Identification and biological evaluation of flavonoids from the fruits of Prunus mume.

Abstract

This Letter describes the identification of potent antioxidant and anti-osteoporosis agents from the fruits of Prunus mume. From the methanol extract, a novel flavan dimer, characterized as 2β,3β-epoxy-5,7,4'-trihydroxyflavan-(4α→8)-epicatechin (1), was isolated along with five known flavonoids (2-6). Their structures were determined based on extensive spectroscopic analysis, including IR, HRESIMS, 1D- and 2D-NMR, and CD spectra. The antioxidant activities of compounds 1-6 were evaluated in terms of their peroxyl radical-scavenging (Trolox equivalent) and reducing capacities. All isolates showed potent peroxyl radical-scavenging and reducing activities at concentrations of 1-10 μM. Among them, compounds 1 and 2 were the most active at 1 μM. Anti-osteoporosis activities were investigated using both murine osteoblastic MC3T3-E1 cells and osteoclastic RAW 264.7 cells. Compounds 2, 3, and 6 significantly stimulated the differentiation of osteoblastic MC3T3-E1 cells to increase collagen synthesis or mineralization functions of osteoblasts. Compounds 1, 3, 4, and 6 significantly suppressed tartrate-resistant acid phosphatase (TRAP) activity in receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclastic RAW 264.7 macrophage cells.

• Authors: Xi-Tao Yan, Wei Li, Ya-Nan Sun, Seo-Young Yang, Sang-Hyun Lee, Jian-Bo Chen, Hae-Dong Jang, Young-Ho Kim
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 24 Issue 5 Pg. 1397-402 (Mar 01 2014) ISSN: 1464-3405 [Electronic] England
• PMID: 24485782 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2014 Elsevier Ltd. All rights reserved.

Chemical References

• Antioxidants
• Flavonoids
• Free Radicals
• Isoenzymes
• RANK Ligand
• Collagen
• Acid Phosphatase
• Acp5 protein, mouse
• Tartrate-Resistant Acid Phosphatase

Topics

• Acid Phosphatase (metabolism)
• Animals
• Antioxidants (chemistry, isolation & purification, pharmacology)
• Cell Differentiation (drug effects)
• Cell Line
• Collagen (biosynthesis)
• Flavonoids (chemistry, isolation & purification, pharmacology)
• Free Radicals (chemistry)
• Fruit (chemistry, metabolism)
• Isoenzymes (metabolism)
• Magnetic Resonance Spectroscopy
• Mice
• Molecular Conformation
• Prunus (chemistry, metabolism)
• RANK Ligand (pharmacology)
• Tartrate-Resistant Acid Phosphatase