Abstracts of J.Oleo Science Vol. 50, No.5


Oilseed Crops with Modified Fatty Acid Composition,
F.D. GUNSTONE,
Scottish Crop Research Institute, Invergowrie, Dundee, DD2 5DA Scotland, UK.
In considering oilseed crops with modified fatty acid composition three questions have to be addressed: why is it necessary to have oils and fats with composition different from that supplied by nature ? how can such changes be accomplished ? and what modified material is already available or likely to be so in the near future ?
Our increased understanding of the nutritional properties necessary to provide healthy food and of the physical properties required for good quality spreads or frying oils allow us to write specifications for ideal oils in terms of their fatty acid composition. However, this may not be sufficient. We may need to define triacylglycerol composition and, at the same time, to manage the minor components which also have a marked influence on shelf life and on dietary properties.
Our desire to modify fatty acid composition is at least one century old and over that period of time a range of methods-some technological and some biological-have been developed. This lecture is confined to the consideration of producing modified seed oils by conventional seed breeding or by transgenic modification.
Efforts have been directed particularly to changing the levels of saturated acids, oleic acid, and linolenic acid-sometimes raising these and sometimes lowering them. These changes have been applied to the major oilseeds-soybean, rapeseed/canola, and sunflower- and also to linseed. However, because of inadequate control of triacylglycerol composition, and the minor components, the new oils have not always displayed the desired properties.
J. Oleo Sci. 50, 269-279 (2001).

Perspectives on the Sustainable Growth of Asian-Pacific Surfactant and Detergent Industries towards the New Millennium,
T. YANAGAWA,
Research & Development Headquarters, LION Corporation, 13-12 Hirai 7-Chome, Edogawa-ku, Tokyo 132-0035, JAPAN.
The spirit of Asian-Pacific people is based on the self-sufficiency through a symbiosis with nature that grows out of the circulation of rain and water. In this lecture, I would like to propose a scenario and three key concepts for the sustainable growth of Asian-Pacific surfactant and detergent industries within the background of the Asian-Pacific spiritual dimension and traditional culture.
Taking best advantages of Asia's fat and oil resources favored by abundant nature
Enhanced capabilities and new products based on technical innovation
Paradigm shift to Asian values and a recycling society in the S&D industries
We should not simply rely on Western technology and the introduction of products. Our fundamental objective should rather be to promote the development of Asia's own unique products and technologies that reflect the Asia's spirits of living in cyclic harmony with nature. There can be no question that, through cooperative ties and lively discussions on Western technology, active involvement in planning based on our own technical prowess will be the true basis of sustainable growth of Asian-Pacific surfactant and detergent industries into the new millennium.
J. Oleo Sci. 50, 281-293 (2001).

New Palm-Based Products,
Y. BASIRON,
Malaysian Palm Oil Board (MPOB) No.6, Persiaran Institusi, Bandar Baru Bangi, 43000 Kajang, Selangor, MALAYSIA.
An oil palm is perennial crop. The palm begins to bear fruits 2-3 years after planting and has an economic life of about 25 years. Among the oil crops, the oil palm is the most prolific oil producing plant. In Malaysia, the commercial planting material is Tenera which yields about 4 tonnes of palm oil, 0.5 tonne palm kernel oil (PKO) and 0.6 tonne palm kernel cake (PKC) per hectare per year on the average.
An oil palm fruit yields two types of oil, crude palm oil (CPO) and palm kernel oil (PKO). CPO and PKO are extracted from the mesocarp and kernel of the oil palm fruit respectively. They are chemically different and have between them practically the entire range of long, medium and short chain fatty acids. CPO contains mainly palmitic (C16:0) and oleic acids (C18:1), the two most common fatty acids in nature, and is about 50% saturated, while PKO contains mainly lauric acid (C12:0) and is more than 80% saturated.
Based on their chemical and physical properties, two large industries have been established namely palm-based food industry and oleochemical industry. In addition, the presence of healthy components such as carotenes and vitamin E as well as its high content of monounsaturates has made palm oil a nutritious edible oil.
About 80% of palm oil find its way into food products, leaving about 20% for non-applications. MPOB's R&D efforts have, over the last few years, producers many new palm-based products. The food products include Trans-free vanaspati, santan powder, Trans-free margarine, pourable margarine, microencapsulated palm oil-based products, non-dairy ice cream, shortenings, cocoa butter substitute, reduced fat spread, Trans fatty acid free food formulation, palm olein salad dressing, etc.
There are many useful minor components in crude palm oil. Among the more important ones are carotenes, tocols (30% tocopherols and 70% tocotrienools), sterols and squalene. Until recently, many of these minor components have been lost during refining :- all carotenes are destroyed and about 30% of vitamin E is condensed in palm fatty acid distillate, a by-product during refining of palm oil. Processes have been developed to recover these minor components and these have contributed to the emergence of nutraceutical industry that produces tocopherol and tocotrienol capsules, carotene rich palm oil and palm carotene concentrate.
Palm oil also finds many of its applications in oleochemical industry. Coconut oil and tallow are the traditional raw materials for oleochemicals. However, because of their similarity in fatty acid composition, palm oil, palm stearin and palm kernel oil have been accepted as better alternatives. In fact, palm oil and palm kernel oil offer more advantages :
They are more reliable in supply and delivery.
They are more cost-effective
As vegetable oils, their derivatives and applications are fully acceptable to people for whom animal fats may be subjected to religious taboos.
State-of-the-art technologies are employed in the oil palm industry in Malaysia. However, for the industry to remain competitive, R&D efforts towards product innovations and process improvements are essential. MPOB has concentrated its efforts in market driven R&D and has produced many marketable products. Among these palm-based products are surfactants that are more environmentally friendly, printing ink, methyl esters (palm diesel), lubricants, polyurethane, coating-paper for food wrappers, candles, products in deinking of waste papers, glycerine soap, hydroxy fatty acids, cosmetics and personal care products (a range of goat's milk incorporated products). Great emphasis is being placed on the development of palm based active ingredients for the production of high-end value-added consumer products.
Lately MPOB has embarked on an extensive and intensive R&D programme in palm biomass utilization. It has been shown that oil palm biomass offers great potential for producing medium density fibre board (MDF), thermoforable plastic composites, pulp and paper, furniture etc.
Putting knowledge in converting our resources into value added end products is consistent with national government's effort to transform the nation from a resource-based industry into a manufacturing-based industry so that the country will become a fully developed industrialized nation by the year 2000.
J. Oleo Sci. 50, 295-303 (2001).

