Abstracts of J. Oleo Science Vol.50, No.7


REGULAR PAPERS

Structural Characterization of a Novel Series of Fucolipids from the Marine Annelid, Pseudopotamilla occelata,
Saki ITONORI¹, Hideki HAMANA¹, Noriyasu HADA², Tadahiro TAKEDA², John T. DULANEY³ and Mutsumi SUGITA¹,
¹: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, 2-5-1, Hiratsu, Otsu-shi, Shiga-ken 520-0862, JAPAN, ²: Department of Pharmacognosy and Phytochemistry, Kyoritsu College of Pharmacy, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, JAPAN and ³: Department of Medicine, Division of Nephrology, The University of Tennessee, 951 Court Avenue 649D, Memphis TN 38163, USA.
  A novel series of fucolipids, provisionally named CPS and CHS in the previous study, was obtained from whole tissues of the marine annelid, Pseudopotamilla occelata. The structures of these fucolipids were determined by compositional analysis, methylation analysis, gas-liquid chromatography, gas chromatograph-mass spectrometry, proton nuclear magnetic resonance spectroscopy, and matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The structures were shown to be Xylb1-4Fuca1-3GlcNAcb1-3Galb1-4Glcb1-1Cer (CPS₁) and Gal2Mea1-3Fuca1-3GlcNAcb1-3Galb1-4Glcb1-1Cer (CPS₂) for CPS, and Xylb1-4(Gal2Mea1-3)Fuca1-3GlcNAcb1-3Galb1-4Glcb1-1Cer for CHS, respectively. They were structurally related to the previously described ceramide trisaccharide (GlcNAcb1-3Galb1-4Glcb1-1Cer, Amino-CTH) except that a fucose-containing di- and/or trisaccharides were linked to the N-acetylglucosamine residue of the latter lipid. The predominant fatty acids were monoenoic acids, C20 : 1- and C22 : 1 acids amounting to about 80% of the total acids, and octadeca-4-sphingenine was the sole sphingoid base. The fatty acid and sphingoid base compositions showed nearly the same distribution in these fucolipids.
J. Oleo Sci. 50, 537-544 (2001).


Antimutagenic Activity of Isoflavone from Belamcanda chinensis,
Mitsuo MIYAZAWA¹, Katsuhisa SAKANO¹, Sei-ichi NAKAMURA², Hideo SHIMAMURA¹ and Hiroshi KOSAKA²,
¹: Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosaka-shi, Osaka 577-8502, JAPAN and ²: Osaka Prefectural Institute of Public Health, Nakamichi-1, Higashinari-ku, Osaka 537-0025, JAPAN.
  A methanol extract from Belamcanda chinensis showed a suppressive effect on umu gene expression of the SOS response in Salmonella typhimurium TA1535/pSK1002 against the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide). The methanol extract from B. chinensis was re-extracted with hexane, dichloromethane, ethyl acetate and butanol. A suppressive compound in the dichloromethane extract fraction was further fractionated by SiO₂ column chromatography. EI-MS and ¹H and ¹³C NMR spectroscopy were then used to delineate the structure of the compound that confers the observed suppressive effect. Comparison of the obtained spectrum with that found in the literature indicated that iristectorigenin B (1) is the suppressive compound. Iristectorigenin B and its methylated derivative (7, 4'-di-O-methyliristectorigenin B(2)) had the suppressive effects on umu gene expression of the SOS response in Salmonella typhimurium TA1535/pSK1002 against furylfuramide, 4NQO, MNNG, and activated Trp-P-1, which do not require liver metabolic activation by S9. These compounds also showed the suppression of SOS-inducing activity against Trp-P-1 and AfB₁, which require liver metabolizing enzymes. In addition to the antimutagenic activities of these compounds against furylfuramide, Trp-P-1 and activated Trp-P-1 were also assayed by an Ames test using S. typhimurium TA100.
J. Oleo Sci. 50, 545-554 (2001).


