Gingerol

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Gingerol
Gingerol
Identifiers
CAS number 23513-14-6 YesY
PubChem 442793
ChemSpider 391126 YesY
UNII 925QK2Z900 YesY
KEGG C10462 YesY
ChEMBL CHEMBL402978 YesY
Jmol-3D images Image 1
Properties
Molecular formula C17H26O4
Molar mass 294.38 g/mol
Melting point 30-32 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references
Gingerol
Heat (SR: 60,000)

Gingerol, or sometimes [6]-gingerol, is the active constituent of fresh ginger. Chemically, gingerol is a relative of capsaicin and piperine, the compounds which give chilli peppers and black pepper their respective spicyness.[1] It is normally found as a pungent yellow oil, but also can form a low-melting crystalline solid.

Cooking ginger transforms gingerol into zingerone, which is less pungent and has a spicy-sweet aroma. When ginger is dried, gingerol undergoes a dehydration reaction forming shogaols, which are about twice as pungent as gingerol. This explains why dried ginger is more pungent than fresh ginger.[1]

Physiological effects[edit]

[6]-Gingerol administered by intraperitoneal injection has been used to induce a hypothermic state in rats.[2]

Gingerol seems to be effective in an animal model of rheumatoid arthritis.[3]

Gingerol has been investigated for its effect on cancerous tumors in the bowel,[4][5] breast tissue,[6] ovaries,[7] the pancreas,[8] among other tissues, with positive results.

The product is sometimes used for gingering of horses, a practice that is seen in the horse show world, and which is illegal in some, but not all disciplines.[9]

References[edit]

  1. ^ a b McGee, Harold (2004). "A survey of tropical spices". McGee on Food and Cooking. Hodder and Stoughton. p. 426. ISBN 0-340-83149-9. 
  2. ^ Ueki, S; Miyoshi, M; Shido, O; Hasegawa, J; Watanabe, T (2008). "Systemic administration of [6]-gingerol, a pungent constituent of ginger, induces hypothermia in rats via an inhibitory effect on metabolic rate". European Journal of Pharmacology 584 (1): 87–92. doi:10.1016/j.ejphar.2008.01.031. PMID 18295202. 
  3. ^ Funk, Janet L.; Frye, Jennifer B.; Oyarzo, Janice N.; Timmermann, Barbara N. (2009). "Comparative Effects of Two Gingerol-Containing Zingiber officinale Extracts on Experimental Rheumatoid Arthritis". Journal of Natural Products 72 (3): 403–7. doi:10.1021/np8006183. PMC 2837120. PMID 19216559. 
  4. ^ "Ginger 'could halt bowel cancer'". BBC News. October 29, 2003. 
  5. ^ Jeong, C.-H.; Bode, A. M.; Pugliese, A.; Cho, Y.-Y.; Kim, H.-G.; Shim, J.-H.; Jeon, Y.-J.; Li, H. et al. (2009). "[6]-Gingerol Suppresses Colon Cancer Growth by Targeting Leukotriene A4 Hydrolase". Cancer Research 69 (13): 5584–91. doi:10.1158/0008-5472.CAN-09-0491. PMID 19531649. 
  6. ^ Lee, H; Seo, E; Kang, N; Kim, W (2008). "[6]-Gingerol inhibits metastasis of MDA-MB-231 human breast cancer cells". The Journal of Nutritional Biochemistry 19 (5): 313–9. doi:10.1016/j.jnutbio.2007.05.008. PMID 17683926. 
  7. ^ Rhode, Jennifer; Fogoros, Sarah; Zick, Suzanna; Wahl, Heather; Griffith, Kent A; Huang, Jennifer; Liu, J Rebecca (2007). "Ginger inhibits cell growth and modulates angiogenic factors in ovarian cancer cells". BMC Complementary and Alternative Medicine 7: 44. doi:10.1186/1472-6882-7-44. PMC 2241638. PMID 18096028. 
  8. ^ Park, Yon Jung; Wen, Jing; Bang, Seungmin; Park, Seung Woo; Song, Si Young (2006). "[6]-Gingerol Induces Cell Cycle Arrest and Cell Death of Mutant p53-expressing Pancreatic Cancer Cells". Yonsei Medical Journal 47 (5): 688–97. doi:10.3349/ymj.2006.47.5.688. PMC 2687755. PMID 17066513. 
  9. ^ "hermographic detection of gingering in horses" T.A. Turner DVM, MS1 and R.D. Scoggins DVM, Journal of Equine Veterinary Science Volume 5, Issue 1, 1985, Pages 8-10