shogaol and zingerone

As the human life expectancy increases, age-linked diseases have become more and more frequent. The worldwide increment of dementia cases demands medical solutions, but the current available drugs do not meet all the expectations. Recently the attention of the scientific community was attracted by natural compounds, used in ancient medicine, known for their beneficial effects and high tolerability. This review is focused on Ginger (

Topics: Catechols; Dementia; Drug Discovery; Fatty Alcohols; Guaiacol; Humans; Ketones; Models, Molecular; Plant Extracts; Protective Agents; Sesquiterpenes; Structure-Activity Relationship; Zingiber officinale

The rhizomes of Zingiber officinale Roscoe (Zingiberaceae), commonly known as ginger, is one of the most widely used spice and condiment. It is also an integral part of many traditional medicines and has been extensively used in Chinese, Ayurvedic, Tibb-Unani, Srilankan, Arabic, and African traditional medicines, since antiquity, for many unrelated human ailments including common colds, fever, sore throats, vomiting, motion sickness, gastrointestinal complications, indigestion, constipation, arthritis, rheumatism, sprains, muscular aches, pains, cramps, hypertension, dementia, fever, infectious diseases, and helminthiasis. The putative active compounds are nonvolatile pungent principles, namely gingerols, shogaols, paradols, and zingerone. These compounds are some of the extensively studied phytochemicals and account for the antioxidant, anti-inflammatory, antiemetic, and gastroprotective activities. A number of preclinical investigations with a wide variety of assay systems and carcinogens have shown that ginger and its compounds possess chemopreventive and antineoplastic effects. A number of mechanisms have been observed to be involved in the chemopreventive effects of ginger. The cancer preventive activities of ginger are supposed to be mainly due to free radical scavenging, antioxidant pathways, alteration of gene expressions, and induction of apoptosis, all of which contribute towards decrease in tumor initiation, promotion, and progression. This review provides concise information from preclinical studies with both cell culture models and relevant animal studies by focusing on the mechanisms responsible for the chemopreventive action. The conclusion describes directions for future research to establish its activity and utility as a human cancer preventive and therapeutic drug. The above-mentioned mechanisms of ginger seem to be promising for cancer prevention; however, further clinical studies are warranted to assess the efficacy and safety of ginger.

Topics: Animals; Anti-Inflammatory Agents; Anticarcinogenic Agents; Antiemetics; Antioxidants; Apoptosis; Carcinogens; Catechols; Cell Cycle; Cell Line, Tumor; Drug Evaluation, Preclinical; Fatty Alcohols; Guaiacol; Humans; Lipid Peroxidation; Neoplasms; Plant Extracts; Protein Carbonylation; Rhizome; Signal Transduction; Spices; Transcription Factors; Zingiber officinale

Topics: Catechols; Drug Resistance, Bacterial; Edible Films; Fatty Alcohols; Guaiacol; Microwaves; Oryza; Plant Extracts; Solid Phase Extraction; Streptococcus mutans; Thailand; Zingiber officinale

Ginger oleoresin (GO) can be encapsulated within a protective lipid matrix in order to facilitate handling, provide protection against the external environment or promote the stability of GO compounds. The aim of this study was to verify the ability of solid lipid microparticles (SLMs) containing GO (10-20% w/w) to maintain or improve the stability of ginger compounds, by monitoring SLMs' characteristics during storage at different temperatures (25 and 40 °C). The lipids matrix of SLMs were composed by stearic acid (90, 80, 75, 65% w/w) and oleic acid (15% w/w), The crystalline structure of the particles after 84 days of storage did not present any polymorphic alterations, while presenting spherical form upon scanning by electron microscopy. SLMs containing oleic acid showed degradation of 6-gingerol when stored at 40 °C. Major volatile compounds had better stability in particles containing oleic acid. Kinetics of volatiles release resulted in a diffusion mechanism. SLMs showed better stability of GO compounds during storage at 25 °C than un-encapsulated GO and could, therefore, improve its distribution in foods due to its conversion to powder.

Topics: Catechols; Crystallization; Fatty Alcohols; Food Preservation; Food Storage; Guaiacol; Kinetics; Odorants; Oleic Acid; Particle Size; Plant Extracts; Powders; Stearic Acids; Surface Properties; Temperature; Volatile Organic Compounds; Zingiber officinale

