CN117837758A - Amorphous phytosterol with improved solubility and preparation method thereof - Google Patents
Amorphous phytosterol with improved solubility and preparation method thereof Download PDFInfo
- Publication number
- CN117837758A CN117837758A CN202410265001.2A CN202410265001A CN117837758A CN 117837758 A CN117837758 A CN 117837758A CN 202410265001 A CN202410265001 A CN 202410265001A CN 117837758 A CN117837758 A CN 117837758A
- Authority
- CN
- China
- Prior art keywords
- phytosterol
- nicotinamide
- amorphous
- drying
- ligand
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003446 ligand Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000001694 spray drying Methods 0.000 claims abstract description 19
- 235000013305 food Nutrition 0.000 claims abstract description 11
- 238000010025 steaming Methods 0.000 claims abstract description 11
- 238000004108 freeze drying Methods 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 4
- 230000036541 health Effects 0.000 claims abstract description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 54
- 229960003966 nicotinamide Drugs 0.000 claims description 40
- 239000011570 nicotinamide Substances 0.000 claims description 40
- 235000005152 nicotinamide Nutrition 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 15
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 235000002378 plant sterols Nutrition 0.000 claims description 9
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 6
- 239000004475 Arginine Substances 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 6
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 6
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 6
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 6
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 6
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 6
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 6
- 229960000310 isoleucine Drugs 0.000 claims description 6
- 239000000832 lactitol Substances 0.000 claims description 6
- 229960003451 lactitol Drugs 0.000 claims description 6
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 claims description 6
- 235000010448 lactitol Nutrition 0.000 claims description 6
- 235000011090 malic acid Nutrition 0.000 claims description 6
- 239000001630 malic acid Substances 0.000 claims description 6
- 229960003121 arginine Drugs 0.000 claims description 5
- 229940099690 malic acid Drugs 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 229960003487 xylose Drugs 0.000 claims description 5
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims description 4
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000889 atomisation Methods 0.000 claims description 4
- 229940076810 beta sitosterol Drugs 0.000 claims description 4
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 4
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 4
- 229950005143 sitosterol Drugs 0.000 claims description 4
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims description 4
- 235000016831 stigmasterol Nutrition 0.000 claims description 4
- 229940032091 stigmasterol Drugs 0.000 claims description 4
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 3
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 239000004386 Erythritol Substances 0.000 claims description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 3
- 229930091371 Fructose Natural products 0.000 claims description 3
- 239000005715 Fructose Substances 0.000 claims description 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 3
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 229960005070 ascorbic acid Drugs 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 235000000431 campesterol Nutrition 0.000 claims description 3
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims description 3
- 235000015165 citric acid Nutrition 0.000 claims description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 3
- 229940009714 erythritol Drugs 0.000 claims description 3
- 235000019414 erythritol Nutrition 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 229930182817 methionine Natural products 0.000 claims description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 3
- 230000007928 solubilization Effects 0.000 claims description 3
- 238000005063 solubilization Methods 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- 230000007774 longterm Effects 0.000 abstract 2
- 229940068065 phytosterols Drugs 0.000 description 19
- 239000000243 solution Substances 0.000 description 11
- 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 9
- 238000002441 X-ray diffraction Methods 0.000 description 7
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000006069 physical mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000008176 lyophilized powder Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- OILXMJHPFNGGTO-NRHJOKMGSA-N Brassicasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 OILXMJHPFNGGTO-NRHJOKMGSA-N 0.000 description 2
- OILXMJHPFNGGTO-ZRUUVFCLSA-N UNPD197407 Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)C=C[C@H](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZRUUVFCLSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 235000004420 brassicasterol Nutrition 0.000 description 2
- OILXMJHPFNGGTO-ZAUYPBDWSA-N brassicasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZAUYPBDWSA-N 0.000 description 2
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- 238000004128 high performance liquid chromatography Methods 0.000 description 2
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- 229960004452 methionine Drugs 0.000 description 2
- 238000000329 molecular dynamics simulation Methods 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
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- 208000024172 Cardiovascular disease Diseases 0.000 description 1
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- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
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- 239000002671 adjuvant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- 210000004027 cell Anatomy 0.000 description 1
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- 208000029078 coronary artery disease Diseases 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
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- 235000005686 eating Nutrition 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 235000006486 human diet Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
-
- A—HUMAN NECESSITIES
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0216—Solid or semisolid forms
- A61K8/022—Powders; Compacted Powders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/673—Vitamin B group
- A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
-
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Abstract
The invention provides an amorphous phytosterol with improved solubility and a preparation method thereof, the technical scheme takes the phytosterol as a main body, food-grade components are taken as ligands, the ligands and the proportion are screened by a rotary steaming method, the effects of different methods and different proportions of freeze drying and spray drying are compared, and finally, the co-amorphous phytosterol combination with high content and long-term stability in storage is obtained; the invention can effectively improve the solubility and the release degree of the phytosterol, has simple and safe process and stable long-term storage, and can be used in food or health care products and cosmetic systems.
