JP2020515520A - 植物原材料から、スルホキシドなしで、有機硫黄化合物s−アルケニル−l−システインおよびs−アルキル−l−システインが富化された抽出物を調製するプロセス、およびそれらの炎症性疾患の処置における使用 - Google Patents
植物原材料から、スルホキシドなしで、有機硫黄化合物s−アルケニル−l−システインおよびs−アルキル−l−システインが富化された抽出物を調製するプロセス、およびそれらの炎症性疾患の処置における使用 Download PDFInfo
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
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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
- 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
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- A—HUMAN NECESSITIES
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- 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
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
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- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
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- C—CHEMISTRY; METALLURGY
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
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- A—HUMAN NECESSITIES
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- 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
Abstract
Description
最もよく知られている代用品はN−アセチルシステイン(NAC)である。NACの2つの主な用途は、粘液溶解薬(Cantu−Gonzalez 2014)として、およびアセトアミノフェン過剰服用(Heard 2008)の解毒剤としての使用である。化合物の主な既知の欠点は、悪心、嘔吐およびめまいを引き起こすため、長期間の採取ができない薬物であることであり、これはその使用を制限する(Sandilands 2009)。
LBPは、細胞の炎症の主なマーカーの1つである、血液中のLPS(細菌性脂質多糖体)の増加のマーカーである。この驚くべき事実は、NACの連続した使用において非常に重要な制限事項であるため、GSHおよび酸化防止剤の前駆物質としての解決策と見なされるべきではない。
前記方法は次の工程を含むという点で特徴づけられる:
i.出発植物材料における内因性酵素を不活性化する工程;
ii.植物バイオマスを均質化する工程;
iii.水性抽出物を分離する工程;
iv.水性抽出物をガンマ−脱グルタミル化する工程;
v.水性抽出物中のスルホキシドを除去する工程;
vi.精製する工程;
vii.濃縮する工程;
viii.乾燥する工程。
1つの実施形態において、本発明のプロセスの工程(ii)は水性媒体中で組織を砕くことにより行なわれる。
i.出発植物材料における内因性酵素を不活性化する工程;
ii.植物バイオマスを均質化する工程;
iii.水性抽出物を分離する工程;
iv.水性抽出物をガンマ−脱グルタミル化する工程;
v.水性抽出物中をスルホキシドの除去する工程;
vi.精製する工程;
vii.濃縮する工程;
viii.乾燥する工程。
この任意の工程の目的は、抽出物にまだ存在し得る固形微粒子を取り除くことである。この任意の工程は、フレームとプレートの型フィルター、葉状フィルターまたは水平板フィルター等の気圧調節されたプリコートフィルタ−の手段よって行なわれる。最終的な通路の直径は少なくとも1μmでなくてはならない。この工程で取り除かれた固形微粒子をフィルターと共に切り捨て、及び得られた濾液をプロセスの次の工程に曝す。
乾燥させることで、抽出物の貯蔵法は、それが粉末の特性を有するまで含水率を減少させることにより求められ、よってその耐用年数が延長される。この型のシステムの例は、限定されないが、凍結乾燥、真空乾燥、空気乾燥および噴霧化である。
反対に、SACの18mg/kgの使用は、NACの50mg/kgまたはSACが引き起こした可動性と同等の臨床評価の減少を引き起こした。これは、SACの18mg/kgの投与量が、NACの等価投与量よりも効果的だったことを示す。しかしながら、50mg/kgの投与量で、両方の処置間の違いが消滅したが、これは処置なしのEAEを有する動物のグループに対して同等に効果的だった。
Amagase H. Clarifying the real bioactive constituents of garlic. J Nutr. 2006; 136: 716S−725S.
Bae SE, Cho SY, Won YD, Lee SH, Park HJ. Changes in S−allyl cysteine contents and physicochemical properties of black garlic during heat treatment. LWT−Food Sci and Technol. 2014; 55: 397−402.
Borlinghaus J, Albrecht F, Gruhlke MCH, Nwachukwu ID, Slusarenko AJ. Allicin: Chemistry and Biological Properties. Molecules 2014; 19: 12591−12618.
Cantu−Gonzalez G. 50 years ago in The Journal of Pediatrics: The use of N−acetylcysteine in the treatment of cystic fibrosis. J Pediatr. 2014 Oct; 165(4):721.
Colin−Gonzalez AL, Ali SF, Tunez I, Santamaria A. On the antioxidant, neuroprotective and anti−inflammatory properties of S−allyl cysteine: An update. Neurochemistry International. 2015; 89: 83−91.
