6-shogaol

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Structural formula
Structural formula of 6-shogaol
General
Surname 6-shogaol
other names

( E ) -1- (4-Hydroxy-3-methoxyphenyl) -4-decen-3-one

Molecular formula C 17 H 24 O 3
Brief description

viscous, yellow liquid

External identifiers / databases
CAS number 555-66-8
EC number 664-006-0
ECHA InfoCard 100.190.262
PubChem 5281794
ChemSpider 4445106
Wikidata Q2746448
properties
Molar mass 276.37 g mol −1
Physical state

liquid

density

1.033 g cm −3

boiling point

427.5 ° C (1013.25 hPa)

solubility

soluble in methanol and ethanol

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: ?
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

6-Shogaol (derived from Japanese 生姜 、shōga , ginger) is a natural ingredient of the ginger rhizome ( Zingiber officinale ). In addition to 6- gingerol, the compound is primarily responsible for the pungent taste of ginger. The first extraction was achieved in 1918 by H. Nomura by distilling the rhizome oil, the first correct proposal for the structural formula came from Nomura and Tsurumi in 1927.

Of particular medical interest are the diverse potentially health-promoting effects of 6-shogaol, which is why the compound is the subject of current research.

Occurrence

6-Shogaol occurs naturally in the rhizome of ginger ( Zingiber officinale ).

In addition to the derivatives 4-, 8-, 10- and 12-Shogaol, 6-Shogaol occurs in low concentrations of up to 2.3 mg / g in the undried rootstock of ginger. However, the concentration of the compound is far higher in dried ginger. The proportion of 6-Shogaol in ginger can be increased by boiling, steaming or briefly frying.

The compound with 6-gingerol, a substance that can also be found in ginger rhizome, is chemically very similar. The shogaol molecule corresponds to a gingerol molecule that is dehydrated in the α-β position to the keto group and is created from this when ginger is dried.

Analytics

The extraction of 6-shogaol is usually carried out from dried ginger with an organic solvent such as ethanol . The amount of 6-shogaol in the extract can be increased by performing the extraction at a low pH and heating the ethanol to 80 ° C. The remaining 6-gingerol can with BMIM - bisulfate under irradiation with ultrasonic mostly in the desired 6-Shogaol be converted. The further purification is usually carried out by chromatography using methods such as HPLC , UHPLC and HSCCC .

synthesis

A synthesis of 6-shogaol is possible based on a Claisen-Schmidt condensation of vanillin with acetone to form dehydrozingerone . A subsequent cross-aldol condensation with hexanal in tetrahydrofuran produces 6-dehydroshogaol and 6-dehydrogingerol. The latter is catalytically hydrogenated to 6-gingerol , from which 6-shogaol can be produced by adding hydrochloric acid .

Synthesis route for 6-shogaol starting from vanillin.

Physiological effects

With a value of 160,000 Scoville , 6-Shogaol is about three times hotter than 6-Gingerol, but significantly milder than pure capsaicin .

Several studies have reported various effects of 6-shogaol, suggesting different potential uses as a drug. In particular, the use of 6-Shogaol in the treatment of tumors is the subject of current research: according to these reports, the compound partially inhibited the spread of gastrointestinal tumors, prostate and breast cancer cells both in vitro and in vivo , among other things via inactivation the NF-kB - transcription factor or regulate the activity of MMP prevent -9 enzyme. 6-Shogaol selectively triggered programmed cell death in cancer cells through apoptosis , which was induced by the production of reactive oxygen species and, in particular, by activation of the enzyme caspase .

Another study found that the progression of Alzheimer's disease was slower . A potentially protective effect on cholinergic neurons could also be determined by the connection. The dysfunction and death of such neurons is seen as the cause of memory problems in Alzheimer's. Another study came to the result that 6-shogaol is the strongest antioxidant and the strongest anti-inflammatory substance of all the gingerols and derivatives examined , which the research group attributed to the keto group, which is unsaturated in the α, β position . Like 6-gingerol, shogaol is an inhibitor of blood vessel proliferation in smooth muscle tissue .

Clinical studies on the effects of 6-shogaol in humans do not yet exist. In contrast, many websites try to advertise the supposed positive effects of ginger against a wide variety of diseases.