Description
Technical Field
The invention relates to the field of foods, in particular to amorphous phytosterol with improved solubility and a preparation method thereof.
Background
Phytosterols naturally occur in plants and belong to one of the steroids, and are structurally similar to cholesterol in animals, with the difference that only methyl or ethyl groups are present at the C-24 position or additional double bonds are present at the C-22 position on the side chains. The usual phytosterols in the human diet are beta-sitosterol, brassicasterol, stigmasterol and brassicasterol, and eating foods rich in phytosterols has been shown to significantly reduce cholesterol levels in human blood, which inhibit cholesterol absorption and thereby reduce serum cholesterol levels. Intake of 2-3 g of phytosterol can reduce serum total cholesterol and low density lipoprotein by 10% and 15%, respectively, and finally reduce probability of suffering from cardiovascular disease and coronary artery disease. In addition, the phytosterol participates in regulating the fluidity and permeability of cell membranes, can stimulate immunity and protect skin, and has the physiological functions of resisting inflammation and cancer, effectively preventing colonitis, nonalcoholic fatty liver and the like. However, phytosterols cannot be synthesized by the human body and can only be ingested by daily diet. Although phytosterols are widely present in vegetable foods, significant health benefits are not obtained with amounts of phytosterols from daily diet of only 160-430 mg/day. Because the phytosterol is insoluble in water and oil, the phytosterol is easy to crystallize, has high melting point, high lipophilicity and low biological accessibility. Therefore, the application of phytosterol in foods, medicines and cosmetics is very limited.
The hydroxyl group at the C-3 position of the phytosterol and the long-chain polyunsaturated fatty acid are subjected to esterification reaction by a chemical modification method, and the synthesized phytosterol ester can improve the oil solubility of the phytosterol, for example, a phytosterol colloidal dispersion prepared by adding a nonionic surfactant into long-chain or medium-chain triacylglycerol by using a Soft Matter (2016) is studied, wherein the mass ratio of the phytosterol is 10%. However, esterified phytosterols can only be added to high-fat foods. In order to ingest sufficient phytosterols for cholesterol reduction purposes, consumers have to ingest large amounts of high-fat foods, which is detrimental to health. Meanwhile, the chemical modification method has the problems of environmental friendliness and low yield. The mixing of phytosterols with macromolecular substances by emulsification and encapsulation techniques is complicated to prepare and has the problem of low loading capacity, for example, LWT-Food Science and Technology (2020) has been studied to prepare phytosterol nanodispersions from zein and pectin with a loading capacity of only 13%. The mass percentage of the plant sterol prepared by using macromolecule protective colloid, plasticizer, surfactant and the like in the prior patent CN 1741748 is 0.1-80 percent. Meanwhile, some surfactants are used as crystallization inhibitors of phytosterols, and have certain limitations in the food field. Since free phytosterol molecules are usually present in crystalline form, they are difficult to enter into intestinal cells, resulting in extremely low bioavailability, and thus inhibition of crystallization of phytosterols is believed to be beneficial for their bioavailability and even health effects. The prior studies do not relate to ligand and method screening for solubilization of various small molecule food grade adjuvants of phytosterols, nor do the prior studies relate to solubilization effects of phytosterols and nicotinamide on phytosterols, as well as methods including rotary evaporation, lyophilization and spray drying, and comparison of different ratios.
Disclosure of Invention
In order to solve the problems of improving the solubility of the plant sterol and being applied to the preparation of health care products, the application provides the following technical scheme:
in a first aspect, the present invention provides an amorphous phytosterol composition having improved solubility, said composition being prepared by rotary evaporation of phytosterol and a ligand comprising one or both of the following: arginine, methionine, phenylalanine, isoleucine, sorbitol, erythritol, nicotinamide, lactitol, fructose, lactose, xylose, citric acid, malic acid, tartaric acid, ascorbic acid, nicotinamide; preferably, the ligand is one or more of arginine, isoleucine, lactitol, xylose, malic acid and nicotinamide, more preferably, the ligand is nicotinamide;
in another specific embodiment, the phytosterol comprises one or more of beta-sitosterol, stigmasterol, campesterol.
