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Ginger extract and its constituents gingerol, shogaol and zingerone were tested in Salmonella typhimurium strains TA 100, TA 98, TA 1535 and TA 1538 in the presence and in absence of S9 mix. It was observed that ginger extract, gingerol and shogaol were mutagenic on metabolic activation in strains TA 100 and TA 1535, but zingerone was non-mutagenic in all the four strains with or without S9 mix. When mutagenicity of gingerol and shogaol was tested in presence of different concentrations of zingerone it was observed that zingerone suppressed mutagenic activity in both the compounds in a dose dependent manner.

The products of thermal degradation of gingerols, the pungent component of the spice ginger under gas chromatographic conditions have been re-examined. Besides breakdown to zingerone and aldehydes, substantial dehydration of gingerols to shogaols has been established by improved gas chromatographic separation. The identity of the pungent and poorly pungent homologues have been clearly established as (6)- and (8)-, and (10)-gingerols/shogaols resp. Programmed temp. gas chromatography combined with TLC separation has provided a method for determining the ratio of the homologues and a possible method for estimation of gingerols and shogaols in ginger oleoresin. [See FSTA (1978) 10 6T221.]

The gingerol compounds of freeze-dried ginger ( Zingiber officinale Roscoe) were extracted by liquid carbon dioxide (600–700 p.s.i.), isolated by thin-layer chromatography and fractionated into individual gingerol compounds by preparative high-performance liquid chromatography. Two homologous series, 6-, 8-, 10-, 12-, 14-gingerols and methyl-6-, methyl-8-, methyl-10-, methyl-12-gingerols were identified by the combined results of (1) high-performance liquid chromatographic retention in analytical column; (2) molecular ion determination of isolated gingerol compounds by fast atom bombardment-mass spectrometry; (3) gas chromatography and gas chromatography-mass spectrometry analyses of aldehydes and ketones formed from the thermal degradation of the corresponding gingerol compounds. This is the first report of the presence in ginger of 14-gingerol and gingerols with methyl sidechains.

Isomeric shogaols were derived by thermal dehydration of isolated gingerols of ginger (Zingiber officinale Rescoe), isolated by thin-layer chromatography and fractionated by preparative high-performance liquid chromatography. Two homologous series of isomeric shogaol compounds, cis- and trans,-6-shogaol, 8-shogaol, 10-shogaol, 12-shogaol and syn- and anti-methyl-6-shogaol, methyl-8-shogaol, methyl-10-shogaol, were identified by the combined results of analytical high-performance liquid chromatography, fast atom bombardment-mass spectrometry, gas chromatography, gas chromatography-mass spectrometry and 1H NMR spectroscopy. This is the first report of the presence of cis and trans isomers of shogaols and shogaols with methyl side-chains.

Several essential oils, components of these oils, and three vegetables (welsh onion, chinese garlic and ginger) were tested for their antioxidative effects on both dehydrated model based on carboxymethylcellulose and dehydrated pork. Samples treated with each materials mentioned above by various means were packed in cans under an atmospheric pressure after freeze-dehydration. The cans were stored at 37°C and the rancidity of the contents was measured at intervals by thiobarbituric acid and peroxide value test or by the oxygen analysis of the head space. Both clove and thyme oil exhibited apparent antioxidative effects and similar results were obtained with eugenol and thymol, the major components in respective oils. When the model system or pork was dehydrated with welsh onion or garlic which was placed separately on the same shelf of the dryer during dehydration, the process of oxidation was retarded even in the absence of welsh onion or garlic themselves in the cans. However, much higher effects were obtained in cans packed with dehydrated welsh onion or garlic, and the addition of allyl sulfide or allyl disulfide prior to the dehydration revealed the highest antioxidative effects. With ginger, the effect was lower than with welsh onion or garlic, but the addition of the components of ginger, shogaol and zingeron, proved to have an excellent antioxidative effect comparable to that of allyl sulfide or allyl disulfide.

The present study evaluated the hepatoprotective activity of ginger oleoresin against Carbontetrachloride induced liver toxic damage in rats. Rats were divided into six groups. Hepatotoxicity was induced by the administration of a single intraperitoneal dose (2ml/kg) of Carbontetrachloride in experimental rats. Post-treatment with Ginger oleoresin at 300 and 600mg/kg dose given by oral routewas carried out to find their protective effectsagainst carbontetrachloride induced hepatic injury. Biochemical parameterfor oxidative stress, inflammation and lipid profile along with genotoxicity and histological changes in rat serum and liver were studied. Silymarin was used as standard hepatoprotective agent. Extracted oleoresin dose dependently provided hepatoprotective effects.The hepatoprotective action of ginger oleoresin may be related to its free radical scavenging,anti-inflammatory and hypolipidemic activity and concluded to be partly mediated by its active constituent’s 6-gingerol, shogaol and zingerone. -phospate; CCl3 *, Trichloromethyl free radical; CCl3 OO*, Trichloromethyl peroxy radical; ROS, Reactive oxygen species; iNOS, inducible nitric oxide synthase; NO, Nitric oxide, VLDL, Very low density lipoprotein.

