기본 정보
- 표준 SMILES
COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2- InChIKey
YBHILYKTIRIUTE-UHFFFAOYSA-N- 분자식
- C20H18NO4+
- 평균 분자량
- 336.4 g/mol
- 단동위원소 질량
- 336.12303448
개요
Berberine is a berberine alkaloid, an organic heteropentacyclic compound, an alkaloid antibiotic and a botanical anti-fungal agent. It has a role as a geroprotector, an antioxidant, a metabolite, a hypoglycemic agent, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an antineoplastic agent, an antilipemic drug, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, a potassium channel blocker, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor and an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor.
이름 및 식별자
- 우선 이름
- Berberine
- IUPAC
- 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene
- 영어명
- Berberine
- 분자식
- C20H18NO4
- 분자량
- 336.36
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
2086-83-1- PubChem CID
- 2353
- DTXSID
DTXSID9043857- ChEMBL
CHEMBL295124- ChEBI
CHEBI:16118- UNII
- 0I8Y3P32UF
- EC Number
- 218-229-1
- Nikkaji
- J7.320B
물성
구조 계산 물성
- XLogP
- 3.6
- 극성 표면적
- 40.8 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 25
- 형식 전하
- 1
- 복잡도
- 488
실험 및 물리화학적 성질
Physical Description
Yellow solid; [Merck Index]
Solid
물리화학적 성질
- 녹는점
- 204 · 204-206 °C (dec.)
- 끓는 점
- 486.8 °C · 486.8°C (rough estimate)
- 밀도
- 1.2976 · 1.2976 (rough estimate)
- 굴절률
- 1.58 · 1.5800 (estimate)
- 저장 조건
- Inert atmosphere,Room Temperature
- 용해도
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 2.47 · 2.47(at 25℃)
- 색상
- 흰색에서 노란색 결정
- 수용성
- 43.48 g/L · 43.48g/L(25℃)
- InChI
- InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
- InChIKey
- YBHILYKTIRIUTE-UHFFFAOYSA-N
- SMILES
- O(C1C(=CC=C2C=1C=[N+]1CCC3=CC4OCOC=4C=C3C1=C2)OC)C
- LogP
- -0.99 · -0.990 (est)
화학적 성질
White to yellow crystals. Iinsoluble in water; soluble in ether, alcohol. Salts of berberine are berberine bisulfate, berberine sulfate, and berberine hydrochloride. All three are yellow crystals, slightly soluble in water.
안전 및 규제
유해성 정보
독성 정보
Hepatotoxicity
Berberine has not been linked to serum enzyme elevations during therapy, although there have been few prospective studies in humans that have reported on its effects on laboratory test results in any detail. In published trials, berberine has appeared to be well tolerated with only minor and few adverse effects which have been similar in frequency among persons receiving placebo. Despite wide scale use as an herbal supplement, berberine has not been linked to published instances of clinically apparent liver injury. The frequency of hypersensitivity reactions to berberine is also not known.
Toxicity Summary
Sanguinarine [13-methyl (1,3) benzodioxolo(5,6-c)-1,3-dioxolo (4,5) phenanthridinium] kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Berberine, on the other hand, has been reported to cause cytotoxicity and adversely influence the synthesis of DNA. Studies have reported various pharmacological properties of these alkaloids, e.g., they exhibit antibacterial, antiasthma, anticancer, anti-inflammatory, and antidiabetic activities.