Balanced Intake of Polyunsaturated Fatty Acids for Health Benefits,
M. SUGANO,
Faculty of Environmental and Symbiotic Sciences, Prefectural University of Kumamoto, Tsukide 3-1-100, Kumamoto 862-8502, JAPAN.
The fat intake pattern of Japanese that was estimated from the annual report of national nutrition survey was introduced as a comprehensive model for a healthy way of eating polyunsaturated fatty acids (PUFA). The n-6/n-3 ratio of 4 and the polyunsaturated/saturated (P/S) ratio of 1 in the recommended dietary allowance (RDA) of fat for Japanese that was announced in 2000 essentially reflects a relatively high value of these ratios in our dietary habit. This review stresses the advantage of Japanese way of eating, in which moderate eating is indispensable, for health benefits.
J. Oleo Sci. 50, 305-311 (2001).

Lipid Peroxidation and Its Inhibition : Overview and Perspectives,
E. NIKI,
Utsunomiya University, Department of Applied Chemistry, 7-1-2 Yoto, Utsunomiya 321-8585, JAPAN.
Lipid peroxidation and its inhibition have received much attention as one of the most important issues in the field of oleo-science. The essential bioactive compounds are formed in vivo by lipid peroxidation, but it is also known to cause oxidative damage of foods, cosmetics, and oil products and furthermore to be involved in the oxidative stress in vivo. For example, the lipid peroxidation in the membranes induces the disturbance of its fine structure and function and the oxidative modification of low density lipoprotein is accepted as a key initial event in the progression of atherosclerosis. Consequently, the role of antioxidants has been appreciated against the oxidative damage both in vitro and in vivo. The states-of-art and perspectives of the lipid peroxidation and its inhibition are briefly reviewed with special emphasis on their dynamics in heterogeneous systems.
J. Oleo Sci. 50, 313-320 (2001).

Projecting USDA Research into the 21st Century,
F. P. HORN,
Agricultural Research Service, U.S. Department of Agriculture, 302-A, 14th and Independence Ave., SW, Washington, D.C. 20250, USA.
No abstract.
J. Oleo Sci. 50, 321-327 (2001).

