JP5347018B2 - ピセアタンノール含有組成物及びピセアタンノール含有組成物の製造方法 - Google Patents
ピセアタンノール含有組成物及びピセアタンノール含有組成物の製造方法 Download PDFInfo
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- JP5347018B2 JP5347018B2 JP2011506939A JP2011506939A JP5347018B2 JP 5347018 B2 JP5347018 B2 JP 5347018B2 JP 2011506939 A JP2011506939 A JP 2011506939A JP 2011506939 A JP2011506939 A JP 2011506939A JP 5347018 B2 JP5347018 B2 JP 5347018B2
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- piceatannol
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- passion fruit
- extract
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- IIXHQGSINFQLRR-UHFFFAOYSA-N Piceatannol Natural products Oc1ccc(C=Cc2c(O)c(O)c3CCCCc3c2O)cc1O IIXHQGSINFQLRR-UHFFFAOYSA-N 0.000 title claims description 119
- CDRPUGZCRXZLFL-OWOJBTEDSA-N piceatannol Chemical compound OC1=CC(O)=CC(\C=C\C=2C=C(O)C(O)=CC=2)=C1 CDRPUGZCRXZLFL-OWOJBTEDSA-N 0.000 title claims description 119
- 239000000203 mixture Substances 0.000 title claims description 59
- 238000004519 manufacturing process Methods 0.000 title claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 72
- 239000002904 solvent Substances 0.000 claims description 72
- 244000288157 Passiflora edulis Species 0.000 claims description 57
- 235000000370 Passiflora edulis Nutrition 0.000 claims description 57
- 238000000605 extraction Methods 0.000 claims description 56
- 239000000284 extract Substances 0.000 claims description 51
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 150000002576 ketones Chemical class 0.000 claims description 17
- 235000013305 food Nutrition 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 6
- 238000010298 pulverizing process Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 239000005456 alcohol based solvent Substances 0.000 claims 1
- 239000005453 ketone based solvent Substances 0.000 claims 1
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 17
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 description 17
- 229940016667 resveratrol Drugs 0.000 description 17
- 235000021283 resveratrol Nutrition 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 229930014626 natural product Natural products 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 238000002211 ultraviolet spectrum Methods 0.000 description 7
- 235000013376 functional food Nutrition 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 5
- 235000013402 health food Nutrition 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000218996 Passiflora Species 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 235000015872 dietary supplement Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 240000001341 Reynoutria japonica Species 0.000 description 2
- 235000018167 Reynoutria japonica Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000002009 alkene group Chemical group 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- -1 polyphenol compounds Chemical class 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 239000001253 polyvinylpolypyrrolidone Substances 0.000 description 2
