(+)-boldine
4H-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-
Identification
| Name | (+)-boldine |
| CAS Number | 476-70-0 |
| EINECS | 207-509-9 |
| FDA UNII | 8I91GE2769 |
| Molecular Formula | C19 H21 N O4 |
| Molecular Weight | 327.38017000 |
| MDL Number | MFCD00135040 |
| Nikkaji Number | J312.540H |
| Beilstein | 0094036 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 162.00 to 165.00 °C. @ 760.00 mm Hg |
| Boiling Point | 529.35 °C. @ 760.00 mm Hg (est) |
| Flash Point | 525.00 °F. TCC ( 273.90 °C. ) (est) |
| logP (o/w) | 0.837 (est) |
| Soluble in | water, 56.14 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 145 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES\nCARDIAC: CHANGE IN RATE\nVASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION', 'VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION\nLUNGS, THORAX, OR RESPIRATION: OTHER CHANGES\nCARDIAC: CHANGE IN RATE']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for (+)-boldine usage levels up to | not for fragrance use. |
| Recommendation for (+)-boldine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
aprophine alkaloid
(S)-
boldine
boldine-chloroform
4H-
dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-
4H-
dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-
4H-
dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-
4H-
dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-
(9S)-4,16-
dimethoxy-10-methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol
(6aS)-1,10-
dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
(S)-1,10-
dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
PubMed:
[Behavioural impairments and hallucinations after consumption of boldo leaf infusions].
PubMed:
A novel UPLC-MS/MS method for sensitive quantitation of boldine in plasma, a potential anti-inflammatory agent: application to a pharmacokinetic study in rats.
PubMed:
Surface enhanced Raman scattering study of the antioxidant alkaloid boldine using prismatic silver nanoparticles.
PubMed:
Immunomodulatory effect of an isolated fraction from Tinospora crispa on intracellular expression of INF-γ, IL-6 and IL-8.
PubMed:
Natural products as potential human ether-a-go-go-related gene channel inhibitors - screening of plant-derived alkaloids.
PubMed:
Evaluation of cytotoxic and chemotherapeutic properties of boldine in breast cancer using in vitro and in vivo models.
PubMed:
Antiplasmodial and antioxidant isoquinoline alkaloids from Dehaasia longipedicellata.
PubMed:
Natural compounds boldine and menthol are antagonists of human 5-HT3 receptors: implications for treating gastrointestinal disorders.
PubMed:
Boldine and related aporphines: from antioxidant to antiproliferative properties.
PubMed:
Boldine prevents renal alterations in diabetic rats.
PubMed:
Boldine induces cell cycle arrest and apoptosis in T24 human bladder cancer cell line via regulation of ERK, AKT, and GSK-3β.
PubMed:
Boldine improves endothelial function in diabetic db/db mice through inhibition of angiotensin II-mediated BMP4-oxidative stress cascade.
PubMed:
Development of an HPLC fluorescence method for determination of boldine in plasma, bile and urine of rats and identification of its major metabolites by LC-MS/MS.
PubMed:
Batch and Continuous Ultrasound Assisted Extraction of Boldo Leaves (Peumus boldus Mol.).
PubMed:
Boldine protects endothelial function in hyperglycemia-induced oxidative stress through an antioxidant mechanism.
PubMed:
Applied biological and physicochemical activity of isoquinoline alkaloids: oxoisoaporphine and boldine.
PubMed:
Acetylcholinesterase inhibition, antioxidant activity and toxicity of Peumus boldus water extracts on HeLa and Caco-2 cell lines.
PubMed:
(-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of Beilschmiedia kunstleri gamble.
PubMed:
The aporphine alkaloid boldine improves endothelial function in spontaneously hypertensive rats.
PubMed:
Anti-acetylcholinesterase, anti-α-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species.
PubMed:
Alkaloids from the Chinese vine Gnetum montanum.
PubMed:
Boldo prevents UV light and nitric oxide-mediated plasmid DNA damage and reduces the expression of Hsp70 protein in melanoma cancer cells.
PubMed:
(+)-Kunstlerone, a new antioxidant neolignan from the Leaves of Beilschmiedia kunstleri gamble.
PubMed:
Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia.
PubMed:
In vitro cytotoxic evaluation of a novel phosphinyl derivative of boldine.
PubMed:
New alkaloid antibiotics that target the DNA topoisomerase I of Streptococcus pneumoniae.
PubMed:
Cytotoxic thiocarbamate derivatives of boldine.
PubMed:
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.
PubMed:
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.
PubMed:
The aporphine alkaloid boldine induces adiponectin expression and regulation in 3T3-L1 cells.
