KR20020011856A - Cyclooxygenase Inhibitor, and Food and Beverage containg the Same - Google Patents
Cyclooxygenase Inhibitor, and Food and Beverage containg the Same Download PDFInfo
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- KR20020011856A KR20020011856A KR1020010014857A KR20010014857A KR20020011856A KR 20020011856 A KR20020011856 A KR 20020011856A KR 1020010014857 A KR1020010014857 A KR 1020010014857A KR 20010014857 A KR20010014857 A KR 20010014857A KR 20020011856 A KR20020011856 A KR 20020011856A
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- mangosteen
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- 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)
- A61K36/38—Clusiaceae, Hypericaceae or Guttiferae (Hypericum or Mangosteen family), e.g. common St. Johnswort
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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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
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- 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
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- 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
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
Abstract
Description
본 발명은 망고스틴 유래의 시클로옥시게나아제 저해제 및 그를 함유하는 시클로옥시게나아제 저해작용을 갖는 음식품에 관한 것이다.The present invention relates to a cyclooxygenase inhibitor derived from mangosteen and a food and drink having a cyclooxygenase inhibitor containing the same.
아스피린, 인도메타신으로 대표되는 대부분의 시클로옥시게나아제 저해제는 프로스타글란딘 류의 생합성을 억제하는 작용을 갖기 때문에, 프로스타글란딘이 관여하는 질병에 유효하지만, 현재 사용되고 있는 시클로옥시게나아제 저해제의 대부분은, 소화성궤양, 현기증 등의 부작용이 있고, 또 치료에 필요한 사용량과 부작용이 발현하는 사용량과의 사이에 큰 차이가 없기 때문에, 보다 안전성이 높은 시클로옥시게나아제 저해제의 개발이 요망되고 있다.Most of the cyclooxygenase inhibitors represented by aspirin and indomethacin have an effect of inhibiting prostaglandin biosynthesis, so most of the cyclooxygenase inhibitors currently used are digestible. Since there are side effects such as ulcers and dizziness, and there is no significant difference between the amount used for treatment and the amount of side effects expressed, there is a demand for the development of a higher safety cyclooxygenase inhibitor.
또, 종래의 시클로옥시게나아제 저해제는, 그것을 음식품에 첨가하면 정미(呈味), 풍미에 영향을 미쳐서 상품가치를 현저히 떨어뜨릴 염려가 있다.Moreover, when the cyclooxygenase inhibitor of the related art is added to food and drink, there is a fear that the value of the commodity may be remarkably reduced by affecting taste and flavor.
한편, 망고스틴(Garcinia mangostana L)의 과실은, 일반적인 이용법으로써 과육은 식용으로써 이용되고 있고, 과피에 대해서는 원산지인 태국에서 민간약으로써 설사를 그치게 하거나 창상(創傷) 치료에 이용되고 있다.On the other hand, the fruit of mangosteen (Garcinia mangostana L) is used as a general method of edible flesh, and the skin is used as a folk medicine in Thailand of origin, to stop diarrhea or to treat wounds.
망고스틴(Garcinia mangostana L.)의 과피의 기타 이용법으로써는, 일본국 특개평 6-98738호 공보 및 특개평 7-147951호 공보에 식품용보존재, 특개평 5-17365호 공보에 5α-리덕타아제 저해제, 특개평 7-250658호 공보에 항균제, 특개평 8-208501호 공보에는 항헬리코박터 피로리약, 특개평 9-87155호 공보에는 자외선흡수제, 특개평 10-120586호 공보에는 세린프로테아제 저해제가 기재되어 있다.As another method of using the skin of mangosteen (Garcinia mangostana L.), a preservative for food in Japanese Patent Application Laid-Open Nos. 6-98738 and 7-147951, and 5α-reducta in Publication No. 5-17365 An agonist inhibitor, an antimicrobial agent in Japanese Patent Laid-Open No. 7-250658, an anti-helicobacter pylori drug in Japanese Patent Laid-Open No. 8-208501, an ultraviolet absorber in Japanese Patent Laid-Open No. 9-87155, and a serine protease inhibitor in Japanese Patent Laid-Open No. 10-120586 It is.
