Content and fatty acid composition of sulfoquinovosyldiacylglycerol in conifer leaves grown in Hokkaido, Japan.

Sulfoquinovosyldiacylglycerol (SQDG) contents in conifer leaves and their fatty acid (FA) compositions were determined. The SQDG content was 16-36 mg/100 g, and was high in Picea glehnii. Palmitic and alpha-linolenic acid were the usually predominant FAs. In Picea, the proportion of alpha-linolenic acid was low, and those of oleic and linoleic acid were high. The essential oil residues of Abies sachalinensis leaves were found to be a potential source of SQDG material.

Simultaneous preparation of purified plasmalogens and sphingomyelin in human erythrocytes with phospholipase A1 from Aspergillus orizae.

A method for the simultaneous purification of plasmalogens and sphingomyelin (SM) in human erythrocytes is described. Treatment of total lipids with n-hexane/acetone (1:1 v/v) resulted in selective precipitation of SM. Both the supernatant and the precipitate fractions were incubated with a phospholipase A(1) (PLA1) from Aspergillus orizae for 3.5 h. The PLA1-treated lipids were extracted with n-hexane/isopropanol, the hexane layer was obtained using a Na(2)SO(4) solution, and the hexane layer was further washed with water. At this step, the relative concentration of the plasmalogens was 92% of the total phospholipids in the supernatant fraction, and that of SM was 97.7% in the precipitate fraction. Each fraction was applied to high performance liquid chromatography (HPLC) for further purification. The plasmalogen and SM obtained were almost free of the other lipids. The purity of the plasmalogens and SM was monitored by HPLC, which can separate intact plasmalogens from their diacyl analogs.

Simultaneous quantification of plant glyceroglycolipids including sulfoquinovosyldiacylglycerol by HPLC-ELSD with binary gradient elution.

Membrane lipids of photosynthetic organisms consist of glycerophospholipids and glyceroglycolipids. We investigated a method for the simultaneous quantitative analysis of neutral and acidic lipids using HPLC-ELSD, and quantified monogalactosyldiacylglycerol (MGDG), digalactosyldiacylglycerol (DGDG) and sulfoquinovosyldiacylglycerol (SQDG). Ten complex lipid classes were separated with a binary gradient system consisting of chloroform and methanol-acetone-water-acetic acid (30:60:9:1, v/v/v/v) with 0.3% triethylamine (pH 4), and were eluted within 16 min. The contents of SQDG in ten edible plants ranged from 3 to 101 mg/100 g, and were positively correlated to the neutral glyceroglycolipids contents.

Analysis of sphingolipid classes and their contents in meals.

Sphingolipids have attracted attention as physiologically functional lipids. We determined their class and content in Japanese meals that had been prepared by a nutritionist, mainly by using HPLC-ELSD. In all 12 meals tested, cerebroside and/or sphingomyelin were generally detected as the major sphingolipids. The total amounts of sphingolipids in typical high- and low-calorie meal samples over 2 days were 292 and 128 mg/day, and 81 and 45 mg/day, respectively.

Prominent differences in leaf fatty acid composition in the F1 hybrid compared with parent trees Larix gmelinii var. japonica and L. kaempferi.

Fatty acid (FA) compositions in leaves were investigated for two families of F(1) hybrids of Larix gmelinii var. japonica x L. kaempferi (F(1)) and their parent clones. Twenty-one FAs, from C(12) to C(32), were found in the leaves of both adult trees and seedlings. The levels of 18:1/(18:2 + 18:3) increased in the order L. kaempferi, F(1), and L. gmelinii var. japonica, with significant differences between L. gmelinii var. japonica and F(1) in adult trees, but these differences were not found in the seedlings. Moreover, in the adult trees, the 18:1/(18:2 + 18:3) levels in the neutral phospholipid fraction and the SigmaC(18)/SigmaC(16), especially in the glycolipid fraction, showed significant differences among the three species. These characteristics are discussed from the viewpoint of lipid synthesis in the endoplasmic reticulum and chloroplasts, and of the activities and substrate specificities in sequential FA desaturation. Linear discriminant analysis suggested that the FA compositions are useable as an index in the identification of hybrid seedlings.

