gingerol and zingerone

Currently, ginger is one the most consumed plants when dealing with the treatments of various illnesses. So far, it is known that various biologically active molecules, such as gingerols, shogaols and zingerone, among others, are the main responsible for specific biological activities, opening a new window for its utilization as a nutraceutical in foods. In pioneering extraction processes, solvent extraction has been initially used for these applications; however, the drawbacks of this typical extraction method compared with other emergent separation techniques make it possible for the exploration of new extraction pathways, including microwave, ultrasound, supercritical, subcritical and pressurized-assisted extraction, along with three phase partitioning, high-speed counter current chromatography and magnetic solid phase extraction. To the best of our knowledge, there is no report documenting the recent studies and cases of study in this field. Therefore, we comprehensively review the progress and the latest findings (over the last five years) on research developments, including patents and emerging extraction methods, aiming at the purification of biologically active molecules (gingerols, shogaols and zingerone) contained in ginger. Over the course of this review, particular emphasis is devoted to breakthrough strategies and meaningful outcomes in ginger components extraction. Finally, dosage and safety concerns related to ginger extracts are also documented.

Topics: Catechols; Dietary Supplements; Fatty Alcohols; Plant Extracts; Zingiber officinale

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

Ginger, the rhizome of Zingiber officinalis, one of the most widely used species of the ginger family, is a common condiment for various foods and beverages. Ginger has a long history of medicinal use dating back 2500 years. Ginger has been traditionally used from time immemorial for varied human ailments in different parts of the globe, to aid digestion and treat stomach upset, diarrhoea, and nausea. Some pungent constituents present in ginger and other zingiberaceous plants have potent antioxidant and anti-inflammatory activities, and some of them exhibit cancer preventive activity in experimental carcinogenesis. The anticancer properties of ginger are attributed to the presence of certain pungent vallinoids, viz. [6]-gingerol and [6]-paradol, as well as some other constituents like shogaols, zingerone etc. A number of mechanisms that may be involved in the chemopreventive effects of ginger and its components have been reported from the laboratory studies in a wide range of experimental models.

Topics: Animals; Anticarcinogenic Agents; Breast Neoplasms; Catechols; Colonic Neoplasms; Fatty Alcohols; Gastrointestinal Neoplasms; Guaiacol; Humans; Ketones; Oils, Volatile; Skin Neoplasms; Tumor Cells, Cultured; Zingiber officinale

Ginger extract has been reported to possess antioxidant properties. However, components isolated from ginger have been rarely reported to inhibit oxidation. Herein, the antioxidant properties of ginger and purified components derived from it (6-gingerol, zingerone, rutin, quercetin, and kaempferol) were confirmed by using HPLC and were further used to investigate its effect on lamb meat. Myofibrillar proteins isolated (MPI) from lamb meat were incubated with ginger and its constituents under induced Fenton oxidation (1.0 mmol/L FeCl3, 0.1 mmol/L Asc, and 20 mmol/L H2O2) for 1, 3,5, and 7 h. Incubating meat protein isolate in the absence of ginger extract or its components resulted in a substantial drop in sulfhydryl groups, an increase in protein carbonyl content, and a corresponding increase in TBARS content. However, ginger extract and its constituents demonstrated antioxidant properties, which might be attributed to their hydroxyl groups and suitable solubilizing side chains. Overall, ginger extract exhibited the highest antioxidant capabilities of all treated samples, suggesting that ginger extracts may be used as a natural antioxidant in meat and lipid/protein-containing processed products. SIGNIFICANCE OF THE STUDY: Ginger extract is also frequently used as a herbal medicine due to its anti-inflammatory, anti-cancer, and antibacterial qualities. Nonvolatile pungent chemicals found in ginger, such as gingerol, shogaols, paradols, and zingerone, as well as kaempferol, rutin, and other phenolic compounds, have been confirmed in ginger extract and have been shown to have antioxidant action driven by free radical elimination. Despite these findings, ginger extract and its pure constituent components have seldom been shown to have the ability to slow protein and lipid oxidation in meat and meat-related products. The effect of ginger extracts on the oxidative stability of myofibriller protein isolate has never been investigated. Exploiting the phenolic content of ginger extract may result in a discovery that would have a huge influence on both the ginger and meat industries as well as other food processing sectors. The first aim of our study was to confirm the presence of six selected phenolic compounds (rutin, kaempferol, 6-gingerol, zingerone, naringenin, and quercetin) in ginger as reported by literature, and the second objective was to determine the efficacy of ginger extracts and its purified constituents on myofibrillar protein isolate treated under

Topics: Animals; Anti-Bacterial Agents; Anti-Inflammatory Agents; Antioxidants; Catechols; Fatty Alcohols; Guaiacol; Hydrogen Peroxide; Kaempferols; Meat Proteins; Phenols; Plant Extracts; Protein Carbonylation; Quercetin; Rutin; Sheep; Thiobarbituric Acid Reactive Substances; 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

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

The kinetics parameters of paradols with different acyl chain lengths have been evaluated to determine their antiobesity site of action. Rats were orally administered olive oil containing 0-, 6-, 8-, or 12-paradol, and blood samples were collected at different time points. The concentrations of the paradols in the plasma were analyzed both with and without β-glucuronidase treatment. The area under the plasma concentration-time curve from 0 to 24 h (AUC(0-24h)) of the parent compounds decreased with increasing acyl chain length. Whereas 12-paradol showed the largest AUC(0-24h) with the longest time to reach its maximum plasma concentration of all of the compounds tested, the AUC(0-24h) values of the metabolites decreased with increasing acyl chain length. These results indicate that increasing acyl chain length leads to a decrease in the absorption of paradols via the intestinal tract, the wall of which was estimated to be their antiobesity site of action.

Topics: Animals; Anti-Obesity Agents; Catechols; Fatty Alcohols; Guaiacol; Ketones; Male; Phenols; Rats; Rats, Sprague-Dawley

Drugs used both in classical chemotherapy and the more recent targeted therapy do not have cancer cell specificity and, hence, cause severe systemic side effects. Tumors also develop resistance to such drugs due to heterogeneity of cell types and clonal selection. Several traditional dietary ingredients from plants, on the other hand, have been shown to act on multiple targets/pathways, and may overcome drug resistance. The dietary agents are safe and readily available. However, application of plant components for cancer treatment/prevention requires better understanding of anticancer functions and elucidation of their mechanisms of action. The current study focuses on the anticancer properties of fenugreek, a herb with proven anti-diabetic, antitumor and immune-stimulating functions.. Jurkat cells were incubated with 30 to 1500 μg/mL concentrations of 50% ethanolic extract of dry fenugreek seeds and were followed for changes in viability (trypan blue assay), morphology (microscopic examination) and autophagic marker LC3 transcript level (RT-PCR).. Incubation of Jurkat cells with fenugreek extract at concentrations ranging from 30 to 1500 μg/mL for up to 3 days resulted in cell death in a dose- and time-dependent manner. Jurkat cell death was preceded by the appearance of multiple large vacuoles, which coincided with transcriptional up-regulation of LC3. GC-MS analysis of fenugreek extract indicated the presence of several compounds with anticancer properties, including gingerol (4.82%), cedrene (2.91%), zingerone (16.5%), vanillin (1.52%) and eugenol (1.25%).. Distinct morphological changes involving appearance of large vacuoles, membrane disintegration and increased expression of LC3 transcripts indicated that fenugreek extract induced autophagy and autophagy-associated death of Jurkat cells. In addition to the already known apoptotic activation, induction of autophagy may be an additional mechanism underlying the anticancer properties of fenugreek. This is the first report showing fenugreek as an inducer of autophagy in human cells and further work is needed to define the various intermediates of the autophagic pathway.

Topics: Antineoplastic Agents, Phytogenic; Autophagy; Benzaldehydes; Catechols; Cell Line; Dose-Response Relationship, Drug; Eugenol; Fatty Alcohols; Guaiacol; Humans; Jurkat Cells; Leukemia, T-Cell; Lymphoma, T-Cell; Microtubule-Associated Proteins; Phytotherapy; Plant Extracts; Polycyclic Sesquiterpenes; Seeds; Sesquiterpenes; Transcription, Genetic; Trigonella; Up-Regulation; Vacuoles

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

[6]-Gingerol, a major pungent ingredient found in the rhizome of ginger, has been reported to possess a strong antiinflammatory activity, which is considered to be closely associated with its cancer chemopreventive potential. [6]-Paradol, another pungent phenolic substance found in ginger and other Zingiberaceae plants, also has a vanilloid structure found in other chemopreventive phytochemicals including curcumin. In the present study, [6]-gingerol and [6]-paradol were found to exert inhibitory effects on the viability and DNA synthesis of human promyelocytic leukemia (HL-60) cells. The cytotoxic and antiproliferative effects of both compounds were associated with apoptotic cell death. The above results suggest that [6]-gingerol and [6]-paradol possess potential cytotoxic/cytostatic activities.

Topics: Anticarcinogenic Agents; Antineoplastic Agents; Apoptosis; Catechols; Fatty Alcohols; Guaiacol; HL-60 Cells; Humans

Antioxidants minimize oxidation of the lipid components in foods. There is an increasing interest in the use of natural and/or synthetic antioxidants in food preservation, but it is important to evaluate such compounds fully for both antioxidant and pro-oxidant properties. The properties of thymol, carvacrol, 6-ginerol, hydroxytyrosol and zingerone were characterized in detail. Thymol, carvacrol, 6-gingerol and hydroxytyrosol decreased peroxidation of phospholipid liposomes in the presence of iron(III) and ascorbate, but zingerone had only a weak inhibitory effect on the system. The compounds were good scavengers of peroxyl radicals (CCl3O2; calculated rate constants > 10(6) M-1 sec-1) generated by pulse radiolysis. Thymol, carvacrol, 6-gingerol and zingerone were not able to accelerate DNA damage in the bleomycin-Fe(III) system. Hydroxytyrosol promoted deoxyribose damage in the deoxyribose assay and also promoted DNA damage in the bleomycin-Fe(III) system. This promotion was inhibited strongly in the deoxyribose assay by the addition of bovine serum albumin to the reaction mixtures. Our data suggest that thymol, carvacrol and 6-gingerol possess useful antioxidant properties and may become important in the search for 'natural' replacements for 'synthetic' antioxidant food additives.

Topics: Antioxidants; Ascorbic Acid; Bleomycin; Catechols; Cymenes; Deoxyribose; DNA Damage; Fatty Alcohols; Ferric Compounds; Food Preservation; Guaiacol; Hydroxyl Radical; Lipid Peroxidation; Liposomes; Monoterpenes; Phenylethyl Alcohol; Pulse Radiolysis; Terpenes; Thymol

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