Kaempferol 7-O-glucoside

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Kaempferol 7-O-glucoside
Kaempferol 7-O-glucoside.svg
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxyflavone
Preferred IUPAC name
3,5-Dihydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Kaempferol-7-O-beta-D-glucoside
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21-/m1/s1
    Key: YPWHZCPMOQGCDQ-HMGRVEAOSA-N
  • InChI=1/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21-/m1/s1
    Key: YPWHZCPMOQGCDQ-HMGRVEAOBK
  • C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
Properties
C21H20O11
Molar mass 448.380 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Kaempferol 7-O-glucoside is a flavonol glucoside. It can be found in Smilax china , [1] and in the fern Asplenium rhizophyllum , and its hybrid descendants, as part of a complex with caffeic acid. [2]

Derivatives

Amurensin is the tert-amyl alcohol derivative of kaempferol 7-O-glucoside. 6'''-O-acetyl amurensin is found in the leaves of Phellodendron japonicum . [3]

Related Research Articles

<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 kihada in Japanese.

Piceid Chemical compound

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of Picea sitchensis. It can also be isolated from Reynoutria japonica, the Japanese knotweed.

Icariin Chemical compound

Icariin is a chemical compound classified as a prenylated flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-O-diglucoside. The compound has been isolated from several species of plant belonging to the genus Epimedium which are commonly known as horny goat weed, Yin Yang Huo, and Herba epimedii. Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function. However, clinical trial data are lacking to support these claims.

Vitexin 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.

Trifolin Chemical compound

Trifolin is a chemical compound. It is the kaempferol 3-galactoside. It can be found in Camptotheca acuminata, in Euphorbia condylocarpa or in Consolida oliveriana.

Flavanonol

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

Taxifolin Chemical compound

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols.

Phellamurin 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.

Amurensin (flavonol) Chemical compound

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.

<i>Asplenium montanum</i> Species of fern in the family Aspleniaceae

Asplenium montanum, commonly known as the mountain spleenwort, is a small fern endemic to the eastern United States. It is found primarily in the Appalachian Mountains from Vermont to Alabama, with a few isolated populations in the Ozarks and in the Ohio Valley. It grows in small crevices in sandstone cliffs with highly acid soil, where it is usually the only vascular plant occupying that ecological niche. It can be recognized by its tufts of dark blue-green, highly divided leaves. The species was first described in 1810 by the botanist Carl Ludwig Willdenow. No subspecies have been described, although a discolored and highly dissected form was reported from the Shawangunk Mountains in 1974. Asplenium montanum is a diploid member of the "Appalachian Asplenium complex," a group of spleenwort species and hybrids which have formed by reticulate evolution. Members of the complex descended from A. montanum are among the few other vascular plants that can tolerate its typical habitat.

Huang Bai Herb in Chinese medicine

Huáng bǎi, huáng bó (黃柏) or huáng bò (黃檗) 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.

Palmatine Chemical compound

Palmatine is a protoberberine alkaloid found in several plants including Phellodendron amurense, Coptis Chinensis(Rhizoma coptidis,

Mangiferin Chemical compound

Mangiferin is a xanthonoid. This molecule is a glucoside of norathyriol.

Gastrodin Chemical compound

Gastrodin is a chemical compound which is the glucoside of gastrodigenin. It has been isolated from the orchid Gastrodia elata and from the rhizome of Galeola faberi. It can also be produced by biotransformation of 4-hydroxybenzaldehyde by Datura tatula cell cultures.

Cucurbitane Chemical compound

Cucurbitane is a class of chemical compounds with formula C
30
H
54
. There are a polycyclic hydrocarbon, specifically triterpene. There are isomers of lanostane, from which it differs by the formal shift of a methyl group from the 10 to the 9β position in the standard steroid numbering scheme.

<i>Pteris ensiformis</i> Species of fern

Pteris ensiformis, the slender brake, silver lace fern, sword brake fern, or slender brake fern, is a plant species of the genus Pteris in the family Pteridaceae. It is found in Asia and the Pacific.

<i>Smilax china</i> Species of flowering plant

Smilax china is a climbing plant species in the genus Smilax. It is native to China, Korea, Taiwan, Japan, Philippines, Vietnam, Thailand, Myanmar, and Assam. Common names for the plant include China root.

Liquiritin Chemical compound

Liquiritin is the 4'-O-glucoside of the flavanone liquiritigenin. Liquiritin is one of flavone compounds derived from licorice.

Chrysophanol Chemical compound

Chrysophanol, also known as chrysophanic acid, is a fungal isolate and a natural anthraquinone. It is a C-3 methyl substituted chrysazin of the trihydroxyanthraquinone family.

Tropoflavin

7,8-Dihydroxyflavone is a naturally occurring flavone found in Godmania aesculifolia, Tridax procumbens, and primula tree leaves. It has been found to act as a potent and selective small-molecule agonist of the tropomyosin receptor kinase B (TrkB), the main signaling receptor of the neurotrophin brain-derived neurotrophic factor (BDNF). 7,8-DHF is both orally bioavailable and able to penetrate the blood–brain barrier. A prodrug of 7,8-DHF with greatly improved potency and pharmacokinetics, R13, is under development for the treatment of Alzheimer's disease.

References

  1. Xu, W.; Liu, J.; Li, C.; Wu, H. Z.; Liu, Y. W. (2008). "Kaempferol-7-O-β-d-glucoside (KG) isolated from Smilax china L. rhizome induces G2/M phase arrest and apoptosis on HeLa cells in a p53-independent manner". Cancer Letters. 264 (2): 229–240. doi:10.1016/j.canlet.2008.01.044. PMID   18343026.
  2. Harborne, Jeffrey B.; Williams, Christine A.; Smith, Dale M. (1973). "Species-specific kaempferol derivatives in ferns of the Appalachian Asplenium complex". Biochemical Systematics and Ecology. 1 (1): 51–54. doi:10.1016/0305-1978(73)90035-5.
  3. Chiu, C. Y.; Li, C. Y.; Chiu, C. C.; Niwa, M.; Kitanaka, S.; Damu, A. G.; Lee, E. J.; Wu, T. S. (2005). "Constituents of Leaves of Phellodendron japonicum MAXIM. And Their Antioxidant Activity". Chemical & Pharmaceutical Bulletin. 53 (9): 1118. doi: 10.1248/cpb.53.1118 .