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Updated: Apr 27, 2026

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade

Published on: August 14, 2019

Flavanones from Miconia prasina.

Amer H Tarawneh¹, Francisco León¹, Mohammed A Ibrahim²

¹Department of Medicinal Chemistry, The University of Mississippi, University, MS 38677, USA.

Phytochemistry Letters

|July 1, 2014

Summary

This summary is machine-generated.

Researchers isolated miconioside C, a novel flavanone glycoside, and other compounds from Miconia prasina stems. These compounds were analyzed using NMR and mass spectrometry, with some tested for cannabinoid receptor binding.

Keywords:

Melastomataceae Miconia prasina cannabinoids receptors flavanone flavanone glycoside

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Area of Science:

Natural Product Chemistry
Phytochemistry
Pharmacognosy

Background:

Miconia prasina is a plant species with potential for novel compound discovery.
Flavanones and their glycosides represent a class of natural products with diverse biological activities.

Purpose of the Study:

To isolate and characterize chemical constituents from the stems of Miconia prasina.
To evaluate the in vitro binding activity of isolated compounds against cannabinoid receptors (CB1 and CB2).

Main Methods:

Isolation of compounds using methanolic extraction.
Structure elucidation primarily through comprehensive Nuclear Magnetic Resonance (NMR) spectroscopy (1H NMR, 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC) and mass spectrometry.
In vitro binding assays for cannabinoid receptors (CB1 and CB2).

Main Results:

Isolation and identification of six compounds: miconioside C (1), 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranosylmatteucinol (2), miconioside B (3), matteucinol (4), farrerol (5), and desmethoxymatteucinol (6).
Miconioside C (1) is a newly identified glycosidic flavanone.
Compounds 1-3 were assessed for their binding affinities to CB1 and CB2 receptors.

Conclusions:

The study successfully identified several compounds from Miconia prasina, including a novel flavanone glycoside.
The preliminary evaluation of compounds 1-3 provides a basis for further investigation into their potential interactions with cannabinoid systems.