• Title/Summary/Keyword: shogaol

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Optimization of Extraction Conditions for the 6-Shogaol-rich Extract from Ginger (Zingiber officinale Roscoe)

  • Ok, Seon;Jeong, Woo-Sik
    • Preventive Nutrition and Food Science
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    • v.17 no.2
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    • pp.166-171
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    • 2012
  • 6-Shogaol, a dehydrated form of 6-gingerol, is a minor component in ginger (Zingiber officinale Roscoe) and has recently been reported to have more potent bioactivity than 6-gingerol. Based on the thermal instability of gingerols (their dehydration to corresponding shogaols at high temperature), we aimed to develop an optimal process to maximize the 6-shogaol content during ginger extraction by modulating temperature and pH. Fresh gingers were dried under various conditions: freeze-, room temperature (RT)- or convection oven-drying at 60 or $80^{\circ}C$, and extracted by 95% ethanol at RT, 60 or $80^{\circ}C$. The content of 6-shogaol was augmented by increasing both drying and extraction temperatures. The highest production of 6-shogaol was achieved at $80^{\circ}C$ extraction after drying at the same temperature and the content of 6-shogaol was about 7-fold compared to the lowest producing process by freezing and extraction at RT. Adjustment of pH (pH 1, 4, 7 and 10) for the 6-shogaol-richest extract (dried and extracted both at $80^{\circ}C$) also affected the chemical composition of ginger and the yield of 6-shogaol was maximized at the most acidic condition of pH 1. Taken together, the current study shows for the first time that a maximized production of 6-shogaol can be achieved during practical drying and extraction process of ginger by increasing both drying and extracting temperatures. Adjustment of pH to extraction solvent with strong acid also helps increase the production of 6-shogaol. Our data could be usefully employed in the fields of food processing as well as nutraceutical industry.

Optimization Study for the Production of 6-Shogaol-rich Ginger (Zingiber officinale Roscoe) under Conditions of Mild Pressure and High Temperature (가압조건에서 생강 유래 6-shogaol 변환을 위한 가열 조건 최적화)

  • Park, Ho-Young;Ha, Sang Keun;Choi, Jiwon;Choi, Hee-Don;Kim, Yoonsook;Park, Yongkon
    • Korean Journal of Food Science and Technology
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    • v.46 no.5
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    • pp.588-592
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    • 2014
  • Under optimized condition mild pressure in combination with specific temperature for heat treatment transform the 6-gingerol into 6-shogaol. The purpose of this study was to optimize the conditions used for heat treatment under pressure for increasing 6-shogaol content in ginger (Zingiber officinale Roscoe). A central composite experimental design was used to evaluate the effects of application temperature ($70-130^{\circ}C$) and temperature-holding time (95-265 min) on the transformation of 6-shogaol. The experimental values were shown to be in significantly good agreement with the predicted values (adjusted determination coefficient, $R^2{_{Adj}}=0.9857$). 6-Shogaol content increased as the application temperature and temperature-holding time increased. By analyzing the response surface plots, the optimum conditions of heat treatment (temperature and time) for increasing 6-shogaol content were found to be $127^{\circ}C$ and 109 min, respectively. Under these optimal conditions, the predicted 6-shogaol content was 3.98 mg/g dried ginger. The adequacy of the model equation for predicting the optimum response values was effectively verified by the validation data.

Neuroprotective Effects of 6-Shogaol and Its Metabolite, 6-Paradol, in a Mouse Model of Multiple Sclerosis

  • Sapkota, Arjun;Park, Se Jin;Choi, Ji Woong
    • Biomolecules & Therapeutics
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    • v.27 no.2
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    • pp.152-159
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    • 2019
  • Multiple sclerosis (MS) is an autoimmune disease characterized by progressive neuronal loss, neuroinflammation, axonal degeneration, and demyelination. Previous studies have reported that 6-shogaol, a major constituent of ginger (Zingiber officinale rhizome), and its biological metabolite, 6-paradol, have anti-inflammatory and anti-oxidative properties in the central nervous system (CNS). In the present study, we investigated whether 6-shogaol and 6-paradol could ameliorate against experimental autoimmune encephalomyelitis (EAE), a mouse model of MS elicited by myelin oligodendrocyte glycoprotein ($MOG_{35-55}$) peptide immunization with injection of pertussis toxin. Once-daily administration of 6-shogaol and 6-paradol (5 mg/kg/day, p.o.) to symptomatic EAE mice significantly alleviated clinical signs of the disease along with remyelination and reduced cell accumulation in the white matter of spinal cord. Administration of 6-shogaol and 6-paradol into EAE mice markedly reduced astrogliosis and microglial activation as key features of immune responses inside the CNS. Furthermore, administration of these two molecules significantly suppressed expression level of tumor necrosis $factor-{\alpha}$, a major proinflammatory cytokine, in EAE spinal cord. Collectively, these results demonstrate therapeutic efficacy of 6-shogaol or 6-paradol for EAE by reducing neuroinflammatory responses, further indicating the therapeutic potential of these two active ingredients of ginger for MS.

