JP2002345434A - トリテルペン類の濃縮物 - Google Patents
トリテルペン類の濃縮物Info
- Publication number
- JP2002345434A JP2002345434A JP2002106253A JP2002106253A JP2002345434A JP 2002345434 A JP2002345434 A JP 2002345434A JP 2002106253 A JP2002106253 A JP 2002106253A JP 2002106253 A JP2002106253 A JP 2002106253A JP 2002345434 A JP2002345434 A JP 2002345434A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- weight
- concentrate
- natural substance
- aqueous solution
- 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.)
- Pending
Links
- 150000003648 triterpenes Chemical class 0.000 title claims abstract description 9
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims abstract description 27
- 229940096998 ursolic acid Drugs 0.000 claims abstract description 27
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims abstract description 27
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 claims abstract description 25
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 claims abstract description 23
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 claims abstract description 23
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229940100243 oleanolic acid Drugs 0.000 claims abstract description 23
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 claims abstract description 23
- 235000013305 food Nutrition 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 13
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 6
- 235000000346 sugar Nutrition 0.000 claims abstract description 5
- 239000012141 concentrate Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 14
- 239000005445 natural material Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 238000003801 milling Methods 0.000 claims description 8
- 238000010298 pulverizing process Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 235000015872 dietary supplement Nutrition 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- MDZKJHQSJHYOHJ-LLICELPBSA-N maslinic acid Chemical compound C1[C@@H](O)[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MDZKJHQSJHYOHJ-LLICELPBSA-N 0.000 claims description 3
- 108010010803 Gelatin Proteins 0.000 claims description 2
- 229920000881 Modified starch Polymers 0.000 claims description 2
- ZZTYPLSBNNGEIS-OPAXANQDSA-N Pomolic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@](O)(C)[C@H]5C4=CC[C@@H]3[C@]21C ZZTYPLSBNNGEIS-OPAXANQDSA-N 0.000 claims description 2
- JYEJQUHSBMDABO-SYKQLJDKSA-N Pomolic acid Natural products C[C@@H]1CC[C@@]2(CC[C@H]3[C@@H]4CC[C@H]5C(C)(C)[C@@H](O)CC[C@]5(C)[C@H]4CC=C3[C@@H]2[C@]1(C)O)C(=O)O JYEJQUHSBMDABO-SYKQLJDKSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- MDZKJHQSJHYOHJ-UHFFFAOYSA-N crataegolic acid Natural products C1C(O)C(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MDZKJHQSJHYOHJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 239000000416 hydrocolloid Substances 0.000 claims description 2
- 235000015243 ice cream Nutrition 0.000 claims description 2
- 235000019426 modified starch Nutrition 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 239000004368 Modified starch Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 150000001720 carbohydrates Chemical group 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003925 fat Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 8
- 239000013049 sediment Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 238000002203 pretreatment Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000003811 acetone extraction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 1
- 241001479493 Sousa Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- -1 alkaline earth metal salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Botany (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Mycology (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Extraction Or Liquid Replacement (AREA)
- General Preparation And Processing Of Foods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01201296 | 2001-04-09 | ||
| EP01201296.9 | 2001-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002345434A true JP2002345434A (ja) | 2002-12-03 |