Xylosyl Stacking Structure of n-Heptyl b-D-Xyloside in the Hydrous Crystal,
Yutaka ISHIGAMI¹, Midori GOTO², Yasuomi TAKIZAWA¹ and Hirofumi SHINOYAMA³,
¹: Tokyo Gakugei University, 4-1-1, Nukui-kitamachi, Koganei, Tokyo 184-8501, JAPAN, ²: National Institute of Materials and Chemical Research, 1-1, Higashi, Tsukuba, Ibaraki 305-8565, JAPAN and ³: Department of Agricultural Chemistry, Chiba University, 648, Matsudo, Matsudo-shi, Chiba 271-0092, JAPAN.
  The crystal structures of n-heptyl b-D-xyloside were determined by X-ray analysis at a room temperature of 23°C. Hydrous crystals were obtained by a repeated recrystallization from the aqueous solutions of enzymatically synthesized n-hexyl b-D-xyloside. The crystal is orthorhombic, and the space group is P2₁2₁2₁ with Z=8. The cell dimensions are as follows : a=53.215(8), b=8.8301(9), c=6.5276(7)Å, b=95.28°(1). It was confirmed that the molecules formed intermolecular networks in infinite chains linked among the xylosyl OH and H₂O. The high cloud point (33.7°C) of n-hexyl b-D-xyloside in aqueous solutions may be caused by the intermolecular hydrogen bondings of xylosyl OH residues.
J. Oleo Sci. 50, 555-560 (2001).


Effects of Oligosaccharides Having the Glucuronic Acid Residue on Base-Catalyzed Prostaglandin E₂ Dehydration and Isomerization,
Noriyasu HADA, Tadahiro TAKEDA and Shoko YOKOYAMA,
Kyoritsu College of Pharmacy, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, JAPAN.
  Examination was made of the effects of 2-(trimethylsilyl)ethyl 4-O-methyl-b-D-glucopyranosyluronic acid-(1®6)-b-D-galactopyranoside (A), 2-(trimethylsilyl)ethyl 4-O-methyl-b-D-glucopyranosyluronic acid-(1®6)-b-D-galactopyranosyl-(1®6)-b-D-galactopyranoside (B) and N, N', N"-tri-[5-(4-O-methyl-b-D-glucopyranosyluronic acid-(1®6)-b-D-galactopyranosyloxy)pentylcarbonylaminoethyl]- 1, 3, 5-benzenetriamide (C), each possessing the glucuronic acid residue, on drug degradation. Oligosaccharide mixed micelles containing the nonionic surfactant, heptaethyleneglycol dodecylether (HED), were studied so as to assess oligosaccharides A - C for drug stabilization potential. The nonionic surfactant was required since oligosaccharides A - C do not form micelles in single systems. Base-catalyzed dehydration and then isomerization of prostaglandin E₂ (PGE₂), PGE₂®PGA₂®PGB₂, were conducted as model experiments. The rate of the degradation of PGE₂ with base was determined based on concentrations of PGA₂ and PGB₂ using high-performance liquid chromatography. Mixed oligosaccharide-HED micelles inhibited the dehydration and isomerization of PGE₂, possibly owing to suppression of the approach of OH^- as catalysis toward PGE₂ in mixed oligosaccharide-HED micelles by electrostatic repulsion between negatively charged micellar surfaces and OH^-. The clusterized molecular structure of oligosaccharide C was the reason for the inhibition of both these processes. Oligosaccharide C may possibly be situated on the micellar surface and this would lead to greater steric shielding and the above electrostatic repulsion compared to A or B.
J. Oleo Sci. 50, 561-568 (2001).


Assessment of New TLC Method for Measuring Total Polar Compounds in Deteriorated Oils,
Takatoshi TOTOKI and Hideyuki HATANAKA,
Consumer & Office market Tech. Dept., Sumitomo 3M Ltd., 3-8-8 Minami-hashimoto, Sagamihara-shi, Kanagawa 229-1185, JAPAN.
  A new TLC method (3M PCT120) to measure the amount of polar compounds in deteriorated frying oil was developed and launched in Europe. In the new method, a specific dye spotted on a thin layer silica gel plate moves up in proportion to the amount of polar compounds in deteriorated frying oil which is used as a developing solvent. To assess the new method, the amounts of polar compounds in five heated oils were measured by the HPLC method, and the traveling distances of the dye were also measured by 3M PCT120. The result showed a fairly close correlation between the traveling distance of the dye and the amount of polar compounds detected by the HPLC method with a correlation coefficient larger than 0.94.
J. Oleo Sci. 50, 569-573 (2001).


