Bressmer & Francke (GmbH & Co.) KG Competence in Vegetable Oils & Fats, Cereals Phone: 0049 89 05 86 0 Fax: 0049 89 05 86 99 E-mail: info@bressmer-oils.eu Gutenbergring 37, 22848 Norderstedt 1
Fat and fatty acids fatty acid G L Y C fatty acid Fats are build by 1 molecule glycerin and 3 fatty acids E R I fatty acid N • Fatty acids are divided into saturated fatty acids and unsaturated fatty acids. • There are monounsaturated and polyunsaturated fatty acids. • There are three types of (polyunsaturated) Omega-fatty-acids : Omega-9-fatty acids, e.g. oleic acid Omega-6-fatty acids, e.g. linoleic acid Omega-3-fatty acids, e.g. α -linolenic acid 2
Protective effects of Omega-3-fatty acids Numerous clinical studies show: Omega-3-fatty acids have effects on • Allergy • Neurodermitis • Inflammation Eicosanoids are responsible for these effects. Eicosanoids are build by human from Omega-3 fatty acids. 3
Protective effects of Omega-3-fatty acids Brain • By increasing circulation of the blood the brain will better oxygenated. • Efficiency will increase. Cholesterol Omega-3-fatty acids regulate: The ratio will improve between the “bad“ LDL-cholesterol and the “good“ HDL-cholesterol. 4
Health protection through Omega-3-acids Omega-3-fatty acids are protective and stimulate Health Promoting • Intelligence Work • Good vision • for pre-natal care • Stress resistance Decreasing the risk • Depression • Aggression • Stress • Coronary heart diseases Decreasing the risk • Dementia • Alzheimer 5
Omega fatty acids The Omega fatty acids are important for the development and the function of the human body. α -linolenic acid ( Omega-3 ) and linoleic acid ( Omega-6 ) are the two “basic” Omega fatty acids • There are so called “long chain” Omega fatty acids: EPA (eicosapentaenic acid), Omega-3 DHA (docosahexaenic acid), Omega-3 ARA (arachidonic acid), Omega-6 The essential fatty acids cannot be made in the body and so they have to be included in the food. 6
Omega-3 (α -linolenic acid) 1 5 12 9 O H 3 C-CH 2 -CH=CH-CH 2 -CH=CH-CH 2 -CH 2 =CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -C OH α -linolenic acid (C18:3) • Essential fatty acid. • „Basic-Omega-3-fatty acid“: • Formation of EPA and DHA from α -linolenic acid. • Formation of EPA & DHA is inhibited by excess of linoleic acid. • Best source: flaxseed . Omega-3-Concentrate (Flax) 3-Cereals-Omega-Oil Rapeseed Oil Soybean Oil Saflor Oil Sunflower Oil α -linolenic acid content of vegetable oils Olive Oil 0% 20% 40% 60% 80% 7
Omega-6 (linoleic acid) O 1 2 9 H 3 C-CH 2 -CH-CH-CH 2 -CH=CH-CH 2 -CH 2 =CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -C OH linoleic acid (C18:2) • Essential fatty acid. • „Basic-Omega-6-fatty acid“: • Formation of arachidonic acid (AA) from linoleic acid. • Formation of EPA & DHA is inhibited by excess of linoleic acid. • Widespread in vegetable oils, especially in sunflower oil. Omega-3-Concentrate (Flax) 3-Cereals-Omega-Oil Rapeseed Oil Soybean Oil Saflor Oil Sunflower Oil linoleic acid content of vegetable oils Olive Oil 0% 20% 40% 60% 80% 8
α -linolenic acid (ALA) – the essential vegetable Omega-3 Scientific background and benefits in food
α -linolenic acid 12 11 16 15 9 13 10 14 C 17 H 3 18 7 α -linolenic acid (ALA) 8 6 5 O 3 4 •ALA is an Omega-3 (n-3) fatty acid 2 1 •It is a “short-chain” n-3 fatty acid. O H •ALA is the only essential Omega-3 fatty acid. H 3 C eicosapentaenic acid (EPA) O H 3 C OH docosahexaenic acid (DHA) O OH 10
metabolism of α -linolenic acid ALA intake >96% absorbed ALA 15 - 33% 8 - 22% 45 - 77 % desaturation & „stable“ β -oxidation elongation ALA-lipids CO 2 lcPUFA SFA, MUFA 11
Conversion of ALA to longer chain PUFA ALA is converted to EPA by several enzymes α - linolenic acid (C18:3n-3) ∆ -6-desaturase (C18:4n-3) elongase (C20:4n-3) ∆ -5-desaturase eicosapentaenic acid Eicosanoides: (C20:5n-3) – thromboxanes – leucotrienes – prostaglandines •Important eicosanoides are build from EPA • ∆ -6-desaturase is the rate limiting enzyme synthesis of EPA from ALA is regulated by the body 12
Conversion of ALA to longer chain PUFA DHA-synthesis from EPA α - linolenic acid (C18:3n-3) ∆ -6-desaturase (C18:4n-3) elongase (C20:4n-3) ∆ -5-desaturase eicosapentaenic acid (C20:5n-3) elongase (C22:5n-3) elongase Endoplasmatic (C24:5n-3) ∆ -6-desaturase reticulum (C24:6n-3) translocation β -oxidation docosahexaenic acid Peroxisome (C22:6n-3) 13
Conversion of ALA to long-chain PUFA α -linolenic acid and linoleic acid (LA) compete for the same enzymes α - linolenic acid linoleic acid (C18:2n-6) (C18:3n-3) ∆ -6-desaturase γ - linolenic acid (C18:4n-3) elongase (C20:3n-6) (C20:4n-3) ∆ -5-desaturase arachidonic acid eicosapentaenic acid (AA) (C20:4n-6) (C20:5n-3) EPA and AA are antagonists The right ratio between EPA and AA is most important The ratio LA:ALA determines the ratio AA:EPA that is built from LA & ALA. 14
The Omega balance Usually LA (Omega-6) dominates in in our nutrition leading to a surplus of arachidonic acid! Ω - 3 Ω - 6 15
The Omega balance Reasonable supply of EPA/DHA cannot reduce the surplus of arachidonic acid (AA)! Ω - 3 Ω - 6 16
The Omega balance α -linolenic acid and linoleic acid compete for the same enzymes: Sufficient intake of α -linolenic acid will: • reduce production of AA and • increase production of EPA & DHA. Ω - 3 Ω - 6 17
Is the efficiency of conversion (8-22%) to lcPUFAs really poor ?
