WO1990010380A1 - Production d'une huile de colza amelioree presentant une teneur en acide oleique accrue - Google Patents
Production d'une huile de colza amelioree presentant une teneur en acide oleique accrue Download PDFInfo
- Publication number
- WO1990010380A1 WO1990010380A1 PCT/US1989/000835 US8900835W WO9010380A1 WO 1990010380 A1 WO1990010380 A1 WO 1990010380A1 US 8900835 W US8900835 W US 8900835W WO 9010380 A1 WO9010380 A1 WO 9010380A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid content
- percent
- rapeseeds
- total fatty
- weight based
- Prior art date
Links
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 title claims abstract description 95
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 88
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 88
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 88
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 88
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 235000004977 Brassica sinapistrum Nutrition 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title description 8
- 230000001747 exhibiting effect Effects 0.000 title description 6
- 244000188595 Brassica sinapistrum Species 0.000 title 1
- 240000002791 Brassica napus Species 0.000 claims abstract description 122
- 241000196324 Embryophyta Species 0.000 claims abstract description 88
- 235000011293 Brassica napus Nutrition 0.000 claims abstract description 80
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims abstract description 65
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 37
- 239000008158 vegetable oil Substances 0.000 claims abstract description 37
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims abstract description 33
- 229960004488 linolenic acid Drugs 0.000 claims abstract description 33
- 231100000350 mutagenesis Toxicity 0.000 claims abstract description 24
- 230000001965 increasing effect Effects 0.000 claims abstract description 21
- 238000002703 mutagenesis Methods 0.000 claims abstract description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 86
- 239000000194 fatty acid Substances 0.000 claims description 86
- 229930195729 fatty acid Natural products 0.000 claims description 86
- 150000004665 fatty acids Chemical class 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 30
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 25
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 25
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 25
- 230000010153 self-pollination Effects 0.000 claims description 16
- 125000004383 glucosinolate group Chemical group 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 239000002962 chemical mutagen Substances 0.000 claims description 8
- 230000002708 enhancing effect Effects 0.000 claims description 8
- 230000002068 genetic effect Effects 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 230000035772 mutation Effects 0.000 claims description 5
- 230000001172 regenerating effect Effects 0.000 claims description 2
- 239000003921 oil Substances 0.000 abstract description 14
- 235000019198 oils Nutrition 0.000 abstract description 14
- 230000001590 oxidative effect Effects 0.000 abstract description 5
- 238000004458 analytical method Methods 0.000 description 16
- 235000006008 Brassica napus var napus Nutrition 0.000 description 13
- 240000000385 Brassica napus var. napus Species 0.000 description 13
- 238000009395 breeding Methods 0.000 description 12
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 11
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 11
- 230000001488 breeding effect Effects 0.000 description 11
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 9
- FUSGACRLAFQQRL-UHFFFAOYSA-N N-Ethyl-N-nitrosourea Chemical compound CCN(N=O)C(N)=O FUSGACRLAFQQRL-UHFFFAOYSA-N 0.000 description 8
- 235000019484 Rapeseed oil Nutrition 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 235000019519 canola oil Nutrition 0.000 description 6
- 239000000828 canola oil Substances 0.000 description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 5
- 238000001030 gas--liquid chromatography Methods 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 150000004671 saturated fatty acids Chemical class 0.000 description 5
- 244000060924 Brassica campestris Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 230000009418 agronomic effect Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000002939 deleterious effect Effects 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 150000002943 palmitic acids Chemical class 0.000 description 4
- 238000003976 plant breeding Methods 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 230000035899 viability Effects 0.000 description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000035800 maturation Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 230000010152 pollination Effects 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- -1 2- hydroxy-3-butenyl Chemical group 0.000 description 2
- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000005637 Brassica campestris Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- TVFDJXOCXUVLDH-RNFDNDRNSA-N cesium-137 Chemical compound [137Cs] TVFDJXOCXUVLDH-RNFDNDRNSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 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 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000068687 Amelanchier alnifolia Species 0.000 description 1
- 235000009027 Amelanchier alnifolia Nutrition 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- XMJFVIGTHMOGNZ-NSUIRHMESA-N Glucobrassicanapin Natural products S(=O)(=O)(O/N=C(/S[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)\CCCC=C)O XMJFVIGTHMOGNZ-NSUIRHMESA-N 0.000 description 1
- NCWFGOSXGPNCHQ-KAMPLNKDSA-N Gluconapin Natural products OC[C@H]1O[C@H](SC=NCCC=C)[C@H](O)[C@@H](O)[C@@H]1O NCWFGOSXGPNCHQ-KAMPLNKDSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000001412 Mediterranean diet Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000010154 cross-pollination Effects 0.000 description 1
- 239000012297 crystallization seed Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 238000012239 gene modification Methods 0.000 description 1
- 230000005017 genetic modification Effects 0.000 description 1
- 235000013617 genetically modified food Nutrition 0.000 description 1
- XMJFVIGTHMOGNZ-AHMUMSBHSA-N glucobrassicanapin Chemical compound OC[C@H]1O[C@@H](S\C(CCCC=C)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O XMJFVIGTHMOGNZ-AHMUMSBHSA-N 0.000 description 1
- PLYQBXHVYUJNQB-IIPHORNXSA-N gluconapin Chemical compound OC[C@H]1O[C@@H](S\C(CCC=C)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O PLYQBXHVYUJNQB-IIPHORNXSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000014107 unsaturated dietary fats Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H1/00—Processes for modifying genotypes ; Plants characterised by associated natural traits
- A01H1/10—Processes for modifying non-agronomic quality output traits, e.g. for industrial processing; Value added, non-agronomic traits
- A01H1/101—Processes for modifying non-agronomic quality output traits, e.g. for industrial processing; Value added, non-agronomic traits involving biosynthetic or metabolic pathways, i.e. metabolic engineering, e.g. nicotine or caffeine
- A01H1/104—Processes for modifying non-agronomic quality output traits, e.g. for industrial processing; Value added, non-agronomic traits involving biosynthetic or metabolic pathways, i.e. metabolic engineering, e.g. nicotine or caffeine involving modified lipid metabolism, e.g. seed oil composition
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H1/00—Processes for modifying genotypes ; Plants characterised by associated natural traits
- A01H1/06—Processes for producing mutations, e.g. treatment with chemicals or with radiation
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H5/00—Angiosperms, i.e. flowering plants, characterised by their plant parts; Angiosperms characterised otherwise than by their botanic taxonomy
- A01H5/10—Seeds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
- A01H6/20—Brassicaceae, e.g. canola, broccoli or rucola
- A01H6/202—Brassica napus [canola]
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
Definitions
- Rape i.e. , Brassica napus and Brassica camoestris
- Rape is being grown as an increasingly important oilseed crop in many parts of the world.
