NZ624662B2 - Genipin-rich material and its use - Google Patents
Genipin-rich material and its use Download PDFInfo
- Publication number
- NZ624662B2 NZ624662B2 NZ624662A NZ62466212A NZ624662B2 NZ 624662 B2 NZ624662 B2 NZ 624662B2 NZ 624662 A NZ624662 A NZ 624662A NZ 62466212 A NZ62466212 A NZ 62466212A NZ 624662 B2 NZ624662 B2 NZ 624662B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- genipin
- fruit
- mixtures
- rich
- extract
- Prior art date
Links
- AZKVWQKMDGGDSV-BCMRRPTOSA-N Genipin Chemical compound COC(=O)C1=CO[C@@H](O)[C@@H]2C(CO)=CC[C@H]12 AZKVWQKMDGGDSV-BCMRRPTOSA-N 0.000 title claims abstract description 129
- AZKVWQKMDGGDSV-UHFFFAOYSA-N genipin Natural products COC(=O)C1=COC(O)C2C(CO)=CCC12 AZKVWQKMDGGDSV-UHFFFAOYSA-N 0.000 title claims abstract description 122
- 239000000463 material Substances 0.000 title claims abstract description 31
- 239000000284 extract Substances 0.000 claims abstract description 73
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000605 extraction Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 15
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 claims abstract description 13
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 241000196324 Embryophyta Species 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002798 polar solvent Substances 0.000 claims abstract description 12
- 102000004190 Enzymes Human genes 0.000 claims abstract description 10
- 108090000790 Enzymes Proteins 0.000 claims abstract description 10
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims abstract description 9
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 6
- 238000010979 pH adjustment Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003086 colorant Substances 0.000 claims description 19
- 235000013305 food Nutrition 0.000 claims description 17
- 229940024606 amino acid Drugs 0.000 claims description 14
- 235000001014 amino acid Nutrition 0.000 claims description 14
- 150000001413 amino acids Chemical class 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 12
- -1 side Natural products 0.000 claims description 12
- 150000003141 primary amines Chemical group 0.000 claims description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 9
- 102000008186 Collagen Human genes 0.000 claims description 9
- 108010035532 Collagen Proteins 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 229960003767 alanine Drugs 0.000 claims description 9
- 229920001436 collagen Polymers 0.000 claims description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 235000004279 alanine Nutrition 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229920001661 Chitosan Polymers 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- 235000018102 proteins Nutrition 0.000 claims description 7
- 102000004169 proteins and genes Human genes 0.000 claims description 7
- 108090000623 proteins and genes Proteins 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 108010010803 Gelatin Proteins 0.000 claims description 6
- IBFYXTRXDNAPMM-BVTMAQQCSA-N Geniposide Chemical compound O([C@@H]1OC=C([C@@H]2[C@H]1C(=CC2)CO)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O IBFYXTRXDNAPMM-BVTMAQQCSA-N 0.000 claims description 6
- IBFYXTRXDNAPMM-FZEIBHLUSA-N Geniposide Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@H]2[C@@H]1CC=C2CO IBFYXTRXDNAPMM-FZEIBHLUSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- VGLLGNISLBPZNL-RBUKDIBWSA-N arborescoside Natural products O=C(OC)C=1[C@@H]2C([C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)OC=1)=C(CO)CC2 VGLLGNISLBPZNL-RBUKDIBWSA-N 0.000 claims description 6
- 229920000159 gelatin Polymers 0.000 claims description 6
- 239000008273 gelatin Substances 0.000 claims description 6
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- 235000011852 gelatine desserts Nutrition 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- ZJDOESGVOWAULF-OGJQONSISA-N Geniposidic acid Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2C(CO)=CC[C@@H]2C(C(O)=O)=CO1 ZJDOESGVOWAULF-OGJQONSISA-N 0.000 claims description 4
- VYAALAFRWREWLA-BVTMAQQCSA-N Geniposidic acid Natural products CCC1=CC[C@H]2[C@@H]1[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(=O)O VYAALAFRWREWLA-BVTMAQQCSA-N 0.000 claims description 4
- ZJDOESGVOWAULF-UHFFFAOYSA-N Geniposidinsaeure Natural products OC1C(O)C(O)C(CO)OC1OC1C2C(CO)=CCC2C(C(O)=O)=CO1 ZJDOESGVOWAULF-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004472 Lysine Substances 0.000 claims description 4
- BZPMXJKRKXDRID-UOIKKKDVSA-N Scandoside Natural products OC[C@H]1O[C@@H](O[C@H]2CC=C([C@@H]3[C@@H](O)C=C(CO)[C@H]23)C(=O)O)[C@H](O)[C@@H](O)[C@@H]1O BZPMXJKRKXDRID-UOIKKKDVSA-N 0.000 claims description 4
- 235000015203 fruit juice Nutrition 0.000 claims description 4
- 235000018977 lysine Nutrition 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 239000001062 red colorant Substances 0.000 claims description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 3
- 108010076119 Caseins Proteins 0.000 claims description 3
- 235000021559 Fruit Juice Concentrate Nutrition 0.000 claims description 3
- FYZYXYLPBWLLGI-AUOPOVQUSA-N Genipin 1-beta-gentiobioside Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@H]1OC=C([C@@H]2[C@H]1C(=CC2)CO)C(=O)OC)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FYZYXYLPBWLLGI-AUOPOVQUSA-N 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 108010073771 Soybean Proteins Proteins 0.000 claims description 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004473 Threonine Substances 0.000 claims description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 3
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 235000009697 arginine Nutrition 0.000 claims description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 3
- 239000005018 casein Substances 0.000 claims description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 3
- 235000021240 caseins Nutrition 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 229960002433 cysteine Drugs 0.000 claims description 3
- 235000013572 fruit purees Nutrition 0.000 claims description 3
- WSKNCDIGADDYAP-FLVHOVDBSA-N genipin 1-O-beta-D-isomaltoside Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H](O)[C@@H]2O)[C@@H]4C(=CC[C@]14C)CO WSKNCDIGADDYAP-FLVHOVDBSA-N 0.000 claims description 3