The epithelial-mesenchymal transition (EMT) is an important cellular process during which polarized epithelial cells become motile mesenchymal cells, which promote cancer metastasis. Ginger, the rhizome of Zingiber officinale, is extensively used in cooking worldwide and also as a traditional medicinal herb with antioxidant, anti-inflammatory and anticancer properties. Several pungent compounds have been identified in ginger, including zingerone, which has anticancer potential. However, the role of zingerone in EMT is unclear. We investigated the synergistic effect of zingerone and its derivative on EMT. Transforming growth factor-beta 1 (TGF-β1) induces the EMT to promote hepatocellular carcinoma metastasis, including migration and invasion. To understand the repressive role of the combination of zingerone and its derivative (ZD 2) in hepatocellular carcinoma metastasis, we investigated the potential use of each compound of ginger, such as zingerone, ZD 2 and 6-shogaol, or the mixture of zingerone and ZD 2 (ZD 2-1) as inhibitors of TGF-β1 induced EMT development in SNU182 hepatocellular carcinoma cells in vitro. We show that ZD 2-1, but not zingerone, ZD 2 and 6-shogaol significantly increased expression of the epithelial marker E-cadherin and repressed Snail upregulation and expression of the mesenchymal marker N-cadherin during initiation of the TGF-β1 induced EMT. In addition, ZD 2-1 inhibited the TGF-β1 induced increase in cell migration and invasion of SNU182 hepatocellular carcinoma cells. Furthermore, ZD 2-1 significantly inhibited TGF-β1 regulated matrix metalloproteinase-2/9 and activation of Smad2/3. We also found that ZD 2-1 inhibited nuclear translocation of NF-κB, activation of p42/44 MAPK/AP1 signaling pathway in the TGF-β1 induced EMT. Our findings provide new evidence that combined treatment with ZD 2, novel zingerone derivative, and zingerone synergistically suppresses hepatocellular carcinoma metastasis in vitro by inhibiting the TGF-β1 induced EMT.

Topics: Carcinoma, Hepatocellular; Cell Line, Tumor; Drug Synergism; Epithelial-Mesenchymal Transition; Guaiacol; Humans; Liver Neoplasms; Neoplasm Invasiveness; Transforming Growth Factor beta1

Ginger (Zingiber officinale Rosc.) is a common dietary adjunct that contributes to the taste and flavor of foods, and is also an important Traditional Chinese medicine (TCM). Different processing methods can produce different processed gingers with dissimilar chemical constituents and pharmacological activities. In this study, an ultra-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry (UPLC/QTOF-MS) was applied to identify the complicated components from fresh, dried, stir-frying and carbonized ginger extracts. All of the 27 compounds were identified from four kinds of ginger samples (fresh, dried, stir-frying and carbonized ginger). Five main constituents (zingerone, 6-gingerol, 8-gingerol, 6-shogaol and 10-gingerol) in these four kinds of ginger sample extracts were simultaneously determined by UPLC-PDA. Meanwhile, the antioxidant effect of fresh, dried, stir-frying and carbonized gingers were evaluated by three assays (2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis(3-ethylbenzthiazolinesulfonic acid) diammonium salt (ABTS), and ferric reducing antioxidant power (FRAP)). The results demonstrated that antioxidant activity of dried ginger was the highest, for its phenolic contents are 5.2-, 1.1- and 2.4-fold higher than that of fresh, stir-frying and carbonized ginger, respectively, the antioxidant activities' results indicated a similar tendency with phenolic contents: dried ginger>stir-frying ginger>fresh ginger>carbonized ginger. The processing contributed to the decreased concentration of gingerols and the increased levels of shogaols, which reducing the antioxidant effects in pace with processing. This study elucidated the relationship of the heating process with the constituents and antioxidant activity, and provided a guide for choosing different kinds of ginger samples on clinical application.

Topics: Antioxidants; Catechols; Chromatography, High Pressure Liquid; Fatty Alcohols; Guaiacol; Mass Spectrometry; Plant Extracts; Zingiber officinale

Fresh rhizomes of Zingiber officinale (ginger), when subjected to steam distillation, yielded ginger oil in which curcumene was found to be the major constituent. The thermally labile zingiberene-rich fraction was obtained from its diethyl ether extract. Column chromatography of ginger oleoresin furnished a fraction from which [6]-gingerol was obtained by preparative TLC. Naturally occurring [6]-dehydroshogaol was synthesised following condensation of dehydrozingerone with hexanal, whereas zingerone and 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane were obtained by hydrogenation of dehydrozingerone with 10% Pd/C. The structures of the compounds were established by 1H NMR, 13C NMR and mass (EI-MS and ES-MS) spectral analysis. The test compounds exhibited moderate insect growth regulatory (IGR) and antifeedant activity against Spilosoma obliqua, and significant antifungal activity against Rhizoctonia solani. Among the various compounds, [6]-dehydroshogaol exhibited maximum IGR activity (EC50 3.55 mg ml-1), while dehydrozingerone imparted maximum antifungal activity (EC50 86.49 mg litre-1).

Topics: Animals; Antifungal Agents; Catechols; Fatty Alcohols; Feeding Behavior; Guaiacol; Insect Control; Insecticides; Larva; Lepidoptera; Magnetic Resonance Spectroscopy; Mass Spectrometry; Mutagens; Plants, Medicinal; Styrenes; Zingiber officinale

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.

Topics: Animals; Catechols; Fatty Alcohols; Guaiacol; Male; Mutagenicity Tests; Mutagens; Rats; Rats, Inbred Strains; Salmonella typhimurium; Structure-Activity Relationship