Ferrocenyl Monomers and Polymers of <Emphasis Type="Italic">N</Emphasis>-Allyl and <Emphasis Type="Italic">N</Emphasis>-Acrylatenaphthalimides

A series of N-allyl, N-ethylmethacrylate and N-phenylmethacrylatenaphthalimide monomers have been prepared with –C=CFc, –C≡CFc and –C≡CSiMe₃ substituents at the 4-position of the naphthalimide ring. All have been characterised by elemental analysis and spectroscopy; the X-ray structure of N-allyl-4-ethenylferrocenylnapththalimide is also reported. Free-radical polymerisation of these monomers gave homopolymers, random co- and terpolymers with polydispersities ranging from 1.7 to 3.2. Incorporation into a polymer matrix has no effect on the spectroscopic and electrochemical properties of the naphthalimide or ferrocenyl components. The ferrocenyl polymers are electrochromic and when oxidised give naphthalimide charge-transfer bands in the NIR; this electrochromism was examined by OTTLE techniques.     

Molecular-hydrodynamic study of poly(<Emphasis Type="Italic">N</Emphasis>-methyl-<Emphasis Type="Italic">N</Emphasis>-vinylacetamide) macromolecules

High-velocity sedimentation, translational isothermal diffusion, and viscometry in H₂O and DMF are used to investigate the samples and fractions of poly(N-methyl-N-vinylacetamide) synthesized by free-radical polymerization and fractionated in a chloroform-diethyl ether system. Molecular masses M and the Mark-Kuhn-Houwink-Sakurada relations are obtained for the fractions in the molecular mass range M × 10⁻³ = 3.5−540.0. The negative temperature coefficient of intrinsic viscosity is revealed for both solvents. The length of the Kuhn statistical segment and the hydrodynamic diameter of poly(N-methyl-N-vinylacetamide) macromolecules are estimated; the hydrodynamic volumes occupied by water-soluble poly(N-methyl-N-vinylacetamide), poly(1-vinyl-2-pyrrolidone), poly(vinylformamide), and pullulan molecules are compared.     

New cerebrosides from the basidiomycete <Emphasis Type="Italic">Cortinarius tenuipes</Emphasis>

Five cerebrosides (1–5), including three new ones named cortenuamide A (1), cortenuamide B (2), and cortenuamide C (3), were isolated from the fruiting bodies of the basid-iomycete Cortinarius tenuipes. The structures of those compounds were elucidated as (4E,8E)-N-d-2′-hydroxytetracosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (1), (4E,8E)-N-d-2′-hydroxytricosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8 sphingadienine (2), (4E, 8E)-N-d-2′-hydroxydocosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (3), (4E, 8E)-N-d-2′-hydroxyoctadecanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (4), and (4E, 8E)-N-d-2′-hydroxypalmitoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (5) by spectral and chemical methods.     

Management of <Emphasis Type="Italic">Cosmopolites sordidus</Emphasis> and <Emphasis Type="Italic">Metamasius hemipterus</Emphasis> in Banana by Pheromone-Based Mass Trapping

Mass trapping Cosmopolites sordidus (Coleoptera, Curculionidae) using a pheromone-baited pitfall trap and Metamasius hemipterus (Coleoptera, Curculionidae) using a pheromone-sugarcane-baited open gallon trap was conducted in commercial banana. Four traps for each insect per hectare were placed in each of two 5-hectare plots of banana. Two additional 5-hectare plots were designated as controls and treated according to the plantation protocol. Capture rates of C. sordidus and M. hemipterus declined by >75 % over 10–12 months. In the banana growing region studied, corm damage was due primarily to C. sordidus, while only a minor amount of damage was attributable to M. hemipterus. Corm damage reduction in trapping plots was, thus, attributed primarily to C. sordidus trapping. In trapping plots, corm damage decreased by 61–64 % during the experiment. Banana bunch weights increased 23 % relative to control plots after 11–12 months of trapping. Fruit diameter did not vary between bunches harvested from trapping plots vs. control plots. Plant vigor, however, as determined by stem circumference at one meter above ground increased in plots with traps compared to control plots. Trapping for C. sordidus in two plantations of over 200 hectares each, reduced corm damage 62–86 % relative to pre-trapping levels. Insecticide control measures in place when the experiment commenced resulted in about 20–30 % corm damage, while use of pheromone trapping to manage C. sordidus lowered corm damage to 10 % or less. It is estimated that the increase in value of increased yield obtained in this trial (23 %) is about 4,240 USD per year per hectare, while the cost of pheromone trapping is approximately4,240 USD per year per hectare, while the cost of pheromone trapping is approximately 185 USD per year per hectare. The trapping program becomes revenue neutral if bunch weights increase by an average of 1 % per year of trapping. Approximately 10 % of all plantation area in Costa Rica use the pheromone trapping system described here. The system also is used in Martinique, Guadeloupe, and the Canary Islands.     