- As a source 5 of vegetable oil it presently ranks behind only soybeans and palm and is virtually tied with sunflower for the number three position of commercial importance. The oil is used as both a cooking and salad oil throughout the world.
- rapeseed oil was found to have deleterious effects on human health due to its relatively high level of erucic acid which commonly is present in native cultivars in concentrations of 30 to 50 percent by weight based upon the total fatty acid 5 content.
- canola oil is being marketed by Procter & Gamble under the Puritan trademark.
- Such vegetable oil typically is free of cholesterol, and the fatty acids present in it consist of approximately 6 percent saturated fatty acids in the form of stearic and palmitic acids, approximately 22 percent by weight linoleic acid which contains two double bonds per molecule of 18 carbon atoms, approximately 10 percent by weight alpha-linolenic acid which contains three double bonds per molecule of 18 carbon atoms, approximately 62 percent by weight oleic acid which contains a single double bond per molecule of 18 carbon atoms, and less than one percent by weight erucic acid which contains a single double bond per molecule of 22 carbon atoms.
- the oxidative stability of the vegetable oil is related to the number of double bonds in its fatty acids. That is molecules with several double bonds are recognized to be more unstable.
- scientists have attempted to reduce the content of alpha-linolenic acid in order to improve shelf life and oxidative stability, particularly under heat. This has not proved to be possible through the use of naturally occurring germplasm and the reported values for alpha-linolenic acid for such germplasm have been greater than 6 percent by weight (e.g.. greater than 6 up to approximately 12 percent by weight) .
- a substantially homogeneous assemblage of mature rapeseeds is provided, wherein the rapeseeds are capable of yielding a vegetable oil of increased stability when exposed to heat, having (1) an unusually high oleic acid content of at least 79 percent by weight based upon the total fatty acid content, (2) an erucic acid content of no more than 2.0 percent by weight based on the total fatty acid content, and (3) a glucosinolate content in the solid component of less than 100 micromoles per gram.
- a substantially uniform stand of rape plants which upon self-pollination are capable of forming rapeseeds which yield a vegetable oil of increased stability when exposed to heat, wherein the rapeseeds have (1) an unusually high oleic acid content of at least 79 percent by weight based upon the total fatty acid content, (2) an erucic acid content of no more than 2.0 percent by weight based on the total fatty acid content, and (3) a glucosinolate content in the solid component of less than 100 micromoles per gram.
- An improved vegetable oil derived from rapeseeds of increased stability when exposed to heat said rapeseeds having (1) an unusually high oleic acid content of at least 79 percent by weight based upon the total fatty acid content, (2) an erucic acid content of no more than 2.0 percent by weight based upon the total fatty acid content, and (3) an alpha-linolenic acid content less than 5 percent by weight based upon the total fatty acid content.
- a method of enhancing the oleic acid content of rapeseeds comprises:
- step (b) regenerating said cells to produce a rape plant and to form rapeseed in at least one generation subsequent to that of step (a) ,
- step (c) selecting a rapeseed produced in step (b) which has an oleic acid content of at least 79 percent by weight based upon the total fatty acid content,
- step (d) producing a rape plant on the basis of said selection of step (c) , and
- step (e) self-pollinating the rape plant of step (d) for a sufficient number of generations to achieve substantial genetic homogeneity and to form rapeseeds which contain at least 79 percent oleic acid by weight based upon the total fatty acid content.
- rapeseed plants whether Brassica napus or Brassica campestris. have formed rapeseeds which possess an oleic acid content of well under 79 percent by weight based upon the total fatty acid content.
- the oleic acid content of a given rapeseed is determined by a standard procedure wherein the oil is removed from the rapeseeds by crushing the seeds and is extracted as a methyl ester following reaction with methanol and sodium hydroxide. Next the resulting ester is analyzed for fatty acid content by gas liquid chromatography using a .capillary column which allows separation on the basis of the degree of unsaturation and chain length.
