KR101058587B1 - Oleanane triterpene saponin compounds which are effective on treatment of dementia and mild cognitive impairment, and improvement of cognitive function - Google Patents
Oleanane triterpene saponin compounds which are effective on treatment of dementia and mild cognitive impairment, and improvement of cognitive function Download PDFInfo
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- KR101058587B1 KR101058587B1 KR1020110027819A KR20110027819A KR101058587B1 KR 101058587 B1 KR101058587 B1 KR 101058587B1 KR 1020110027819 A KR1020110027819 A KR 1020110027819A KR 20110027819 A KR20110027819 A KR 20110027819A KR 101058587 B1 KR101058587 B1 KR 101058587B1
- Authority
- KR
- South Korea
- Prior art keywords
- dementia
- saponin
- triterpene saponin
- glucopyranosyl
- sugar
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- 229930182493 triterpene saponin Natural products 0.000 title claims abstract description 28
- 206010012289 Dementia Diseases 0.000 title abstract description 22
- 208000010877 cognitive disease Diseases 0.000 title abstract description 9
- 230000003920 cognitive function Effects 0.000 title abstract description 8
- 208000027061 mild cognitive impairment Diseases 0.000 title abstract description 8
- 238000011282 treatment Methods 0.000 title abstract description 6
- 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 title description 23
- 230000006872 improvement Effects 0.000 title description 2
- 230000000694 effects Effects 0.000 claims abstract description 20
- 235000013402 health food Nutrition 0.000 claims abstract description 12
- 230000003925 brain function Effects 0.000 claims abstract description 8
- -1 gyros Natural products 0.000 claims description 44
- 235000000346 sugar Nutrition 0.000 claims description 31
- NVSLBOBPSCMMSO-BVLVEXITSA-N [(2s,3r,4s,5s,6r)-6-[[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-[(2s,3r,4s,5s)-4,5-dihydroxy-3-[(2s,3r, Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](OC[C@@H]2[C@H]([C@H](O)[C@@H](O)[C@H](OC(=O)[C@@]34[C@@H](CC(C)(C)CC3)C=3[C@@]([C@]5(C)CC[C@H]6C(C)(C)[C@@H](O[C@H]7[C@@H]([C@@H](O)[C@@H](O)CO7)O[C@H]7[C@@H]([C@H](O)[C@@H](O)[C@H](C)O7)O)CC[C@]6(C)[C@H]5CC=3)(C)CC4)O2)O)[C@H](O)[C@H]1O NVSLBOBPSCMMSO-BVLVEXITSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- GBBVHDGKDQAEOT-UHFFFAOYSA-N 1,7-dioxaspiro[5.5]undecane Chemical compound O1CCCCC11OCCCC1 GBBVHDGKDQAEOT-UHFFFAOYSA-N 0.000 claims description 4
- DXLORNSIGDEVQK-ORHSKWSZSA-N C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC[C@H]3O[C@@H](OC(=O)[C@]45CCC(C)(C)C[C@H]4C4=CC[C@@H]6[C@@]7(C)CC[C@H](O[C@@H]8OC[C@H](O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)C(C)(C)[C@@H]7CC[C@@]6(C)[C@]4(C)CC5)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H]2CO)[C@H](O)[C@H](O)[C@H]1O Chemical compound C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC[C@H]3O[C@@H](OC(=O)[C@]45CCC(C)(C)C[C@H]4C4=CC[C@@H]6[C@@]7(C)CC[C@H](O[C@@H]8OC[C@H](O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)C(C)(C)[C@@H]7CC[C@@]6(C)[C@]4(C)CC5)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H]2CO)[C@H](O)[C@H](O)[C@H]1O DXLORNSIGDEVQK-ORHSKWSZSA-N 0.000 claims description 4
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Abstract
본 발명은 올레아난계 트리테르펜 사포닌 화합물이 감퇴된 기억력과 학습능력을 증진시키는 효과를 가지므로, 치매 및 경도인지장애 관련 질환의 치료제 및 인지기능 등의 뇌기능을 개선하는 건강식품의 유효성분으로서 올레아난계 트리테르펜 사포닌 화합물을 사용하는 용도에 관한 것이다.Since the present invention has an effect of improving the memory and learning ability of the oleonan-based triterpene saponin compound is reduced, as an active ingredient of a health food that improves the brain function, such as treatments and cognitive function of diseases related to dementia and mild cognitive impairment It relates to the use of the oleonan-based triterpene saponin compound.
Description
본 발명은 다음 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물이 감퇴된 기억력과 학습능력을 증진시키는 효과를 가지므로, 치매 및 경도인지장애 관련 질환의 치료제 및 인지기능 등의 뇌기능을 개선하는 건강식품의 유효성분으로서 올레아난계 트리테르펜 사포닌 화합물을 사용하는 용도에 관한 것이다.The present invention has the effect of improving the memory and learning ability of the oleonan-based triterpene saponin compound represented by the following formula (1), thereby improving brain functions such as treatments and cognitive functions for diseases related to dementia and mild cognitive impairment The present invention relates to the use of an oleonan-based triterpene saponin compound as an active ingredient of a health food.
상기 화학식 1에서, R1, R2 및 R3는 각각 수소원자 또는 C1-C4의 알킬기를 나타내고, R4는 C1-C4의 알킬기 또는 C1-C4의 하이드록시알킬기를 나타내고, R5 및 R6는 각각 수소원자 또는 당(sugar)이고, R5 및 R6 둘 중의 적어도 하나 이상은 당(sugar)을 나타내고, 이때 당(sugar)은 글루코스, 갈락토스, 람노스, 자이로스, 아라비노스, 및 글루쿠론산 중에서 선택된다.In Formula 1, R 1 , R 2 and R 3 each represent a hydrogen atom or an alkyl group of C 1 -C 4 , and R 4 represents an alkyl group of C 1 -C 4 or a hydroxyalkyl group of C 1 -C 4 . , R 5 And R 6 are each hydrogen or sugar, R 5 And at least one of R 6 represents sugar, wherein the sugar is selected from glucose, galactose, rhamnose, gyros, arabinose, and glucuronic acid.
트리테르펜 사포닌(triterpene saponin)은 사포게닌(sapogenin, aglycone)으로 트리테르펜을 가지며, 당(sugar)과 글리코시드 결합 또는 에스테르 결합을 이루고 있는 화합물을 일컫는다. 트리테르펜 사포닌은 사포게닌의 종류에 따라 구별되는데, 올레아난(oleanane), 우르산(ursane), 루판(lupane), 호판(hopane), 타라세란(taraxerane) 형 등의 5환성(pentacyclic) 트리테르펜을 사포게닌으로 가지는 사포닌이 대표적이다. 또한, 사포닌은 당쇄와의 결합 위치에 따라 구별되는데, 올레아놀산을 예로 들면 C-3 및 C-28 위치 중 어느 한곳에서 당쇄와 결합한 것을 모노데스모사이드(monodesmoside)라 하고, C-3 및 C-28 위치 두 곳에서 당쇄와 결합한 것을 비스데스모사이드(bisdesmoside)라 구분한다. C-3 위치에서는 주로 글리코시드 결합에 의해 당쇄와 결합을 이루고, C-28 위치에서는 주로 에스테르 결합에 의해 당쇄와 결합을 이룬다. 사포닌과 주로 결합하는 당(sugar)은 글루코스, 갈락토스, 람노스, 자이로스, 아라비노스, 글루쿠론산 등이다. Triterpene saponin (sapogenin, aglycone) has a triterpene, and refers to a compound that forms a glycoside bond or an ester bond with sugar. Triterpene saponins are classified according to the type of saponenin, pentacyclic triterpenes such as oleanane, ursane, lupane, hopane, and taraxerane. Saponin which has as a saponenin is typical. In addition, saponins are distinguished according to the binding position with sugar chains. For example, oleanoic acid, which binds with a sugar chain at any one of the C-3 and C-28 positions, is called monodesmoside, and C-3 and C- 28 The position of bisdesmoside is distinguished from the sugar chain in two places. In the C-3 position, the sugar chain is mainly bonded by glycosidic bond, and in the C-28 position, the sugar chain is mainly bonded by ester bond. Sugars that primarily bind saponins are glucose, galactose, rhamnose, gyros, arabinose, glucuronic acid, and the like.
사포닌은 비스데스모사이드(bisdesmoside) 상태로는 장내 흡수율이 매우 낮은 것으로 알려져 있다. 하지만 사포닌은 복용 시 장내 세균의 효소에 의해서 C-28 위치의 에스테르 결합이 쉽게 가수분해되어서 당쇄가 제거되고 C-3 위치의 글루코시드 결합으로 연결된 당쇄가 말단부터 순차적으로 일부 가수분해 된 후에 체내에 흡수된다 [Kim DH, Bae EA, Han MJ, Park HJ, Choi JW. Metabolism of Kalopanaxsaponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites. Biol Pharm Bull. 2002 Jan; 25(1): 68-71.]. 반면에 당(sugar)이 결합하지 않은 트리테르펜 사포게닌 자체는 용해도가 낮을 뿐만 아니라 장내 흡수율이 떨어져 여러 동물 실험에서 배당체에 비해 활성이 떨어지는 것으로 보고되었다 [Yoshikawa M, Matsuda H. Antidiabetogenic activity of oleanolic acid glycosides from medicinal foodstuffs. Biofactors. 2000; 13(1-4): 231-7]. Saponins are known to have very low intestinal absorption in the bisdesmoside state. However, saponin is easily hydrolyzed by the enzyme of intestinal bacteria at the time of taking so that the sugar chain is removed and the sugar chain connected by the glucosidic bond at the C-3 position is partially hydrolyzed sequentially from the end. Absorbed by Kim DH, Bae EA, Han MJ, Park HJ, Choi JW. Metabolism of Kalopanax saponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites. Biol Pharm Bull . 2002 Jan; 25 (1) : 68-71.]. On the other hand, triterpene sapogenin itself, which has no sugar binding, has not only low solubility but also low intestinal absorption rate, which has been reported to be less active than glycosides in several animal experiments. [Yoshikawa M, Matsuda H. Antidiabetogenic activity of oleanolic acid glycosides from medicinal foodstuffs. Biofactors . 2000; 13 (1-4) : 231-7].
