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
491-70-3 YesY
ChEBI CHEBI:15864 N
ChEMBL ChEMBL151 N
ChemSpider 4444102 N
5215
Jmol-3D images Image
PubChem 5280445
UNII KUX1ZNC9J2 N
Properties
C15H10O6
Molar mass 286.24 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 isYesY/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]

Pharmacology[edit]

In vitro, luteolin activates the dopamine transporter.[6][7] Luteolin is under other 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.[8] Luteolin has also been found to have adverse effects in laboratory studies with endometrial cancer cells by blocking endocrine effects of the hormone progesterone.[9]

Metabolism[edit]

These enzymes are part of luteolin metabolism:[citation needed]

Glycosides[edit]

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. ^ Zhao G, Qin GW, Wang J, Chu WJ, Guo LH (2010). "Functional activation of monoamine transporters by luteolin and apigenin isolated from the fruit of Perilla frutescens (L.) Britt". Neurochem. Int. 56 (1): 168–76. doi:10.1016/j.neuint.2009.09.015. PMID 19815045. 
  7. ^ Zhang J, Liu X, Lei X et al. (2010). "Discovery and synthesis of novel luteolin derivatives as DAT agonists". Bioorg. Med. Chem. 18 (22): 7842–8. doi:10.1016/j.bmc.2010.09.049. PMID 20971650. 
  8. ^ 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
  9. ^ "Common Autism Supplement Affects Endocrine System". Science Daily. July 15, 2013. Retrieved 2 September 2013. 
  10. ^ 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.