또, 망고스틴(Garcinia mangostana L.) 과피의 수용성 추출물에 대해서는, 일본국 특개평 4-244004호 공보에 비만세포로부터의 히스타민 유리억제작용에 따른 미백·항염증작용, 망고스틴(Garcinia mangostana L.) 과피의 극성용매추출물 및 α-망고스틴, γ-망고스틴에 대해서는, 일본국 특개평 10-72357호 공보에 히스타민 및 세로토닌에 대한 길항작용에 따른 항알레르기 작용이 기재되어 있다.Moreover, about the water-soluble extract of the mangosteen (Garcinia mangostana L.) rind, Japanese Patent Application Laid-Open No. 4-244004 discloses a whitening, anti-inflammatory action, and mangosteen (Garcinia mangostana L.) according to histamine release from mast cells. For the polar solvent extract of the skin, α-mangosteen and γ-mangosteen, Japanese Patent Application Laid-Open No. 10-72357 discloses antiallergic action according to antagonism of histamine and serotonin.
그러나, 종래기술에는, 망고스틴(Garcinia mangostana L.)의 시클로옥시게나아제 저해작용에 관한 것은 없다.However, in the prior art, there is nothing related to the cyclooxygenase inhibitory effect of the mangosteen (Garcinia mangostana L.).
본 발명의 목적은, 부작용이 없어 안전하고, 정미성(呈味性), 안정성이 우수하며, 시클로옥시게나아제 저해작용이 강한 시클로옥시게나아제 저해제를 제공하는 것 및 그것을 유효성분으로 함유한 정미(呈味)에 우수한 시클로옥시게나아제 저해용 음식품을 제공하는데 있다.SUMMARY OF THE INVENTION An object of the present invention is to provide a cyclooxygenase inhibitor which is safe without side effects, has excellent taste and stability, and has a strong cyclooxygenase inhibitory action, and a net rice containing the same as an active ingredient. It is to provide the food-drinks for cyclooxygenase inhibition excellent in (iii).
본 발명자등은, 상기 과제를 해결하기위해 예의 연구를 수행하여, 망고스틴(Garcinia mangostana L.)의 과피로부터 각종용매로 추출하고, 또한 그의추출물에 함유된 수종의 성분을 단리(單離)하고, 그것의 추출물 및 성분에 대해서 시클로옥시게나아제 저해제로써의 효과를 확인한 결과, 망고스틴의 과피로부터 함수유기용제 또는 유기용제로 추출하여 얻어진 추출물 및 하기 화학식 1로 표현되는 α-망고스틴 및 하기 화학식 2로 표현되는 γ-망고스틴에서 우수한 시클로옥시게나아제 저해작용을 갖는 것을 발견하고, 본 발명을 완성하였다.MEANS TO SOLVE THE PROBLEM This inventor performed earnest research in order to solve the said subject, extracts it with the various solvents from the peel of mangosteen (Garcinia mangostana L.), and isolates the several components contained in the extract. , As a result of confirming the effect as a cyclooxygenase inhibitor on its extracts and components, the extract obtained by extracting with a water-containing organic or organic solvent from the skin of mangosteen and α- mangosteen represented by the formula It was found that γ-mangosteen represented by 2 had excellent cyclooxygenase inhibitory activity, and completed the present invention.
즉 본 발명은, 망고스틴의 과피로부터 함수유기용제 또는 유기용제로 추출하여 얻어진 추출물 및 α-망고스틴 및 γ-망고스틴을 유효성분으로 하는 시클로옥시게나아제 저해제이다.That is, this invention is the extract obtained by extracting with the organic organic solvent or the organic solvent from the skin of mangosteen, and the cyclooxygenase inhibitor which uses alpha-mangosteen and gamma-mangosteen as an active ingredient.
또, 본 발명은, 상기 시클로옥시게나아제 저해제를 함유하는 정미, 풍미에 우수한 시클로옥시게나아제 저해용 음식품이다.Moreover, this invention is the food-drinks for cyclooxygenase inhibition excellent in the taste and flavor containing the said cyclooxygenase inhibitor.
본 발명의 유효성분인 망고스틴의 과피로부터 함수유기용제 또는 유기용제로 추출하여 얻어진 추출물은, 물레나무과 식물의 망고스틴(Garcinia mangostana L.)의 과실(날 것 또는 건조된 것)로부터 얻어진 과피를 사용한다. 망고스틴의 과피는 그대로 사용하여도 좋지만, 건조하고 분쇄하여 분말로 사용하는 것이 추출효율이 좋아져 바람직하다. 또, 망고스틴의 과피를 함수유기용제 또는 유기용제로 추출하기전에, n-헥산, 석유에테르 등의 비극성 용제로 탈지하여도 좋다.The extract obtained by extracting the organic or organic solvent from the skin of mangosteen, the active ingredient of the present invention, is obtained from the fruits (raw or dried) of mangosteen (Garcinia mangostana L.) of the Asteraceae. use. The skin of mangosteen may be used as it is, but it is preferable to dry, pulverize and use it as a powder, since extraction efficiency improves. The skin of mangosteen may be degreased with a nonpolar solvent such as n-hexane or petroleum ether before extracting the peel of mangosteen with a water-containing organic solvent or an organic solvent.