- plant cells may be derived from Brassica napus or Brassica campestris plants.
- the Brassica napus plants may be of either the summer or winter types.
- the plant cells derived from a rapeseed plant which forms rapeseeds which possess an oleic acid content of less than 79 percent by weight based upon the total fatty acid content next are subjected in at least one generation to mutagenesis, a rape plant is regenerated from the cells to produce a rape plant and to form rapeseed in at least one subsequent generation, rapeseed is selected having an oleic acid content of at least 79 percent by weight based upon the total fatty acid content, and a rape plant is produced on the basis of this selection which is self-pollinated for a sufficient number of generations (e.g..).
- the plant cells which are subjected to mutagenesis also commonly are from plants which form rapeseeds having an alpha- linolenic content of greater than 5.0 percent by weight (e.g.. greater than 3.5 percent by weight), and selection concurrently is made for a reduced alpha- linolenic acid content.
- the mutagenesis preferably is carried out by subjecting the plant cells (e.g..
- a rapeseed to a technique selected from the group consisting of gamma irradiation, contact with a chemical mutagen, and a combination of the foregoing, for a sufficient duration to accomplish the desired increase in oleic acid content (and preferably also the desired decrease in alpha-linolenic acid content) via a genetic modification but insufficient to destroy the viability of the cells and their ability to be regenerated into a plant.
- a rapeseed preferably possesses a moisture content of approximately 5 to 6 percent by weight at the time of such mutagenesis.
- the mutagenesis preferably is carried out by gamma radiation, such as that supplied by a Cesium 137 source.
- the gamma radiation preferably is supplied to the plant cells (e.g. , a rapeseed) in a dosage of approximately 60 to 200 Krad. , and most preferably in a dosage of approximately 60 to 90 Krad. It should be understood that even when operating at radiation dosages within the ranges specified, some plant cells (e.g.. rapeseeds) will lose their viability and must be discarded.
- the desired mutagenesis may be accomplished by use of chemical means such as by contact with ethylmethylsulfonate, ethylnitrosourea, etc. , and by the use of physical means such as x-ray, etc.
- mutagenesis treatment will result in a wide variety of genetic changes within the rape plants which are produced. Many of these changes will be deleterious to the viability of the resulting plant over an extended period of time. Some changes also will produce viable plants which possess deficient agronomic characteristics. Such off-types may be simply discarded. However, if desired plants which have undergone mutation with respect to oleic acid production coupled with undesirable agronomic traits can be retained and used as breeding or source material from which plants having the targeted trait coupled with satisfactory agronomic characteristics are derived.
- rape plants are regenerated from the treated cells using known techniques. For instance, the resulting rapeseeds may be planted in accordance with conventional rape growing procedures and following self-pollination rapeseed is formed thereon. Alternatively, doubled haploid plantlets may be extracted.
- the planting of the treated rapeseed preferably is carried out in a greenhouse in which the pollination is carefully controlled and monitored. Additional rapeseed which is formed as a result of such self-pollination in the present or a subsequent generation is harvested and is subjected to analysis for oleic acid content.
- Brassica napus and Brassica campestris are dicotyledons
- the analysis for oleic acid can be carried out on a halfseed, and the remaining halfseed can be retained for possible future germination if the oleic acid content is found to be favorable as a result of the mutagenesis.
- the rapeseeds can be carefully separated into two halfseeds using known techniques.
- oleic content of at least 79 percent by weight (preferably at least 80 percent by weight)
- the oleic acid content of such selection preferably will be 79 to 90 percent by weight (e.g.. 80 to 85 percent by weight) .
- the other halfseed i.e.. cotyledon
- the other halfseed which will be genetically the same as the halfseed which was subjected to halfseed analysis can next be caused to germinate and a rape plant is formed and allowed to undergo self-pollination.
- Such planting of the halfseed preferably also is carried out in a greenhouse in which the pollination is carefully controlled and monitored.
- the resulting rapeseed is harvested, planted, and is self-pollinated for a sufficient number of generations to achieve substantial genetic homogeneity.
- the genetic stabilization of the rape plant material enables the creation of plants having a reasonably predictable genotype which can be used as breeding or source material for the production of other improved rape varieties, as a finished variety for use by the rapeseed grower, or as a parent in the production of hybrid rapeseed with the high oleic acid content being transferred to the progeny.
- the resulting rapeseeds also are selected so that they possess the erucic acid and glucosinolate contents of canola. More specifically, the erucic acid content is no more than 2.0 percent by weight based upon the total fatty acid content, and preferably less than 0.1 percent by weight (e.g.. less than 0.05 percent by weight) based on the total fatty acid content, and the gluconsinolate content in the solid component is less than 100 micromoles per gram (preferably less than 30 micromoles per gram) .
- the glucosinolate content may be any one or a mixture of 3-butenyl glucosinolate, 4-pentenyl glucosinolate, 2- hydroxy-3-butenyl glucosinolate, and 2-hydroxy-4- pentenyl gluconsinolate.
- the gluconsinolate determination preferably is made on the air-dry-oil- free solid as measured by the gas liquid chromatograph method of the Canadian Grain Commission.
- the erucic acid and glucosinolate levels commonly are made . possible by selecting starting materials which already possess highly desirable levels of these components.
