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 has been studied in several preliminary laboratory investigations, indicating potential for antioxidant activity (i.e. scavenging of free radicals), promotion of carbohydrate metabolism, immune system modulation and type 2 diabetes, among other clinical indications under study.[4][7][8][9] The therapeutic value of these studies is unclear, and will remain so until further detailed in vivo, toxicity and human clinical studies are completed to establish significant scientific agreement about its effects.

Adverse effects[edit]

Gastrointestinal adverse effects, such as nausea, vomiting, and gastric hypersecretion, may occur, as shown in one animal study.[10] Luteolin has also been found to have adverse effects in laboratory studies with endometrial cancer cells by blocking endocrine effects of the hormone progesterone.[11]

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. ^ a b 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. ^ Johnson; Kelley, KW; Johnson, RW (May 2008). "Luteolin reduces IL-6 production in microglia by inhibiting JNK phosphorylation and activation of AP-1". Proc. Natl. Acad. Sci. U.S.A. 105 (21): 7534–9. doi:10.1073/pnas.0802865105. PMC 2396685. PMID 18490655. 
  8. ^ Theoharides (2009). "Luteolin as a Therapeutic Option for Multiple Sclerosis". Journal of Neuroinflammation 6 (1): 29. doi:10.1186/1742-2094-6-29. PMC 2768692. PMID 19825165. 
  9. ^ Wang, L; Waltenberger, B; Pferschy-Wenzig, E. M.; Blunder, M; Liu, X; Malainer, C; Blazevic, T; Schwaiger, S; Rollinger, J. M.; Heiss, E. H.; Schuster, D; Kopp, B; Bauer, R; Stuppner, H; Dirsch, V. M.; Atanasov, A. G. (2014). "Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): A review". Biochemical pharmacology. doi:10.1016/j.bcp.2014.07.018. PMID 25083916.  edit
  10. ^ 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. doi:10.1016/j.ejphar.2009.10.031. PMID 19853596.  edit
  11. ^ "Common Autism Supplement Affects Endocrine System". Science Daily. July 15, 2013. Retrieved 2 September 2013.