WO2004069150A2 - Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides - Google Patents
Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides Download PDFInfo
- Publication number
- WO2004069150A2 WO2004069150A2 PCT/IL2004/000131 IL2004000131W WO2004069150A2 WO 2004069150 A2 WO2004069150 A2 WO 2004069150A2 IL 2004000131 W IL2004000131 W IL 2004000131W WO 2004069150 A2 WO2004069150 A2 WO 2004069150A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- phytosterol
- diacylglycerol
- cholesterol
- pharmaceutical composition
- Prior art date
Links
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title claims abstract description 91
- 150000001982 diacylglycerols Chemical class 0.000 title claims abstract description 39
- 150000003626 triacylglycerols Chemical class 0.000 title claims abstract description 37
- 235000012000 cholesterol Nutrition 0.000 title claims abstract description 33
- 239000003921 oil Substances 0.000 title claims description 67
- 230000009467 reduction Effects 0.000 title claims description 20
- 229940075999 phytosterol ester Drugs 0.000 title claims description 12
- 210000002540 macrophage Anatomy 0.000 claims abstract description 77
- 150000002148 esters Chemical class 0.000 claims abstract description 72
- 210000002966 serum Anatomy 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 49
- 235000015872 dietary supplement Nutrition 0.000 claims abstract description 48
- 235000008390 olive oil Nutrition 0.000 claims abstract description 40
- 230000036542 oxidative stress Effects 0.000 claims abstract description 38
- 208000029078 coronary artery disease Diseases 0.000 claims abstract description 27
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 26
- 230000003647 oxidation Effects 0.000 claims abstract description 25
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
- 235000019519 canola oil Nutrition 0.000 claims abstract description 19
- 210000000497 foam cell Anatomy 0.000 claims abstract description 18
- 230000036765 blood level Effects 0.000 claims abstract description 15
- 235000021323 fish oil Nutrition 0.000 claims abstract description 15
- 150000002632 lipids Chemical class 0.000 claims abstract description 15
- 230000002939 deleterious effect Effects 0.000 claims abstract description 14
- 239000008157 edible vegetable oil Substances 0.000 claims abstract description 14
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 240000007817 Olea europaea Species 0.000 claims abstract description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
- 230000002265 prevention Effects 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 240000000385 Brassica napus var. napus Species 0.000 claims abstract 4
- 235000019198 oils Nutrition 0.000 claims description 66
- 230000000694 effects Effects 0.000 claims description 41
- 239000004006 olive oil Substances 0.000 claims description 39
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 34
- 235000019197 fats Nutrition 0.000 claims description 34
- -1 fatty acid esters Chemical class 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 29
- 235000005911 diet Nutrition 0.000 claims description 28
- 230000000378 dietary effect Effects 0.000 claims description 24
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 18
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 18
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 18
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 15
- 230000001590 oxidative effect Effects 0.000 claims description 15
- 108010071584 oxidized low density lipoprotein Proteins 0.000 claims description 15
- 239000000828 canola oil Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims description 10
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 10
- 125000005313 fatty acid group Chemical group 0.000 claims description 10
- 229950005143 sitosterol Drugs 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 9
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 229940076810 beta sitosterol Drugs 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 6
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims description 5
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 claims description 5
- OILXMJHPFNGGTO-NRHJOKMGSA-N Brassicasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 OILXMJHPFNGGTO-NRHJOKMGSA-N 0.000 claims description 5
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims description 5
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims description 5
- OILXMJHPFNGGTO-ZRUUVFCLSA-N UNPD197407 Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)C=C[C@H](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZRUUVFCLSA-N 0.000 claims description 5
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims description 5
- 235000004420 brassicasterol Nutrition 0.000 claims description 5
- 235000000431 campesterol Nutrition 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 208000026758 coronary atherosclerosis Diseases 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 235000016709 nutrition Nutrition 0.000 claims description 5
- 235000012424 soybean oil Nutrition 0.000 claims description 5
