Boldine
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MedKoo CAT#: 600118

CAS#: 476-70-0

Description: Boldine is an alkaloid of the aporphine class that can be found in the boldo tree and in Lindera aggregata. Boldine has antioxidant activity that effectively protects against free radical induced lipid peroxidation or enzyme inactivation. In addition, it has alpha-adrenergic antagonist activities in vascular tissue, and it has also been reported to have hepatoprotective, cytoprotective, antipyretic and anti-inflammatory effects.


Chemical Structure

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Boldine
CAS# 476-70-0

Theoretical Analysis

MedKoo Cat#: 600118
Name: Boldine
CAS#: 476-70-0
Chemical Formula: C19H21NO4
Exact Mass: 327.15
Molecular Weight: 327.370
Elemental Analysis: C, 69.71; H, 6.47; N, 4.28; O, 19.55

Price and Availability

Size Price Availability Quantity
1g USD 550 2 Weeks
2g USD 950 2 Weeks
5g USD 1950 2 Weeks
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Synonym: Boldine;

IUPAC/Chemical Name: 1,10-DIMETHOXY-2,9-DIHYDROXYAPORPHINE

InChi Key: LZJRNLRASBVRRX-ZDUSSCGKSA-N

InChi Code: 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

SMILES Code: CN([C@@](CC1=C2C=C(OC)C(O)=C1)3[H])CCC4=C3C2=C(OC)C(O)=C4

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects.
In vitro activity: Quantification of SV2 puncta/20 μm process length showed a significant reduction in SV2 labeling in AβO-treated neurons (p < 0.05) and this effect was reduced when the neurons were co-incubated with AβO and 10 μM boldine (p < 0.05) (Figure 3B), suggesting a protective effect of boldine against AβO-induced synaptic damage. Moreover, incubation of the hippocampal neurons with 10 μM boldine alone had no effect on the SV2 puncta (Figures 3A,B). Reference: Front Neurosci. 2021; 15: 617821. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7933475/
In vivo activity: Treatment of boldine protected the rat liver against reactive oxygen species such as hydrogen peroxide, superoxide, protein carbonyl and lipid peroxide during hepatocarcinogenesis by boosted antioxidants-superoxide dismutase (SOD), catalase (CAT). Boldine caused substantial enhanced detoxification process by moderating phase I and II xenobiotic metabolizing enzymes. In addition, the study was found that boldine significantly inhibited the cellular proliferative markers like PCNA and Ki67 and regulated the specific cell cycle associated proteins by up-regulated expression of p21Cip1/Kip1 and p27 Cip1/Kip1 and down-regulated expression of Cyclin D1, CDK 4, Cyclin E1, and CDK 2. Reference: Anticancer Agents Med Chem. 2021 Feb 2. https://pubmed.ncbi.nlm.nih.gov/33535961/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 71.7 218.93
DMSO:PBS (pH 7.2) (1:1) 0.5 1.53
DMF 50.0 152.73
Ethanol 30.0 91.64

Preparing Stock Solutions

The following data is based on the product molecular weight 327.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Toledo JP, Fernández-Pérez EJ, Ferreira IL, Marinho D, Riffo-Lepe NO, Pineda-Cuevas BN, Pinochet-Pino LF, Burgos CF, Rego AC, Aguayo LG. Boldine Attenuates Synaptic Failure and Mitochondrial Deregulation in Cellular Models of Alzheimer's Disease. Front Neurosci. 2021 Feb 19;15:617821. doi: 10.3389/fnins.2021.617821. PMID: 33679301; PMCID: PMC7933475. 2. Tomšík P, Mičuda S, Muthná D, Čermáková E, Havelek R, Rudolf E, Hroch M, Kadová Z, Řezáčová M, Ćmielová J, Živný P. Boldine Inhibits Mouse Mammary Carcinoma In Vivo and Human MCF-7 Breast Cancer Cells In Vitro. Planta Med. 2016 Nov;82(16):1416-1424. doi: 10.1055/s-0042-113611. Epub 2016 Sep 9. PMID: 27611982. 3. Subramaniam N, Kannan P, Sundaram J, Mari A, Velli SK, Salam S, Krishnan P, Balaraman G, Thiruvengadam D. Potential Chemopreventive role of Boldine against Hepatocellular Carcinoma via modulation of Cell Cycle Proteins in Rat Model. Anticancer Agents Med Chem. 2021 Feb 2. doi: 10.2174/1871520621666210203102854. Epub ahead of print. PMID: 33535961. 4. Ezhilarasan D, Raghunandhakumar S. Boldine treatment protects acetaminophen-induced liver inflammation and acute hepatic necrosis in mice. J Biochem Mol Toxicol. 2021 Apr;35(4):e22697. doi: 10.1002/jbt.22697. Epub 2021 Jan 4. PMID: 33393705.
In vitro protocol: 1. Toledo JP, Fernández-Pérez EJ, Ferreira IL, Marinho D, Riffo-Lepe NO, Pineda-Cuevas BN, Pinochet-Pino LF, Burgos CF, Rego AC, Aguayo LG. Boldine Attenuates Synaptic Failure and Mitochondrial Deregulation in Cellular Models of Alzheimer's Disease. Front Neurosci. 2021 Feb 19;15:617821. doi: 10.3389/fnins.2021.617821. PMID: 33679301; PMCID: PMC7933475. 2. Tomšík P, Mičuda S, Muthná D, Čermáková E, Havelek R, Rudolf E, Hroch M, Kadová Z, Řezáčová M, Ćmielová J, Živný P. Boldine Inhibits Mouse Mammary Carcinoma In Vivo and Human MCF-7 Breast Cancer Cells In Vitro. Planta Med. 2016 Nov;82(16):1416-1424. doi: 10.1055/s-0042-113611. Epub 2016 Sep 9. PMID: 27611982.
In vivo protocol: 1. Subramaniam N, Kannan P, Sundaram J, Mari A, Velli SK, Salam S, Krishnan P, Balaraman G, Thiruvengadam D. Potential Chemopreventive role of Boldine against Hepatocellular Carcinoma via modulation of Cell Cycle Proteins in Rat Model. Anticancer Agents Med Chem. 2021 Feb 2. doi: 10.2174/1871520621666210203102854. Epub ahead of print. PMID: 33535961. 2. Ezhilarasan D, Raghunandhakumar S. Boldine treatment protects acetaminophen-induced liver inflammation and acute hepatic necrosis in mice. J Biochem Mol Toxicol. 2021 Apr;35(4):e22697. doi: 10.1002/jbt.22697. Epub 2021 Jan 4. PMID: 33393705.

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1: Muthna D, Cmielova J, Tomsik P, Rezacova M. Boldine and related aporphines: from antioxidant to antiproliferative properties. Nat Prod Commun. 2013 Dec;8(12):1797-800. Review. PubMed PMID: 24555301.