Amurensin
|
|
Names
|
IUPAC name
7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxy-8-(3-hydroxy-3-methylbutyl)flavone
|
Systematic IUPAC name
3,5-Dihydroxy-8-(3-hydroxy-3-methylbutyl)-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
|
Identifiers
|
|
|
|
|
ChemSpider
|
|
|
|
UNII
|
|
|
|
InChI=1S/C26H30O12/c1-26(2,35)8-7-13-15(36-25-22(34)20(32)18(30)16(10-27)37-25)9-14(29)17-19(31)21(33)23(38-24(13)17)11-3-5-12(28)6-4-11/h3-6,9,16,18,20,22,25,27-30,32-35H,7-8,10H2,1-2H3/t16-,18-,20+,22-,25-/m1/s1 N Key: UNHHWEHQUUGKEE-MLLLWRCASA-N N InChI=1/C26H30O12/c1-26(2,35)8-7-13-15(36-25-22(34)20(32)18(30)16(10-27)37-25)9-14(29)17-19(31)21(33)23(38-24(13)17)11-3-5-12(28)6-4-11/h3-6,9,16,18,20,22,25,27-30,32-35H,7-8,10H2,1-2H3/t16-,18-,20+,22-,25-/m1/s1 Key: UNHHWEHQUUGKEE-MLLLWRCABA
|
CC(C)(CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
|
Properties
|
|
C26H30O12
|
Molar mass
|
534.50 g/mol
|
Density
|
1.581 g/mL
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
|
Amurensin is a flavonol, a type of flavonoid. It is the tert-amyl alcohol derivative of kaempferol 7-O-glucoside. It can be found in Phellodendron amurense.[1]
6"'-O-acetyl amurensin is found in the leaves of Phellodendron japonicum.[2]
References
- ^ Two New Flavonoid Glycosides from the Leaves of Phellodendron amurense Ruprecht. Masao Hasegawa and Teruo Shirato, J. Am. Chem. Soc., 1953, 75 (22), pages 5507–5511, doi:10.1021/ja01118a013
- ^ Constituents of Leaves of Phellodendron japonicum MAXIM. and Their Antioxidant Activity, Chih-Yang Chiu, Chia-Ying Li, Chao-Chen Chiu, Masatake Niwa, Susumu Kitanaka, Amooru Gangaiah Damu, E-Jian Lee and Tian-Shung Wu, Chem. Pharm. Bull., Vol. 53, pages 1118-1121 (2005), doi:10.1248/cpb.53.1118
Flavonols and their conjugates |
---|
Backbone | |
---|
Flavonols | Aglycones | |
---|
Conjugates | Glycosides of herbacetin | |
---|
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 | |
---|
Conjugates of quercetin | |
---|
|
---|
|
---|
O-Methylated flavonols | Aglycones | |
---|
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 |
- Icariin
- Phelloside
- Dihydrophelloside
- Rutin S
|
---|
|
---|
Pyranoflavonols | |
---|
Furanoflavonols | |
---|
Semisynthetic | |
---|