추출용매로서는, 메탄올, 에탄올, n-프로판올, 이소프로판올, n-부탄올, 아세톤, 초산에틸, 디에틸에테르, 클로로포름, 글리세린, 에틸글리콜, 프로필글리콜 등의 유기용제, 바람직하게는 극성용제, 특히 에탄올은 알콜류, 또는 유기용제에 물을 혼합한 것을 사용한다. 물과의 혼합비율은, 특히 제한은 없지만, 물의 비율로 바람직한 것은 70% v/v 이하, 좀더 바람직하게는 60% v/v 이하이다. 추출온도에 대해서는, 추출효율을 고려하면 실온으로부터 용매의 환류온도가 바람직하다. 추출시간은 추출용매의 종류, 과피의 분쇄상태 및 추출온도에 따라 변화하지만, 0.5시간 ∼ 24시간이 바람직하다.As the extraction solvent, organic solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, acetone, ethyl acetate, diethyl ether, chloroform, glycerin, ethyl glycol and propyl glycol, preferably polar solvents, in particular ethanol Alcohol or an organic solvent mixed with water is used. The mixing ratio with water is not particularly limited, but the ratio of water is preferably 70% v / v or less, more preferably 60% v / v or less. Regarding the extraction temperature, considering the extraction efficiency, the reflux temperature of the solvent from room temperature is preferable. The extraction time varies depending on the type of extraction solvent, the pulverized state of the skin and the extraction temperature, but 0.5 hours to 24 hours are preferable.
상기추출용매에서 추출하여 얻은 추출물은, 필요에 따라 증발기 등으로 추출용매를 농축하거나, 또는 제거하여도 좋다.The extract obtained by extraction from the extraction solvent may be concentrated or removed by using an evaporator or the like as necessary.
본 발명의 유효성분인 α-망고스틴 및 γ-망고스틴은, 망고스틴(Garcinia mangostana L.)의 과실 등으로부터 공지의 방법으로 추출·정제하여 제조하는 것이 가능하지만, 합성한 것을 사용하는 것도 가능하다.Although α-mangosteen and γ-mangosteen, which are the active ingredients of the present invention, can be extracted and purified from a fruit of mangosteen (Garcinia mangostana L.) by a known method, a synthesized one can also be used. Do.
이와 같이 하여 얻은 본 발명의 시클로옥시게나아제 저해제는, 프로스타글란딘이 병원성물질로써 관여하고 있는 질병의 치료, 예방에 유효하고, 예를 들면, 통증, 발열, 염증, 인플루엔자 또는 기타 바이러스 감염에 관련된 증상, 세균감염에 따른 감기, 인두염, 인두의 통증, 기관지염, 편도염, 치주염, 치조골염, 치통, 치육염, 통풍, 관절염, 신장염, 간염, 기관지염, 월경곤란증, 두통, 궤양성 대장염, 염좌(捻挫) 및 좌상, 근육통, 신경통, 골막염, 화상, 및 외과적 및 치과적 처치후의 염증의 치료, 예방에 사용될 수 있다.The cyclooxygenase inhibitor of the present invention thus obtained is effective for the treatment and prevention of diseases in which prostaglandins are involved as pathogenic agents, for example, symptoms related to pain, fever, inflammation, influenza or other viral infections, Cold, pharyngitis, pharyngeal pain, bronchitis, tonsillitis, periodontitis, alveolaritis, toothache, gingivitis, gout, arthritis, nephritis, hepatitis, bronchitis, dysmenorrhea, headache, ulcerative colitis, sprain and sprain due to bacterial infection It can be used for the treatment, prevention of myalgia, neuralgia, periostitis, burns, and inflammation after surgical and dental treatment.
또, 본발명의 시클로옥시게나아제 저해제는, 시클로옥시게나아제가 관여하는 종양세포의 증식·전이를 저해하는 것이 가능하고, 대장암 등의 암치료나 암예방에 이용하는 것도 가능하다.Moreover, the cyclooxygenase inhibitor of this invention can inhibit the proliferation and metastasis of the tumor cell which cyclooxygenase participates, and can also be used for cancer treatment and cancer prevention, such as colorectal cancer.
