CN117025307A - Grease rich in hexadecaneenoic acid and hexadecanedienoic acid, preparation method and application - Google Patents
Grease rich in hexadecaneenoic acid and hexadecanedienoic acid, preparation method and application Download PDFInfo
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- CN117025307A CN117025307A CN202310988291.9A CN202310988291A CN117025307A CN 117025307 A CN117025307 A CN 117025307A CN 202310988291 A CN202310988291 A CN 202310988291A CN 117025307 A CN117025307 A CN 117025307A
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- Prior art keywords
- acid
- grease
- hexadecaneenoic
- hexadecanedienoic
- rich
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- 239000004519 grease Substances 0.000 title claims abstract description 46
- ZVRMGCSSSYZGSM-UHFFFAOYSA-N hexadec-2-enoic acid Chemical compound CCCCCCCCCCCCCC=CC(O)=O ZVRMGCSSSYZGSM-UHFFFAOYSA-N 0.000 title claims description 14
- OOJGMLFHAQOYIL-UHFFFAOYSA-N hexadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCC=CC=CC(O)=O OOJGMLFHAQOYIL-UHFFFAOYSA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title abstract description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 32
- 235000012343 cottonseed oil Nutrition 0.000 claims abstract description 31
- 239000002385 cottonseed oil Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 17
- 235000021314 Palmitic acid Nutrition 0.000 claims abstract description 16
- 230000009261 transgenic effect Effects 0.000 claims abstract description 14
- OOJGMLFHAQOYIL-SQIWNDBBSA-N (2e,4e)-hexadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C(O)=O OOJGMLFHAQOYIL-SQIWNDBBSA-N 0.000 claims abstract description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 12
- 235000019198 oils Nutrition 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- 239000006041 probiotic Substances 0.000 claims description 9
- 235000018291 probiotics Nutrition 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000344 soap Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 239000011363 dried mixture Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 210000000936 intestine Anatomy 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 238000007664 blowing Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004042 decolorization Methods 0.000 claims description 2
- 230000001877 deodorizing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000010583 slow cooling Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 7
- 230000006870 function Effects 0.000 abstract description 5
- 230000007413 intestinal health Effects 0.000 abstract description 5
- 230000004048 modification Effects 0.000 abstract description 3
- 238000012986 modification Methods 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract description 3
- 238000005194 fractionation Methods 0.000 abstract description 2
- 238000005809 transesterification reaction Methods 0.000 abstract description 2
- 241000700159 Rattus Species 0.000 description 30
- 230000000968 intestinal effect Effects 0.000 description 13
- 230000000694 effects Effects 0.000 description 10
- 241000186000 Bifidobacterium Species 0.000 description 8
- 241000186660 Lactobacillus Species 0.000 description 8
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound 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 8
- 229940039696 lactobacillus Drugs 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 208000008589 Obesity Diseases 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 239000003925 fat Substances 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 7
- 235000020824 obesity Nutrition 0.000 description 7
- 210000003608 fece Anatomy 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 210000000028 corpus adiposum pararenale Anatomy 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 4
- 229940090949 docosahexaenoic acid Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 201000010063 epididymitis Diseases 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 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 3
- 238000010171 animal model Methods 0.000 description 3
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 3
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 3
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 238000007619 statistical method Methods 0.000 description 3
- 241000606125 Bacteroides Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 210000001596 intra-abdominal fat Anatomy 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 108050003185 3-oxoacyl-[acyl-carrier-protein] synthase 2 Proteins 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000203069 Archaea Species 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 241000305071 Enterobacterales Species 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
- 241000186394 Eubacterium Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- 241000590002 Helicobacter pylori Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 241000605894 Porphyromonas Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 108091030071 RNAI Proteins 0.000 description 1