Optimization of drying conditions for the conversion of 6-gingerol to 6-shogaol under subcritical water extraction from ginger (아임계수 추출에서 6-gingerol의 6-shogaol 전환을 위한 생강 건조 조건 최적화)

  • Ko, Min-Jung;Nam, Hwa-Hyun;Chung, Myong-Soo
    • Korean Journal of Food Science and Technology
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    • v.51 no.5
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    • pp.447-451
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    • 2019
  • 6-gingerol can be converted to 6-shogaol, one of the predominant active compounds found in ginger, via processing such as drying and extraction. Subcritical water extraction is the environmentally friendly method of extraction of bioactive compounds using only purified water as a solvent. This study investigated subcritical water extraction ($190^{\circ}C$, 15 min) of 6-gingerol, and 6-shogaol from dried ginger (Zingiber officinale) including drying conditions such as temperature (room temperature, 60, $80^{\circ}C$, and freeze drying) and time duration for drying (1-4 h). The amount of 6-gingerol was found to be reduced, and that of 6-shogaol was found to be increased depending upon the water content of dried ginger. Upon oven-drying ginger at $60^{\circ}C$ for 2 h, the maximum yields of 6-gingerol ($0.18{\pm}0.02mg/g$ fresh weight), and 6-shogaol ($0.47{\pm}0.02mg/g$ fresh weight) were obtained upon subcritical water extraction.

6-Shogaol reduces progression of experimental endometriosis in vivo and in vitro via regulation of VGEF and inhibition of COX-2 and PGE2-mediated inflammatory responses

  • Wang, Dan;Jiang, Yiling;Yang, Xiaoxin;Wei, Qiong;Wang, Huimin
    • The Korean Journal of Physiology and Pharmacology
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    • v.22 no.6
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    • pp.627-636
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    • 2018
  • Endometriosis (EM) is one of the most common gynaecological disorder affecting women in their reproductive age. Mechanisms involved in the pathogenesis of EM remains poorly understood, however inflammatory responses have been reported to be significantly involved. The efficacy of 6-shogaol on proliferation of endometriotic lesions and inflammatory pathways in experimentally-induced EM model was explored in this study. EM was stimulated in Sprague-Dawley rats by implantation of autologous endometrium onto the peritoneum abdominal wall. Separate groups were treated with 6-shogaol (50, 100 or 150 mg/kg b.wt/day) via oral gavage for one month period. Gestrinone (GTN) group received GTN (0.5 mg/kg/day) as positive control. Five weeks after implantation, the spherical volume of ecto-uterine tissues was determined. Treatment with 6-shogaol significantly reduced the implant size. Histological analysis reported atrophy and regression of the lesions. 6-shogaol administration effectively down-regulated $NF-{\kappa}B$ signaling, VEGF and VEGFR-2 (Flk-1) expression in the endometriotic lesions. Excess production of $IL-1{\beta}$ and IL-6 (pro-inflammatory cytokines), PGE2 and nitric oxide (NO) were reduced. Overall, the results of the study reveal the efficacy of 6-shogaol against endometriosis via effectively suppressing proliferation of the lesions and modulating angiogenesis and $COX-2/NF-{\kappa}B$-mediated inflammatory cascades.

Effects of 6-Shogaol, A Major Component of Zingiber officinale Roscoe, on Human Cytochrome P450 Enzymes in vitro (생강의 주성분인 6-Shogaol이 인체 약물대사효소인 Cytochrome P450에 미치는 영향)

  • Kim, Jin
    • Korean Journal of Medicinal Crop Science
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    • v.24 no.1
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    • pp.7-13
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    • 2016
  • Background : Ginger has been extensively used in foods and traditional medicines in Asian countries. Despite its frequent consumption in daily life, the mechanism of potential interactions between ginger components-drug has not been examined. To elucidate the mechanism of governing the effects of 6-shogaol, a primary constituent of dried ginger, on human cytochrome P450 (CYP) isoenzymes an incubation studies were carried out using pooled human liver microsome (HLM). Methods and Results : CYP isoenzyme specific substrate was incubated with multiple concentrations of inhibitor, HLM and cofactors. 6-shogaol showed a potent inhibitory effect on CYP2C9, CYP1A2 and CYP2C19 with half maximal inhibitory concentration ($IC_{50}$) values of 29.20, 20.68 and $18.78{\mu}M$ respectively. To estimate the value of the inhibition constant ($K_i$) and the mode of inhibition, an incubation study with varying concentrations of each CYP isoenzyme-specific probe was performed. 6-shogaol inhibited CYP2C9 and CYP2C19 noncompetitively ($K_i=29.02$ and $19.26{\mu}M$ respectively), in contrast, the inhibition of CYP1A2 was best explained by competitive inhibition ($K_i=6.33{\mu}M$). Conclusions : These findings suggest that 6-shogaol may possess inhibitory effects on metabolic activities mediated by CYP1A2, CYP2C9 and CYP2C19 in humans.

