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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NO4
Molecular Weight 327.3751
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BOLDINE

SMILES

CN1CCc2cc(c(c3-c4cc(c(cc4C[C@@]1([H])c23)O)OC)OC)O

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

HIDE SMILES / InChI

Molecular Formula C19H21NO4
Molecular Weight 327.3751
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Protective effect of boldine on dopamine-induced membrane permeability transition in brain mitochondria and viability loss in PC12 cells.
2002 Feb 1
Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity.
2002 Feb 22
Protection against UVB irradiation by natural filters extracted from lichens.
2002 Nov
Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo").
2003 Apr
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
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
Alkaloids from Cassytha filiformis and related aporphines: antitrypanosomal activity, cytotoxicity, and interaction with DNA and topoisomerases.
2004 May
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
Photostability and photoprotection factor of boldine and glaucine.
2005 Jul 1
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
Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo.
2005 Sep
Boldine and its antioxidant or health-promoting properties.
2006 Jan 5
Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen.
2006 Jul 19
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
Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats.
2006 Oct
Advances in development of dopaminergic aporphinoids.
2007 Jan 25
Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers.
2007 May 15
Antioxidant and pro-oxidant properties of boldine on hippocampal slices exposed to oxygen-glucose deprivation in vitro.
2008 Nov
Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry.
2008 Nov 28
Boldine: a potential new antiproliferative drug against glioma cell lines.
2009 Dec
Effect of boldo (Peumus boldus Molina) infusion on lipoperoxidation induced by cisplatin in mice liver.
2009 Jul
[Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography].
2009 Mar
5-Hydroxytryptamine2A receptor binding activity of compounds from Litsea sessilis.
2009 Mar
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
The aporphine alkaloid boldine induces adiponectin expression and regulation in 3T3-L1 cells.
2009 Oct
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
by admin
on Fri Jun 25 21:08:09 UTC 2021
Edited
by admin
on Fri Jun 25 21:08:09 UTC 2021
Record UNII
8I91GE2769
Record Status Validated (UNII)
Record Version
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Name Type Language
BOLDINE
MI   WHO-DD  
Common Name English
(6AS)-5,6,6A,7-TETRAHYDRO-1,10-DIMETHOXY-6-METHYL-4H-DIBENZO(DE,G)QUINOLINE-2,9-DIOL
Common Name English
BOLDINE [WHO-DD]
Common Name English
BOLDINE [MI]
Common Name English
1,10-DIMETHOXY-2,9-DIHYDROXYAPORPHINE
Systematic Name English
1,10-DIMETHOXY-6A.ALPHA.-APORPHINE-2,9-DIOL
Common Name English
(S)-BOLDINE
Common Name English
2,6-DIHYDROXY-3,5-DIMETHOXYAPORPHINE
Common Name English
NSC-65689
Code English
BOLDINE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/13/1226
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
207-509-9
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY
EVMPD
SUB13107MIG
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY
PUBCHEM
10154
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY
FDA UNII
8I91GE2769
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY
WIKIPEDIA
BOLDINE
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY
MERCK INDEX
M2598
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY Merck Index
CAS
476-70-0
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY
MESH
C011686
Created by admin on Fri Jun 25 21:08:09 UTC 2021 , Edited by admin on Fri Jun 25 21:08:09 UTC 2021
PRIMARY
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