우리나라는 물론 전 세계적으로 노인 인구가 증가하게 되면서 노인인구에 많은 각종 퇴행성 노인 질환들이 사회적, 경제적인 손실을 야기 시키고 있다. 미국 치매협회와 국립노화연구원이 발표한 통계를 보면 4백만 명의 미국인이 치매를 앓고 있으며 일반적으로 60세 이후 치매가 발병하지만 드문 경우 50대부터 시작하며 65세 이후 전 미국인의 10.3%가 치매를 갖고 있으며, 치매를 치료하는데 쓰여지는 비용은 연간 미국에서 950억 달러의 막대한 비용이 사용되고 있다.As the elderly population increases not only in Korea but also in the world, many degenerative diseases of the elderly are causing social and economic losses. Statistics released by the American Dementia Association and the National Institute of Aging indicate that 4 million Americans have dementia, typically dementia after age 60, but rarely start in their 50s and 10.3% of all Americans after age 65 The cost of treating dementia is $ 95 billion annually in the United States.
우리나라는 한국보건사회연구원의 보고서에서 고령화 현상으로 인해 치매인구가 급증하여 95년 치매 유병율은 65세 이상 노인 중 8.3% 이었으며, 2020년에는 이보다 0.7% 포인트 늘어난 9%로 추정되고 있다. 또한, 치매 유병율을 통계청이 밝힌 장래 추계인구에 적용한 결과, 2000년 치매 노인 수는 27만7천48명(65세 이상 노인인구의 8.3%), 2015년 52만7천68명(9%), 2020년 61만9천1백32명(9%)에 이를 것이라고 추정하고 있다. 치매질환은 환자 자신의 인간적인 삶을 황폐화시킬 뿐만 아니라 가족의 삶까지도 망가뜨리게 되는 질환이므로 심각한 사회적, 경제적 문제로 대두되고 있으므로 치료되어야 할 심각한 난치성 질환이다. In Korea, the report of the Korea Institute for Health and Social Affairs showed that the dementia population increased rapidly due to aging, and the prevalence of dementia in 1995 was 8.3% among elderly people over 65 years old, and it is estimated to increase by 0.7 percentage point to 9% in 2020. In addition, as a result of applying the prevalence of dementia to the prospective population revealed by the National Statistical Office, the number of elderly people with dementia in 2000 was 277,00048 (8.3% of the elderly aged 65 and over), 52,6868 people (9%) in 2015. It is estimated that it will reach 61,132 (9%) in 2020. Dementia disease is a serious incurable disease that must be treated because it is a serious social and economic problem because it not only destroys the patient's own human life but also destroys the family life.
치매질환은 다양한 원인으로 발병할 수 있으나, 주요한 증상은 학습과 기억력이 현저하게 감퇴되는 증상이 나타난다는 것이다. Dementia disease can be caused by a variety of causes, but the main symptom is a marked loss of learning and memory.
치매 치료제로서 처음으로 FDA공인을 받은 약인 1993년에 나온 타크린(Tacrine)은 초기 및 중기에 알쯔하이머병 환자들의 뇌에서 생성되는 아세틸콜린(ACh)이 분해되는 것을 억제함으로써 약 30% 정도의 환자에서 인지기능의 소실을 늦출 수 있었으나, 간과 관련된 부작용을 많이 일으키기 때문에 현재는 거의 사용되어지지 않고 있다. 1996년에 미국 FDA의 승인을 받은 아리셉트(Aricept)는 아세틸콜린의 이용도를 높임으로써 작용하는 것으로 취침 전 하루에 한번 복용으로 가능하며 부작용으로는 오심과 설사, 피곤감 등이 있으나 이러한 부작용들은 심하지 않고 곧 없어진다. 따라서, 부작용이 적으며, 효능이 좋은 새로운 치매치료제를 개발하는 것이 절실히 필요한 실정이다.
Tacrine, released in 1993 as the first FDA-approved drug to treat dementia, inhibits the breakdown of acetylcholine (ACh) produced in the brains of Alzheimer's disease patients in early and mid-stage by approximately 30% of patients. Loss of cognitive function could be delayed, but it is rarely used at present because it causes many side effects related to liver. Aricept, approved by the US FDA in 1996, works by increasing the use of acetylcholine, which can be taken once a day before bedtime. Side effects include nausea, diarrhea, and tiredness. Will disappear soon. Therefore, the development of a new dementia treatment with fewer side effects and good efficacy is urgently needed.
이에, 본 발명자들은 독성이 거의 없고 감퇴된 기억력 증진은 물론 학습능력 증진에 유용한 효과가 있는 뇌기능 개선제를 개발하기 위하여 연구한 결과, 올레아난계 트리테르펜 사포닌 화합물이 치매 및 경도인지 장애 치료 효과 및 인지 기능 개선 효과를 있음을 알게됨으로써 본 발명을 완성하게 되었다. Accordingly, the present inventors have studied to develop a brain function improver that is effective in improving the ability to learn as well as the reduced memory as well as reduced toxicity, as a result of the treatment of oleanic triterpene saponin compounds with dementia and mild cognitive impairment and The present invention has been completed by knowing that the cognitive function is improved.
따라서, 본 발명은 올레아난계 트리테르펜 사포닌 화합물이 유효성분으로 함유된 뇌기능 개선용 의약 및 건강식품을 제공하는데 그 목적이 있다.
Accordingly, an object of the present invention is to provide a medicament and health food for improving brain function containing an olean-based triterpene saponin compound as an active ingredient.
본 발명은 다음 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물이 함유되어 있는 치매 및 경도인지 장애 치료용 약제 또는 뇌기능 개선용 건강식품을 그 특징으로 한다. The present invention is characterized by a medicament for treating dementia and mild cognitive impairment or a health food for improving brain function, which contains an oleanane-based triterpene saponin compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서, R1, R2 및 R3는 각각 수소원자 또는 C1-C4의 알킬기를 나타내고, R4는 C1-C4의 알킬기 또는 C1-C4의 하이드록시알킬기를 나타내고, R5 및 R6는 각각 수소원자 또는 당(sugar)이고, R5 및 R6 둘 중의 적어도 하나 이상은 당(sugar)을 나타내고, 이때 당(sugar)은 글루코스, 갈락토스, 람노스, 자이로스, 아라비노스, 및 글루쿠론산 중에서 선택된다.In Formula 1, R 1 , R 2 and R 3 each represent a hydrogen atom or an alkyl group of C 1 -C 4 , and R 4 represents an alkyl group of C 1 -C 4 or a hydroxyalkyl group of C 1 -C 4 . , R 5 And R 6 are each hydrogen or sugar, R 5 And at least one of R 6 represents sugar, wherein the sugar is selected from glucose, galactose, rhamnose, gyros, arabinose, and glucuronic acid.
이와 같은 본 발명을 더욱 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in detail.
본 발명에 따른 상기 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물로서 대표되는, 다음 화학식 1a로 표시되는 올레아놀산 사포닌과 다음 화학식 1b로 표시되는 헤데라게닌 사포닌은 이미 당 분야에서 널리 잘 알려진 화합물이다.Represented as the oleanane-based triterpene saponin compound represented by the formula (1) according to the present invention, oleanolic acid saponin represented by the following formula (1a) and hederagenin saponin represented by the following formula (1b) are already well known compounds in the art .
