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] Blodine 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

Blodine 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]

Blodine has shown nootropic activity in mice, specifically by significantly improving learning and memory. [5]

Blodine has shown antiepileptic activity in mice against seizures induced by Pentylenetetrazole (PTZ). [6]

Blodine protects against paracetamol induced liver inflammation and acute hepatic necrosis in mice. [7]

Blodine 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 Blodine. Glaucine is a dimethyl ether analog of Blodine.

Topical use of DiAcetyl-Blodine 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. https://www.sciencedirect.com/science/article/abs/pii/S0009279705002206
  4. https://doi.org/10.1097/fjc.0000000000000185
  5. https://www.sciencedirect.com/science/article/abs/pii/S0753332217331293
  6. https://www.tandfonline.com/doi/abs/10.1080/01616412.2017.1402500
  7. https://onlinelibrary.wiley.com/doi/10.1002/jbt.22697
  8. https://onlinelibrary.wiley.com/doi/10.1111/nmo.12334
  9. https://www.ncbi.nlm.nih.gov/books/NBK513318/
  10. https://www.drugs.com/drug-class/5ht3-receptor-antagonists.html
  11. https://www.mdpi.com/1999-4923/15/3/901
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