Luteolin

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Luteolin
The chemical structure of luteolin
Identifiers
CAS number 491-70-3 YesY
PubChem 5280445
ChemSpider 4444102 N
UNII KUX1ZNC9J2 N
ChEBI CHEBI:15864 N
ChEMBL CHEMBL151 N
Jmol-3D images Image 1
Properties
Molecular formula C15H10O6
Molar mass 286.24 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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

Natural occurrences[edit]

Luteolin can be found in Terminalia chebula. It 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 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]

Metabolism[edit]

These enzymes are part of luteolin metabolism:

Glycosides[edit]

Biomedical research[edit]

Luteolin is under preliminary laboratory research, but there is no evidence to date about its effects in humans.

Adverse effects[edit]

Gastrointestinal adverse effects, such as nausea, vomiting, and gastric hypersecretion, may occur, as shown in one animal study.[7] Luteolin has also been found to have adverse effects in laboratory studies with endometrial cancer cells by blocking endocrine effects of the hormone progesterone.[8]

References[edit]

  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. 
  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. 
  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. 
  6. ^ Capanlar, S; Böke, N; Yaşa, I; Kirmizigül, S (2010). "A novel glycoside from Acanthus hirsutus (Acanthaceae)". Natural product communications 5 (4): 563–6. PMID 20433073. 
  7. ^ Yu, M. C.; Chen, J. H.; Lai, C. Y.; Han, C. Y.; Ko, W. C. (2010). "Luteolin, a non-selective competitive inhibitor of phosphodiesterases 1–5, displaced [3H]-rolipram from high-affinity rolipram binding sites and reversed xylazine/ketamine-induced anesthesia". European Journal of Pharmacology 627 (1–3): 269–75. doi:10.1016/j.ejphar.2009.10.031. PMID 19853596.  edit
  8. ^ "Common Autism Supplement Affects Endocrine System". Science Daily. July 15, 2013. Retrieved 2 September 2013.