- 239000003549 soybean oil Substances 0.000 claims description 5
- 235000016831 stigmasterol Nutrition 0.000 claims description 5
- 229940032091 stigmasterol Drugs 0.000 claims description 5
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims description 5
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims description 4
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- 241001133760 Acoelorraphe Species 0.000 claims description 4
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 claims description 4
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000019482 Palm oil Nutrition 0.000 claims description 4
- 244000025272 Persea americana Species 0.000 claims description 4
- 235000019485 Safflower oil Nutrition 0.000 claims description 4
- 244000000231 Sesamum indicum Species 0.000 claims description 4
- 235000019486 Sunflower oil Nutrition 0.000 claims description 4
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 claims description 4
- 235000014121 butter Nutrition 0.000 claims description 4
- 235000019868 cocoa butter Nutrition 0.000 claims description 4
- 229940110456 cocoa butter Drugs 0.000 claims description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical group CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- 235000021243 milk fat Nutrition 0.000 claims description 4
- 235000005713 safflower oil Nutrition 0.000 claims description 4
- 239000003813 safflower oil Substances 0.000 claims description 4
- 235000011803 sesame oil Nutrition 0.000 claims description 4
- 235000015500 sitosterol Nutrition 0.000 claims description 4
- 239000002600 sunflower oil Substances 0.000 claims description 4
- OSELKOCHBMDKEJ-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4c)-yl)-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 OSELKOCHBMDKEJ-UHFFFAOYSA-N 0.000 claims description 3
- MCWVPSBQQXUCTB-UHFFFAOYSA-N (24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(=CC)C(C)C)CCC33)C)C3=CCC21 MCWVPSBQQXUCTB-UHFFFAOYSA-N 0.000 claims description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 3
- 235000021302 avocado oil Nutrition 0.000 claims description 3
- OILXMJHPFNGGTO-ZAUYPBDWSA-N brassicasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZAUYPBDWSA-N 0.000 claims description 3
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims description 3
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 3
- 235000013376 functional food Nutrition 0.000 claims description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 3
- 235000015097 nutrients Nutrition 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims description 3
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 claims description 3
- 230000036541 health Effects 0.000 claims description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 2
- 235000008673 Persea americana Nutrition 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 150000002888 oleic acid derivatives Chemical class 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 abstract description 19
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 4
- 229940068065 phytosterols Drugs 0.000 description 33
- 210000004027 cell Anatomy 0.000 description 31
- 102000007330 LDL Lipoproteins Human genes 0.000 description 27
- 239000000902 placebo Substances 0.000 description 25
- 229940068196 placebo Drugs 0.000 description 25
- 244000188595 Brassica sinapistrum Species 0.000 description 19
- 241000699670 Mus sp. Species 0.000 description 17
- 241000699666 Mus <mouse, genus> Species 0.000 description 16
- 230000003078 antioxidant effect Effects 0.000 description 15
- 235000002378 plant sterols Nutrition 0.000 description 15
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 12
- 210000004369 blood Anatomy 0.000 description 12
- 239000008280 blood Substances 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 238000008214 LDL Cholesterol Methods 0.000 description 11
- 150000002978 peroxides Chemical class 0.000 description 11
- 102000005862 Angiotensin II Human genes 0.000 description 10
- 101800000733 Angiotensin-2 Proteins 0.000 description 10
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 10
- 102000004895 Lipoproteins Human genes 0.000 description 10
- 108090001030 Lipoproteins Proteins 0.000 description 10
- 229950006323 angiotensin ii Drugs 0.000 description 10
- 235000013305 food Nutrition 0.000 description 10
- 210000003024 peritoneal macrophage Anatomy 0.000 description 10
- 108010028554 LDL Cholesterol Proteins 0.000 description 9
- 230000001413 cellular effect Effects 0.000 description 9
- 235000015112 vegetable and seed oil Nutrition 0.000 description 8
- 239000008158 vegetable oil Substances 0.000 description 8
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 229930182558 Sterol Natural products 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 230000003143 atherosclerotic effect Effects 0.000 description 6
- 230000003859 lipid peroxidation Effects 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 235000003702 sterols Nutrition 0.000 description 6
- 108010010234 HDL Lipoproteins Proteins 0.000 description 5
