Effect of a Labile Methyl Donor on the Transformation of 5-Demethyltangeretin and the Related Implication on Bioactivity

Ting, Yuwen; Li, Colin C.; Pan, Min‐Hsiung; Ho, Chi‐Tang

doi:10.1021/jf400562p

Cited by 13 publications

(13 citation statements)

References 41 publications

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“…Even so, challenges in the application of PMFs and hydroxylated PMFs as nutraceuticals in functional foods still exist because of the very low water solubility caused by methoxyl groups, which consequently leads to low bioavailability when ingested orally. Ting et al generated an emulsion system by using phosphotidylcholine as the emulsifier, and tangeretin and 5‐demethyltangeretin were incorporated in emulsion‐based delivery systems . They showed that the emulsion promoted faster lipid digestion kinetics, which resulted in a higher total solubilized PMF level, whereas 5‐demethyltangeretin was found to transform into its permethoxylated counterpart and yield lower levels of solubilized 5‐demethyltangeretin.…”

Section: Bioavailability and Biotransformation Of Hydroxylated Pmfsmentioning

confidence: 99%

“…The tangeretin emulsion caused better cytotoxicity than the DMSO dissolved form, but this result was not observed with 5‐demethyltangeretin emulsion. The authors concluded that the interaction between 5‐demethyltangeretin and the formulation material (lecithin in this case) caused excessive transformation of 5‐demethyltangeretin into tangeretin thus resulting in lower bioactivity . Later, Zheng et al used an oil‐in‐water emulsion system (composed of 10% oil phase and 90% aqueous phase) to encapsulate 5‐demethyltangeretin.…”

Section: Bioavailability and Biotransformation Of Hydroxylated Pmfsmentioning

confidence: 99%

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Disease chemopreventive effects and molecular mechanisms of hydroxylated polymethoxyflavones

Lai

et al. 2015

BioFactors

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Recent increasing attention in research of polymethoxyflavones (PMFs) from Citrus genus because of their wide range of biological properties has been reported in various studies. Hydroxylated PMFs are unique flavones and recognized as the methoxy group of PMFs that is substituted for hydroxyl one. Hydroxylated PMFs are naturally existed in citrus peel and other plants as well as occurred as metabolites of their PMFs counterparts. Several in vitro and in vivo studies have documented the chemopreventive effects of hydroxylated PMFs including anti-cancer, anti-inflammation, anti-atherosclerosis, and neuroprotection. They function to regulate cell death, proliferation, differentiation, repair, and metabolism through acting on modulation of signaling cascade, gene transcription, and protein function and enzyme activity. The mechanisms of action of hydroxylated PMFs in disease chemoprevention depend on their structure, the number, and position of hydroxyl group. Although the efficacy of hydroxylated PMFs in chemoprevention and the oral bioavailability requires further investigation, they still provide great promise for improving human health. This review highlights the recent published data of hydroxylated PMFs with chemopreventive potential and the underlying mechanism involved.

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Section: Bioavailability and Biotransformation Of Hydroxylated Pmfsmentioning

confidence: 99%

Section: Bioavailability and Biotransformation Of Hydroxylated Pmfsmentioning

confidence: 99%

Disease chemopreventive effects and molecular mechanisms of hydroxylated polymethoxyflavones

Lai

et al. 2015

BioFactors

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“…The in vitro lipolysis study was carried out using our method previously published . To be consistent with the other bioavailability study in this work, a fasted-state buffer was selected for this part of the evaluation.…”

Section: Methodsmentioning

confidence: 99%

“…In our previous study, a tangeretin-containing viscoelastic emulsion (VE) system was optimized to achieve higher formulation loading, good stability, and suitable particle size . The aqueous solubility and in vitro anticancer proliferation of tangeretin were significantly improved when processed into the VE formulation. , …”