- 229960002442 glucosamine Drugs 0.000 claims description 3
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- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 3
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
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- 239000000376 reactant Substances 0.000 claims 3
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Classifications
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- 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
- A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
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- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/23—Removal of unwanted matter, e.g. deodorisation or detoxification by extraction with solvents
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- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/20—Ingredients acting on or related to the structure
-
- 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
- A23V2250/00—Food ingredients
- A23V2250/20—Natural extracts
- A23V2250/21—Plant extracts
Abstract
The disclosure relates to a method of preparing genipin-rich material from the fruit of Genipa Americana. The method comprises providing juice or extract from fruit of a plant of the Genipa americana, which contains sufficient genipin or derivatives of genipin capable of forming the aglycone, genipin; extracting the genipin/genipin derivatives from the fruit using a solvent selected from water, polar solvent, and mixtures thereof; adjusting the pH of the extraction to form the genipin aglycone, extracting the genipin aglycone from the mixture using a non-polar solvent; and processing the extract to form a material containing at least about 70% genipin using one or more steps selected from mixing, separating, heat treatment, pH adjustment, enzyme treatment and solvent removal. n; extracting the genipin/genipin derivatives from the fruit using a solvent selected from water, polar solvent, and mixtures thereof; adjusting the pH of the extraction to form the genipin aglycone, extracting the genipin aglycone from the mixture using a non-polar solvent; and processing the extract to form a material containing at least about 70% genipin using one or more steps selected from mixing, separating, heat treatment, pH adjustment, enzyme treatment and solvent removal.
Description
PCT/U52012/063836
GENIPIN-RICH MATERIAL AND ITS USE
Shaowen Wu
Gregory Horn
Technical Field
This application is based on and claims priority from US. Provisional Application
Serial No. 61/556,441, Wu and Horn, filed November 7, 201 1, orated herein by
reference.
This invention refers to novel off—white genipin-rich als and their use as
cross-linking reagents and for colorant development. More cally, the t
invention relates to a method for producing novel genipin—rich materials from the fruit of
Gem'pa Americana; the n—rich material contains genipin up to 97% w/w which
enables its use as agents for linking and as raw materials for colorant production.
Background
Today, synthetic als, such as colorants or cross—linking reagents, tend to
have decreasing acceptance in the food, ic, animal feed and textile industries. For
safety reasons, whether real or perceived, people tend to favor the use of natural or
organic ingredients in food, cosmetic, textile, and biomaterial products.
Genipin is a colorless compound. It belongs to the iridoid group. It is very active
chemically and reacts immediately when combined with compounds having primary
amine groups, such as amino acids, collagen, chitosan, glucosamine—type compounds and
various proteins and enzymes. When oxygen is present, the product may turn to blue,
green, or black quickly. Genipin is an iridoid ester, therefore, it can be hydrolyzed to
generate genipinic acid which also can react with different compounds to generate red
ZOlZ/063836
and brown colorants. The colorants ted from genipin are heat and pH stable. Since
genipin normally comes from plant als, its Kosher characteristics provide great
potential for use of n-derived colorants in bakery and canned food applications.
Large amount of iridoids, such as geniposide, oside, genipin—l-b-
gentiobioside, geniposidic acid and genipin, can be found in Gardeniajasminoides Ellis
fruit. Geniposide, an iridoid glycoside, is a main component comprising 7—8% of fruit
weight, while only trace amounts of genipin naturally exist in the Gardenia fruit.
Historically, the ds in Gardenia fruit were extracted from the fruit with methanol or
ethanol, and then separated as yellow t on active carbon, and treated with
s having lucosidic activity or proteolytic activity to convert glycoside
iridoids to aglycone form, genipin or genipinic acid. Then, genipin or nic acid can
be reacted with other compounds to produce colorants (KRl 020010096213A).
Genipin and other iridoid compounds, such as genipinie acid, genipin-
gentiobioside, geniposide and geniposidic acid, are found also in the fruits and leaves of
Gem'pa americana, also known as p, or Huito, a al wild plant. Genipin is
naturally present in the mature fruit, and its quantity is from 0 to 3.0% of fruit weight
depending on the degree ofripeness. Genipin is stable in the plant cell even though it is
not established where it is stored. Whenever the cell is broken, genipin will react
spontaneously with the amino acids that naturally exist in the fruit pulp and turn color to
blue or black in an air environment. In our previous patent application
(U820090246343Al), we made coloring (blue) fruit juice by mixing Genipa americana
fruit pulp withjuices from other fruits or vegetables. The natural acid-stable blue juice
has been used broadly in the food and beverage industries. Lopes et al. (US7927637B2)
used unprocessed raw juice obtained from Gem’pa americana fruit pulp, and mixed with
glycine or with glycine plus starch, to make blue colorants. Patrice Andre and co—worker
(U820100196298Al) used coloring materials obtained from the plant extraction of
Gem'pa americana, Gardeniajasminoides, Rothmannia, Adenorandia or Cremaspora,
bound to a solid substrate, to make cosmetic compositions.