- 102000015779 HDL Lipoproteins Human genes 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- 241000282412 Homo Species 0.000 description 4
- 101000942681 Rattus norvegicus Clusterin Proteins 0.000 description 4
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 4
- 108010009043 arylesterase Proteins 0.000 description 4
- 102000028848 arylesterase Human genes 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 230000008506 pathogenesis Effects 0.000 description 4
- 229940049953 phenylacetate Drugs 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 4
- 210000002381 plasma Anatomy 0.000 description 4
- 238000011533 pre-incubation Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XDFNWJDGWJVGGN-UHFFFAOYSA-N 2-(2,7-dichloro-3,6-dihydroxy-9h-xanthen-9-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1C2=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C21 XDFNWJDGWJVGGN-UHFFFAOYSA-N 0.000 description 3
- LXEKPEMOWBOYRF-QDBORUFSSA-N AAPH Chemical compound Cl.Cl.NC(=N)C(C)(C)\N=N\C(C)(C)C(N)=N LXEKPEMOWBOYRF-QDBORUFSSA-N 0.000 description 3
- 108010005094 Advanced Glycation End Products Proteins 0.000 description 3
- 102000018832 Cytochromes Human genes 0.000 description 3
- 108010052832 Cytochromes Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920003189 Nylon 4,6 Polymers 0.000 description 3
- 102100035476 Serum paraoxonase/arylesterase 1 Human genes 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical class COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000000684 flow cytometry Methods 0.000 description 3
- 230000007760 free radical scavenging Effects 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 3
- 238000005502 peroxidation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 101150037123 APOE gene Proteins 0.000 description 2
- 101710095339 Apolipoprotein E Proteins 0.000 description 2
- 102100029470 Apolipoprotein E Human genes 0.000 description 2
- 108010008184 Aryldialkylphosphatase Proteins 0.000 description 2
- 102000006996 Aryldialkylphosphatase Human genes 0.000 description 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
- 101100216294 Danio rerio apoeb gene Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 108010023302 HDL Cholesterol Proteins 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- 101001094647 Homo sapiens Serum paraoxonase/arylesterase 1 Proteins 0.000 description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 102000004722 NADPH Oxidases Human genes 0.000 description 2
- 108010002998 NADPH Oxidases Proteins 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 102000019197 Superoxide Dismutase Human genes 0.000 description 2
- 108010012715 Superoxide dismutase Proteins 0.000 description 2
- IWTJDVBNIUPPPB-FPNUYMRSSA-N [(3s,8s,9s,10r,13r,14s,17r)-17-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] hexadecanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CC[C@@H](CC)C(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCCCCCCCCC)C1 IWTJDVBNIUPPPB-FPNUYMRSSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000006851 antioxidant defense Effects 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000008809 cell oxidative stress Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000021474 generally recognized As safe (food) Nutrition 0.000 description 2
- 235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000009884 interesterification Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000000899 pressurised-fluid extraction Methods 0.000 description 2
- 239000003642 reactive oxygen metabolite Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- ZFMRLFXUPVQYAU-UHFFFAOYSA-N sodium 5-[[4-[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-2-hydroxybenzoic acid Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3O)N)S(=O)(=O)O)N=NC5=CC(=C(C=C5)O)C(=O)O.[Na+] ZFMRLFXUPVQYAU-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AOFUBOWZWQFQJU-SNOJBQEQSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol;(2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O AOFUBOWZWQFQJU-SNOJBQEQSA-N 0.000 description 1
- LGJMUZUPVCAVPU-ANOYILKDSA-N (3s,8r,9s,10s,13r,14s,17r)-17-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical compound C1CC2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@H](CC)C(C)C)[C@@]1(C)CC2 LGJMUZUPVCAVPU-ANOYILKDSA-N 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- OVIBXFDXRSJJSX-CLFAGFIQSA-N 1,3-bis[(z)-octadec-9-enoxy]propan-2-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCC(O)COCCCCCCCC\C=C/CCCCCCCC OVIBXFDXRSJJSX-CLFAGFIQSA-N 0.000 description 1
- VFNKZQNIXUFLBC-UHFFFAOYSA-N 2',7'-dichlorofluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(O)C=C1OC1=C2C=C(Cl)C(O)=C1 VFNKZQNIXUFLBC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 235000019737 Animal fat Nutrition 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000013600 Diabetic vascular disease Diseases 0.000 description 1