Drabowicz J, Numata T, Oae S. Dexygenation of sulfoxydes. A review. Organic Preparations and Procedures Int. 1977; 9(2): 63−83.
Francino MP. Antibiotics and the Human Gut Microbiome: Dysbioses and Accumulation of Resistances. Frontiers in Microbiology 2015; 6: 1543.
Heard KJ. Acetylcysteine for Acetaminophen Poisoning. The New England journal of medicine. 2008; 359(3):285−292.
Klavins JV. Pathology of Amino Acid Excess: II. Effects of Administration of Excessive Amounts of Sulphur Containing Amino Acids: L−Cystine. British journal of experimental pathology 1963; 44(5): 516.
Perez−Nievas BG, Garcia−Bueno B, Madrigal JL, Leza JC. Chronic immobilisation stress ameliorates clinical score and neuroinflammation in a MOG−induced EAE in Dark Agouti rats: mechanisms implicated. J Neuroinflammation 2010; 7, 60.
Petrovska BB, Cekovska S. Extracts from the history and medical properties of garlic. Pharmacognosy Reviews 2010; 4(7): 106−110.
Sandilands EA, Bateman DN. Adverse reactions associated with acetylcysteine. Clin Toxicol (Phila). 2009 Feb;47(2):81−8.
Yamazaki Y, Okuno T. Accumulation of S−allyl−cysteine in garlic bulbs by warming. Nippon Shokuhin Kagatu Kogatu Kaishi 2008; 55(9):410−415.
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US 5,093,122A. Method for preparing an S−allylcysteine−containing composition.
Claims (29)
- ネギ属の植物から式1の有機硫黄化合物の抽出物を得るためのプロセスであって、前記抽出物にはスルホキシドがないことが特徴とされ、
前記プロセスが:
i.出発植物材料における内因性酵素を不活性化する工程;
ii.植物バイオマスを均質化する工程;
iii.水性抽出物を分離する工程;
iv.水性抽出物をガンマ−脱グルタミル化する工程;
v.水性抽出物中のスルホキシドを除去する工程;
vi.精製する工程;
vii.濃縮する工程;
viii.乾燥する工程、
を含むことを特徴とする、プロセス。 - 工程(iv)の後に得られた抽出物は、更に、還元剤で還元工程に曝される、請求項1に記載のプロセス。
- 還元剤は亜硫酸水素ナトリウムおよびメタ重亜硫酸ナトリウムから選択される、請求項2に記載のプロセス。
- 還元は触媒の存在下で行われる、請求項2に記載のプロセス。
- 使用される触媒はヨウ素分子である、請求項4に記載のプロセス。
- 抽出物のろ過から成る工程(v)の後に、追加の工程を含む、請求項1から5のいずれか1つに記載のプロセス。
- 工程(vii)の後に、結晶化または沈殿化の追加の工程を含む、請求項1から6のいずれか1つに記載のプロセス。
- 得られた化学式1の化合物は、S−アリル−L−システイン(SAC)およびS−プロピル−L−システイン(SPC)およびS−メチル−L−システイン(SMC)から選択される、請求項1から7のいずれか1つに記載のプロセス。
- 出発植物材料はネギ属の植物の球根である、請求項1から8のいずれか1つに記載のプロセス。
- 工程(i)は、30分から2時間、60から110℃の間の温度で湿熱による出発植物材料の熱処理によって行なわれる、請求項1から9のいずれか1つに記載のプロセス。
- 工程(ii)は、水性の培地で組織を粉末にすることにより行われる、請求項1から10のいずれか1つに記載のプロセス。
- 工程(iii)は、ろ過、あるいは遠心分離によって行なわれる、請求項1から11のいずれか1つに記載のプロセス。
- 工程(iv)は、γ−グルタミルペプチダーゼ、γ−グルタミルペプチド転移酵素およびγ−グルタミルトランスフェラーゼ、を含む群から選択された酵素を用いて、工程(iii)で得られた抽出物をインキュベートすることにより実行される、請求項1から12のいずれか1つに記載のプロセス。
- スルホキシドを除去する工程はアリイナーゼを用いた酵素処置によって行なわれる、請求項1から13のいずれか1つに記載のプロセス。
- 工程(vi)における精製する工程はイオン交換クロマトグラフィーによって行われる、請求項1から14のいずれか1つに記載のプロセス。
- 工程(viii)における乾燥する工程は、凍結乾燥、真空乾燥、空気乾燥、あるいは噴霧化によって行われる、請求項1から15のいずれか1つに記載のプロセス。
- 得られた化合物は更に、チオスルフィン酸がない、請求項1から16のいずれか1つに記載のプロセス。
- 抽出物に存在するスルホキシドの量は、抽出物の中に存在するS−アルケニル−L−システインおよび/またはS−アルキル−L−システインの量に対して20質量%以下の割合である、請求項1から17のいずれか1つに記載のプロセス。