- 241000192031 Ruminococcus Species 0.000 description 1
- 238000010162 Tukey test Methods 0.000 description 1
- 241001261005 Verrucomicrobia Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 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 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009045 body homeostasis Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000013367 dietary fats Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000009368 gene silencing by RNA Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 244000005709 gut microbiome Species 0.000 description 1
- 229940037467 helicobacter pylori Drugs 0.000 description 1
- SZQQHKQCCBDXCG-UHFFFAOYSA-N hexadeca-2,4,6-trienoic acid Chemical compound CCCCCCCCCC=CC=CC=CC(O)=O SZQQHKQCCBDXCG-UHFFFAOYSA-N 0.000 description 1
- 238000012165 high-throughput sequencing Methods 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000002490 intestinal epithelial cell Anatomy 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 238000006241 metabolic reaction Methods 0.000 description 1
- 230000000696 methanogenic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000000110 microvilli Anatomy 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229930001119 polyketide Natural products 0.000 description 1
- 150000003881 polyketide derivatives Chemical class 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Mycology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
The invention provides grease rich in hexadecanoic acid and hexadecadienoic acid, wherein the content percentage of hexadecanoic acid in the grease is 27%, and the content percentage of hexadecadienoic acid in the grease is 10%; the invention provides a preparation method and application of grease rich in hexadecanoic acid and hexadecadienoic acid, and the transgenic cottonseed oil treated by a modification process is obtained by carrying out processes such as fractionation, transesterification and the like on the transgenic cottonseed oil, namely the grease rich in hexadecanoic acid and hexadecadienoic acid, and meanwhile, the grease has the functions of losing weight and promoting intestinal health.
Description
Technical Field
The invention relates to the technical field of edible oil, in particular to oil rich in hexadecanoic acid and hexadecadienoic acid, a preparation method thereof and application of the oil in reducing the weight of a subject and improving the abundance of probiotics in intestines and stomach of the subject.
Background
Cottonseed oil is an important edible oil for residents in cotton main production areas, and although the cottonseed oil contains unsaturated fatty acids such as oleic acid, linolenic acid and the like which are beneficial to the health of the body, the physiological functions of the cottonseed oil are relatively less compared with those of other vegetable oils such as olive oil, linseed oil, sunflower seed oil and the like, so that the application of the cottonseed oil in terminal foods is limited.
In recent years, the development of transgenic technology has enabled specific plant seeds to produce specific functional fatty acids. For example, the transgenic technology by the United states Dow and Royal Imperial Netherlands produced DHA (docosahexaenoic acid) and EPA (eicosapentaenoic acid) polyunsaturated fatty acids (Walsh, T.A.), bevan, S.A., gachote, D.J., larsen, C.M., moskal, W.A., merlo, P.A., … Metz, J.G. (2016), canola engineered with a microalgal polyketide synthase-like system produces oil enriched in docosahexaenoic acid. Nature technology,34 (8), 881-887.Doi: 10.1038/nbt.3585). DHA and EPA were previously mainly derived from algae oil and deep sea fish oil. This technology increases the commercial value of canola oil.
Transgenic cottonseed has been made by researchers to obtain cottonseed oils containing C16:1 and C16:2 (Liu, Q., wu, M., zhang, B., shretha, P., petrie, J., green, A.G., & Singh, S.P. (2016), genetic enhancement of palmitic acid accumulation in cotton seed oil through RNAi down-regulation ofghKAS 2.2 encoding beta-ketoacyl-ACP synthase II (KASII), plant Biotechnology Journal,15 (1), 132-143.doi:10.1111/pbi.12598). However, there is no report on what function the grease has. How to fully and efficiently comprehensively develop and utilize the functions of the cottonseed oil, not only can create higher economic value, but also has important social significance.
In recent decades, due to the development of economy and society and unhealthy living habits of people, the incidence of obesity has increased dramatically, and World Health Organization (WHO) statistics indicate that the incidence of obesity worldwide in 2016 is almost three times that in 1975, and obesity has become a public health problem commonly faced by all people. In 2016, over 6 million adults had obesity worldwide. Obesity is closely related to the composition of fat and fatty acids in the diet. Such as palm oil and palmitic acid, are among the factors responsible for obesity. Therefore, fat with a fat-reducing function is favored by consumers.