Pharmacological actions of (6)-shogaol and capsaicin were studied. Both (6)-shogaol (0.5 mg/kg, i.v.) and capsaicin (0.1 mg/kg, i.v.) caused a triad such as a rapid fall in blood pressure, bradycardia and aponea in rats. Both drugs-induced marked pressor responses in blood pressure, which occurred after the rapid fall, were markedly reduced by a spinal destruction. In pithed rats, both drugs-induced peripheral pressor responses were markedly reduced with the combined treatment of [D-Arg1, D-Pro2, D-Trp7,9, Leu11]-substance P (0.5 mg/kg, i.v.), phentolamine (10 mg/kg, i.v.) and the section of sciatic nerves. In isolated guinea-pig trachea, (6)-shogaol (100 microM) and capsaicin (10 microM) induced contractile responses which were slightly inhibited by substance P antagonist (10 microM), but exhibited also a tachyphylaxis. Furthermore, although (6)-shogaol (3.6 microM) showed positive inotropic and chronotropic actions on isolated atria in rats, this effect of (6)-shogaol disappeared by repeated injections or pretreatment (100 mg/kg, s.c.) of (6)-shogaol. These results suggest that (6)-shogaol and capsaicin have similar actions, and that both drugs may cause a peripheral action by releasing an unknown active substance from nerve ends.

General pharmacological studies were performed on (6)-gingerol and (6)-shogaol which are the pungent constituents of ginger (Zingiber officinale Roscoe). Intravenous (i.v.) administration of (6)-gingerol (at 1.75-3.5 mg/kg) or (6)-shogaol (at 1.75-3.5 mg/kg) and oral administration of them (at 70-140 mg/kg) produced an inhibition of spontaneous motor activity, an antipyretic and analgesic effects, prolonged hexobarbital-induced sleeping time, and these effects of (6)-shogaol were mostly more intensive than that of (6)-gingerol. (6)-Shogaol showed an intense antitussive effect in comparison with dihydrocodeine phosphate. In the electro-encephalogram of cortex, the low amplitude fast wave pattern was observed for 5 min after i.v. administration of (6)-shogaol, and then changed to the drowsy pattern, which was restored after 60 min. In the gastro-intestinal system, (6)-shogaol intensively inhibited the traverse of charcoal meal through the intestine in contrast with (6)-gingerol after i.v. administration of 3.5 mg/kg, but (6)-shogaol facilitated such an intestinal function after oral administration of 35 mg/kg. Both (6)-shogaol and (6)-gingerol suppressed gastric contraction in situ, and the suppression by the former was more intensive than that by the latter. In the cardiovascular system, both (6)-shogaol and (6)-gingerol produced depressor response at lower doses on the blood pressure. At high doses, both drugs produced three phase pattern.

The pungent principles of ginger —zingerone, gingerol and shogaol— are synthesized starting with vanillin in good yields by utilizing the Lewis acid-promoted cross aldol reaction in each key step.

Ginger (Zingiber officinale Roscoe) is widely used as medicinal plant. According to the Committee on Herbal Medicinal Products (HMPC), dried powdered ginger rhizome can be applied for the prevention of nausea and vomiting in motion sickness (well-established use). Beyond this, a plethora of pre-clinical studies demonstrated anti-cancer, anti-oxidative, or anti-inflammatory actions. 6-Shogaol is formed from 6-gingerol by dehydration and represents one of the main bioactive principles in dried ginger rhizomes. 6-Shogaol is characterized by a Michael acceptor moiety being reactive with nucleophiles. This review intends to compile important findings on the actions of 6-shogaol as an anti-inflammatory compound: in vivo, 6-shogaol inhibited leukocyte infiltration into inflamed tissue accompanied with reduction of edema swelling. In vitro and in vivo, 6-shogaol reduced inflammatory mediator systems such as COX-2 or iNOS, affected NFκB and MAPK signaling, and increased levels of cytoprotective HO-1. Interestingly, certain in vitro studies provided deeper mechanistic insights demonstrating the involvement of PPAR-γ, JNK/Nrf2, p38/HO-1, and NFκB in the anti-inflammatory actions of the compound. Although these studies provide promising evidence that 6-shogaol can be classified as an anti-inflammatory substance, the exact mechanism of action remains to be elucidated. Moreover, conclusive clinical data for anti-inflammatory actions of 6-shogaol are largely lacking.

