Journal ArticleDOI
Glucuronidation and its impact on the bioactivity of [6]-shogaol.
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TLDR
Compared with 6S, the glucuronidation of 6S largely eliminated its cell cytotoxicity against human colon cancer cell lines HT-116 and HT-29, and its Nrf2-inducing activity.Abstract:
cope
: 6-shogaol (6S) from ginger has been reported to have diverse bioactivities and can be widely metabolized in animals and humans; however, the impact of glucuronidation on its bioactivity is still largely unknown. This study investigates the glucuronidation of 6S and its effect on cell cytotoxicity and Nrf2-inducing activities of 6S.
Methods and Results
: The glucuronidated metabolite of 6S, 4-O-monoglucuronide 6S (6S-G), was synthesized and characterized for the first time. Glucuronidation of 6S in humans was studied using microsomes of the liver and intestine and recombinant UGTs. The kinetics of 6S glucuronidation by human liver and intestinal microsomes followed the substrate inhibition kinetics model. The intrinsic glucuronidation clearance (CLint) of 6S in human liver microsomes was higher than that in human intestine microsomes. Among the recombinant UGTs examined, UGT1A1, 1A3, 1A6, 1A8, 1A10, 2B7, 2B15, and 2B17 exhibited glucuronidation activity toward 6S, with UGT2B7 being the most potent one. Compared with 6S, the glucuronidation of 6S largely eliminated its cell cytotoxicity against human colon cancer cell lines HT-116 and HT-29, and its Nrf2-inducing activity.
Conclusion
: The findings from current study provide foundations for understanding the role of glucuronidation in biotransformation and biological activities of 6S.
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Citations
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Journal ArticleDOI
Occurrence, biological activity and metabolism of 6-shogaol
Xingran Kou,Xingran Kou,Xiaoqi Wang,Ruya Ji,Lang Liu,Yening Qiao,Zaixiang Lou,Chaoyang Ma,Shiming Li,Hongxin Wang,Chi-Tang Ho +10 more
TL;DR: The conjugation of the α,β-unsaturated ketone skeleton in the chemical structure of 6-shogaol explicates its higher potency and efficacy than 6-gingerol in terms of antioxidant, anti-inflammatory, anticancer, antiemetic and other bioactivities.
Journal ArticleDOI
A recent update on the multifaceted health benefits associated with ginger and its bioactive components
Run-Hui Ma,Run-Hui Ma,Zhi-Jing Ni,Zhi-Jing Ni,Yun-Yang Zhu,Yun-Yang Zhu,Kiran Thakur,Kiran Thakur,Fan Zhang,Yuan-Yuan Zhang,Fei Hu,Fei Hu,Jian-Guo Zhang,Jian-Guo Zhang,Zhao-Jun Wei,Zhao-Jun Wei,Zhao-Jun Wei +16 more
TL;DR: The pharmacological potential of ginger is summarized and its consumption may reduce or delay the progression of related diseases, such as cancer, diabetes, and obesity, via modulation of genetic and metabolic activities.
Journal ArticleDOI
Metabolic Profiles of Ginger, A Functional Food, and Its Representative Pungent Compounds in Rats by Ultraperformance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry.
Liangliang He,Zifei Qin,Mengsen Li,Zilin Chen,Chen Zeng,Zhihong Yao,Yang Yu,Yi Dai,Xin-Sheng Yao +8 more
TL;DR: The metabolic profiles of ginger in rats were systemically investigated by UPLC-Q/TOF-MS and indicated that the in vivo effective components of ginger were mainly derived from [ 6]-gingerol and [6]-shogaol.
Journal ArticleDOI
Glucuronidation and its effect on the bioactivity of amentoflavone, a biflavonoid from Ginkgo biloba leaves.
Lili Gan,Jiating Ma,Guoquan You,Jinxia Mai,Zhaoyu Wang,Ruopeng Yang,Cong Xie,Jingrao Fei,Lan Tang,Jie Zhao,Zheng Cai,Ling Ye +11 more
TL;DR: Ginkgo biloba leaves contain amentoflavone (AMF), a dietary flavonoid that possesses antioxidant and anticancer activity that is extensively subjected to glucuronidation.
Journal ArticleDOI
Interindividual Variability in Metabolism of [6]-Shogaol by Gut Microbiota.
TL;DR: This is the first report involving the identification of the microbial metabolites of 6S in an in vitro fermentation system, and the first demonstration of the critical role of gut microbiota in producing the bioactive free form of 7S and its metabolites in the intestinal tract in mice.
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