanogens. These ether lipids normally account for 80–95% of the membrane lipids with the remaining 5–20% of neutral squalenes and other isoprenoids. Genus-specific combinations of various lipid core structures found in methanogens include diether-tetraether, diether-hydroxydiether, or diether-macrocyclic diether-tetraether lipid moieties. Some species have only the standard diether core lipid, but none are known with predominantly tetraether lipids as found in certain sulfur-dependent archaebacteria. The relative proportions of these lipid cores are known to vary in relation to growth conditions inMethanococcus jannaschii andMethanobacterium thermoautotrophicum. Polar headgroups in glycosidic or phosphodiester linkage to thesn-1 orsn-1 carbons of glycerol consist of polyols, carbohydrates, and amino compounds. The available structural data indicate a close similarity among the polar lipids synthesized within the species of the same genus. Detection of lipid molecular ions by mass spectrometry of total polar lipid extracts is a promising technique to provide valuable comparative data. Since these lipid structures are stable within the extreme environments that many archaebacteria inhabit, there may be specific applications for their use in biotechnology.     

Fatty-acid composition of polar lipids in fruit and leaf chloroplasts of “16:3”- and “18:3”-plant species

The fatty-acid composition of polar lipids from fruit and leaf chloroplasts was compared in five Solanaceous and two cucurbit species. The acylated fatty acids in monogalactosyl diglycerides (MGDG) from leaf chloroplasts of all five Solanaceous species included substantial amounts of ^7,10,13-hexadecatrienoic acid (16:3). In contrast, the MGDG from fruit chloroplasts of the Solanaceae contained very little of this plastid-specific polyunsaturate, and instead included a proportionately greater percentage of linoleic acid (18:2). In MGDG from leaf chloroplasts of two cucurbits, -linolenic acid (18:3) constituted 94–95% of the acylated fatty acids. Fruit-chloroplast galactolipids of the cucurbits had a greater abundance of 18:2, and hence a higher 18:2/18:3 ratio, than found in the corresponding leaf lipids. Among the phosphoglycerides, the unusual fatty acid 3-trans-hexadecenoate (trans-16:1) constituted from 15 to 24% of the acylated fatty acids in phosphatidyl glycerol (PG) from leaf chloroplasts (all species). In sharp contrast, trans-16:1 was virtually absent in PG from fruit chloroplasts of both Solanaceous and cucurbit species, and was replaced by a proportionate increase in the content of palmitate (16:0). The observed differences in the polar lipid fatty-acid composition of fruit and leaf chloroplasts are discussed in terms of the relative activity of several intrachloroplastic enzymes involved in lipid synthesis and fatty-acyl desaturation.Abbreviations MGDG monogalactosyldiglyceride - DGDG digalactosyl diglyceride - PC phosphatidyl choline - PE phosphatidyl ethanolamine - PG phosphatidyl glycerol     

Fatty acid composition of lipids in the calluses of two pine species <Emphasis Type="Italic">Pinus sibirica</Emphasis> and <Emphasis Type="Italic">Pinus sylvestris</Emphasis>

The fatty acid (FA) composition of callus lipids in two pine species, Pinus sibirica Du Tour and P. sylvestris L. was studied. Callus lipids were characterized by a high content of unsaturated FAs: 81.7% in P. sibirica and 63.2% in P. sylvestris. Among them, oleic and linoleic acids predominated (22.9 and 34.0% of total FAs in P. sibirica and 17.6 and 27.8% in P. sylvestris, respectively). Callus lipids also contained Δ5-UPIFA (unsaturated polymethyle-interrupted FAs), where pinoleic and sciadonic acids predominated. A comparison of FAs in the lipids of P. sylvestris calluses derived from needle and needle photosynthesizing tissues of this pine species showed that callus lipids were characterized by a greater diversity of Δ5-UPIFA but a lower degree of FA unsaturation and he higher level of Δ5-UPIFA.     

Rapid degradation of polar lipids in frost damaged winter wheat crown and root tissue

The ettect of a lethal frost on the lipid composition of crown and root tissue of winter wheat after thawing was investigated. The data show rapid degradation of polar lipids with an increase first in diglycerides and later in unesterified fatty acids, while active synthesis of triglycerides was maintained during the first 6 hr after thawing. Polyunsaturated species of polar lipids were preferentially degraded. Extensive losses of total linoleic and linolenic acids suggest lipoxygenase action. The observed lipid degradation after frost is probably the result of decompartmentation following damage to membranes.     