Cyanolipid-rich seed oils from <Emphasis Type="Italic">Allophylus natalensis</Emphasis> and <Emphasis Type="Italic">A. dregeanus</Emphasis>

As a continuation of our study on plants of the Sapindaceae, the chemical composition of the oil extracted from seeds of Allophylus natalensis (Sonder) De Winter and of A. dregeanus (Sonder) De Winter has been investigated. The oil from both species contained approximately equal amounts of TAG and type I cyanolipids (CL), 1-cyano-2-hydroxymethylprop-2-en-1-oldiesters, with minor amounts of type III CL, 1-cyano-2-hydroxymethylprop-1-en-3-ol-diesters. Structural investigation of the oil components was accomplished by chemical, chromatographic (TLC, CC, GC, and GC-MS), and spectroscopic (IR, NMR) means. GC and GC-MS analysis showed that C₂₀ FA were dominant in the CL components of the oil from the two species (44–80% vs. 21–26% in TAG), with cis-11-eicosenoic acid (36–46%) and cis 13-eicosenoic acid (paullinic acid, 23–37%) as the major esterified fatty acyl chains in A. natalensis and A. dregeanus, respectively. cis-Vaccenic acid was particularly abundant (11–31%) in the CL from A. dregeanus, whereas eicosanoic acid (10–22%) was also a major component of CL in both species.     

Chemical Structure of <Emphasis Type="Italic">Bacteriovorax stolpii</Emphasis> Lipid A

Bdellovibrionales is a phylogenetically diverse group of predatory prokaryotes, which consists of the two families Bdellovibrionaceae and Bacteriovoracaceae. We describe LPS and lipid A of the type strain Bacteriovorax stolpii DSM 12778, representing the first characterized endotoxin of a Bacteriovoracaceae member. It has a smooth form LPS, which was identified by SDS-polyacrylamide gel electrophoresis. The lipid A structure was determined by combined gas chromatography–mass spectrometry, electrospray ionization mass spectrometry and NMR spectroscopy. Its backbone consists of two β-(1 → 6)-linked 2,3-diamino-2,3-dideoxy-d-glucopyranoses (GlcpN3N) carrying a pyrophosphoethanolamine at O-4′ of the non-reducing sugar and a phosphate group linked to O-1 of the reducing GlcpN3N. Positions 2, 3, 2′ and 3′ of the two GlcpN3N are acylated with primary 3-hydroxy fatty acids and one of those carries a secondary fatty acid.     

Synthesis of Phosphatidylcholine Through Phosphatidylethanolamine <Emphasis Type="Italic">N</Emphasis>-Methylation in Tissues of the Mussel <Emphasis Type="Italic">Mytilus galloprovincialis</Emphasis>

We previously demonstrated the importance of upregulation of phosphatidylethanolamine N-methylation pathway in euryhaline fish and crustaceans facing hyperosmotic conditions. In marine molluscs phosphatidylcholine synthesis through N-methylation of phosphatidylethanolamine has not been described until now. In vivo labeling of the mussel Mytilus galloprovincialis with [1-³H]-ethanolamine showed that the digestive gland is the tissue expressing the highest incorporation into lipids. A sustained increase in lipid labeling was observed up to 72 h following label injection with 79–92% of radioactivity concentrated into phosphatidylethanolamine and phosphatidylcholine. A direct correlation (r = 0.47, p < 0.01) between the specific radioactivities of phosphatidylcholine in plasma and the digestive gland was observed. Moreover, the phosphatidylcholine fatty acid compositions of plasma and the digestive gland were similar but differed from those of phosphatidylcholine purified from other tissues. In vitro incubation of tissues with [1-³H]-ethanolamine or L-[3-³H]-serine showed that a significant labeling of the choline moiety of phosphatidylcholine was observed in the digestive gland and hemocytes. Pulse-chase experiments with [1-³H]-ethanolamine also demonstrated that hemocytes are exchanging the newly formed phospholipids with plasma. Finally, phosphatidylethanolamine N-methyltransferase assays demonstrated salinity-dependent activities in the digestive gland and hemocytes. We conclude that in M. galloprovincialis an active phosphatidylcholine synthesis through N-methylation of phosphatidylethanolamine occurs in the digestive gland and hemocytes and that this newly formed phosphatidylcholine is partly exchanged with plasma.     