- 206010048554 Endothelial dysfunction Diseases 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 235000001412 Mediterranean diet Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 101710180981 Serum paraoxonase/arylesterase 1 Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YVDXIVLWTCSVDW-JXMNSIJESA-N [(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CC[C@@H](CC)C(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)C1 YVDXIVLWTCSVDW-JXMNSIJESA-N 0.000 description 1
- FBQNVDGEJMFTTK-FPTIKDCHSA-N [(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)\C=C\[C@@H](CC)C(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)C1 FBQNVDGEJMFTTK-FPTIKDCHSA-N 0.000 description 1
- OHLDETMXEXJUDZ-SYYHSBNDSA-N [(3s,8s,9s,10r,13r,14s,17r)-17-[(e,2r,5s)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] hexadecanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)\C=C\[C@@H](CC)C(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCCCCCCCCC)C1 OHLDETMXEXJUDZ-SYYHSBNDSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 210000003567 ascitic fluid Anatomy 0.000 description 1
- 230000036523 atherogenesis Effects 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- IWTJDVBNIUPPPB-UHFFFAOYSA-N beta-Sitosterylpalmitat Natural products C12CCC3(C)C(C(C)CCC(CC)C(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCCCCCCCCC)C2 IWTJDVBNIUPPPB-UHFFFAOYSA-N 0.000 description 1
- QEXVJKPQWBLYFH-UHFFFAOYSA-N beta-sitosteryl oleate Natural products CCCCCCCCC=CCCCCCCCCOC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCC(CC)C(C)C QEXVJKPQWBLYFH-UHFFFAOYSA-N 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- ARYTXMNEANMLMU-ATEDBJNTSA-N campestanol Chemical class C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]2(C)CC1 ARYTXMNEANMLMU-ATEDBJNTSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 210000002390 cell membrane structure Anatomy 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 210000004671 cell-free system Anatomy 0.000 description 1
- 230000006800 cellular catabolic process Effects 0.000 description 1
- 208000037998 chronic venous disease Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000011018 current good manufacturing practice Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 201000009101 diabetic angiopathy Diseases 0.000 description 1
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 230000008694 endothelial dysfunction Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 230000009483 enzymatic pathway Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002190 fatty acyls Chemical group 0.000 description 1
- 229940114123 ferulate Drugs 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000021472 generally recognized as safe Nutrition 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 244000005709 gut microbiome Species 0.000 description 1
- 230000007407 health benefit Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000000260 hypercholesteremic effect Effects 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000031146 intracellular signal transduction Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 108010022197 lipoprotein cholesterol Proteins 0.000 description 1
- 235000004213 low-fat Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- QAPAPLIQQTVEJZ-UHFFFAOYSA-N n-[(3-fluorophenyl)methyl]ethanamine Chemical compound CCNCC1=CC=CC(F)=C1 QAPAPLIQQTVEJZ-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940097156 peroxyl Drugs 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940107071 plant stanol ester Drugs 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000006041 probiotic Substances 0.000 description 1
- 230000000529 probiotic effect Effects 0.000 description 1
- 235000018291 probiotics Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000036454 renin-angiotensin system Effects 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- YVDXIVLWTCSVDW-UHFFFAOYSA-N sitostreryl oleate Natural products C12CCC3(C)C(C(C)CCC(CC)C(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCC=CCCCCCCCC)C2 YVDXIVLWTCSVDW-UHFFFAOYSA-N 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- OHLDETMXEXJUDZ-UHFFFAOYSA-N stigmasteryl palmitate Natural products C12CCC3(C)C(C(C)C=CC(CC)C(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCCCCCCCCC)C2 OHLDETMXEXJUDZ-UHFFFAOYSA-N 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010463 virgin olive oil Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/3262—Foods, ingredients or supplements having a functional effect on health having an effect on blood cholesterol
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/328—Foods, ingredients or supplements having a functional effect on health having effect on glycaemic control and diabetes
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Botany (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Edible Oils And Fats (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
Claims
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04709679.7A EP1596670B1 (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
CN2004800096136A CN1809284B (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of blood cholestrol and triglycerides |
SI200432168T SI1596670T1 (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