Lipid Analysis of PUFA in the New Millennium and Future Trends,
S. WADA,
Tokyo University of Fisheries, Department of Food Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo 108-8477 JAPAN.
Polyunsaturated fatty acids (PUFA), especially highly unsaturated fatty acids such as DHA and EPA have a significant potential of being functional fatty acids for preventing myocardial infarction, psoriasis, bronchial asthma, and other diseases. The PUFA analysis of lipids has provided fundamental information for evaluating these functional lipids for understanding the human metabolism.
Structure lipids with different positional distributions of PUFA in acylglycerol are also needed in order to identify the health benefits of the lipid. However, no single and simple method has been completely established to analyze the triacylglycerol molecular species of the marine lipid. The authors have developed a new standard method for DHA analysis by NMR. The DHA content and relative quantification of the n-3 fatty acids in the marine lipid were accurately and rapidly obtained using 300-500 MHz proton NMR.
Recent interests have been summarized as the health benefits since it has been recognized that there are many difficulties in the analysis of geometric and positional isomers of conjugated linoleic acid. Furthermore, in the field of fish oil utilization, the undesirable flavor of the product should be restricted to prevent odors as reversed grassy smell from PUFA. Analysis of fish flavor was examined by the method of solid phase micro extraction (SPME) for identifying flavor compounds from oxidized fish oil by heating with micro oven and other conditions.
For the utilization of fish oil after getting the precise analysis of PUFA, how to prevent the oxidation is important. Inositol hexaphosphate as one of the natural antioxidants has the potential for the preventing of fish oil oxidation.
Lipid analysis should be undertaken with the methods of non-destructive and observational analyses in the new millennium. The future trends of lipid analysis might include the key words of rapid, accurate, less solvent, and non-destructive instrumentation.
J. Oleo Sci. 50, 329-338 (2001).

Analysis of Dietary Trans Fatty Acids,
W.M.N. RATNAYAKE,
Nutrition Research Division, Food Directorate, Health Products and Food Branch, Health Canada, Banting Building, Postal Locator 2203C, Ottawa, Ontario, Canada K1A 0L2.
In partially hydrogenated vegetable oils (PHVO) more than 40 cis and trans fatty acids, primarily of the C₁₈ chain length are possible. Partially hydrogenated fish oils (PHFO), invariably have much more complex fatty acid profiles because of the large number of possible isomers of the chain lengths ranging from C₁₆ to C₂₂. Traditionally, total trans content was determined by infrared (IR) spectroscopic techniques that do not quantify individual fatty acids. Nowadays, a satisfactory, and near quantitative analysis of fatty acid profile of PHVO can be achieved by gas chromatography (GC) using 100 m long capillary columns coated with highly polar cyanolsilicone stationary phases. In these columns, there is very little overlap of cis and trans isomers. Almost all the cyanosilicone capillary columns are capable of readily separating the low delta value trans 18:1 isomers (up to and including 12t-18:1) from the cis-18:1 isomers. If appropriate GC operating conditions are selected, then some cyanosilicone columns, especially, SP-2560 and CP-Sil 88, could provide a satisfactory separation of the high delta isomers (13t-18:1, 14t-18:1 and 16t-18:1) from the cis isomers. The 15t-18:1 is the only isomer that cannot be separated from the cis isomers. The geometric and positional isomers of linoleic and a-linolenic acids that are normally encountered in dietary fats could also be easily separated on cyanosilicone capillary columns. For applications requiring more precise trans fatty acid data and detailed information of individual isomers, it is necessary to couple capillary GC analysis with either silver nitrate-thin-layer or -high pressure liquid chromatography.
J. Oleo Sci. 50, 339-352 (2001).

Current and Future Innovations in Soybean (Glycine max L. Merr.) Oil Composition,
R.F. WILSON¹, J.W. BURTON¹, W.P. NOVITZKY¹ and R.E. DEWEY²,
¹: USDA-ARS, North Carolina State University, 2: Crop Science Department, North Carolina State University, 100 Derieux St., Raleigh, North Carolina 27695-7620, USA.
Biotechnology often is regarded strictly as transgenic research. In practice, it involves a team effort among plant breeders, genomicists, and molecular geneticists. Genetic improvement of soybean (Glycine max) began over 5000 years ago when wild soybeans (Glycine soja) were introduced into China. These ancestors of cultivated soybean exhibit a wide range of genetic diversity for traits that range from seed size and color to genes that govern oil composition. However, the 'gene pool' for US varieties comes from less than 12 of the 18000 types of Glycine max. Thus, the genetic base for modern soybeans is rather narrow. For example, wild soybeans contain desaturase genes (FAD3) are not present in domesticated soybean that contribute to elevated polyunsaturates in Glycine max. How can we extract and utilize untapped genetic diversity in soybean or any other crop? The answer is through biotechnology. Soybean breeders have an arsenal of natural gene mutations (recessive alleles) that influence fatty acid composition. Modern genetic technology helps identify the gene, gene product and the exact nature of the mutation in each allele. Transgenic research provides 'proof of concept' and also may be used to create genetic diversity for novel traits. Gene markers, maps and micro-array technology help to locate selected genes in segregating populations. These tools accelerate breeding progress and enable variety development in a socially acceptable manner. These concepts are applied to the development of agronomic soybeans with lower-palmitic acid, higher oleic acid and lower-linolenic acid concentration. In the near future, the means to create natural mutations that fine-tune regulation of metabolic enzyme activities for specific traits will be in hand. Such technical advances may lessen social concern for biotechnology, through more effective use of natural genetic diversity to achieve goals now thought possible only by application of transgenes in commercial food/feed products.
J. Oleo Sci. 50, 353-358 (2001).