- the resulting rapeseeds also are selected which have an alpha- linolenic acid content less than 5 percent by weight based upon the total fatty acid content (e.g.. preferably no more than 3.5 percent by weight based upon the total fatty acid content) .
- the vegetable oil contains no more than 7 percent by weight of saturated fatty acids in the form of stearic and palmitic acids based upon the total fatty acid content (e.g. 6 to 7 percent by weight) .
- the desired traits described herein e.g. , unusually high oleic acid content
- the desired traits described herein can be readily transferred into other plants within the same Brassica napus or Brassica campestris species by conventional plant breeding techniques involving cross- pollination and selection of the progeny. It has been demonstrated that the characteristics are highly heritable, can be transmitted to their progeny, and can be recovered in segregating progeny in subsequent generations following crossing. Also, once established the desired traits can be transferred between the napus and campestris species using the same conventional plant breeding techniques involving pollen transfer and selection. The transfer of other traits, such as low erucic acid content, between the napus and campestris species by standard plant breeding techniques is already well documented in the technical literature.
- campestris variety See, for instance, Brassica Crops and Wild Allies Biology and Breeding, edited by S. Tsunada, K. Hinata, and Gomez Campo, Japan Scientific Press, Tokyo (1980) .
- desired traits described herein e.g. f unusually high oleic acid content
- campestris variety such as
- Tobin, Horizon, or Colt and carry out an interspecific cross with an appropriate plant of the napus breeding lines discussed hereafter (e.g.. FA677-39, Topas H6-90 and FA677M5-132) .
- other napus breeding lines may be reliably and independently developed when following the mutagenesis techniques described herein.
- the Tobin variety is available from Agriculture Canada, Saskatoon, Saskatchewan, and other distributors.
- the Horizon and Colt varieties are available from Bonis & Company Ltd. of Lindsay, Ontario, Canada.
- members of the F ⁇ generation are self-pollinated to produce F2 seed. Selection for the desired traits (e.g...
- the rapeseeds possessing the specified combination of characteristics are multiplied to form a substantially uniform assemblage of such seeds (e.g.. a bag of such seeds) which can be used to produce a substantially uniform stand of such rape plants.
- the rapeseeds present in such assemblage number at least 250 seeds, and the resulting substantially uniform stand of rape plants numbers at least 250 plants.
- the improved vegetable oil of the present invention may be formed by simple extraction in a direct manner from the mature rapeseeds such as by crushing and extraction in accordance with known techniques. See, for example. Chapter 8 entitled “Rapeseed Crushing and Extraction” by D.H.C. Beach appearing in “High and Low Erucic Acid Rapeseed Oils,” Academic Press Canada (1983) which is herein incorporated by reference.
- the vegetable oil is present in a quantity convenient for commercial or domestic use (e.g.. a quantity of at least one liter) .
- mutagenesis has been found to be capable of increasing the oleic acid content to such high levels in rape is considered to be complex and incapable of simple explanation.
- the mutation may adversely impact upon the formation of one or more enzymes which normally would function in dehydrogenation of the fatty acids as the seeds mature.
- Example I Seeds of the Regent variety of Brassica napus were selected as the starting material.
- This variety of canola is of the summer type and is suitable to produce vegetable oil when grown in the north central region of the United States, the western prairie area of Canada, and other areas where summer rape is adapted.
- the Regent variety was first introduced in 1977 by the University of Manitoba. Planting seed for the Regent variety is available from the Department of Plant Science of the University of Manitoba.
- a representative sample (i.e.. 2.0 grams) of the mature seeds of the starting material prior to subjection to gamma radiation contained the following fatty acids in the approximate concentrations indicated based upon the total weight of the fatty acids present while using gas liquid chromatography analysis technique previously described: Number of Number of Carbon Atoms Double Bonds Weight
- the gluconsinolate content in the solid component was 13.44 micromoles per gram as determined by the gas liquid chromatograph method of the Canadian Grain Commission.
- the seeds of the Regent variety of canola were stored under conditions so as to maintain viability. More specifically, the seeds were stored in a cold storage room maintained at approximately 10 ⁇ C. and 40 percent relative humidity, and contained a moisture content of approximately 5.5 percent by weight following air drying.
- Seeds of the Regent variety i.e.. approximately 10 grams
- a Gammacell 1000 gamma irradiation apparatus manufactured by Atomic Energy of Canada, Ltd. where they were subjected 90 Krad. of irradiation produced by a Cesium 137 source at a rate of 26.61 Krad. per hour in order induce mutagenesis.
- These seeds can be termed Ml seeds.
- the Ml seeds following subjection to gamma irradiation were planted in a greenhouse at Georgetown, Ontario, Canada, having a day temperature of approximately 25 ⁇ 3 ⁇ C, and a night temperature of approximately 18 ⁇ C. Approximately 40 percent of the gamma irradiated seeds produced fertile rape plants which upon self-pollination yielded M2 seeds. The M2 seeds were next planted in the field at the same location to produce plants which following pollination produced M3 seeds.