Antibacterial Activity of Essential Oil and Extracts of <Emphasis Type="Italic">Cleistocalyx operculatus</Emphasis> Buds Against the Bacteria of <Emphasis Type="Italic">Xanthomonas</Emphasis> spp.

This study was undertaken to assess the antibacterial efficacy of the essential oil and extracts of Cleistocalyx operculatus buds against plant pathogenic bacteria of Xanthomonas spp. The diameter of inhibition zones of oil (1,000 μg/disc) and extracts (1,500 μg/disc) against the tested bacteria were found in the range of 7–23 mm. The MIC and MBC values of the oil and extracts against the tested Xanthomonas spp. ranged from 31.25–125 to 62.5–250 μg/ml and 125–500 and 250–1,000 μg/ml, respectively. The cell viability study demonstrated a potential detrimental effect of the oil (1,000 μg/ml) and hexane extract (250 μg/ml) on the tested Xanthomonas spp. Also the oil displayed significant antibacterial effects in vivo against Xoo KX019 and Xsp SK12 conducted on greenhouse-grown oriental melon plants (Cucumis melo L. var. makuwa). The results of this study suggest that C. operculatus-derived essential oil and extracts could be used as natural bactericides in the food and agriculture industries.     

Synthesis and Properties of 1,1-bis{[3-(<Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-Dimethylamino)propyl]amido}alkane-di-<Emphasis Type="Italic">N</Emphasis>-oxides

A homologous series of new surface-active 1,1-bis{[3-(N,N-dimethylamino)propyl]amido}alkane-di-N-oxides were synthesized in the reaction of an appropriate diethyl 2-alkylmalonate with N,N-dimethylamino-1,3-propanediamine followed by oxidation with aqueous hydrogen peroxide. The adsorption isotherms of their aqueous solutions were measured and evaluated to obtain adsorption parameters: critical micelle concentration (CMC), surface excess concentration (Γ_CMC), equilibrium surface tension at the CMC (γ_CMC), cross-sectional area of the adsorbed surfactant molecule (A _CMC), efficiency of surface adsorption (pC₂₀), standard free energies of adsorption (ΔG°_ads), and micellization (ΔG°_CMC). All investigated di-amidoamines and di-N-oxides were practically non-toxic to selected bacteria and yeasts. These compounds are readily biodegradable in the Closed Bottle Test inoculated with activated sludge. Surface and biological properties showed that this group of N-oxide-type compounds has high surface activity and fulfills requirements for environmental acceptance.

Solubility of Two Disperse Dyes Derived from <Emphasis Type="Italic">N</Emphasis>-Alkyl and <Emphasis Type="Italic">N</Emphasis>-Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

The solubility of naphthalimide-based monoazo dyes containing N-ethyl and N-ethanoic acid groups was investigated in the presence of a conventional monomeric counterpart (DTAB) and two cationic gemini surfactants (12-4-12 or 14-4-14) individually. The effective parameters on dye solubility such as temperature, time and concentration of surfactants were investigated by UV–Visible spectrophotometry. The results demonstrate that the solubility of both dyes was considerably increased at concentrations above the surfactant CMC. The wavelength for the maximum absorbance of dyes in the aqueous solution shifts toward longer wavelengths with changes in the concentration of the cationic surfactants. A kinetic study of solubilization of dyes in cationic surfactants solution showed that the rate of solubilization follows the pseudo-first-order reactions. Rates of solubilization were in the range of 0.5 × 10⁻³ to 6.8 × 10⁻³ min⁻¹ for both dyes. The disperse dye containing a carboxylic acid group (dye 2) has a higher solubility rate than the dye containing an alkyl group (dye 1). The type of surfactant has a very low effect on adsorption of dye 1 onto the polyester fibers, whereas changing the surfactant type from DTAB to 12-4-12 or 14-4-14 causes adsorption of dye 2 on polyester to decrease.     