BRPI0407338A BRPI0407338B8 (en) | 2003-02-10 | 2004-02-10 | dietary nutrient or food supplement comprising an edible composition, as well as an orally administrable pharmaceutical composition and uses thereof |
CA002515290A CA2515290A1 (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
DK04709679.7T DK1596670T3 (en) | 2003-02-10 | 2004-02-10 | OILS ENRICHED WITH DIACYLGYLYCEROLES AND PHYTOSTEROL ESTERS USING IREDUCATION OF CHOLESTEROL AND TRIGLYCERIDES |
NZ541887A NZ541887A (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
JP2006502637A JP2006517222A (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerol and phytosterol esters for use in reducing cholesterol and triglycerides |
AU2004210244A AU2004210244C1 (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
IL170022A IL170022A (en) | 2003-02-10 | 2005-08-01 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
US11/199,584 US20060052351A1 (en) | 2003-02-10 | 2005-08-08 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of blood cholestrol and triglycerides and oxidative stress |
US11/396,257 US20060233863A1 (en) | 2003-02-10 | 2006-03-31 | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
HK06105873.5A HK1086168A1 (en) | 2003-02-10 | 2006-05-22 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
AU2009200897A AU2009200897B2 (en) | 2003-02-10 | 2009-03-06 | Oils enriched with diacylglycerols and phytosterol ester for use in the reduction of cholesterol and triglycerides |
US12/655,240 US8507466B2 (en) | 2003-02-10 | 2009-12-23 | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL154381 | 2003-02-10 | ||
IL15438103A IL154381A0 (en) | 2003-02-10 | 2003-02-10 | A composition for reducing blood cholesterol and triglycerides |
IL155136 | 2003-03-27 | ||
IL15513603A IL155136A0 (en) | 2003-02-10 | 2003-03-27 | A composition for reducing blood cholesterol and triglycerides |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/199,584 Continuation-In-Part US20060052351A1 (en) | 2003-02-10 | 2005-08-08 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of blood cholestrol and triglycerides and oxidative stress |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004069150A2 true WO2004069150A2 (en) | 2004-08-19 |
WO2004069150A3 WO2004069150A3 (en) | 2004-09-23 |
Family
ID=32599150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IL2004/000131 WO2004069150A2 (en) | 2003-02-10 | 2004-02-10 | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of cholesterol and triglycerides |
Country Status (13)
Country | Link |
---|---|
US (1) | US20060052351A1 (en) |
EP (1) | EP1596670B1 (en) |
JP (1) | JP2006517222A (en) |
KR (1) | KR100959704B1 (en) |
AU (2) | AU2004210244C1 (en) |
BR (1) | BRPI0407338B8 (en) |
CA (1) | CA2515290A1 (en) |
DK (1) | DK1596670T3 (en) |
HK (1) | HK1086168A1 (en) |
IL (2) | IL155136A0 (en) |
NZ (1) | NZ541887A (en) |
SI (1) | SI1596670T1 (en) |
WO (1) | WO2004069150A2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006016357A1 (en) * | 2004-08-09 | 2006-02-16 | Enzymotec Ltd. | Food products for diabetics |
WO2006016363A2 (en) * | 2004-08-10 | 2006-02-16 | Enzymotec Ltd. | Mixture of phytosterol ester(s) and 1, 3-diglyceride(s) for use in the treatment of medical conditions |
WO2006135729A1 (en) * | 2005-06-09 | 2006-12-21 | Archer-Daniels-Midland Company | Compositions containing protein and dag oil and methods for making them |
US8507466B2 (en) | 2003-02-10 | 2013-08-13 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
US9591861B2 (en) | 2011-08-22 | 2017-03-14 | Koa Corporation | Oil or fat composition |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL147942A0 (en) * | 2002-01-31 | 2002-08-14 | Enzymotec Ltd | Method of fractionation of phytosterol esters in oil and products obtained thereby |
US20080182801A1 (en) | 2003-12-22 | 2008-07-31 | Btg International Limited | Core 2 glcnac-t inhibitors |
GB0513881D0 (en) * | 2005-07-06 | 2005-08-10 | Btg Int Ltd | Core 2 GLCNAC-T Inhibitors III |
GB0329667D0 (en) * | 2003-12-22 | 2004-01-28 | King S College London | Core 2 GlcNAc-T inhibitor |
GB0512726D0 (en) * | 2005-06-22 | 2005-07-27 | Btg Int Ltd | Multiple sclerosis therapy and diagnosis |
GB0513888D0 (en) | 2005-07-06 | 2005-08-10 | Btg Int Ltd | Core 2 GLCNAC-T Inhibitors II |
GB0513883D0 (en) * | 2005-07-06 | 2005-08-10 | Btg Int Ltd | Diagnosis of Atherosclerosis |
JP4852296B2 (en) * | 2005-10-27 | 2012-01-11 | 花王株式会社 | Vasculitis syndrome prevention / treatment agent |
CN102176834A (en) * | 2008-08-11 | 2011-09-07 | 阿邦达营养学股份有限公司 | Diacylglycerol rich fats, oils and functional foods |
KR101760953B1 (en) * | 2008-09-04 | 2017-07-24 | 아밀린 파마슈티칼스, 엘엘씨. | Sustained release formulations using non-aqueous carriers |
WO2010118362A1 (en) | 2009-04-09 | 2010-10-14 | The Regents Of The University Of Colorado, A Body Corporate | Methods and compositions for inducing physiological hypertrophy |
KR100946641B1 (en) * | 2010-01-19 | 2010-03-09 | 연세대학교 산학협력단 | Composition for preventing or treating of obesity, dyslipidemia, fatty liver or insulin resistance syndrome comprising cinchonine as active ingredients |
JP2014529596A (en) * | 2011-08-16 | 2014-11-13 | アボット・ラボラトリーズAbbott Laboratories | How to convert meals |