상기 화학식 1a로 표시되는 올레아놀산 사포닌은 사포게닌으로 올레아놀산(oleanolic acid)을 갖는 화합물로서, 항암과 항염 [Li J, Guo WJ, Yang QY. Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15. World J Gastroenterol. 2002 Jun; 8(3): 493-5], 뇌신경 보호 [Qian YH, Liu Y, Hu HT, Ren HM, Chen XL, Xu JH. The effects of the total saponin of Dipsacus asperoides on the damage of cultured neurons induced by β-amyloid protein 25-35], 항바이러스 [Kapil A, Sharma S. Effect of oleanolic acid on complement in adjuvant- and carrageenan-induced inflammation in rats. J. Pharm Pharmacol . 1995 Jul; 47(7): 585-7], 항고지혈증 [Lee KT, Sohn IC, Kim DH, Choi JW, Kwon SH, Park HJ. Hypoglycemic and hypolipidemic effects of tectorigenin and kaikasaponin Ⅲ in the streptozotocin-lnduced diabetic rat and their antioxidant activity in vitro. Arch Pharm Res. 2000 Oct; 23(5): 461-6], 항알레르기 [Park KH, Park J, Koh D, Lim Y. Effect of saikosaponin-A, a triterpenoid glycoside, isolated from Bupleurum falcatum on experimental allergic asthma. Phytother Res . 2002 Jun; 16(4): 359-63], 면역조절 [Ju DW, Zheng QY, Cao X, Fang J, Wang HB. Esculentoside A inhibits tumor necrosis factor, interleukin-1, and interleukin-6 production induced by lipopolysaccharide in mice. Pharmacology. 1998 Apr; 56(4): 187-95], 혈관형성 억제[한국특허등록 제101,480호] 효능에 대해서는 이미 알려진 바 있다.The oleanolic acid saponin represented by Chemical Formula 1a is a compound having oleanolic acid as sapongenin, and is anticancer and anti-inflammatory [Li J, Guo WJ, Yang QY. Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15. World J Gastroenterol . 2002 Jun; 8 (3) : 493-5], Cerebral nerve protection [Qian YH, Liu Y, Hu HT, Ren HM, Chen XL, Xu JH. The effects of the total saponin of Dipsacus asperoides on the damage of cultured neurons induced by β-amyloid protein 25-35], an antivirus [Kapil A, Sharma S. Effect of oleanolic acid on complement in adjuvant- and carrageenan-induced inflammation in rats. J. Pharm Pharmacol . 1995 Jul; 47 (7) : 585-7], antihyperlipidemia [Lee KT, Sohn IC, Kim DH, Choi JW, Kwon SH, Park HJ. Hypoglycemic and hypolipidemic effects of tectorigenin and kaikasaponin III in the streptozotocin-lnduced diabetic rat and their antioxidant activity in vitro. Arch Pharm Res . 2000 Oct; 23 (5 ): 461-6], antiallergic [Park KH, Park J, Koh D, Lim Y. Effect of saikosaponin-A, a triterpenoid glycoside, isolated from Bupleurum falcatum on experimental allergic asthma. Phytother Res . 2002 Jun; 16 (4) : 359-63], immunomodulatory [Ju DW, Zheng QY, Cao X, Fang J, Wang HB. Esculentoside A inhibits tumor necrosis factor, interleukin-1, and interleukin-6 production induced by lipopolysaccharide in mice. Pharmacology . 1998 Apr; 56 (4) : 187-95], the efficacy of inhibiting angiogenesis [Korean Patent Registration No. 101,480] has already been known.
상기 화학식 1b로 표시되는 헤데라게닌 사포닌은 사포게닌으로 헤데라게닌(hederagenin)을 갖는 화합물로서, 항염 [Kwak WJ, Han CK, Chang HW, Kim HP, Kang SS, Son KH. Loniceroside C, an antiinflammatory saponin from Lonicera japonica. Chem Pharm Bull ( Tokyo ). 2003 Mar; 51(3): 333-5], 진통 [Choi J, Huh K, Kim SH, Lee KT, Park HJ, Han YN. Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals. J Ethnopharmacol. 2002 Feb; 79(2): 199-204], 항산화 [Choi J, Huh K, Kim SH, Lee KT, Lee HK, Park HJ. Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent. J Ethnopharmacol. 2002 Jan; 79(1): 113-8], 혈당억제 [Kim DH, Yu KW, Bae EA, Park HJ, Choi JW. Metabolism of Kalopanaxsaponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites. Biol Pharm Bull. 1998 Apr; 21(4): 360-5] 효능에 대해서는 이미 알려진 바 있다.Hederagen saponin represented by Formula 1b is a compound having hederagenin as sapogenin, and has anti-inflammatory properties [Kwak WJ, Han CK, Chang HW, Kim HP, Kang SS, Son KH. Loniceroside C, an antiinflammatory saponin from Lonicera japonica. Chem Pharm Bull ( Tokyo ) . 2003 Mar; 51 (3) : 333-5], analgesic [Choi J, Huh K, Kim SH, Lee KT, Park HJ, Han YN. Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals. J Ethnopharmacol . 2002 Feb; 79 (2) : 199-204], antioxidant [Choi J, Huh K, Kim SH, Lee KT, Lee HK, Park HJ. Kalopanax saponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent. J Ethnopharmacol . 2002 Jan; 79 (1) : 113-8], blood sugar suppression [Kim DH, Yu KW, Bae EA, Park HJ, Choi JW. Metabolism of Kalopanax saponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites. Biol Pharm Bull . 1998 Apr; 21 (4) : 360-5] Efficacy is already known.
그러나, 현재까지 발표된 결과에 의하면, 올레아놀산 사포닌, 헤데라게닌 사포닌을 대표적으로 포함하는 상기 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물의 치매 및 경도인지 장애 치료효과 및 뇌기능 개선 효과에 대해서는 전혀 알려진 바가 없다.However, according to the results published to date, the treatment effect of dementia and mild cognitive impairment and brain function improvement of the oleanane-based triterpene saponin compound represented by the formula (1) including oleanolic acid saponin and hederagenin saponin, None known.
다만, 일본특허공개 제2000-247993호에서는 올레아놀산이 시그마 수용체(sigma receptor)에 높은 친화성을 가지고 있음을 확인하고, 올레아놀산이 시그마 수용체와 관련있는 다양한 뇌질환 즉, 정신 분열증, 우울증, 근심, 뇌혈관질환, 노년기 행동 장애, 알츠하이머병, 파킨슨씨병, 헌팅턴씨병, 약물중독, 스트레스 등에 대해 효능이 있음을 언급하고 있을 뿐, 이들 질환치료와 직접적으로 관련된 in vivo 동물 실험 또는 신경세포를 이용한 in vitro 실험 결과에 대해서는 전혀 제시하지 않았다.However, Japanese Patent Application Laid-Open No. 2000-247993 confirms that oleanolic acid has a high affinity for sigma receptors, and oleanolic acid has various brain diseases related to sigma receptors, namely schizophrenia, depression, anxiety, and brain. vascular disease, old age disorder, Alzheimer's disease, Parkinson's disease, Huntington's disease, drug addiction, as you mentioned, and that the effect on stress, etc., in using these diseases directly in vivo animal experiments, or nerve cells involved in vitro No experimental results were presented.
사포게닌으로서 올레아놀산 또는 헤데라게닌을 가지는 올레아난계 트리테르펜 사포닌 화합물은 C-3 위치 또는 C-28 위치에 당(sugar)이 결합된 모노데스모사이드(monodesmoside) 화합물 또는 C-3와 C-28 위치에 동시에 당(sugar)이 결합된 비스데스모사이드(bisdesmoside) 화합물이 존재할 수 있다. 이러한 당쇄의 다양한 조합에 의해 아래에 예시한 바와 같이 150종 이상의 사포닌 화합물이 존재한다 [강삼식, 트리테르페노이드 사포닌, 서울대학교출판부, 1996, Tradimed 천연물 데이타베이스]. Oleanane-based triterpene saponin compounds having oleanoic acid or hederagenin as sapongenin are monodesmoside compounds having sugars bonded at the C-3 or C-28 position or C-3 and C- There may be a bisdesmoside compound in which sugar is bound at the 28 position. By various combinations of these sugar chains, there are more than 150 saponin compounds as illustrated below [Gangsamsik, Triterpenoid Saponins, Seoul National University Press, 1996, Tradimed Natural Products Database].