Web links

  • Overview page of studies relating to 6-shogaol

Individual evidence

  1. ↑ a b 6-Shogaol. In: aphios.com. Retrieved March 18, 2018 .
  2. ↑ Safety data sheet . (PDF) Santa Cruz Biotechnology Inc, January 22, 2015, p. 3 , accessed March 17, 2018 .
  3. ↑ a b 6-Shogaol. In: alfa-chemistry.com. Retrieved March 17, 2018 .
  4. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label of [No public or meaningful name is available] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on April 8, 2018, is reproduced from a self-classification by the distributor .
  5. ↑ a b Mamoru Suekawa et al .: Pharmacological studies on ginger. I. Pharmacological actions of pungent constituents, (6) -Gingerol and (6) -Shogaol . In: Journal of Pharmacobio-Dynamics . tape 7 , no. 11 , 1984, pp. 836 , PMID 6335723 .
  6. ↑ R. Hegnauer: Chemotaxonomy of plants . An overview of the distribution and the systematic importance of plant substances. tape 16 . Springer, 2013, ISBN 978-3-0348-9387-9 , pp. 464 ( limited preview in Google Book search).
  7. ↑ Lee S. et al .: Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract . In: Journal of AOAC International . tape 90 , no. 5 , September 2007, pp. 1219-1226 , PMID 17955965 .
  8. ↑ Masami Yoshida, Saori Harabayashi: Changes in 6-Gingerol Concentration in Ginger under Various Types of Cooking Conditions . In: Journal of Cookery Science of Japan . tape 48 , no. 6 , 2015, p. 398-404 , doi : 10.11402 / cookeryscience.48.398 .
  9. ↑ a b V. A. Parthasarathy, B. Chempakam, TJ Zachariah: Chemistry of Spices . CAB International, 2008, ISBN 978-1-84593-405-7 , pp. 84 ( limited preview in Google Book search).
  10. ↑ Seon Ok, Woo-Sik Jeong: Optimization of Extraction Conditions for the 6-Shogaol-rich Extract from Ginger (Zingiber officinale Roscoe) . In: Preventive Nutrition and Food Science . tape 17 , no. 2 , June 2012, p. 166-171 , PMC 3866747 (free full text).
  11. ↑ Xingran Kou et al .: Efficient dehydration of 6-gingerol to 6-shogaol catalyzed by an acidic ionic liquid under ultrasound irradiation . In: Food chemistry . tape 215 , January 15, 2017, p. 193-199 , PMID 27542467 .
  12. ^ Su Yeon Park, Mun Yhung Jung: UHPLC-ESI-MS / MS for the Quantification of Eight Major Gingerols and Shogaols in Ginger Products: Effects of Ionization Polarity and Mobile Phase Modifier on the Sensitivity . In: Journal of Food Science . tape 81 , no. October 10 , 2016, PMID 27589022 .
  13. ↑ Qingliang Qiao, Qizhen Du: Preparation of the monomers of gingerols and 6-shogaol by flash high speed counter-current chromatography . In: Journal of Chromatography A . tape 1218 , no. 36 , September 9, 2011, p. 6187-6190 , PMID 21195411 .
  14. ↑ Hung-Cheng Shih et al .: Synthesis of Analogues of Gingerol and Shogaol, the Active Pungent Principles from the Rhizomes of Zingiber officinale and Evaluation of Their Anti-Platelet Aggregation Effects . In: International Journal of Molecular Sciences . tape 15 , no. 3 , March 2014, p. 3926-3951 , PMC 3975376 (free full text).
  15. ↑ 6-Shogaol. In: ginger-ffekt.info. Retrieved March 16, 2018 .
  16. ^ Ginger and Its Constituents: Role in Prevention and Treatment of Gastrointestinal Cancer . In: Gastroenterology Research and Practice . May 8, 2015, PMC 4369959 (free full text).
  17. ↑ Achinto Saha et al .: 6-Shogaol from dried ginger inhibits growth of prostate cancer cells both in vitro and in vivo through inhibition of STAT3 and NF-κB signaling . In: Cancer Prevention Research . tape 7 , no. June 6 , 2014, PMID 24691500 .
  18. ↑ H. Ling et al .: 6-Shogaol, an active constituent of ginger, inhibits breast cancer cell invasion by reducing matrix metalloproteinase-9 expression via blockade of nuclear factor-κB activation . In: British Journal of Pharmacology . tape 161 , no. 1 , December 2010, p. 1763–1777 , PMC 3010581 (free full text).
  19. ↑ Min-Hsiung Pan et al .: 6-Shogaol induces apoptosis in human colorectal carcinoma cells via ROS production, caspase activation, and GADD 153 expression . In: Molecular Nutrition Food Research . April 2, 2008, PMID 18384088 .
  20. ↑ Kishora R. Sakharkar: Post-genomic Approaches in Cancer and Nano Medicine . River Publishers, 2015, ISBN 978-87-93102-86-6 , 5.5.18, pp. 139–142 ( limited preview in Google Book search).
  21. ↑ Ji-Young Na et al .: 6-Shogaol has anti-amyloidogenic activity and ameliorates Alzheimer's disease via CysLT1R-mediated inhibition of cathepsin B . In: Biochemical and Biophysical Research Communications . tape 477 , no. 1 , August 12, 2016, p. 96-102 , PMID 27286707 .
  22. ↑ Sehwan Shim, Jungkee Kwon: Effects of [6] -shogaol on cholinergic signaling in HT22 cells following neuronal damage induced by hydrogen peroxide . In: Food and Chemical Toxicology . tape 50 , no. 5 , p. 1454-1459 , PMID 22381256 .
  23. ↑ Swarnalatha Dugasani et al .: Comparative antioxidant and anti-inflammatory effects of [6] -gingerol, [8] -gingerol, [10] -gingerol and [6] -shogaol . In: Journal of Ethnopharmacology . tape 127 , no. 2 , February 3, 2010, p. 515-520 , PMID 19833188 .
  24. ↑ Rongxia Liu et al .: Identification and characterization of [6] -shogaol from ginger as inhibitor of vascular smooth muscle cell proliferation . In: Molecular Nutrition & Food Research . tape 59 , no. 5 , May 2015, p. 843-852 , PMC 4573514 (free full text).
  25. ↑ J. Harlfinger: Ginger against breast cancer: False hopes. In: Medizin-transparent.at. October 12, 2016, accessed March 17, 2018 .
  26. ↑ Linda Weißer: The five most common mistakes when it comes to nutrition. In: alimonia.net. September 17, 2017. Retrieved March 18, 2018 .