Boldine

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]

For other uses, see Boldin.
Boldine
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
UNII
  • 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 checkY
    Key: LZJRNLRASBVRRX-ZDUSSCGKSA-N checkY
  • InChI=1/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
    Key: LZJRNLRASBVRRX-ZDUSSCGKBM
  • CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)O
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).
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Infobox references

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
  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. Moezi, Leila; Yahosseini, Siranoush; Jamshidzadeh, Akram; Dastgheib, Mona; Pirsalami, Fateme (2018). "Sub-chronic boldine treatment exerts anticonvulsant effects in mice". Neurological Research. 40 (2): 146–152. doi:10.1080/01616412.2017.1402500. PMID 29157166. S2CID 8128417.
  7. 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.
  8. 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.
  9. Theriot, J.; Wermuth, H. R.; Ashurst, J. V. (2023). "Antiemetic Serotonin-5-HT3 Receptor Blockers". StatPearls. PMID 30020690.
  10. "List of 5HT3 receptor antagonists (5hydroxytryptamine receptor antagonists)".
  11. 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.
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