올레아놀산 사포닌 : Oleanolic acid saponins :
아키란토사이드(Achyranthoside) C, 아쿠토사이드(Acutoside) A∼G, 아케보사이드(Akeboside) Stj, 아네모사이드(Anemoside) A, 아라리아사포닌(Araliasaponin) XⅡ∼XVⅢ, 아라로사이드(Araloside) D, 아르벤소사이드(Arvensoside) A∼B, 베타불가로사이드(Betavulgaroside) IV∼V, 부프레우륨 차이니즈 트리테르펜 글리코사이드(Bupleurum chinense triterpene glycoside) S1, 카라가노사이드(Caraganoside) A, 치쿠세츄사포닌(Chikusetsusaponin) IB, IV, 시우지아노사이드(Ciwujianoside) A1, C4, C3, D1, 클레마티치네노사이드(Clematichinenoside) A, C, 클레마티스 차이니즈 프로사포게닌(Clematis chinensis prosapogenin) CP9, CP9a, CP7a, CP2b, 클레몬타노사이드(Clemontanoside) E, F, 샤프란(Crocus sativus) 올레아놀산 사포닌, 에라토사이드(Elatoside) B, D, 엘레우테로사이드(Eleutheroside) K, 팻시아사이드(Fatsiaside) A1, 헤데라콜키사이드(Hederacolchiside) E, 헤데라사포닌(Hederasaponin) B, 후장고사이드(Huzhangoside) A,B,C, 라브라보사이드(Lablaboside) A, 루시오사이드(Lucyoside) H, 6'-메틸모모딘 I, 모모딘(Momordin) I, IC, ⅡB, 3-O-α-L-아라비노피라노실올레아놀산, 3-O-α-L-아라비노피라노실올레아놀산-28-O-β-D-글루코실(1→6)β-D-글루코사이드, 3-O-α-L-람노피라노실(1→2)-α-L-아라비노피라노실올레아놀산-28-O-β-D-자이로피라노실(1→6)-β-D-글루코피라노실 에스테르, 3-O-β-D-갈락토피라노실(1→2)-β-D-글루쿠로노피라노실 올레아놀산, 3-O-β-D-글루코피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 올레아놀산, 3-O-β-D-글루코피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 올레아놀산-28-겐티오바이오사이드, 28-O-β-D-글루코피라노실 올레아놀산, 3-O-β-D-글루코피라노실 올레아놀산, 3-O-β-D-글루쿠로노피라노실 올레아놀산, 3-O-β-D-리보피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 올레아놀산, 3-O-β-D-자이로피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 올레아놀산, 3-O-β-D-자이로실 (1→4)-β-D-글루코실(1→4)-α-L-람노실(1→3)-β-D-글루코실(1→3)-α-L-람노실(1→2)-α-아라비노실 올레아놀산-28-O-β-D-글루코실(1→6)β-D-글루코실 에스테르, 2'-O-글루코피라노실 모모딘 Ic, 2'-O-글루코피라노실 모모딘 Iic, 3-O-β-D-자이로피라노실(1→4)-β-D-글루코피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노사이드 올레아놀산-28-O-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르, 올레아놀산 3-O-네오헤스페리도사이드, 올레아놀산-3-O-α-L-아라비노피라노실 28-O-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르, 올레아놀산-3-O-β-D-글루코피라노실(1→2)-α-L-아라비노피라노사이드, 페리카프사포닌(Pericarpsaponin) J3, 프로사포게닌(Prosapogenin) CP4, 퀴나토사이드(Quinatoside) D, 라데아닌(Raddeanin) A, C, D, E, F, 라데노사이드(Raddeanoside) R10, R11, 리부라리닌(Rivularinin), 스피나코사이드(Spinacoside) C, D, 스피나사포닌(Spinasaponin) A, 타라사포닌(Tarasaponin) Ⅱ, Ⅲ, VI, 테트라파넥스 파피리페륨 사포닌(Tetrapanax papyriferum saponin) R-3, R-1-a, R-4b, 우도사포닌(Udosaponin) 메틸 에스테르 A∼C.Achyranthoside C, Acutoside A-G, Akeboside Stj, Anemoside A, Araliasaponin XII-XVIII, Araloside ) D, Arvensoside A to B, Betavulgaroside IV to V, Bupreureum Chinese triterpene glycoside S1, Caraganoside A, Chicuse Chikusetsusaponin IB, IV, Cijiujianoside A1, C4, C3, D1, Clematichinenoside A, C, Clematis chinensis prosapogenin CP9, CP9a , CP7a, CP2b, Clemontanoside E, F, Crocus sativus oleanoic acid saponin, Elatoside B, D, Eleutheroside K, Fatsiaside A1 , Hederacolchiside E, He Hexaasaponin B, Huzhangoside A, B, C, Lablaboside A, Lucioside H, 6'-Methylmomodine I, Momordin I, IC , IIB, 3-O-α-L-arabinopyranosyloleanoic acid, 3-O-α-L-arabinopyranosyloleanoic acid-28-O-β-D-glucosyl (1 → 6) β-D- Glucoside, 3-O-α-L-rhamopyranosyl (1 → 2) -α-L-arabinopyranosyloleanoic acid-28-O-β-D-gyropyranosyl (1 → 6) -β-D- Glucopyranosyl ester, 3-O-β-D-galactopyranosyl (1 → 2) -β-D-glucuronopyranosyl oleanoic acid, 3-O-β-D-glucopyranosyl (1 → 3 ) -α-L-lamnopyranosyl (1 → 2) -α-L-arabinopyranosyl oleanoic acid, 3-O-β-D-glucopyranosyl (1 → 3) -α-L-lamnopyranosyl ( 1 → 2) -α-L-arabinopyranosyl oleanolic acid-28-genthiobioside, 28-O-β-D-glucopyranosyl oleanoic acid, 3-O-β-D-glucopyranosyl oleanoic acid, 3- O-β-D-glucuronopyranosyl ol Reanolic acid, 3-O-β-D-ribopyranosyl (1 → 3) -α-L-ramnopyranosyl (1 → 2) -α-L-arabinofyranosyl oleanoic acid, 3-O-β-D Gyropyranosyl (1 → 3) -α-L-Rhamnopyranosyl (1 → 2) -α-L-arabinopyranosyl oleanoic acid, 3-O-β-D-gyrosil (1 → 4) -β -D-glucosyl (1 → 4) -α-L-lamnosyl (1 → 3) -β-D-glucosyl (1 → 3) -α-L-lamnosyl (1 → 2) -α-aravies Nosyl oleanolic acid-28-O-β-D-glucosyl (1 → 6) β-D-glucosyl ester, 2'-0-glucopyranosyl momodine Ic, 2'-0-glucopyranosyl momodine Iic, 3-O-β-D-gyropyranosyl (1 → 4) -β-D-glucopyranosyl (1 → 3) -α-L-rhamnopyranosyl (1 → 2) -α-L-arabinofi Lanoside oleanolic acid-28-O-β-D-glucopyranosyl (1 → 6) -β-D-glucopyranosyl ester, oleanoic acid 3-O-neosperidoxide, oleanoic acid-3-O-α-L Arabinopyranosyl 28-O-β-D-glucopyranosyl (1 → 6) -β-D-glucopyranosyl ester, oleanoic acid-3-O-β-D-glucoy Lanosyl (1 → 2) -α-L-arabinopyranoside, Pericarpsaponin J3, Prosapogenin CP4, Quinatoside D, Radeanin A, C , D, E, F, Radedeanoside R10, R11, Riburinin (Rivularinin), Spinacoside C, D, Spinasaponin A, Tarasaponin II, III , VI, Tetrapanax papyriferum saponin R-3, R-1-a, R-4b, Udosaponin methyl esters A-C.
헤데라게닌 사포닌: Hederagenin saponins :
아케비아 사포닌 A ∼ G, 아케보사이드(Akeboside), 아스페로사포닌(Asperosaponin) F, H1, 칼코사이드(Calcoside) D, 카우로사이드(Cauloside) D, F, 클레마티스 차이니즈 프로사포게닌(Clematis chinensis prosapogenin) CP10, CP10a, Cp8a, CP3b, CP0, CP3a, CP2a, 3-O-β-D-자이로피라노실(1→3)-α-L-아라비노피라노실 헤데라게닌-28-O-α-L-람노피라노실(1→4)-β-D-글루코피라노실(1→6)-β-D-글루코피라노사이드, 헤데라게닌-3-O-α-L-아라비노사이드, 헤데라게닌-3-O-[α-L-람노피라노실-(1→2)-α-L-아라비노피라노실]-28-O-β-D-자이로피라노실(1→6)-β-D-글루코피라노실 에스테르, 헤데라게닌-3-O-[α-L-람노피라노실(1→2)-α-L-아라비노피라노실]-28-O-[3-O-아세틸-β-D-글루코피라노실(1→6)-β-D-글루코피라노사이드, 헤데라게닌-3-O-[α-L-람노피라노실(1→2)-α-L-아라비노피라노실]-28-O-[3-O-아세틸-β-D-자이로피라노실(1→6)-β-D-글루코피라노사이드, 헤데라게닌-3-O-α-L-람노피라노실(1→3)-β-D-글루코피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 28-O-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르, 헤데라게닌-3-O-β-D-글루코피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 28-O-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르, 헤데라게닌-3-O-(4-O-아세틸)-α-L-아라비노피라노실 28-O-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르, 카로파낙사포닌(Kalopanaxsaponin) B, G, JLa, JLb, 레온토사이드(Leontoside) A, B, 루시오사이드(Lucyoside) A, E, 무코로지사포닌(Mukurozisaponin) EI, G, X, Y2, YI, 4'-O-아세틸아케비아사포닌 D, 3-O-[α-L-아라비노실]헤데라게닌-28-O-[β-D-글루코실]에스테르, 3-O-α-L-람노피라노실(1→3)β-D-글루코실(1→3)α-D-람노실(1→2)α-아라비노실 헤데라게닌-28-O-β-D-글루코실(1→6)β-D-글루코실 에스테르, 3-O-β-D-글루코피라노실(1→3)-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 헤데라게닌, 3-O-β-D-글루코피라노실 헤데라게닌, 3-O(β-D-글루코실(1→4)α-L-람노실(1→3)β-D-글루코실(1→3)α-D-람노실(1→2)α-아라비노실 헤데라게닌-28-O-β-D-글루코실(1→6)β-D-글루코실 에스테르, 3-O(β-D-글루코실(1→4)α-L-람노실(1→3)β-D-글루코실(1→3)α-L-람노실(1→2)α-아라비노실 헤데라게닌, 3-O(β-D-자이로실(1→4)β-D-글루코실(1→4)α-L-람노실(1→3)β-D-글루코실(1→3)α-L-아라비노실(1→2)α-아라비노실 헤데라게닌, 3-O-[(2'-O-아세틸)-α-L-아라비노피라노실(1→6)-β-D-글루코피라노실]헤데라게닌, 3-O-(2'-O-아세틸)-α-L-아라비노피라노실 헤데라게닌-28-O-[β-D-글루코피라노실(1→6)-β-D-글루코피라노사이드], 퍼캅사포닌(Percarpsaponin) C, J2, G, K, 풀사티로사이드(Pulsatiloside) A, B, C, 퀴나토사이드(Quinatoside) A, B, C, 사핀도사이드(Sapindoside) A, B, C, 스타우노사이드(Staunoside) A, B, D, E, 타우로사이드(Tauroside) G3, 우도사포닌(Udosaponin) 메틸 에스테르 D, E, F. Akevia saponins A to G, Akeboside, Asperosaponin