- All the M3 halfseeds including FA 677 were planted in the greenhouse and were caused to undergo self-pollination and to form the M4 generation. Each of these plants produced sufficient seed for random 50 seed samples from each plant to be crushed and analyzed by gas liquid chromatography. When these representative 50 seed samples from the M4 generation were analyzed, it was found that the oleic acid content ranged from 63 to 80 percent by weight based upon the total fatty acid content, and the alpha-linolenic acid content ranged from 3.2 to 7.7 percent by weight based upon the total fatty acid content. The single plant designated FA 677 was found to have the highest oleic acid content (i.e.. 80 percent) . Sixty-five seeds from this plant were planted to grow the M5 generation.
- cotyledon analysis For reference purposes, 50 of these 65 seeds were also subjected to cotyledon analysis, which revealed oleic acid levels ranging from 74.0 to 85.0 percent by weight based upon the total fatty acid content.
- the cotyledon analysis-derived profile of the best plant (85.0 percent oleic acid) is shown in the table below:
- Linoleic 18 2 4.4
- the gluconsinolate content in the solid component was 10.94 micromoles per gram.
- the plants produced from the seed are true-breeding upon self-pollination and exhibit a substantially uniform phenotype.
- the average oleic acid content of all of the samples analyzed was 77.1 percent by weight based upon the total fatty acid content indicating a stably high oleic acid level in all descendents of the plant designated FA 677. Further selections using the FA677-39 breeding line can result in the identification of plants exhibiting even higher oleic acid contents. These plants can be preserved and multiplied using conventional techniques.
- the increased oleic acid content renders the rapeseeds capable of providing a vegetable oil of increased stability when exposed to heat. Accordingly, the resulting oil can reliably be used for food-frying applications for a more extended period of time without deleterious results when compared to the canola oil of the prior art. Also, the reduced alpha-linolenic acid content of the resulting vegetable oil imparts enhanced oxidative stability to the same.
- Comparable rapeseed seeds of the M5 generation designated FA 677-39 have been deposited under the Budapest Treaty in the American Type Culture Collection, 12301 Parklawn Drive, Rockville, Maryland 20852, U.S.A., on December 31, 1987. This seed deposit has received Accession No. 40409, and will be made available upon the maturation of this application into a patent. However, the availability of these seeds is not to be construed as a license to practice this invention in contravention of the rights granted under the authority of any government in accordance with its patent or breeder's rights laws.
- Seeds (i.e. f the M2 generation) were next harvested from 153 plants (i.e.. the Ml plants) . Ten seeds from each of the plants were individually analyzed by the halfseed analysis previously described. A total of 276 cotyledon selections were obtained having an oleic acid level of 77 percent by weight or higher based upon the total fatty acid content. Three of these selections were found to contain an oleic acid content of 84 percent by weight based upon the total fatty acid content.
- the remaining cotyledons from the 276 selections were planted in a greenhouse at Georgetown, Ontario, Canada having a day temperature of approximately 25 ⁇ 3°C. and a night temperature of approximately 18 ⁇ C, plants were formed, and seeds were formed as the result of self-pollination (i.e.. the M3 generation following mutagenesis while employing a chemical mutagen) .
- a selection designated FA677M5- 132 in the M3 generation was found to exhibit while using two random 50 seed bulk analyses an oleic acid content of 81.9 percent by weight based upon the total fatty acid content, an alpha-linolenic acid content of 4.03 percent by weight based upon the total acid content, a non-detectible erucic acid content, a saturated fatty acid content of 6.59 percent by weight in the form of stearic and palmitic acids based upon the total fatty acid content, and a glucosinolate content in the solid component of less than 30 micromoles per gram.
- the plants resulting from the germination of the seeds exhibited a substantially uniform phenotype.
- Comparable rapeseeds of the M3 generation designated FA677M5-132 have been deposited under the Budapest Treaty in the American Type Culture Collection, 12301 Parklawn Drive, Rockville, Maryland 20852, U.S.A., on December 13, 1988. This seed deposit has received Accession No. 40523, and will be made available upon the maturation of this application into a patent. However, the availability of these seeds is not to be construed as a license to practice this invention in contravention of the rights granted under the authority of any government in accordance with its patent or breeder's rights laws.
- Topas variety of Brassica napus were selected as the starting material. This variety of canola is of the summer type and is suitable to produce vegetable oil when grown in the United States, Canada, Sweden, and other areas where summer rape is adapted. The Topas variety was registered in 1987 by Svaldof AB of Sweden. Planting seed for this variety is available from Bonis & Company Ltd. of Lindsay, Ontario, Canada. This variety typically exhibits an oleic acid content of approximately 65 percent by weight based upon the total fatty acid content and an alpha-linolenic acid content of approximately 8 percent by weight based upon the total fatty acid content.
- Ten thousand seeds of the Topas variety were subjected to mutagenesis while employing a chemical mutagen. More specifically, seed lots were formed consisting of 1,000 seeds each and were treated with ethylnitrosourea as previously described. The resulting seeds were planted in flats present in a greenhouse containing a soilless greenhouse growing media. 500 seeds were planted in each flat and can be termed Ml seeds. Seeds (i.e.. the M2 generation) were formed as the result of self-pollination on 111 surviving fertile plants (i.e.. the Ml plants) .
- M2 seeds when subjected to cotyledon analysis exhibited on oleic acid content of 82.07 percent by weight and an alpha-linolenic acid content of 5.12 percent by weight based upon the total fatty acid content.
