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Luteolin

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Luteolin
The chemical structure of luteolin
Ball-and-stick model of Luteolin
Names
IUPAC name
2-(3,4-Dihydroxyphenyl)- 5,7-dihydroxy-4-chromenone
Other names
Luteolol
Digitoflavone
Flacitran
Luteoline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.038 Edit this at Wikidata
UNII
  • InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H ☒N
    Key: IQPNAANSBPBGFQ-UHFFFAOYSA-N ☒N
  • InChI=1/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
    Key: IQPNAANSBPBGFQ-UHFFFAOYAY
  • C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
Properties
C15H10O6
Molar mass 286.239 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Luteolin is a flavone, a type of flavonoid. Like all flavonoids, it has a yellow crystalline appearance.[1]

Natural occurrences

Luteolin is most often found in leaves, but it is also seen in rinds, barks, clover blossom, and ragweed pollen.[1] It has also been isolated from the aromatic flowering plant, Salvia tomentosa in the mint family, Lamiaceae.[2]

Dietary sources include celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano.[3][4] It can also be found in the seeds of the palm Aiphanes aculeata.[5]

References

  1. ^ a b Mann, John (1992). Secondary Metabolism (2nd ed.). Oxford, UK: Oxford University Press. pp. 279–280. ISBN 0-19-855529-6.
  2. ^ A. Ulubelen, M. Miski, P. Neuman, and T. J. Mabry (1979). "Flavonoids of Salvia tomentosa (Labiatae)". Journal of Natural Products. 42 (4): 261–3. doi:10.1021/np50003a002.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Kayoko Shimoi, Hisae Okada, Michiyo Furugori, Toshinao Goda, Sachiko Takase, Masayuki Suzuki, Yukihiko Hara, Hiroyo Yamamoto, Naohide Kinae (1998). "Intestinal absorption of luteolin and luteolin 7-O-[beta]-glucoside in rats and humans". FEBS Letters. 438 (3): 220–4. doi:10.1016/S0014-5793(98)01304-0. PMID 9827549.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ López-Lázaro M. (2009). "Distribution and biological activities of the flavonoid luteolin". Mini Rev Med Chem. 9 (1): 31–59. doi:10.2174/138955709787001712. PMID 19149659.
  5. ^ Lee, D; Cuendet, M; Vigo, JS; Graham, JG; Cabieses, F; Fong, HH; Pezzuto, JM; Kinghorn, AD (2001). "A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata". Organic Letters. 3 (14): 2169–71. doi:10.1021/ol015985j. PMID 11440571.