Occurrence, biological activity and metabolism of 6-shogaol

Abstract

As one of the main bioactive compounds of dried ginger, 6-shogaol has been widely used to alleviate many ailments. It is also a major pungent flavor component, and its precursor prior to dehydration is 6-gingerol, which is reported to be responsible for the pungent flavor and biological activity of fresh ginger. Structurally, gingerols including 6-gingerol have a β-hydroxyl ketone moiety and is liable to dehydrate to generate an α,β-unsaturated ketone under heat and/or acidic conditions. The conjugation of the α,β-unsaturated ketone skeleton in the chemical structure of 6-shogaol explicates its higher potency and efficacy than 6-gingerol in terms of antioxidant, anti-inflammatory, anticancer, antiemetic and other bioactivities. Research on the health benefits of 6-shogaol has been conducted and results have been reported recently; however, scientific data are scattered due to a lack of systematic collection. In addition, action mechanisms of the preventive and/or therapeutic actions of 6-shogaol remain obscurely non-collective. Herein, we review the preparations, biological activity and mechanisms, and metabolism of 6-shogaol as well as the properties of 6-shogaol metabolites.

The effects of steamed ginger ethanolic extract on weight and body fat loss: a randomized, double-blind, placebo-controlled clinical trial

“…Since its structure is thermally unstable, 6-gingerol is converted to 6-shogaol, which has an a,b-unsaturated carbonyl group, as a result of processing techniques such as heating, drying, and steaming (Bhattarai et al, 2001;2007;Dugasani et al, 2010;Kou et al, 2018). Both substances are beneficial to health, but several recent reports have indicated that 6-shogaol is superior to 6-gingerol (Dugasani et al, 2010;Ho and Chang, 2018;Jin et al, 2014;Wang et al, 2017), presumably due to its a,bunsaturated carbonyl group (Kou et al, 2018). An a,bunsaturated carbonyl group is present not only in 6-shogaol, but also in curcumin and chalcone (Rodrigues et al, 2016), which are known to have excellent pharmacological activities.…”

“…Steamed ginger ethanolic extract (SGE) is a ginger product in which the 6-shogaol content has been increased through steaming and ethanol extraction. SGE is expected to be more potent than other ginger products due to the a,bunsaturated ketone structure of its side-chain (Kou et al, 2018). In a previous study, SGE was reported to inhibit hepatic lipid accumulation by suppressing the expression of SREBP1c (Srebpf1), a lipogenic transcription factor.…”

Effects of ginger constituent 6‐shogaol on gastroesophageal vagal afferent C‐fibers

“…Ginger has been used as an herbal medicine to relieve nausea/vomiting and gastrointestinal discomforts (bloating and pain), but the cellular and molecular mechanisms of its neuronal actions are still unclear . It is known that the pharmacological effect of ginger is mainly produced by its bioactive phytochemicals, including the pungent principle gingerols (including 4‐, 6‐, 8, 10‐, and 12‐gingerols) and their more bioactive dehydrated products, the shogaols (including 6‐, 8‐, and 10‐shogaols) …”

“…1,2 It is known that the pharmacological effect of ginger is mainly produced by its bioactive phytochemicals, including the pungent principle gingerols (including 4-, 6-, 8, 10-, and 12-gingerols) and their more bioactive dehydrated products, the shogaols (including 6-, 8-, and 10-shogaols). 3,4 In the last two decades, advances in sensory neurobiology have been made by discovering the transient receptor potential (TRP) channel family that are responsible for mediating noxious sensations induced by commonly used pungencies. Among them, TRPV1 is activated by capsaicin in hot peppers, TRPA1 can be activated by isothiocyanate in horseradish, cinnamaldehyde in cinnamon, and thiosulfinates in garlic, and TRPM8 is responsible for the "cooling" sensation of menthol in peppermint.…”

The antagonism of 6-shogaol in high-glucose-activated NLRP3 inflammasome and consequent calcification of human artery smooth muscle cells

“…Generally, shogaols have been suggested to be more effective than gingerols in attenuating the patients' uncomfortable and status. And, 6-shogaol is the most dominant one [30]. However, the molecular mechanism and metabolic fate of shogaols, including 6-shogaol, in antagonizing and improving the status of these diseases have not been clearly identified.…”