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(12) Patent Application Publication (10) Pub. No.: US 2006/0172023 A1 Heimerikx Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2006/0172023 A1 Heimerikx Et Al US 2006O172023A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2006/0172023 A1 Heimerikx et al. (43) Pub. Date: Aug. 3, 2006 (54) USE OF PINOLENIC ACID (30) Foreign Application Priority Data (75) Inventors: Jos Heimerikx, Vormerveer (NL); Jan. 31, 2005 (EP)........................................ O5250517.9 Ulrike Schmid, Wormerveer (NL); Jul. 14, 2005 (GB)......................................... O514463.9 Alexandra Einerhand, Wormerveer Publication Classification (NL); Wiro Stam, Wormerveer (NL); Luisa Gambelli, Wormerveer (NL) (51) Int. Cl. A6IR 36/3 (2006.01) A6II 3L/22 (2006.01) Correspondence Address: A6II 3L/202 (2006.01) MORGAN LEWIS & BOCKUS LLP (52) U.S. Cl. ........................... 424/770; 514/547: 514/560 1111 PENNSYLVANIAAVENUE NW WASHINGTON, DC 20004 (US) (57) ABSTRACT Method of managing weight by administering a composition including pinolenic acid or derivative such as a glyceride (73) Assignee: LODERS CROKLAAN B.V., Worm thereof. The composition may be pine nut oil or a derivative erveer (NL) thereof and may be used as a food Supplement or food product such as margarine or as a pharmaceutical compo (21) Appl. No.: 11/341,517 sition, e.g. in tablet form. The composition may also include other components such as linoleic acid or other fatty acid or (22) Filed: Jan. 30, 2006 derivative thereof. Patent Application Publication Aug. 3, 2006 Sheet 1 of 5 US 2006/0172023 A1 rN N NYN NYNY. A NYNYNYNYNYNY- - % NYS NYNYSYNYSYNY % NNNNN & R | | | RNNN NYN NNN & % H - 8. SYNYNYNYNYNYNYNY YNYNYNYNYN NYNYNYS NYNNYNYNYNY % NYNYSYNYN 6 N & & N NYNYNY % - NSN -& % SYNYNY *% NY & s 3 3 3 s O Patent Application Publication Aug. 3, 2006 Sheet 2 of 5 US 2006/0172023 A1 O 30 60 90 120 180 240 O 30 60 90 120 180 240 Patent Application Publication Aug. 3, 2006 Sheet 3 of 5 US 2006/0172023 A1 O 30 60 90 120 180 240 Patent Application Publication Aug. 3, 2006 Sheet 4 of 5 US 2006/0172023 A1 20 18 16 14. 1.2 10 08 06 04 02 00 O 30 60 90 120 180 240 80 30 20 O O 30 60 90 120 180 240 Fig. 7 Patent Application Publication Aug. 3, 2006 Sheet 5 of 5 US 2006/0172023 A1 70 60 50 l,0 30 20 10 O 30 60 90 120 180 240 Fig. 8 US 2006/0172023 A1 Aug. 3, 2006 USE OF PINOLENIC ACID 0007 Matsuo et al. Prostaglandins, Leukotrienes and 0001. This invention relates to compositions that may be Essential Fatty Acids, (1996), 55(4), 223-229 describes the used for weight management, for controlling food intake and effects of Y-linolenic and pinolenic acid on immune param appetite, and for controlling and/or reducing body weight. eters of Brown-Norway rats. The compositions contain pinolenic acid or a derivative 0008 However, none of the prior art documents indicate thereof. that pinolenic acid or a derivative thereof could be used to 0002 Obesity is becoming increasingly prevalent in indi treat or prevent obesity and/or for weight management. viduals in developed Societies. Generally, an overweight 0009 U.S. Pat. No. 6,429,190, US 2002/01 19948 and US condition and obesity result from an imbalance in energy 2002/01 19915 describe compositions for extending satiety intake and utilisation. The cause of energy imbalance for comprising a calcium source, protein and a C12 to C18 fatty each individual may be due to a combination of several acid. Oleic acid is the fatty acid described in the documents. factors and stems from a myriad of both environmental and genetic determinants. Obesity may be a contributing factor 0010 WO 02/088159 discloses pharmaceutically active in the increased incidence of various diseases including uridine esters, and combinations comprising their constitu coronary artery disease, hypertension, stroke, diabetes and ent acid and uridine compound, and their use in a wide certain cancers. variety of medical applications. There is no disclosure of the use of free fatty acids alone nor is any example given of the 0003 Weight reduction is often recommended as the first treatment of obesity. course of action for patients suffering from these obesity related diseases. In an attempt to control total body weight, 0.011 EP-A-1504778, published on 9 Feb. 2005, an individual may undertake weight management, the objec describes an implantable pump for the treatment of obesity. tives of which may differ depending on the needs of the The pump may comprise a fatty acid but there is no individual. For example, whereas obese or overweight indi disclosure of pinolenic acid. viduals may wish to lose body weight, other individuals may 0012 CN-A-1377673 relates to the use of a pine nut oil wish to maintain a body weight at a Substantially constant for treating cardiac and cerebral vascular diseases and level. Even once a person has lost body weight, weight adiposity caused by hyperlipemia as well as diabetes caused management is often required to prevent that person regain by hyperglycemia. ing the body weight previously lost. The most effective weight loss programmes typically include a reduced calorie 0013 The present invention provides the use of pinolenic diet and/or increased energy expenditure. Over time, many acid or a derivative thereof in the manufacture of a compo people undertaking weight management experience sition for weight management by reducing the feeling of increased hunger levels and/or cravings for high Sugar hunger and/or increasing Satiety. The invention also provides foods. This can lead individuals to stray from their weight the use of pinolenic acid or a derivative thereof for reducing management regime. There is, therefore, a need to develop the feeling of hunger and/or increasing satiety. Thus, com new and effective ways to Support weight management and positions of the invention are Suitable for treating or pre to help individuals continue with their weight management venting obesity and/or for weight management and comprise regime. It is an object of the present invention to provide a pinolenic acid or a derivative thereof. Derivatives of pino new means for providing this Support. lenic acid, which can be used in the present invention, 0004 Pinolenic acid (i.e., 5, 9, 12 C18:3 fatty acid, a fatty include salts of pinolenic acid and alkyl esters. Other deriva acid with 18 C atoms having three double bonds in the tives of pinolenic acid which can be used in the invention are positions 5, 9 and 12) is present in, for example, pine nut oil isomers of pinolenic acid such as, for example, geometric and fractions thereof (J Am Oil Chem Soc 1998, 75, p. isomers (having one or more trans double bonds; the double 45-50). It is known that pine nut oil, and thus pinolenic acid, bonds in pinolenic acid are all cis) and/or compounds having can be applied in food products, see for example, FR-A- 18 carbon atoms and three double bonds with one or more 2756465 wherein the use of a concentrate with 15% pino of the three double bonds at a different position in the alkyl lenic acid in food additives is disclosed. The presence of chain compared to pinolenic acid, including, for example, pinolenic acid is described as providing a hypolipemic effect gamma linolenic acid, alpha linolenic acid, punicic acid, to the composition. eleoStearic acid, and their salts and alkyl esters. 0005 WO98/.43513 discloses that nail files can be coated 0014. The invention also covers, therefore: the use of with pinolenic acid and that this inhibits the occurrence of alpha-linolenic acid or a derivative thereof for weight man infections upon use of the files. agement by reducing the feeling of hunger and/or increasing Satiety; the use of gamma-linolenic acid or a derivative 0006. According to JP-A-61238729, pine nut oil can be thereof for weight management by reducing the feeling of used as an anticholesteric agent. Other documents wherein hunger and/or increasing Satiety; the use of punicic acid or health effects of pinolenic acid are disclosed include JP-A- a derivative thereof for weight management by reducing the 61058536, wherein a very generic activity beneficial for feeling of hunger and/or increasing Satiety; and the use of human health is disclosed. This health activity is not dis eleoStearic acid (also termed alpha-eleostearic acid) or a closed in further detail. Sugano, Brit J. of Nutr 72 (1994) derivative thereof for weight management by reducing the 775-783, discloses a number of health effects of diets feeling of hunger and/or increasing Satiety. containing pinolenic acid. The health effects mentioned are hypocholesterolaemic effects, effects on ADP-induced plate 0015 The invention also contemplates pinolenic acid or let aggregation, on aortic prostacylic production and on a derivative thereof for treating or preventing obesity and/or blood pressure. EP-A-1088552 describes the use of pino for weight management. The pinolenic acid or derivative lenic acid as an anti-inflammatory agent. thereof may be used alone or may be one component of a US 2006/0172023 A1 Aug. 3, 2006 composition which comprises other edible and/or pharma 0021. The pinolenic acid used in the present invention ceutically acceptable components. Preferably, the composi may be in the form of a free fatty acid, a derivative of tion further comprises from 10 to 60 wt % of linoleic acid pinolenic acid or mixtures thereof, including mixtures of and/or from 5 to 52wt % oleic acid, either as free acids or different derivatives. Derivatives are non-toxic and edible glycerides (e.g., mono-, di- or tri-glycerides). Additionally and preferably include, for example, salts and esters. Other or alternatively, the composition may comprise from 0.5 to derivatives of pinolenic acid which can be used in the 5 wt % of taxoleic acid.
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