Chemical properties of epidermal lipids, especially sphingolipids, of the Antarctic minke whale.

It is well known that sphingolipids specifically exist in the terrestrial mammal epidermis and correlate with skin barrier functions. However, the lipid properties of the marine mammal epidermis have not been examined in detail. We thus investigated the chemical composition of lipid components, especially sphingolipids, in the black epidermis (outer skin) of Antarctic minke whales (six mature and six immature specimens). Complex lipid fractions mainly contained cerebroside (CE), cholesteryl sulfate and sphingomyelin (SM), as well as two glycerophospholipids. Moreover, in the superficial layer of the black epidermis, CE was richly abundant but phospholipids were scarce. As component fatty acids, the non-hydroxy monounsaturated very long chain fatty acids (VLFA) within 34 carbons were generally present in CE and SM in the black epidermis. CE also consisted of alpha-hydroxy fatty acids with monounsaturation within C34 (17%) and a slight proportion of omega-hydroxy ones (32:1 and 34:1), the latter being probably derived from acyl-CE. Component sphingoid bases of both sphingolipids were predominantly 4-sphingenine (64%), followed by a C16 analogue (21%). When comparing these by different maturities, mature whales showed sphingolipid profiles with higher levels of unsaturated fatty acids and with shorter sphingoid base chains than those of immature ones. Component analysis revealed that CE sugars were 67% glucose and 33% galactose, and alpha-hydroxy fatty acids only bound to galactose.

Ethyl esterification of long-chain unsaturated fatty acids derived from grape must by yeast during alcoholic fermentation.

The composition of total fatty acid ethyl ester (FAEE) in yeast cells and the liquid phase separated from grape must during alcoholic fermentation at different temperatures was investigated by using the solid-phase extraction method. Thirteen FAEE from butyric to linolenic acids were detected during fermentation. Significant amounts of long-chain unsaturated FAEE, including linoleic and linolenic acids derived from grape material, had already accumulated in the yeast cells by day 3 during fermentation.

Fatty acids in must prepared from 11 grapes grown in Japan: comparison with wine and effect on fatty acid ethyl ester formation.

FA components of 11 musts made from grape cultivars grown for making red wine in various regions of Japan and of wines made from the musts were compared to elucidate variety-dependent characteristics and to clarify their effect on FA ethyl ester (FAEE) formation in wine. Sixteen FA with carbon chain lengths from 12 to 26 were detected in all musts, with palmitic, linoleic, and linolenic acids generally predominating. Higher levels of linoleic acid were found in musts from a cold region (Hokkaido), and higher levels of oleic acid occurred in musts from a warm region (Honshu). Moreover, the unsaturation indexes (1.31-1.56) of five grape musts from the cold region showed significant differences among varieties, corresponding to the grapevines' degree of cryotolerance. The FA levels (610-6,610 nmol/100 mL) of all wines were extremely low (1.2-12.8%) compared with those of must, but the FA compositions were similar to those of must. Additionally, significant amounts of FAEE, possibly derived from yeast activity, were found in wines by using a solid-phase extraction method. The amounts of FAEE in wine significantly differed among samples (245-904 nmol/100 mL) and were inversely correlated with the percentage of linoleic acid in musts (R = -0.883). Thus, higher linoleic acid levels in must may be related to lower FAEE formation by yeast.

Dietary sphingolipids ameliorate disorders of lipid metabolism in Zucker fatty rats.

Dietary sphingolipids (SL) inhibit colon carcinogenesis, reduce serum cholesterol, and improve skin barrier function and are considered to be "functional lipids". For comparative determination of the effects of SL with different chemical compositions on lipid metabolism and its related hepatic gene expression, Zucker fatty rats were fed pure sphingomyelin (SM) of animal origin and glucosylceramide (GC) of plant origin. After 45 days, the SM and GC diets led to significant reductions in hepatic lipid and plasma non-HDL cholesterol. Both SM and GC diets decreased plasma insulin levels, whereas only the GC diet increased the plasma adiponectin level. Hepatic gene expression analysis revealed increased expression of adiponectin receptor 2 (Adipor2), peroxisome proliferator-activated receptor alpha (PPARalpha), and pyruvate dehydrogenase kinase 4 (Pdk4). However, expression of stearoyl CoA desaturase (Scd1) was significantly decreased. These results suggest that dietary SL, even of different origins and chemical compositions, may prevent fatty liver and hypercholesterolemia through improvement of adiponectin signaling and consequent increases in insulin sensitivity.

