Boldine

Boldine
Identifiers
CAS Number	476-70-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL388342 ;
ChemSpider	9748 ;
ECHA InfoCard	100.006.828
PubChem CID	10154;
UNII	8I91GE2769 ;
CompTox Dashboard (EPA)	DTXSID40883394 ;
	InChI 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 Key: LZJRNLRASBVRRX-ZDUSSCGKSA-N ; 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;
	SMILES CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)O;
Properties
Chemical formula	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

Boldine is an alkaloid of the aporphine class that can be found in the boldo tree[1] and in Lindera aggregata.[2]

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.[3] It also exhibits anti-inflammatory activity, reducing the expression of TNF-α in Ab-induced chronic inflammation in APP/PSI mice.[4]

Boldine also exhibits neuroprotective effects because of its ability to cross the blood brain barrier (BBB) when administered orally, inhibit connexin hemichannel activity in glial cells (microglia, astrocytes) and neurons without affecting gap junctional communication and reduce neuronal injury resulting from Ab-induced chronic inflammation.[4]

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.
Zhang, A.; Zhang, Y.; Branfman, A. R.; Baldessarini, R. J.; Neumeyer, J. L. (2007). "Advances in Development of Dopaminergic Aporphinoids". Journal of Medicinal Chemistry. 50 (2): 171–181. doi:10.1021/jm060959i. PMID 17228858.
Yi, Chenju; Ezan, Pascal; Fernández, Paola; Schmitt, Julien; Sáez, Juan C.; Giaume, Christian; Koulakoff, Annette (2017). "Inhibition of glial hemichannels by boldine treatment reduces neuronal suffering in a murine model of Alzheimer's disease". Glia. 65 (10): 1607–1625. doi:10.1002/glia.23182. ISSN 1098-1136. PMID 28703353.

External links

Boldine review

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[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] Zhang, A.; Zhang, Y.; Branfman, A. R.; Baldessarini, R. J.; Neumeyer, J. L. (2007). "Advances in Development of Dopaminergic Aporphinoids". Journal of Medicinal Chemistry. 50 (2): 171–181. doi:10.1021/jm060959i. PMID 17228858.

[:0-4] Yi, Chenju; Ezan, Pascal; Fernández, Paola; Schmitt, Julien; Sáez, Juan C.; Giaume, Christian; Koulakoff, Annette (2017). "Inhibition of glial hemichannels by boldine treatment reduces neuronal suffering in a murine model of Alzheimer's disease". Glia. 65 (10): 1607–1625. doi:10.1002/glia.23182. ISSN 1098-1136. PMID 28703353.