In a specific embodiment, the mass ratio of the plant sterol to the ligand is 1-100:1, preferably, the mass ratio of the plant sterol to the ligand is 10-30:1, and most preferably, the mass ratio of the plant sterol to the ligand is 20:1.
In a second aspect, the invention provides a process for the preparation of an amorphous phytosterol composition according to the first aspect of the invention comprising the steps of:
1) Preparing a solution of phytosterol in absolute ethyl alcohol, preparing a solution of ligand in water, mixing the solutions obtained by the preparation and the ligand, and slightly heating at 50-70 ℃ to obtain a clear solution obtained by the preparation;
2) Drying the clear solution obtained in step 1).
In a specific embodiment, wherein said drying is one of the following:
1) Performing rotary steaming at 70-80 ℃ and then performing vacuum drying at 55-65 ℃ for 8-16 hours;
2) Freeze-drying at-80+/-10 ℃ for 96-168 hours;
3) Spray drying;
the inlet temperature of spray drying is 160+/-5 ℃, the outlet temperature of spray drying is 90+/-5 ℃, the feeding rate is 20-25%, and the atomization air flow is 40-45 mm.
In a third aspect, the invention provides a freeze-dried or spray-dried powder of phytosterol-nicotinamide prepared by the method of the second aspect, which is characterized in that the phytosterol is in an amorphous state.
In a fourth aspect, the invention provides the use of nicotinamide for solubilisation of phytosterols; the preparation method is characterized in that nicotinamide is dissolved in water, phytosterol is dissolved in absolute ethyl alcohol, and the phytosterol and the nicotinamide are mixed according to the mass ratio of 1-100:1 and then dried.
In a specific embodiment, the drying is performed in one of the following ways:
1) Performing rotary steaming at 70-80 ℃ and then performing vacuum drying at 55-65 ℃ for 8-16 hours;
2) Freeze-drying at-80+/-10 ℃ for 96-168 hours;
3) Spray drying;
the inlet temperature of spray drying is 160+/-5 ℃, the outlet temperature of spray drying is 90+/-5 ℃, the feeding rate is 20-25%, and the atomization air flow is 40-45 mm. In a fifth aspect the present invention provides the use of an amorphous phytosterol composition according to the first aspect or a phytosterol-nicotinamide lyophilized powder according to the second aspect or the use according to the third aspect in the manufacture of a food, nutraceutical or cosmetic product.
The beneficial effects of the invention are as follows:
1) The solubility improvement condition of the phytosterol is measured according to different mass ratios and after rotary steaming with different ligands, and the fact that the solubility of the phytosterol is obviously improved when the ratio of the phytosterol to nicotinamide is 20:1 is known;
2) In the dry powder obtained by rotary steaming, freeze-drying or spray drying, the solubility of the phytosterol is improved obviously by the form of the freeze-dried powder;
3) XRD and in vitro release experiments show that the phytosterol in the composition obtained by the method is in an amorphous state, the release rate reaches 60%, and the interaction force between the phytosterol and the phytosterol is proved.
Drawings
FIG. 1 is a graph showing the effect of spin steaming of ligands of different masses on solubility improvement of phytosterols.
FIG. 2 is a screen of the effect of different proportions of phytosterol and nicotinamide on the improvement of solubility by spin steaming, freeze drying and spray drying.
FIG. 3 in vitro release profile of a plant sterol-nicotinamide 20:1 mass ratio composition freeze dried co-amorphous.
FIG. 4 accelerated storage XRD pattern for a plant sterol-nicotinamide 20:1 mass ratio composition freeze dried co-amorphous.
Figure 5 XRD pattern of the freeze-dried co-amorphous of the phytosterol-nicotinamide 20:1 mass ratio composition.
FIG. 6 DSC of a lyophilized co-amorphous of a plant sterol-nicotinamide 20:1 mass ratio composition.
FIG. 7 is a molecular dynamics simulation of a freeze-dried co-amorphous of a plant sterol-nicotinamide 20:1 mass ratio composition.
Detailed Description
The following detailed description of the embodiments and the technical solutions of the present invention will be made with reference to the accompanying drawings and specific examples, and should be clearly defined: those skilled in the art can, with the benefit of this disclosure, suitably modify the process parameters to achieve this. It is expressly noted that all such similar substitutions and modifications will be apparent to those skilled in the art, and are deemed to be included in the present invention. While the methods and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those skilled in the relevant art that variations and modifications can be made in the methods and applications described herein, and in the practice and application of the techniques of this invention, without departing from the spirit or scope of the invention.