Section: Introductionmentioning

confidence: 99%

Viscoelastic Emulsion Improved the Bioaccessibility and Oral Bioavailability of Crystalline Compound: A Mechanistic Study Using in Vitro and in Vivo Models

et al. 2015

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The oral bioavailability of hydrophobic compound is usually limited by the poor aqueous solubility in the gastrointestinal (GI) tract. Various oral formulations were developed to enhance the systemic concentration of such molecules. Moreover, compounds with high melting temperature that appear as insoluble crystals imposed a great challenge to the development of oral vehicle. Polymethoxyflavone, an emerging category of bioactive compounds with potent therapeutic efficacies, were characterized as having a hydrophobic and highly crystalline chemical structure. To enhance the oral dosing efficiency of polymethoxyflavone, a viscoelastic emulsion system with a high static viscosity was developed and optimized using tangeretin, one of the most abundant polymethoxyflavones found in natural sources, as a modeling compound. In the present study, different in vitro and in vivo models were used to mechanistically evaluate the effect of emulsification on oral bioavailability of tangeretin. In vitro lipolysis revealed that emulsified tangeretin was digested and became bioaccessible much faster than unprocessed tangeretin oil suspension. By simulating the entire human GI tract, TNO's gastrointestinal model (TIM-1) is a valuable tool to mechanistically study the effect of emulsification on the digestion events that lead to a better oral bioavailability of tangeretin. TIM-1 result indicated that tangeretin was absorbed in the upper GI tract. Thus, a higher oral bioavailability can be expected if the compound becomes bioaccessible in the intestinal lumen soon after dosing. In vivo pharmacokinetics analysis on mice again confirmed that the oral bioavailability of tangeretin increased 2.3 fold when incorporated in the viscoelastic emulsion than unformulated oil suspension. By using the combination of in vitro and in vivo models introduced in this work, the mechanism that underlie the effect of viscoelastic emulsion on the oral bioavailability of tangeretin was well-elucidated.

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“…Having two nonpolar fatty acid tails and a polar phosphate-choline head, lecithin was reported to contribute good hydration property to the emulsion system as well as being employed as a steric and electrostatic stabilizer [14]. In conjunction with the fact that it is natural, fully biocompatible, and generally recognized as safe, lecithin, with no doubt, has become a popular emulsifier to stabilize the colloidal system in recent years [15]. Successful cases of using lecithin for the development of nanoemulsion have been described in numerous preceding publications [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Making Concentrated Pterostilbene Highly Bioavailable in Pressure Processed Phospholipid Nanoemulsion

Sun

Chou

et al. 2021

Processes

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Pterostilbene, a dimethylether analog of resveratrol, has been found to have potent biological activity. However, the bioavailability of pterostilbene in the biological system is limited due to its poor solubility in an aqueous environment. A nanoemulsion system was designed for this purpose. Lecithin-based nanoemulsion was formed after 3 cycles through a high-pressure homogenizer at 500 psi. The rheological properties and particle size were measured using dynamic light scattering and a viscometer. The storage stabilities of the prepared formulation were determined based on its ability to maintain its particle size and loading concentration. According to the experimental results, the lecithin-based nanoemulsion system contained approximately 9.5% of pterostilbene. Over the 28-day stability test, the particle size, zeta potential, and encapsulation of pterostilbene in the nanoemulsion did not change significantly, indicating good storage stability. The positive effect of the prepared nanoemulsion system on bioavailability was studied and confirmed using in vitro lipolysis and a caco-2 monolayer model.

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Effect of a Labile Methyl Donor on the Transformation of 5-Demethyltangeretin and the Related Implication on Bioactivity

Cited by 13 publications

References 41 publications

Disease chemopreventive effects and molecular mechanisms of hydroxylated polymethoxyflavones

Disease chemopreventive effects and molecular mechanisms of hydroxylated polymethoxyflavones

Viscoelastic Emulsion Improved the Bioaccessibility and Oral Bioavailability of Crystalline Compound: A Mechanistic Study Using in Vitro and in Vivo Models

Making Concentrated Pterostilbene Highly Bioavailable in Pressure Processed Phospholipid Nanoemulsion

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