안전 데이터
- wgk
- 2
- rtecs
- DR9866400
- ridadr
- 1544
- 독성
- LD50 orl-mus: 329 mg/kg YKKZAJ 82,726,62
- 포장분류
- III
- 위험 등급
- 6.1(b)
- F 고인화성물질
- 3-10
화학 및 산업
약리 정보
Mechanism of Action
This publication noted that berberine is an alkaloid from Hydrastis canadensis L., Chinese herb Huanglian, and many other plants. It is widely used in traditional Chinese medicine as an antimicrobial in the treatment of dysentery and infectious diarrhea. The authors describe the cardiovascular effects of berberine and its derivatives, tetrahydroberberine and 8-oxoberberine, e.g., berberine has positive inotropic, negative chronotropic, antiarrhythmic, and vasodilator properties. Some cardiovascular effects of berberine and its derivatives are attributed to the blockade of K+ channels (delayed rectifier and K(ATP)) and stimulation of Na+ -Ca(2+) exchanger. Also, berberine prolongs the duration of ventricular action potential. Its vasodilator activity has been attributed to multiple cellular mechanisms. The authors note that the cardiovascular effects of berberine suggest its possible clinical usefulness in the treatment of arrhythmias and/or heart failure.
Berberine, an isoquinoline alkaloid isolated from the Chinese herb Coptis chinensis and other Berberis plants, has a wide range of pharmacological properties. This publication notes the mechanisms of berberine's functions have been extensively explored, and that berberine: 1) can be used to treat many diseases, such as cancer and digestive, metabolic, cardiovascular, and neurological diseases, 2) has protective capacities in digestive diseases, 3) can inhibit toxins and bacteria, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury, 4) inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis, 5) improves the efficacy and safety of chemoradiotherapies, 6) regulates glycometabolism and lipid metabolism, improves energy expenditure, reduces body weight, and alleviates nonalcoholic fatty liver disease, 7) improves cardiovascular hemodynamics, suppresses ischemic arrhythmias, attenuates the development of atherosclerosis, and reduces hypertension, 8) shows potent neuroprotective effects, including antioxidative, antiapoptotic, and anti-ischemic, and 9) exerts protective effects against other diseases.
용도 및 제조
응용 분야
개요Coptis chinensis was widely used in China as a folk medicine by Shennong around 3000 BC. Coptis chinensis was first described in the ancient Chinese medical book The Divine Farmer's Herb-Root Classic. Coptis chinensis was used to treat intestinal bacterial infections and antipyretic analgesic for thousands of years agoCoptis chinensis also called zhilian, chuanlian, weilian, jizhualian, shanglian, and xuanlian in Chinese history. Coptis chinensis was accepted by most physicians, and the Chinese pharmacopoeia also uses Coptis chinensis as its official name. Coptis chinensis mainly grows in Anhui, Hunan, Sichuan, and Yunnan and has been cultivated in Sichuan since the Ming dynasty, which has a long history of cultivation. Other species of Coptis chinensis from different places were used as medicine. However, commodity circulation of wild Rhizoma coptidis has not been formed . Coptis chinensis is national three level protection plants at present and majorly produced in Shizhu of Chongqing, West Hubei, Shanxi, and Gansu.Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in some plants such as huanglian (Rhizoma coptidis), huangbo (Phellodendri Chinensis) Cortex), sankezhenthree needles (Berberidis Radix), and so on.The components of Coptis chinensis which have antibacterial and antiinflammatory effects are original alkaloid berberine class, including berberine, coptisine, palmatine, epiberberine, columbamine, jatrorrhizine, worenine, and magnoflorine, with berberine having the highest content (5–8%).
역사Berberine is often used in the form of quaternary ammonium alkali. The solubility of berberine in water is lower, for example, berberine hydrochloride is 1:500, and berberine sulfate is 1:30. In 1926, berberine was first separated from bark of Zanthoxylum clava. Modern pharmacology study showed that berberine has defined structure and is a monomer of traditional Chinese medicine. Berberine can be obtained from many sources and is used in clinics, with reliable pharmacological effects and various and unique mechanisms. At present, berberine can be synthesized by industrial biosynthesis. A series of derivatives can also be synthesized by structure modification, and the pharmacological activities of these derivatives have been tested.
용도Antiseptic drug.Treat intestinal infection caused from dysentery bacillus and E.coil
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