- the remaining M2 cotyledon was planted in a greenhouse at Georgetown, Ontario, Canada, having a day temperature of approximately 25 * ⁇ 3°C. and a night temperature of approximately 18 C C, a plant was formed, and seeds were formed as the result of self-pollination (i.e.. the M3 generation) .
- This M3 generation was designated Topas H6-90 and was found to exhibit while using two random 50 seed bulk analyses an oleic acid content of 81.17 percent by weight based upon the total fatty acid content, an alpha-linolenic acid content of 3.55 percent by weight based upon the total fatty acid content, a non-detectible erucic acid content, a saturated fatty acid content of 6.17 percent by weight in the form of stearic and palmitic acids based upon the total fatty acid content, and a glucosinolate content in the solid component of less than 30 micromoles per gram.
- the plants resulting from the germination of the seeds exhibited a substantially uniform phenotype. Further selections from within the Topas H6-90 breeding line (as indicated hereafter) will result in the identification of plants exhibiting even higher oleic acid contents. These plants can be preserved and multiplied using conventional techniques.
- Topas H6-90-99 a selection identified as Topas H6-90-99 containing the following fatty acids in the approximate concentrations indicated based upon the total fatty acids present while using the same gas liquid chromatography analysis technique previously described:
- Seeds produced from H6-90-99 will continue to exhibit a glucosinolate content in the solid component of less than 30 micromoles per gram.
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Abstract
On décrit des plants de colza améliorés et leurs graines, ainsi qu'une nouvelle huile végétale améliorée dérivée desdites graines de colza. Lesdits plants fournissent une huile végétale qui présente, entre autres caractéristiques avantageuses, une meilleure stabilité thermique due à la présence dans les graines de colza d'une teneur en acide oléique exceptionnellement élevée, qui faisait défaut jusqu'à présent chez les plants de colza connus à ce jour. On a découvert que les plants de colza nouveaux de la présente invention peuvent être créés par une mutogénèse suivie d'une sélection, telles qu'elles ont été décrites dans l'invention. L'huile végétale que produisent les plants de colza améliorés convient tout particulièrement comme huile de friture où la stabilité accrue à des températures élevées est d'importance capitale. Dans un mode de réalisation préférentiel, où l'huile végétale est utilisée comme huile de friture, la teneur en acide alpha-linolénique est réduite simultanément, ce qui apporte également une meilleure stabilité d'oxydation.
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP89503152A JPH05505512A (ja) | 1989-03-06 | 1989-03-06 | 増大されたオレイン酸含量を示す改良されたナタネの生産 |
PCT/US1989/000835 WO1990010380A1 (fr) | 1989-03-06 | 1989-03-06 | Production d'une huile de colza amelioree presentant une teneur en acide oleique accrue |
BR898907882A BR8907882A (pt) | 1989-03-06 | 1989-03-06 | Producao de sementes de colza que apresentam um acentuado teor de acido oleico |
KR1019910700994A KR920702813A (ko) | 1989-03-06 | 1989-03-06 | 증가된 올레인산 함량을 내타내는 개량된 평지종자씨의 생산 |
AU63309/90A AU642907B2 (en) | 1989-03-06 | 1989-03-06 | Production of improved rapeseed exhibiting an enhanced oleic acid content |
NO913434A NO307401B1 (no) | 1989-03-06 | 1991-09-02 | Fremgangsmåte ved fremstilling av en endogen vegetabilsk olje |
FI914183A FI914183A0 (fi) | 1989-03-06 | 1991-09-04 | Foerfarande foer producering av raps- korn med hoegre oleinsyrahalt. |
DK199101557A DK175657B1 (da) | 1989-03-06 | 1991-09-05 | Fremgangsmåde til frembringelse af en endogen vegetabilsk olie |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1989/000835 WO1990010380A1 (fr) | 1989-03-06 | 1989-03-06 | Production d'une huile de colza amelioree presentant une teneur en acide oleique accrue |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1990010380A1 true WO1990010380A1 (fr) | 1990-09-20 |
Family
ID=22214858
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1989/000835 WO1990010380A1 (fr) | 1989-03-06 | 1989-03-06 | Production d'une huile de colza amelioree presentant une teneur en acide oleique accrue |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPH05505512A (fr) |
KR (1) | KR920702813A (fr) |
AU (1) | AU642907B2 (fr) |
BR (1) | BR8907882A (fr) |
DK (1) | DK175657B1 (fr) |
FI (1) | FI914183A0 (fr) |
WO (1) | WO1990010380A1 (fr) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993006714A1 (fr) * | 1991-09-30 | 1993-04-15 | E.I. Du Pont De Nemours And Company | Variete de colza produisant une graine a teneur reduite en glucosinolates et en acide linolenique et permettant d'obtenir une huile a faible teneur en soufre, a caracteristiques organoleptiques ameliorees et a stabilite amelioree a l'oxydation |