Production of Polyunsaturated Fatty Acids by Genetic Engineering of Yeast,
Y. MICHINAKA¹, T. AKI¹, K. INAGAKI¹, H. HIGASHIMOTO¹, Y. SHIMADA¹, T. NAKAJIMA², T. SHIMAUCHI², K. ONO¹ and O. SUZUKI¹,
1:Department of Molecular Biotechnology, Graduate School of Advanced Sciences of Matter, Hiroshima University, Higashi-Hiroshima, JAPAN and ²:Technical Center, Idemitsu Technofine Co. Ltd., Tokyo, JAPAN.
In order to study the production system of polyunsaturated fatty acids (PUFA), we genetically engineered a baker's yeast that did not originally produce PUFA. We produced g-linolenic acid (GLA) by constructing a heterologous system to express D6 fatty acid desaturase (D6d) gene from rat liver into yeast, Saccharomyces cerevisiae. The expression of this gene in the presence of linoleic acid (LA) formed a significant amount of GLA in the host cells. In order to effect the largest expression of the conversion rate from LA to GLA, we set up a dual promoter system, where genes coding for the D6d and an electron donor protein, cytochrome b₅, were coordinately expressed. The desaturation index (GLA/LA) increased significantly by high level expression of cytochrome b₅, indicating that this protein is a limiting factor in regular yeast. In addition, we examined a condition for the extra-cellular production of GLA by a fatty acid secretion yeast mutant. By expressing the D6d gene under the control of GAP-DH promoter in the presence of LA, 178 mg/L of GLA was secreted in the medium in 144 h.
J. Oleo Sci. 50, 359-365 (2001).

Trends and Technological Developments in Laundry Products in Japan,
M. TSUMADORI,
Household Products Research Laboratories, Kao, Corporation, 1334 Minato, Wakayama 640-8580, JAPAN.
Since launching the first compact powder detergent that had a dosage of 25 grams/30 liters, sales of these compact powders have taken over conventional powders and liquids. In the middle of 1990s have seen a further progress in compaction. At present ultra-compact detergents, having a dosage of 20 g/30 L and 15 g/30 L, have captured a dominant market share.
The spreading of compact and/or ultra-compact detergents has led to a change in consumption of surfactants. Although LAS is still a main ingredient for compact powders, alcohol ethoxylates and a-sulfo fatty acid esters have gained a stronger position in surfactant markets.
Other recent developments and trends include detergents formulated with bleach employing various types of bleach activators, which meet hygiene requirements and bleaching performance. Also, in 2000, tablet detergents and sheet type detergent have also been introduced into the Japanese market.
In the fabric softener market, concentrated products are gradually becoming dominant. Most of them are sold in eco-type packages, which make a significant contribution to save resources. As well, a readily biodegradable softening agent has been employed as a main ingredient in Japan.
Another exciting major innovation has been seen in bleach. Since 1990, the use of liquid oxygen bleach has been increasing steadily. In 1996, the first liquid oxygen bleach, formulated with a long alkyl chain activator satisfying both superb bleaching performance and activator stability, was launched. It has gained a strong position in the market.
J. Oleo Sci. 50, 367-372 (2001).