또한, 본 발명의 시클로옥시게나아제 저해제는, 수축성 프로스타글란딘의 합성을 방해함으로써 프로스타글란딘유발 평활근수축을 저해하는 능력에 의해, 월경곤란증, 조기분만, 뼈의 결손의 치료(변형성 관절증의 치료), 빈뇨, 절박성요실금치료, 심근경색, 뇌일혈의 예방·치료에 사용하는 것이 가능하다.In addition, the cyclooxygenase inhibitor of the present invention, by the ability to inhibit prostaglandin-induced smooth muscle contraction by interfering with the synthesis of contractile prostaglandins, treatment of dysmenorrhea, premature delivery, bone defects (treatment of deformed arthrosis), frequent urination, It can be used for urinary incontinence therapy, myocardial infarction and prevention and treatment of cerebral hemorrhage.
또한, 본 발명의 시클로옥시게나아제 저해제는, 수면유발성 프로스타글란딘의 합성을 방해하는 것으로써 프로스타글란딘에 의한 수면을 억제하는 작용에 의해, 수면방지에도 유효하다.Moreover, the cyclooxygenase inhibitor of this invention is effective also in sleep prevention by the effect which inhibits sleep by prostaglandin by interfering with the synthesis | combination of a sleep-induced prostaglandin.
본 발명의 시클로옥시게나아제 저해제는, 망고스틴(Garcinia mangostana L.)의 과피의 함수유기용제 또는 유기용제추출물 및 α-망고스틴 및 γ-망고스틴을, 단독으로 또는 다른 의약 혹은 임의 제제용 담체, 희석제 등과 혼합하거나, 임의 제형으로 하여 의약으로써 이용할 수 있다. 예를 들면, 제형으로써 정제, 과립제,세립제, 경캅셀제, 연캅셀제, 경구용액체제제, 주사제 등을 예시하는 것이 가능하다.Cyclooxygenase inhibitors of the present invention, the aqueous organic solvent or organic solvent extract of the skin of the mangosteen (Garcinia mangostana L.) and α- mangosteen and γ- mangosteen, alone or in the form of other pharmaceutical or carrier It can be mixed with a diluent, etc., or can be used as a medicine in arbitrary formulations. For example, it is possible to exemplify tablets, granules, fine granules, hard capsules, soft capsules, oral solution preparations, injections and the like as the formulation.
또, 본발명의 시클로옥시게나아제 저해용 음식품은, 본 발명의 시클로옥시게나아제 저해제인 망고스틴 추출물 및 α-망고스틴 및 γ-망고스틴의 1종이상을 각종의 식품에 배합하여 제조하는 것이 가능하다. 예를 들면, 시클로옥시게나아제 저해용 음식품으로써는, 청량음료, 과자, 냉과, 유제품, 주류, 육류 등을 들수 있다.Moreover, the food-drinks for cyclooxygenase inhibition of this invention mix and manufacture the mangosteen extract which is a cyclooxygenase inhibitor of this invention, and at least 1 sort (s) of (alpha) -mangosteen and (gamma) -mangosteen to various foods, and to manufacture. It is possible. For example, as a food and drink for cyclooxygenase inhibition, a soft drink, a confectionery, a frozen dessert, dairy products, alcoholic beverages, meat, etc. are mentioned.
본 발명의 시클로옥시게나아제 저해제의 유효성분인 망고스틴 추출물 및 α-망고스틴 및 γ-망고스틴의 유효량에 대해서는, 투여방법 및 필요한 치료에 따라 변화하여, 한가지로 규정하기는 곤란하지만, 망고스틴 추출물은 동물체중 1㎏ 당 건조중량으로 0.5㎎ ∼ 500㎎, 성인(70㎏)에 대하여는 1일당의 바람직한 전투여량이 5㎎∼5g, 좀더 바람직하게는 5㎎ ∼ 1g이고, α-망고스틴 및 γ-망고스틴에 대해서는 동물체중 1㎏당 0.1㎎ ∼ 100㎎, 성인(70㎏)에 대하여는 1일당의 바람직한 전투여량이 1㎎ ∼ 1000㎎, 좀더 바람직하게는 5㎎ ∼ 500㎎이다.The effective amount of mangosteen extract and α-mangosteen and γ-mangosteen, which are the active ingredients of the cyclooxygenase inhibitor of the present invention, vary depending on the administration method and the necessary treatment, and it is difficult to define one mangosteen. The extract has a dry weight of 0.5 mg to 500 mg per kilogram of animal body weight, and the preferred fighting amount per day for adults (70 kg) is 5 mg to 5 g, more preferably 5 mg to 1 g, α-mangosteen and For gamma-mangosteen, the preferred combat amount per day is 0.1 mg to 100 mg per adult body weight, and for adults (70 kg), 1 mg to 1000 mg, more preferably 5 mg to 500 mg.
