Aspalathin

Last updated
Aspalathin
Aspalathin structure.svg
Names
IUPAC name
3-(3,4-Dihydroxyphenyl)-1-[5-β-D-glucopyranosyl-2,4-dihydroxyphenyl]propan-1-one
Preferred IUPAC name
3-(3,4-Dihydroxyphenyl)-1-{2,4-dihydroxy-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl}propan-1-one
Identifiers
  • 6027-43-6 Yes check.svgY
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.233.299 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/C21H24O11/c22-7-14-17(28)19(30)20(31)21(32-14)16-13(27)6-12(26)15(18(16)29)10(24)4-2-8-1-3-9(23)11(25)5-8/h1,3,5-6,14,17,19-23,25-31H,2,4,7H2/t14-,17-,19+,20-,21+/m1/s1 X mark.svgN
    Key: VCPUQYKWJRESOC-VJXVFPJBSA-N X mark.svgN
  • InChI=1/C21H24O11/c22-7-14-17(28)19(30)20(31)21(32-14)16-13(27)6-12(26)15(18(16)29)10(24)4-2-8-1-3-9(23)11(25)5-8/h1,3,5-6,14,17,19-23,25-31H,2,4,7H2/t14-,17-,19+,20-,21+/m1/s1
    Key: VCPUQYKWJRESOC-VJXVFPJBBW
  • O=C(c1c(O)c(c(O)cc1O)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)CCc3ccc(O)c(O)c3
Properties
C21H24O11
Molar mass 452.412 g·mol−1
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 ?)
Infobox references

Aspalathin is a C-linked dihydrochalcone glucoside found in rooibos tea, a herbal tea prepared from the South African rooibos plant, Aspalathus linearis (Fabaceae). [1]

It was first isolated in 1965 by chromatography [2]

It has demonstrated antidiabetic activity. [3]

Related Research Articles

Herbal tea Beverage made from infusing or decocting plant material in hot water

Herbal teas—less commonly called tisanes —are beverages made from the infusion or decoction of herbs, spices, or other plant material in hot water. The term "herbal tea" is often used in contrast to true teas, which are prepared from the cured leaves of the tea plant, Camellia sinensis. Unlike coffee and true teas, most tisanes do not naturally contain caffeine.

Rooibos Species of plant, Rooibos

Rooibos, meaning "red bush"; is a broom-like member of the plant family Fabaceae that grows in South Africa's fynbos.

Safranal Chemical compound

Safranal is an organic compound isolated from saffron, the spice consisting of the stigmas of crocus flowers. It is the constituent primarily responsible for the aroma of saffron.

Kaempferol Chemical compound

Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach and broccoli. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.

<i>Nothofagus fusca</i> Species of tree

Nothofagus fusca, commonly known as red beech is a species of southern beech, endemic to New Zealand, where it occurs on both the North Island and South Island. Generally it is found on lower hills and inland valley floors where soil is fertile and well drained. In New Zealand the species is called Fuscospora fusca.

Deoxyribonuclease IV (phage-T4-induced) is a kind of Endonuclease that catalyzes the degradation nucleotides in DsDNA by attacking the 5'-terminal end.

TEAD2

TEAD2, together with TEAD1, defines a novel family of transcription factors, the TEAD family, highly conserved through evolution. TEAD proteins were notably found in Drosophila (Scalloped), C. elegans, S. cerevisiae and A. nidulans. TEAD2 has been less studied than TEAD1 but a few studies revealed its role during development.

TEAD1

Transcriptional enhancer factor TEF-1 also known as TEA domain family member 1 (TEAD1) and transcription factor 13 (TCF-13) is a protein that in humans is encoded by the TEAD1 gene. TEAD1 was the first member of the TEAD family of transcription factors to be identified.

SOX11

Transcription factor SOX-11 is a protein that in humans is encoded by the SOX11 gene.

Nothofagin Chemical compound

Nothofagin is a dihydrochalcone. It is a C-linked phloretin glucoside found in rooibos and New Zealand red beech. It is a phenolic antioxidant.

<i>tert</i>-Amyl alcohol Chemical compound

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

<i>Aspalathus</i> Genus of legumes

Aspalathus is a genus of flowering plants in the legume family, Fabaceae. The yellow flowers and spiny habit of some species have suggested a resemblance to Ulex europaeus, the thorny "English gorse" Accordingly, "Cape Gorse" has been proposed as a common name although the resemblance is largely superficial; for instance, gorse is thorny, whereas Aspalathus species are variously spiny or unarmed. The genus belongs to the subfamily Faboideae. There are over 270 species, mainly endemic to southwestern fynbos regions in South Africa, with over fifty occurring on the Cape Peninsula alone. The species Aspalathus linearis is commercially important, being farmed as the source of Rooibos tea.

Dihydrochalcone Chemical compound

Dihydrochalcone (DHC) is a chemical compound related to chalcone.

Epicatechin gallate Chemical compound

Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea. It is also reported in buckwheat and in grape.

Monopetalotaxis candescens is a moth of the family Sesiidae. It is known from South Africa.

Monopetalotaxis doleriformis is a moth of the family Sesiidae. It is known from South Africa.

3C-like protease

The 3C-like protease (3CLpro) or Mpro, formally known as C30 Endopeptidase, is the main protease found in coronaviruses. It cleaves the coronavirus polyprotein at eleven conserved sites. It is a cysteine protease and a member of the PA clan of proteases. It has a cysteine-histidine catalytic dyad at its active site and cleaves a Gln–(Ser/Ala/Gly) peptide bond.

2,4,5-Trihydroxycinnamic acid Chemical compound

2,4,5-Trihydroxycinnamic acid is a hydroxycinnamic acid found in rooibos tea. cis-2,4,5-Trihydroxycinnamic acid can be isolated from seeds of Alisma orientale.

Rooibos wine is a variety of wine in which wood from the rooibos and honeybush plants is used instead of the traditional oak wood during the maturation phase. It has its origin in the Western Cape, South Africa. The wine has a unique flavor component and due to the anti-oxidative effect of the plants can be produced without the use of sulfur dioxide.

Amanda Cecilia Swart is a South African biochemist who holds a professorship in biochemistry at Stellenbosch University. She is known for her research on rooibos, a herbal tea popular in South Africa, has been funded by the South African Rooibos Council in her research, and is frequently quoted in South African media promoting the reported health benefits of rooibos.

References

  1. Bramati L; et al. (2002). "Quantitative Characterization of Flavonoid Compounds in Rooibos Tea (Aspalathus linearis) by LC-UV/DAD". Journal of Agricultural and Food Chemistry. Elsevier. 50 (20): 5513–5519. doi:10.1021/jf025697h. PMID   12236672.
  2. Koeppen, B. H.; Roux, D. G. (June 1966). "C-Glycosylflavonoids. The chemistry of aspalathin". Biochemical Journal. 99 (3): 604–609. ISSN   0264-6021. PMC   1265048 . PMID   4290475.
  3. Bader, Michael; Mazibuko-Mbeje, Sithandiwe E.; Dludla, Phiwayinkosi V.; Johnson, Rabia; Joubert, Elizabeth; Louw, Johan; Ziqubu, Khanyisani; Tiano, Luca; Silvestri, Sonia; Orlando, Patrick; Opoku, Andy R.; Muller, Christo J. F. (2019). "Aspalathin, a natural product with the potential to reverse hepatic insulin resistance by improving energy metabolism and mitochondrial respiration". PLOS ONE. 14 (5): e0216172. doi:10.1371/journal.pone.0216172. ISSN   1932-6203. PMC   6497260 . PMID   31048842.