Amurensin (flavonol)

Last updated
Amurensin
Amurensin.svg
Amurensin ball-and-stick.png
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
3D model (JSmol)
ChemSpider
PubChem CID
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 X mark.svgN
    Key: UNHHWEHQUUGKEE-MLLLWRCASA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Related Research Articles

<i>Phellodendron</i> Genus of trees

Phellodendron, or cork-tree, is a genus of deciduous, dioecious trees in the family Rutaceae, native to east and northeast Asia. It has leathery, pinnate leaves and yellow, clumped flowers. The name refers to the thick and corky bark of some species in the genus.

<span class="mw-page-title-main">Catechin</span> Type of natural phenol as a plant secondary metabolite

Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.

The University of Rochester Arboretum is an arboretum located across the River Campus of the University of Rochester, 612 Wilson Boulevard, Rochester, New York.

<i>Papilio protenor</i> Species of butterfly

Papilio protenor, the spangle, is a butterfly found in South East Asia belonging to the swallowtail family.

<i>Phellodendron amurense</i> Species of tree

Phellodendron amurense is a species of tree in the family Rutaceae, commonly called the Amur cork tree. It is a major source of huáng bò, one of the 50 fundamental herbs used in traditional Chinese medicine. The Ainu people used this plant, called shikerebe-ni, as a painkiller. It is known as hwangbyeok in Korean and (キハダ) kihada in Japanese.

<i>Scutellaria lateriflora</i> Species of flowering plant

Scutellaria lateriflora, is a hardy perennial herb of the mint family, Lamiaceae, native to North America.

<i>Styphnolobium japonicum</i> Species of legume

Styphnolobium japonicum, the Japanese pagoda tree is a species of deciduous tree in the subfamily Faboideae of the pea family Fabaceae.

<span class="mw-page-title-main">Anthocyanin</span> Class of plant-based pigments

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart named a chemical compound that gives flowers a blue color, Anthokyan, in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

Phenolic compounds—natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Vitexin</span> Chemical compound

Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus, in the Phyllostachys nigra bamboo leaves, in the pearl millet, and in Hawthorn.

<span class="mw-page-title-main">Flavanonol</span> Class of chemical compounds

The flavanonols are a class of flavonoids that use the 3-hydroxy-2,3-dihydro-2-phenylchromen-4-one backbone.

<span class="mw-page-title-main">Astilbin</span> Chemical compound

Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer.

<span class="mw-page-title-main">Phellamurin</span> Chemical compound

Phellamurin, a flavonoid, is the 7-O-β-D-glucopyranoside, 8-C-prenyl derivative of the flavan-on-ol Aromadendrin, and may be seen as the 7-O-glucoside of noricaritin. Being a flavanonol, it has two stereocenters on the C-ring, so four stereoisomers of phellamurin are possible.

<span class="mw-page-title-main">Sakuranin</span> Chemical compound

Sakuranin is a flavanone, a type of flavonoid. It is the O-glucoside of sakuranetin. It can be found in Prunus sp.

<span class="mw-page-title-main">Huang Bai</span> Herb in Chinese medicine

Huáng bǎi, huáng bó or huáng bò is one of the fifty fundamental herbs of traditional Chinese medicine. Known also as Cortex Phellodendri, it is the bark of one of two species of Phellodendron tree: Phellodendron amurense or Phellodendron chinense.

<span class="mw-page-title-main">Phellodendrine</span> Chemical compound

Phellodendrine is an alkaloid isolated originally from Phellodendron amurense (Rutaceae).

Kaempferol 7-<i>O</i>-glucoside Chemical compound

Kaempferol 7-O-glucoside is a flavonol glucoside. It can be found in Smilax china, and in the fern Asplenium rhizophyllum, and its hybrid descendants, as part of a complex with caffeic acid.

Amurensin may refer to:

<span class="mw-page-title-main">Ethyl caffeate</span> Chemical compound

Ethyl caffeate is an ester of a hydroxycinnamic acid, a naturally occurring organic compound.

<span class="mw-page-title-main">Veronicastroside</span> Chemical compound

Veronicastroside is a flavone, a type of flavonoid. It is the 7-O-neohesperidoside of luteolin. It can be found in Veronicastrum sibiricum var. japonicum and in Teucrium gnaphalodes.

References

  1. 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
  2. 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