본 발명의 시클로옥시게나아제 저해용 음식품에 있어서 유효성분으로써의 망고스틴 추출물 및 α-망고스틴 및 γ-망고스틴의 함유량으로써는, 음식품으로써의 1일의 통상 섭취량으로 상기의 유효량을 만족시키도록 함유량을 규정하는 것이 가능하다.The content of mangosteen extract as an active ingredient and α-mangosteen and γ-mangosteen as an active ingredient in the cyclooxygenase inhibitory food or drink of the present invention satisfies the above-mentioned effective amount in a daily intake as a food or drink. It is possible to define content so that it may be made.
이하에서 실시예를 들어 본 발명을 좀더 상세하게 설명하지만, 본 발명의 범위는 이하의 실시예에 한정되는 것이 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited to the following Examples.
실시예Example
우선 망고스틴(Garcinia mangostana L.)의 과피로부터 시클로옥시게나아제 저해작용을 갖는 추출물 및 α-망고스틴 및 γ-망고스틴을 조제하는 실시예를 보이고, 다음에는 그것의 프로스타글란딘 생합성 저해작용, 시클로옥시게나아제 저해작용을 확인하는 시험 방법 및 결과에 대하여 보이고, 또 본 발명의 시클로옥시게나아제 저해제 및 시클로옥시게나아제 저해용 음식품의 예를 보인다.First, an example of preparing an extract having a cyclooxygenase inhibitory activity and α-mangosteen and γ-mangosteen from the skin of mangosteen (Garcinia mangostana L.), and then inhibiting its prostaglandin biosynthesis, cycloox The test method and results confirming the inhibitory action of the cagenase are shown, and examples of the cyclooxygenase inhibitor and the cyclooxygenase inhibitory food and drink for the present invention are shown.
실시예 1망고스틴 메탄올 추출물 Example 1 Mangosteen Methanol Extract
망고스틴(Garcinia mangostana L.)의 미건조 과피 1㎏을 10ℓ의 메탄올에 담그고, 24시간 실온하에서 추출했다. 여과후, 여과액을 증발기에서 감압건조하여 80g의 본 발명의 시클로옥시게나아제 저해제를 얻었다.1 kg of undried peel of mangosteen (Garcinia mangostana L.) was immersed in 10 L of methanol, and extracted at room temperature for 24 hours. After filtration, the filtrate was dried under reduced pressure in an evaporator to obtain 80 g of the cyclooxygenase inhibitor of the present invention.
실시예 2망고스틴 40% 에탄올 수용액 추출물 Example 2 Mangosteen 40% Ethanol Extract
망고스틴(Garcinia mangostana L.)의 건조과피분말 500g 을 5ℓ의 40% 에탄올에 담그고, 24시간 실온하에서 추출하였다. 여과후, 여과액을 증발기로 감압건조시켜 104g 의 본발명의 시클로옥시게나아제 저해제를 얻었다.500 g of dried and peeled powder of mangosteen (Garcinia mangostana L.) was immersed in 5 L of 40% ethanol and extracted at room temperature for 24 hours. After filtration, the filtrate was dried under reduced pressure with an evaporator to obtain 104 g of a cyclooxygenase inhibitor of the present invention.
실시예 3망고스틴 70% 에탄올 수용액 추출물 Example 3 Mangosteen 70% Ethanol Aqueous Extract
망고스틴(Garcinia mangostana L.)의 건조과피분말 480g 을 5ℓ의 70%에탄올로 4시간(60℃) 교반추출하였다. 여과후, 여과액을 증발기로 감압건조시켜 128g 의 본 발명의 시클로옥시게나아제 저해제를 얻었다.480 g of dried and skin powder of Mangosteen (Garcinia mangostana L.) were extracted with 5 L of 70% ethanol for 4 hours (60 ° C). After filtration, the filtrate was dried under reduced pressure with an evaporator to yield 128 g of the cyclooxygenase inhibitor of the present invention.
실시예 4망고스틴 에탄올 추출물 Example 4 Mangosteen Ethanol Extract
망고스틴(Garcinia mangostana L.)의 건조과피분말 1.1㎏ 을 11ℓ의 에탄올로 4시간(60℃) 교반추출하였다. 여과후, 여과액을 증발기로 감압건조시켜 128g 의본 발명의 시클로옥시게나아제 저해제를 얻었다.1.1 kg of dried and peeled powder of mangosteen (Garcinia mangostana L.) were extracted with 11 L of ethanol for 4 hours (60 ° C). After filtration, the filtrate was dried under reduced pressure with an evaporator to obtain 128 g of the cyclooxygenase inhibitor of the present invention.