The lipids of phosphorescent Vibrio albensis bacteria]

The lipid composition of fluorescent vibrios, V. eltor and nonagglutinating vibrios has been studied. In the fraction of polar lipids phosphatidylethanolamine, phosphatidylinositol and cardiolipin and in the fraction of neutral lipids monoglycerides, free fatty acids, diglycerides, triglycerides, sterol esters have been identified. The fatty acid composition of some classes of neutral lipids have been determined. Both similarity and differences between the strains under study in their lipid and fatty acid composition have been established.     

Peculiarities of the corrective effects of polar lipids and bioantioxidants from sea hydrobionts in impairments of lipid and carbohydrate metabolism

A total mixture of phospho- and glycolipids from sea macrophytes Sargassum pallidum, Ulva fenestrata, Zostera marinawas separated and the fatty acid composition was determined. Biological activity of the mixtures of polar lipids and natural antioxidants (echinochrome A from the flat sea urchin Scaphechinus mirabilis and a polyphenolic complex from the sea grass Zostera marina) were studied under conditions of impairments of carbohydrate and lipid metabolism. Doses and compositions of mixtures of polar lipids and antioxidants possessing high corrective activity were optimized in mice with the experimental model of atherosclerosis and diabetes. Based on these results possible mechanisms of the effects of polar lipids containing various polyunsaturated fatty acids and the investigated antioxidants have been proposed. The developed compositions may be used for creation of new biologically active additives and drugs.     

The Effect of Helminthosporic Root Rot on the Composition of Acyl Lipids of Wheat Seedlings

The changes of the molecular species composition of esterified fatty acids (FAs) of total and nonextractable lipids were determined in roots and etiolated shoots of 3- to 10-day-old wheat (Triticum aestivumL.) seedlings infected with the fungus Bipolaris sorokiniana, the agent of helminthosporic root rot. A novel technique of assessing the extent of the infection-induced deviation of FA composition, mol %, from the control value was developed. It consists in the quantitative determination of both the deviations in this composition and the extent of contribution of separate FA species to the deviations observed. The application of this technique has shown that, for the total lipids, the maximum of such a deviation, in accordance with the membrane theory of stress, directly coincided in time with the onset of a decrease in the dry matter content in both roots and shoots. In each of these, the deviation was primarily caused by the change in the content of those FA species that usually dominate in a specific group of membrane lipids prevailing in a given organ, viz., plastid glycolipids in shoots and extraplastidal membrane phospholipids in roots. In both cases, C₂₀–C₂₂FAs significantly contributed to the deviations observed. This fact seems to reflect an enhanced formation of epicuticular waxes rich in these FAs on the shoot and root surfaces as an adaptive response of plants to fungal infection. Nonextractable (annular) membrane lipids, because of their vital importance for the survival of plant cells, differed from the total lipids with a far greater stability of their quantitative FA composition under conditions of infection-induced metabolic disturbances.     

LIPID COMPOSITION OF CHLORARACHNIOPHYTES (CHLORARACHNIOPHYCEAE) FROM THE GENERA BIGELOWIELLA,GYMNOCHLORA, AND LOTHARELLA1

The Chlorarachniophyceae are unicellular eukaryotic algae characterized by an amoeboid morphology that may be the result of secondary endosymbiosis of a green alga by a nonphotosynthetic amoeba or amoeboflagellate. Whereas much is known about the phylogeny of chlorarachniophytes, little is known about their physiology, particularly that of their lipids. In an initial effort to characterize the lipids of this algal class, four organisms from three genera were examined for their fatty acid and sterol composition. Fatty acids from lipid fractions containing chloroplast‐associated glycolipids, storage triglycerides, and cytoplasmic membrane‐associated polar lipids were characterized. Glycolipid‐associated fatty acids were of limited composition, principally eicosapentaenoic acid [20:5(n‐3)] and hexadecanoic acid (16:0). Triglyceride‐associated fatty acids, although minor, were found to be similar in composition. The polar lipid fraction was dominated by lipids that did not contain phosphorus and had a more variable fatty acid composition with 16:0 and docosapentaenoic acid [22:5(n‐3)] dominant along with a number of minor C₁₈ and C₂₀ fatty acids. Crinosterol and one of the epimeric pair poriferasterol/stigmasterol were the sole sterols. Several genes required for synthesis of these sterols were computationally identified in Bigelowiella natans Moestrup. One sterol biosynthesis gene showed the greatest similarity to SMT1 of the green alga, Chlamydomonas reinhardtii. However, homologues to other species, mostly green plant species, were also found. Further, the method used for identification suggested that the sequences were transferred to a genetic compartment other than the likely original location, the nucleomorph nucleus.     