The invention is further illustrated by the following examples, which are intended to illustrate the invention only and are not intended to limit the scope of the invention.
Example 1 screening for ligands that increase solubility of phytosterols
1. Screening for solubilizing ligands
a. Dispersing phytosterol in absolute ethyl alcohol, and completely dissolving by ultrasonic waves;
b. dissolving a small molecule ligand (arginine, methionine, phenylalanine, isoleucine, sorbitol, erythritol, nicotinamide, lactitol, fructose, lactose, xylose, citric acid, malic acid, tartaric acid, ascorbic acid and nicotinamide) in water according to an equal mass ratio;
c. mixing the two, slightly heating at 60deg.C to clarify the solution, and steaming at 75deg.C;
d. then placing the mixture at 60 ℃ for vacuum drying for 12+/-4 hours to obtain solid; wherein the same treatment group without ligand was used as a phytosterol control group.
e. Mixing the solid obtained in the step d with an equal volume of water to obtain a supersaturated solution, shaking in a water bath at 25 ℃ and 200rpm for 24 hours, and measuring the saturated solubility of the phytosterol by adopting HPLC. The HPLC conditions were: c8 column (4.6X250 mm,5 μm), mobile phase acetonitrile: water = 86%:14% by volume, a flow rate of 1mL/min, a column oven temperature of 35 ℃, a sample injection volume of 20. Mu.L, and a measurement wavelength of 208nm. The solubility of the phytosterol is expressed by the sum of the main components of the beta-sitosterol, campesterol and stigmasterol in the phytosterol.
Results As shown in FIG. 1, ligands that can increase the solubility of phytosterols include arginine, isoleucine, lactitol, xylose, malic acid, and nicotinamide; wherein the ratio of nicotinamide to phytosterol is highest, and the solubility of nicotinamide to phytosterol is improved by nearly 1 time compared with that of a control group, and can exceed 600 mug/mL.
Example 2 preparation of phytosterol-nicotinamide in different methods and at different ratios
Respectively dissolving plant sterol and nicotinamide in absolute ethanol and water according to the previous method, and respectively freeze-drying and spray-drying after mixing and clarifying. Wherein,
freeze drying at-80deg.C+ -10deg.C for 96-168 hr;
the spray drying inlet temperature is 160 ℃ +/-5 ℃, the outlet temperature is 90 ℃ +/-5 ℃, the feeding rate is 22%, and the atomizing air flow rate is 42mm.
Wherein the mass ratio of the phytosterol to the nicotinamide is 1:1, 20:1 and 100:1 respectively. The optimal freeze-dried powder mass ratio of the phytosterol to the nicotinamide is 20:1 (hereinafter called optimal freeze-dried powder).
As shown in fig. 2, the solubility of the freeze-dried powder is equivalent to that of the phytosterol-nicotinamide with the mass ratio of 1:1, and when the mass ratio of the phytosterol to the ligand nicotinamide is 20:1, the solubility is remarkably improved, and can be close to 1600 mug/mL at the highest; in contrast, in the spray drying method, the solubility is improved when the mass ratio of the phytosterol to the ligand nicotinamide is 20:1, which is equivalent to that of the mixture ratio of 1:1 after rotary evaporation, but the solubility improvement effect is not obvious when the weight ratio is other than that of the mixture ratio.
Example 3 in vitro Release test
10mg of the equivalent of phytosterol, the physical mixture and the amorphous group (the optimal freeze-dried powder described in example 2) were placed in 0.1% aqueous Tween 80 solution respectively, stirred at 37℃and 150rpm, 1mL of the solution was taken out every 0, 5min, 15min, 30min, 60min, 90min, 2h, 3h, 5h and 8h, 1mL of the solvent was supplemented, and the phytosterol content in the solution was determined.
As shown in FIG. 3, the optimal lyophilized powder of phytosterol released in vitro by about 60% compared to the phytosterol itself and the physical mixture.
Example 4 stability detection
Accelerated storage stability at 40 ℃ and 75% RH for 1 month simulates storage period change at room temperature and 60% RH for 4 months, and crystalline state change of optimal freeze-dried powder XRD of each 2d, 8d, 15d and 1M of sterols is measured, so that the stable and difficult crystallization of the crystalline state is found.
As shown in FIG. 4, the optimal freeze-dried powder obtained in example 2 of the present invention has good stability and no crystallization after 1 month of accelerated stability test.