실시예 5α-망고스틴 및 γ-망고스틴의 조제 Example 5 Preparation of α-mangosteen and γ-mangosteen
실시예 1의 추출물 80g 을 350㎖의 초산에틸에 용해 후, 200㎖ 의 물로 2번 세정했다. 남아있는 초산에틸 분량을 증발기로 용매를 증류제거시켜 20g 의 건조물을 얻었다. 이 건조물을 실리카겔컬럼크로마토그래피로 정제하였다. 용출은 헥산-초산에틸계로 점차, 극성을 주는 그레디언트 용출을 행하고, 3개의 분획을 얻었다. 최초에 얻은 분획(5g)을 다시 한번, 실리카겔컬럼크로마토그래피(헥산-초산에틸, 10:90 →30:70 →50:50)로 정제하여, 황색결정상의 α-망고스틴 2g 을 얻었다. 2번째의 분획(2g)을 다시 한번 실리카겔컬럼크로마토그래피(헥산-초산에틸 30:70 → 50:50, 초산에틸만, 최후에 초산에틸메탄올, 50:50)로 정제하여, 황색비결정상의 γ-망고스틴 500㎎을 얻었다.80 g of the extract of Example 1 was dissolved in 350 ml of ethyl acetate, and then washed twice with 200 ml of water. The remaining amount of ethyl acetate was distilled off the solvent by an evaporator to obtain 20 g of dried product. This dried product was purified by silica gel column chromatography. The elution was gradually eluted with a hexane-ethyl acetate system to give three fractions. The first obtained fraction (5 g) was once again purified by silica gel column chromatography (hexane-ethyl acetate, 10:90-> 30: 70-> 50: 50) to give 2 g of? -Mangosteen as yellow crystals. The second fraction (2 g) was once again purified by silica gel column chromatography (hexane-ethyl acetate 30:70 to 50:50, ethyl acetate only, finally ethyl acetate, 50:50) to give a yellow amorphous γ. -500 mg of mangosteen was obtained.
시험예 1프로스타글란딘 생합성 저해시험 Test Example 1 Prostaglandin Biosynthesis Inhibition Test
6구멍 플레이트에 15% 말혈청 및 2.5% 소태아 혈청을 포함한 F-10 Nutrient Mixure(Ham) 배지와 C 6 래트 글리오마 세포를 1.0 ×105cells/㎖ 로 되도록 가하였다. 37℃, 5% CO2인규베이터 안에서 3일간 배양하였다. 그후, 피험물질을 가하여 37℃에서 10분간 배양하고, 또한 100μM 의 Ca 이온화 A 23187을 100μM 가하여 10분간 배양하였다. 미리 얼음으로 냉각시켜 놓은 반응정지액(100μM 인도메타신 50mM EDTA)을 가하여, 배양상청을 회수하였다. 배양상청에 1N 염산을 가해서 pH 4로하고, 초산에틸을 가하여 분배하고, 생성한 프로스타글란딘 E2를 초산에틸층에 이행시켰다. 초산에틸층을 회수하고, 감압건고 되게 한 후, 0.5㎖의 10mM Tris-염산완충액(pH 7.6)에 용해시켰다. 이 용액에 [3H] 프로스타글란딘 E2용액과 프로스타글란딘 E2항체를 가하여, 4℃로 24시간 반응시켰다. 그 후, 챠콜 액을 가하여 원심분리하고, 상청의 방사활성을 액체 신틸레이션 카운터로 계측하고, 배지중에 유리된 프로스타글란딘 E2량을 정량하였다. 피험물질을 함유하지 않은 컨트롤의 프로스타글란딘 E2생성량에 대한 피험물질에 따른 프로스타글란딘 E₂생성량의 저하를 프로스타글란딘 E2생성저해율로 표시하였다. 그의 결과를 표1에 나타낸다.To a 6-hole plate was added F-10 Nutrient Mixure (Ham) medium containing 15% horse serum and 2.5% fetal bovine serum and C 6 rat glycoma cells to 1.0 x 10 5 cells / ml. The cells were incubated for 3 days at 37 ° C. in a 5% CO 2 incubator. Then, the test substance was added and incubated for 10 minutes at 37 degreeC, and 100 micrometers of 100 micrometers Ca ionization A 23187 was added, and it cultured for 10 minutes. The reaction stop solution (100 micrometers indomethacin 50mM EDTA) previously cooled with ice was added, and the culture supernatant was collect | recovered. 1N hydrochloric acid was added to the culture supernatant to pH 4, ethyl acetate was added thereto, and the resulting prostaglandin E 2 was transferred to the ethyl acetate layer. The ethyl acetate layer was recovered, dried under reduced pressure, and dissolved in 0.5 ml of 10 mM Tris-HCl buffer (pH 7.6). [3H] prostaglandin E 2 solution and prostaglandin E 2 antibody were added to this solution, and the mixture was reacted at 4 ° C for 24 hours. Then, charcoal liquid was added and centrifuged, the supernatant radioactivity was measured by the liquid scintillation counter, and the amount of free prostaglandin E 2 in the medium was quantified. The decrease in prostaglandin E 2 production according to the test substance to the prostaglandin E 2 production of the control containing no test substance was expressed as the prostaglandin E 2 production inhibition rate. The results are shown in Table 1.