The Significance of Alpha-linolenic Acid for Humans,
A.J. SINCLAIR and D. LI,
Department of Food Science, RMIT University, Victoria 3001, AUSTRALIA.
The omega 3 polyunsaturated fatty acids have had a major impact on thinking in medicine in the last twenty-five years. The parent fatty acid in the omega 3 fatty acid family is alpha-linolenic acid (ALA) which is an essential fatty acid found in high concentrations in certain plant oils, such as flaxseed oil, walnut oil and canola oil. Several longer chain or derived omega 3 fatty acids are formed in the body from ALA, including eicosapentaenoic acid, EPA, docosapentaenoic acid and docosahexaenoic acid, DHA. Dietary sources of these longer-chain fatty acids are fish, fish oils and from other marine organisms. DHA is specifically localised in the retina and the brain in humans and other mammals where it has a primary role via effects on membrane order (fluidity), the activity of membrane-bound enzymes, ion channels and signal transduction.
For many years, ALA has been considered to be important only as a precursor of these longer chain compounds, however it is now recognised that ALA is metabolised by other pathways which may be quantitatively more important than the formation of DHA. For example, ALA is extensively b-oxidised in mammals including humans, especially on diets rich in polyunsaturated fatty acids. ALA appears to play an important role in the nervous system (carbon recycling) for the synthesis of saturated and monounsaturated fatty acids and cholesterol, with estimates of the proportion of ALA being metabolised via this pathway being several fold greater than that to DHA. Furthermore, recent studies have indicated that ALA is deposited in the skin of small mammals and may also play a role in fur. Since ALA is extensively metabolised via these pathways (b-oxidation, carbon recycling and deposition in skin/fur) and is subject to competitive inhibition from linoleic acid in metabolism via the delta-6 desaturase, it is not surprising that dietary DHA is substantially more effective than an equivalent dose of dietary ALA in maintaining neural DHA levels. Despite the limited efficiency of DHA formation from ALA, it is clear that certain tissues possess the capacity to synthesise DHA at rates greater than other tissues. The brain, retina and reproductive tissue may be able to synthesise sufficient DHA to meet the DHA demands of these tissues, although in infants at the peak of brain growth and DHA deposition, a dietary supply of DHA (as in milk) may be important to maintain the brain DHA level. In plants, ALA is a substrate for lipoxygenase enzymes leading to the production of bioactive hydroxy compounds. This information might provide a clue to other routes of ALA metabolism in mammals. It is concluded that it may no longer be appropriate to consider the function for ALA to be solely a precursor of EPA and DHA.
J. Oleo Sci. 50, 373-379 (2001).

Synaptic Aging and Carnitine,
S. ANDO¹, Y. TANAKA¹, H. WAKI¹, F. FUKUI¹ and T. KAWABATA²,
¹: Tokyo Metropolitan Institute of Gerontology, 35-2 Sakaecho, Itabashi-ku, Tokyo 173-0015, JAPAN, ²: Faculty of Nutrition, Kagawa Nutrition University, 3-9-21 Chiyoda, Sakado-shi, Saitama 350-0288, JAPAN.
Age-related changes in neuronal functions were examined in terms of cholinergic synaptic transmission as an initial step. The synthetic capacity of acetylcholine was found to remain unchanged during the lifespan of mouse. This finding has revised the existing concept that acetylcholine synthesis is decreased in aging. The present study has revealed that the density of voltage-dependent calcium channels in synaptic plasma membranes is decreased to reduce Ca²⁺ influx into synapses, resulting in the decreased release of acetylcholine.
The hypofunction of cholinergic synapses occurring in aging was attempted to be restored in the second place. Sialic acid-containg compounds including gangliosides and synthetic ganglioside analogues were found to facilitate the acetylcholine release by increasing Ca²⁺ influx or choline uptake. On the other hand, acetyl-L-carnitine was shown to serve as a donor of acetyl residues to increase acetylcholine synthesis. This carnitine derivative may be a good candidate for an enhancer of cholinergic transmission and for anti-brain aging supplement.
J. Oleo Sci. 50, 381-385 (2001).

Interfacial Lipid Oxidation and Antioxidation,
E.N. FRANKEL,
Department of Food Science and Technology, University of California, Davis, CA 95616, USA.
Lipid oxidation is not well understood in systems in which the fat is dispersed in emulsion systems. Interfacial oxidation is a "surface" reaction dependent on the rate of oxygen diffusion and its interactions with unsaturated lipids, metal initiators, radical generators and antioxidants, which are distributed in different compartments of colloidal systems. This interfacial oxidation affects a large number of foods, which exist in the form of emulsions. The classical mechanism of inhibited lipid oxidation does not predict the changes in antioxidant effectiveness between solutions and emulsion systems.
In multiphase systems antioxidants partition between the aqueous phase, lipid phase and surfactant-enriched environment. This partition of antioxidants in different phases changes their activity in food and biological systems. In these multiphase systems antioxidant effectiveness is determined by the heterogeneity and heterophasic nature of the system, the localization of antioxidants in different phases, the colloidal properties of the substrates, the conditions of oxidation, and the stages of oxidation, the type and physicochemical state of the lipid substrate and its degree of unsaturation, the presence and types of initiators, such as transition metals, other components, and their possible interaction. Antioxidant activity is thus strongly affected by the physical composition of the test system, and the relative activity of antioxidants of different polarity varies significantly in different multiphase systems. For these reasons there cannot be a simple and rapid method to evaluate antioxidants in complex foods and biological systems. Valid methods require the use of more than one condition of oxidation and more than one specific method to determine lipid oxidation.
J. Oleo Sci. 50, 387-391 (2001).

