Two new farnesylacetone derivatives from the brown alga Sargassum micracanthum

From the brown alga, Sargassum micracanthum, two new farnesylacetone derivatives were isolated and their structures elucidated from spectral analyses and chemical correlation to a known farnesylacetone derivative.     

Lipids and lipid metabolism in the brown alga, Fucus serratus

The lipids of the brown alga Fucus serratus were isolated, identified and quantified. The major acyl lipids were the three glycosylglycerides, diacylgalactosylglycerol, diacyldigalactosylglycerol and diacylsulphoquinovosylglycerol. These represent over 70% of the total acyl lipids. The fatty acid compositions of the major lipids were examined and most showed rather distinctive fatty acid contents. For example, diacylgalactosylglycerol was enriched in n-3 polyunsaturated fatty acids while phosphatidylcholine and phosphatidylethanolamine had very high levels of arachidonate. Phosphatidylglycerol contained the unusual trans-Δ3-hexadecenoic acid. The labelling of lipids and fatty acids from [¹⁴C]acetate was examined and the distribution of label between individual components as a function of the incubation period and in algae collected at different times of the year is reported. Algae collected in the winter incorporated much more radioactivity into non-esterified fatty acids when compared to algae collected in the summer. All algae could label myristate, palmitate, stearate and oleate at high rates. Longer incubation times allowed the labelling of polyunsaturated fatty acids such as linoleic acid.     

Peroxidase activity in the brown alga Laminaria digitata

Cell-free extracts of the brown alga Laminaria digitata catalyse the oxidation of o-dianisidine and of iodide, as well as the formation of iodoamino acids. The enzyme(s) requires hydrogen peroxide for these activities, which are strongly inhibited by cyanide and azide. It is suggested that the activity may be due to a haem-containing peroxidase which, in extracts, is strongly bound, possibly to alginate.     

Brominated phlorethols and nonhalogenated phlorotannins from the brown alga Cystophora congesta

The following phlorotannins were isolated from the brown alga Cystophora congesta and characterized as their acetates: phloroglucinol triacetate, bromodiphlorethol pentaacetate, diphlorethol pentaacetate, bromotriphlorethol-A₁-heptaacetate, bromotriphlorethol-A₂-heptaacetate, tetraphlorethol-C-nonaacetate and fucodiphlorethol-D-decaacetate. The substances bromodiphlorethol pentaacetate, bromotriphlorethol-A₁-heptaacetate and bromotriphlorethol-A₂-heptaacetate are the first brominated members of this series to be described. Triphlorethol-A- heptaacetate was isolated previously from C. congesta.     

Sterols of Agarum cribosum: desmosterol in a brown alga

The sterol composition of the cold water brown alga Agarum cribosum was determined by GC—MS. Six of the seven sterols found were identified as stigmata-5,(E)-24(28)-dien-3β-ol (fucosterol), 24-methylenecholest-5-en-3β-ol (24-methylenecholesterol), cholest-5-en-3β-ol (cholesterol), 3β-hydroxycholest-5-en-24-one (24-ketocholesterol), 24ξ-stigmasta-5,28-diene-3β,24-diol (saringosterol) and cholesta-5, 24-dien-3β-ol (desmosterol).     

Sterols of the senegalese brown alga Padina vickersiae

Contrary to all the brown algae already studied for sterol content the Senegalese Padina vickersiae contains a great amount of cholesterol, chiefly in the later stages of growth. The seasonal variation of the sterols is studied and compared to other Phaeophyceae belonging to the genus Cystoseira.     

Tetraprenyltoluquinols from the brown alga Cystoseira stricta

Four novel metabolites of mixed biogenesis have been isolated from the brown alga Cystoseira stricta and their structures determined by chemical and spectral methods.     

