Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H21NO4 |
| Molecular Weight | 327.3743 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CC3=CC(O)=C(OC)C=C3C4=C1C(CCN2C)=CC(O)=C4OC
InChI
InChIKey=LZJRNLRASBVRRX-ZDUSSCGKSA-N
InChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1
Boldine, an aporphine alkaloid, found abundantly in the leaves/bark of boldo (Peumus boldus Molina) widely consumed in the folk medicine of some regions. Boldine possesses various pharmacological properties including, anticancer activity. It exhibits a significant improvement of learning and memory through inhibition of brain acetylcholinesterase activity and alleviation of brain oxidative stress, which was shown on animal models. Boldine is a potentially useful agent for the treatment of leishmaniosis. In addition, it suppresses osteoclastogenesis, improves bone destruction and may be a potential therapeutic agent for rheumatoid arthritis. Besides, was shown, that boldine inhibits telomerase in cells treated with sub-cytotoxic concentrations. Telomerase inhibition occurs via down-regulation of human telomerase reverse transcriptase (hTERT), the catalytic subunit of the enzyme.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P22303|||Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) |
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Target ID: O14746 Gene ID: 7015.0 Gene Symbol: TERT Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
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| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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| Antipoliovirus structure-activity relationships of some aporphine alkaloids. | 1998 Apr |
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| Halogenated boldine derivatives with enhanced monoamine receptor selectivity. | 2000 Apr |
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| Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity. | 2002 Feb 22 |
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| Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo"). | 2003 Apr |
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| Reactive oxygen species (ROS) generation inhibited by aporphine and phenanthrene alkaloids semi-synthesized from natural boldine. | 2004 Jun |
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| Alkaloids from Cassytha filiformis and related aporphines: antitrypanosomal activity, cytotoxicity, and interaction with DNA and topoisomerases. | 2004 May |
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| Protective role of Scoparia dulcis plant extract on brain antioxidant status and lipidperoxidation in STZ diabetic male Wistar rats. | 2004 Nov 2 |
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| Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine. | 2005 Jan-Feb |
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| Photostability and photoprotection factor of boldine and glaucine. | 2005 Jul 1 |
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| Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity. | 2005 Jun 1 |
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| [Alkaloids from the root of Lindera angustifolia]. | 2005 Oct |
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| 8-NH2-boldine, an antagonist of alpha1A and alpha1B adrenoceptors without affinity for the alpha1D subtype: structural requirements for aporphines at alpha1-adrenoceptor subtypes. | 2005 Oct |
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| Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo. | 2005 Sep |
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| Boldine and its antioxidant or health-promoting properties. | 2006 Jan 5 |
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| Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen. | 2006 Jul 19 |
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| Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method. | 2006 Jun |
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| Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction. | 2006 Oct |
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| Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats. | 2006 Oct |
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| Advances in development of dopaminergic aporphinoids. | 2007 Jan 25 |
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| Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers. | 2007 May 15 |
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| Antioxidant and pro-oxidant properties of boldine on hippocampal slices exposed to oxygen-glucose deprivation in vitro. | 2008 Nov |
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| Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry. | 2008 Nov 28 |
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| Boldine: a potential new antiproliferative drug against glioma cell lines. | 2009 Dec |
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| The hunt for natural skin whitening agents. | 2009 Dec 10 |
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| Effect of boldo (Peumus boldus Molina) infusion on lipoperoxidation induced by cisplatin in mice liver. | 2009 Jul |
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| [Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography]. | 2009 Mar |
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| 5-Hydroxytryptamine2A receptor binding activity of compounds from Litsea sessilis. | 2009 Mar |
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| Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis. | 2009 Mar 23 |
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| Ascorbic acid and tetrahydrobiopterin potentiate the EDHF phenomenon by generating hydrogen peroxide. | 2009 Nov 1 |
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| The aporphine alkaloid boldine induces adiponectin expression and regulation in 3T3-L1 cells. | 2009 Oct |
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| Anti-photoaging and photoprotective compounds derived from marine organisms. | 2010 Apr 8 |
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| Quantitative analysis of boldine alkaloid in natural extracts by cyclic voltammetry at a liquid-liquid interface and validation of the method by comparison with high performance liquid chromatography. | 2010 Dec 15 |
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| Direct identification of phenolic constituents in Boldo Folium (Peumus boldus Mol.) infusions by high-performance liquid chromatography with diode array detection and electrospray ionization tandem mass spectrometry. | 2010 Jan 22 |
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| Cytotoxic thiocarbamate derivatives of boldine. | 2010 Oct |
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| Current and developing therapeutic agents in the treatment of Chagas disease. | 2010 Sep 24 |
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| Boldine, a natural aporphine alkaloid, inhibits telomerase at non-toxic concentrations. | 2015 Apr 25 |
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| Boldine enhances bile production in rats via osmotic and farnesoid X receptor dependent mechanisms. | 2015 May 15 |
Sample Use Guides
in mice: boldine (1.5, 3 and 6mg/kg, po) for 7 successive days exhibited significant improvement of learning and memory of young and aged mice
anticonvulsant effects in mice: boldine (once in a day for 8 days, ip.)
in mice: repeated i. p. injections of 30, 60, or 90 mg boldine/kg slowed tumor growth
Route of Administration:
Other
It was shown that boldine is a potentially useful agent for the treatment of leishmaniasis. The in vitro system consisted of murine macrophage infection with amastigotes of L. amazonensis treated with different concentrations from 50 to 600 μg/ml of boldine for 24 hr. Intracellular parasite destruction was assessed by morphological examination and boldine cytotoxicity to macrophages was tested by the MTT viability assay. When cells were treated with 100 μg/ml of boldine the reduction of parasite infection was 81% compared with untreated cultures cells.
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EU-Orphan Drug |
EU/3/13/1226
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207-509-9
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SUB13107MIG
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BOLDINE
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m2598
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476-70-0
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C011686
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SUBSTANCE RECORD