(6)-Shogaol, a pungent component of ginger, which is contained in semi-dried ginger but is rarely found in fresh ginger inhibited carrageenin-induced swelling of hind paw in rats and arachidonic acid (AA)-induced platelet aggregation in rabbits. Moreover, (6)-shogaol prevented prostaglandin I2 (PGI2) release from the aorta of rats when tested as an inhibitor of platelet aggregation. These results suggest that (6)-shogaol may have an inhibitory action on the cyclo-oxygenases in both platelets and aorta. Examination of the effects of (6)-shogaol on cyclo-oxygenases in rabbit platelets and microsome fractions of rat aorta indicated that (6)-shogaol inhibited cyclo-oxygenase activities of both tissues in a concentration-dependent manner. Furthermore, when we examined the effect of (6)-shogaol on 5-lipoxygenase from RBL-1 cells, (6)-shogaol exhibited an inhibitory action on 5-lipoxygenase activity. Therefore, it seems that the inhibitory effects of (6)-shogaol on the carrageenin-induced paw edema, AA-induced platelet aggregation and PGI2 production of aorta may be caused by the inhibition of cyclo-oxygenase activity.

Scope Vascular smooth muscle cell (VSMC) proliferation is involved in the pathogenesis of cardiovascular disease, making the identification of new counteracting agents and their mechanisms of action relevant. Ginger and its constituents have been reported to improve cardiovascular health, but no studies exist addressing a potential interference with VSMC proliferation.

Simulation and computational analysis of 6-gingerol and 6-shogaol is done to evaluate their binding affinity against ERα. Active site prediction was done using Computed Atlas of Surface Topography of Proteins (CASTp) to determine the binding pocket of ERα. Molecular docking and molecular dynamics (MD) simulation were done to assess the binding affinity and stability of the ligand-ERα complexes formed. Results showed that Tamoxifen have lowest binding energy (-9.61 ± 0.39 kcal/mol) followed by 6-gingerol (-6.59 ± 0.29 kcal/mol) and 6-shogaol (-5.70 ± 0.36 kcal/mol). Inhibition constant (Ki) range of TMX-ERα was found to be drastically lower than both 6GN-ERα and 6SG-ERα. Based on the difference in the binding energy range and inhibition constant, 6-gingerol and 6-shogaol showed less potential in substituting tamoxifen for the inhibition of ERɑ. Docking complexes formed was supported with stability in root mean square deviation (RMSD) and total binding energy of the complexes. The study is concluded that 6-gingerol have high level of interactions with the ERα active site in terms of hydrogen bonding whereas hydrophobic interactions are observed with both 6-gingerol and 6-shogaol. However, both ginger bioactive compounds poses low potential as substitute in comparison with tamoxifen against ERα.

International audience; Multitarget compounds are increasingly being pursued for the effective treatment of complex diseases. Herein, we describe the design and synthesis of a novel class of shogaol-huprine hybrids, purported to hit several key targets involved in Alzheimer's disease. The hybrids have been tested in vitro for their inhibitory activity against human acetylcholinesterase and butyrylcholinesterase and antioxidant activity (ABTS(+), DPPH and Folin-Ciocalteu assays), and in intact Escherichia coli cells for their Aβ42 and tau anti-aggregating activity. Also, their brain penetration has been assessed (PAMPA-BBB assay). Even though the hybrids are not as potent AChE inhibitors or antioxidant agents as the parent huprine Y and [4]-shogaol, respectively, they still exhibit very potent anticholinesterase and antioxidant activities and are much more potent Aβ42 and tau anti-aggregating agents than the parent compounds. Overall, the shogaol-huprine hybrids emerge as interesting brain permeable multitarget anti-Alzheimer leads.

The pungent principles of ginger —zingerone, gingerol and shogaol— are synthesized starting with vanillin in good yields by utilizing the Lewis acid-promoted cross aldol reaction in each key step.

The dried rhizomes of ginger (Zingiber officinale Roscoe) yield, to acetone, a complex mixture of substances including a series of S-(+)- gingerols (i.e. 1-(4?- hydroxy-3?-methoxyphenyl)-5-hydroxyalkan-3-ones) with 10,12, and 14 carbon atom side-chains, essential oil, palmitic and other fatty acids, and other unidentified substances. The substances, shogaol and zingerone, described by Nomura as ginger constituents appear to be absent but are formed by the action of alkalis or heat on gingerol or the oleoresin. The gingerol with the 11-carbon side-chain, claimed by Lapworth, Pearson, and Royle as the principal pungent substance in ginger, is also absent. Ginger oleoresin may be qualitatively analysed by thin-layer chromatography on silica gel with hexane-ether (1 : 1).