Presence of quorum-sensing inhibitor-like compounds from bacteria isolated from the brown alga Colpomenia sinuosa

Aims:  Several Gram-negative bacterial species use N -acyl homoserine lactone (AHL) molecules as quorum-sensing (QS) signals to regulate various biological functions. Similarly, various bacteria can stimulate, inhibit or inactivate QS signals in other bacteria by producing molecules called as quorum-sensing inhibitors (QSI). Our aim was to screen and identify the epibiotic bacteria associated with brown algae for their ability of producing QS-inhibiting activity.
Methods and Results:  QSI screenings were conducted on several epibiotic bacteria isolated from a marine brown alga Colpomenia sinuosa , using Serratia rubidaea JCM 14263 as an indicator organism. Strain JCM 14263 controls the production of red pigment, prodigiosin by AHL QS. Out of 96 bacteria, which were isolated from the surface of the brown alga, 12% of strains showed the ability to produce QSI, which was observed from the pigmentation inhibition on Ser. rubidaea JCM 14263 without affecting its growth. Phylogenetic analysis using 16S rRNA gene sequencing method demonstrated bacterial isolates showing QS inhibition-producing bacteria belonging to the Bacillaceae (Firmicutes), Pseudomonadaceae (Proteobacteria), Pseudoalteromonadaceae (Proteobacteria) and Vibrionaceae (Proteobacteria).
Conclusion:  An appreciable percentage of bacteria isolated from the brown alga produced QSI-like compounds.
Significance and Impact of the Study:  The screening method using Ser. rubidaea described in this report will facilitate the rapid identification of QSI-producing bacteria from marine environment. This study reveals new avenue for future environmental applications. This study also suggests that these algal epibiotic bacteria may play a role in the defensive mechanism for their host by producing QSI or QSI-like compounds to suppress the settlement of other competitive bacteria.     

Seasonal chemical evolution of the alga Cystoseira elegans

Among the Mediterranean algae belonging to the family Cystoseiraceae analysed for diterpenic compounds, only Cystoseira elegans contains eleganolone, epoxy-eleganolone and elegandiol, as does the Atlantic alga Bifurcaria bifurcata. Surprisingly, for the seasonal Cystoseira elegans, these compounds are present only at the beginning of growth of the alga during Spring and they disappear in the Summer yielding important seasonal variation data for diterpenoids, and also for sterols, alginic acid,mannitol and cellulose.     

Two minor diterpenes related to dictyodial A from the brown alga Dictyota crenulata

4β-Hydroxydictyodial A and 18,O-dihydro-4β-hydroxydictyodial A 18-acetate are two minor aldehydic diterpenes in the brown alga Dictyota crenulata. ¹H NMR and lanthanide-induced chemical shift studies indicate that the relative stereochemistry of both compounds is 2R*, 3R*, 4S*, 10S*.     

Phlorotannins with dibenzodioxin structural elements from the brown alga Eisenia arborea

Twenty-one polyhydroxyphenols, which can all be derived from phloroglucinol, were isolated from Canadian Eisenia arborea (Alariaceae). Most of these compounds contain dibenzo[1,4]dioxin elements and also others benzofuran moieties. The basic component is eckol, a hexahydroxyphenoxydibenzo[1,4]dioxin consisting of three phloroglucinol units. Dioxinodehydroeckol is a benzo[1′,4′]benzodioxino[1,4]benzodioxin derived from eckol. 7,7′-Bieckol, 7,9′-bieckol and 7,2″-bieckol are dimers of eckol with biaryl linkages. 8,4·-Dieckol is a dimeric diphenyl ether. 7-Hydroxyeckol contains one and 7,7′-dihydroxy-9,9′-bieckol two additional hydroxyl groups. 3-Phloroeckol and the dehydro derivatives furodehydroeckol A,B and C are composed of four phloroglucinol rings. Halogenated compounds also occur: monobromo- and monoiodophloroglucinol, 4′-bromo- and 4′-iodoeckol as well as one bromo- and one iodophloroeckol.     

Cytotoxic hydroazulene diterpenes from the brown alga Cystoseira myrica

Cytotoxicity-guided fractionation of the alcohol extract of the brown alga, Cystoseira myrica, afforded four new cytotoxic hydroazulene diterpenes, dictyone acetate (2), dictyol F monoacetate (4), isodictytriol monoacetate (6), and cystoseirol monoacetate (8), together with two known cytotoxic hydroazulene diterpenes, pachydictyol A (1) and dictyone (3). The constitution of each isolated compound has been determined on the basis of spectroscopic and chemical evidence.     

