Biotransformed product, genistein 7-O-phosphate, enhances the oral bioavailability of genistein

Wang, Shang-Ta; Fang, Ting-Fang; Hsu, Chen; Chen, Chia-Hao; Lin, Chien-Ching; Su, Nan‐Wei

doi:10.1016/j.jff.2015.01.008

Cited by 19 publications

(20 citation statements)

References 55 publications

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“…The rats were deprived of food but given access to water for 24 h before experiments and were randomly divided into five groups ( n = 5) for further oral gavage administration with Hst aqueous suspension, Hsd aqueous suspension, G-Hsd solution, Hst7P solution, and Hst3′P solution. The dosage of the tested compounds used in this experiment was 22.8 μmol/kg body weight, which was translated from a commonly used dosage of Hsd dietary supplement products for humans, 500 mg/day, by body-surface-area normalization. ,, After oral administration, 400 μL of blood sample was collected in heparinized microcentrifuge tubes via the jugular vein at various times and then centrifuged at 4 °C under 3000 g to obtain plasma. The content of Hst in plasma samples was determined using a UPLC-MS/MS system (Acquity UPLC-Quattro Premier XE MS system, Waters Co., Milford, MA).…”

Section: Methodsmentioning

confidence: 99%

“…In a previous study, we reported a phosphorylated genistein, namely, genistein 7- O- phosphate, derived from Bacillus subtilis var. natto BCRC 80517 bioconversion with genistein. , The bioavailability of the water-soluble phosphate derivatives of genistein was superior to that of aglyconic genistein . We further incubated the microbe with Hst and found two Hst phosphate derivatives (HstPs), namely, Hst 7- O -phosphate (Hst7P) and Hst3′- O -phosphate (Hst3′P), generated in the culture broth (Figure ).…”

Section: Introductionmentioning

confidence: 99%

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Microbial Phosphorylation Product of Hesperetin by Bacillus subtilis BCRC 80517 Improves Oral Bioavailability in Rats

Wang

Chen

Hsu

et al. 2021

J. Agric. Food Chem.

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The flavanoid hesperidin (Hsd) is one of the major polyphenols in citrus fruits. Hsd and its aglycone hesperetin (Hst) have a broad array of bioactivities; however, their low aqueous solubility and low intestinal permeability lead to their limited oral bioavailability. In the present study, we generated two water-soluble derivatives of Hst, namely, Hst 7-O-phosphate and Hst3′-O-phosphate, by a unique bioconversion process of Bacillus subtilis var. natto BCRC80517. The phosphorylated products showed superior aqueous solubility and distinct physicochemical properties compared with the original Hst. The Hst phosphate derivatives (HstPs) remained stable in simulated gastric and intestinal fluids for 240 min and could revert to the original Hst form by alkaline phosphatase treatment in Caco-2 cells, showing enhanced intestinal permeability in vitro. After oral administration in rats, HstPs greatly elevated plasma exposure to Hst and showed better bioavailability than did Hsd. HstPs may be a potential and efficient alternative to Hst.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Microbial Phosphorylation Product of Hesperetin by Bacillus subtilis BCRC 80517 Improves Oral Bioavailability in Rats

Wang

Chen

Hsu

et al. 2021

J. Agric. Food Chem.

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“…In soybean flavonoids, genistein is a natural isoflavone in the family of secondary plant metabolites, which possesses well-known preventive activity in breast and prostate cancer, cardiovascular diseases, and postmenopausal problems [3]. However, the low water solubility and intestinal permeability may lead to its poor oral bioavailability [4]. …”

Section: Introductionmentioning

confidence: 99%

Non-digestible stachyose promotes bioavailability of genistein through inhibiting intestinal degradation and first-pass metabolism of genistein in mice

Lin

et al. 2017

Food & Nutrition Research

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This study was designed to explore the molecular mechanism of stachyose in enhancing the gastrointestinal stability and absorption of soybean genistein in mice. Male Kunming mice in each group (n = 8) were administered by intragastric gavage with saline, stachyose (250 mg/kg·bw), genistein (100 mg/kg·bw), and stachyose (50, 250, and 500 mg/kg·bw) together with genistein (100 mg/kg·bw) for 4 consecutive weeks, respectively, and then their urine, feces, blood, gut, and liver were collected. UPLC-qTOF/MS analysis showed that levels of genistein and its metabolites (dihydrogenistein, genistein 7-sulfate sodium salt, genistein 4’-β-D-glucuronide, and genistein 7-β-D-glucuronide) in serum and urine were increased with an increase in stachyose dosages in mice. Furthermore, the feces level of genistein aglycone was also elevated by co-treatment of stachyose with genistein. However, the feces concentration of dihydrogenistein, a characteristic metabolite of genistein by gut microorganism, was decreased by stachyose administration in a dose-dependent manner. Additionally, the simultaneous administration with stachyose and genistein in mice could decrease intestinal SULT, UGT, P-gp, and MRP1 expression, relative to the treatment with individual stachyose or genistein. These results demonstrate that stachyose-mediated inhibition against the intestinal degradation of genistein and expression of phase II enzymes and efflux transporters can largely contribute to the elevated bioavailability of soybean genistein.

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“…Wang and co-workers added phosphate groups into genistein to form genistein-O-phosphatidic acid. The solubility of genistein-O-phosphatidic acid in water, permeability of small intestine and thus genistein plasma concentration were greatly enhanced [622]. Moreover, stability of genistein against metabolism was enhanced by methylating the free hydroxymethyl group of genistein [623].…”

Section: Formulations and Delivery Systemsmentioning

confidence: 99%

Plant-Derived Natural Products in Cancer Research: Extraction, Mechanism of Action, and Drug Formulation

et al. 2020

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Cancer is one of the main causes of death globally and considered as a major challenge for the public health system. The high toxicity and the lack of selectivity of conventional anticancer therapies make the search for alternative treatments a priority. In this review, we describe the main plant-derived natural products used as anticancer agents. Natural sources, extraction methods, anticancer mechanisms, clinical studies, and pharmaceutical formulation are discussed in this review. Studies covered by this review should provide a solid foundation for researchers and physicians to enhance basic and clinical research on developing alternative anticancer therapies.

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Biotransformed product, genistein 7-O-phosphate, enhances the oral bioavailability of genistein

Cited by 19 publications

References 55 publications

Microbial Phosphorylation Product of Hesperetin by Bacillus subtilis BCRC 80517 Improves Oral Bioavailability in Rats

Microbial Phosphorylation Product of Hesperetin by Bacillus subtilis BCRC 80517 Improves Oral Bioavailability in Rats

Non-digestible stachyose promotes bioavailability of genistein through inhibiting intestinal degradation and first-pass metabolism of genistein in mice

Plant-Derived Natural Products in Cancer Research: Extraction, Mechanism of Action, and Drug Formulation

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