F, H1, Calcoside D, Cauroside D, F, Clematis Chinese Prosapogenin (Clematis chinensis) prosapogenin) CP10, CP10a, Cp8a, CP3b, CP0, CP3a, CP2a, 3-O-β-D-gyropyranosyl (1 → 3) -α-L-arabinofyranosyl hederagenin-28-O-α -L-ramnopyranosyl (1 → 4) -β-D-glucopyranosyl (1 → 6) -β-D-glucopyranoside, hederagenin-3-O-α-L-arabinoside, Hederagenin-3-O- [α-L-lamnopyranosyl- (1 → 2) -α-L-arabinopyranosyl] -28-O-β-D-gyropyranosyl (1 → 6)- β-D-glucopyranosyl ester, hederagenin-3-O- [α-L-ramnopyranosyl (1 → 2) -α-L-arabinopyranosyl] -28-O- [3-O- Acetyl-β-D-glucopyranosyl (1 → 6) -β-D-glucopyranoside, hederagenin-3-O- [α-L-rhamnopyranosyl (1 → 2) -α-L- Arabinopyranosyl] -28-O- [3-O-acetyl-β-D-gyropyranosyl (1 6) -β-D-glucopyranoside, hederagenin-3-O-α-L-rhamnopyranosyl (1 → 3) -β-D-glucopyranosyl (1 → 3) -α-L- Rhamnopyranosyl (1 → 2) -α-L-arabinopyranosyl 28-O-β-D-glucopyranosyl (1 → 6) -β-D-glucopyranosyl ester, hederagenin-3-O -β-D-glucopyranosyl (1 → 3) -α-L-lamnopyranosyl (1 → 2) -α-L-arabinofyranosyl 28-O-β-D-glucopyranosyl (1 → 6 ) -β-D-glucopyranosyl ester, hederagen-3-O- (4-O-acetyl) -α-L-arabinofyranosyl 28-O-β-D-glucopyranosyl (1 → 6 ) -β-D-glucopyranosyl ester, Carlopanaxsaponin B, G, JLa, JLb, Leontoside A, B, Luciyoside A, E, Mucorozisaponin EI, G, X, Y2, YI, 4'-O-acetylakebiasaponin D, 3-O- [α-L-arabinosyl] hederagenin-28-O- [β-D-glucosyl] ester , 3-O-α-L-rhamnopyranosyl (1 → 3) β-D-glucosyl (1 → 3) α-D-lamnosyl (1 → 2) α-ara Nosyl hederagenin-28-O-β-D-glucosyl (1 → 6) β-D-glucosyl ester, 3-O-β-D-glucopyranosyl (1 → 3) -α-L-rhamno Pyranosyl (1 → 2) -α-L-arabinopyranosyl hederagenine, 3-O-β-D-glucopyranosyl hederagenin, 3-O (β-D-glucosyl (1 → 4) α-L-Rhamnosyl (1 → 3) β-D-glucosyl (1 → 3) α-D-Rhamnosyl (1 → 2) α-arabinosyl hederagenin-28-O-β-D-glucose Sil (1 → 6) β-D-glucosyl ester, 3-O (β-D-glucosyl (1 → 4) α-L-lamnosyl (1 → 3) β-D-glucosyl (1 → 3) α-L-Rhamnosyl (1 → 2) α-arabinosyl hederagenine, 3-O (β-D-gyrosil (1 → 4) β-D-glucosyl (1 → 4) α-L- Rhamnosyl (1 → 3) β-D-glucosyl (1 → 3) α-L-arabinosyl (1 → 2) α-arabinosyl hederagenine, 3-O-[(2'-O-acetyl) -α-L-arabinopyranosyl (1 → 6) -β-D-glucopyranosyl] hederagenin, 3-O- (2'-O-acetyl) -α-L-arabinofyranosyl hedera Genine-28-O- [β-D-glucopyranosyl (1 → 6) -β-D-glucopyranoside], percapsaponin (Percarpsap onin) C, J2, G, K, Pulsatiloside A, B, C, Quinatoside A, B, C, Sapindoside A, B, C, Staunoside (Staunoside) A, B, D, E, Tauroside G3, Udosaponin methyl esters D, E, F.
올레아놀산 사포닌 및 헤데라게닌 사포닌을 대표적으로 포함하는 올레아난계 트리테르펜 사포닌 화합물은 일반적인 추출방법에 의해 다음에서 예시하는 식물로부터 추출되고 있다 : 비름과(Amaranthaceae) 식물 예를 들면 쇠무릎(Achyranthes sp.), 비름(Amaranthus sp.) 등, 두릅나무과(Araliaceae) 식물 예를 들면 오갈피(Acanthopanax sp.), 두릅(Aralia sp.), 팔손이(Fatsia sp.), 음나무(Kalopanax sp.), 인삼(Panax sp.), 통탈목(Tetrapanax sp.) 등, 바셀라세과(Basellaceae) 식물 예를 들면 보싱걸루티아(Boussingaultia sp.) 등, 매자나무과(Berberidaceae) 식물 예를 들면 꿩의다리아재비(Caulophyllum sp.) 등, 지치과(Boraginaceae) 식물 예를 들면 앤츄사(Anchusa sp.) 등, 인동과(Caprifoliaceae) 식물 예를 들면 인동(Lonicera sp.) 등, 명아주과(Chenopodiaceae) 식물 예를 들면 명아주(Chenopodium sp.) 등, 박과(Cucurbitaceae) 식물 예를 들면 뚜껑덩굴(Actinostemma sp.), 수세미(Luffa sp.), 여주(Momordica sp.) 등, 산토끼꽃과(Dipsacaceae) 식물 예를 들면 산토끼꽃(Dipsacus sp.) 등, 대극과(Euphorbiaceae) 식물 예를 들면 프트란지바(Putranjiva sp.) 등, 칠엽수과(Hippocastanaceae) 식물 예를 들면 칠엽수(Aesculus sp.) 등, 으름덩굴과(Lardizabalaceae) 식물 예를 들면 으름덩굴(Akebia sp.) 등, 콩과(Leguminosae) 식물 예를 들면 아카시아(Acacia sp.), 자귀나무(Albizzia sp.), 스와르치아(Swartzia sp.) 등, 오피리아과(Opiliaceae) 식물 예를 들면 오피리아(Opilia sp.) 등, 자리공과(Phytolaccaceae) 식물 예를 들면 자리공(Phytolacca sp.) 등, 미나리아재비과(Ranunculaceae) 식물 예를 들면 아네모네(Anemone sp.), 클레마티스(Clematis sp.), 헤데라(Hedera sp.), 할미꽃(Pulsatilla sp.) 등, 꼭두서니과(Rubiaceae) 식물 예를 들면 란디아(Randia sp.), 세롬피스(Xeromphis sp.) 등, 무환자나무과(Sapindaceae) 식물 예를 들면 포메티아(Pometia sp.), 스핀더스(Spindus sp.), 티노우이아(Thinouia sp.) 등, 마타리과(Valerianaceae) 식물 예를 들면 패트리니아(Patrinia sp.) 등.
Oleanane-based triterpene saponin compounds, which typically include oleanolic acid saponins and hederagenin saponins, are extracted from the plants exemplified by the following general extraction methods: Amaranthaceae plants, for example Achyranthes sp.), amaranth (Amaranthus sp.), etc., Araliaceae (Araliaceae), for plants For senticosus (Acanthopanax sp.), aralia (Aralia sp.), Fatsia Japonica (Fatsia sp.), kalopanax (Kalopanax sp.), Ginseng ( Panax sp.), Tetrapanax sp., Etc. Basellaceae plants, for example Boussingaultia sp.), Berberidaceae plants, such as Caulophyllum sp., Boraginaceae plants, such as Anchusa sp., Caprifoliaceae plants, etc. . g honeysuckle (Lonicera sp.), etc., chenopodiaceae (chenopodiaceae) plants, for example goosefoot (Chenopodium sp.), etc., watermelon and (Cucurbitaceae) plants, for example the lid vines (Actinostemma sp.), sponge gourd (Luffa sp.), Dipsacaceae plants, such as Momordica sp., For example Dipsacus sp., Etc. Euphorbiaceae plants, such as Putranjiva sp., Etc., Hippocastanaceae Plants such as Aesculus sp., Lardizabalaceae plants such as Akebia sp., Leguminosae plants such as Acacia sp. Albizzia sp.), Swartzia sp., Etc. Examples of Opiliaceae plants Opilia sp., Etc., Phytolaccaceae plants, for example Phytolacca sp., Etc. Ranunculaceae plants, for example Anemone sp., Clematis sp.), Hedera sp.), Pulsatilla sp.), Rubiaceae plants, for example Randia sp.), serom piece (Xeromphis sp.), etc., sapindaceae (Sapindaceae), for example plants Pomeranian thiazole (Pometia sp.), spin Ranges (Spindus sp.), Thinouia sp.), Valerianaceae plants, for example Patrinia sp.) and the like.
본 발명자들에 의한 동물 실험결과에 의하면, 스코플라민(scopolamine) 및 약물을 투여하지 않은 대조군(control), 신경전달물질의 전달방해를 통해 기억력을 감퇴시킨다고 알려진 스코플라민(1 mg/kg)을 투여한 그룹, 그리고 스코플라민 투여후 1시간 뒤에 상기 화학식 1로 표시되는 올레아난(oleanane)계 트리테르펜 사포닌 화합물을 투여한 그룹간의 기억력 증진을 평가한 결과 유의성 있는 활성을 보여주었다.According to the results of animal experiments by the inventors of the present invention, scopolamine (scopolamine) and a drug-free control (control), scoflavin (1 mg / kg) known to reduce memory through the interruption of the transmission of neurotransmitters As a result of evaluating memory enhancement between the group administered with and the group administered with the oleanane-based triterpene saponin compound represented by Formula 1 1 hour after the administration of scoflavin, a significant activity was shown.
따라서, 상기 화학식 1로 표시되는 올레아난(oleanane)계 트리테르펜 사포닌 화합물은 치매 및 경도인지 장애 치료용 약제 및 인지 기능 개선용 건강식품의 유효 활성성분으로 사용 가능하다.Therefore, the oleanane-based triterpene saponin compound represented by Formula 1 may be used as an active ingredient of a medicament for treating dementia and mild cognitive disorders and a health food for improving cognitive function.
