| |
| Names | |
|---|---|
| IUPAC name
1,10-Dimethoxyaporphine-2,9-diol
| |
| Systematic IUPAC name
(6aS)-1,10-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.828 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C19H21NO4 | |
| Molar mass | 327.380 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Boldine is an alkaloid of the aporphine class that can be found in the boldo tree. It is the most abundant aporphine alkaloid found in Boldo.[1] Boldine is also found in Lindera aggregata.[2]
Pharmacology
Boldine has been investigated for its cyto-protective, anti-tumour promoting, anti-inflammatory, anti-diabetic and anti-atherogenic effect and is particularly believed to be a strong antioxidant.[3][4]
Boldine has shown nootropic activity in mice, specifically by significantly improving learning and memory. [5]
Boldine has shown antiepileptic activity in mice against seizures induced by Pentylenetetrazole (PTZ). [6]
Boldine protects against paracetamol induced liver inflammation and acute hepatic necrosis in mice. [7]
Boldine is a 5-HT3 receptor antagonist.[8] 5-HT3A antagonists have been shown to help prevent nausea and vomiting as well as the negative effects of serotonin in the G.I tract. [9][10]
Glaucine is structurally related to Boldine. Glaucine is a dimethyl ether analog of Boldine.
Topical use of DiAcetyl-Boldine in the form of a microemulsion has been studied for chemoprotection against Melanoma.[11]
References
- ^ O'Brien, P.; Carrasco-Pozo, C.; Speisky, H. (2006). "Boldine and its Antioxidant or Health-Promoting Properties". Chemico-Biological Interactions. 159 (1): 1–17. doi:10.1016/j.cbi.2005.09.002. PMID 16221469.
- ^ Han, Z.; Zheng, Y.; Chen, N.; Luan, L.; Zhou, C.; Gan, L.; Wu, Y. (2008). "Simultaneous Determination of Four Alkaloids in Lindera aggregata by Ultra-High-Pressure Liquid Chromatography–Tandem Mass Spectrometry". Journal of Chromatography A. 1212 (1–2): 76–81. doi:10.1016/j.chroma.2008.10.017. PMID 18951552.
- ^ o'Brien, Peter; Carrasco-Pozo, Catalina; Speisky, Hernán (2006). "Boldine and its antioxidant or health-promoting properties". Chemico-Biological Interactions. 159 (1): 1–17. doi:10.1016/j.cbi.2005.09.002. PMID 16221469.
- ^ Lau, Yeh Siiang; Ling, Wei Chih; Murugan, Dharmani; Mustafa, Mohd Rais (2015). "Boldine Ameliorates Vascular Oxidative Stress and Endothelial Dysfunction". Journal of Cardiovascular Pharmacology. 65 (6): 522–531. doi:10.1097/fjc.0000000000000185. PMC 4461386. PMID 25469805.
- ^ Dhingra, Dinesh; Soni, Kapil (2018). "Behavioral and biochemical evidences for nootropic activity of boldine in young and aged mice". Biomedicine & Pharmacotherapy. 97: 895–904. doi:10.1016/j.biopha.2017.11.011. PMID 29136766.
- ^ . Neurological Research. 40 (2): 146–152. doi:10.1080/01616412.2017.1402500. PMID 29157166. S2CID 8128417.
- ^ Ezhilarasan, Devaraj; Raghunandhakumar, Subramanian (2021). "Boldine treatment protects acetaminophen‐induced liver inflammation and acute hepatic necrosis in mice". Journal of Biochemical and Molecular Toxicology. 35 (4): e22697. doi:10.1002/jbt.22697. PMID 33393705. S2CID 230488571.
- ^ Walstab, J.; Wohlfarth, C.; Hovius, R.; Schmitteckert, S.; Röth, R.; Lasitschka, F.; Wink, M.; Bönisch, H.; Niesler, B. (2014). "Natural compounds boldine and menthol are antagonists of human 5-HT3receptors: Implications for treating gastrointestinal disorders". Neurogastroenterology & Motility. 26 (6): 810–820. doi:10.1111/nmo.12334. PMID 24708203. S2CID 21833146.
- ^ Theriot, J.; Wermuth, H. R.; Ashurst, J. V. (2023). "Antiemetic Serotonin-5-HT3 Receptor Blockers". StatPearls. PMID 30020690.
- ^ "List of 5HT3 receptor antagonists (5hydroxytryptamine receptor antagonists)".
- ^ Al Saqr, Ahmed; Annaji, Manjusha; Poudel, Ishwor; Aldawsari, Mohammed F.; Alrbyawi, Hamad; Mita, Nur; Dhanasekaran, Muralikrishnan; Boddu, Sai H. S.; Neupane, Rabin; Tiwari, Amit K.; Babu, R. Jayachandra (2023). "Topical Delivery of Diacetyl Boldine in a Microemulsion Formulation for Chemoprotection against Melanoma". Pharmaceutics. 15 (3): 901. doi:10.3390/pharmaceutics15030901. PMC 10054442. PMID 36986762.
 | This article about an alkaloid is a stub. You can help Wikipedia by expanding it. |
This page was last edited on 4 July 2023, at 21:58