Bacillus algicola sp. nov., a novel filamentous organism isolated from brown alga Fucus evanescens

A slightly yellowish, Gram-positive, filamentous with 'cross-like' branching, aerobic, spore-forming bacterium was isolated from enrichment culture during degradation of the thallus of the brown alga Fucus evanescens. The bacterium studied was chemoorganotrophic, tolerant to 3% NaCl, alkalitolerant, and alginolytic. The predominant cellular fatty acid was ai15:0 which accounted more than 65% of total fatty acids, while i14:0, il5:0 i16:0, and ai17:0 made up 25%. DNA base composition was 37 mol% GC. Phylogenetic analysis of 16S rDNA gene revealed that this isolate was a member of the genus Bacillus, with no close relatives at the species level (16S rRNA gene sequence similarity less 97%). On the basis of the significant differences demonstrated in the phenotypic and chemotaxonomic characteristics, it is suggested that the bacterium be classified as a novel species; the name Bacillus algicola sp. nov. is proposed. The type strain is KMM 3737T (= CIP 107850T).     

Three further dolabellane diterpenoids from Dictyota sp.

A brown alga of the genus Dictyota has yielded three new dolabellane diterpenoids the structures of which were elucidated mainly by spectroscopic methods.     

Genetic regulation of life cycle transitions in the brown alga Ectocarpus

The life cycle of an organism is one of its most elemental features, underpinning a broad range of phenomena including developmental processes, reproductive fitness, mode of dispersal and adaptation to the local environment. Life cycle modification may have played an important role during the evolution of several eukaryotic groups, including the terrestrial plants. Brown algae are potentially interesting models to study life cycle evolution because this group exhibits a broad range of different life cycles. Currently, life cycle studies are focused on the emerging brown algal model Ectocarpus. Two life cycle mutants have been described in this species, both of which cause the sporophyte generation to exhibit gametophyte characteristics. The ouroboros mutation is particularly interesting because it induces complete conversion of the sporophyte generation into a functional, gamete-producing gametophyte, a class of mutation that has not been described so far in other systems. Analysis of Ectocarpus life cycle mutants is providing insights into several life-cycle-related processes including parthenogenesis, symmetric/asymmetric initial cell divisions and sex determination.     

Cytotoxic meroterpenoids from the macroalga Cystoseira abies-marina

Two new meronorsesquiterpenes (cystoazorones A and B) and two new meroditerpenes (cystoazorols A and B), along with benzoic acid were isolated from the brown macroalga Cystoseira abies-marina. The structures of the new compounds were established by 1D and 2D NMR as well as HRMS spectral analysis. The in vitro cytotoxicity and antioxidant activity of the isolated compounds were also evaluated. Cystoazorones A and B, and cystoazorol A exhibited in vitro growth inhibitory activity against HeLa cells. The HeLa cell line in log phase was found to be more sensitive to cystoazorol A than when it was in lag phase. Cystoazorol A also showed a selectivity index higher than taxol, which was used as a positive control. Cystoazorols A and B were found to be the strongest antioxidants among the compounds tested.     

Morphological changes of sperm nuclei during spermatogenesis in the brown alga Cystoseira hakodatensis (Fucales, Phaeophyceae)

Morphological changes and chromatin condensation of sperm nuclei were observed during spermatogenesis in the fucalean brown alga Cystoseira hakodatensis (Yendo) Fensholt. Ultrastructural studies have shown that the mature spermatozoid has an elongated and concave nucleus with condensed chromatin. The morphological changes and the chromatin condensation process during spermatogenesis was observed. Nuclear size decreased in two stages during spermatogenesis. During the first stage, spherical nuclei decreased in size as they were undergoing meiotic divisions and the subsequent mitoses within the antheridium. During the second stage, the morphological transformation from a spherical into an elongated nucleus occurred. Afterwards, chromatin condensed at the periphery in each nucleus, and chromatin‐free regions were observed in the center of the nucleus. These chromatin‐free regions in the center of nucleus were compressed by the peripheral chromatin‐condensed region. As the result, the elongated and concave nucleus of the mature sperm consisted of uniformly well‐condensed chromatin.