Chemical Properties
White crystalline powder. B.P. higher than 300℃. Very slightly soluble in water, soluble in alcohol and oils.
Uses
[6]-Shogaol is an aromatic constituent of ginger and the chain-dehydroxylated analog of [6]-Gingerol. [6]-Shogaol has activity very similar to [6]-Gingerol and produced an inhibition of spontaneous motor activity, antipyretic and analgesic effects, and prolonged hexobarbital-induced sleeping time. [6]-Shogaol also has potent antitussive activity and affected the cortical EEG.
Application
Shogaol has little or no application in perfumery, and very little interest to the flavor industry, but it is included in this work mainly for the purpose of elucidating the problems apparently existing around the description of the odorand flavor of "Zingerone".
Definition
ChEBI: [6]-Shogaol is a monomethoxybenzene, a member of phenols and an enone.
Preparation
6-Shogaol is prepared by condensation of Vanillin with Acetone, followed by hydrogenation. The resulting ketone is then condensed with Hexaldehyde under conditions which inactivate the hydroxyl group during the reaction.
Biological Activity
Shogaols exhibits higher potencyefficacyand biological activities than gingerols. It is an excellent antioxidant agentth at protects human primary epidermal melanocytes against oxidative stress by activating nuclear factor E2-related factor (Nrf2)-antioxidant response. Shogaol also displays antimicrobialantifungaland anti-biofilm activities against Candida albicansand Candida auris. It exerts anti-inflammatory properties and protects against abdomen irradiation (ABI)-induced intestinal side effects. 6-shogaol also inhibits lipopolysaccharide (LPS)-induced inflammation via peroxisome proliferator-activated receptor gamma (PPAR-γ) activation.
Anticancer Research
6-Shogaol is the dehydrated product of 6-gingerol, extracted from the rhizome ofginger. Treatment of HCC cell line with 6-shogaol resulted in cells with apoptoticphenotypes, which showed signs of cell and nuclear shrinkage as well as substantialchromatin condensation. De-phosphorylation of PERK and activation of theexpression of CHOP initiate caspase cascade reaction inducing apoptosis inHCC. Two-dimensional gel electrophoretic analysis of proteome revealed that in response to the treatment with 6-shogaol, a significant stimulation was observed inproteins related to the ER stress, signifying that apoptosis induced by 6-shogoal didinvolve ER stress. Cells showed marked rise in the UPR target expression, HSP70,Grp94, Grp78/Bip and the other ER chaperones on exposure to 6-shogoal in a time-dependentmanner, which elicited activation of caspase-3 and degradation of polyADP ribose polymerase (PARP). Various ER chaperone proteins improve adaptationof cancer cells to hypoxic environment and aid in developing resistance againstanticancer therapy (Zorzi and Bonvini 2011; Urra et al. 2016). Screening of specificinhibitors of Grp78 as antitumour agents (Hu et al. 2012; Liu et al. 2013; Venkatesanet al. 2015) implies that inhibition of Grp78/Bip is a very promising anticancerstrategy. HCC cells are selectively killed by 6-shogaol in the absence of anynoticeable toxic consequence on normal healthy cells and very little toxicity asstudied on SMMC7721 xenograft mice. Administration of 6-shogaol and salubrinaltogether for distinct time intervals resulted in significant increase in ER stress in thecell. It appears that 6-shogaol in combination with salubrinal has great therapeuticvalue against various malignancies including HCC (Hu et al. 2012).
