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.[H][C@]12CC3=CC(O)=C(OC)C=C3C4=C1C(CCN2C)=CC(O)=C4OC
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 |
|---|---|---|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| Antipoliovirus structure-activity relationships of some aporphine alkaloids. | 1998 Apr |
|
| Halogenated boldine derivatives with enhanced monoamine receptor selectivity. | 2000 Apr |
|
| Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products. | 2001 Feb |
|
| Chemoprotective activity of boldine: modulation of drug-metabolizing enzymes. | 2001 Mar |
|
| Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity. | 2002 Feb 22 |
|
| Effects of some antioxidative aporphine derivatives on striatal dopaminergic transmission and on MPTP-induced striatal dopamine depletion in B6CBA mice. | 2003 Feb |
|
| Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora. | 2003 Jun |
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| Spectroscopic study of antileishmanial drug incubated in the promastigotes of Leishmania mexicana. | 2003 Nov |
|
| 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 Apr |
|
| Reactive oxygen species (ROS) generation inhibited by aporphine and phenanthrene alkaloids semi-synthesized from natural boldine. | 2004 Jun |
|
| Inhibitory action of conventional food-grade natural antioxidants and of natural antioxidants of new development on the thermal-induced oxidation of cholesterol. | 2004 Mar |
|
| Protective role of Scoparia dulcis plant extract on brain antioxidant status and lipidperoxidation in STZ diabetic male Wistar rats. | 2004 Nov 2 |
|
| Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine. | 2005 Jan-Feb |
|
| Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity. | 2005 Jun 1 |
|
| [Alkaloids from the root of Lindera angustifolia]. | 2005 Oct |
|
| 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 |
|
| Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method. | 2006 Jun |
|
| Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction. | 2006 Oct |
|
| Advances in development of dopaminergic aporphinoids. | 2007 Jan 25 |
|
| Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers. | 2007 May 15 |
|
| The hunt for natural skin whitening agents. | 2009 Dec 10 |
|
| Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis. | 2009 Mar 23 |
|
| Ascorbic acid and tetrahydrobiopterin potentiate the EDHF phenomenon by generating hydrogen peroxide. | 2009 Nov 1 |
|
| Anti-photoaging and photoprotective compounds derived from marine organisms. | 2010 Apr 8 |
|
| 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 |
|
| Cytotoxic thiocarbamate derivatives of boldine. | 2010 Oct |
|
| Boldine, a natural aporphine alkaloid, inhibits telomerase at non-toxic concentrations. | 2015 Apr 25 |
|
| 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.
| 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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