Daurisoline is a natural product isolated from the roots of Aconitum species, a genus of flowering plants belonging to the buttercup family Ranunculaceae. It exhibits a wide range of pharmacological activities, including anti-inflammatory, analgesic, and anticancer effects. Daurisoline has been shown to inhibit the production of pro-inflammatory cytokines like TNF-α and IL-6. It also possesses analgesic properties, potentially by modulating the activity of pain receptors. Furthermore, daurisoline has been found to exhibit cytotoxic effects against various cancer cell lines, suggesting its potential as a therapeutic agent for cancer treatment. The complex structure of daurisoline, featuring a unique ring system and multiple chiral centers, makes it a challenging target for total synthesis. However, several synthetic routes have been developed, allowing for the preparation of daurisoline and its analogs for further biological studies. The research on daurisoline aims to understand its mechanisms of action, explore its therapeutic potential, and develop synthetic methods for its production and modification. The unique chemical structure and diverse biological activities of daurisoline make it an intriguing target for pharmaceutical research.'
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daurisoline: antiarrhythmic from Menispermun dahuricum; structure in first source
ID Source | ID |
---|---|
PubMed CID | 51106 |
CHEMBL ID | 2216904 |
CHEBI ID | 184038 |
SCHEMBL ID | 24212114 |
MeSH ID | M0081808 |
Synonym |
---|
7-isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxy-3-(4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenoxy)phenyl)methyl)-6-methoxy-2-methyl-, (r-(r*,r*))- |
o(sup 7)-demethyldauricine |
(r-(r*,r*))-1,2,3,4-tetrahydro-1-((4-hydroxy-3-(4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenoxy)phenyl)methyl)-6-methoxy-2-methyl-7-isoquinolinol |
daurisoline |
d 610 |
(1r)-1-[[3-[4-[[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl]phenoxy]-4-hydroxyphenyl]methyl]-6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol |
CHEBI:184038 |
70553-76-3 |
S9150 |
CHEMBL2216904 , |
daruisoline |
bdbm50403104 |
AKOS015897168 |
DTXSID40220841 |
AC-34009 |
Q-100785 |
(r,r)-daurisoline |
CS-8095 |
HY-N0221 |
mfcd00221740 |
NCGC00482986-03 |
CCG-270233 |
AS-77876 |
SCHEMBL24212114 |
Daurisoline (DAS) is a component of traditional Chinese herb, Menispermum dauricum. It exhibits anti-cancer effects by autophagy inhibition and metastasis suppression.
Excerpt | Reference | Relevance |
---|---|---|
"Daurisoline (1) is a bis-benzylisoquinoline alkaloid isolated from the rhizomes of Menispermum dauricum. " | ( Effect of daurisoline on HERG channel electrophysiological function and protein expression. Jin, S; Liu, Q; Mao, X; Yang, X; Zeng, F, 2012) | 2.22 |
"Daurisoline (DAS) is a component of traditional Chinese herb, which exhibits anti-cancer effects by autophagy inhibition and metastasis suppression." | ( Daurisoline Inhibits ESCC by Inducing G1 Cell Cycle Arrest and Activating ER Stress to Trigger Noxa-Dependent Intrinsic and CHOP-DR5-Dependent Extrinsic Apoptosis via p-eIF2 Chen, X; Jia, L; Liu, Q; Pan, Y; Wang, F; Xu, T; Yuan, S; Zhang, L, 2022) | 2.89 |
"Daurisoline (DAS) is a constituent of Rhizoma Menispermi, and functions as a potential autophagy inhibitor to perform different cellular events." | ( Daurisoline inhibits hepatocellular carcinoma progression by restraining autophagy and promoting cispaltin-induced cell death. Liu, P; Xue, L, 2021) | 2.79 |
Excerpt | Reference | Relevance |
---|---|---|
" The pharmacokinetic and PK-PD model parameters were calculated." | ( Pharmacokinetic-pharmacodynamic modeling of daurisoline and dauricine in beagle dogs. Chen, H; Gu, SF; Shi, SJ; Zeng, FD, 2003) | 0.58 |
"To establish an HPLC method for the determination of daurisoline (DS) in rabbit plasma and investigate its pharmacokinetic characteristics after intravenous administration." | ( [Determination of daurisoline in rabbit plasma and study on its pharmacokinetics]. Chen, H; Gu, SF; Shi, SJ, 2003) | 0.9 |
"A sensitive, precise and accurate method for the determination of DS in plasma was described, which can be used in its pharmacokinetic studies." | ( [Determination of daurisoline in rabbit plasma and study on its pharmacokinetics]. Chen, H; Gu, SF; Shi, SJ, 2003) | 0.65 |
Class | Description |
---|---|
isoquinolines | A class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Potassium voltage-gated channel subfamily H member 2 | Homo sapiens (human) | IC50 (µMol) | 9.3500 | 0.0009 | 1.9014 | 10.0000 | AID719975; AID719980 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
plasma membrane | Potassium voltage-gated channel subfamily H member 2 | Homo sapiens (human) |
cell surface | Potassium voltage-gated channel subfamily H member 2 | Homo sapiens (human) |
perinuclear region of cytoplasm | Potassium voltage-gated channel subfamily H member 2 | Homo sapiens (human) |
voltage-gated potassium channel complex | Potassium voltage-gated channel subfamily H member 2 | Homo sapiens (human) |
inward rectifier potassium channel complex | Potassium voltage-gated channel subfamily H member 2 | Homo sapiens (human) |
plasma membrane | Potassium voltage-gated channel subfamily H member 2 | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID719986 | Inhibition of human ERG tail current expressed in HEK293 cells assessed as change in onset of inactivation curve between - 50 mV and + 10 mV holding potential at 10 uM by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719999 | Cmax in dog at 30 uM, iv administered as bolus dose | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719977 | Inhibition of human ERG tail current expressed in HEK293 cells at 3 uM at + 60 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1769496 | Antiproliferative activity against human HCC1806 assessed as cell growth inhibition after 48 hrs by SRB assay | |||
AID719988 | Inhibition of human ERG tail current expressed in HEK293 cells at - 80 mV to + 0 mV holding potential at 10 uM by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719984 | Inhibition of human ERG tail current expressed in HEK293 cells assessed as half activation potential for steady state inactivation curve at 10 uM by patch clamp assay (Rvb = - 48.7 +/- 7.6 mV) | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1769495 | Antiproliferative activity against human SJRH30 assessed as cell growth inhibition after 48 hrs by SRB assay | |||