Electrosynthesis of nitroso compounds from (<Emphasis Type="Italic">1</Emphasis><Emphasis Type="Bold">S</Emphasis>, <Emphasis Type="Italic">2</Emphasis><Emphasis Type="Bold">S</Emphasis>)-2-amino-l-(4-nitrophenyl)-propane-1,3-diol derivatives

Nitroso compounds were electrogenerated from (1S, 2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol derivatives (derivatives of p-nitrophenylserinol) in a “redox” flow cell equipped with two consecutive porous electrodes of opposite polarities. In spite. of the relative instability in methanol-acetate buffer of the hydroxylamine intermediates produced at the first porous electrode (cathode), the nitroso derivatives were prepared in good yields at the second one (anode). A coupling reaction between some nitroso derivatives and p-toluenesulphinic acid led to N-sulphonylphenylhydroxylamines.     

<Emphasis Type="Italic">Santalum </Emphasis><Emphasis Type="Italic">insulare</Emphasis> Acetylenic Fatty Acid Seed Oils: Comparison within the <Emphasis Type="Italic">Santalum</Emphasis> Genus

The sandalwood kernels of Santalum insulare (Santalaceae) collected in French Polynesia give seed oils containing significant amounts of ximenynic acid, E-11-octadecen-9-oic acid (64–86%). Fatty acid (FA) identifications were performed by gas chromatography/mass spectrometry (GC/MS) of FA methyl esters. Among the other main eight identified fatty acids, oleic acid was found at a 7–28% level. The content in stearolic acid, octadec-9-ynoic acid, was low (0.7–3.0%). An inverse relationship was demonstrated between ximenynic acid and oleic acid using 20 seed oils. Results obtained have been compared to other previously published data on species belonging to the Santalum genus, using multivariate statistical analysis. The relative FA S. insulare composition, rich in ximenynic acid is in the same order of those given for S. album or S. obtusifolium. The other compared species (S. acuminatum, S. lanceolatum, S. spicatum and S. murrayanum) are richer in oleic acid (40–59%) with some little differences in linolenic content.     

New ceramides from <Emphasis Type="Italic">Rantherium suaveolens</Emphasis>

A mixture of five new ceramides was isolated from the aerial parts of Rantherium suaveolens and characterized by spectroscopic and chemical methods. Their structures were elucidated by spectroscopic and chemical methods as (2S, 3S, 4R, 2′R, 14E)-2-(2′-hydroxydocosanoylamino)-14-octadecene-1,3,4-triol (1), (2S,3S,4R,2′R, 14F)-2-(2′-hydroxytricosanoylamino)-14-octadecene-1,3,4-triol (2), (2S,3S,4R,2′R,14F)-2-(2′-hydroxytetracosanoylamino)-14-octadecene-1,3,4-triol (3), (2S,3S,4R,2′R,14E)-2-(2′-hydroxypentacosanoylamino)-14-octadecene-1,3,4-triol (4), and (2S,3S,4R,2′R,14E)-2-(2′-hydroxyhexacosanoylamino)-14-octadecene-1,3,4-triol (5).     

Fractionation and characterization of proteins from <Emphasis Type="Italic">Gevuina avellana</Emphasis> and <Emphasis Type="Italic">Rosa rubiginosa</Emphasis> seeds