시험예 2시클로옥시게나아제 활성저해시험 Test Example 2 Cyclooxygenase Inhibition Test
시클로옥시게나아제로서 양 정낭선 미크로솜을 사용한다. 시클로옥시게나아제 반응은, 최종농도 270㎍/㎖의 양 정낭선 미크로솜, 5mM 트리프토판, 1mM 페놀, 0.23mM 하이드로키논, 1μM 헥산, 20μM 아라키돈산을 포함하는 0.1M 인산 완충액(pH 7.5)에, 메탄올에 용해된 피험물질을 첨가하여, 37℃에서 10분간 반응시킨다. 반응액을 끓여서 반응을 정지시켜, 상청중의 프로스타글란딘 E2량을 EIA으로정량하였다. 피험물질을 함유하지 않은 콘트롤의 프로스타글란딘 E₂생성량에 대한 피험물질에 의한 프로스타글란딘 E₂생성량의 저하를 시클로키시게아제 저해율로 표시하였다. 그 결과를 표2에 나타낸다.Both seminal vesicle microsomes are used as cyclooxygenase. The cyclooxygenase reaction was carried out at 0.1 M phosphate buffer (pH 7.5) containing both seminal vesicle microsomal at a final concentration of 270 μg / ml, 5 mM tripptophan, 1 mM phenol, 0.23 mM hydrokinone, 1 μM hexane, 20 μM arachidonic acid. The test substance dissolved in methanol was added to the mixture, and reacted at 37 ° C for 10 minutes. The reaction solution was boiled to stop the reaction, and the amount of prostaglandin E 2 in the supernatant was quantified by EIA. The decrease in the amount of prostaglandin E 2 produced by the test subject to the amount of prostaglandin E 2 produced by the control which did not contain the test substance was expressed by the ratio of cyclokisagease. The results are shown in Table 2.
이들 시험예 1, 2의 결과에서, 본 발명의 망고스틴 추출물, α-망고스틴 및 γ-망고스틴은 프로스타글란딘 생합성 저해작용을 갖는 것, 또한 본 발명의 망고스틴 추출물, α-망고스틴 및 γ-망고스틴이 시클로옥시게나아제 저해작용을 갖는 것 때문에, 본 발명품은 포유동물의 프로스타글란딘이 병원성 물질로써 관여하고 있는 질병의 치료 및 예방에 유용하다.In the results of these test examples 1 and 2, the mangosteen extract, α-mangosteen and γ-mangosteen of the present invention have prostaglandin biosynthesis inhibitory activity, and also the mangosteen extract, α-mangosteen and γ- of the present invention. Because mangosteen has a cyclooxygenase inhibitory effect, the present invention is useful for the treatment and prevention of diseases in which prostaglandins of mammals are involved as pathogenic agents.