Factors Affecting the Oxidative Stability of Emulsified Oil and Membranous Phospholipids,
J. TERANO,
Department of Nutrition, School of Medicine, The University of Tokushima, Kuramoto-cho 3, Tokushima 770-8503, JAPAN.
A number of factors affect the progress of lipid peroxidation and thereby oxidative stability of individual foods varies widely. Here we discussed on lipid peroxidation in triacylglycerol in emulsion and phospholipid in lamellar structure. First, we pointed out that plant-derived polyphenols act as powerful antioxidants in these heterogeneous systems because of their unique localization between water phase and lipid phase. Second, it was clarified that lipase-hydrolysis is a useful tool to elevate the stability of fish oil emulsion against lipid peroxidation. This is definitely due to the release of peroxidation-resistant free polyunsaturated fatty acids from triacylglycerol assembly. Third, phosphatidylserine was found to effectively inhibit iron-ion-induced lipid peroxidation of egg yolk PC in lamellar structure, indicating that incorporation of phosphoserine group into lamellar structure is helpful to enhance the oxidative stability of food lipids. Finally, the oxidizability of docosahexaenoic acid-containing phospholipids is not necessary high in free radical oxidation occurring in lamellar structure.
J. Oleo Sci. 50, 393-397 (2001).

The Proper Balance of Essential Fatty Acids for Life,
E.L. LIEN, K. STEINER and J.C. WALLINGFORD,
Wyeth Nutritionals International, P.O. Box 42528 Philadelphia., PA 19101, USA.
It has been known for more than 70 years that some fatty acids are essential in the diet, but quantitative requirements for n-3 and n-6 fatty acids have been difficult to define. Recent research has established the importance of n-3 and n-6 long chain polyunsaturated fatty acids (LCPs) during infancy. Since n-6 and n-3 fatty acids compete for elongation and desaturation to biologically active LCPs that may have opposing biological effects, awareness of the n-3/n-6 balance is critical.
Requirements for LCPs in infancy have been empirically determined by comparing formula-fed to breast fed infants. The composition of human milk, and the biochemical, metabolic and behavioral responses of the breast-fed infant serve as guides to the requirements for LCPs. While n-6 LCP levels in human milk are rather constant on a global basis, the concentrations of n-3 LCPs in human milk vary widely. A balanced addition of LCPs to infant formula improves visual acuity, cognitive development, modifies the immune response, and modulates cholesterol metabolism all to more closely resemble breast-fed infants. Unbalanced additions (n-3 LCPs with no n-6 LCPs), however, have been associated with impaired language development in males and decreased growth in low body weight (LBW) infants. Benefits of LCP supplementation extend beyond the first 6 months of life.
Little is known about the optimal n-3/n-6 balance after weaning and in puberty, when nutrient demands dramatically increase to support growth and development. However, efforts to modify total and saturated fat intake, to prevent the beginnings of some adult diseases, have drawn attention to the importance of fatty acid balance in childhood.
Unbalanced consumption of n-3 and n-6 fatty acids is associated with many different diseases in adulthood ; n-3 LCP supplementation is linked to a decrease in the risk of hypertension, mental diseases, immune hyper-reactivity, and heart disease. Even small amounts of n-3 LCPs in the diet have been associated with reduced risk of sudden cardiac death, probably due to their anti-arrhythmic effects. In vivo studies have shown that LCPs prevent arrhythmias and modify heart rate variability. In cultured cardiac myocytes LCPs interact directly with ion channels to protect against arrhythmic responses.
Prospective, properly controlled studies need to be conducted to further define the role of the n-3/n-6 ratio in adolescent and adult life. By integrating our knowledge of LCP balance in infancy with current and future information concerning requirements later in life, we will be able to establish appropriate balance recommendations for optimal balance throughout a lifetime.
J. Oleo Sci. 50, 399-405 (2001).

Size-dependent Thermosensitivity of Poly (N-isopropylacrylamide-co-acrylic acid) Hydrogel Microspheres Prepared by a Membrane Emulsification Method : Phase Transition Temperature Changes Depending on the Hydrogel Size,
K. MAKINO,
Faculty of Pharmaceutical Sciences and Institute of Colloid and Interface Science, Science University of Tokyo, 12 Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, JAPAN.
Changes in the surface properties of poly (N-isopropylacrylamide-co-5 mol% acrylic acid) microspheres depending on temperature and the size of the microspheres were studied by measuring the electrophoretic mobility of the microspheres in electrolyte solutions at pH 7.4 at 25, 30, 33, 35, 40, and 45°C. The hydrogel microspheres were monodisperse, since they were prepared from w/o emulsion using a membrane emulsification method. The size of the microspheres was dependent on the membrane pore size of the membrane. Membranes with four pore sizes were used. Poly (N-isopropylacrylamide-co-5 mol% acrylic acid) microspheres have shown negative electrophoretic mobility values. More negative values were obtained with the smaller microspheres than the larger ones at each temperature. The surface became harder as temperature rose, independent of the microsphere size. This is caused by the shrinkage of poly (N-isopropylacrylamide) moiety, LCST of which is 33°C. It has been newly found that the smaller microspheres have a lower phase transition temperature (LCST) and exhibit the stronger dependence of surface charge density on the temperature than the larger ones. The surface charge density of the microspheres became higher only in the small microspheres as temperature rose, and it changed little in larger microspheres. That is, in the case of poly (N-isopropylacrylamide-co-5 mol% acrylic acid) hydrogels, thermosensitive changes of their surface structures are dependent on their size, because the heterogeneity of the microsphere structural is different depending on their sizes. These observations suggest that the changes in structural heterogeneity of poly (N-isopropylacrylamide-co-5 mol% acrylic acid) microgels affect their LCST and that the heterogeneous gel structure of microgels strongly affects their surface properties as comparing with those of bulk gels.
J. Oleo Sci. 50, 407-413 (2001).