상기 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물을 유효성분으로 함유하는 약제의 경우, 임상 투여 시에 경구 또는 비경구로 투여가 가능한 일반적인 의약품 제제의 형태로 제공될 수 있다. 경구 또는 비경구 투여를 위한 제제화 과정에서는 통상적으로 사용되고 있는 약제학적 또는 식품학적으로 허용 가능한 충진제, 증량제, 결합제, 습윤제, 붕해제, 계면활성제 등의 희석제 또는 부형제를 사용할 수 있다.In the case of a medicament containing an olean-based triterpene saponin compound represented by Chemical Formula 1 as an active ingredient, it may be provided in the form of a general pharmaceutical formulation that can be administered orally or parenterally during clinical administration. In the formulation process for oral or parenteral administration, pharmaceutically or food acceptable acceptable fillers, extenders, binders, wetting agents, disintegrating agents, surfactants, and the like can be used.
경구투여를 위한 고형 제제로는 정제, 환제, 산제, 과립제, 캅셀제 등이 포함되며, 이러한 고형 제제는 리그난과 락톤 화합물 및 그의 유도체에 적어도 하나 이상의 부형제, 예를 들면 전분, 칼슘 카보네이트, 수크로스 또는 락토오스, 젤라틴 등을 섞어 조제된다. 또한, 단순한 부형제 이외에 마그네슘 스테아레이트, 탈크 같은 윤활제들도 사용된다. 경구투여를 위한 액상 제제로는 현탁제, 내용액제, 유제, 시럽제 등이 해당되는데 흔히 사용되는 단순 희석제인 물, 액체 파라핀 이외에 여러 가지 부형제, 예를 들면 습윤제, 감미제, 방향제, 보존제 등이 포함될 수 있다.Solid preparations for oral administration include tablets, pills, powders, granules, capsules and the like, which solid preparations comprise at least one excipient such as starch, calcium carbonate, sucrose or the like in lignan and lactone compounds and derivatives thereof. It is prepared by mixing lactose and gelatin. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used. Liquid preparations for oral administration include suspensions, solvents, emulsions, and syrups. In addition to the commonly used simple diluents, water and liquid paraffin, various excipients such as wetting agents, sweeteners, fragrances, and preservatives may be included. have.
비경구 투여를 위한 제제에는 멸균된 수용액, 비수용성 용제, 현탁제, 유제, 동결건조제, 좌제가 포함된다. 비수용성 용제, 현탁제로는 프로필렌글리콜, 폴리에틸렌글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테르 등이 사용될 수 있다. 좌제의 기제로는 위텝솔, 마크로골, 트윈 61, 카카오지, 라우린지, 글리세롤젤라틴 등이 사용될 수 있다.Formulations for parenteral administration include sterile aqueous solutions, water-insoluble solvents, suspensions, emulsions, lyophilizers, suppositories. As the non-aqueous solvent and suspending agent, propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate and the like can be used. As the base of the suppository, utopsol, macrogol, tween 61, cacao butter, laurin butter, glycerol gelatin and the like can be used.
본 발명에 따른 약제 내 유효성분의 함유량은 체내에서의 활성 성분의 흡수도, 불활성화율, 배설속도, 사용자의 연령, 성별 및 상태 등에 따라 적절히 선택할 수 있다. 상기 화학식 1로 표시되는 올리아난계 트리테르펜 사포닌 화합물을 기준으로 한 1일 투여용량은 0.1 ∼ 10 mg/kg이며, 바람직하게는 0.5 ∼ 5 ㎎/㎏이며, 하루 1 ∼ 3회 투여할 수도 있다.The content of the active ingredient in the drug according to the present invention can be appropriately selected depending on the absorbency, inactivation rate, excretion rate, age, gender and condition of the active ingredient in the body. The daily dosage based on the olanan-based triterpene saponin compound represented by the formula (1) is 0.1 to 10 mg / kg, preferably 0.5 to 5 mg / kg, and may be administered 1 to 3 times a day. .
또한, 상기 화학식 1로 표시되는 올리아난계 트리테르펜 사포닌 화합물은 이를을 유효성분으로 함유하는 건강식품 형태로 제공될 수 있다. 본 발명에서의 건강식품이란, 상기 화학식 1로 표시되는 올리아난계 트리테르펜 사포닌 화합물을 일반 식품에 첨가하거나, 또는 캅셀화, 분말화, 현탁액 등으로 제조한 식품으로, 이를 섭취할 경우 건강상 특정한 효과를 가져오는 것을 의미하나, 일반 약품과는 달리 식품을 원료로 하여 약품의 장기복용시 발생할 수 있는 부작용 등이 없는 장점이 있다.
In addition, the olanan-based triterpene saponin compound represented by Formula 1 may be provided in the form of a health food containing it as an active ingredient. The health food in the present invention is a food prepared by adding the olanan-based triterpene saponin compound represented by the formula (1) to general foods, or by encapsulating, powdering, suspensions, and the like. Means to bring the effect, unlike the general medicine has the advantage that there is no side effect that can occur when using the drug as a raw material for long-term use.
이상에서 설명한 바와 같이, 상기 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물은 기억력 증진 효과가 우수하므로 치매 및 경도인지장애 관련 질환에 대한 치료약물 및 인지기능 등의 뇌기능 향상 효능의 건강식품으로서 유용하다.
As described above, the oleanane-based triterpene saponin compound represented by Chemical Formula 1 has excellent memory enhancement effect, and thus is a health food for improving brain function such as therapeutic drugs and cognitive function for diseases related to dementia and mild cognitive impairment. useful.
도 1은 본 발명의 올레아난계 트리테르펜 사포닌 화합물을 각각 1회 경구 투여하여 스코폴라민(Scopolamine)에 의한 감퇴된 기억력 증진효과 정도를 나타내는 그래프이다.FIG. 1 is a graph showing the degree of memory-improving effect by scopolamine by oral administration of the olean-based triterpene saponin compound of the present invention once.
이하, 본 발명은 다음 실시예에 의거하여 더욱 상세히 설명하겠는바, 본 발명이 이에 한정되는 것은 아니다.
Hereinafter, the present invention will be described in more detail based on the following examples, but the present invention is not limited thereto.
실시예Example 1: One: 올레아난계Oleanan system 트리테르펜Triterpenes 사포닌 추출 Saponin Extract
기존 문헌에서 올레아놀산 사포닌과 헤데라게닌 사포닌이 다량 함유된 것으로 보고된 아래 생약재로부터 올레아놀산 사포닌과 헤데라게닌 사포닌을 다음과 같은 방법으로 분리하였다. The oleanolic acid saponin and hederagenine saponin were isolated from the following herbal medicines, which have been reported to contain a large amount of oleanolic acid saponin and hederagenin saponin in the existing literature.
목두채 (Arlaia elata), 백두옹 (Pulsatilla chinensis ), 인동등 (Lonicera japonica), 해동피 (Kalopanax pictus)를 건조 중량 1 kg 씩 취하여 7 L의 50% 에탄올에 4시간 동안 환류하면서 추출하였고 이 과정을 2회 실시하였다. 추출액을 여과한 후 증류기(rotary evaporator)로 50 ℃에서 감압 농축하였고, 그 결과로 얻어진 농축물에 물을 첨가하여 원 생약중량 대비 5배량(V/W) 정도가 되도록 현탁한 후 동량의 수포화 노말-부탄올과 혼합하여 분리장치(separation funnel)에 넣고, 교반 후 24시간 동안 방치하여 상층의 부탄올층만을 분리하였다. 2∼3회 더 재 분획하고, 증류기를 이용하여 부탄올 분획물을 농축한 후, 진공 오븐에서 용매를 완전히 제거하여 건조시켰다. Throat ( Arlaia) elata ), Baekduong ( Pulsatilla chinensis ) , light bulb ( Lonicera japonica), thawed blood ( Kalopanax pictus ) was taken at 1 kg of dry weight and extracted with 7 L of 50% ethanol for 4 hours at reflux. The extract was filtered and concentrated under reduced pressure at 50 ° C. with a rotary evaporator. Suspended to about 5 times the original crude weight (V / W) by adding water to the resulting concentrate, followed by equal saturation. The mixture was mixed with normal-butanol, placed in a separation funnel, and left for 24 hours after stirring to separate only the upper butanol layer. The fractions were re-distilled two to three times more, and the butanol fractions were concentrated using a distiller and then dried by removing the solvent completely in a vacuum oven.
상기의 노말 부탄올 분획물에 대해 옥타데실실릴화한 실리카 레진(YMC*GEL ODS-A 12 nm, S-150 m)으로 컬럼 크로마토그래피를 수행하였다. 레진의 양은 시료 양 10 g의 25 배량인 250 g을 사용하였고 용매는 10%(v/v) 메탄올 수용액부터 10%(V/V)씩 메탄올 양을 늘려가며 레진 부피의 2 ∼ 3 배량의 용매를 스텝-그래디언트(step-gradient) 방식을 사용하였다. 사포닌 화합물을 최대한 농축하기 위해서 70%, 80%, 90% 메탄올 수용액(V/V)에 의해서 분리된 분획물만을 취하였다.