EXAMPLE 5 characterization of phytosterol-nicotinamide
The best freeze-dried powder of phytosterol and nicotinamide is analyzed by X-ray diffraction (XRD) and Differential Scanning Calorimetry (DSC) and the physical mixture group of crystalline phytosterol and the crystalline phytosterol, wherein the physical mixture group is obtained by mixing and grinding equal amounts of the two powders. The phytosterol in the freeze-dried powder of the phytosterol-nicotinamide can be obtained by XRD and DSC, wherein the crystalline peak of the XRD disappears, and the melting point peak in the DSC disappears.
The best performing 20:1 lyophilized amorphous phytosterol powder (collectively referred to as the amorphous group in the graph) was analyzed for interaction forces by molecular dynamics simulation and found to have an interaction between the two.
The results are shown in figures 5-6, the best freeze-dried powder of phytosterol obtained by XRD and DSC is in an amorphous form, and the crystal lattice peaks corresponding to the phytosterol and nicotinamide disappear, and the melting point peaks of the phytosterol and nicotinamide in DSC disappear simultaneously, and the crystal lattice of the phytosterol and nicotinamide is changed correspondingly, so that a co-amorphous system is formed. The co-amorphous system lacks a periodic molecular arrangement crystalline structure, so that the lattice energy which must be overcome by the phytosterol in the dissolution process is avoided, and the solubility of the phytosterol is increased.
FIG. 7 analysis of site interactions with nicotinamide, wherein-N of nicotinamide, was found by plotting the distance between sites and the probability of force generation (g (r)) for the three main components of phytosterols, respectively 2 The distance of force between H and beta-sitosterol-OH is minimal and within 3.5 angstroms, which is the interaction of hydrogen bonding and Van der Waals forcesThe range of forces, which indicates the interaction forces between the nicotinamide and the phytosterol lyophilized powder, is probably responsible for the co-amorphous formation of both.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (10)
1. An amorphous phytosterol composition with improved solubility is characterized in that the composition is prepared by spin steaming phytosterol and a ligand, wherein the ligand is one or two of the following components: arginine, methionine, phenylalanine, isoleucine, sorbitol, erythritol, nicotinamide, lactitol, fructose, lactose, xylose, citric acid, malic acid, tartaric acid, ascorbic acid, nicotinamide.
2. The amorphous phytosterol composition of claim 1 wherein preferably said ligand is one or more of arginine, isoleucine, lactitol, xylose, malic acid, nicotinamide.
3. The amorphous phytosterol composition of claim 1 wherein said phytosterol comprises one or more of β -sitosterol, stigmasterol, campesterol.
4. The amorphous phytosterol composition of claim 1 wherein the mass ratio of phytosterol to ligand is from 1 to 100:1.
5. A process for preparing the amorphous phytosterol composition of any one of claims 1-4 comprising the steps of:
1) Preparing a solution of phytosterol in absolute ethyl alcohol, preparing a solution of ligand in water, mixing the solutions obtained by the preparation and the ligand, and slightly heating at 50-70 ℃ to obtain a clear solution obtained by the preparation;
2) Drying the clear solution obtained in step 1).
6. The method of claim 5, wherein the drying is one of:
1) Performing rotary steaming at 70-80 ℃ and then performing vacuum drying at 55-65 ℃ for 8-16 hours;
2) Freeze-drying at-80+/-10 ℃ for 96-168 hours;
3) Spray drying;
the inlet temperature of spray drying is 160+/-5 ℃, the outlet temperature of spray drying is 90+/-5 ℃, the feeding rate is 20-25%, and the atomization air flow is 40-45 mm.
7. The freeze-dried or spray-dried powder of phytosterol-nicotinamide obtained by the method according to claim 5 or 6, wherein the phytosterol is in an amorphous state.
8. The application of nicotinamide in solubilization of plant sterols is characterized in that nicotinamide is dissolved in water, plant sterols are dissolved in absolute ethyl alcohol, and the plant sterols and the nicotinamide are mixed according to the mass ratio of 1-100:1 and then dried.
9. The use according to claim 8, wherein said drying is one of the following:
1) Performing rotary steaming at 70-80 ℃ and then performing vacuum drying at 55-65 ℃ for 8-16 hours;
2) Freeze-drying at-80+/-10 ℃ for 96-168 hours;
3) Spray drying;
the inlet temperature of spray drying is 160+/-5 ℃, the outlet temperature of spray drying is 90+/-5 ℃, the feeding rate is 20-25%, and the atomization air flow is 40-45 mm.
10. Use of the amorphous phytosterol composition according to any one of claims 1 to 4 or the phytosterol-nicotinamide lyophilized or spray-dried powder according to claim 7 or the use according to claim 8 or 9 for the preparation of a food product, a health product or a cosmetic product.
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