1001048440
Genipin not only can generate colorants, but also can act as a good cross-linking agent.
ll et al. discovered a new biodegradable plastic polymer ing genipin as cross-
linking agent (EP2093256A2). Such plastics are useful in biological s for wound repair,
implants, stents, drug encapsulation and delivery, and other applications. Fujikawa et al. claimed
(US4983524) the use of iridoid aglycone, n, as a cross-linking agent to produce
lized enzyme on beads for food industry. Quijano, R and Tu, H (US 20080195230A1)
disclosed the use of genipin to fix whole, natural s to reduce antigenicity and
immunogenicity and prevent enzymatic ation of the tissue when implanted in a host.
However, pure genipin production historically involves many steps, including HPLC
separation, and currently its cost is high. No description in the art teaches the preparation of a
stable n—rich extract from Gem'pa americana plant, and its broad applications as natural
colorants and cross—linking agent in foods, drugs, nutritional supplements, personal care
products, cosmetics, animal feed, textiles, polymers, and in the biomaterial industries.
[0008a] Reference to any prior art in the specification is not, and should not be taken as, an
acknowledgment, or any form of suggestion, that this prior art forms part of the common general
knowledge in Australia or any other jurisdiction or that this prior art could reasonably be
ed to be ascertained, understood and regarded as nt by a person skilled in the art.
[0008b] As used herein, except where the context requires otherwise, the term ise” and
variations of the term, such as "comprising", "comprises" and "comprised”, are not intended to
exclude other additives, components, integers or steps.
Summafl
The present disclosure provides a method of producing stable genipin-rich extracts from
the Gem'pa americana plant. The process involves aqueous or polar solvent extraction and non—
polar organic solvent extraction; the powder formed is a genipin-rich extract with an ite
color and has genipin content up to about 97%.
The present disclosure r provides applications of the genipin—rich extracts in natural
colorant production and forming polymers for use in a broad range of areas, such as in
foodstuffs, drugs, nutritional supplements, personal care ts, cosmetics, animal
PCT/U52012/063836
feed, textiles, biodegradable polymers, and biomaterials production. es of such
uses are to be found in numerous patent documents, including U88283222,
99484, U820120189584, W02012048188, CN102399370, 821,
DE602007013718, USZOI 10082199, TW1334878, U820100183699, and such
documents are incorporated herein by reference.
[001 1] As used herein, all ratios and proportions noted are "by weight" unless otherwise
specified. In addition, all patents, patent applications and technical publications cited are
incorporated herein by reference.
Brief Description of the Drawing5
Fig. l is a flow chart representation of an embodiment of the process for making
genipin—rich extract produced from Gempa americana fruit.
ed Description
The present disclosure provides amethod of producing stable genipin-rich
extracts from the Genipa americana plant. The process involves aqueous or polar solvent
extraction and organic non-polar solvent tion. The resulting powder form of
genipin—rich extract is off-white in color and has genipin t up to about 97%. The
present disclosure further provides ations of the genipin—rich extracts in the
production of l heat—stable colorants and as a new cross—linking agent for use in a
broad range of areas, such as foodstuffs, drugs, nutritional supplements, personal care
products, cosmetics, animal feed, textiles, biodegradable polymers, and biomaterial
production.
PCT/U52012/063836
Starting als
The starting als used in this process are fruits or leaves from aplant of
Gem'pa amerz‘cana L. which is also known by numerous al names: genipap, huito,
jaguar, bilito, cafecillo denta, earuto, caruto rebalsero, confiture de singe, danipa, genipa,
genipa, genipayer bitu, guaitil, guaricha, guayatil Colorado, huitol, huitoc, huitu, irayol,
jagua blanca, jagua amarilla, jagua Colorado, jeipapeirc, juniper, maluco, mandipa,
marmelade—box, nandipa, nandipa genipapo, tapaculo, tapoeripa, taproepa totumillo,
other
yagua, yanupa-i, ycnipa—i, yenipapa bi, genipapo, , Vito, chipara, ay, or
varieties such asjenipaporana, orjenipapo-bravo, etc. The fruit is optimal for harvest
when mature in size, firm, and green to greenish brown in color.
als may be whole fruit, fruit pulp, fruit juice, fruit puree, fruitjuice
concentrate, dried powder from fruits orjuice, water—insoluble part of fruit, and leaves
from Gem'pa americana L,
Process for Genipin—Rich Extraction
In order to produce the genipin—rich extracts of the present invention, the mature
fruits of Genipa americana are processed with water or polar solvent in about 1:0.5—50
(by weight) ratios depending on extraction efficiency, preferably from about 5
ratios. After washing and/or blanching, the fruit is peeled and cut into ; then milled
or blended with water or polar solvents; extracted with or without heating, the pulp, seeds
and skin are separated by filtration; and liquid is collected. Extraction may take place for
up to about lhour, preferably about 15—30 min, at atemperature of about 15—40°C. The
water or polar t extraction from fruit pulp of Gem'pa americana may be repeated 1-
3 times. Then, the pH of polar solvent extracts is measured and adjusted to about 3.8-4.0
using acids. tration can be performed on a rotary evaporator with vacuum and
temperature set at about 40—46 C. The solid content in the concentrate may be greater
than 15% w/w, preferably about 40»70% w/w.
