Sulfonation of curcuminoids: Characterization and contribution of individual SULT enzymes

Lu, Xiaoyue; Jiang, Kunyu; Han, Long; Zhang, Maofan; Zhou, Yu; Ma, Y.; Zhou, Yanfang; Meng, Shengnan

doi:10.1002/mnfr.201400493

Cited by 12 publications

(13 citation statements)

References 36 publications

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“…Herein, genistein-7-glucoside has a higher affinity for β-glucosidase than quercetin-4′-glucoside thus the former shows a higher deglycosylation rate, whereas some other glycosides such as quercetin-3,4′-diglucoside, quercetin-3-glucoside, kaempferol-3-glucoside, quercetin-3-rhamnoglucoside, and naringenin-7-rhamnoglucoside prefer to remain unchanged (Day et al, 1998). This intracellular reaction is regarded as a vital way to expose hydroxyl group of xenobiotics for further conjugation Cheng et al (1999), Margaillan et al (2015), Wong et al (2009), Finel et al (2005), King et al (1999), Mostaghel et al (2016), King et al (2000), Teubner et al (2007), Cheng et al (1998), Cheng et al (1999), Barbier et al (2000), Knights et al (2013), Chimalakonda et al (2011), Riches et al (2009), Ghosh et al (2013), Sakamoto et al (2015), Lu et al (2015), Guidry et al (2017), Kurogi et al (2017),…”

Section: Phase II Metabolism In Enterocytesmentioning

confidence: 99%

Bioaccessibility and bioavailability of phenolic compounds

Shahidi¹,

Peng²

2018

JFB

151

120

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Modern epidemiological and interventional studies have demonstrated that various bioactivities including antioxidant, antiproliferative, immune-regulatory, hormonal-regulation abilities and neuro-/hepato-/cardioprotective effects result from consumption of a phenolic-rich diet. The health benefits of ingesting phenolics are greatly dependent on their bioaccessibility and bioavailability in the digestive tract and circulatory system. This contribution attempts to review the bioaccessibility and bioavailability of phenolic compounds by focusing on the body’s internal mechanism including digestion, absorption, transport, modification, excretion, and colonic fermentation. The bioaccessibility and bioavailability of different phenolics vary depending on the physical condition of an individual, including digestive/absorptive/metabolic/response capability and effective dose. External factors such as processing methods and interaction with various food matrices also play a vital role on the bioavailability of dietary phenolic compounds. On the other hand, some novel phenolics have been synthesized to enable them rendering new bioactivities. The key internal factors influencing the bioaccessibility and bioavailability are also reviewed in this contribution. In addition, suggestions have been made for future measurement and assessment of bioavailability, together with prospects for food/nutraceutical/pharmaceutical application of novel phenolics.

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Section: Phase II Metabolism In Enterocytesmentioning

confidence: 99%

Bioaccessibility and bioavailability of phenolic compounds

Shahidi¹,

Peng²

2018

JFB

151

120

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“…Up to now, it is not known which of the SULT enzymes are responsible for the observed differences in curcumin sulfation between the two breast cancer lines. A very recent work showed that SULT1A3, SULT1C4, and SULT1E1 are the major isoforms catalyzing sulfation of curcumin; SULT1A1 and SULT2A1 demonstrated lower formation rates [23]. RT-PCR analysis in our lab revealed that only SUL-T1A1 mRNA levels were significantly higher in ZR-75-1 cells whereas SULT1A3 is equally expressed.…”

Section: Discussionmentioning

confidence: 56%

Metabolism of Curcumin in Human Breast Cancer Cells: Impact of Sulfation on Cytotoxicity

et al. 2017

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Curcumin is a natural polyphenol with promising anticancer properties that undergoes pronounced metabolism in humans. In order to determine whether metabolism of curcumin also occurs in tumor cells and whether biotransformation has any impact on cytotoxicity, metabolism experiments were conducted with hormone-dependent ZR-75-1 and hormone-independent MDA-MB-231 human breast cancer cells. By using HPLC-ESI-Qq-TOF-MS, it was possible to identify one main metabolite, namely curcumin sulfate, in both cell lines. Its concentration in the cytoplasm and culture medium was 1.6- to 1.7-fold higher in ZR-75-1 cells than in MDA-MB-231 cells, concomitant with a 2-fold higher IC value in the ZR-75-1 cell line (14 µM compared to 7.3 µM). The net result of sulfation seems to lower the intracellular concentration of curcumin, thereby decreasing its growth inhibitory activity. Interestingly, for the first time, we also found the formation of a curcumin dimer in the cytoplasm but not in the cellular medium of both cell lines. Compared to curcumin sulfate, however, its maximal intracellular concentrations were up to 4-fold lower, indicating only a minor contribution to the overall curcumin clearance. In conclusion, our data elucidated the metabolism of curcumin in breast cancer cells, which must be considered in humans following oral uptake of dietary curcumin as a chemopreventive agent.

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“…According to the reports, the enzyme that mediated drug sulfonation has a small binding pocket for binding flavonoids in a limited number of restrictive orientations; as a result, sulfonation only occurs at one hydroxyl position of flavonoids. [30,31] This strong regioselective sulfonation is different from UGT-mediated flavonoid glucuronidation. One UGT isoform (e.g.…”

Section: Discussionmentioning

confidence: 99%

Glucuronidation and its effect on the bioactivity of amentoflavone, a biflavonoid from Ginkgo biloba leaves

Gan

You

et al. 2020

Journal of Pharmacy and Pharmacology

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Objectives Ginkgo biloba leaves contain amentoflavone (AMF), a dietary flavonoid that possesses antioxidant and anticancer activity. Flavonoids are extensively subjected to glucuronidation. This study aimed to determine the metabolic profile of AMF and the effect of glucuronidation on AMF bioactivity. Methods A pharmacokinetic study was conducted to determine the plasma concentrations of AMF and its metabolites. The metabolic profile of AMF was elucidated using different species of microsomes. The antioxidant activity of AMF metabolites was determined using DPPH/ABTS radical and nitric oxide assays. The anticancer activity of AMF metabolites was evaluated in U87MG/U251 cells. Key findings Pharmacokinetic studies indicated that the oral bioavailability of AMF was 0.06 ± 0.04%, and the area under the curve of the glucuronidated AMF metabolites (410.938 ± 62.219 ng/ml h) was significantly higher than that of AMF (194.509 ± 16.915 ng/ml h). UGT1A1 and UGT1A3 greatly metabolized AMF. No significant difference was observed in the antioxidant activity between AMF and its metabolites. The anticancer activity of AMF metabolites significantly decreased. Conclusions A low AMF bioavailability was due to extensive glucuronidation, which was mediated by UGT1A1 and UGT1A3. Glucuronidated AMF metabolites had the same antioxidant but had a lower anticancer activity than that of AMF.

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Sulfonation of curcuminoids: Characterization and contribution of individual SULT enzymes

Abstract: This investigation contributed to elucidate the SULT-mediated metabolism and detoxication of curcuminoids at molecular levels and in different organs.

Cited by 12 publications

References 36 publications

Bioaccessibility and bioavailability of phenolic compounds

Bioaccessibility and bioavailability of phenolic compounds

Metabolism of Curcumin in Human Breast Cancer Cells: Impact of Sulfation on Cytotoxicity

Glucuronidation and its effect on the bioactivity of amentoflavone, a biflavonoid from Ginkgo biloba leaves

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