An update on polyphenol disposition via coupled metabolic pathways

Wang, Liping; Sun, Rongjin; Zhang, Qisong; Luo, Qianqian; Zeng, Shi; Li, Xiaoyan; Gong, Xia; Li, Yuhuan; Lu, Linlin; Hu, Ming; Liu, Zhongqiu

doi:10.1080/17425255.2019.1559815

Cited by 20 publications

(14 citation statements)

References 105 publications

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“…How did the delayed ingestion of CJ inhibit the elimination of S-warfarin? The pharmacokinetics of polyphenols showed rapid and extensive metabolism to form conjugated metabolites, such as glucuronides and sulfates, which were acids existing as anions in the body, and their excretions were mediated by transporters, such as the BCRP and MRPs [ 34 ]. These conjugated metabolites were probable inhibitors of the BCRP.…”

Section: Discussionmentioning

confidence: 99%

Bidirectional Influences of Cranberry on the Pharmacokinetics and Pharmacodynamics of Warfarin with Mechanism Elucidation

Yang

Hsu

et al. 2021

Nutrients

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Cranberry is a dietary supplement popularly used for the prophylaxis of urinary tract infection. Interestingly, cranberry–warfarin interactions in clinical reports have shown bidirectional outcomes. (±) Warfarin, a widely prescribed anticoagulant, but with a narrow therapeutic index, contains equal amounts of S- and R-warfarin, of which S-warfarin is more active. The aim of this study was to investigate the effects of different ingestion times of cranberry on the pharmacokinetics and pharmacodynamics of warfarin. Rats were orally administered (±) warfarin (0.2 mg/kg) with and without cranberry (5.0 g/kg) at 0.5 h prior to the warfarin, and at 10 h after the warfarin. The plasma concentrations of S- and R-warfarin were determined by LC/MS. The results indicate that cranberry ingested at 0.5 h before (±) warfarin significantly decreased the systemic exposures of S-warfarin and R-warfarin. Conversely, when cranberry was ingested at 10 h after (±) warfarin, the elimination of S-warfarin was significantly inhibited, and the anticoagulation effect of (±) warfarin was significantly enhanced. The results of the mechanism studies indicate that cranberry activated the breast cancer resistance protein (BCRP), which mediated the efflux transports of S-warfarin and R-warfarin. Moreover, the metabolites of cranberry inhibited cytochrome P450 (CYP) 2C9, the main metabolizing enzyme for S-warfarin. In conclusion, cranberry affected the pharmacokinetics of (±) warfarin in a bidirectional manner by activating the BCRP by CJ during absorption and inhibiting the BCRP and CYP2C9 by CMs during elimination, depending on the ingestion time of CJ. The combined use of cranberry with warfarin should be avoided.

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Section: Discussionmentioning

confidence: 99%

Bidirectional Influences of Cranberry on the Pharmacokinetics and Pharmacodynamics of Warfarin with Mechanism Elucidation

Yang

Hsu

et al. 2021

Nutrients

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“…The XRPD pattern of raw taxifolin is characterized by peaks at 2θ 7. 16 5a). Taxifolin microtubes have a similar XRPD pattern when compared to raw taxifolin, but nevertheless are not identical (Figure 5b).…”

Section: X-ray Analysismentioning

confidence: 98%

“…Flavonoids are well known as bioactive compounds [12][13][14][15]. Implementation of these materials in medical practice is restricted by the limited water solubility and low bioavailability of flavonoids [16]. Researchers have attempted to modify the properties of these compounds via developing new polymorphic forms using crystal engineering [17].…”

Section: Introductionmentioning

confidence: 99%

Assembling the Puzzle of Taxifolin Polymorphism

et al. 2020

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A large amount of the current literature dedicated to solid states of active pharmaceutical ingredients (APIs) pays special attention to polymorphism of flavonoids. Taxifolin (also known as dihydroquercetin) is an example of a typical flavonoid. Some new forms of taxifolin have been reported previously, however it is still unclear whether they represent polymorphic modifications. In this paper, we tried to answer the question about the taxifolin polymorphism. Taxifolin microtubes and taxifolin microspheres were synthesized from raw taxifolin API using several methods of crystal engineering. All forms were described with the help of spectral methods, scanning electron microscopy (SEM), X-ray powder diffraction (XRPD), and thermal analysis (TA). SEM reveals that the morphology of the solid phase is very specific for each sample. Although XRPD patterns of raw taxifolin and microtubes look similar, their TA profiles differ significantly. At the same time, raw taxifolin and microspheres have nearly identical thermograms, while XRPD shows that the former is a crystalline and the latter is an amorphous substance. Only the use of complex analyses allowed us to put the puzzle together and to confirm the polymorphism of taxifolin. This article demonstrates that taxifolin microtubes are a pseudopolymorphic modification of raw taxifolin.

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“…In enteric recycling, the flavone glucuronides are hydrolyzed back to aglycones, which then are rapidly absorbed or are re-converted back to conjugates (glucuronides, sulfates) and either effluxed to the intestinal lumen or absorbed into the blood via the colon [78]. A part of the phase II metabolites (conjugates) reaching the liver via the portal vein enter enterohepatic recycling: they are excreted via the bile into the gut, where they may be further recycled by the same pathways [79,80,81] (Figure 3). Although it has been traditionally held that glucuronides excreted in the gut through the bile are chiefly of hepatic origin, because hepatocytes generally do not take up significant amounts of glucuronides of exogenous substances, it has been demonstrated for several flavonoids, including chrysin, that glucuronides recycled enterohepatically are of extrahepatic origin [82].…”

Section: Recyclingmentioning

confidence: 99%

Pharmacokinetics of B-Ring Unsubstituted Flavones

et al. 2019

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B-ring unsubstituted flavones (of which the most widely known are chrysin, baicalein, wogonin, and oroxylin A) are 2-phenylchromen-4-one molecules of which the B-ring is devoid of any hydroxy, methoxy, or other substituent. They may be found naturally in a number of herbal products used for therapeutic purposes, and several have been designed by researchers and obtained in the laboratory. They have generated interest in the scientific community for their potential use in a variety of pathologies, and understanding their pharmacokinetics is important for a grasp of their optimal use. Based on a comprehensive survey of the relevant literature, this paper examines their absorption (with deglycosylation as a preliminary step) and their fate in the body, from metabolism to excretion. Differences among species (inter-individual) and within the same species (intra-individual) variability have been examined based on the available data, and finally, knowledge gaps and directions of future research are discussed.

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An update on polyphenol disposition via coupled metabolic pathways

Cited by 20 publications

References 105 publications

Bidirectional Influences of Cranberry on the Pharmacokinetics and Pharmacodynamics of Warfarin with Mechanism Elucidation

Bidirectional Influences of Cranberry on the Pharmacokinetics and Pharmacodynamics of Warfarin with Mechanism Elucidation

Assembling the Puzzle of Taxifolin Polymorphism

Pharmacokinetics of B-Ring Unsubstituted Flavones

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