US5530192A (en) * | 1993-03-31 | 1996-06-25 | Mitsubishi Corporation | Oilseed crops producing valuable seeds having altered amino acid composition and fatty acid composition |
US5625130A (en) * | 1995-03-07 | 1997-04-29 | Pioneer Hi-Bred International, Inc. | Oilseed Brassica bearing an endogenous oil wherein the levels of oleic, alpha-linolenic, and saturated fatty acids are simultaneously provided in an atypical highly beneficial distribution via genetic control |
EP0771878A1 (fr) * | 1995-10-31 | 1997-05-07 | Plant Genetic Systems N.V. | Plantes à teneur réduite en glucosinolates |
US5750827A (en) * | 1991-09-30 | 1998-05-12 | Cargill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US5767338A (en) * | 1993-04-27 | 1998-06-16 | Cargill, Incorporated | Brassica napus plants which produce non-hydrogenated canola oil for food applications |
US5885643A (en) * | 1996-05-21 | 1999-03-23 | Cargill, Incorporated | High stability canola oils |
US6063947A (en) * | 1996-07-03 | 2000-05-16 | Cargill, Incorporated | Canola oil having increased oleic acid and decreased linolenic acid content |
US6270828B1 (en) | 1993-11-12 | 2001-08-07 | Cargrill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US6372965B1 (en) | 1992-11-17 | 2002-04-16 | E.I. Du Pont De Nemours And Company | Genes for microsomal delta-12 fatty acid desaturases and hydroxylases from plants |
US6872872B1 (en) | 1992-11-17 | 2005-03-29 | E. I. Du Pont De Nemours And Company | Genes for microsomal delta-12 fatty acid desaturases and related enzymes from plants |
CN114196471A (zh) * | 2021-12-10 | 2022-03-18 | 中国农业科学院油料作物研究所 | 一种浓香菜籽油的制备方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109042308A (zh) * | 2018-09-26 | 2018-12-21 | 周口师范学院 | 一种油菜诱变育种方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK0476093T3 (da) * | 1990-04-04 | 1997-06-02 | Pioneer Hi Bred Int | Fremstilling af forbedret rapsfrø, der udviser et reduceret indhold af mættet fedtsyre |
-
1989
- 1989-03-06 WO PCT/US1989/000835 patent/WO1990010380A1/fr active Application Filing
- 1989-03-06 BR BR898907882A patent/BR8907882A/pt not_active Application Discontinuation
- 1989-03-06 JP JP89503152A patent/JPH05505512A/ja active Pending
- 1989-03-06 KR KR1019910700994A patent/KR920702813A/ko not_active Ceased
- 1989-03-06 AU AU63309/90A patent/AU642907B2/en not_active Expired
-
1991
- 1991-09-04 FI FI914183A patent/FI914183A0/fi unknown
- 1991-09-05 DK DK199101557A patent/DK175657B1/da not_active IP Right Cessation
Non-Patent Citations (7)
Title |
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FAT SCIENCE TECHNOLOGY, Volume 90, issued May 1988, (Berlin, West Germany), PLEINES, "Breeding for Improved C18-fatty Acid Composition in Rapeseed," pages 167-171. * |
INDIAN JOURNAL OF AGRICULTURAL SCIENCE, Volume 48, issued July 1978, (New Delhi, India), RAHMAN L., "Relationships Between Major Fatty Acids of Oleiferous Species of Brassica", page 401-406. * |
JOURNAL OF AMERICAN OIL CHEMISTS SOCIETY, Volume 50, issued October 1973, (Champaign, Illinois, USA), RAKOW, "Opportunities and Problems in Modification of Levels of Rapeseed C18 Unsaturated Fatty Acids", pages 400-403. * |
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THE INDIAN JOURNAL OF NUTRITION AND DIETETICS, Volume 13, issued October 1976, (Coimbatore, India), SRIVASTAVA, "Comparison of Some Chemical Characteristics of Indian and Canadian Brassica Seeds", pages 336-342. * |
ZEITSCHRIFT FUR PFLANZENZUCHTUNG, Volume 75, issued June 1975, (Berlin, West Germany), ROBBELEN, "Genetical and Physiological Investigations on Mutants for Polyenoic Fatty Acids in Rapeseed", pages 93-105. * |
ZEITSCHRIFT FUR PFLANZENZUCHTUNG, Volume 95, issued September 1985, (Berlin, West Germany), ROY, "IXLIN- an Interspecific Source for High Linoleic and Low Linolenic Acid Content in Rapeseed", pages 201-209. * |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
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US6680396B2 (en) | 1991-09-30 | 2004-01-20 | Cargill Incorporated | Canola oil with reduced linolenic acid |
EP0779024A3 (fr) * | 1991-09-30 | 1999-03-17 | Cargill Incorporated | Variété de colza produisant une graine à teneur réduite en glucosinolates et en acide linolénique et permettant d'obtenir une huile à faible teneur en soufre, à caractéristiques organoleptiques améliorées et à stabilité améliorée à l'oxydation |
US6562397B2 (en) | 1991-09-30 | 2003-05-13 | Cargill, Incoporated | Canola meal having reduced glucosinolates |
US5859350A (en) * | 1991-09-30 | 1999-01-12 | Cargill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid |
EP1354509A1 (fr) * | 1991-09-30 | 2003-10-22 | Cargill, Incorporated | Variété de colza produisant une graine à teneur réduite en glucosinolates et en acide linolénique et permettant d'obtenir une huile à faible teneur en soufre, à caractéristiques organoleptiques améliorées et à stabilité améliorée à l'oxydation |