Alternative Diesel Fuels from Vegetable Oils and Animal Fats,
R. O. DUNN and G. KNOTHE,
Oil Chemical Research, U.S. Department of Agriculture (USDA), Agricultural Research Service (ARS), National Center for Agricultural Utilization Research (NCAUR), 1815 N. University St., Peoria, IL, 61604, USA.
Biodiesel, defined as the mono-alkyl esters of fatty acids derived from vegetable oils or animal fats, is a strong candidate alternative fuel for combustion in compression ignition (diesel) engines. With respect to petroleum middle distillates, biodiesel has superior cetane number and lubricity characteristics, has comparable heats of combustion and kinematic viscosities, and is non-flammable making it safer to store and handle. Biodiesel is renewable and can help reduce dependence upon imported petroleum. Biodiesel is environmentally friendly because it is readily biodegradable and its combustion reduces most harmful exhaust emissions, including carbon monoxide, unburned hydrocarbons, particulate matter, and polyaromatic hydrocarbons. In the United States, the Energy Policy Act (EPACT) of 1992 and Clean Air Act with its subsequent amendments have combined to help establish a favorable atmosphere for development of biodiesel ; however, many technological hurdles must be removed before widespread commercialization will be feasible. During cooler weather, biodiesel "gels" at temperatures near freezing (0°C) compared with -15 to-17°C for conventional diesel fuel. Another concern for biodiesel is its long-term storage stability with respect to oxidative degradation. Finally, most reports indicate biodiesel does not significantly reduce nitrogen oxides (NO_x) emissions. This is a particular concern because NO_x may react in the atmosphere to form ozone, a component of smog. This work reviews recent progress in the development of biodiesel with emphasis on removing these technological hurdles.
J. Oleo Sci. 50, 415-426 (2001).

Nutritional Functions of Dietary Diacylglycerols,
T. YASUKAWA and K. YASUNAGA,
Health Care Products Research Lab. No.1, Kao Corporation, 2-1-3 Bunka, Sumida-ku, Tokyo 131-8501, JAPAN.
We have investigated the nutritional and metabolic functions of dietary diacylglycerol and found that it has various beneficial effects for the human health when used as edible oils. We manufactured diacylglycerol-rich oil (DAG) containing more than 80 wt% of diacylglycerol by using the immobilized-lipase. We also prepared a control triacylglycerol oil (TAG) which has the comparable fatty acid composition with DAG. The metabolic characteristics of DAG compared with TAG are likely to be based upon its chemical structure since the energy values and absorption coefficients of both oils are similar.
The results of clinical studies using DAG are as follows :
1. DAG lowered the magnitude of postprandial increase in serum and chylomicron triacylglycerol (TG) levels as compared with TAG in the single administration study in humans.
2. DAG prevented body fat accumulation, especially in visceral fat as measured by CT scan, in double-blind controlled study (DAG and TAG group of 19 subjects each, 16 wks).
3. The serum profiles (hige density lipoprotein (HDL), TG and plasminogen activator inhibitor type-1) and anthropometric parameters (weight, body mass index, waist circumference and thickness of subcutaneous fat) were obviously improved by consuming DAG designed as cooking oil in free-living subjects (114 subjects,1 yr).
From these findings, DAG was considered to be effective in preventing obesity and to possibly prevent the life-style related diseases only by consuming as a daily cooking oil.
J. Oleo Sci. 50, 427-432 (2001).