Inhibitory Effect of Cathodic Solution Produced by the Electrolysis of a Dilute NaCl Solution on the Oxidation of Squalene, Vitamin A and b-Carotene,
Eiichi NARA¹, Hiroaki KUBOUCHI¹, Hidetaka KOBAYASHI², Mari KOTAKE², Tetsuya SUZUKI¹ and Kazuo MIYASHITA¹,
¹: Division of Marine Bioscience, Graduate School of Fisheries Science, Hokkaido University, Hakodate 041-8611, JAPAN and ²: National Food Research Institute, Ministry of Agriculture, Forestry and Fisheries, Tsukuba, Ibaraki 305-8642, JAPAN.
  The cathodic solution strongly inhibited the oxidations of squalene, vitamin A palmitate and b-carotene in an aqueous phase, whereas super pure water and NaCl solution had no effect on their oxidations. The strong antioxidant action on b-carotene was also found in the NaOH solution. The cathodic solution and the NaOH solution just after preparation had a scavenging effect on DPPH radical. This result indicates that the radical scavenging effect of these solutions may be in part responsible for their antioxidant action. On the other hand, the radical scavenging effect of both solutions was completely lost by incubation at 37°C in open to air for 7 days, but these incubated solutions still showed a strong antioxidant action. It is therefore suggested that there are other reasons for their antioxidant action than radical scavenging effect. The present study also showed that the NaHCO₃ solution had a strong antioxidant action on b-carotene in the aqueous phase, although this solution had no radical scavenging effect. Since the main molecular species present in the cathodic solution is NaOH and NaOH can change to NaHCO₃ by absorption of CO₂ in the air, these alkaline molecules such as NaOH and NaHCO₃ would be responsible for the antioxidant action of the cathodic solution and of the NaOH solution before and after their incubation.
J. Oleo Sci. 50, 575-581 (2001).


Synthesis and Physiological Activity of Amides and Esters with Carvone Residues,
Masato NOMURA, Yoshifumi MAEGAWA and Yoshihito FUJIHARA,
Department of Chemistry and Environmental Technology, School of Engineering, Kinki University, Umenobe 1, Takaya, Higashihiroshima-shi, Hiroshima 739-2116, JAPAN.
  Synthesis and physiological activity of amides and esters with carvonyl derivatives was examined. d- and l-Carvones (1), (2) were converted to primary amines (3) and (4) by oximation (N, N-dimethylhydrazonation, methylation and elimination reaction) or reduction with LiAlH₄. These carvones were converted to primary alcohols (5), (6) through their reduction with LiAlH₄. The primary amine (3), (4) and alcohol derivatives (5), (6) were made into amides (3a) - (4c) and (5d) - (6f) and esters (5a) - (6c). Eighteen derivatives were obtained and examined for capacity to regulate growth. Six derivatives were found effective as weed control agents (20 g/a) and quite strong by inhibited the growth of Monochoria vaginalis and Echinochloa crus-galli.
J. Oleo Sci. 50, 583-591 (2001).


Effects of Tea Catechins on Diet-induced Obesity in Mice,
Shinichi MEGURO¹, Tomohito MIZUNO¹, Kouji ONIZAWA¹, Keiko KAWASAKI¹, Hideaki NAKAGIRI¹, Yumiko KOMINE¹, Junko SUZUKI¹, Yuji MATSUI¹, Tadashi HASE¹, Ichiro TOKIMITSU¹, Hiroyuki SHIMASAKI² and Hiroshige ITAKURA³,
¹: Biological Science Laboratories, Kao Corporation, 2606 Akabane, Ichi-kaimachi, Haga, Tochigi 321-3497, JAPAN, ²: Department of Biochemistry, Teikyo University School of Medicine, Tokyo, JAPAN and ³: National Institute of Health and Nutrition, Tokyo, JAPAN.
  Examination was made of the effects of tea catechins (TC) on diet-induced obesity. Exposure to high-fat-diet (30% fat) in C57BL/6J mice for 4 weeks induced significant increase in body weight, visceral fat (epididymal, mesenteric, retroperitoneal, perinephric) weight and plasma concentrations of glucose, triacylglycerol and leptin, compared to low-fat diet (5% fat). Treatment with 0.1%TC (high-fat diet +0.1%TC group) had little effect on diet-induced obesity. Relative to high-fat diet and 0.1%TC treatment, 0.5%TC treatment (high-fat diet +0.5%TC group) was noted to bring about significant decrease in body weight, visceral fat weights and plasma leptin. Lipid absorption rate was the same with the high fat diet and 0.5%TC treatment. An oral soluble starch and sucrose (SS-S) tolerance test was conducted on C57BL/6J mice to evaluate the effects of TC to sugar absorption. When the ratio of TC to sum of SS-S was the same as that in the diet composition for the 0.5%TC treatment, the plasma glucose level showed no response. These results demonstrate for the first time TC to have anti-obesity effects on diet-induced obesity in mice, and suggest these effects to be exerted through a mechanism that would not involve inhibition of intestinal absorption of sugar and lipid.
J. Oleo Sci. 50, 593-598 (2001).