Next, the aqueous extract or the concentrated genipin-rich aqueous extract may be
further ted with lar organic solvents ing suitable mixing (by shaking
or agitation) in aratio of about 1:1. Those non—polar organic solvents have apolarity
index from about 0 to 5.0 and water solubility less than about 30%. The organic solvent
phase is then separated from aqueous phase by settling and ing the top organic
layer or by using a high speed fuge. Non—polar solvent extraction may be repeated
2—3 times ing on the extraction efficiency. The genipin—rieh extracts may
subsequently be dried by evaporation and organic solvent can be recycled and reused for
genipin extraction. The remaining yellow or off—white solid is a genipin—rich extract in
which genipin content is at least about 70% w/w ofthe solids.
Alternatively, the mature fruits of Genipa americana are processed with c
solvents directly in a ratio of about 121—2. After washing and/or ing, the fruit is
peeled and cut into pieces, then milled or blended, extracted with non—polar organic
solvent directly, with or without heating, the pulp, seeds and skin are separated and the
solvent extract is collected. Extraction may take place for up to about 1 hour, preferably
about 15—30 min at temperature of about 18—250C. The organic solvent extraction may be
repeated 2—3 times depending on the extraction efficiency. The genipin—rich extracts may
uently be dried using an evaporator and condenser, and organic solvent can be
recycled and reused. The resulting ite or yellow solids is genipin—rich extract that
contains genipin at greater than about 40% w/w of solid.
n-rich extracts may be aqueous or polar solvent extracts obtained from the
starting material sources described. Polar solvents include those with water solubility up
to 100%) and ty index greater than about 5.0, such as water, acetic acid, methanol,
ethanol, n-propanol, iso-propanol, dimethyl sulfoxide, dimethyl formamide, acetonitrile,
WO 70682 PCT/U82012/063836
acetone, dioxane tetrahydrofuran, etc., or acetic, , phosphate acid buffer solutions, or
mixtures thereof in ent ratios. This list is not intended to limit the solvent used,
however considering food safety, water, ethanol, n-propanol, iso—propanol, methanol and
acetic, citric and phosphate acid buffer solutions, are preferred for food uses of the
extract.
Genipin—rich extracts may alternatively be organic solvent extracts obtained from
aqueous or polar solvent extracts bed above. Non—polar organic solvents include
those with less than about 30" 0 of water solubility and a polarity index from 0 to about
.0, such as ethyl acetate, butyl acetate, n—butanol, diethyl ether, hexane, 2-butanonc,
form, l,2—dichloroethane, benzene, xylene, methyl—t—butyl ether, toluene, carbon
tetrachloride, trichlorocfhylene, cyclohexanc, pentane, and hcptane, or mixtures thereof in
different ratios. This list is not intended to limit solvent used, however considering food
safety, ethyl acetate, butyl acetate, and n-butanol are preferred.
Genipin-rich extracts may alternatively be organic t extracts ed from
the starting material sources described. Organic solvents include those with polarity
index less than about 6.0, and mixtures thereof in different ratios. The solvent or solvent
mixture with low solubility in water is preferred in order to ed colorless n—
rich extracts.
Methods used for liquid separation can be, for example, regular filtration,
centrifugation, press filtration, and membrane cartridge tion. The liquid—liquid
tion can be done, for example, by using high speed centrifuge, or by settling and
siphoning the required liquid layer.
Acids used for pH adjustment can be any organic or inorganic acids, selected to be
suitable for the intended end use.
PCT/U52012/063836
Concentration can be performed by any method laiown in the art, for example, by
evaporation using a rotary vacuum evaporator, a flash evaporator, an osmosis filtration
, or an ultra-filtration device with a suitable ne.
Properties of Genipin—Rich Extract
Genipin—rich t is an ite powder or ls. Some batches may have a
slightly yellowish or greenish tint if purity is relatively low. The genipin content can be
up to about 97% (w/w) depending on the extraction method. No geniposide, geniposidic
acid, or other iridoid compounds were found in genipin-rich extract when analyzed by
HPLC. The remainder of the composition of the genipin—rich extract is mainly moisture,
fat, and also small amounts of acids and nitrogen—containing compounds, with the
balance being carbohydrates, as noted in the following table.
Specification of Genipin Rich Material
Genipin 30—97%
Fatty Acids <1 0%
Fat <5 .0%
Protein <1 .0%
Organic Acids <0.5%
HPLC methods can be used to determine genipin content and perform other
iridoid analysis.
Genipin content of the off—white n—rich powder is stable when stored at
refrigerated temperatures. Genipin level decreased by less than about 5% after 3 months
PCT/U82012/063836
of storage. However, when mixing genipin-rich extract with compounds having a primary
amine group, genipin will quickly react and generate colorants and/or polymers.
High genipin content extract readily dissolves in alcohol, alcohol—water es,
or hot water. Its lity in cold water is limited.