EP3023011B1 (en) | 2013-06-24 | 2017-05-31 | Mottainai Biomass Research Corporation | Natural binder derived from lipophilic pith fibers (ground stem or stalk internal fibers) separated from sunflower stems or stalks for processed foods and processed foods containing the same. |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4064236A (en) | 1975-12-23 | 1977-12-20 | Merck & Co., Inc. | Peptide carbazates and pharmaceutical composition |
US4457917A (en) | 1981-05-06 | 1984-07-03 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. | Peptide, process for its preparation and pharmaceutical composition containing same |
US4639435A (en) | 1983-06-29 | 1987-01-27 | Kowa Co., Ltd. | Pharmaceutical composition suitable for intestinal administration |
US4900549A (en) | 1986-01-14 | 1990-02-13 | De Staat Der Nederlanden Vertegenwoordigd Door De Minister Van Welzion, Volksgezondheid En Cultuur | Process for preparing immunogenic complexes and pharmaceutical composition containing these complexes |
US5164372A (en) | 1989-04-28 | 1992-11-17 | Fujisawa Pharmaceutical Company, Ltd. | Peptide compounds having substance p antagonism, processes for preparation thereof and pharmaceutical composition comprising the same |
US5298246A (en) | 1991-01-09 | 1994-03-29 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Stable pharmaceutical composition and method for its production |
US5354900A (en) | 1983-12-26 | 1994-10-11 | Suntory Limited | An H-ANP peptide, pharmaceutical composition and method of use |
US5418219A (en) | 1992-01-01 | 1995-05-23 | Suntory Limited | Pharmaceutical composition for treatment of adult respiratory distress syndrome containing human ANP |
US5439688A (en) | 1989-07-28 | 1995-08-08 | Debio Recherche Pharmaceutique S.A. | Process for preparing a pharmaceutical composition |
US5554378A (en) | 1990-09-03 | 1996-09-10 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition and its mucosal use |
US5733877A (en) | 1994-07-22 | 1998-03-31 | Sanwa Kagaku Kenkyusho Co., Ltd. | Pharmaceutical composition containing biologically active peptide or protein |
US5736519A (en) | 1995-06-07 | 1998-04-07 | Deigin; Vladislav I. | Peptide, a method for its preparation and a pharmaceutical composition containing the peptide |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58500638A (en) * | 1981-05-07 | 1983-04-28 | ユニリ−バ− ナ−ムロ−ゼ ベンノ−トシヤ−プ | Synthesis method of ester |
US5843499A (en) * | 1995-12-08 | 1998-12-01 | The United States Of America As Represented By The Secretary Of Agriculture | Corn fiber oil its preparation and use |
FR2750606B1 (en) * | 1996-07-03 | 1999-01-29 | Maurel Sante | ORGANOMETALLIC COMPLEXES BASED ON SITOSTEROLS AND DIGLYCERIDES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
US6046022A (en) * | 1996-09-30 | 2000-04-04 | Peking University | Methods and compositions employing red rice fermentation products |
JPH10231495A (en) * | 1996-12-20 | 1998-09-02 | Jiyanifu Tec:Kk | Substance having function of preventing growing fat and of decreasing accumulated fan in viscera and its use |
DE69826592T2 (en) * | 1997-08-22 | 2006-02-23 | Unilever N.V. | Process for the preparation of stanol esters |
AU8760898A (en) * | 1997-09-24 | 1999-04-12 | Enzymotec Ltd. | Surfactant-lipase complex immobilized on insoluble matrix |
BR9904796B1 (en) * | 1998-03-24 | 2012-02-22 | phytosterol-containing oil or fat composition, oil or fat composition, food product, beverage product, and cooking table oil. | |
US6025348A (en) * | 1998-04-30 | 2000-02-15 | Kao Corporation | Oil and fat composition containing phytosterol |
FI111513B (en) * | 1998-05-06 | 2003-08-15 | Raisio Benecol Oy | Novel compositions of phytosterol and phytostanol fatty acid esters, products containing them and processes for their preparation |
US6277431B1 (en) * | 1998-10-14 | 2001-08-21 | Redeem, Inc. | Anticholesterolemic edible oil |
US6129945A (en) * | 1998-12-10 | 2000-10-10 | Michael E. George | Methods to reduce free fatty acids and cholesterol in anhydrous animal fat |
US6080173A (en) * | 1999-05-26 | 2000-06-27 | Idx Medical Ltd. | Tissue punching instrument |
US6365211B1 (en) * | 1999-06-18 | 2002-04-02 | The Procter & Gamble Co. | Cooking aid with reduced foaming |
JP2003512850A (en) * | 1999-11-03 | 2003-04-08 | フォーブス メディ−テック インコーポレーテッド | Compositions comprising edible oils or fats and phytosterols and / or filostanols substantially dissolved therein, methods for their preparation, and their use in treating or preventing cardiovascular diseases and underlying conditions |
US20020132035A1 (en) * | 2001-01-10 | 2002-09-19 | Dov Tamarkin | Synthetic fat composition |
JP4911815B2 (en) * | 2000-04-28 | 2012-04-04 | 株式会社Adeka | Plant sterol-containing oil and fat composition |
JP3774110B2 (en) * | 2000-07-19 | 2006-05-10 | 花王株式会社 | Edible oil and fat and method for producing the same |
JP4031219B2 (en) * | 2000-08-08 | 2008-01-09 | 花王株式会社 | Oil composition |
US7008661B2 (en) * | 2000-08-08 | 2006-03-07 | Kao Corporation | Oil/fat composition |
KR20080064882A (en) * | 2000-11-13 | 2008-07-09 | 니폰스이산가이샤 | Soybean milks containing epa at high concentration and process for producing the same |