Screening for beneficial effects of oral intake of sweet corn by DNA microarray analysis.

To identify novel functions of the oral intake of sweet corn, we performed DNA microarray analysis of the livers of sweet corn-fed mice. Functional annotation clustering 1600 genes with expression levels that were affected (more than 1.5-fold change) by dietary sweet corn indicated that both cell proliferation and programmed cell death were modulated by sweet corn intake. In the Wnt signaling pathway, which is involved in cell proliferation, the levels of Jun and beta-catenin expression were downregulated by dietary sweet corn. The mRNA levels of Rb and p53, negative regulators of the cell cycle, were increased in mice fed with sweet corn. Dietary corn upregulated expression levels of genes that regulate apoptosis positively (for example, BOK, BID, CASP4). These results suggested that sweet corn is a valuable food for suppressing cancer. Oral administration of sweet corn inhibited tumor growth (36.6% reduce in tumor weight, P < 0.05) in mice inoculated with Ehrlich tumor cells.

Effect of dietary wine pomace extract and oleanolic acid on plasma lipids in rats fed high-fat diet and its DNA microarray analysis.

The aim of this study was to evaluate the concentration of oleanolic acids (OA) in pomace, a winemaking byproduct, and its influence on the levels of plasma lipids in rats fed a high-fat diet and on hepatic gene expression using DNA microarray analysis in vivo. HPLC analyses of pomace ethanol extract (PEE) revealed a high amount of OA ranging from 4 to 11 g/100 g. Male Sprague-Dawley rats were fed a normal-fat diet (NF group), a high-fat diet with 21% lard (HF group), a high-fat diet with 0.05% OA (OA group, 50 mg/kg/day), or a high-fat diet with 0.45% PEE (PEE group, 450 mg/kg/day). Plasma triacylglycerol and phospholipid concentrations were significantly lower in the OA and PEE groups than in the HF group. The microarray analysis of hepatic mRNA revealed reduced expression levels of lipogenic genes including acetyl-CoA carboxylase and glycerol-3-phosphate acyltransferase, probably resulting from the suppression of transcription factor Srebf1 expression. Gene expression of gluconeogensis and inflammatory cytokines was also down-regulated in the OA and PEE groups, suggesting that administration of OA or PEE could ameliorate obesity-induced insulin resistance, as well as prevent hyperlipidemia.

Presence of higher alcohols as ferulates in potato pulp and its radical-scavenging activity.

Higher alcohols with a carbon length ranging from 16 to 30 found in the lipophilic fraction from potato pulp were shown to be present as ferulate and in a free form, but not as wax. Thin-layer chromatography of the neutral lipids in potato pulp indicated a few spots with scavenging activity toward the 1,1-diphenyl-2-picrylhydrazyl (DPPH) stable radical, the major active component being characterized as alkyl ferulate which showed almost the same level of activity as gamma-oryzanol.

Fatty acid compositions of commercial red wines.

A determination was made of fatty acid compositions in twelve commercial red wines made from grapes differing in kind and vintage. Twelve fatty acids were identified, palmitic, myristic, and lauric acids being found predominant. Total acyls (32 approximately 81 nmol/100 ml) differed considerably. Changes in fatty acid constituents in must from grape berries and wines according to the process of manufacture were also examined.

Increased levels of policosanol and very long-chain fatty acids in potato pulp fermented with Rhizopus oryzae.

Significant amounts of policosanol and very long-chain fatty acids (VLFAs) ranging in carbon length from 22 to 30 were found in the lipophilic fraction obtained from potato pulp fermented with Rhizopus oryzae. It is believed that these compounds would have originally been present as suberin-related compounds, but not as wax, in the periderm of potato tubers and concentrated into potato pulp during the process of starch production. Moreover, the policosanol and VLFAs extracted from potato pulp with organic solvents were found to have increased after fermentation.