실시예 6산제 Example 6 Powder
유당 25부Lactose 25
감자전분 10부10 parts potato starch
실시예1의 추출물 5부5 parts extract of Example 1
실시예 7정제 Example 7 Tablets
D-만니톨 10부D-mannitol part 10
유당 10부Lactose, Part 10
결정셀룰로스 2부Crystalline Cells Part 2
히드록시프로필셀룰로스 1부Hydroxypropyl Cellulose Part 1
α-망고스틴 0.5부α-mangosteen 0.5part
실시예 8시럽제 Example 8 Syrups
단시럽 10부Sweet syrup part 10
카르복시메틸셀룰로스 1부Carboxymethylcellulose, part 1
γ-망고스틴 0.3부γ-mangosteen 0.3 part
실시예 9주사제 Example 9 Injection
클로로부탄올 0.5부0.5 part chlorobutanol
염화나트륨 0.9부Sodium chloride0.9part
주사용수 100부100 parts of water for injection
실시예 2의 추출물 1부1 part extract of Example 2
실시예 10캔디 Example 10 Candy
그래뉼 당 45부45 parts per granule
물엿( D.E. 42) 50부Starch syrup (D.E. 42) 50
물 20부20 parts water
γ-망고스틴 0.5부γ-mangosteen 0.5part
레몬 향료 1부Lemon Flavors, Part 1
실시예 11쵸콜렛 Example 11 Chocolate
카카오비터 20부Kakaobiter, part 20
카카오버터 17부Kakaover Part 17
설탕 43부43 parts of sugar
전지분유 20부20 parts powder
실시예2의 추출물 1부1 part extract of Example 2
바닐라 향료 0.1부0.5 Vanilla Flavors
실시예 12츄잉껌 Example 12 Chewing Gum
껌베이스 20부20 gum bases
설탕 56부56 parts sugar
물엿 13부Starch syrup part 13
포도당 10부10 parts glucose
연화제 1부Softener Part 1
실시예 3의 추출물 0.5부0.5 part extract of Example 3
민트향료 0.5부Mint Flavor 0.5
실시예 13정과 Example 13
설탕 75부75 parts sugar
포도당 19부Glucose Part 19
자당지방산에스테르 0.2부0.2 part sucrose fatty acid ester
실시예 4의 추출물 0.5부0.5 part extract of Example 4
물 4부4 parts water
본 발명의 망고스틴의 과피로부터 함수유기용제 또는 유기용제로 추출하여 얻은 추출물, α-망고스틴 및 γ-망고스틴을 유효성분으로 하는 시클로옥시게나아제 저해제는, 천연물로부터 조제가 가능한 것으로 부작용이 없어 안전하고, 우수한 시클로옥시게나아제 저해작용 및 프로스타글란딘 생합성저해작용을 갖기때문에, 이것에 기인하는 질병의 예방, 치료에 유효하다.The extract obtained by extracting a water-containing organic or organic solvent from the skin of the mangosteen of the present invention, the cyclooxygenase inhibitor containing α-mangosteen and γ-mangosteen as an active ingredient, can be prepared from natural products and has no side effects. Since it is safe and has excellent cyclooxygenase inhibitory effect and prostaglandin biosynthesis inhibitory effect, it is effective for the prevention and treatment of the disease resulting from this.
또, 본 발명의 시클로옥시게나아제 저해제는, 정미성(呈味性)에 우수하고, 이것을 음식품에 함유시키는 것으로 정미성이 우수한 시클로옥시게나아제 저해용 음식품을 제공할 수 있다.Moreover, the cyclooxygenase inhibitor of this invention can provide the food-drinks for cyclooxygenase inhibition which are excellent in taste and excellent in taste by including this in food-drinks.
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JP2000235023A JP4638977B2 (en) | 2000-08-02 | 2000-08-02 | Cyclooxygenase inhibitor |
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JPH07147951A (en) * | 1991-01-25 | 1995-06-13 | Asama Kasei Kk | Production of food preservative and highly preservable food |
JP2890212B2 (en) * | 1991-01-29 | 1999-05-10 | 有限会社野々川商事 | Cosmetics |
JPH0987155A (en) * | 1995-09-27 | 1997-03-31 | Shiseido Co Ltd | Ultraviolet light absorber and skin preparation for external use obtained by blending the same |
WO1997041825A1 (en) * | 1996-05-02 | 1997-11-13 | Technoble Co., Ltd. | Cosmetic |
JP3968405B2 (en) * | 1996-08-30 | 2007-08-29 | 株式会社ロッテホールディングス | Antiallergic agent |
JP3651733B2 (en) * | 1997-05-29 | 2005-05-25 | 御木本製薬株式会社 | Cosmetic drugs and medicinal cosmetics |
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KR100653948B1 (en) * | 2004-04-08 | 2007-04-16 | 롯데제과주식회사 | Ikappa;B KINASE INHIBITOR AND Ikappa;B KINASE INHIBITING COMPOSITION COMPRISING THEREOF |
KR100729436B1 (en) * | 2004-04-08 | 2007-06-15 | 롯데제과주식회사 | Food additive as IκB kinase inhibitor and food containing the same |
KR101508294B1 (en) * | 2012-07-05 | 2015-04-07 | 동국대학교 산학협력단 | Composition for preventing or treating Hepatitis C comprising extract of Garcinia Mangostana or Gamma, alpha-mangostins |
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JP4638977B2 (en) | 2011-02-23 |
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