SE523094C2 (en) * | 2001-01-11 | 2004-03-30 | Karlshamns Ab | Process for the preparation of a fat composition containing sterol esters, free sterols and glycerides, fat composition prepared by the process and use of the fat composition |
JP3746270B2 (en) * | 2001-01-29 | 2006-02-15 | エムエルビー、エンタープライゼス、エルエルシー | Anticholesterolemia cooking oil |
US6667068B2 (en) * | 2001-01-29 | 2003-12-23 | Kraft Foods Holdings, Inc. | Method for preparing solid milk product |
GB0104074D0 (en) * | 2001-02-19 | 2001-04-04 | Novartis Ag | New composition |
JP4995377B2 (en) * | 2001-04-26 | 2012-08-08 | 花王株式会社 | Oil composition |
GB0114014D0 (en) * | 2001-06-08 | 2001-08-01 | Novartis Nutrition Ag | Compostion and use |
IL147942A0 (en) * | 2002-01-31 | 2002-08-14 | Enzymotec Ltd | Method of fractionation of phytosterol esters in oil and products obtained thereby |
US20060233863A1 (en) * | 2003-02-10 | 2006-10-19 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
US20040219188A1 (en) * | 2003-05-02 | 2004-11-04 | Comer Gail M. | Composition and methods for nutritional management of patients with hepatic disease |
US20050032757A1 (en) * | 2003-08-06 | 2005-02-10 | Cho Suk H. | Nutritional supplements |
-
2003
- 2003-03-27 IL IL15513603A patent/IL155136A0/en unknown
-
2004
- 2004-02-10 SI SI200432168T patent/SI1596670T1/en unknown
- 2004-02-10 WO PCT/IL2004/000131 patent/WO2004069150A2/en active Search and Examination
- 2004-02-10 DK DK04709679.7T patent/DK1596670T3/en active
- 2004-02-10 KR KR1020057014677A patent/KR100959704B1/en active IP Right Grant
- 2004-02-10 BR BRPI0407338A patent/BRPI0407338B8/en not_active IP Right Cessation
- 2004-02-10 JP JP2006502637A patent/JP2006517222A/en active Pending
- 2004-02-10 EP EP04709679.7A patent/EP1596670B1/en not_active Expired - Fee Related
- 2004-02-10 CA CA002515290A patent/CA2515290A1/en not_active Abandoned
- 2004-02-10 NZ NZ541887A patent/NZ541887A/en not_active IP Right Cessation
- 2004-02-10 AU AU2004210244A patent/AU2004210244C1/en not_active Ceased
-
2005
- 2005-08-01 IL IL170022A patent/IL170022A/en active IP Right Grant
- 2005-08-08 US US11/199,584 patent/US20060052351A1/en not_active Abandoned
-
2006
- 2006-05-22 HK HK06105873.5A patent/HK1086168A1/en not_active IP Right Cessation
-
2009
- 2009-03-06 AU AU2009200897A patent/AU2009200897B2/en not_active Ceased
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4064236A (en) | 1975-12-23 | 1977-12-20 | Merck & Co., Inc. | Peptide carbazates and pharmaceutical composition |
US4457917A (en) | 1981-05-06 | 1984-07-03 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. | Peptide, process for its preparation and pharmaceutical composition containing same |
US4639435A (en) | 1983-06-29 | 1987-01-27 | Kowa Co., Ltd. | Pharmaceutical composition suitable for intestinal administration |
US4755383A (en) | 1983-06-29 | 1988-07-05 | Kowa Co., Ltd. | Pharmaceutical composition suitable for intestinal administration |
US5354900A (en) | 1983-12-26 | 1994-10-11 | Suntory Limited | An H-ANP peptide, pharmaceutical composition and method of use |
US4900549A (en) | 1986-01-14 | 1990-02-13 | De Staat Der Nederlanden Vertegenwoordigd Door De Minister Van Welzion, Volksgezondheid En Cultuur | Process for preparing immunogenic complexes and pharmaceutical composition containing these complexes |
US5164372A (en) | 1989-04-28 | 1992-11-17 | Fujisawa Pharmaceutical Company, Ltd. | Peptide compounds having substance p antagonism, processes for preparation thereof and pharmaceutical composition comprising the same |
US5439688A (en) | 1989-07-28 | 1995-08-08 | Debio Recherche Pharmaceutique S.A. | Process for preparing a pharmaceutical composition |
US5554378A (en) | 1990-09-03 | 1996-09-10 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition and its mucosal use |
US5298246A (en) | 1991-01-09 | 1994-03-29 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Stable pharmaceutical composition and method for its production |
US5418219A (en) | 1992-01-01 | 1995-05-23 | Suntory Limited | Pharmaceutical composition for treatment of adult respiratory distress syndrome containing human ANP |
US5733877A (en) | 1994-07-22 | 1998-03-31 | Sanwa Kagaku Kenkyusho Co., Ltd. | Pharmaceutical composition containing biologically active peptide or protein |
US5736519A (en) | 1995-06-07 | 1998-04-07 | Deigin; Vladislav I. | Peptide, a method for its preparation and a pharmaceutical composition containing the peptide |
Non-Patent Citations (10)
Title |
---|
AVIRAM M., FREE. RADIC. RES., vol. 33, 2000, pages 585 - 97 |
AVIRAM M.; FUHRMAN B., MOL. CELL. BIOCHEM., vol. 188, 1998, pages 149 - 159 |
BROWN M.S; GOLDSTEIN J.L., ANN. REV. BIOCHEM., vol. 52, 1983, pages 223 - 261 |
GLASS C.K.; WITZTUM J.L., CELL, vol. 104, 2001, pages 503 - 516 |
HAYEK T. ET AL., BIOCHEM. BIOPHYS. RES. COMMUN., vol. 201, 1994, pages 1567 - 1574 |
JOHNSTON R.B. JR., METHODS ENZYMOL., vol. 105, 1984, pages 365 - 9 |
KEIDAR S., LIFE SCI., vol. 63, 1998, pages 1 - 11 |
PLUMP A.S. ET AL., CELL, vol. 71, 1992, pages 343 - 353 |
RAJAGOPALAN S. ET AL., J. CLIN. INVEST., vol. 97, 1996, pages 1916 - 1923 |