PubMed:
(+)-N-(2-hydroxypropyl)lindcarpine: a new cytotoxic aporphine isolated from Actinodaphne pruinosa Nees.
PubMed:
[Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography].
PubMed:
Alkaloids from Lindera aggregata.
PubMed:
Grandine A, a new proaporphine alkaloid from the bark of Phoebe grandis.
PubMed:
Effect of boldo (Peumus boldus Molina) infusion on lipoperoxidation induced by cisplatin in mice liver.
PubMed:
Boldine: a potential new antiproliferative drug against glioma cell lines.
PubMed:
Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry.
PubMed:
5-Hydroxytryptamine2A receptor binding activity of compounds from Litsea sessilis.
PubMed:
Antioxidant and pro-oxidant properties of boldine on hippocampal slices exposed to oxygen-glucose deprivation in vitro.
PubMed:
Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers.
PubMed:
Characterization of isoquinoline alkaloids from Neolitsea sericea var. aurata by HPLC-SPE-NMR.
PubMed:
Studies of Genetic Variation of Essential Oil and Alkaloid Content in Boldo (Peumus boldus).
PubMed:
Advances in development of dopaminergic aporphinoids.
PubMed:
Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction.
PubMed:
Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats.
PubMed:
Sensitive quantification of apomorphine in human plasma using a LC-ESI-MS-MS method.
PubMed:
Antinociceptive and free radical scavenging activities of alkaloids isolated from Lindera angustifolia Chen.
PubMed:
[Alkaloids from the root of Lindera angustifolia].
PubMed:
8-NH2-boldine, an antagonist of alpha1A and alpha1B adrenoceptors without affinity for the alpha1D subtype: structural requirements for aporphines at alpha1-adrenoceptor subtypes.
PubMed:
Boldine and its antioxidant or health-promoting properties.
PubMed:
Photostability and photoprotection factor of boldine and glaucine.
PubMed:
Effect of boldine, secoboldine, and boldine methine on angiotensin II-induced neutrophil recruitment in vivo.
PubMed:
Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity.
PubMed:
Cytotoxic and antitumor potentialities of aporphinoid alkaloids.
PubMed:
Photochemistry of phytoalexins containing phenalenone-like chromophores: photophysics and singlet oxygen photosensitizing properties of the plant oxoaporphine alkaloid oxoglaucine.
PubMed:
Reactive oxygen species (ROS) generation inhibited by aporphine and phenanthrene alkaloids semi-synthesized from natural boldine.
PubMed:
Alkaloids from Cassytha filiformis and related aporphines: antitrypanosomal activity, cytotoxicity, and interaction with DNA and topoisomerases.
PubMed:
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.
PubMed:
Inhibitory action of conventional food-grade natural antioxidants and of natural antioxidants of new development on the thermal-induced oxidation of cholesterol.
PubMed:
Spectroscopic study of antileishmanial drug incubated in the promastigotes of Leishmania mexicana.
PubMed:
Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora.
PubMed:
Free-radical scavengers and antioxidants from Peumus boldus Mol. ("Boldo").
PubMed:
Effects of some antioxidative aporphine derivatives on striatal dopaminergic transmission and on MPTP-induced striatal dopamine depletion in B6CBA mice.
PubMed:
Protection against UVB irradiation by natural filters extracted from lichens.
PubMed:
Affinity profile at alpha(1)- and alpha(2)-adrenoceptor subtypes and in vitro cardiovascular actions of (+)-boldine.
PubMed:
Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity.
PubMed:
Protective effect of boldine on dopamine-induced membrane permeability transition in brain mitochondria and viability loss in PC12 cells.
PubMed:
Chemoprotective activity of boldine: modulation of drug-metabolizing enzymes.
PubMed:
Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products.
PubMed:
Free-radical-induced inactivation of lysozyme and carbonyl residue generation in protein are not necessarily associated.
PubMed:
Protective effect of boldine on oxidative mitochondrial damage in streptozotocin-induced diabetic rats.
PubMed:
Protective effects of boldine against free radical-induced erythrocyte lysis.
PubMed:
Biological disposition of boldine: in vitro and in vivo studies.
PubMed:
Halogenated boldine derivatives with enhanced monoamine receptor selectivity.
PubMed:
Toxicological evaluation of the hydro-alcohol extract of the dry leaves of Peumus boldus and boldine in rats.
PubMed:
Boldine action against the stannous chloride effect.
PubMed:
Dry plant extracts loaded on fumed silica for direct compression: preparation and preformulation.
PubMed:
Halogenated derivatives of boldine with high selectivity for alpha1A-adrenoceptors in rat cerebral cortex.
PubMed:
Biochemical and behavioral effects of boldine and glaucine on dopamine systems.