1000-1150 bacteria (100 trillion bacteria) are in intestinal tract of human body, which is 10 times of the number of human body cells, and each human body has at least 160 dominant bacterial groups. Of the gastrointestinal bacteria of healthy humans, more than 90% of the species of the phylum bacteroides and the phylum firmicutes, including bacteroides, praecox, porphyromonas, clostridium, eubacterium, ruminococcus, lactobacillus, and the like. Other less abundant species are actinomycota (bifidobacterium and chrysogenum), proteus (enterobacteriaceae, helicobacter pylori, hua saxobacteria), verrucomicrobia, methanogenic archaea, and the like. Lactobacillus and Bifidobacterium are well known probiotics and play a critical role in host intestinal health.
The relationship between intestinal bacteria and hosts is reciprocal symbiotic, and the intestinal flora is important for the health of intestinal tracts, the maintenance of body homeostasis and the protection of human bodies against foreign pathogens. The intestinal flora participates in metabolic reactions and also plays a fundamental role in the maturation of the immune response of the host by promoting the growth of intestinal microvilli, thus producing a nutritional effect on intestinal epithelial cells. When the intestinal flora balance is disturbed, the host may cause corresponding diseases such as: obesity, diabetes, cardiovascular and cerebrovascular diseases, inflammatory enteritis, gastrointestinal cancer, autoimmune diseases, irritable bowel syndrome, liver cirrhosis, etc.
Recent studies have shown that dietary fats and fatty acids have a certain influence on the composition of intestinal microorganisms. Therefore, it is important to maintain intestinal health by diet.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides grease rich in hexadecaneenoic acid and hexadecanedienoic acid, a preparation method and application thereof, and aims to solve the problems.
In order to achieve the above purpose, the present invention provides the following technical solutions:
the invention provides grease rich in hexadecanoic acid and hexadecadienoic acid, wherein the content percentage of hexadecanoic acid in the grease is 27%, and the content percentage of hexadecadienoic acid in the grease is 10%.
The invention also provides a preparation method of the grease rich in hexadecaneenoic acid and hexadecanedienoic acid, which comprises the following steps:
s1, adding 4 times of acetone into raw materials for mixing, heating to 60 ℃, stirring for 10 minutes, and slowly cooling;
s2, continuously stirring for 60 minutes after the temperature is set to 30 ℃, and then filtering the mixed liquid and removing acetone to obtain an oil part;
s3, heating the obtained grease to 105 ℃, carrying out vacuum stirring for dehydration, and then adding 0.5% sodium methoxide for reaction at the temperature of 100 ℃;
s4, adding a citric acid aqueous solution accounting for 20% of the total weight of the mixture, and stirring for 20min to terminate the reaction;
s5, repeatedly washing the reactant with hot water until the PH=7, and then, performing soap removal;
s6, heating the reaction product after the soap removal to 105 ℃, and carrying out vacuum stirring for 30 minutes to carry out dehydration and drying;
s7, adding activated clay accounting for 2% of the weight of the dehydrated and dried mixture, keeping at 110 ℃ for 30 minutes for decolorization, and then filtering the decolorized grease;
and S8, heating the filtered grease to 240 ℃, deodorizing for 2 hours under the condition of blowing nitrogen to obtain the grease.
Further, the raw material is transgenic cotton seed oil, wherein the content percentage of hexadecanoic acid is 11.2%, and the content percentage of hexadecanoic acid is 2.2%.
Further, the slow cooling rate in S1 is to decrease the temperature by 30℃at a cooling rate of 2℃per minute.
Further, the acetone is removed in S2 by evaporating the acetone by a rotary evaporator.
