Highlights Chemoenzymatic synthesis of α-glucosylated 6-gingerol

Human hepatocellular carcinoma, HepG2 cell line (HB-8065) was obtained from the American Type Culture Collection (ATCC; Manassas, VA, USA). HepG2 cells were cultured in Eagle’s Minimum Essential Medium (EMEM) (ATCC (Manassas, VA, USA and Corning, Tewksbury MA, USA) supplemented with 10% fetal bovine serum and 1% of penicillin/streptomycin solution (100 IU/mL of penicillin and 100 µg/ml of streptomycin) (Gibco BRL, Grand Island, NY, USA) under a humidified 5% CO2 at 37°C. For each experiment, HepG2 cells were treated with different concentrations of []-gingerol (Sigma Chemical Co., St. Louise, MO, USA), which was diluted from the stock solution dissolved in DMSO to the culture medium at the maximum final concentration of DMSO at 0.1%.

Shogaols are anhydrous (dehydrated) gingerols, and so are commonly formed when ginger is dried.

Free fatty acid level was also depressed with 0.5 mM []-gingerol by 69 % at 24 h () and 81% after 48 h () as compared with vehicle alone. This data accords with the loss of FASN protein expression and shows reduced de novo fatty acid synthesis.


A short and efficient synthesis of (+)-(S)-[6]-Gingerol is described

[6]-gingerol and [6]-paradol, as well as some other constituents like shogaols, zingerone etc.

Abstract: The present study was aimed at discovering novel biologically active compounds based on the skeletons of gingerol and shogaol, the pungent principles from the rhizomes of Zingiber officinale. Therefore, eight groups of analogues were synthesized and examined for their inhibitory activities of platelet aggregation induced by arachidonic acid, collagen, platelet activating factor, and thrombin. Among the tested compounds, [6]-paradol (5b) exhibited the most significant anti-platelet aggregation activity. It was the most potent candidate, which could be used in further investigation to explore new drug leads.


8-Gingerol is a natural chemical found in the rhizomes of ginger (Z

Aside from its flavour, ginger has long been used in traditional medicine to help treat a variety of aliments, and recently has become popular as a dietary supplement which is claimed to reduce inflammation, protect against cancer, help the body regulate blood sugar and protect against oxidative stress.

PubMed - National Center for Biotechnology Information

N2 - To determine the effects of a [6]-gingerol analogue (6G), a major chemical component of the ginger rhizome, and its stable analogue after digestion in simulated gastric fluid, aza-[6]-gingerol (A6G), on diet-induced body fat accumulation, we synthesized 6G and A6G. Mice were fed either a control regular rodent chow, a high-fat diet (HFD), or a HFD supplemented with 6G and A6G. Magnetic resonance imaging adiposity parameters of the 6G- and A6G-treated mice were compared with those of control mice. Supplementation with 6G and A6G significantly reduced body weight gain, fat accumulation, and circulating levels of insulin and leptin. The mRNA levels of sterol regulatory element-binding protein 1c (SREBP-1c) and acetyl-CoA carboxylase 1 in the liver were significantly lower in mice fed A6G than in HFD control mice. Our findings indicate that A6G, rather than 6G, enhances energy metabolism and reduces the extent of lipogenesis by downregulating SREBP-1c and its related molecules, which leads to the suppression of body fat accumulation.

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AB - To determine the effects of a [6]-gingerol analogue (6G), a major chemical component of the ginger rhizome, and its stable analogue after digestion in simulated gastric fluid, aza-[6]-gingerol (A6G), on diet-induced body fat accumulation, we synthesized 6G and A6G. Mice were fed either a control regular rodent chow, a high-fat diet (HFD), or a HFD supplemented with 6G and A6G. Magnetic resonance imaging adiposity parameters of the 6G- and A6G-treated mice were compared with those of control mice. Supplementation with 6G and A6G significantly reduced body weight gain, fat accumulation, and circulating levels of insulin and leptin. The mRNA levels of sterol regulatory element-binding protein 1c (SREBP-1c) and acetyl-CoA carboxylase 1 in the liver were significantly lower in mice fed A6G than in HFD control mice. Our findings indicate that A6G, rather than 6G, enhances energy metabolism and reduces the extent of lipogenesis by downregulating SREBP-1c and its related molecules, which leads to the suppression of body fat accumulation.