Fats and Oils as Oleochemical Raw Materials,
K. HILL,
Cognis Deutschland GmbH,Care Chemicals, Postfach 130164, 40551 Düsseldorf, GERMANY.
Vegetable oils and fats are important constituents of human and animal foodstuffs. Certain grades are industrially used and together with carbohydrates (cellulose, starch, saccharose from wood, grain, sugar cane and sugar beet) and proteins from a vegetable or animal source they are numbered among the renewable resources compared to fossil and mineral raw materials whose occurrence is limited and finite.
In concepts for new products the price, performance and product safety criteria are equally important and have a correspondingly high importance right at the start of product development. To ensure a high degree of product safety for consumers and the environment renewable resources have often been shown to have advantages when compared with petrochemical raw materials and can therefore be regarded as being the ideal raw material basis for many applications. Results from oleochemistry show that the use of vegetable fats and oils allows the development of competitive, powerful products and product concepts which are both consumer-friendly and environmentally-friendly.
Recent products which fit this requirement profile are the anionic surfactants cocomonoglyceride sulfate and protein-fatty acid condensate and the nonionic sugar surfactant alkyl polyglycoside from glucose and fatty alcohol. These products are used in washing and cleansing agents, as mild surfactants in cosmetic formulations as well as dispersing aids for technical applications. For personal care applications long chain alkyl polyglycosides or composites of special glycerides and alkylpolyglycosides were shown to be interesting emulsifiers and lipid layer enhancers. New emollients for light emulsions have been developed based on fatty alcohols, e.g. dialkyl ethers and dialkyl carbonates.
In polymer applications derivatives of oils and fats, such as epoxides, polyols and dimerizations products based on unsaturated fatty acids, are used as plastic additives or components for composites or polymers like polyamides and polyurethanes. In the lubricant sector oleochemically-based fatty acid esters have proved to be powerful alternatives to conventional mineral oil products.
J. Oleo Sci. 50, 433-444 (2001).

Fatty Acid Methyl Ester and Its Relative Products from Palm Oil,
M. NAKAMURA,
Sakaide Factory, Lion Oleochemical Co. LTD., 22-1 Bannosucho, Sakaide city, Kagawa 762-0064, JAPAN.
There has been a tendency towards a gradual changing of raw materials in the detergent industry from petrochemicals to vegetable oils. One major advantage of vegetable oils is that they are renewable resources and friendly to the environment.
Palm oil has been worthy of special attention because of satisfactory yields and suitable carbon chain distributions for various kinds of surfactants such as alpha sulfo fatty acid methyl ester (MES), and so on. Another advantage of palm oil is that crude palm oil contains useful minor components.
Specifically, palm carotene has attracted the attention of many researchers, because which is composed of carotene isomers and which content is about 10 times higher than that of carrots.
Generally, most oleochemical products are produced through fatty acid or fatty acid methylester. Fatty acid is still a major oleochemical product, however the growth of production amounts of fatty acid methylester is greater than that of fatty acid from a view point of energy consumption.
In this paper, new oleochemical streams based on fatty acid methylester derived from palm oil are discussed. These methylesters are raw materials for various surfactants, such as MES, soap, alcohol sulfate, alcohol ethoxylate, cationic surfactant and so on.
Besides the extraction process of natural carotenes from palm oil, using a phase equilibrium of palm methylester, methanol, and water, has been commercially successful.
Palm oil, palm kernel oil, and coconuts oil will play important roles in the 21st centuries.
J. Oleo Sci. 50, 445-452 (2001).

Specific Surface Activity of Gemini Surfactants : Mixing Effects of Alanine-type and Sulfate-type Surfactants,
K. TAJIMA¹, Y. IMAI¹, A. NAKAMURA², K. TSUBONE³, K. MIURA³, Y. NAKATSUJI and I. IKEDA⁴,
¹: Dept. Chem., Kanagawa Univ., 3-27 Rokkakubashi, Yokohama, 221-8686, JAPAN, ²: School Design Arch., Nagoya City Univ., 2-1 Kitachikusa, Nagoya, 464-0083, JAPAN, ³: Kanebo Cosmetics Laboratory, 5-3-28 Kotobukityo Odawara, 250-0002, JAPAN and ⁴: Dept. Applied Chem., Osaka Univ., 2-1 Yamadaoka, Suita, Osaka, 565-0871, JAPAN.
This paper has described the surface chemical properties of the three kinds of Gemini surfactants from points of views of the specific surface activity and the polar moiety interactions. The specific surface activity named "Gemini effect" was defined as the ratio of surface activity of Gemini surfactant to that of the single chain surfactant with a similar molecular structure. The Gemini effects were compared among three kinds of Gemini surfactants as a function of their interchain-spacer distances. The interactions between sulfate groups and alanine groups in the mixture of Gemini and single-chain surfactants were investigated on the basis of the compositions of the adsorbed monolayer and micelles as mixing effects.
J. Oleo Sci. 50, 453-462 (2001).