Column chromatography was performed on the normal butanol fraction with octadecylsilylated silica resin (YMC * GEL ODS-A 12 nm, S-150 m). The amount of resin used was 250 g, which is 25 times the amount of 10 g of the sample, and the solvent was 2-3 times the volume of the resin by increasing the amount of methanol by 10% (V / V) from 10% (v / v) aqueous methanol solution. Was used as a step-gradient method. Only fractions separated by 70%, 80%, 90% aqueous methanol solution (V / V) were taken to maximize concentration of the saponin compound.
실시예Example 2: 2: 올레아난계Oleanan system 트리테르펜Triterpenes 사포닌의 성분 단일 분리 및 구조 분석 Component Single Separation and Structural Analysis of Saponins
상기의 메탄올 수용액 분획물을 아세토나이트릴(Acetonitrile)과 물의 혼합용매로 사용한 고성능액체크로마토그래피(High performance liquid chromatography, HPLC)와 PDA 검출기를 이용한 분석을 통하여 210 nm에서 최대 흡광도를 가지며 트리테르펜 특유의 흡광 스펙트럼을 보이는 주요 피크를 선정하였다. 이어서 다시 분당 9.5 ㎖의 아세토나이트릴(Acetonitrile)과 물의 혼합용매를 사용한 Preparative HPLC을 이용하여 선정된 피크를 순수 분리하였으며 증류기를 이용하여 농축하였고 진공 오븐에서 용매를 완전히 제거하여 건조시켰다. 사용한 컬럼은 YMC J'Sphere ODS-H80이고, 측정파장은 210 nm에서 성분 분리를 수행하였다. 또한 분리된 피크의 성분을 2N H2SO4의 산 조건에서 100 ℃로 60분 간 가열하여 산 가수분해를 함으로써 사포닌에서 당을 제거하였다. 이 가수분해 산물을 시그마에서 구입한 올레아놀산과 헤데라게닌 표준물질과 함께 HPLC 분석하여 분리된 피크의 성분이 올레아놀산 사포닌이거나 헤데라게닌 사포닌임을 확인이 된 성분에 대해서 추가의 성분 분리를 진행하여 다음 표 1과 같은 8 개의 단일 물질을 확보하였다.
High performance liquid chromatography (HPLC) using acetonitrile and water as a mixed solvent of methanol aqueous solution fractions and analysis using a PDA detector have a maximum absorbance at 210 nm and are specific to triterpenes. The main peak showing the spectrum was selected. Subsequently, the selected peaks were separated purely using Preparative HPLC using a mixed solvent of 9.5 ml of acetonitrile and water per minute, concentrated using a distillation apparatus, and dried by completely removing the solvent in a vacuum oven. The column used was YMC J'Sphere ODS-H80, and the wavelength was measured at 210 nm. In addition, sugars were removed from saponins by heating the components of the separated peaks at 100 ° C. for 60 minutes under acidic conditions of 2N H 2 SO 4 . HPLC analysis of the hydrolyzate with oleanolic acid and hederagenine standard purchased from Sigma proceeded to further component separation for the component identified as oleanolic acid saponin or hederagenine saponin. Eight single materials such as 1 were obtained.
분리된 단일 물질의 구조 결정을 위해 1H-NMR(500 MHz), 13C-NMR(125 MHz), DEPT, 2D NMR(1H-1H COSY, HMQC, HMBC, TOCSY, NOESY)를 측정하였고, 이 데이터를 바탕으로 구조 결정을 수행하였다. 또한 산 가수분해된 당은 탄수화물 분석 시스템(carbohydrate analysis system) 및 TMS 유도체화한 후 GC로 분석하여 당의 종류와 수를 확인하였다. 각 당의 구조 분석은 2D NMR(1H-1H COSY, HMQC, HMBC, TOCSY)을 통해 수행하였으며, 당의 연결은 2D NMR(HMBC, NOESY)을 이용하였다. 1 H-NMR (500 MHz), 13 C-NMR (125 MHz), DEPT, 2D NMR ( 1 H- 1 H COZY, HMQC, HMBC, TOCSY, NOESY) were measured to determine the structure of the isolated single material. Based on this data, structural decisions were made. Acid hydrolyzed sugars were carbohydrate analysis system and TMS derivatization and analyzed by GC to confirm the type and number of sugars. Structural analysis of each sugar was performed by 2D NMR ( 1 H- 1 H COSY, HMQC, HMBC, TOCSY), and the linkage of sugar was performed by 2D NMR (HMBC, NOESY).
상기의 방법을 이용하여 다음 표 1과 같은 8종의 올레아놀산 사포닌 또는 헤데라게닌 사포닌 100 ∼ 500 mg을 확보하였다. Using the above method, 100 to 500 mg of eight oleanolic acid saponins or hederagen saponins as shown in Table 1 were obtained.
(3-O-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 올레아놀산)Eleutheroside K
(3-O-α-L-ramnopyranosyl (1 → 2) -α-L-arabinopyranosyl oleanoic acid)
(Pulsatilla
chinensis)Baekduong
( Pulsatilla
chinensis )
(3-O-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 올레아놀산-28-O-α-L-람노피라노실(1→4)-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르)Hederasaponin B
(3-O-α-L-lamnopyranosyl (1 → 2) -α-L-arabinopyranosyl oleanoic acid-28-O-α-L-lamnopyranosyl (1 → 4) -β-D-glucose Pyranosyl (1 → 6) -β-D-glucopyranosyl ester)
(Pulsatilla
chinensis)Baekduong
( Pulsatilla
chinensis )
(3-O-α-L-람노피라노실(1→2)-β-D-글루코피라노실(1→4)-α-L-아라비노피라노실 올레아놀산-28-O-α-L-람노피라노실(1→4)-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르)Hedera colchiside E
(3-O-α-L-lamnopyranosyl (1 → 2) -β-D-glucopyranosyl (1 → 4) -α-L-arabinopyranosyl oleanoic acid-28-O-α-L-rhamno Pyranosyl (1 → 4) -β-D-glucopyranosyl (1 → 6) -β-D-glucopyranosyl ester)
(Pulsatilla
chinensis)Baekduong
( Pulsatilla
chinensis )
(3-O-β-D-자이로피라노실(1→2)-β-D-갈락토피라노실(1→3)-β-D-글루쿠로노피라노실 올레아놀산)Elatoside A
(3-O-β-D-gyropyranosyl (1 → 2) -β-D-galactopyranosyl (1 → 3) -β-D-glucuronopyranosyl oleanoic acid)
(Aralia
elata)Neck
( Aralia
elata )
(3-O-β-D-자이로피라노실(1→2)-β-D-갈락토피라노실(1→3)-β-D-글루쿠로노피라노실 올레아놀산-28-O-β-D-글루코피라노실 에스테르)Elatoside C
(3-O-β-D-gyropyranosyl (1 → 2) -β-D-galactopyranosyl (1 → 3) -β-D-glucuronopyranosyl oleanoic acid-28-O-β- D-glucopyranosyl ester)
(Aralia
elata)Neck
( Aralia
elata )
((3-O-α-L-아라비노피라노실 헤데라게닌-28-O-α-L-람노피라노실(1→2)-β-D-자이로피라노실(1→6)-β-D-글루코피라노실 에스테르)Loniceroside A
((3-O-α-L-arabinopyranosyl hederagenin-28-O-α-L-rhamnopyranosyl (1 → 2) -β-D-gyropyranosyl (1 → 6) -β- D-glucopyranosyl ester)
(Lonicera
japonica)Lighting
( Lonicera
japonica )
(3-O-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 헤데라게닌-28-O-α-L-람노피라노실(1→2)-β-D-자이로피라노실(1→6)-β-D-글루코피라노실 에스테르)Loniceroside B
(3-O-α-L-rhamnopyranosyl (1 → 2) -α-L-arabinopyranosyl hederagenin-28-O-α-L-rhamnopyranosyl (1 → 2) -β-D Gyropyranosyl (1 → 6) -β-D-glucopyranosyl ester)
(Lonicera
japonica)Lighting
( Lonicera
japonica )
(Pericarpsaponin Pk, 3-O-α-L-람노피라노실(1→2)-α-L-아라비노피라노실 헤데라게닌-28-O-α-L-람노피라노실(1→4)-β-D-글루코피라노실(1→6)-β-D-글루코피라노실 에스테르)Kalopanaxsaponin B
(Pericarpsaponin Pk, 3-O-α-L-lamnopyranosyl (1 → 2) -α-L-arabinopyranosyl hederagenin-28-O-α-L-ramnopyranosyl (1 → 4)- β-D-glucopyranosyl (1 → 6) -β-D-glucopyranosyl ester)
(Kalopanax
pictus)Thawed blood
( Kalopanax
pictus )
실시예Example 3: 3: 트리테르펜Triterpenes 사포닌에 대한 수동회피 테스트( Manual avoidance test for saponins ( PassivePassive avoidanceavoidance testtest ))
상기한 8종의 올레아놀산 사포닌 또는 헤데라게닌 사포닌 성분이 생체 내에서 치매의 주요 증상인 기억력 증진에 효과가 있는지 알아보기 위하여 수동회피 테스트(Passive Avoidance Test)를 실시하였다. 또한 이들 사포닌 화합물의 아글리콘(aglycon)인 올레아놀산과 헤데라게닌도 실험에 포함하였다. A passive avoidance test was conducted to determine whether the eight oleanolic acid saponins or hederagenin saponins were effective in improving memory, a major symptom of dementia in vivo. The aglycons of these saponin compounds, oleanolic acid and hederagenin, were also included in the experiment.
