Boldine

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
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). verify (what is ?) Infobox references

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[edit]

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[edit]

^ 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.
^ 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.
^ 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.

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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] '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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