The Experts below are selected from a list of 438 Experts worldwide ranked by ideXlab platform
Ikhlas A Khan - One of the best experts on this subject based on the ideXlab platform.
-
two undescribed Paradol related specialized metabolites from aframomum melegueta
Natural Product Research, 2020Co-Authors: Zhihao Zhang, Fazila Zulfiqar, Ikhlas A KhanAbstract:AbstractAframomum melegueta seeds are widely used as a spice in Africa. Two undescribed Paradol-related compounds, (S)−9-hydroxy-[6]-Paradol (1) and (9S)−3,9-dihydroxydihydro-[6]-Paradol (2) togeth...
-
Two undescribed Paradol-related specialized metabolites from Aframomum melegueta.
Natural product research, 2020Co-Authors: Zhihao Zhang, Fazila Zulfiqar, Zulfiqar Ali, Ikhlas A KhanAbstract:Aframomum melegueta seeds are widely used as a spice in Africa. Two undescribed Paradol-related compounds, (S)-9-hydroxy-[6]-Paradol (1) and (9S)-3,9-dihydroxydihydro-[6]-Paradol (2) together with eight reported constituents (3-10) were isolated and characterised from the methanol extract of A. melegueta seeds. Structure elucidation of these metabolites was achieved by means of NMR and mass spectroscopic data analyses. The absolute configuration of undescribed compounds (1 and 2) was determined using the modified Mosher's method.
Zhihao Zhang - One of the best experts on this subject based on the ideXlab platform.
-
two undescribed Paradol related specialized metabolites from aframomum melegueta
Natural Product Research, 2020Co-Authors: Zhihao Zhang, Fazila Zulfiqar, Ikhlas A KhanAbstract:AbstractAframomum melegueta seeds are widely used as a spice in Africa. Two undescribed Paradol-related compounds, (S)−9-hydroxy-[6]-Paradol (1) and (9S)−3,9-dihydroxydihydro-[6]-Paradol (2) togeth...
-
Two undescribed Paradol-related specialized metabolites from Aframomum melegueta.
Natural product research, 2020Co-Authors: Zhihao Zhang, Fazila Zulfiqar, Zulfiqar Ali, Ikhlas A KhanAbstract:Aframomum melegueta seeds are widely used as a spice in Africa. Two undescribed Paradol-related compounds, (S)-9-hydroxy-[6]-Paradol (1) and (9S)-3,9-dihydroxydihydro-[6]-Paradol (2) together with eight reported constituents (3-10) were isolated and characterised from the methanol extract of A. melegueta seeds. Structure elucidation of these metabolites was achieved by means of NMR and mass spectroscopic data analyses. The absolute configuration of undescribed compounds (1 and 2) was determined using the modified Mosher's method.
Jiro Takata - One of the best experts on this subject based on the ideXlab platform.
-
Pharmacokinetics of Paradol Analogues Orally Administered to Rats.
Journal of agricultural and food chemistry, 2016Co-Authors: Shuichi Setoguchi, Akinori Haratake, Daisuke Watase, Kazuhisa Matsunaga, Nami Nagata-akaho, Jiro TakataAbstract: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 (AUC0–24h) of the parent compounds decreased with increasing acyl chain length. Whereas 12-Paradol showed the largest AUC0–24h with the longest time to reach its maximum plasma concentration of all of the compounds tested, the AUC0–24h 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.
-
Relationship between the acyl chain length of Paradol analogues and their antiobesity activity following oral ingestion.
Journal of agricultural and food chemistry, 2014Co-Authors: Akinori Haratake, Daisuke Watase, Shuichi Setoguchi, Kazuki Terada, Kazuhisa Matsunaga, Jiro TakataAbstract:6-Paradol is known to activate thermogenesis in brown adipose tissue (BAT), and Paradol analogues with different acyl chain lengths possess different pungency thresholds. In this study, the influence of the acyl chain length on the antiobesity activity of the Paradol analogues was investigated. The antiobesity activity of 6-Paradol in mice fed a high-fat diet for 8 weeks was greater than that of dihydrocapsiate. A comparison of the antiobesity activities of zingerone and 6-Paradol showed that the length of the acyl chain in the Paradol analogue was important for strong activity. Furthermore, the antiobesity activities of 6-, 8-, and 12-Paradol appeared to decrease in an acyl chain length-dependent manner. The mechanism of the antiobesity activity of 6-Paradol was enhanced by increasing levels of energy metabolism in the BAT, as well as an increase in the expression of uncoupling proteins 1 via the activation of sympathetic nerve activity.
Fazila Zulfiqar - One of the best experts on this subject based on the ideXlab platform.
-
two undescribed Paradol related specialized metabolites from aframomum melegueta
Natural Product Research, 2020Co-Authors: Zhihao Zhang, Fazila Zulfiqar, Ikhlas A KhanAbstract:AbstractAframomum melegueta seeds are widely used as a spice in Africa. Two undescribed Paradol-related compounds, (S)−9-hydroxy-[6]-Paradol (1) and (9S)−3,9-dihydroxydihydro-[6]-Paradol (2) togeth...
-
Two undescribed Paradol-related specialized metabolites from Aframomum melegueta.