Colorant Production
The present invention also provides a method of manufacturing a blue colorant by
using the genipin-rich t reaction and mixing with water and amino acids, for
example (but not limited to), lysine, histidine, argininc, ine, asparaginc,
nine, glycine, glutamic acids, tyrosine, valine, alanine, scrine, leucine, e,
carnitine, ornithinc and citrulline, in the presence of oxygen. Heating can be used to
rate the reaction speed. The molar ratios of n—rich extract to amino acids are
from about 120.5 to about 1:10. The blue shades generated are variable among deep blue,
violet-blue, bright—blue, and greenish-blue depending on the amino acid used. The blue
colorant ted from genipin—rich extract is a heat— and acid—stable pigment.
[003 1] Similar blue colorants also can be generated by reaction ofthe genipin—rich extract
with other extracts, fruit and vegetable juices, plant and animal materials, including dairy
and egg products, which contain amino acids, polypeptides, proteins, and compounds
with one or more primary amine groups. The blue color also can be generated by
reaction of the genipin—rich extract with collagen, gelatin, ehitosan, enzymes, and
microbes. The nt produced can be further concentrated or deposited on clay or
other carriers and used in foods, cosmetic (toothpaste, makeup, hair dye, etc), and textile
(clothes) applications.
PCT/U52012/063836
The present invention provides a method of manufacturing a red colorant by using
the genipin—rich extract. The genipin-rich extract is hydrolyzed to remove a methyl group
and convert the genipin to nic acid which further reacts with amine-containing
compounds, with extra organic acid present and under anaerobic conditions, to generate
red pigment. Heating can be used to accelerate red pigment formation. The red solution
can be further purified on an ion exchange column and the eluted material can be
concentrated on a rotary vacuum evaporator. The genipa red is a heat—stable pigment,
and is also stable at a high pH.
Genipin—rich extract can be dispersed or dissolved in about 5—50% ethanol,
ably about 5—15% ethanol, and about 0.5—1.5 N sodium hydroxide or potassium
ide on, to a concentration of extract of about 5—10 % w/w. Hydrolysis can be
performed with or without heating for from about 30 min to 24 hours, ably about 2—
hours under room temperature (~200C).
l-lydrolyzed genipin—rich extract can be neutralized in pH by using acids,
preferably organic acids, such as acetic acid, formic acid, lactic acid, citric acid, ic
acid, adipic acid, oxalic acid, succinic acid, fumarie acid, and malic acid, preferably
acetic acid and/or ic acid. The pH of hydrolyzed solution can be ed to the
about 3.5—5.0 range.
The acidified on is then heated to about 65—850C, and preferably about 70—
75°C, for about 5—120 minutes, preferably about 10—20 minutes. The insoluble brown by
products are d since they will not contribute to red color ion. Precipitate
separation can be accomplished by any of the filtration or centrifugation methods known
in the art, for example, using regular filtration, centrifuge, press filtration, or tangential
flow filtration or membrane cartridge filtration methods. Formation of the insoluble
brown by—products can be further enhanced by the addition of calcium carbonate to adjust
PCT/U82012/063836
the pH to about 5—7.5 and mixing for about 5-30 minutes. Precipitation separation can be
accomplished by the methods described above.
The clear on described above can be adjusted to pH about 4.0-4.6 with
organic acid or salt, ably acetic acid and/or sodium acetate. Red color is generated
after mixing with compounds having primary amine groups and heating to about 70—
95°C, ably about 80-850 C, for about 2 hours, or about 90—950C, for about 1 hour.
The nds with primary amine groups can be selected from amino acids, such as
alanine, arginine, lysine, aspartic acid, glutamie acid, e, histidine, valine, leucine,
and serine. This listing is not intended to limit useful compounds with primary amine
groups.
The present invention, in on, provides a method of manufacturing green
colorant by using the genipin—rieh extract. Genipin—rich extract can react with certain
amino acids, such as isoleucine, threonine, cysteine, and tryptophan, to generate green
color. It also can react with y amine—containing compounds and mix with
carotcnoids, o, and turmeric pigments to generate green color. Since genipa green
can provide a heat resistant green shade, it is very useful in the food industry because of
heat instability of the natural green pigment, chlorophyll.
[003 8] Similar green colorants also can be generated by reaction of the genipin—rich
extract with other extracts, fruit and vegetable juice, plant and animal materials, including
dairy and egg products, which are rich in amino acids, for example, isoleucine, threonine,
cysteine, and phan. The green color also can be generated by reaction of the
genipin-rich extract with collagen, gelatin, chitosan, enzymes and microbes and mixing
with carotenoids, annatto, and turmeric pigments to generate green color. The colorant
produced can be further trated or deposited on clay or other carriers and used in
foods, cosmetic (toothpaste, , hair dye, etc), and textile (clothes) applications,
PCT/U82012/063836
The present invention, in addition, provides a means to generate other colorants,
like purple, red, , , brown, and black by using the genipin—rich extract.
Purples and reds can be created by mixing genipin—rich extract with carrnine, beetjuice,
and anthcyanin colorants and solution with amine-containing compounds. Oranges and
yellows can be created by reacting genipin—rich extract with pentoses, such as xylose,
ribose, or n C. Black color shade can be generated when alkaline earth metals (cg.
magnesium or m), or metals with multi-valences are involved during n
reaction with compounds containing a y amine group.