PubMed:
Glaucine analogues as inhibitors of mouse splenocyte activity.
PubMed:
Antipoliovirus structure-activity relationships of some aporphine alkaloids.
PubMed:
Studies on neuromuscular blockade by boldine in the mouse phrenic nerve-diaphragm.
PubMed:
Effects of boldine on mouse diaphragm and sarcoplasmic reticulum vesicles isolated from skeletal muscle.
PubMed:
Inhibition of eukaryote protein kinases by isoquinoline and oxazine alkaloids.
PubMed:
Protective effect of boldine in experimental colitis.
PubMed:
Antiplatelet effects of some aporphine and phenanthrene alkaloids in rabbits and man.
PubMed:
A possible structural determinant of selectivity of boldine and derivatives for the alpha 1A-adrenoceptor subtype.
PubMed:
The effect of S-(+)-boldine on the alpha 1-adrenoceptor of the guinea-pig aorta.
PubMed:
Determination of lauraceous aporphine alkaloids by high-performance liquid chromatography.
PubMed:
Novel liquid chromatographic assay for the low-level determination of apomorphine in plasma.
PubMed:
Cytoprotective and antioxidant effects of boldine on tert-butyl hydroperoxide-induced damage to isolated hepatocytes.
PubMed:
Antiplatelet and vasorelaxing actions of some aporphinoids.
PubMed:
The inhibitory effects of boldine, glaucine, and probucol on TPA-induced down regulation of gap junction function. Relationships to intracellular peroxides, protein kinase C translocation, and connexin 43 phosphorylation.
PubMed:
Boldine prevents human liver microsomal lipid peroxidation and inactivation of cytochrome P4502E1.
PubMed:
Structure-antioxidative activity relationships in benzylisoquinoline alkaloids.
PubMed:
Anti-inflammatory and antipyretic effects of boldine.
PubMed:
Mechanisms of vasorelaxation induced by N-allylsecoboldine in rat thoracic aorta.
PubMed:
Effects of boldine on cellular immune functions in vitro.
PubMed:
Evaluation of the genotoxic potential of the alkaloid boldine in mammalian cell systems in vitro and in vivo.
PubMed:
Trypanocidal effect of boldine and related alkaloids upon several strains of Trypanosoma cruzi.
PubMed:
Determination of boldine in drug formulations by first-derivative synchronous spectrofluorimetry.
PubMed:
Boldo and boldine: an emerging case of natural drug development.
PubMed:
Iron-reducing and free-radical-scavenging properties of apomorphine and some related benzylisoquinolines.
PubMed:
Different mechanism of relaxation induced by aporphine alkaloids in rat uterus.
PubMed:
Determination of boldine in plasma by high-performance liquid chromatography.
PubMed:
Selective action of two aporphines at alpha 1-adrenoceptors and potential-operated Ca2+ channels.
PubMed:
Antioxidant action of benzylisoquinoline alkaloids.
PubMed:
Inhibition of rat liver microsomal lipid peroxidation by boldine.
PubMed:
Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids.
PubMed:
Activity of boldine on rat ileum.
PubMed:
Genotoxicity of the boldine aporphine alkaloid in prokaryotic and eukaryotic organisms.
PubMed:
Antioxidant properties of the alkaloid boldine in systems undergoing lipid peroxidation and enzyme inactivation.
PubMed:
Hepatoprotective and anti-inflammatory effects of a traditional medicinal plant of Chile, Peumus boldus.
PubMed:
Genotoxic effect of alkaloids.
PubMed:
A study of the adrenergic activity of the alkaloids boldine and glaucine.
PubMed:
Neuroleptic-like, anticonvulsant and antinociceptive effects of aporphine alkaloids: bulbocapnine, corytuberine, boldine and glaucine.
PubMed:
Alkaloids of Litsea wightiana1.
PubMed:
Voltammetric study of boldine on stationary platinum electrode.
PubMed:
Toxic alkaloids and their interaction with microsomal cytochrome P-450 in vitro.
PubMed:
[Determination of boldine by HPLC (high pressure liquid chromatography) in Boldus extracts].
PubMed:
Biosynthesis of boldine (1,10-dimethoxy-6aalpha-aporphine-2,9-diol).
PubMed:
Fluorimetric analysis of alkaloids. Determination of serpentine, yohimbine, and boldine.
PubMed:
Stereochemical preferences for curarimimetic neuromuscular junction blockade I: enantiomeric monoquaternary amines as probes.
PubMed:
[Densitometric determination of boldine in boldo extracts].
PubMed:
[Determination of boldine in Folium boldo and in the commercial preparation Boldiné Houdé].
PubMed:
[A colored reaction of boldine].
PubMed:
[Colorimetric determination of boldine].