Gevuina avellana and Rosa rubiginosa proteins were evaluated for their potential food use. The proteins were sequentially separated into five fractions according to their solubilities in deionized water, 0.5 M NaCl, 70% (vol/vol) isopropyl alcohol, 50% (vol/vol) glacial acetic acid, and 0.1 M NaOH. The five fractionated protein groups were then characterized by SDS-PAGE and gel filtration chromatography to determine their M.W. profiles. Ninety-six percent of G. avellana total protein was solubilized in three extraction stages, and 88% of R. rubiginosa total protein was solubilized in one extraction stage. Albumins were the major protein fraction in G. avellana and glutelins-1 the most abundant in R. rubiginosa. The protein solubility profile determined over the pH range 1–12 showed minimal solubilities at pH 3–5 and pH 3–7 for G. avellana and R. rubiginosa, respectively. Electrophoretic studies revealed the existence of proteins composed of two major kinds of polypeptides linked together via disulfide bonds and with molecular masses ranging from 13 to 119 kDa. Gel filtration chromatography profiles of globulins and albumins were studied for both seeds. Isoelectric focusing showed an isoelectric point in the ranges of 4.5–6 and 3–6.5 for G. avellana and R. rubiginosa proteins, respectively.     

In Vitro Antioxidant Properties of Hemp Seed (<Emphasis Type="Italic">Cannabis sativa</Emphasis> L.) Protein Hydrolysate Fractions

Simulated gastrointestinal hydrolysis of hemp seed proteins using pepsin and pancreatin followed by membrane ultrafiltration fractionation yielded fractions with peptide sizes of <1, 1–3, 3–5, and 5–10 kDa. Analysis of in vitro antioxidant properties showed that the hemp seed protein hydrolysate (HPH) exhibited a significantly weaker (p < 0.05) scavenging of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals when compared to the fractionated peptides. Metal chelation activity of the HPH was significantly greater (p < 0.05) than the activities of fractionated peptides. Fractionation of the HPH led to significant (p < 0.05) improvements in ferric reducing power, DPPH, and hydroxyl radical scavenging radical activities but decreased metal chelation capacity. Peptide fractions with longer chain lengths (3–5 and 5–10 kDa) had better metal chelation and ferric reducing power than the <1, and 1–3 kDa fractions. HPH and all the peptide fractions significantly inhibited (p < 0.05) linoleic acid oxidation when compared to the control. Glutathione (GSH) had significantly greater (p < 0.05) ferric reducing power, and scavenging of hydroxyl and DPPH radicals when compared to HPH and fractionated peptides. In contrast, HPH and peptide fractions >3 kDa had significantly higher (p < 0.05) metal chelation activity than GSH. The results show the potential use of HPH and peptide fractions of defined size for the treatment of oxidative stress-related diseases.     

Antibacterial and xanthine oxidase inhibitory cerebrosides from <Emphasis Type="Italic">Fusarium</Emphasis> sp. IFB-121, and endophytic fungus in <Emphasis Type="Italic">Quercus variabilis</Emphasis>

Two antibacterial and xanthine oxidase inhibitory cerebrosides, one of which is chemically new, were characterized from the chloroform-methanol (1∶1) extract of Fusarium sp. IFB-121, an endophytic fungus in Quercus variabilis. By means of chemical and spectral methods [IR, electrospray ionization MS (ESI-MS), tandem ESI-MS, ¹H and ¹³C NMR, distortionless enhancement by polarization transfer, COSY, heteronuclear multiple-quantum coherence, heteronuclear multiple-bond correlation, and 2-D nuclear Overhauser effect correlation spectroscopy], the structure of the new metabolite named fusaruside was established as (2S,2′R,3R,3′E,4E,8E,10E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8,10-sphingatrienine, and the structure of the other was identified as (2S,2′R,3R,3′E,4E,8E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8-sphingadienine. Both new and known cerebrosides, although inactive to Trichophyton rubrum and Candida albicans, showed strong antibacterial activities against Bacillus subtilis, Escherichia coli, and Pseudomonas fluorescens, with their minimum inhibitory concentrations being 3.9, 3.9, and 1.9 μg/mL, and 7.8, 3.9, and 7.8 μg/mL, respectively. Furthermore, both metabolites were inhibitory to xanthine oxidase, with the IC₅₀ value of fusaruside being 43.8±3.6 μM and the known cerebroside being 55.5±1.8 μM.     

Biosynthesis of (3<Emphasis Type="Italic">Z</Emphasis>,6<Emphasis Type="Italic">Z</Emphasis>,9<Emphasis Type="Italic">Z</Emphasis>)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of <Emphasis Type="Italic">Erannis bajaria</Emphasis>

The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography–mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H.     