Cross—linking Agent
The present invention provides new materials which contain up to about 97% of
genipin content. n—rich extract can react with any compound that contains a
primary amine group, such as collagen, gelatin, chitosan, glucosamine, and s
s and proteins, to form new texture materials used in, for example, the food,
cosmetic, biomaterial, and polymer industries.
The present invention also provides a cross-linking agent obtained from the
natural plant, Genipa americana, which can replace synthesized chemicals, such as
glutaraldehyde, dehyde, glyoxal, malonaldehyde, succinaldehyde, epoxy
compounds, etc. Genipin—rich extract used as a linking agent has a much lower
toxicity than those commonly used synthetic cross—linking reagents.
Genipin—rich extract can work as a natural cross—linking agent for encapsulation
production in the food and ceutical industries. Encapsulated materials can be
nutritional ingredients, such as omega—3 oil, Vitamin A, conjugated linolenic oil, or
medicines. Gelatin, collagen, whey proteins, casein, chitosan, soy proteins, and other
plant or animal proteins, are good starting materials in ction with the genipin—rich
extract to use to make an encapsulation shell, film or micro—membrane. The products
have good thermal and mechanical stability, as well as their biocompatible property.
PCT/U52012/063836
Following examples are provided for purpose of further illustrating the present
disclosure, but should in no sense be taken as limiting.
Example 1
A n—rich extract was generated based on the following process:
a) l‘luito fruits were peeled to yield 866.0 g of peeled fruit. The peeled fruit was cut
into pieces and blended with 1300 g of deionized (DI) water and pureed with a
blender to produce a puree;
b) the puree was allowed to stand for 15 min at room temperature; and the insoluble
solid was ted from the aqueous extract by filtration. Then, 1212.4 g of DI
water was added to the filtrate and mixed for 15 minutes followed by a second
filtration step;
the filtrate was adjusted to pH < 4.0 using citric acid, and concentrated to 25—55%
(w/w) of solid content on a rotovapor;
d) then, the trated aqueous extract was extracted using ethyl acetate in a 1:1
ratio. The colorless or slightly yellow clear ethyl acetate layer was collected.
This —liquid extraction was repeated 2 times;
next, the combined ethyl acetate t layers were evaporated on a rotovapor at
a temperature of 400 C and vacuum of 35 mm Hg to remove the solvent.
Condensed ethyl acetate can be reused for genipin extraction. After evaporating
the ethyl e, an off-white or slightly yellow powder was obtained. The
powder contained 74.4% w/w of genipin.
Example 2
A genipin-rich extract was generated based on ing process:
PCT/U82012/063836
a) Huito fruits, 462 g, were peeled and blended with DI water 537 g to e
puree;
b) the puree was allowed to stand for 15 min at room ature, and the insoluble
solid was separated from aqueous extract by filtration. Then, the same quantity of
DI water was added to the solid part, and the extraction step was ed 2 times;
c) the combined aqueous extract was adjusted to pH < 4.0 using citric acid and
concentrated to 24.92% (w/W) of solid content via a rotovapor;
(i) then, the concentrated aqueous extract was extracted using butyl acetate in lzl
ratio. The colorless or slightly yellow clear butyl acetate layer was collected.
This liquid—liquid extraction was repeated 2 times;
e) next, the combined butyl acetate extract was evaporated on a rotovapor at a
temperature of 55° C and vacuum of 35 mm Hg to remove the solvent.
Condensed butyl acetate can be reused for n extraction. After ating
butyl acetate, an off—white or slightly yellow powder was obtained. The powder
contains 90.9% w/w of genipin.
Example 3
The genipin—rich extract made by the method in e 2 was tested for
stability. Genipin—rieh powder, 0.20 g each, was sealed in Vials and stored at 4 OC.
Samples were pulled at O, 4 wks, 6 wks, and 12 wks, and genipin content was tested by
using the HPLC method. Results are shown in Table 1.
PCT/U82012/063836
Table 1. Stability of genipin-rich t
Storage Time (wks) Genipin, % w/w
12 t 84.7
The genipin al was stable over the period ofthe test,
Example 4
Fifteen grams of genipin-rieh extract made by the method in Example 1 was
dissolved in 118.10 g of 10% ethanol solution. 16.89 g of 0.9 N solution ofKOIrl was
added to the above mixture and the genipin was hydrolyzed with stirring at room
temperature (22° C) for 7.5 hours. The pH of the hydrolyzed solution was adjusted to
less than 4.0 with tartaric acid. The solution was heated to 74 0C for 15 min and cooled.
The precipitate was filtered out through #2 filter paper. Next, the pH of the filtrate was
adjusted to ~ 6.5 using calcium carbonate and the slurry was mixed for 10 minutes. The
resulting precipitate was filtered off and the filtrate pH was adjusted to 5 by the
on of acetic acid. After alanine (4.50 g) was added, genipin red color was
ped by heating to 82 0C for 2 hrs. The color was analyzed by taking 0.30 g of
genipin red color and diluting to 30.0 g with DI water. L—, a-, and b-values were
measured on a Hunter Lab ometer, and the absorption curve measured on a UV/VIS
spectrometer. Results are shown in the following table.
