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 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

Tracking categories (test):

* SizeSet

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. ↑ 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.
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.

* v
* t
* e

Flavonols and their conjugates

Backbone|

| Aglycones|

* 3-Hydroxyflavone (synthetic) and derivatives

|

Flavonols|

| Aglycones|

* Fisetin
* Galangin
* Gossypetin
* Herbacetin
* Kaempferol
* Morin
* Myricetin
* Quercetagetin
* Quercetin
* Robinetin

|

Conjugates|

| Glycosides of herbacetin|

* Rhodionin
* Rhodiosin

|

Glycosides of kaempferol|

* Afzelin (Kaempferol 3-rhamnoside)
* Astragalin (kaempferol 3-O-glucoside)
* Kaempferitrin (kaempferol 3,7-dirhamnoside)
* Juglanin (Kaempferol 3-O-arabinoside)
* Kaempferol 3-alpha-L-arabinopyranoside
* Kaempferol 3-alpha-D-arabinopyranoside
* Kaempferol 7-alpha-L-arabinoside
* Kaempferol 7-O-glucoside
* Kaempferol 3-lathyroside
* Kaempferol 4'-rhamnoside
* Kaempferol 5-rhamnoside
* Kaempferol 7-rhamnoside
* Kaempferol 7-O-alpha-L-rhamnofuranoside
* Kaempferol 3-xyloside
* Kaempferol 7-xyloside
* Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
* Kaempferol 3-O-rutinoside
* Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
* Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin|

* Betmidin (Myricetin 3-O-arabinoside)
* Myricetin 3-O-rutinoside
* Myricetin-3-O-neohesperidoside
* Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin|

| Sulfates|

* Quercetin 3-O-sulfate
* Quercetin 3,3'-bissulfate
* Quercetin 3,4'-bissulfate

|

Glycosides|

* Avicularin (quercetin-3-O-α-L-arabinofuranoside)
* CTN-986
* Guaijaverin (quercetin 3-O-arabinoside)
* Heliosin (quercetin 3-digalactoside)
* Hyperoside (quercetin 3-O-galactoside)
* Isoquercetin (quercetin 3-O-glucoside)
* Miquelianin (quercetin 3-O-glucuronide)
* Quercetin 3,4'-diglucoside
* Quercetin-3-sophorodide
* Quercitrin (quercetin 3-O-rhamnoside)
* Rutin (quercetin rutinoside)
* Reinutrin (quercetin-3-D-xyloside)
* Spiraeoside (quercetin 4'-O-glucoside)
* Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols|

| Aglycones|

* 5-O-methylmyricetin
* Annulatin
* Ayanin
* Axillarin
* Azaleatin
* Brickellin
* Centaureidin
* Chrysosplenetin
* Combretol
* Ermanin
* Eupatolitin
* Eupalitin
* Europetin
* Isorhamnetin
* Jaceidin
* Kaempferide
* Kumatakenin
* Laricitrin
* Natsudaidain
* Ombuin
* Pachypodol
* Patuletin
* Retusin
* Mearnsetin
* Rhamnazin
* Rhamnetin
* Santin
* Spinacetin
* Syringetin
* Tamarixetin

|

Glycosides|

| of isorhamnetin|

* Narcissin (Isorhamnetin 3-O-rutinoside)
* Isorhamnetin 3-O-glucoside
* Tamarixetin 7-rutinoside

|

other|

* Azalein (Azaleatin 3-O-α-L-rhamnoside)
* Centaurein (Centaureidin 7-O-glucoside)
* Eupalin (Eupalitin 3-0-rhamnoside)
* Eupatolin (Eupatolitin 3-O-rhamnoside)
* Jacein (Jaceidin 7-O-glucoside)
* Patulitrin (Patuletin 7-O-glucoside
* Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols|

| Aglycones|

* Noricaritin
* Dihydronoricaritin

|

Glycosides|

* Amurensin
* Icariin
* Phelloside
* Dihydrophelloside
* Rutin S

Pyranoflavonols|

| Aglycones|

* Karanjachromene

|

Furanoflavonols|

| Aglycones|

* Karanjin

|

Glycosides|

* Pongamoside A, B and C

Semisynthetic|

| Glycosides|

* Hydroxyethylrutosides
* Monoxerutin
* Troxerutin

|

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