A view to the conversion rate The limiting factor for building EPA is the ∆ -6-desaturase! Studies show: Supplementation with EPA/DHA downregulates lcPUFA syntheses. Conclusions: • The body limits the lcPUFAs to a reasonable level. • EPA/DHA can be overdosed. • Everybody is unique: it is hard to find the individually right dosage. • Excessive intake of EPA and DHA may injure the immune system, increase the risk of bloodshot and increase the risk of oxidative cell damages. • EPA supplementation can result in a lack of AA. • One can synthesise enough EPA (if LA:ALA ratio is balanced). 19
A view to the conversion rate • Earlier studies supposed that DHA is not synthesised from ALA. This is disproved! • The body can regulate DHA production. • In pregnancy and lactation DHA production is significantly increased: even the requirements for the developing foetal brain can be met by ALA. • Latest scientific finding: foetuses have the capacity to convert ALA to DHA in liver. DHA requirement can be met by sufficient ALA intake 20
Is the efficiency of conversion (8-22%) to lcPUFAs really poor ? It is adequate if the nutritional requirements are fulfilled!
Metabolism of α -linolenic acid ALA intake >96% absorbed ALA 45 - 77 % 15 - 33% 8 - 22% desaturation & „stable“ β -oxidation elongation ALA-lipids CO 2 lcPUFA SFA, MUFA 22
“Stable” ALA lipids “stable” lipids: triacyl glycerols, phospholipids, cholesteryl esters .... Effects of ALA “itself”: • ALA is an important structure component of cell membranes. • ALA is involved with skin and hair function. • ALA has functions of its own in relation to the cardiovascular system and neural function. • ALA increases immune function. • ALA improves insulin sensitivity. ALA cannot be replaced by EPA/DHA 23
α -linolenic acid in nutrition Edible wild plants provide ALA in higher amounts than cultivated plants! Human beings evolved a nutrition balanced in the Omega-6 and Omega-3. LA:ALA 1 : 1 5 : 1 20 : 1 Primitive man 17th cent. today We changed our diet from about 10,000 years ago and accelerated this change about 200 years. 24
Recommendations on nutrition Total fat intake •20 - 35 % of total energy intake Saturated fat •max. 1/3 of total fat intake Polyunsaturated fatty acids •limited intake of linoleic acid •long chain Omega fatty acids max 10% of total Omega fatty acids •increasing the α -linolenic acid intake Recommended Omega-6 to Omega-3 ratio is 5 : 1 (DACH Reference) DACH-Reference Average consumption 0% 20% 40% 60% 80% 100% Omega-3 Omega-6 monounsaturated saturated 25
Sources of α -linolenic acid • Edible wild berries and herbs • Walnuts (35% LA + 9% ALA) • Vegetable oils rapeseed oil perilla oil linseed oil 26
Sources of α -linolenic acid Rapeseed oil • Average content of LA: 25% ALA: 9% insufficient ALA for supplementing suitable edible oil for daily cooking alpha-linolenic acid (O-3) linoleic acid (O-6) monounsat. fatty acid sat. fatty acid 27
Sources of α -linolenic acid Perilla oil (Perilla fructescens) • High content of ALA (app. 58%) • Perilla aldehyde is allergenic • some of the ketones are pneumotoxic alpha-linolenic acid (O-3) linoleic acid (O-6) monounsat. fatty acid sat. fatty acid 28
Sources of α -linolenic acid linseed oil • Average content of LA: 13%, ALA: 58% • Highest ratio LA:ALA (1:4.5) • not stable • bitter and toxic substances (cyanogenic glucosides) alpha-linolenic acid (O-3) linoleic acid (O-6) monounsat. fatty acid sat. fatty acid 29
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