EP0779024A2 (fr) * | 1991-09-30 | 1997-06-18 | Cargill Incorporated | Variété de colza produisant une graine à teneur réduite en glucosinolates et en acide linolénique et permettant d'obtenir une huile à faible teneur en soufre, à caractéristiques organoleptiques améliorées et à stabilité améliorée à l'oxydation |
US5750827A (en) * | 1991-09-30 | 1998-05-12 | Cargill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
WO1993006714A1 (fr) * | 1991-09-30 | 1993-04-15 | E.I. Du Pont De Nemours And Company | Variete de colza produisant une graine a teneur reduite en glucosinolates et en acide linolenique et permettant d'obtenir une huile a faible teneur en soufre, a caracteristiques organoleptiques ameliorees et a stabilite amelioree a l'oxydation |
US6689409B2 (en) | 1991-09-30 | 2004-02-10 | Cargill, Incorporated | Canola oil with reduced linolenic acid |
US6872872B1 (en) | 1992-11-17 | 2005-03-29 | E. I. Du Pont De Nemours And Company | Genes for microsomal delta-12 fatty acid desaturases and related enzymes from plants |
US6919466B2 (en) | 1992-11-17 | 2005-07-19 | E. I. Du Pont De Nemours And Company | Genes for microsomal delta-12 fatty acid desaturases and related enzymes from plants |
US6372965B1 (en) | 1992-11-17 | 2002-04-16 | E.I. Du Pont De Nemours And Company | Genes for microsomal delta-12 fatty acid desaturases and hydroxylases from plants |
US7105721B2 (en) | 1992-11-17 | 2006-09-12 | E. I. Du Pont De Nemours And Company | Genes for microsomal delta-12 fatty acid desaturases and hydroxylases from plants |
US5530192A (en) * | 1993-03-31 | 1996-06-25 | Mitsubishi Corporation | Oilseed crops producing valuable seeds having altered amino acid composition and fatty acid composition |
US6559325B2 (en) | 1993-04-27 | 2003-05-06 | Cargill, Incorporated | Non-hydrogenated canola oil for food applications |
US5767338A (en) * | 1993-04-27 | 1998-06-16 | Cargill, Incorporated | Brassica napus plants which produce non-hydrogenated canola oil for food applications |
US5969169A (en) * | 1993-04-27 | 1999-10-19 | Cargill, Incorporated | Non-hydrogenated canola oil for food applications |
US6201145B1 (en) | 1993-04-27 | 2001-03-13 | Cargill, Incorporated | Non-hydrogenated canola oil for food applications |
US6407317B2 (en) | 1993-04-27 | 2002-06-18 | Cargill, Incorporated | Non-hydrogenated canola oil for food applications |
US7238852B2 (en) | 1993-04-27 | 2007-07-03 | Cargill, Incorporated | Non-hydrogenated canola oil for food applications |
US6270828B1 (en) | 1993-11-12 | 2001-08-07 | Cargrill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US6011164A (en) * | 1995-03-07 | 2000-01-04 | Pioneer Hi-Bred International, Inc. | Brassica napus vegetable oil wherein the levels of oleic, alpha-linolenic, and saturated fatty acids are endogenously formed and are simultaneously provided in an atypical highly beneficial distribution via genetic control |
US5955623A (en) * | 1995-03-07 | 1999-09-21 | Pioneer Hi-Bred International, Inc. | Brassica napus vegetable oil wherein the levels of oleic, alpha-linolenic, and saturated fatty acids are endogenously formed and simultaneously provided in an atypical highly beneficial distribution via genetic control |
US5625130A (en) * | 1995-03-07 | 1997-04-29 | Pioneer Hi-Bred International, Inc. | Oilseed Brassica bearing an endogenous oil wherein the levels of oleic, alpha-linolenic, and saturated fatty acids are simultaneously provided in an atypical highly beneficial distribution via genetic control |
WO1997016559A1 (fr) * | 1995-10-31 | 1997-05-09 | Plant Genetic Systems, N.V. | Plantes presentant une teneur reduite en glucosinolate |
EP0771878A1 (fr) * | 1995-10-31 | 1997-05-07 | Plant Genetic Systems N.V. | Plantes à teneur réduite en glucosinolates |
US5885643A (en) * | 1996-05-21 | 1999-03-23 | Cargill, Incorporated | High stability canola oils |
US6441278B1 (en) | 1996-07-03 | 2002-08-27 | Cargill Incorporated | Canola oil having increased oleic acid and decreased linolenic acid content |
US6583303B1 (en) | 1996-07-03 | 2003-06-24 | Cargill, Incorporated | Canola oil having increased oleic acid and decreased linolenic acid content |
US6063947A (en) * | 1996-07-03 | 2000-05-16 | Cargill, Incorporated | Canola oil having increased oleic acid and decreased linolenic acid content |
US7741542B2 (en) | 1996-07-03 | 2010-06-22 | Cargill, Incorporated | Canola oil having increased oleic acid and decreased linolenic acid content |
CN114196471A (zh) * | 2021-12-10 | 2022-03-18 | 中国农业科学院油料作物研究所 | 一种浓香菜籽油的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
FI914183A0 (fi) | 1991-09-04 |
DK155791A (da) | 1991-09-05 |
DK155791D0 (da) | 1991-09-05 |
KR920702813A (ko) | 1992-10-28 |
JPH05505512A (ja) | 1993-08-19 |
BR8907882A (pt) | 1992-11-10 |
DK175657B1 (da) | 2005-01-10 |
AU642907B2 (en) | 1993-11-04 |
AU6330990A (en) | 1990-10-09 |
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