Anti-obesity Effects of Tea Catechins in Humans,
Tadashi HASE¹, Yumiko KOMINE¹, Shinichi MEGURO¹, Yoko TAKEDA¹, Hidekazu TAKAHASHI¹, Yuji MATSUI¹, Setsujiro INAOKA¹, Yoshihisa KATSURAGI¹, Ichiro TOKIMITSU¹, Hiroyuki SHIMASAKI² and Hiroshige ITAKURA³,
¹: Biological Science Laboratories, Kao Corporation, 2606, Akabane, Ichikaimachi, Haga, Tochigi 321-3497, JAPAN, ²: Department of Biochemistry, Teikyo University School of Medicine, Tokyo, JAPAN and ³: National Institute of Health and Nutrition, Tokyo, JAPAN.
  To examine the anti-obesity effects of tea catechins in humans, a trial study using healthy male subjects (27-47 years). Comprising in equal number a low dose catechin (LDC) group (n=11) and high dose catechin (HDC) group (n=12). The groups were administered catechins at 118.5 mg and 483.0 mg a day for 12 weeks, respectively. At 4 and 12 weeks, effect evaluation was made based on change in weight, body mass index (BMI), waist circumference, body fat ratio and abdominal fat as determined by computed tomography (CT) and triacylglycerol, total cholesterol, free fatty acid, glucose, insulin and total plasminogen activator inhibitor-1 (PAI-1) in serum. In the HDC group, at 12 weeks, weight, BMI, waist circumference, body fat ratio, abdominal fat and total cholesterol, glucose, insulin, PAI-1 in serum were noted to have significantly decreased from values at 0 week. In the LDC group, only weight, BMI and insulin had changed. In the HDC group, BMI had decreased significantly in 25<=BMI subjects compared to 25>BMI subjects. In the 25<=BMI subjects, BMI decreased significantly more in the HDC group. Tea catechins are thus shown here for the first time to have the anti-obesity effects in humans.
J. Oleo Sci. 50, 599-605 (2001).


NOTE

Fatty Acid Compositions of Muscle and Viscera Lipids in Dominant Limpets Species from Otsuchi Bay in Northern Japan,
Hideki KAWASHIMA¹, Masao OHNISHI² and Hiroo UCHIYAMA³,
¹:Bioscience Laboratory, Miyako College Division, Iwate Prefuctural University, 1-5-1, Ka-nan, Miyako-shi, Iwate 027-0039, JAPAN, ²: Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine, Inada-cho, Obihiro-shi, Hokkaido 080-8555, JAPAN and ³: Water and Soil Environment Division, National Institute for Enviromental Studies, 16-2, Onogawa, Tsukuba-shi, Ibaraki 305-0053, JAPAN.
  In this study, determination was made of lipid and fatty acid compositions of muscle and viscera tissue lipids from three species of limpets from Otsuchi Bay in northern Japan. Dominant limpets contained total lipids at, in muscle and viscera tissues, 0.2 to 1.1% and 1.9 to 9.6%, respectively. Muscle lipids were rich in phosphatidylcholine and phosphatidylethanolamine could be detected in this study. Viscera lipids contained mainly triacylglycerol. Fatty acid compositions of muscle lipids in all species differed considerably from those of viscera lipids, the former being more polyenoic and abundant in 20 : 4n-6 and 20 : 5n-3, accounting for 23-35% of total fatty acids. Seasonal variation was also examined for effects on lipid contents and polyunsaturated fatty acid composition.
J. Oleo Sci. 50, 607-611 (2001).