| Identification | Back Directory | [Name]
DAURICINE | [CAS]
524-17-4 | [Synonyms]
Dauricine
(r-(r*,r*))-y)
dauricine (8ci)
6,6'-Di-O-Methyldauricoline
Menispermum dauricum DC Extract
-(4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenox
4-[[(1R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-2-[4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenoxy]phenol
4-[((1R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl)methyl]-2-[4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenoxy]phenol | [Molecular Formula]
C38H44N2O6 | [MDL Number]
MFCD26960929 | [MOL File]
524-17-4.mol | [Molecular Weight]
624.774 |
| Chemical Properties | Back Directory | [Melting point ]
115° | [alpha ]
D11 -139° in methanol | [Boiling point ]
712.3±60.0 °C(Predicted) | [density ]
1.185±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
9.31±0.45(Predicted) | [color ]
Pale Beige | [Water Solubility ]
slightly soluble in water | [InChIKey]
AQASRZOCERRGBL-ROJLCIKYSA-N | [SMILES]
C1(O)=CC=C(C[C@@H]2C3=C(C=C(OC)C(OC)=C3)CCN2C)C=C1OC1=CC=C(C[C@@H]2C3=C(C=C(OC)C(OC)=C3)CCN2C)C=C1 | [CAS DataBase Reference]
524-17-4 |
| Hazard Information | Back Directory | [Definition]
ChEBI: A bisbenzylisoquinoline alkaloid resulting from the formal oxidative dimerisation of 4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenol by attachment of the phenolic oxygen of one molecule to the benzene ring
f the second (ortho to the phenolic hydroxy group of the latter). | [Physical properties]
Appearance: yellowish-white powder or crystal. Solubility: soluble in ethanol,
methanol, chloroform, acetone, benzene and slightly soluble in ether. Density:
1.185 g/cm3. Melting point: 115 °C. Boiling point: 712.3 °C at 760 mmHg atmospheric
pressure. Specific optical rotation: MeOH-139.
| [History]
Menispermum dauricum has been long used as a traditional Chinese medicine, but
the research of its effective components has been slow. Dauricine was firstly separated
and structure-confirmed by Fukuda Mayo using alumina column chromatography
separation assay in 1964. At the same year, dauricine was first synthesized
by two Japanese scientists, Tetsuji Tamayama and Rtani Rikazu, by means of Arndt-Eistert
reaction and Bischler-Napieralski reaction. Thereafter, lots of scientists
from various countries successively separated daurinoline, Menispermum Xinlin
alkali, Menispermum succinylcholine alkali, chelilanthifoline, stepholidine, and
many other monomeric components of Menispermum dauricum.
The study of dauricine in China started from the Cultural Revolution Period.
Under the guidance of integrated traditional Chinese and Western medicine, a large
number of effective components in traditional Chinese herbs were extracted, separated
and applied to clinic. Dauricine was firstly reported on the mainland as an
active ingredient in herbs which can clear away heat and toxic materials. Moreover,
dauricine was also used as an antineoplastic and muscle relaxant. There were many
medicines whose principal component was dauricine had been under clinical
research for its role of cardiovascular protection since the 1980s, most of these
medicines were stagnating in phase II clinical trials.
| [Uses]
Dauricine is a bisbenzylisoquinoline allkaloid derivative that displays a noted number of pharmaceutical properties. It is known to induces severe lung toxicity in animals. | [Indications]
Drugs whose main component is dauricine are still in clinical trials. Several formulations of dauricine have currently been developed, including tablets, capsules,
injections, and so on. The main indications of dauricine in clinical trials are antiplatelet,antihypertensive and anti-arrhythmic.
| [Pharmacology]
The main pharmacological actions of dauricine are as follows;
Anti-arrhythmia: Dauricine can slow the heart rate and prolong conduction time in
sinus rhythm, therefore reducing the incidence of arrhythmia.
Anti-myocardial ischemia: Dauricine has protective effect on myocardial ischemia
and can improve hemodynamic disturbances during ischemia which is supposed
to produce effect via mechanism of improving myocardial metabolism and
anti-oxidation.
Anti-cerebral ischemia: Dauricine has an effective regulation on gene expression of
Bcl-2 and Bax in cortical neurons after the ischemic brain injury, protecting
against cerebral ischemia.
Anti-cerebral ischemia/reperfusion injury: Dauricine can inhibit apoptosis induced
by cerebral ischemia/reperfusion injury by upregulating Bcl-2 expression and
downregulating Bax expression. Also dauricine has the effect of anti-oxidation.
Antitumor activity: Dauricine can affect TGF-beta signaling pathway via upregulating
gene expression of DPC4, and then the gene expression of P53 and P16 in
tumor tissue, and finally reduce the gene expression of hFGF in tumor tissue.
Thereby, the growth of various tumor cells could be inhibited.
The investigations of metabolism in vivo of dauricine indicate that it is rapidly
and widely distributed in body and the drug concentration in organs is significantly
higher than that in plasma, and this is possibly related to its strong lipid solubility
and easy access to cells.
| [Clinical Use]
No medicine in the market takes dauricine as the main component up till now. Many
animal experiments and clinical studies suggest that dauricine can reverse the effect
of MDR as verapamil. Since the clinical application of the classical drug verapamil
is limited for the serious toxic side effects, the moderate pharmacological effect of
dauricine has a vital clinical significance. The main side effect of dauricine by oral
absorption is gastrointestinal reaction, such as diarrhea, nausea, abdominal distension,
and so on. In addition, dauricine can accumulate in the body, leading to hepatorenal
toxicity and central nervous system toxicity. | [storage]
4°C, protect from light |
| Questions And Answer | Back Directory | [Description]
As a plant metabolite, Dauricine is a bioactive component derived from Asiatic Moonseed Rhizome and Canadian moonseed, which has been widely used in the treatment of a variety of inflammatory diseases especially in traditional Chinese medicine. It was first synthesized by the scientists from Japan in 1964.
It has been proved that Dauricine plays a number of biological roles in the human body, from inhibiting cancer cell growth to blocking cardiac transmembrane Na+, K+, and Ca2+ ion currents. Recent studies suggested that there is novel role of dauricine in preventing or treating cancer. It has been shown to have anti-tumor effects in several cancers, including colon cancer, breast cancer, urinary cancers such as bladder cancer and prostate cancer.
| [References]
https://en.wikipedia.org/wiki/Dauricine
https://www.ncbi.nlm.nih.gov/pubmed/20509140
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