Study of the kinetics of oxidation of amines by potassium ferricyanide in the presence of <Emphasis Type="Italic">N,N</Emphasis>-dimethyldodecylamine <Emphasis Type="Italic">N</Emphasis>-oxide

This research reports on the oxidation of different amines such as dibutylamine, diethylamine, dipropylamine, ethylamine, ethylmethylamine, propylamine, triethylamine, and trimethylamine by 0.001 M potassium ferricyanide in the presence of 0.03 M NaOH at 25°C in aqueous medium and/or in 0.03 M N,N-dimethyldodecylamine N-oxide (DDAO). Oxidation rates were studied with a spectrophotometer at 420 nm. The experimental data showed that the reaction was first-order with respect to [amine] _T and [Fe(CN)₆]³⁻. Also, the rate constant (k _obs) had values within the concentration range of 0.015–0.05 M of NaOH and increased above the critical micelle concentration values of DDAO. The dependence of the reaction rate on the nature of the salt was also investigated, and the thermodynamic parameters ΔG ^*, ΔH ^*, and ΔS ^* were calculated. A pseudo-phase model was applied to the system, and the binding constant of the amine to DDAO micelles was calculated.     

Synthesis,Characterization and Properties of <Emphasis Type="Italic">N</Emphasis>-Alkyl-<Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-di(2-hydroxyethyl) Amine Oxides

N‐Dodecyl‐N,N‐di(2‐hydroxyethyl) amine oxide (C₁₂DHEAO) and N‐stearyl‐N,N‐di(2‐hydroxyethyl) amine oxide (C₁₈DHEAO) were synthesized with N‐alkyl‐diethanolamine and hydrogen peroxide. Their chemical structures were confirmed using ¹H‐NMR spectra, mass spectral fragmentation and FTIR spectroscopic analysis. It was found that C₁₂DHEAO and C₁₈DHEAO reduced the surface tension of water to a minimum value of approximately 28.75 mN m^?1 at concentration of 2.48 × 10^?3 mol L^?1 and 32.45 mN m^?1 at concentration of 5.21 × 10^?5 mol L^?1, respectively. The minimum interfacial tension (IFT_min) and the dynamic interfacial tension (DIT) of oil–water system were measured. When C₁₈DHEAO concentration was in the range of 0.1–0.5%, the IFT_min between liquid paraffin and C₁₈DHEAO solutions all reached the ultra‐low interfacial tension. Furthermore, their foam properties were investigated by Ross‐Miles method, and the height of foam of C₁₂DHEAO was 183 mm. It was also found that they showed strong emulsifying power.     

New 2-Methyl-13-Icosenoic Acid from the Temperate Calcisponge <Emphasis Type="Italic">Leuconia johnstoni</Emphasis>

The fatty acid composition of the temperate calcareous marine sponge Leuconia johnstoni Carter 1871 (Calcaronea, Calcarea) was characterized for the first time in specimens collected off the Brittany coast of France over four years from October 2005 to September 2008. Forty-one fatty acids (FA) with chain lengths ranging from C₁₄ to C₂₂ were identified as fatty methyl esters (FAME) and N-acyl pyrrolidide (NAP) derivatives by gas chromatography–mass spectrometry (GC–MS). Twenty-two saturated fatty acids (SFA) were identified accounting for 52.1–59.0% of the total FA and dimethylacetals (DMA). In addition, among the SFA, we noticed the presence of numerous methyl-branched iso and anteiso FA, suggesting a large number of associated bacteria within L. johnstoni. Thirteen monounsaturated fatty acids (MUFA, 28.0–36.0% of total FA + DMA) were also identified as well as six polyunsaturated fatty acids (PUFA, 4.0–8.2%). A noticeable DMA was detected at a high level, particularly in September 2008 (11.8%), indicating the presence of plasmalogens in this sponge species. This calcareous sponge lacked the non-methylene-interrupted FA (NMI FA) with a Δ5,9 system typical of siliceous Demosponges and Hexactinellids. The occurrence of the unusual 8,13-octadecadienoic acid was reported for the first time as a minor PUFA in a calcareous sponge. The major FA, representing 20–25% of this sponge FA, was identified as the new 2-methyl-13-icosenoic acid from mass spectra of its methyl ester and its corresponding N-acyl pyrrolidide derivatives as well as a dimethyl disulfide adduct.