Natural product research, 2020Co-Authors: Zhihao Zhang, Fazila Zulfiqar, Zulfiqar Ali, Ikhlas A KhanAbstract:Aframomum melegueta seeds are widely used as a spice in Africa. Two undescribed Paradol-related compounds, (S)-9-hydroxy-[6]-Paradol (1) and (9S)-3,9-dihydroxydihydro-[6]-Paradol (2) together with eight reported constituents (3-10) were isolated and characterised from the methanol extract of A. melegueta seeds. Structure elucidation of these metabolites was achieved by means of NMR and mass spectroscopic data analyses. The absolute configuration of undescribed compounds (1 and 2) was determined using the modified Mosher's method.
Young-joon Surh - One of the best experts on this subject based on the ideXlab platform.
-
Induction of apoptosis and caspase-3 activation by chemopreventive [6]-Paradol and structurally related compounds in KB cells.
Cancer letters, 2002Co-Authors: Young Sam Keum, Jin Kim, Keun Hyung Lee, Kwang Kyun Park, Young-joon Surh, Jong-min Lee, Sang Sup Lee, Jung Hoon Yoon, So Yeon Joo, In Ho ChaAbstract:[6]-Paradol, a pungent phenolic substance found in ginger and other Zingiberaceae plants, has been demonstrated to be an effective inhibitor of tumor promotion in mouse skin carcinogenesis. In the present study, we found that [6]-Paradol and other structurally related derivatives, [10]-Paradol, [3]-dehydroParadol, [6]-dehydroParadol, and [10]-dehydroParadol, with the exception of [3]-Paradol induce apoptosis in an oral squamous carcinoma cell line, KB, in a dose-dependent manner. [10]-Paradol and [10]-dehydroParadol exhibited a similar extent of cytotoxicity to that of [6]-Paradol. [6]-DehydroParadol and [3]-dehydroParadol appeared to be more potent, with an IC50 less than 40 microM. Treatment of KB cells with an apoptosis-inducing concentration of [6]-dehydroParadol caused induction of proteolytic cleavage of pro-caspase-3. These results suggest that [6]-Paradol and structurally related derivatives induce apoptosis through a caspase-3-dependent mechanism.
-
Antioxidative and antitumor promoting effects of [6]-Paradol and its homologs
Mutation Research-genetic Toxicology and Environmental Mutagenesis, 2001Co-Authors: Won Yoon Chung, Sang Sup Lee, Young-joon Surh, Yeon Joo Jung, Kwang Kyun ParkAbstract:Abstract Recently, considerable attention is focused on anti-carcinogenic phytochemicals, particularly those derived from medicinal or edible plants. [6]-Paradol, a pungent phenolic compound present in certain Zingiberaceae plants, is known to have antimicrobial and analgesic activities. The compound has been reported to attenuate promotion of skin carcinogenesis and TPA-induced ear edema in female ICR mice, and to induce apoptosis in cultured human promyelocytic leukemia (HL-60) cells. In this study, we performed several biochemical studies to evaluate and compare the cancer chemopreventive potential of [6]-Paradol and its synthetic derivatives. [6]-Paradol and its synthetic nonpungent analog, [6]-dehydroParadol significantly decreased the incidence and the multiplicity of skin tumors initiated by 7,12-dimethylbenz[a]anthracene (DMBA) and promoted by 12-O-tetradecanoylphorbol-13-acetate (TPA). Topical application of [6]-Paradol and its derivatives inhibited TPA-induced ear edema and H2O2 production and myeloperoxidase activity in the dorsal skin of mice. Induction of TPA-induced mouse epidermal ornithine decarboxylase (ODC) activity and H2O2- and UV-induced formation of oxidized DNA bases in vitro were also attenuated by the above compounds. These results indicate that [6]-Paradol and its derivatives possess the cancer chemopreventive potential.
-
Induction of apoptosis in HL-60 cells by pungent vanilloids, [6]-gingerol and [6]-Paradol
Cancer letters, 1998Co-Authors: Eunyong Lee, Young-joon SurhAbstract:[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.
-
Enzymatic reduction of shogaol: a novel biotransformation pathway for the alpha,beta-unsaturated ketone system.
Biochemistry international, 1992Co-Authors: Young-joon Surh, Sang Sup LeeAbstract:A novel reductive metabolism of 1-(4-hydroxy-3-methoxyphenyl)-deca-4-ene-3-one (shogaol), a pungent principle of ginger, was investigated in rat liver in vitro. Ethyl acetate-extractable metabolites of shogaol formed by incubation of this alpha,beta-unsaturated ketone with rat liver cytosolic fraction fortified with NADPH or NADPH-generating system were isolated, and two major metabolites were identified as 1-(4-hydroxy-3-methoxyphenyl)-decan-3-one (Paradol) and 1-(4-hydroxy-3-methoxy)-decan-3-ol (reduced Paradol). 1-(4-hydroxy-3-methoxyphenyl)-deca-1-ene-3-one (dehydroParadol), a non-pungent analog of shogaol, formed the same metabolites as did shogaol under similar incubation conditions. Paradol appears to be an intermediate in the reductive metabolism of the alpha,beta-unsaturated ketone moiety of shogaol to the corresponding saturated alcohol.
