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Aspalathin

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Aspalathin
Names
IUPAC name
3-(3,4-Dihydroxyphenyl)-1-[5-(β-D-glucopyranosyl)-2,4-dihydroxyphenyl]propan-1-one
Systematic 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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.233.299 Edit this at Wikidata
  • 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 ☒N
    Key: VCPUQYKWJRESOC-VJXVFPJBSA-N ☒N
  • 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).
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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]

References

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  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. 50 (20). Elsevier: 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. doi:10.1042/bj0990604. 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. Bibcode:2019PLoSO..1416172M. doi:10.1371/journal.pone.0216172. ISSN 1932-6203. PMC 6497260. PMID 31048842.
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