Characterization of metabolites produced from the biotransformation of 6-shogaol formed by Aspergillus niger

Jo, Soo Kyung; Kim, In Sook; Rehman, Shaheed Ur; Ha, Sang Keun; Park, Ho-Young; Park, Yongkon; Yoo, Hye Hyun

doi:10.1007/s00217-015-2519-6

Cited by 14 publications

(7 citation statements)

References 21 publications

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“…[6]-paradol, the alkane derivative of [6]-shogaol, can be formed from [6]-shogaol through enzymatic reduction of the alkene bond ( Jo et al, 2016 ), although little has been published on the purported synthesis pathway in ginger. [6]-paradol is present in fresh and dried ginger ( Jolad et al, 2005 ; Nagendra chari et al, 2013 ), albeit at much lower concentrations compared to the gingerols and shogaols.…”

Section: Introductionmentioning

confidence: 99%

Pungent and volatile constituents of dried Australian ginger

Johnson

Mani

White

et al. 2021

Current Research in Food Science

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Ginger is well known for its pungent flavour and health-benefitting properties, both of which are imparted by various gingerol derivatives and other volatile constituents. Although there has been a considerable amount of research into the chemical constituents found in fresh ginger, there is little information available on the quality of Australian-grown dried ginger, particularly that intended for processing purposes. Here, we investigate differences in the chemical composition of three samples of processing-grade ginger, ranging from very poor to good quality. Gingerols and 6-shogaol were quantified using high performance liquid chromatograph (HPLC), while gas chromatography coupled with mass spectrometry (GC-MS) was used to identify and semi-quantify the volatile constituents and other gingerol derivatives. Significant differences were found between the samples in their content of gingerols and [6]-shogaol, as well as in their total phenolic content and antioxidant capacity. A total of 100 volatile compounds were identified in the dried ginger samples, including 54 terpenoid derivatives and 35 gingerol derivatives. Several compounds are reported from ginger for the first time, including limonene glycol and neryl laurate. In addition, we provide the second report of the presence of shyobunol, geranyl- p -cymene and geranyl-α-terpinene in ginger.

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Section: Introductionmentioning

confidence: 99%

Pungent and volatile constituents of dried Australian ginger

Johnson

Mani

White

et al. 2021

Current Research in Food Science

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“…6-Paradol is a metabolized product which is derived from 6-shogaol by liver enzyme ( Surh and Lee, 1992 , 1994 ). These two ingredients exert similar pharmacological activities including anti-oxidative and anti-inflammatory actions ( Nagendra chari et al ., 2013 ; Jo et al ., 2016 ). In addition, our previous in vivo study demonstrated that 6-shogaol and 6-paradol were neuroprotective against cerebral ischemia to the same extent ( Gaire et al ., 2015 ).…”

Section: Discussionmentioning

confidence: 99%

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

2019

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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 ( 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) peptide immunization with injection of pertussis toxin. Once-daily administration of 6-shogaol and 6-paradol (5 mg/kg/day, .) 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-α, 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.

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“…In our study, a total of two aromatic new compounds 1 and 2 were isolated as its major metabolites from Z. phillippsii that may be used for their chemical defense. The structures of isolated chemicals were closely related to the gingerol and shogaol analogues [16,17]. These compounds will be used as an important chemotaxonomical marker for the East Malaysian Z. phillippsii.…”

Section: Structure Elucidationmentioning

confidence: 94%