실험장치는 가로, 세로, 높이가 50, 15, 40 cm인 셔틀 박스(Shuttle box)를 이용하였다. 이 박스는 칸막이 문(guillotine door)을 이용하여 두개의 방으로 나뉘어져 있으며, 한쪽 방은 조명이 있어 밝은 방으로 만들고 나머지 한쪽 방은 검은 천으로 뒤덮여 어두운 방으로 만들어 두 방에서 조명의 효과를 달리할 수 있도록 하였다.The experimental apparatus used a shuttle box having a width, length, and height of 50, 15, and 40 cm. The box is divided into two rooms using a guillotine door, one of which is illuminated, which makes it a bright room, and the other is covered by a black cloth, making it a dark room. To make it possible.
우선, 밝은 방에 쥐를 넣고 조명을 켜며 칸막이문을 열어주면 쥐는 어두운 곳을 찾아 들어가는 본능에 따라 20초 이내에 어두운 방으로 들어가며, 쥐가 어두운 방으로 이동하자마자 칸막이 문은 닫히게 된다. 이런 식으로 쥐가 밝은 방에서 어두운 방으로 들어가기까지의 시간을 도달시간(latency time)으로 측정하게 되는데 모든 쥐들이 20초 내에 들어가도록 하는 훈련과정(training trial)을 실험 첫날에 실시하였다.First, if you put the mouse in a bright room, turn on the lights and open the partition door, the mouse will enter the dark room within 20 seconds according to the instinct to find a dark place, and the partition door will close as soon as the mouse moves to the dark room. In this way, the time required for the rats to enter the dark room from the light room is measured as the latency time, and a training trial was conducted on the first day of the experiment to make sure that all the mice fit within 20 seconds.
그 다음날 위의 훈련을 거친 쥐들을 다시 밝은 방에 넣고 조명을 켜서 어두운 방으로 들어가도록 한다. 이때 어두운 방의 바닥에 설치된 전기 망(electronic grid)을 통해 3초간 0.8 mA의 전기자극을 주면 쥐들은 발바닥에 쇼크를 받게 된다. The next day, put the above trained rats back in the bright room and turn them on in the dark room. At this point, an electric stimulus of 0.8 mA is applied for three seconds through an electronic grid installed on the floor of a dark room, causing the mice to be shocked at the soles of their feet.
이러한 인식시행(acquisition trial)을 하고 24시간이 지난 후에 다시 쥐들을 밝은 방에 넣어 조명을 켜고 어두운 방으로 유도하였을 때 정상적인 쥐들은 전날의 쇼크를 기억하고 어두운 방으로 들어가는 것을 망설이게 된다. 이때의 도달시간을 300초를 최대로 하여 다시 측정하였다. After 24 hours of this acquisition trial, rats were placed in a bright room, turned on, and led to a dark room. Normal rats remembered the shock of the previous day and hesitated to enter the dark room. The arrival time at this time was measured again with a maximum of 300 seconds.
상기 실험에서 스코폴라민 및 약물을 투여하지 않은 대조군(control)과 신경전달물질의 전달방해를 통해 기억력을 감퇴시킨다고 알려진 스코폴라민(1 mg/kg)을투여 후 한 시간 뒤에 상기의 사포닌(30 mg/kg)과 아글리콘(30 mg/kg), 양성 대조군으로 아리셉트(donepezil, 1 mg/kg), 음성 대조군으로 물만을 투여한 그룹의 기억력 증진효과를 수동회피 테스트의 체류시간(Rention time)으로 측정하였다.In the experiment, one hour after the administration of scopolamine and scopolamine (1 mg / kg), which is known to reduce memory through interference with neurotransmitters, the control group without scopolamine and drugs was administered. mg / kg), aglycone (30 mg / kg), aricept (donepezil, 1 mg / kg) as a positive control, water retention as a negative control group, memory retention effect of the passive avoidance test (Rention time) Measured by.
그 결과, 대조약물인 아리셉트를 경구 투여한 그룹은 음성대조군인 물을 투여한 그룹에 비해 체류시간(retention time)이 1.6배 증가하는 기억력 증진 효과를 보였으며, 본 발명에 따른 8종의 올레아놀산 사포닌 또는 헤데라게닌 사포닌 성분은 모두 아글리콘(aglycon)과 당의 구성에 따라 약간의 차이가 있지만 모두 음성 대조군에 비해 수동회피 테스트에서 체류시간(Retention Time)이 2.5 ∼ 3.0 배 증가하는 인지기능 향상 효과를 보였다.As a result, the oral administration of the control drug Aricept showed a 1.6-fold increase in retention time compared to the negative administration of the water-treated group, and eight oleanoic acid saponins according to the present invention. Or, all of the components of hederagenin saponin are slightly different depending on the composition of aglycon and sugar, but all of them have a cognitive improvement effect of 2.5 to 3.0 times longer retention time in the passive avoidance test compared to the negative control group. Seemed.
또한 이들 사포닌은 아글리콘(aglycon)인 올레아놀산(2.4 배)과 헤데라게닌(2.3 배)에 비해서도 높은 인지 기능 향상 효과를 보였다. [표 2, 도 1 참조]. These saponins also showed higher cognitive function than aglycon oleanolic acid (2.4 times) and hederagenin (2.3 times). TABLE 2, see FIG. 1.
이러한 결과들로 보아 올레아놀산 사포닌과 헤데라게닌 사포닌은 치매 질환과 경도인지장애와 같은 증상에서 나타나는 감퇴된 기억력을 증진시켜주는 효과가 있으면 이 효과는 치매 치료제로 사용되고 있는 아리셉트는 물론 사포닌의 아글리콘(aglycon)인 올레아놀산과 헤데라게닌에 비해서도 우수함을 알 수 있었다.
These results suggest that oleanolic acid saponin and hederagenin saponin have the effect of improving the decreased memory in symptoms such as dementia disease and mild cognitive impairment. It was also found to be superior to oleanolic acid and hederagenin, which are aglycons.
다음의 제제예에서는 상기 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물을 유효 활성성분으로 포함하는 의약 또는 건강식품의 제조를 위한 일례로서, 본 발명이 이러한 제제 형태에 의해 국한되는 것은 결코 아니다.
In the following formulation example, as an example for the manufacture of a medicament or health food comprising the oleanane-based triterpene saponin compound represented by the formula (1) as an active ingredient, the present invention is not limited to this type of formulation.
제조예Manufacturing example 1: 분말 및 캅셀제의 제조 1: Preparation of Powder and Capsule
올레아난계 트리테르펜 사포닌 화합물 50 ㎎을 락토오스 74 ㎎, 결정성 셀룰로오스 15 ㎎, 마그네슘 스테아레이트 1 ㎎과 함께 섞어 분말제를 제조하였다. 또한, 이 분말을 적당한 장치를 사용하여 No.5 젤라틴 캅셀에 채워 캅셀제를 제조하였다.
A powder was prepared by mixing 50 mg of an oleonan-based triterpene saponin compound together with 74 mg of lactose, 15 mg of crystalline cellulose, and 1 mg of magnesium stearate. Furthermore, this powder was filled into No. 5 gelatin capsules using a suitable apparatus to prepare a capsule.
제조예Manufacturing example 2: 2: 액제의Liquid 제조 Produce
올레아난계 트리테르펜 사포닌 화합물 50 ㎎을 설탕 20 g, 이성화당 20 g, 레몬향 적량 가하고, 멸균 정제수를 가하여 전체 100 mL 용량으로 조절한 후, 갈색병에 충진하고 멸균시켜 액제를 제조하였다.
50 mg of oleanane-based triterpene saponin compound was added to 20 g of sugar, 20 g of isomerized sugar, and lemon flavor, and adjusted to a total volume of 100 mL by adding sterile purified water, and then filled into a brown bottle and sterilized to prepare a liquid.
제조예Manufacturing example 3: 건강식품의 제조 3: manufacture of health food
1일 복용 기준으로, 상기 화학식 1로 표시되는 올레아난계 트리테르펜 사포닌 화합물 100 mg, 인삼 추출물 100 mg, 녹차 추출물 100 mg, 비타민 C 100 mg, 분말비타민 E 120 mg, 젖산철 2 mg, 산화아연 2 mg, 니코틴산 아미드 20 mg, 비타민 A 5 mg, 비타민 B1 2 mg, 비타민 B2 2 mg, 옥수수전분 200 mg, 및 마그네슘 스테아레이트 20 mg을 혼합하여 제조하였다.
On a daily basis, 100 mg of oleanane-based triterpene saponin compounds represented by Formula 1,
Claims (2)
[화학식 1]
상기 화학식 1에서, R1, R2 및 R3는 각각 수소원자 또는 C1-C4의 알킬기를 나타내고, R4는 C1-C4의 알킬기 또는 C1-C4의 하이드록시알킬기를 나타내고, R5 및 R6는 각각 수소원자 또는 당(sugar)이고, R5 및 R6 둘 중의 적어도 하나 이상은 당(sugar)을 나타내고, 이때 당(sugar)은 글루코스, 갈락토스, 람노스, 자이로스, 아라비노스, 및 글루쿠론산 중에서 선택된다.
Health food having an effect of improving brain function containing oleanic triterpene saponin compound represented by the following formula (1):
[Formula 1]
In Formula 1, R 1 , R 2 and R 3 each represent a hydrogen atom or an alkyl group of C 1 -C 4 , and R 4 represents an alkyl group of C 1 -C 4 or a hydroxyalkyl group of C 1 -C 4 . , R 5 And R 6 are each hydrogen or sugar, R 5 And at least one of R 6 represents sugar, wherein the sugar is selected from glucose, galactose, rhamnose, gyros, arabinose, and glucuronic acid.
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