Influence of abiotic factors on the lipid composition of <Emphasis Type="Italic">Ulva intestinalis</Emphasis> (L.) link (Chlorophyta) in small rivers of the El’ton Lake basin of the Caspian lowland

The content and composition of lipids of alga Ulva intestinalis (L.) Link, collected at ten stations located in the small rivers of an arid zone of the Caspian lowland, have been studied. The relations between the content of lipids of U. intestinalis and abiotic factors have been analyzed (mineralization level, temperature rate, saturation by oxygen, and the acidity of the environment). It is established that the level of mineralization of the water is the defining factor affecting the composition of membrane lipids.     

Polar lipids in phototrophic bacteria of the Rhodospirillaceae and Chromatiaceae families.

The polar lipids of photosynthetic purple bacteria of the genera Chromatium, Thiocapsa, Thiocystis, Ectothiorhodospira, Rhodopseudomonas, Rhodospirillum, and Rhodomicrobium were analyzed. Characteristic compositions of the polar lipids were found for most of the Rhodospirillaceae and Chromatiaceae species. Phosphatidylethanolamine, phosphatidylglycerol, and cardiolipin were the major phospholipids in most species. Phosphatidylcholine was present as a major component in all species of the genus Ectothiorhodospira, but was not detected in the remaining Chromatiaceae. It was also present in most of the Rhodospirillaceae species. No glycolipids were found in any of the Ectothiorhodospira species. In the Rhodospirillaceae, the glycolipids mono- and digalactosyl diglycerides were generally absent. Sulfoquinovosyl diglyceride was present in significant amounts in at least three species of the Rhodospirillaceae and may have been present in most of them, but only in traces. All of the Chromatiaceae species contained several glycolipids, one of which was similar to monogalactosyl diglyceride. Ornithine lipids were found in large amounts in most Rhodospirillaceae, but were absent in Ectothiorhodospira and in the other Chromatiaceae. The species examined could be divided into three groups on the basis of their lipid composition: (i) the genus Ectothiorhodospira; (ii) the remaining Chromatiaceae; and (iii) the Rhodospirillaceae. The data presented are compared with those available in the literature, and differences from other phototrophic organisms are discussed.     

Effect of fucoidans on the developing embryos of the sea urchin <Emphasis Type="Italic">Strongylocentrotus intermedius</Emphasis>

Effect of fucoidans from the Far Eastern brown algae Laminaria japonica, L. cichoroides, and Fucus evanescens on developing embryos of the sea urchin Strongylocentrotus intermedius was studied. Fucoidans from these algae were shown to have different (immunostimulating, inhibitory) effects on the developing embryos. All studied fucoidan fractions added at the zygote stage had a stimulatory effect (acceleration of developmental stages and an increase of life spans) on the developing embryos, with differences by their effective concentrations. Many fucoidans added at the late blastula stage did not produce the stimulatory effect. The lowest number of immunostimulators (only a half of the tested substances) were present among fucoidans from L. japonica cichoriodes. The best immunostimulators that increased 2–3 times the life span of the embryos were heteropolysaccharides containing mannose or xylose apart from L-fucose. Some fucoidans at high concentrations produced an inhibitory effect; they were mainly composed of L-fucose or their monosaccharide composition included, apart from fucose, a significant amount of galactose, but no mannose. The method that we used turned out to be sensitive to structural peculiarities of charged polysaccharides, so it most likely can be applied for evaluation of their immunostimulating properties. From two variants of the experiment the most sensitive was the second one, in which polysaccharides were added at the late blastula stage.Translated from Zhurnal Evolyutsionnoi Biokhimii i Fiziologii, Vol. 41, No. 1, 2005, pp. 51–58.Original Russian Text Copyright © 2005 by Kiseleva, Shevchenko, Krupnova, Zvyagintseva.