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
ChEBI CHEBI:10136 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]

Ginger also contains 8-gingerol, 10-gingerol,[2] and 12-gingerol.[3]

Physiological effects[edit]

[6]-Gingerol administered by intraperitoneal injection has been used to induce a hypothermic state in rats.[4]

Gingerol seems to be effective in an animal model of rheumatoid arthritis.[5]

Gingerol has been investigated for its effect on cancerous tumors in the bowel,[6][7] breast tissue,[8] ovaries,[9] the pancreas,[10] 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.[11]

Biosynthesis[edit]

Proposed gingerol biosynthesis

Both ginger (Zingiber officinale) and turmeric (Curcuma longa) had been suspected to utilize phenylpropanoid pathway and produce putative type III polyketide synthase products based on the research of 6-gingerol biosynthesis by Denniff and Whiting in 1976 [12] and by Schröder's research in 1997.[13] 6-Gingerol is the major gingerol in ginger rhizomes and it possesses some interesting pharmacological activities like analgesic effect. While the biosynthesis of 6-gingerol is not fully elucidated, plausible pathways are presented here.

Alternative proposed pathway


In the proposed biosynthetic pathway, Scheme 1, L-Phe (1) is used as the starting material. It is converted into Cinnamic acid (2) via phenylalanine ammonia lyase (PAL). Then it is turned into p-Coumaric acid (3) with use of cinnamate 4-hydroxylase (C4H). 4-coumarate:CoA ligase (4CL) is then used to get p-Coumaroyl-CoA (5). P-Coumaroyl shikimate transferase (CST) is the enzyme that is responsible for the bonding of shikimic acid and p-Coumaroyl-CoA. The complexed (5) is then selectively oxidized at C3 by p-coumaroyl 5-O-shikimate 3'-hydroxylase (CS3'H) to alcohol. With another action of CST, shikimate is broken off from this intermediate, thereby yielding Caffeoyl-CoA (7). In order to get desired substitution pattern on the aromatic ring, caffeoyl-CoA O-methyltransferase (CCOMT) converts the hydroxyl group at C3 into methoxy as seen in Feruloyl-CoA (8). Up until this step, according to Ramirez-Ahumada et. al., the enzyme activities are very active.[14] It is speculated that some polyketide synthases (PKS) and reductases are involved in final synthesis of 6-Gingerol (10).

Because it is unclear whether the methoxy group addition is performed prior or post to condensation step of the polyketide synthase, alternative pathway is shown in Scheme 2, where methoxy group is introduced after PKS activity. In this alternative pathway, the enzymes involved are likely be cytochrome p450 hydroxylases, and S-adenosyl-L-methionine-dependent O-methyltransferases (OMT).[14] There are three possibilities for the reduction step by Reductase: directly after PKS activity, after PKS and Hydroxylase activity, or in the end after PKS, Hydroxylase, and OMT activity.

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. ^ http://www.ncbi.nlm.nih.gov/pubmed/18708382
  3. ^ http://www.ncbi.nlm.nih.gov/pubmed/18814211
  4. ^ 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. 
  5. ^ 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. 
  6. ^ "Ginger 'could halt bowel cancer'". BBC News. October 29, 2003. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ 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. 
  11. ^ "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
  12. ^ Denniff, Phillip; Whiting, Donald A. "Biosynthesis of [6]-gingerol, pungent principle of Zingiber officinale". Journal of the Chemical Society, Chemical Communications (18): 711. doi:10.1039/C39760000711. 
  13. ^ Schröder, Joachim. "A family of plant-specific polyketide synthases: facts and predictions". Trends in Plant Science 2 (10): 373–378. doi:10.1016/S1360-1385(97)87121-X. 
  14. ^ a b Ramirez-Ahumada, Maria del Carmen; Timmermann, Barbara N.; Gang, David R. "Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): Identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases". Phytochemistry 67 (18): 2017–2029. doi:10.1016/j.phytochem.2006.06.028.