Inhibitory Activity of Bioactive Phloroglucinols from the Rhizomes of Dryopteris crassirhizoma on Escherichia coli β-Glucuronidase: Kinetic Analysis and Molecular Docking Studies

Abstract

Phloroglucinols—one of the major secondary metabolites in Dryopteris crassirhizoma—exhibit various pharmacological effects, such as antiviral, antioxidant, and antidiabetic activities. This study evaluated 30 phloroglucinols isolated from the rhizomes of D. crassirhizoma for their inhibitory activity on β-glucuronidase via in vitro assays. Among them, dimeric phloroglucinols 13–15 moderately inhibited β-glucuronidase, and trimeric phloroglucinols 26–28 showed strong inhibitory effects, with IC50 values ranging from 5.6 to 8.0 μM. Enzyme kinetic analysis confirmed all six active compounds to be in a competitive mode of inhibition. Molecular docking simulations revealed the key binding interactions with the active site of β-glucuronidase protein and the binding mechanisms of these active metabolites. Our results suggest that the rhizomes of D. crassirhizoma and trimeric compounds 26–28 may serve as potential candidates for discovering and developing new β-glucuronidase inhibitors.

Potential Health Benefits of Fruits and Vegetables II

“…This study highlights the potential health benefits of the metabolites found in B. karatas fruits [7]. Then, Phong et al (2022) isolated eight known secondary metabolites, including two isocoumarins and six coumarins, from the stems and branches of Acer mono Maxim. Their structures were confirmed using nuclear magnetic resonance spectroscopy and comparing the results to published reports.…”

Optimization of Ultrasonic-Assisted Extraction of α-Glucosidase Inhibitors from Dryopteris crassirhizoma Using Artificial Neural Network and Response Surface Methodology

“…Thus, this compound was tested at different concentrations to determine its IC 50 value. Previous studies reported that trimeric phloroglucinol nortrisflavaspidic acid ABB (2) exhibited the significant inhibition of PTP1B and β-glucuronidase, with IC 50 values of 1.19 ± 0.13 and 8.0 ± 1.8 µM, respectively [5,6]. In this study, nortrisflavaspidic acid ABB (2) demonstrated a strong inhibitory effect against α-glucosidase, with an IC 50 value of 34.0 ± 0.14 µM, stronger than that of the positive control acarbose (IC 50 = 329.2 ± 0.35 µM).…”

“…Dryopteris crassirhizoma Nakai is a semi-evergreen plant that is widely distributed in China, South Korea, and Japan; the root of this plant is used in the Chinese Pharmacopoeia to cure viral disease and verminosis [1]. Recent studies revealed many pharmacological effects of this plant such as anti-cancer, antioxidant, anti-inflammatory, protein tyrosine phosphatase 1B (PTP1B), and β-glucuronidase inhibitory activities [2][3][4][5][6]. Previous phytochemical investigations of the rhizomes of D. crassirhizoma demonstrated the presence of various components, including phloroglucinols, flavonoids, and triterpenes [5,6].…”

“…Recent studies revealed many pharmacological effects of this plant such as anti-cancer, antioxidant, anti-inflammatory, protein tyrosine phosphatase 1B (PTP1B), and β-glucuronidase inhibitory activities [2][3][4][5][6]. Previous phytochemical investigations of the rhizomes of D. crassirhizoma demonstrated the presence of various components, including phloroglucinols, flavonoids, and triterpenes [5,6]. Phloroglucinols, principal chemical constituents of the isolate from D. crassirhizoma, exhibit a multitude of pharmacological activities.…”

Insights into the inhibitory activities of neolignans and diarylnonanoid derivatives from nutmeg ( Myristica fragrans Houtt.) seeds on soluble epoxide hydrolase using in vitro and in silico approaches

“…In Asian countries, natural products and herbal medicine have a longstanding history of being utilised for the treatment of various diseases because of their safety and low risk of side effects 11 . Nutmeg ( Myristica fragrans Houtt.…”