Further, 0.5% sodium methoxide was added to S3 to conduct the reaction at 100℃for 45 minutes.
Further, the concentration of the aqueous citric acid solution in S4 was 8%.
The invention also provides application of the grease rich in hexadecanoic acid and hexadecadienoic acid in reducing the weight of a subject and improving the abundance of probiotics in intestines and stomach of the subject.
Compared with the prior art, the invention has the following beneficial effects:
according to the grease rich in hexadecanoic acid and hexadecadienoic acid, the preparation method and the application, the transgenic cottonseed oil treated by the modification process is obtained through the processes of fractionation, transesterification and the like of the transgenic cottonseed oil, and meanwhile, the grease has the functions of losing weight and promoting intestinal health.
Drawings
FIG. 1 is a table of fatty acid composition (%) of oils and fats;
FIG. 2 is a table showing the diet and growth of rats during the experiment of the present invention;
FIG. 3 shows the relative abundance of Lactobacillus intestinal bacteria in the faeces of various groups of rats tested according to the invention;
FIG. 4 shows the relative abundance of Bifidobacterium enterobacteria in the faeces of the various groups of rats tested in accordance with the invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Embodiment one: grease rich in hexadecaneenoic acid and hexadecanedienoic acid and preparation method thereof
Transgenic cottonseed oil (GMO-CSO) and non-transgenic cottonseed oil (CSO) are commercially available (their fatty acid compositions are shown in FIG. 1)
The method comprises the steps of taking transgenic cottonseed oil (GMO-CSO: hexadeceneic acid content is 11.2% and hexadecenedienoic acid content is 2.2%) as a raw material, mixing 1 part of transgenic cottonseed oil with 4 parts of acetone, heating to 60 ℃, stirring for 10 minutes, then reducing the temperature of the mixed liquid to 30 ℃ at a temperature reduction rate of 2 ℃ per minute, slowly stirring in the temperature reduction process, continuing stirring for 60 minutes after the temperature reaches 30 ℃, and finally evaporating the mixed liquid by a rotary evaporator to remove the acetone to obtain a liquid oil part.
Secondly, heating the liquid grease to 105 ℃, and stirring in vacuum for 1h to dehydrate; adding 0.5% sodium methoxide, and reacting at 100 ℃ for 45 minutes; an aqueous solution of citric acid (concentration: 8%) was added in an amount of 20% by weight of the above mixture, and the mixture was stirred for 20 minutes to terminate the reaction. The reaction was repeatedly washed with hot water until ph=7, desoaked. Heating to 105 ℃, and vacuum stirring for 30 minutes for dehydration and drying; adding 2% of activated clay by weight of the dehydrated and dried mixture, decolorizing at 110deg.C for 30 min, and filtering to obtain decolorized oil. The oil was deodorized by heating to 240℃with a nitrogen bubbling at 2mbar for 2 hours to give the oil (GMO-CSOOL: hexadecaneenoic acid content: 27% and hexadecanedienoic acid content: 10%).
Embodiment two: application of grease rich in hexadecaneenoic acid and hexadecanedienoic acid
The rats were fed with 15% by weight of cottonseed oil, 15% by weight of transgenic cottonseed oil, and 15% by weight of refined transesterified fat added to a fat-free rat diet for 28 days. After the end of feeding, the weight of each group of rats was compared with the weight of epididymal fat and the weight of perirenal fat and the abundance of Lactobacillus and Bifidobacterium intestinal bacteria in the rat feces was examined.
Feeding experimental example: experimental animals and methods
The study used 21-day male (weaning) SD rats born from specific pathogen-free laboratory animals (SPF grade), 33 total, weight 56+ -2.5 g. All animals were quarantined 7 days prior to entering the formal experiment and all animals were fed animal house standard feed during quarantine. Animal house conditions: SPF-level animal laboratory, constant temperature and humidity, 20-25 ℃, daily temperature difference less than 3 ℃, humidity 40-70%, ventilation times 10-15 times/h, day and night of 12h:12h; sterilizing drinking water, padding and cages at high temperature, and sterilizing feed by cobalt 60 irradiation. Daily feeding management was performed according to the SOP of the SPF class animal laboratory.