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 2
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 2
- 238000000825 ultraviolet detection Methods 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 240000006766 Cornus mas Species 0.000 description 1
- 235000003363 Cornus mas Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 235000016357 Mirtillo rosso Nutrition 0.000 description 1
- 244000077923 Vaccinium vitis idaea Species 0.000 description 1
- 235000017606 Vaccinium vitis idaea Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003061 melanogenesis Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Classifications
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/15—Preparation or pretreatment of starting material involving mechanical treatment, e.g. chopping up, cutting or grinding
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- 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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Mycology (AREA)
- Botany (AREA)
- Organic Chemistry (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Birds (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Emergency Medicine (AREA)
- Medical Informatics (AREA)
- Dermatology (AREA)
- Alternative & Traditional Medicine (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
[HPLC条件]
・ カラム:Mightysil RP-18 GP150-4.6 径4.6mm、長さ150mm(関東化学株式会社製)
・ カラム温度:40℃
・ 溶出条件:流速1ml/min、0%メタノール→30%メタノール(60min)
・ UV検出:280nm
したがって、本発明においては、上記に例示されるようなピセアタンノールの物性を指標にして、適宜分画、精製して、ピセアタンノールの含有量の高められた、パッションフルーツ種子由来のピセアタンノール含有組成物を調製することができる。
パッションフルーツを果皮・果肉・種子の3つの部位に分け、それぞれをフリーズドライして、粉砕機(商品名「サンプルミル 型式SK−M」、協立理工株式会社)で粉砕し、各部位を80%含水エタノールで抽出した。遠心後その上清をとりエバポレートで濃縮後、フリーズドライして粉末にした。この粉末を水に溶かして抽出物とした。そして、それぞれの固形分濃度を、種子抽出物については0.01g/mlに希釈し、果皮抽出物、又は果肉抽出物については0.1g/mlに希釈して、それらの5μlずつをHPLCにかけた。
・ カラム温度:40℃
・ 溶出条件:流速1ml/min、0%メタノール→30%メタノール(60min)
・ UV検出:280nm
図1A〜図1Cには、上記それぞれの抽出物のHPLCクロマトグラムを示す。その結果、図1Aに示されるように、種子抽出物については、41分付近にピークが見られた。これに比べて、果皮及び果肉からの抽出物については、インジェクションした固形分濃度が、種子抽出物の10倍であるにもかかわらず、41分付近のピークが確認できなかった。
パッションフルーツ種子からのピセアタンノールの抽出方法について検討した。具体的には、国内産と外国産の2種類のパッションフルーツの種子について、各種の溶媒を用いて、ピセアタンノールの抽出効率を調べた。
粉砕した種子の5gに80%含水エタノールの50mlを加え、30分間超音波をかけながら抽出を行った。その上清を回収した後、同じ操作で2回、計3回の抽出を行った。そして回収した抽出液を集め、得られた抽出液を80%含水エタノールで200mlに定容し、その10μlをHPLCにかけた。そして、常法に従い、HPLC分析のピーク下面積から、それを標準品濃度の検量線にあてはめることにより、その抽出物に含まれるピセアタンノールの量を定量した。なお、参考のために、レスベラトロールも同様に定量した。
上記80%含水エタノールによる抽出の後の抽出残渣に、70%含水アセトンの50mlを加え、30分間超音波をかけながら抽出を行った。その上清を回収した後、同じ操作で2回、計3回の抽出を行った。そして回収した抽出液を集め、得られた抽出液を70%含水アセトンで200mlに定容し、上記と同様にして、その抽出物に含まれるピセアタンノール、及びレスベラトロールの量を定量した。
溶媒を酢酸エチルに代えて、パッションフルーツ(上記外国産)の種子について、上記80%含水エタノールによる抽出と同様にして、フリーズドライした種子粉末5gから抽出されるピセアタンノール、及びレスベラトロールの量を定量した。
溶媒をジクロロメタンに代えて、パッションフルーツ(上記外国産)の種子について、上記80%含水エタノールによる抽出と同様にして、フリーズドライした種子粉末5gから抽出されるピセアタンノール、及びレスベラトロールの量を定量した。
パッションフルーツ種子からのピセアタンノールの抽出方法について更に検討した。具体的には、溶媒であるエタノールやアセトンの、その含水率が抽出効率に与える影響を調べた。
上記試験例2において溶媒を除去した後の抽出物(上記外国産由来)を秤量し、ピセアタンノール固形分含量を算出した。それらの値を表3に示す。
Claims (11)
- パッションフルーツ種子から得られ、パッションフルーツ種子の溶媒抽出物からなる、ピセアタンノールを0.0001〜99.9質量%の含有量で含むことを特徴とするピセアタンノール含有組成物。
- パッションフルーツ種子を粉砕した後、含水アルコール系溶媒及び含水ケトン系溶媒から選ばれた少なくとも1種を添加して攪拌し、前記溶媒中にピセアタンノールを抽出することを特徴とするピセアタンノール含有組成物の製造方法。
- パッションフルーツ種子を粉砕した後、含水アルコール系溶媒及び含水ケトン系溶媒のいずれか一方を添加して攪拌し、該溶媒中にピセアタンノールを抽出して第1抽出物を得、更に、前記抽出物として回収されなかった残渣に、含水アルコール系溶媒及び含水ケトン系溶媒のうち上記で選択しなかった他方を添加して攪拌し、該溶媒中にピセアタンノールを抽出して第2抽出物を得、前記第1抽出物と第2抽出物とを混合する、請求項2のピセアタンノール含有組成物の製造方法。
- 前記パッションフルーツ種子は、パッションフルーツの生の種子又はパッションフルーツの生の種子を乾燥した種子である請求項2又は3記載のピセアタンノール含有組成物の製造方法。
- 前記含水アルコール系溶媒が含水エタノールであり、又は前記含水ケトン系溶媒が含水アセトンである請求項2〜4のいずれか1つにピセアタンノール含有組成物の製造方法。
- 前記含水エタノールは、エタノールを20〜99.9体積%含むものである請求項5記載のピセアタンノール含有組成物の製造方法。
- 前記含水アセトンは、アセトンを20〜99.9体積%含むものである請求項5記載のピセアタンノール含有組成物の製造方法。
- 前記各溶媒中における攪拌を、超音波振動又は振とうによって行う請求項2〜7のいずれか1つに記載のピセアタンノール含有組成物の製造方法。
- 抽出後、溶媒を減圧留去する請求項2〜8のいずれか1つに記載のピセアタンノール含有組成物の製造方法。
- パッションフルーツ種子から得られ、パッションフルーツ種子の溶媒抽出物からなる、ピセアタンノールを0.0001〜99.9質量%の含有量で含むピセアタンノール含有組成物を添加したことを特徴とする飲食品。
- パッションフルーツ種子から得られ、パッションフルーツ種子の溶媒抽出物からなる、ピセアタンノールを0.0001〜99.9質量%の含有量で含むピセアタンノール含有組成物を添加したことを特徴とする化粧品。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014062111A (ja) * | 2007-10-04 | 2014-04-10 | Morinaga & Co Ltd | ピセアタンノール含有組成物 |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5415037B2 (ja) * | 2007-10-04 | 2014-02-12 | 森永製菓株式会社 | コラーゲン産生促進剤 |
JP2010030911A (ja) * | 2008-07-25 | 2010-02-12 | Morinaga & Co Ltd | コラーゲン産生促進剤 |
JP5637707B2 (ja) * | 2010-03-18 | 2014-12-10 | 森永製菓株式会社 | スキルプシンb含有組成物及びスキルプシンb含有組成物の製造方法 |
AU2011366060B2 (en) * | 2011-04-22 | 2015-01-15 | Morinaga & Co., Ltd. | Composition containing scirpusin B, and process for producing composition containing scirpusin B |
TWI480060B (zh) * | 2011-04-27 | 2015-04-11 | Morinaga & Co | 含有三棱素b之組成物及含有三棱素b之組成物之製造方法 |
US20130266676A1 (en) * | 2012-04-10 | 2013-10-10 | Natreon, Inc. | Terminalia chebula compositions and method of extracting same |
CN103505467B (zh) * | 2012-06-15 | 2016-02-24 | 昆明制药集团股份有限公司 | 一种茋类化合物在制备预防和治疗抑郁症药物中的用途 |
FR2999429B1 (fr) | 2012-12-18 | 2015-01-02 | Expanscience Lab | Extrait de graines de passiflore et compositions cosmetiques, pharmaceutiques, dermatologiques ou nutraceutiques le comprenant |
JP5285194B1 (ja) * | 2013-04-22 | 2013-09-11 | 森永製菓株式会社 | 飲食品 |
JP6077384B2 (ja) * | 2013-05-14 | 2017-02-08 | 森永製菓株式会社 | 植物抽出物の含水溶液に含まれるピセアタンノールの安定化方法、及び、植物抽出物の含水溶液 |
JP6118196B2 (ja) * | 2013-06-27 | 2017-04-19 | 森永製菓株式会社 | スチルベン単量体を含む溶液の製造方法 |
JP2015130819A (ja) | 2014-01-10 | 2015-07-23 | 森永製菓株式会社 | ヒドロキシスチルベン製造方法 |
JP6435158B2 (ja) * | 2014-10-17 | 2018-12-05 | 森永製菓株式会社 | 精製スチルベン化合物の製造方法 |
CN105078934A (zh) * | 2015-08-31 | 2015-11-25 | 昆药集团股份有限公司 | 白皮杉醇的新用途 |
FR3045380B1 (fr) | 2015-12-21 | 2019-08-23 | Laboratoires Expanscience | Extrait de graines de passiflore et compositions cosmetiques, pharmaceutiques ou dermatologiques le comprenant. |
KR101836171B1 (ko) | 2016-10-06 | 2018-03-08 | 이정복 | 패션푸르츠 분열조직세포 추출물을 함유하는 줄기세포 성장용 배지 조성물 및 피부 미백용 조성물 |
WO2021146651A1 (en) * | 2020-01-17 | 2021-07-22 | Muhammed Majeed | Process and compositions for enhancing energy expenditure |
CN111763141A (zh) * | 2020-07-07 | 2020-10-13 | 昆明翔昊科技有限公司 | 大黄类药材中白皮杉醇的提取方法、微胶囊分子包埋方法及其在食品和保健品中的应用 |
CN111704530A (zh) * | 2020-07-07 | 2020-09-25 | 昆明翔昊科技有限公司 | 大黄类药材中白皮杉醇的提取方法、微胶囊分子包埋方法及其在化妆品中的应用 |
CN112957344B (zh) * | 2021-02-25 | 2022-08-26 | 广西大学 | 一种含西番莲黄酮纳米制剂及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005075766A (ja) * | 2003-08-29 | 2005-03-24 | National Institute Of Advanced Industrial & Technology | エンドセリン−1産生抑制剤 |
CN1710043A (zh) * | 2005-06-17 | 2005-12-21 | 长沙桑霖生物科技有限公司 | 一种从西番莲种籽中提取西番莲籽油的方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4238509A1 (de) * | 1992-03-11 | 1994-05-19 | Ahmad Khalil | Haarwuchssystem und Haarwasser gegen Haarausfall |
CN1149939C (zh) * | 2000-06-14 | 2004-05-19 | 华南农业大学 | 甜橙西番莲混合果汁饮料生产方法 |
AU2003903909A0 (en) | 2003-07-25 | 2003-08-07 | Albright & Wilson (Australia) Limited | Production methods |
WO2005023740A2 (en) | 2003-09-05 | 2005-03-17 | Dsm Ip Assets B.V. | Process for the preparation of stilbene derivatives |
US20060134244A1 (en) | 2004-12-21 | 2006-06-22 | Takemoto Arnold C | Breast health supplement and detoxification preparations |
JP4620960B2 (ja) | 2004-03-29 | 2011-01-26 | 株式会社ナリス化粧品 | イタドリ根抽出物の精製法及びその精製物を含有する化粧料 |
JP2007531734A (ja) | 2004-04-02 | 2007-11-08 | インダストリアル・リサーチ・リミテッド | パッションフルーツの抽出物及びその使用 |
US20060280821A1 (en) | 2005-04-04 | 2006-12-14 | Foo Lai Y | Method of treating inflammation disorders using extracts of passion fruit |
CN1309323C (zh) * | 2005-07-14 | 2007-04-11 | 江城绿色版纳生态食品有限公司 | 以西番莲为原料制作果汁粉的工艺 |
US20080118449A1 (en) | 2006-11-21 | 2008-05-22 | Alvin Ronlan | Cosmetic formulations of piceatannol and retinoids and methods of use thereof |
WO2008086400A2 (en) | 2007-01-09 | 2008-07-17 | Isp Investments Inc. | Sirtuin-activating compounds of enhanced bioavailability |
CN100560579C (zh) | 2007-07-04 | 2009-11-18 | 北京绿色金可生物技术股份有限公司 | 红豆越橘提取物及其制备方法和应用 |
CN101710043B (zh) * | 2009-12-09 | 2011-05-18 | 胡小弟 | 沥青混合料抗裂性能试验仪 |
-
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005075766A (ja) * | 2003-08-29 | 2005-03-24 | National Institute Of Advanced Industrial & Technology | エンドセリン−1産生抑制剤 |
CN1710043A (zh) * | 2005-06-17 | 2005-12-21 | 长沙桑霖生物科技有限公司 | 一种从西番莲种籽中提取西番莲籽油的方法 |
Non-Patent Citations (2)
Title |
---|
JPN6013029287; JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY Vol.52, 2004, 4713-9 * |
JPN6013029288; DATABASE FSTA [Online] INTERNATIONAL FOOD INFORMATION SERVICE (IFIS), FRANkFURT-MAIN, DE; BAVARESCO * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014062111A (ja) * | 2007-10-04 | 2014-04-10 | Morinaga & Co Ltd | ピセアタンノール含有組成物 |
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