BOLDINE

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29157166 | https://www.ncbi.nlm.nih.gov/pubmed/29136766 | https://www.ncbi.nlm.nih.gov/pubmed/28826044 | https://www.ncbi.nlm.nih.gov/pubmed/25746354 | https://www.ncbi.nlm.nih.gov/pubmed/28719960

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
Acetylcholinesterase 207 Target ID: P22303\|\|\|Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29136766	Inhibitor 8297
Telomerase reverse transcriptase 10 Target ID: O14746 Gene ID: 7015.0 Gene Symbol: TERT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25746354	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Leishmaniasis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28719960	Primary	Basic research	Unknown Approved Use Unknown
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28826044	Primary	Preclinical	Unknown Approved Use Unknown
Mammary carcinoma 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27611982	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Antipoliovirus structure-activity relationships of some aporphine alkaloids.	1998 Apr	9584402
Protective effect of boldine on dopamine-induced membrane permeability transition in brain mitochondria and viability loss in PC12 cells.	2002 Feb 1	11853700
Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo").	2003 Apr	12747739
Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora.	2003 Jun	12770583
Spectroscopic study of antileishmanial drug incubated in the promastigotes of Leishmania mexicana.	2003 Nov	14583293
Reactive oxygen species (ROS) generation inhibited by aporphine and phenanthrene alkaloids semi-synthesized from natural boldine.	2004 Jun	15187389
[Alkaloids from the root of Lindera angustifolia].	2005 Oct	16408812
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	16254819
Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo.	2005 Sep	15944212
Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats.	2006 Oct	16924583
Advances in development of dopaminergic aporphinoids.	2007 Jan 25	17228858
Boldine: a potential new antiproliferative drug against glioma cell lines.	2009 Dec	19050827
The hunt for natural skin whitening agents.	2009 Dec 10	20054473
[Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography].	2009 Mar	19526789
Ascorbic acid and tetrahydrobiopterin potentiate the EDHF phenomenon by generating hydrogen peroxide.	2009 Nov 1	19592567
Anti-photoaging and photoprotective compounds derived from marine organisms.	2010 Apr 8	20479974
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	21111183
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	20022332
Cytotoxic thiocarbamate derivatives of boldine.	2010 Oct	21121254
Current and developing therapeutic agents in the treatment of Chagas disease.	2010 Sep 24	20957215
Boldine, a natural aporphine alkaloid, inhibits telomerase at non-toxic concentrations.	2015 Apr 25	25746354
Boldine enhances bile production in rats via osmotic and farnesoid X receptor dependent mechanisms.	2015 May 15	25771127

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 Dec 15 18:36:57 UTC 2023` Edited by `admin` on `Fri Dec 15 18:36:57 UTC 2023`
Record UNII	8I91GE2769
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BOLDINE

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 [MI]

Common Name

English

1,10-DIMETHOXY-2,9-DIHYDROXYAPORPHINE

Systematic Name

English

Boldine [WHO-DD]

Common 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