Rats were randomly grouped (into 3 groups of 11) from day 29: group a was fed 85% lipid free feed +15% cso oil; group B is fed with 85% of lipid-free feed and 15% of GMO-CSO grease; group C was fed 85% lipid free feed +15% GMO-CSOOL grease. The experimental animals were fed and drinking water freely and kept for 28 days during the experiment. After the completion of the feeding, the rats were transferred to a metabolic cage and fed for 3 days. Rats were free to ingest and drink water during feeding. Fresh feces from each rat were collected separately and kept in a-80℃refrigerator for further use. After 3 days, rats were fasted for 12 hours, weighed, and after injection of pentobarbital (60 mg/kg) as anesthetic, perirenal fat and epididymal fat were weighed and placed in a-80 ℃ refrigerator for storage.
Method for detecting total abundance of Lactobacillus and Bifidobacterium intestinal bacteria. Referring to Fan, wenguang, et al Inantant formula supplemented with low protein and high carbohydrate alters the intestinal microbiota in neonatal SD rates, BMC microbiol 2014;14:279. High throughput sequencing and bioinformatic statistical methods are mentioned herein.
Experimental data are expressed as mean ± variance. Statistical analysis was performed using a one-factor variance and Tukey's multiple comparison test. If the statistics are not normally distributed, the data statistics are analyzed by Kruskal-Wallis analysis. All statistical analyses were done using GraphPad Prism Version 5.0.5.0 software. P <0.05 was considered to have a statistically significant difference.
Example results:
from fig. 2, it can be seen that there was no significant difference in the initial body weight of each group of rats before the start of the test, while there was no significant difference in the feed intake of each group of rats in the feeding test for 4 weeks. No significant difference was observed in the final body weight between the rat groups of group a (containing CSO) and group B (containing GMO-CSO); but group C (GMO-CSOOL-containing grease) rats had lower final body weight than group a (CSO-containing) and group B (GMO-CSO). The results indicate that GMO-CSOOL has the effect of reducing body weight in rats.
From fig. 2, it can be seen that there was no significant difference in epididymal fat weight between the rat group of group a (containing CSO) and group B (containing GMO-CSO); but group C (GMO-CSOOL-containing grease) rats had lower final body weight than group a (CSO-containing) and group B (GMO-CSO). The results show that GMO-CSOOL has the effect of reducing the weight of epididymal fat of rats.
From fig. 2, it can be seen that there was no significant difference in perirenal fat weight between the rat groups of group a (containing CSO) and group B (containing GMO-CSO); but group C (GMO-CSOOL-containing grease) rats had lower final body weight than group a (CSO-containing) and group B (GMO-CSO). The results indicate that GMO-CSOOL has the effect of reducing the weight of perirenal fat in rats.
The above results indicate that GMO-CSO does not have the effect of reducing body weight and visceral fat. However, after the GMO-CSO is modified by the grease, the GMO-CSOOL has the effect of reducing the weight and the visceral fat.
Lactobacillus and Bifidobacterium are well known probiotics and play a critical role in host intestinal health. This example found no significant difference in Lactobacillus abundance (FIG. 3), in the groups of rats of group A (containing CSO) and group B (containing GMO-CSO); however, the relative abundance of Lactobacillus in the faeces of rats in group C (containing GMO-CSOOL grease) was high compared to groups A (containing CSO) and B (GMO-CSO). The results show that GMO-CSOOL has the effect of increasing the intestinal probiotics in rats.
