Boldine - CAS 476-70-0
Catalog number:
476-70-0
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C19H21NO4
Molecular Weight:
327.37
COA:
Inquire
Targets:
Others
Description:
Boldine, an aporphine alkaloid extracted from the leaves and bark of P. boldus, potent antioxidant activity has been linked to anti-inflammatory, anti-pyretic, anti-diabetic, anti-atherogenic, anti-platelet, anti-tumor, UV-protective, and hepatoprotective effects.
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Purity:
≥95%
Appearance:
Yellow to Brown Solid
Synonyms:
5,6,6aS,7-tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol;(+)-(S)-Boldine 2,9-Dihydroxy-1,10-dimethoxyaporphine;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
Antioxidant and free-radical scavenging ability.
Quality Standard:
Enterprise standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Quantity:
Milligrams-Grams
Boiling Point:
529.3ºC at 760 mmHg
Melting Point:
162-164 ºC
Density:
1.29 g/cm3
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
Canonical SMILES:
OC1=C(OC)C2=C3[C@](N(C)CCC3=C1)([H])CC4=CC(O)=C(OC)C=C42
1.Oxaliplatin analogues with carboxy derivatives of boldine with enhanced antioxidant activity.
Mellado M1, Jara C2, Astudillo D3, Villena J3, Reveco PG1, Thomet FA1. Bioinorg Chem Appl. 2015;2015:920143. doi: 10.1155/2015/920143. Epub 2015 Feb 28.
A new oxaliplatin analog [Pt(dach)(L5)] (1) was synthesized and characterized as a continuation of a study of the previously reported [Pt(dach)(L6)] (2), where dach = (1R,2R)-diaminocyclohexane, L5 = 3-carboxyboldine, and L6 = 3-carboxypredicentrine. Compounds 1 and 2 exhibited a substantially enhanced antioxidant activity compared to oxaliplatin (130 and 30 times for 1 and 13 and 4 times for 2 using the DPPH and FRAP assays, resp.). In addition, 1 and 2 exhibited cytotoxic activity in the same range as oxaliplatin toward the two human tumor cell lines (MCF-7 and HT-29) studied and two to four times lower activity in the human colon nontumor cell line (CCD-841). Preadministration of L5 or L6 to the colon tumor (HT-29) and the colon nontumor (CCD-841) cell lines prior to oxaliplatin addition increased the viability of the nontumor cell line to a greater extent than that of the tumor cell line.
2.[Alkaloids from roots and stems of Litsea cubeba].
Zhang SY, Guo Q, Cao Y, Zhang Y, Gao XL, Tu PF, Chai XY. Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(20):3964-8.
A phytochemical investigation on the roots and stems of Litsea cubeba led to the isolation of seven isoquinolone alkaloids. By spectroscopic analysis and comparison of their 1H and 13C-NMR data with those in literatures, these alkaloids were identified as (+)-norboldine (1), (+)-boldine (2), (+)-reticuline (3), (+)-laurotetanine (4), (+)-isoboldine (5), (+)-N-methyl-laurotetanine (6), and berberine (7), respectively. Among them, 7 was isolated from the genus for the first time. The evaluation of these compounds showed weak anti-inflammatory activity against NO production in RAW 267.4 and BV-2 cells.
3.Boldine suppresses dextran sulfate sodium-induced mouse experimental colitis: NF-κB and IL-6/STAT3 as potential targets.
Pandurangan AK1, Mohebali N1, Hasanpourghadi M1, Looi CY1, Mustafa MR1, Mohd Esa N2,3. Biofactors. 2016 Feb 19. doi: 10.1002/biof.1267. [Epub ahead of print]
Ulcerative colitis (UC) is a nonspecific inflammatory disorder characterized by oxidative and nitrosative stress, leucocyte infiltration, and upregulation of inflammatory mediators. Boldine is an alkaloid compound found in Boldo tree, with multiple pharmacological actions, mainly anti-inflammatory, antioxidant, antitumor, and immunomodulatory activities. Hence, the effect of boldine for its anti-inflammatory properties against dextran sulfate sodium (DSS)-induced UC in BALB/c mice was studied. Administration of boldine to DSS-induced mice protects colon damage by reduced disease activity index, spleen weight, and increased colon length. Also administration of boldine showed a reduction in the activity of myeloperoxidase (MPO) and CD 68+ expression. Boldine reduced the colon damage, with significant reductions in both the extent and the severity of the inflammation as well as in crypt damage and leukocyte infiltration in the mucosa. Analysis in vivo showed clear decrease in the production of tumor necrosis factor (TNF)-α, Interleukin (IL)-6, IL-17, and signal transducer and activator of transcription-(p-STAT3)Y705 with nuclear factor (p65-NF-κB) production being reduced significantly.
4.Screening of the Pan-African natural product library identifies ixoratannin A-2 and boldine as novel HIV-1 inhibitors.
Tietjen I1, Ntie-Kang F2, Mwimanzi P3, Onguéné PA4, Scull MA5, Idowu TO6, Ogundaini AO6, Meva'a LM4, Abegaz BM7, Rice CM5, Andrae-Marobela K8, Brockman MA9, Brumme ZL10, Fedida D11. PLoS One. 2015 Apr 1;10(4):e0121099. doi: 10.1371/journal.pone.0121099. eCollection 2015.
The continued burden of HIV in resource-limited regions such as parts of sub-Saharan Africa, combined with adverse effects and potential risks of resistance to existing antiretroviral therapies, emphasize the need to identify new HIV inhibitors. Here we performed a virtual screen of molecules from the pan-African Natural Product Library, the largest collection of medicinal plant-derived pure compounds on the African continent. We identified eight molecules with structural similarity to reported interactors of Vpu, an HIV-1 accessory protein with reported ion channel activity. Using in vitro HIV-1 replication assays with a CD4+ T cell line and peripheral blood mononuclear cells, we confirmed antiviral activity and minimal cytotoxicity for two compounds, ixoratannin A-2 and boldine. Notably, ixoratannin A-2 retained inhibitory activity against recombinant HIV-1 strains encoding patient-derived mutations that confer resistance to protease, non-nucleoside reverse transcriptase, or integrase inhibitors.
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CAS 476-70-0 Boldine

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