AID719997 | Reduction in human ERG-tail density expressed in HEK293 cells at 30 uM after 24 hrs by densitometric analysis | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719969 | Inhibition of Iks tail current in rabbit ventricular myocytes | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719979 | Inhibition of human ERG tail current expressed in HEK293 cells at 30 uM at + 60 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1769492 | Antiproliferative activity against human MDA-MB-453 assessed as cell growth inhibition after 48 hrs by SRB assay | |||
AID719995 | Downregulation of human ERG expression in HEK293 cells assessed as decrease in intensity of 155 kDa band at 30 uM after 24 hrs by Western blot analysis | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719980 | Inhibition of human ERG tail current expressed in HEK293 cells at + 60 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719975 | Inhibition of human ERG stepped current expressed in HEK293 cells at + 20 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719970 | Inhibition of human ERG tail current expressed in HEK293 cells at 30 uM within 2 mins by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID720000 | Inhibition of human ERG at 1.7 uM | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719981 | Inhibition of human ERG tail current expressed in HEK293 cells assessed as half activation potential for steady state activation curve at 10 uM by patch clamp assay (Rvb = 2.8 +/- 3.3 mV) | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1769497 | Antiproliferative activity against human HCC70 assessed as cell growth inhibition after 48 hrs by SRB assay | |||
AID719996 | Downregulation of human ERG expression in HEK293 cells assessed as decrease in intensity of 135 kDa band at 30 uM after 24 hrs by Western blot analysis | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719978 | Inhibition of human ERG tail current expressed in HEK293 cells at 10 uM at + 60 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719994 | Downregulation of human ERG expression in HEK293 cells assessed as change in intensity of 135 kDa band at 1 to 10 uM after 24 hrs by Western blot analysis | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719991 | Downregulation of human ERG mRNA expression in HEK293 cells at 30 uM after 24 hrs by RT-PCR analysis | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719983 | Inhibition of human ERG tail current expressed in HEK293 cells at 10 uM at - 120 to + 20 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1769493 | Antiproliferative activity against human MDA-MB-231 assessed as cell growth inhibition after 48 hrs by SRB assay | |||
AID719973 | Inhibition of human ERG stepped current expressed in HEK293 cells at 10 uM at + 20 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719992 | Downregulation of human ERG mRNA expression in HEK293 cells at 30 uM after 24 hrs by qRT-PCR analysis | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1769494 | Antiproliferative activity against human A673 assessed as cell growth inhibition after 48 hrs by SRB assay | |||
AID719989 | Inhibition of human ERG tail current expressed in HEK293 cells assessed as time constant at + 30 mV holding potential at 10 uM by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719990 | Inhibition of human ERG tail current expressed in HEK293 cells at 50 ms by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1769489 | Antiproliferative activity against human HCC1937 assessed as cell growth inhibition after 48 hrs by SRB assay | |||
AID719993 | Downregulation of human ERG expression in HEK293 cells assessed as change in intensity of 155 kDa band at 1 to 10 uM after 24 hrs by Western blot analysis | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719976 | Inhibition of human ERG tail current expressed in HEK293 cells at 1 uM at + 60 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719982 | Inhibition of human ERG tail current expressed in HEK293 cells at 10 uM at + 40 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719968 | Inhibition of Ikr tail current in rabbit ventricular myocytes | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719967 | Inhibition of Ikr tail current in guinea pig ventricular myocytes at 10 uM | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719972 | Inhibition of human ERG stepped current expressed in HEK293 cells at 3 uM at + 20 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719974 | Inhibition of human ERG stepped current expressed in HEK293 cells at 30 uM at + 20 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719998 | Cmax in rabbit at 30 uM, iv administered as bolus dose | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719971 | Inhibition of human ERG stepped current expressed in HEK293 cells at 1 uM at + 20 mV holding potential by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719985 | Inhibition of human ERG tail current expressed in HEK293 cells assessed as increase in steady state inactivation time constant from - 120 mV to - 60 mV holding potential at 10 uM by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719987 | Inhibition of human ERG tail current expressed in HEK293 cells assessed as decrease in time constant for the onset of inactivation curve at - 20 mV holding potential at 10 uM by patch clamp assay | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID719966 | Inhibition of Iks tail current in guinea pig ventricular myocytes at 100 uM | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID720001 | Inhibition of rabbit ERG channel assessed as decrease in monophasic action potential duration | 2012 | Journal of natural products, Sep-28, Volume: 75, Issue:9 | Effect of daurisoline on HERG channel electrophysiological function and protein expression. |
AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | 2014 | Journal of biomolecular screening, Jul, Volume: 19, Issue:6 | A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. |
AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | |||
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 17 (48.57) | 18.2507 |
2000's | 6 (17.14) | 29.6817 |
2010's | 4 (11.43) | 24.3611 |
2020's | 8 (22.86) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (20.43) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 35 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |