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Barbara N Timmermann - One of the best experts on this subject based on the ideXlab platform.
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comparative effects of two Gingerol containing zingiber officinale extracts on experimental rheumatoid arthritis
Journal of Natural Products, 2009Co-Authors: Janet L Funk, Jennifer B Frye, Janice Oyarzo, Barbara N TimmermannAbstract:Ginger (Zingiber officinale) supplements are being promoted for arthritis treatment in western societies based on ginger’s traditional use as an anti-inflammatory in Chinese and Ayurvedic medicine. However, scientific evidence of ginger’s antiarthritic effects is sparse, and its bioactive joint-protective components have not been identified. Therefore, the ability of a well-characterized crude ginger extract to inhibit joint swelling in an animal model of rheumatoid arthritis, streptococcal cell wall (SCW)-induced arthritis, was compared to that of a fraction containing only Gingerols and their derivatives. Both extracts were efficacious in preventing joint inflammation. However, the crude dichloromethane extract, which also contained essential oils and more polar compounds, was more efficacious (when normalized to Gingerol content) in preventing both joint inflammation and destruction. In conclusion, these data document a very significant joint-protective effect of these ginger samples, and suggest that non-Gingerol components are bioactive and can enhance the antiarthritic effects of the more widely studied Gingerols.
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the effect of extracts from ginger rhizome on inflammatory mediator production
Phytomedicine, 2007Co-Authors: R C Lantz, M Sarihan, Shivanand D Jolad, Aniko M Solyom, Guan Jie Chen, Barbara N TimmermannAbstract:Abstract Compounds from rhizomes of Zingiber officinale , commonly called ginger, have been purported to have anti-inflammatory actions. We have used an in vitro test system to test the anti-inflammatory activity of compounds isolated from ginger rhizome. U937 cells were differentiated and exposed to lipopolysaccharide (LPS) from Escherichia coli (1 μg/ml) in the presence or absence of organic extracts or standard compounds found in ginger (6-, 8-, 10-Gingerol or 6-shogaol) for 24 h. Supernatants were collected and analyzed for the production of prostaglandin E 2 (PGE 2 ) and tumor necrosis factor alpha (TNF- α ) by standard ELISA assays. Predominant compounds in the organic extracts were identified as 6-, 8- 10-Gingerols and 6-, 8-, 10-shogaols. Organic extracts or standards containing Gingerols were not cytotoxic, while extracts or standards containing predominantly shogaols were cytotoxic at concentrations above 20 μg/ml. Crude organic extracts of ginger were capable of inhibiting LPS induced PGE 2 (IC 50 α (IC 50 >30 μg/ml). Thirty three fractions and subfractions, prepared by column chromatography, were analyzed for bioactivity. Extracts containing either predominantly Gingerols or shogaols (identified by HPLC) were both highly active at inhibiting LPS-induced PGE 2 production (IC 50 50 2 production and that the compounds may act at several sites.
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biosynthesis of curcuminoids and Gingerols in turmeric curcuma longa and ginger zingiber officinale identification of curcuminoid synthase and hydroxycinnamoyl coa thioesterases
Phytochemistry, 2006Co-Authors: Maria Del Carmen Ramirezahumada, Barbara N Timmermann, David R. GangAbstract:Members of the Zingiberaceae such as turmeric (Curcuma longa L.) and ginger (Zingiber officinale Rosc.) accumulate at high levels in their rhizomes important pharmacologically active metabolites that appear to be derived from the phenylpropanoid pathway. In ginger, these compounds are the Gingerols; in turmeric these are the curcuminoids. Despite their importance, little is known about the biosynthesis of these compounds. This investigation describes the identification of enzymes in the biosynthetic pathway leading to the production of these bioactive natural products. Assays for enzymes in the phenylpropanoid pathway identified the corresponding enzyme activities in protein crude extracts from leaf, shoot and rhizome tissues from ginger and turmeric. These enzymes included phenylalanine ammonia lyase, polyketide synthases, p-coumaroyl shikimate transferase, p-coumaroyl quinate transferase, caffeic acid O-methyltransferase, and caffeoyl-CoA O-methyltransferase, which were evaluated because of their potential roles in controlling production of certain classes of Gingerols and curcuminoids. All crude extracts possessed activity for all of these enzymes, with the exception of polyketide synthases. The results of polyketide synthase assays showed detectable curcuminoid synthase activity in the extracts from turmeric with the highest activity found in extracts from leaves. However, no Gingerol synthase activity could be identified. This result was explained by the identification of thioesterase activities that cleaved phenylpropanoid pathway CoA esters, and which were found to be present at high levels in all tissues, especially in ginger tissues. These activities may shunt phenylpropanoid pathway intermediates away from the production of curcuminoids and Gingerols, thereby potentially playing a regulatory role in the biosynthesis of these compounds.
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The effect of extracts from ginger rhizome on inflammatory mediator production.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 2006Co-Authors: R C Lantz, M Sarihan, G J Chen, Shivanand D Jolad, Aniko M Solyom, Barbara N TimmermannAbstract:Compounds from rhizomes of Zingiber officinale, commonly called ginger, have been purported to have anti-inflammatory actions. We have used an in vitro test system to test the anti-inflammatory activity of compounds isolated from ginger rhizome. U937 cells were differentiated and exposed to lipopolysaccharide (LPS) from Escherichia coli (1 microg/ml) in the presence or absence of organic extracts or standard compounds found in ginger (6-, 8-, 10-Gingerol or 6-shogaol) for 24 h. Supernatants were collected and analyzed for the production of prostaglandin E(2) (PGE(2)) and tumor necrosis factor alpha (TNF-alpha) by standard ELISA assays. Predominant compounds in the organic extracts were identified as 6-, 8- 10-Gingerols and 6-, 8-, 10-shogaols. Organic extracts or standards containing Gingerols were not cytotoxic, while extracts or standards containing predominantly shogaols were cytotoxic at concentrations above 20 microg/ml. Crude organic extracts of ginger were capable of inhibiting LPS induced PGE(2) (IC(50)30 microg/ml). Thirty three fractions and subfractions, prepared by column chromatography, were analyzed for bioactivity. Extracts containing either predominantly Gingerols or shogaols (identified by HPLC) were both highly active at inhibiting LPS-induced PGE(2) production (IC(50)
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Characterization of Gingerol-related compounds in ginger rhizome (Zingiber officinale Rosc.) by high-performance liquid chromatography/electrospray ionization mass spectrometry.
Rapid communications in mass spectrometry : RCM, 2005Co-Authors: Hongliang Jiang, Aniko M Solyom, Barbara N Timmermann, David R. GangAbstract:This study sought to determine the utility of liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) coupled with diode array detection in identifying Gingerol-related compounds from crude extracts of ginger rhizome. The fragmentation behaviors of compounds in both (-)- and (+)ESI-MS/MS were used to infer and confirm the chemical structures of several groups of compounds, including the Gingerols, methylGingerols, Gingerol acetates, shogaols, paradols, gingerdiols, mono- and diacetyl gingerdiols, and dehydrogingerdiones. Diode array detection at different wavelengths was used to confirm MS/MS-based identification. In total, 31 Gingerol-related compounds were identified from the methanolic crude extracts of fresh ginger rhizome in this study. Three of these compounds were found to be new compounds. This study demonstrated that LC/ESI-MS/MS is a powerful on-line tool for identification of Gingerol-related compounds, especially for thermally labile compounds that cannot be readily detected by GC/MS analysis.
Udaya Sankar Kadimi - One of the best experts on this subject based on the ideXlab platform.
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Characterization of Gingerol analogues in supercritical carbon dioxide (SC CO_2) extract of ginger (Zingiber officinale, R.,)
Journal of Food Science and Technology, 2014Co-Authors: R. Swapna Sonale, Udaya Sankar KadimiAbstract:Organically grown ginger rhizome ( Zingiber officinale Roscoe) SC CO_2 extract obtained at 280 bar and 40 °C and its column chromatographic fractions are characterised for its composition. The components in the extract and fractions are identified by HPLC and LC based MS and are used as standard for the estimation of Gingerol analogues in the extract. HPLC and mass analysis of the extracts confirmed the various forms of Gingerol constituents [4]-, [6]-, [10]-Gingerols and [6]-, [8]-, [10]-shogaols in ginger extracts. SC CO_2 extract of organic ginger was found to show 6-Gingerol around 25.97 % of total extract. The estimation of [6]-Gingerol, [6]-shogaols, [4]Gingerol, [10]-Gingerol and 6-gingediol content of the SC CO_2 purified ginger extract was found to be 75.92 ± 1.14, 1.25 ± 0.04, 4.54 ± 0.04, 13.15 ± 0.30 and 0.37 ± 0.00 % respectively. Antioxidant activity was measured by 2, 2-diphenyl-1-pycryl-hydrazyl (DPPH) free radical scavenging and ferric reducing antioxidant power (FRAP) and the assay have shown 652 ± 0.37 mg TE/g and 3.68 ± 0.18 mg TE/100 g respectively, are significantly higher results with SC CO_2 organic ginger extract. Paradol analogues are not detected in this study. Small quantities of [4]-, [10]gingediol and [6]-gingediacetate are also found in ginger extract.
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Characterization of Gingerol analogues in supercritical carbon dioxide (SC CO2) extract of ginger (Zingiber officinale, R.,)
Journal of Food Science and Technology-mysore, 2012Co-Authors: R. Swapna Sonale, Udaya Sankar KadimiAbstract:Organically grown ginger rhizome (Zingiber officinale Roscoe) SC CO2 extract obtained at 280 bar and 40 °C and its column chromatographic fractions are characterised for its composition. The components in the extract and fractions are identified by HPLC and LC based MS and are used as standard for the estimation of Gingerol analogues in the extract. HPLC and mass analysis of the extracts confirmed the various forms of Gingerol constituents [4]-, [6]-, [10]-Gingerols and [6]-, [8]-, [10]-shogaols in ginger extracts. SC CO2 extract of organic ginger was found to show 6-Gingerol around 25.97 % of total extract. The estimation of [6]-Gingerol, [6]-shogaols, [4]Gingerol, [10]-Gingerol and 6-gingediol content of the SC CO2 purified ginger extract was found to be 75.92 ± 1.14, 1.25 ± 0.04, 4.54 ± 0.04, 13.15 ± 0.30 and 0.37 ± 0.00 % respectively. Antioxidant activity was measured by 2, 2-diphenyl-1-pycryl-hydrazyl (DPPH) free radical scavenging and ferric reducing antioxidant power (FRAP) and the assay have shown 652 ± 0.37 mg TE/g and 3.68 ± 0.18 mg TE/100 g respectively, are significantly higher results with SC CO2 organic ginger extract. Paradol analogues are not detected in this study. Small quantities of [4]-, [10]gingediol and [6]-gingediacetate are also found in ginger extract.
Baojian Wu - One of the best experts on this subject based on the ideXlab platform.
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regioselective glucuronidation of Gingerols by human liver microsomes and expressed udp glucuronosyltransferase enzymes reaction kinetics and activity correlation analyses for ugt1a9 and ugt2b7
Journal of Pharmacy and Pharmacology, 2015Co-Authors: Zhufeng Wu, Baojian WuAbstract:Objectives To determine the reaction kinetics for regioselective glucuronidation of Gingerols (i.e. 6-, 8- and 10-Gingerol) by human liver microsomes and expressed UDP-glucuronosyltransferase (UGT) enzymes, and to identify the main UGT enzymes involved in regioselective glucuronidation of Gingerols. Methods The rates of glucuronidation were determined by incubating the Gingerols with uridine diphosphoglucuronic acid-supplemented microsomes. Kinetic parameters were derived by fitting an appropriate model to the data. Activity correlation analyses were performed to identify the main UGT enzymes contributing to hepatic metabolism of Gingerols. Key findings Glucuronidation at the 4′-OH group was much more favoured than that at 5-OH. The degree of position preference was compound-dependent; the catalytic efficiency ratios of 4′-O- to 5-O-glucuronidation were 9.1, 19.7 and 2.9 for 6-, 8- and 10-Gingerol, respectively. UGT1A8 (an intestinal enzyme), UGT1A9 and UGT2B7 were the enzymes showing the highest activity towards Gingerols. Formation of 5-O-glucuronide was mainly catalysed by UGT1A9. UGT2B7 was the only enzyme that generated glucuronides at both 4′-OH and 5-OH sites, although a strong position preference was observed with 4′-OH (≥80.2%). Further, activity correlation analyses indicated that UGT2B7 and UGT1A9 were primarily responsible for 4′-O-glucuronidation and 5-O-glucuronidation of Gingerols in the liver, respectively. Conclusions Gingerols were metabolized by multiple hepatic and gastrointestinal UGT enzymes. Also, UGT1A9 and 2B7 were the main contributors to regioselective glucuronidation of Gingerols in the liver.
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Regioselective glucuronidation of Gingerols by human liver microsomes and expressed UDP‐glucuronosyltransferase enzymes: reaction kinetics and activity correlation analyses for UGT1A9 and UGT2B7
Journal of Pharmacy and Pharmacology, 2014Co-Authors: Zhufeng Wu, Baojian WuAbstract:Objectives To determine the reaction kinetics for regioselective glucuronidation of Gingerols (i.e. 6-, 8- and 10-Gingerol) by human liver microsomes and expressed UDP-glucuronosyltransferase (UGT) enzymes, and to identify the main UGT enzymes involved in regioselective glucuronidation of Gingerols. Methods The rates of glucuronidation were determined by incubating the Gingerols with uridine diphosphoglucuronic acid-supplemented microsomes. Kinetic parameters were derived by fitting an appropriate model to the data. Activity correlation analyses were performed to identify the main UGT enzymes contributing to hepatic metabolism of Gingerols. Key findings Glucuronidation at the 4′-OH group was much more favoured than that at 5-OH. The degree of position preference was compound-dependent; the catalytic efficiency ratios of 4′-O- to 5-O-glucuronidation were 9.1, 19.7 and 2.9 for 6-, 8- and 10-Gingerol, respectively. UGT1A8 (an intestinal enzyme), UGT1A9 and UGT2B7 were the enzymes showing the highest activity towards Gingerols. Formation of 5-O-glucuronide was mainly catalysed by UGT1A9. UGT2B7 was the only enzyme that generated glucuronides at both 4′-OH and 5-OH sites, although a strong position preference was observed with 4′-OH (≥80.2%). Further, activity correlation analyses indicated that UGT2B7 and UGT1A9 were primarily responsible for 4′-O-glucuronidation and 5-O-glucuronidation of Gingerols in the liver, respectively. Conclusions Gingerols were metabolized by multiple hepatic and gastrointestinal UGT enzymes. Also, UGT1A9 and 2B7 were the main contributors to regioselective glucuronidation of Gingerols in the liver.
Stephen P Myers - One of the best experts on this subject based on the ideXlab platform.
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Gingerol content of diploid and tetraploid clones of ginger (Zingiber officinale Roscoe)
Journal of Agricultural and Food Chemistry, 2005Co-Authors: Hans Wohlmuth, Mike K. Smith, David N Leach, Stephen P MyersAbstract:Ginger (Zingiber officinale Roscoe), a monocotyledonous, sterile cultigen, is widely used as a spice, flavoring agent, and herbal medicine. The pungency of fresh ginger is due to a series of homologous phenolic ketones of which [6]-Gingerol is the major one. The Gingerols are thermally unstable and can be converted to their corresponding shogaols, which are present in dried ginger. Fresh rhizomes of 17 clones of Australian ginger, including commercial cultivars and experimental tetraploid clones, were assayed by HPLC for Gingerols and shogaols. [6]-Gingerol was identified as the major pungent phenolic compound in all samples, while [8]- and [10]-Gingerol occurred in lower concentrations. One cultivar known as “Jamaican” contained the highest concentrations of all three Gingerols and was the most pungent of the clones analyzed. Gingerols were stable in ethanolic solution over a 5-month period when stored at 4 °C. Shogaols were not identified in the extracts prepared from fresh rhizomes at ambient temperatu...
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Gingerol Content of Diploid and Tetraploid Clones of Ginger (Zingiber officinale Roscoe)
Journal of agricultural and food chemistry, 2005Co-Authors: Hans Wohlmuth, Mike K. Smith, David N Leach, Stephen P MyersAbstract:Ginger (Zingiber officinale Roscoe), a monocotyledonous, sterile cultigen, is widely used as a spice, flavoring agent, and herbal medicine. The pungency of fresh ginger is due to a series of homologous phenolic ketones of which [6]-Gingerol is the major one. The Gingerols are thermally unstable and can be converted to their corresponding shogaols, which are present in dried ginger. Fresh rhizomes of 17 clones of Australian ginger, including commercial cultivars and experimental tetraploid clones, were assayed by HPLC for Gingerols and shogaols. [6]-Gingerol was identified as the major pungent phenolic compound in all samples, while [8]- and [10]-Gingerol occurred in lower concentrations. One cultivar known as "Jamaican" contained the highest concentrations of all three Gingerols and was the most pungent of the clones analyzed. Gingerols were stable in ethanolic solution over a 5-month period when stored at 4 degrees C. Shogaols were not identified in the extracts prepared from fresh rhizomes at ambient temperature, confirming that these compounds are not native constituents of fresh ginger. In contrast to previous findings, this study did not find significant differences in Gingerol concentrations between the tetraploid clones and their parent diploid cultivar.
David W. Hoskin - One of the best experts on this subject based on the ideXlab platform.
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The Phenolic Gingerols and Gingerol-Derived Shogaols: Features and Properties Related to the Prevention and Treatment of Cancer and Chronic Inflammation
Polyphenols in Plants, 2019Co-Authors: Chao-yu Loung, Andrea Rasmussen, David W. HoskinAbstract:Abstract The root of the ginger plant (Zingiber officinale) is rich in bioactive phytochemicals, including phenolic Gingerols and Gingerol-derived shogaols responsible for many of the reported medicinal properties of ginger root extract. Gingerol homologs are differentiated based on the length of their unbranched alkyl side chain. The most abundant form of Gingerol in ginger root is 6-Gingerol, which when dehydrated yields 6-shogaol. The other Gingerol homologs are less abundant but, in many cases, are more potent. In this chapter, we review the current literature on Gingerols and shogaols in relation to their antioxidant, antiinflammatory, and anticancer properties that point to the potential use of these ginger phenolics for the prevention and/or treatment of cancer and other diseases associated with chronic inflammation. Gingerol and shogaol toxicity, pharmacokinetics, and interactions with other drugs are discussed in the context of their possible clinical utility. The molecular basis of the anticancer and antiinflammatory effects of Gingerols and shogaols are also described, which provides a strong rationale for further investigations of the medicinal effects of these ginger phenolics in preclinical models of cancer and various inflammatory disorders as a prelude to clinical trials.
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10 Gingerol a major phenolic constituent of ginger root induces cell cycle arrest and apoptosis in triple negative breast cancer cells
Experimental and Molecular Pathology, 2017Co-Authors: Megan M Bernard, Jason R Mcconnery, David W. HoskinAbstract:The ginger rhizome is rich in bioactive compounds, including [6]-Gingerol, [8]-Gingerol, and [10]-Gingerol; however, to date, most research on the anti-cancer activities of Gingerols have focused on [6]-Gingerol. In this study, we compared [10]-Gingerol with [8]-Gingerol and [6]-Gingerol in terms of their ability to inhibit the growth of human and mouse mammary carcinoma cells. A colorimetric assay based on the enzymatic reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide revealed that [10]-Gingerol was more potent than [6]-Gingerol and at least as potent as [8]-Gingerol for the inhibition of triple-negative human (MDA-MB-231, MDA-MB-468) and mouse (4T1, E0771) mammary carcinoma cell growth. Further investigation of [10]-Gingerol showed that it suppressed the growth of estrogen receptor-bearing (MCF-7, T47D) and HER2-overexpressing (SKBR3) breast cancer cells. The inhibitory effect of [10]-Gingerol on the growth of MDA-MB-231 cells was associated with a reduction in the number of rounds of cell division and evidence of S phase-cell cycle arrest, as well as induction of apoptosis due to mitochondrial outer membrane permeabilization and the release of proapoptotic mitochondrial cytochrome c and SMAC/DIABLO into the cytoplasm. Surprisingly, killing of MDA-MB-231 cells by [10]-Gingerol was not affected by a pan-caspase inhibitor (zVAD-fmk) or an anti-oxidant (N-acetylcysteine), suggesting that the cytotoxic effect of [10]-Gingerol did not require caspase activation or the accumulation of reactive oxygen species. These findings suggest that further investigation of [10]-Gingerol is warranted for its possible use in the treatment of breast cancer.
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differential inhibition of t lymphocyte proliferation and cytokine synthesis by 6 Gingerol 8 Gingerol and 10 Gingerol
Phytotherapy Research, 2015Co-Authors: Megan M Bernard, Suzanne J Furlong, Melanie Power R Coombs, David W. HoskinAbstract:[6]-Gingerol, [8]-Gingerol, and [10]-Gingerol are pungent components of fresh ginger, extracts of which inhibit various components of the inflammatory response. Because little is known regarding the effect of Gingerols with different unbranched alkyl side chain lengths on the activation and effector function of T lymphocytes, we compared the effects of [6]-Gingerol, [8]-Gingerol, and [10]-Gingerol on murine T lymphocyte proliferation, expression of CD25 and CD69 activation markers, cytokine synthesis, and interleukin (IL)-2 receptor signaling. All three Gingerols inhibited DNA synthesis by T lymphocytes, as well as interferon-γ synthesis. In contrast, only [8]-Gingerol and [10]-Gingerol inhibited CD25 and CD69 expression, and IL-2 synthesis. None of the Gingerols affected IL-4 synthesis. Exogenous IL-2 enhanced T lymphocyte proliferation in the presence of [6]-Gingerol but did not significantly increase T lymphocyte proliferation in the presence of [8]-Gingerol or [10]-Gingerol. In line with this finding, [8]-Gingerol and [10]-Gingerol impaired IL-2-induced proliferation of CTLL-2 cells, but constitutive CD25 expression was unaffected, indicating inhibition of IL-2 receptor signaling. In general, [10]-Gingerol and [8]-Gingerol were more potent inhibitors of T lymphocytes than [6]-Gingerol. Suppression of T lymphocyte responses by Gingerols suggests that these phytochemicals may be beneficial in chronic inflammatory conditions associated with excessive or inappropriate T lymphocyte activation. Copyright © 2015 John Wiley & Sons, Ltd.