No significant difference in Bifidobacterium abundance (fig. 4), groups of rats in group a (containing CSO) and group B (containing GMO-CSO); however, the relative abundance of Bifidobacterium in the faeces of rats in group C (containing GMO-CSOOL grease) was high compared to those in groups A (containing CSO) and B (GMO-CSO). The result shows that the GMO-CSOOL has the effect of increasing the intestinal probiotics of rats.
The above results indicate that GMO-CSO does not have an effect of increasing intestinal probiotics. However, after the GMO-CSO is modified by grease, the GMO-CSOOL has the effect of increasing intestinal probiotics.
It is noted that relational terms such as first and second, and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising one … …" does not exclude the presence of other like elements in a process, method, article, or apparatus that comprises the element.
In the description of the present invention, unless otherwise indicated, the meaning of "a plurality" is two or more; the terms "upper," "lower," "left," "right," "inner," "outer," "front," "rear," "head," "tail," and the like are used as an orientation or positional relationship based on that shown in the drawings, merely to facilitate description of the invention and to simplify the description, and do not indicate or imply that the devices or elements referred to must have a particular orientation, be constructed and operated in a particular orientation, and therefore should not be construed as limiting the invention.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (8)
1. The grease rich in hexadecanoic acid and hexadecadienoic acid is characterized in that the content percentage of hexadecanoic acid in the grease is 27%, and the content percentage of hexadecadienoic acid in the grease is 10%.
2. The method for producing a hexadecanedioic acid and hexadecanedioic acid enriched grease according to claim 1, comprising the steps of:
s1, adding 4 times of acetone into raw materials for mixing, heating to 60 ℃, stirring for 10 minutes, and slowly cooling;
s2, continuously stirring for 60 minutes after the temperature is set to 30 ℃, and then filtering the mixed liquid and removing acetone to obtain an oil part;
s3, heating the obtained grease to 105 ℃, carrying out vacuum stirring for dehydration, and then adding 0.5% sodium methoxide for reaction at the temperature of 100 ℃;
s4, adding a citric acid aqueous solution accounting for 20% of the total weight of the mixture, and stirring for 20min to terminate the reaction;
s5, repeatedly washing the reactant with hot water until the PH=7, and then, performing soap removal;
s6, heating the reaction product after the soap removal to 105 ℃, and carrying out vacuum stirring for 30 minutes to carry out dehydration and drying;
s7, adding activated clay accounting for 2% of the weight of the dehydrated and dried mixture, keeping at 110 ℃ for 30 minutes for decolorization, and then filtering the decolorized grease;
and S8, heating the filtered grease to 240 ℃, deodorizing for 2 hours under the condition of blowing nitrogen to obtain the grease.
3. The method for preparing the grease rich in hexadecaneenoic acid and hexadecanedienoic acid according to claim 2, characterized in that: the raw material is transgenic cottonseed oil, wherein the content percentage of hexadecanoic acid is 11.2%, and the content percentage of hexadecanoic dienoic acid is 2.2%.
4. The method for preparing the grease rich in hexadecaneenoic acid and hexadecanedienoic acid according to claim 2, characterized in that: the slow cooling rate in S1 is to decrease the temperature by 30 ℃ at a cooling rate of 2 ℃ per minute.
5. The method for preparing the grease rich in hexadecaneenoic acid and hexadecanedienoic acid according to claim 2, characterized in that: the acetone is removed in S2 by evaporation with a rotary evaporator.
6. The method for preparing the grease rich in hexadecaneenoic acid and hexadecanedienoic acid according to claim 2, characterized in that: s3 is added with 0.5% sodium methoxide and the reaction time is 45 minutes at 100 ℃.
7. The method for preparing the grease rich in hexadecaneenoic acid and hexadecanedienoic acid according to claim 2, characterized in that: the concentration of the aqueous citric acid solution in S4 was 8%.
8. Use of a lipid enriched in hexadecaneenoic acid and hexadecanedienoic acid according to claim 1 for reducing the weight of a subject and increasing the abundance of probiotics in the intestines and stomach of a subject.
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