- 抽出物に存在するスルホキシドの量は、抽出物の中に存在するS−アルケニル−L−システインおよび/またはS−アルキル−L−システインの量に対して10質量%以下である、請求項1から18のいずれか1つに記載のプロセス。
- ヒトまたは動物における、慢性炎症を招く疾患の処置における使用のための化学式1の有機硫黄化合物を含む、医薬組成物または栄養補助組成物。
- 慢性炎症を招く前記疾患は多発性硬化症である、請求項20に記載の使用のための医薬組成物または栄養補助組成物。
- 化学式1の有機硫黄化合物はS−アルケニル−L−システインまたはS−アルキル−L−システインから選択される、請求項20または21のいずれか1つに記載の使用のための医薬組成物または栄養補助組成物。
- 化学式1の有機硫黄化合物は、S−アリル−L−システイン、S−メチル−L−システインおよび/またはS−プロピル−L−システインから選択される、請求項20から22のいずれか1つに記載の使用のための医薬組成物または栄養補助組成物。
- 化学式1の有機硫黄化合物はS−アリル−L−システイン(SAC)である、請求項23に記載の医薬組成物または栄養補助組成物。
- ヒトまたは動物における、慢性炎症を招く疾患の処置のための薬物の製造において化学式1の有機硫黄化合物を含む、医薬組成物または栄養補助組成物の使用。
- 慢性炎症を招く疾患は多発性硬化症である、請求項25に記載の医薬組成物または栄養補助組成物の使用。
- 化学式1の有機硫黄化合物はS−アルケニル−L−システインまたはS−アルキル−L−システインから選択される、請求項25または26のいずれか1つに記載の医薬組成物または栄養補助組成物の使用。
- 化学式1の有機硫黄化合物は、S−アリル−L−システイン、S−メチル−L−システインおよび/またはS−プロピル−L−システインから選択される、請求項25から27のいずれか1つに記載の医薬組成物または栄養補助組成物の使用。
- 化学式1の有機硫黄化合物はS−アリル−L−システイン(SAC)である、請求項28に記載の医薬組成物または栄養補助組成物の使用。
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ESP201730093 | 2017-01-26 | ||
ES201730093 | 2017-01-26 | ||
PCT/ES2018/070056 WO2018138400A2 (es) | 2017-01-26 | 2018-01-25 | Procedimiento para preparar extractos enriquecidos en compuestos organosulfurados s-alquenil-l-cisteína y s-alquil-l-cisteína, libres de sulfóxidos, a partir de materias primas vegetales y sus usos en el tratamiento de enfermedades inflamatorias |
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JP2019539829A Pending JP2020515520A (ja) | 2017-01-26 | 2018-01-25 | 植物原材料から、スルホキシドなしで、有機硫黄化合物s−アルケニル−l−システインおよびs−アルキル−l−システインが富化された抽出物を調製するプロセス、およびそれらの炎症性疾患の処置における使用 |
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US (1) | US20190380986A1 (ja) |
EP (1) | EP3587397B1 (ja) |
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CN115850130B (zh) * | 2022-11-29 | 2024-04-26 | 青岛博恩高科生物技术有限公司 | 一种高得率蒜氨酸的制备方法 |
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JP2875308B2 (ja) | 1989-11-22 | 1999-03-31 | 湧永製薬株式会社 | S−アリルシステイン高濃度含有組成物の製造方法 |
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JP2015144571A (ja) * | 2014-01-31 | 2015-08-13 | ユニチカ株式会社 | S−プロペニルシステインの製造方法 |
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- 2018-01-25 US US16/480,717 patent/US20190380986A1/en not_active Abandoned
- 2018-01-25 WO PCT/ES2018/070056 patent/WO2018138400A2/es active Search and Examination
- 2018-01-25 EP EP18745278.4A patent/EP3587397B1/en active Active
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WO2018138400A3 (es) | 2018-11-01 |
US20190380986A1 (en) | 2019-12-19 |
EP3587397A4 (en) | 2020-06-03 |
EP3587397B1 (en) | 2022-03-02 |
WO2018138400A2 (es) | 2018-08-02 |
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