Inhibition of Homodimerization of Toll-like Receptor 4 by 6-Shogaol

  • Ahn, Sang-Il;Lee, Jun-Kyung;Youn, Hyung-Sun
    • Molecules and Cells
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    • v.27 no.2
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    • pp.211-215
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    • 2009
  • Toll-like receptors (TLRs) play a critical role in sensing microbial components and inducing innate immune and inflammatory responses by recognizing invading microbial pathogens. Lipopolysaccharide-induced dimerization of TLR4 is required for the activation of downstream signaling pathways including nuclear factor-kappa B ($NF-{\kappa}B$). Therefore, TLR4 dimerization may be an early regulatory event in activating ligand-induced signaling pathways and induction of subsequent immune responses. Here, we report biochemical evidence that 6-shogaol, the most bioactive component of ginger, inhibits lipopolysaccharide-induced dimerization of TLR4 resulting in the inhibition of $NF-{\kappa}B$ activation and the expression of cyclooxygenase-2. Furthermore, we demonstrate that 6-shogaol can directly inhibit TLR-mediated signaling pathways at the receptor level. These results suggest that 6-shogaol can modulate TLR-mediated inflammatory responses, which may influence the risk of chronic inflammatory diseases.

Biodegradation Mechanism of Shogaol by Aspergillus niger (Aspergillus niger에 의한 Shogaol의 생분해 메카니즘)

  • 고인경;이상섭
    • YAKHAK HOEJI
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    • v.27 no.1
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    • pp.29-36
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    • 1983
  • Shogaol, one of the main pungent principles of the rhizome of Zingiber officinale, Roscoe, was biodegraded by Aspergillus niger to produce two main metabolites. The crystalline metabolite obtained after silicic acid column chromatography was proved to be 1-(4-hydroxy-3- methoxyphenyl)decan-10-ol-3-one. The oily metabolite obtained after prolonged fermentation was 1-(4-hydroxy-3-methoxyphenyl)-decan-3, 10-diol. The results suggest that shogaol should be biodegraded to 1-(4-hydroxy-3-methoxyphenyl)-dec-4-en-10-ol-3-one or to 1-(4-hydroxy-3-methoxyphenyl)-decan-3-one, and to 1-(4-hydroxy-3-methoxyphenyl)-decan-10-ol-3-one then to 1-(4-hydroxy-3-methoxyphenyl)-decan-3, 10-diol and finally to carbon dioxide and water.

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Suppression of the Expression of Cyclooxygenase-2 Induced by Toll-like Receptor 2, 3, and 4 Agonists by 6-Shogaol (6-Shogaol의 Toll-like receptor 2, 3, 4 agonists에 의해서 유도된 cyclooxygenase-2 발현 억제)

  • Kim, Jeom-Ji;An, Sang-Il;Lee, Jeon-Su;Yun, Sae-Mi;Lee, Mi-Yeong;Yun, Hyeong-Seon
    • Korean Journal of Food Science and Technology
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    • v.40 no.3
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    • pp.332-336
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    • 2008
  • Ginger is widely used as a traditional herbal medicine. Both ginger and its extracts have been used to treat many chronic inflammatory conditions via the inhibition of nuclear factor-kappa B (NF-${\kappa}B$) activation, which results in the suppression of cyclooxygenase-2 (COX-2) expression. However, the mechanisms as to how ginger extracts mediate their health effects are largely unknown. Toll-like receptors (TLRs) trigger anti-microbial innate immune responses, recognizing conserved microbial structural molecules that are known as pathogen-associated molecular patterns. All TLR signaling pathways culminate in the activation of NF-${\kappa}B$. The activation of NF- ${\kappa}B$ leads to the induction of inflammatory gene products, including cytokines and COX-2. This study reports the biochemical evidence that 6-shogaol, an active compound in ginger, inhibits NF-${\kappa}B$ activation and COX-2 expression induced by TLR2, TLR3, and TLR4 agonists. Furthermore, 6-shogaol inhibited NF-${\kappa}B$ activation induced by the following downstream signaling components of the TLRs: MyD88, $IKK{\beta}$, and p65. These results imply that ginger can modulate immune responses that could potentially modify the risk of many chronic inflammatory diseases.