2012/063836
Parameters
Hunter e 27.86
Hunter a-value 10.21
Hunter b-value 2.26
Wavelength (max,nm) 550.09
Absorption (max) 0.67314
Example 5
Three grams of genipin—rich extract made by the method in Example 2 was
dissolved in 23.5g of 10% ethanol solution. 3.78g of LON solution ofKOH was added to
the above mixture and the genipin was hydrolyzed with stirring at room temperature
(220C) for 80 hours. The pH ofthe hydrolyzed solution was adjusted to less than 4.0
with tartaric acid. The solution was heated to 740C for 15 minutes and cooled. The
preeipate was removed by ion on #2 filter paper. Next, the pH of the filtrate was
ed to -7.0 using calcium carbonate and the slurry was mixed for 15 s. The
resulting precipate was filtered off and the filtrate pH was adjusted to 4.0—4.5 by the
addition of acetic acid. After e (1.20g) was added, genipin red color was developed
by heating to 84°C for 2 hours. The color was analyzed by taking 0.50g of genipin red
color and diluting to 30.0g with DI water. L—, a—, and b—values were measured on a
Hunter Lab spectrometer, and the absorption curve measured on a UV/VIS spectrometer.
Results are shown in the following table.
PCT/U82012/063836
Parameters
Hunter L—value
Hunter a—value
Hunter b—value 2.32
Wavelength (max, run) 549.97
Absorption (max) 0.94423
Example 6
One and a half grams of genipin-rich extract made by the method in Example 2
was dissolved in 118;; of 10% ethanol solution. 1.97g of l.ON solution of KOH was
added to the above mixture and the genipin was hydrolyzed wih stirring at room
temperature (22°C) for 8.0 hours. The pH of the hydrolyzed solution was adjusted to less
than 4.0 with tartaric acid. The solution was heated to 74°C for 15 minutes and cooled.
The itate was removed by ion through #2 filter paper. Next, the pH of the
filtrate was adjusted to —7.0 using m carbonate and the slurry was mixed for 15
minutes. The resulting precipitate was filtered off and the filtrate pH was adjusted to 4.0—
4.5 by the addition of acetic acid. After alanine (0.60g), taurine (0.60g), and magnesium
chloride (0.4486g) was added, a dark brown—black color was developed by heating to
84°C for 2 hours. The color was analyzed by taking 1.0g of n color and diluting to
.0g with DI water. L—, a—, and b-values were ed on a Hunter Lab spectrometer,
and the absorption curve measured on a UV/VIS spectrometer. Results are shown in the
following table.
PCT/U82012/063836
Parameters
Hunter L-Value
Hunter e 0.29
___,_________..____.____i
Hunter b—Value 0.85
Wavelength (max, nm) + 542.83
Absorption (max) 1 0.0170
Wavelength (2nd peak, nm) 1 595.06
Absorption (2nd peak) 0.88795
Example 7
0.1 08g of genipin—rich extract, made by the method in Example 2, was dispersed
in 8.6g of 800 ethanol aqueous solution in a test tube. Solids were completely ved
after heating in a~500C water bath. Then, 1.0m] aliquots of the above genipin solution
was put into test tubes separately and onine 0.012g, L—isoleueine 00145;, or L—
histidine 0.016g, respectively, were added. All test tubes were heated in an 80°C water
bath for 2 hours. The color was analyzed by taking 0.30g of genipin color produced and
diluting to 30.0g with DI water. L—, a-, and b—Values were measured on a Hunter Lab
spectrometer, and the absorption eurve measured on a UV/VIS ometer. Results are
shown in the following table.
L—Throenine eueine L-Histidine
Dilution (g/ml) 0.50/100 0.30/100 0.10/100
Color
Hunter L-value 79.12 87.41
Hunter a—value —5.91 3.42 —7.82
Hunter b—value -2.42 -0.77 -l7.46
Wavelenth (max, nin) 596.32 600.12 592.2
Absorption (max) 0.11914 0.06746 0.2537
Example 8
0.37g ofgenipin-rieh extract, made by the method in Example 2, was dispersed in
34.63g ol’ l0% ethanol aqueous solution in a beaker. Alanine 0.7g, and xylose, 1.4g,
were added and dissolved. Sample heated at 920C for lhour. After cooling, the color
was analyzed by taking 1.50g of the color solution and ng to 300;; with DI water.
The color was observed to be orange—red in contrast to the red color observed when
alanine was mixed alone with the genipin—rich extract. L, 3-, and es were
measured on a Hunter Lab spectrometer, and the results are shown in the following table.
Parameters L—Alanine and Xylose 1
Color -Red ’
Hunter e l 25.12
Hunter a-value
Hunter b—value
8440
Claims (22)
1. Method of preparing genipin—rich material from the fruit of Gem'pa americana or varieties f, comprising (a) providing juice or extract from fruit of a plant of the Gem'pa americana, which contains sufficient genipin or derivatives of genipin capable of forming the aglycone, genipin; (b) extracting the genipin/genipin derivatives from the fruit using a solvent selected from water, polar solvent, and mixtures thereof; (c) adjusting the pH of the step (b) tion to form the genipin aglycone; (d) extracting the genipin aglycone from the mixture of step (c) using a non—polar t; and (e) processing the extract of step (d) to form a al containing at least about 70% genipin using one or more steps selected from mixing, separating, heat treatment, pH adjustment, enzyme treatment and solvent l.
2. The method of claim 1 wherein the genipen/genipin derivative is selected from genipin, genipin—gentiobioside, side, geniposidic acid, oside, and mixtures thereof.
