Morin (Flavonol)

Morin
Names
	IUPAC name 2′,3,4′,5,7-Pentahydroxyflavone
	Systematic IUPAC name 2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
	Other names Aurantica; Al-Morin; Morin hydrate; Calico Yellow; Toxylon pomiferum; Bois d'arc; Osage orange extract
Identifiers
CAS Number	654055-01-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:75092;
ChEMBL	ChEMBL28626 ;
ChemSpider	4444989 ;
IUPHAR/BPS	411;
KEGG	C10105 ;
PubChem CID	5281670;
	InChI InChI=1S/C15H10O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,16-19,21H Key: YXOLAZRVSSWPPT-UHFFFAOYSA-N ; InChI=1/C15H10O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,16-19,21H Key: YXOLAZRVSSWPPT-UHFFFAOYAH;
	SMILES O=C1c3c(O/C(=C1/O)c2ccc(O)cc2O)cc(O)cc3O;
Properties
Chemical formula	C15H10O7
Molar mass	302.238 g·mol−1
Density	1.799 g/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Morin is a yellow chemical compound that can be isolated from Maclura pomifera (Osage orange), Maclura tinctoria (old fustic), and from leaves of Psidium guajava (common guava).^[1] In a preclinical in vitro study, morin was found to be a weak inhibitor of fatty acid synthase with an IC₅₀ of 2.33 μM.^[2] Morin was also found to inhibit amyloid formation by islet amyloid polypeptide (or amylin) and disaggregate amyloid fibers.^[3]

Morin exhibit inhibitory action against IgE-mediated allergic response. Morin treatment significantly down-regulated expressions of BLT2, NF-κB, and Th2-cytokine (TNF-α, IL-1β, IL-4, IL-6, and IL-13) in lungs of murine model of allergic asthma.^[4]

Morin can be used to test for the presence of aluminium or tin in a solution, since it forms characteristically fluorescent coordination complexes with them under UV light.

Glycosides

Morin-3-O-arabinoside^[1]
Morin-3-O-lyxoside^[1]

References

↑ ^1.0 ^1.1 ^1.2 Rattanachaikunsopon, Pongsak; Phumkhachorn, Parichat (2007). "Bacteriostatic effect of flavonoids isolated from leaves of Psidium guajava on fish pathogens". Fitoterapia 78 (6): 434–436. doi:10.1016/j.fitote.2007.03.015. PMID 17553634.
↑ Tian, Wei-Xi (2006). "Inhibition of Fatty Acid Synthase by Polyphenols". Current Medicinal Chemistry 13 (8): 967–977. doi:10.2174/092986706776361012. PMID 16611078.
↑ Noor, Harris; Cao, Ping; Raleigh, Daniel P. (2012). "Morin hydrate inhibits amyloid formation by islet amyloid polypeptide and disaggregates amyloid fibers". Protein Science 21 (3): 373–382. doi:10.1002/pro.2023. PMID 22238175.
↑ Kandhare, Amit D.; Liu, Zihao; Mukherjee, Anwesha A.; Bodhankar, Subhash L. (2019). "Therapeutic Potential of Morin in Ovalbumin-induced Allergic Asthma Via Modulation of SUMF2/IL-13 and BLT2/NF-kB Signaling Pathway". Current Molecular Pharmacology 12 (2): 122–138. doi:10.2174/1874467212666190102105052. PMID 30605067.

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[Psidium-1] 1.0 ^1.1 ^1.2 Rattanachaikunsopon, Pongsak; Phumkhachorn, Parichat (2007). "Bacteriostatic effect of flavonoids isolated from leaves of Psidium guajava on fish pathogens". Fitoterapia 78 (6): 434–436. doi:10.1016/j.fitote.2007.03.015. PMID 17553634.

[2] Tian, Wei-Xi (2006). "Inhibition of Fatty Acid Synthase by Polyphenols". Current Medicinal Chemistry 13 (8): 967–977. doi:10.2174/092986706776361012. PMID 16611078.

[Noor2012-3] Noor, Harris; Cao, Ping; Raleigh, Daniel P. (2012). "Morin hydrate inhibits amyloid formation by islet amyloid polypeptide and disaggregates amyloid fibers". Protein Science 21 (3): 373–382. doi:10.1002/pro.2023. PMID 22238175.

[4] Kandhare, Amit D.; Liu, Zihao; Mukherjee, Anwesha A.; Bodhankar, Subhash L. (2019). "Therapeutic Potential of Morin in Ovalbumin-induced Allergic Asthma Via Modulation of SUMF2/IL-13 and BLT2/NF-kB Signaling Pathway". Current Molecular Pharmacology 12 (2): 122–138. doi:10.2174/1874467212666190102105052. PMID 30605067.

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Names


IUPAC name 2′,3,4′,5,7-Pentahydroxyflavone
Systematic IUPAC name 2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
Other names Aurantica Al-Morin Morin hydrate Calico Yellow Toxylon pomiferum Bois d'arc Osage orange extract
Identifiers
CAS Number	654055-01-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75092
ChEMBL	ChEMBL28626^Y
ChemSpider	4444989^Y
IUPHAR/BPS	411
KEGG	C10105^Y
PubChem CID	5281670
InChI InChI=1S/C15H10O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,16-19,21H^Y Key: YXOLAZRVSSWPPT-UHFFFAOYSA-N^Y InChI=1/C15H10O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,16-19,21H Key: YXOLAZRVSSWPPT-UHFFFAOYAH
SMILES O=C1c3c(O/C(=C1/O)c2ccc(O)cc2O)cc(O)cc3O
Properties
Chemical formula	C₁₅H₁₀O₇
Molar mass	302.238 g·mol⁻¹
Density	1.799 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references