ROSS R., NATURE, vol. 362, 1993, pages 801 - 809 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8507466B2 (en) | 2003-02-10 | 2013-08-13 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
WO2006016357A1 (en) * | 2004-08-09 | 2006-02-16 | Enzymotec Ltd. | Food products for diabetics |
CN101035594B (en) * | 2004-08-09 | 2013-10-23 | 酶学技术有限公司 | Food products for diabetics |
WO2006016363A2 (en) * | 2004-08-10 | 2006-02-16 | Enzymotec Ltd. | Mixture of phytosterol ester(s) and 1, 3-diglyceride(s) for use in the treatment of medical conditions |
WO2006016363A3 (en) * | 2004-08-10 | 2006-03-16 | Enzymotec Ltd | Mixture of phytosterol ester(s) and 1, 3-diglyceride(s) for use in the treatment of medical conditions |
US8772270B2 (en) * | 2004-08-10 | 2014-07-08 | Enzymotec Ltd. | Treatment methods requiring phyto-ingredients |
WO2006135729A1 (en) * | 2005-06-09 | 2006-12-21 | Archer-Daniels-Midland Company | Compositions containing protein and dag oil and methods for making them |
US9591861B2 (en) | 2011-08-22 | 2017-03-14 | Koa Corporation | Oil or fat composition |
Also Published As
Publication number | Publication date |
---|---|
AU2004210244B9 (en) | 2009-02-05 |
EP1596670A2 (en) | 2005-11-23 |
EP1596670B1 (en) | 2014-05-07 |
CA2515290A1 (en) | 2004-08-19 |
KR20050121672A (en) | 2005-12-27 |
NZ541887A (en) | 2007-05-31 |
BRPI0407338A (en) | 2006-01-10 |
IL170022A (en) | 2015-11-30 |
AU2004210244A1 (en) | 2004-08-19 |
US20060052351A1 (en) | 2006-03-09 |
DK1596670T3 (en) | 2014-07-28 |
WO2004069150A3 (en) | 2004-09-23 |
SI1596670T1 (en) | 2014-08-29 |
BRPI0407338B8 (en) | 2021-05-25 |
HK1086168A1 (en) | 2006-09-15 |
KR100959704B1 (en) | 2010-05-25 |
BRPI0407338B1 (en) | 2016-10-25 |
IL155136A0 (en) | 2003-10-31 |
JP2006517222A (en) | 2006-07-20 |
AU2004210244C1 (en) | 2009-07-16 |
AU2009200897B2 (en) | 2011-12-08 |
AU2004210244B2 (en) | 2008-12-11 |
AU2009200897A1 (en) | 2009-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2009200897B2 (en) | Oils enriched with diacylglycerols and phytosterol ester for use in the reduction of cholesterol and triglycerides | |
US10342773B2 (en) | Composition containing dihomo-γ-linolenic acid (DGLA) as the active ingredient | |
AU2010201897B2 (en) | Dietary supplement composition for blood lipid health | |
US8507466B2 (en) | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy | |
KR101323513B1 (en) | Mixture of Phytosterol Ester(s) and 1,3-Diglyceride(s) for Use in the Treatment of Medical Conditions | |
TWI359667B (en) | Formulation for oral administration having a healt | |
WO2005110400A1 (en) | Lipase inhibitor, cholesterol esterase inhibtor, neutral fat absorption inhibitor, cholesterol absorption inhibitor and cholesterol ester absorption inhibitor | |
ES2398847T3 (en) | Composition comprising one or more phytosterols and / or phytostanols and glucomannan and uses of the composition to treat lipid disorders in individuals with and without type II diabetes | |
ES2816008T3 (en) | DHA-enriched polyunsaturated fatty acid compositions | |
CN1809284B (en) | Oils enriched with diacylglycerols and phytosterol esters for use in the reduction of blood cholestrol and triglycerides | |
US8993551B2 (en) | Composition for the regulation of the human immune system and the prevention and treatment of diseases thereof | |
KR100302024B1 (en) | Extract of safflower seed for decreasing blood cholesterol level and method for preparation of the same | |
US8062690B2 (en) | Dietary supplement composition for blood lipid health | |
Ho et al. | Beneficial effects of plant sterols/stanols-containing milk powder on lipid metabolism in hamsters | |
CA2538494C (en) | Composition for modulating blood parameters |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 170022 Country of ref document: IL |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2515290 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1-2005-501456 Country of ref document: PH Ref document number: 11199584 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020057014677 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006502637 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004210244 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 541887 Country of ref document: NZ |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004709679 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2004210244 Country of ref document: AU Date of ref document: 20040210 Kind code of ref document: A |
|
WWP | Wipo information: published in national office |
Ref document number: 2004210244 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 20048096136 Country of ref document: CN |
|
WWP | Wipo information: published in national office |
Ref document number: 2004709679 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1020057014677 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref document number: PI0407338 Country of ref document: BR |
|
WWP | Wipo information: published in national office |
Ref document number: 11199584 Country of ref document: US |
|
DPEN | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101) |