3. The method according to claim 1 or claim 2 wherein the non—polar solvent is selected from ethyl acetate, butyl acetate, n-butanol, diethyl ether, hexane, 2—butanone, chloroform, 1,2~ dichloroethane, benzene, xylene, methylet—butyl ether, toluene, carbon tetrachloride, trichloroethylene, exane, pentane, heptanes and mixtures thereof.
4. The method of any one of claims 1 t0 3 wherein the fruit of Gem'pa americana or varieties thereof is selected from whole fruit, fruit juice, fruit puree, fruit juice concentrate, dried powder forms of fruits or juice, insoluble parts of fruit, and mixtures thereof.
5. A method of preparing genipin-rich red colorant by preparing a genipin—rich material according to the following steps: (a) providing juice or extract from the fruit of Gem'pa americana or varieties thereof which ns sufficient genipin materials capable of forming the aglycone, genipin; 1001048440 (b) extracting the genipin materials from the fruit using a solvent selected from water, polar solvents, and mixtures thereof; (c) adjusting the pH of the step (b) extraction to form the genipin aglycone; (d) extracting the genipin aglycone from the mixture of step (c) using non-poplar solvent; and (e) processing the extract of step (d) to form a material containing at least about 7% genipin using one or more steps selected from mixing, separating, heat treatment, pH adjustment, enzyme treatment and solvent removal; and mixing said genipin—rich al with an amino acid in the presence of organic acid, and under anaerobic conditions.
6. The method of claim 5 wherein the genipin/genipin derivative is selected from n, genipin—gentiobioside, geniposide, geniposide acid, gardinoside, and mixtures thereof.
7. The method of claim 5 is selected or claim 6 wherein the organic non—polar solvent from ethyl e, butyl acetate, nol, diethyl ether, hexane, 2—butanone, chloroform, 1,2— dichloroethane, xylene, methyl—t—butyl ether, toluene, carbon tetrachloride, trichloroethylene, cyclohexane, pentane, heptane and mixtures thereof.
8. The method of any one of claims 5 to 7 wherein the fruit of Gem'pa americana or varieties thereof is selected from whole fruit, fruit juice, fruit puree, fruit juice concentrate, dried powder forms of fruits or juice, water—insoluble parts of fruit, and mixtures
9. The method of manufacturing a heat— and acid— stable colorant by mixing the genipin— from fruit and rich material made in any one of claims 5 to 8 with water and a reactant selected vegetable juices, plant and animal materials, ptides, proteins, compounds having one or in the presence of , the molar ratio of more primary amine groups, and mixtures thereof, genipin-rich extract to amino acid being from about 110.5 to about 1:10.
10. The method according to claim 9 wherein the reactant is an amino acid ed from lysine, ine, arginine, glutamine, asparagine, nine, glycine, ic acid, tyrosine, valine, alanine, serine, leueine, taurine, carnitine, ornithine, isoleucine, threonine, cysteine, tryptophan, citrulline, and mixtures thereof. 1001048440
11. The method according to claim 9 or claim 10 wherein the colorant is further purified and concentrated using an ion exchange column and/or a membrane filter.
12. The method of manufacturing red colorants by mixing the genipin-rich material made in any one of claims 1 to 4 with an amino acid, in the presence of extra c acid, and under anaerobic conditions.
13. The method according to claim 12 wherein the amino acid is selected from alanine, arginine, lysine, ic acid, and mixtures thereof.
14. The method according to any one of claims 9 to 11 wherein the reaction mixture additionally contains alkaline earth metals or metals with multi—valences, and a black color shade is made.
15. The method according to claim 14 n the additional reactant is selected from magnesium, calcium and mixtures thereof.
16. Colored foods and edible ts containing an effective amount of the colorant made according to any one ofclaims 9 to l l, 14 and 15.
17. Colored foods and edible products containing an effective amount of the red colorant made according to claim 12 or claim 13.
18. The method of g ed materials by reacting the genipin-rich extract made by any one of claims 1 to 4 with a compound containing a primary amine group ed from collagen, gelatin, chitosan, glucosamine, enzymes, proteins and mixtures thereof.
19. The method of forming textured materials by reacting the genipin—rich extract made by any one of claims 5 to 11 with a compound containing a primary amine group selected from collagen, n, an, glucosamine, enzymes, proteins, and mixtures thereof.
20. An edible encapsulated product wherein the encapsulating material is made by the reaction of the genipin—rich extract made by any one of claims 1 to 4 with a compound selected from n, collagen, whey protein, casein, chitosan, soy protein, and mixtures thereof, said ulating material encapsulating a food, nutritional or pharmaceutical material.
21. An edible encapsulated product wherein the encapsulating material is made by the reaction of the n-rich extract made by any one of claims 5 to 11 with a compound selected 2751 from gelatin, collagen, whey protein, casein, chitosan, soy protein and mixtures thereof, said encapsulating material encapsulating a food, nutritional or pharmaceutical material.
22. A method according to claim 1 or claim 5 substantially as hereinbefore described.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161556441P | 2011-11-07 | 2011-11-07 | |
US61/556,441 | 2011-11-07 | ||
PCT/US2012/063836 WO2013070682A1 (en) | 2011-11-07 | 2012-11-07 | Genipin-rich material and its use |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ624662A NZ624662A (en) | 2015-05-29 |
NZ624662B2 true NZ624662B2 (en) | 2015-09-01 |
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