Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H21NO4.ClH |
| Molecular Weight | 363.835 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=C(O)C=C2C[C@@H]3N(C)CCC4=CC(O)=C(OC)C(C2=C1)=C34
InChI
InChIKey=MUGNKMCHLPQCMV-ZOWNYOTGSA-N
InChI=1S/C19H21NO4.ClH/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;1H/t13-;/m0./s1
| Molecular Formula | C19H21NO4 |
| Molecular Weight | 327.3743 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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) |
|||
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 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Boldine enhances bile production in rats via osmotic and farnesoid X receptor dependent mechanisms. | 2015-05-15 |
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| Boldine, a natural aporphine alkaloid, inhibits telomerase at non-toxic concentrations. | 2015-04-25 |
|
| 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. | 2010-12-15 |
|
| Cytotoxic thiocarbamate derivatives of boldine. | 2010-10 |
|
| Current and developing therapeutic agents in the treatment of Chagas disease. | 2010-09-24 |
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| Anti-photoaging and photoprotective compounds derived from marine organisms. | 2010-04-08 |
|
| 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. | 2010-01-22 |
|
| The hunt for natural skin whitening agents. | 2009-12-10 |
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| Boldine: a potential new antiproliferative drug against glioma cell lines. | 2009-12 |
|
| Ascorbic acid and tetrahydrobiopterin potentiate the EDHF phenomenon by generating hydrogen peroxide. | 2009-11-01 |
|
| The aporphine alkaloid boldine induces adiponectin expression and regulation in 3T3-L1 cells. | 2009-10 |
|
| Effect of boldo (Peumus boldus Molina) infusion on lipoperoxidation induced by cisplatin in mice liver. | 2009-07 |
|
| Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis. | 2009-03-23 |
|
| [Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography]. | 2009-03 |
|
| 5-Hydroxytryptamine2A receptor binding activity of compounds from Litsea sessilis. | 2009-03 |
|
| Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry. | 2008-11-28 |
|
| Antioxidant and pro-oxidant properties of boldine on hippocampal slices exposed to oxygen-glucose deprivation in vitro. | 2008-11 |
|
| Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers. | 2007-05-15 |
|
| Advances in development of dopaminergic aporphinoids. | 2007-01-25 |
|
| Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction. | 2006-10 |
|
| Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats. | 2006-10 |
|
| Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen. | 2006-07-19 |
|
| Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method. | 2006-06 |
|
| Boldine and its antioxidant or health-promoting properties. | 2006-01-05 |
|
| [Alkaloids from the root of Lindera angustifolia]. | 2005-10 |
|
| 8-NH2-boldine, an antagonist of alpha1A and alpha1B adrenoceptors without affinity for the alpha1D subtype: structural requirements for aporphines at alpha1-adrenoceptor subtypes. | 2005-10 |
|
| Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo. | 2005-09 |
|
| Photostability and photoprotection factor of boldine and glaucine. | 2005-07-01 |
|
| Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity. | 2005-06-01 |
|
| Protective role of Scoparia dulcis plant extract on brain antioxidant status and lipidperoxidation in STZ diabetic male Wistar rats. | 2004-11-02 |
|
| Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine. | 2004-10-21 |
|
| Reactive oxygen species (ROS) generation inhibited by aporphine and phenanthrene alkaloids semi-synthesized from natural boldine. | 2004-06 |
|
| Alkaloids from Cassytha filiformis and related aporphines: antitrypanosomal activity, cytotoxicity, and interaction with DNA and topoisomerases. | 2004-05 |
|
| A novel alkaloid antioxidant, Boldine and synthetic antioxidant, reduced form of RU486, inhibit the oxidation of LDL in-vitro and atherosclerosis in vivo in LDLR(-/-) mice. | 2004-04 |
|
| Inhibitory action of conventional food-grade natural antioxidants and of natural antioxidants of new development on the thermal-induced oxidation of cholesterol. | 2004-03 |
|
| Spectroscopic study of antileishmanial drug incubated in the promastigotes of Leishmania mexicana. | 2003-11 |
|
| Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora. | 2003-06 |
|
| Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo"). | 2003-04 |
|
| Effects of some antioxidative aporphine derivatives on striatal dopaminergic transmission and on MPTP-induced striatal dopamine depletion in B6CBA mice. | 2003-02 |
|
| Protection against UVB irradiation by natural filters extracted from lichens. | 2002-11 |
|
| Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity. | 2002-02-22 |
|
| Protective effect of boldine on dopamine-induced membrane permeability transition in brain mitochondria and viability loss in PC12 cells. | 2002-02-01 |
|
| Chemoprotective activity of boldine: modulation of drug-metabolizing enzymes. | 2001-03 |
|
| Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products. | 2001-02 |
|
| Halogenated boldine derivatives with enhanced monoamine receptor selectivity. | 2000-04 |
|
| Antipoliovirus structure-activity relationships of some aporphine alkaloids. | 1998-04 |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991-01-01 |
|
| Screening for new compounds with antiherpes activity. | 1984-10 |
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.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
G6R77KSG8R
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| Record Status |
Validated (UNII)
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| Record Version |
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