| JP2002345434A5 JP2002345434A5 (enExample) | 2005-09-15 |
Family
ID=8180120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002106253A Pending JP2002345434A (ja) | 2001-04-09 | 2002-04-09 | トリテルペン類の濃縮物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6824811B2 (enExample) |
| JP (1) | JP2002345434A (enExample) |
| CN (1) | CN100448887C (enExample) |
| AT (1) | ATE295087T1 (enExample) |
| DE (1) | DE60204078T2 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007514727A (ja) * | 2003-12-19 | 2007-06-07 | リピッド ニュートリション ベスローテン フェンノートシャップ | 過敏症および過反応症の治療用医薬の調製のためのオレアノール酸およびウルソル酸を含む組成物の使用 |
| EP1980569A1 (en) | 2007-04-04 | 2008-10-15 | Kenko Corporation | Process for preparing high purity corosolic acid and high purity ursolic acid |
| KR101393438B1 (ko) * | 2012-10-05 | 2014-05-12 | 경상북도(농업기술원) | 사과껍질로부터 우르솔릭산을 추출하는 방법 |
| JP2015189691A (ja) * | 2014-03-27 | 2015-11-02 | 公益財団法人東洋食品研究所 | Ｇｐｄｈ活性抑制剤 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100715309B1 (ko) | 2005-05-17 | 2007-05-04 | 한국콜마 주식회사 | 해리상수를 이용하여 용해된 우르솔산과 제미니형계면활성제를 함유하는 피부주름개선 화장료 및 이의제조방법 |
| US20100204121A1 (en) | 2009-02-10 | 2010-08-12 | Romero Augustin T | Dietary supplements containing terpenoid acids of maslinic acid or oleanolic acid and process for enhancing muscle mass in mammals |
| EP3681477A4 (en) | 2017-09-14 | 2021-06-09 | Phoenix Biotechnology, Inc. | PROCEDURES AND IMPROVED COMPOSITION FOR TREATMENT OF TREITERPEN RESPONSIBLE CONDITIONS, DISEASES, OR DISORDERS |
| CA3075729A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | Use of oleandrin to treatn viral infection |
| EP4009981B1 (en) | 2020-03-31 | 2023-08-16 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| RU2020130238A (ru) | 2020-03-31 | 2022-03-14 | Феникс Байотекнолоджи, Инк. | Способ и композиции для лечения коронавирусной инфекции |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152221B (de) | 1954-07-20 | 1963-08-01 | Elisabeth Ullsperger Geb Dotza | Verfahren zur Gewinnung von Triterpensaeuren |
| FR2541895B1 (fr) | 1983-03-04 | 1985-08-16 | Jean Daniel | Composition deodorante et antitranspirante a base d'acide triterpenique |
| CN1045585A (zh) * | 1990-04-03 | 1990-09-26 | 邵雅旭 | 一种从植物中提取齐墩果酸的方法 |
| JPH07583B2 (ja) | 1990-11-21 | 1995-01-11 | 北海道糖業株式会社 | 水溶性五環性トリテルペン包接化合物及びその製造方法並びにそれを利用した食品、飲料、口腔用組成物 |
| US20020019253A1 (en) * | 1997-05-05 | 2002-02-14 | Robert Reitzen | Computer gaming system |
| US5948460A (en) | 1998-07-27 | 1999-09-07 | Takasago International Corporation | Flavored product additive and method for using same |
| US6123968A (en) * | 1999-03-23 | 2000-09-26 | Mendez; Alejandro | Composition for extending shelf life for fresh fruits and vegetables without the use of refrigeration |
-
2002
- 2002-03-13 DE DE60204078T patent/DE60204078T2/de not_active Expired - Lifetime
- 2002-03-13 AT AT02075966T patent/ATE295087T1/de not_active IP Right Cessation
- 2002-04-09 JP JP2002106253A patent/JP2002345434A/ja active Pending
- 2002-04-09 US US10/118,319 patent/US6824811B2/en not_active Expired - Fee Related
- 2002-04-09 CN CNB021060282A patent/CN100448887C/zh not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007514727A (ja) * | 2003-12-19 | 2007-06-07 | リピッド ニュートリション ベスローテン フェンノートシャップ | 過敏症および過反応症の治療用医薬の調製のためのオレアノール酸およびウルソル酸を含む組成物の使用 |
| EP1980569A1 (en) | 2007-04-04 | 2008-10-15 | Kenko Corporation | Process for preparing high purity corosolic acid and high purity ursolic acid |
| US8101795B2 (en) | 2007-04-04 | 2012-01-24 | Kenko Corporation | Process for preparing high purity corosolic acid and high purity ursolic acid |
| KR101393438B1 (ko) * | 2012-10-05 | 2014-05-12 | 경상북도(농업기술원) | 사과껍질로부터 우르솔릭산을 추출하는 방법 |
| JP2015189691A (ja) * | 2014-03-27 | 2015-11-02 | 公益財団法人東洋食品研究所 | Ｇｐｄｈ活性抑制剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1380302A (zh) | 2002-11-20 |
| CN100448887C (zh) | 2009-01-07 |
| US20030049365A1 (en) | 2003-03-13 |
| US6824811B2 (en) | 2004-11-30 |
| ATE295087T1 (de) | 2005-05-15 |
| DE60204078T2 (de) | 2006-01-26 |
| DE60204078D1 (de) | 2005-06-16 |
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