Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities
Open Access
- 15 July 2015
- Vol. 20 (7) , 12787-12803
Abstract
Rhododendron formosanum is an endemic species distributed in the central mountains of Taiwan. In this study, the biological activities of major procyanidins isolated from the leaf extract of R. formosanum were investigated. Four compounds, including two procyanidin dimers, procyanidin A1 (1) and B3 (2), and two procyanidin trimmers, procyanidin C4 (4) and cinnamtannin D1 (5), were isolated and identified on the basis of spectroscopic data. The structure of a new procyanidin dimer, rhodonidin A (3), was elucidated by 2D-NMR, CD spectrum and MS. The procyanidin trimmers and rhodonidin A are reported for the first time in Ericaceae. The biological activities of these procyanidins were evaluated using anti-bacterial and anti-oxidative assays. Only the new compound 3 demonstrated strong anti-bacterial activity against Staphylococcus aureus at an MIC value of 4 μg/mL. All compounds showed pronounced antioxidant activities and the activities are enhanced as the amount of OH groups in procyanidins increased. In conclusion, the pleiotropic effects of procyanidins isolated from the leaves of R. formosanum can be a source of promising compounds for the development of future pharmacological applications.Keywords
Funding Information
- Ministry of Science and Technology, Taiwan (MOST 103-2811-B-039-020)
- National Science Council (NSC 102-2811-B-039-005, NSC 102-2313-B-039-001-MY3)
This publication has 28 references indexed in Scilit:
- A-Type Proanthocyanidins from the Stems of Ephedra sinica (Ephedraceae) and Their Antimicrobial ActivitiesMolecules, 2013
- Antioxidant Activity and Proanthocyanidin Profile of Selliguea feei RhizomesMolecules, 2013
- Characterization of Proanthocyanidins in Stems of Polygonum multiflorum Thunb as Strong Starch Hydrolase InhibitorsMolecules, 2013
- Bioactive A-Type Proanthocyanidins from Cinnamomum cassiaJournal of Natural Products, 2011
- The main and modified CUPRAC methods of antioxidant measurementTrAC Trends in Analytical Chemistry, 2011
- Cranberry Proanthocyanidins Mediate Growth Arrest of Lung Cancer Cells through Modulation of Gene Expression and Rapid Induction of ApoptosisMolecules, 2011
- Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. The Effect of 4-Alkoxy Group of Catechin Electrophile in the Yb(OTf)3-Catalyzed Condensation with Catechin NucleophileThe Journal of Organic Chemistry, 2010
- Biosynthesis and Genetic Regulation of Proanthocyanidins in PlantsMolecules, 2008
- Two isomeric epoxysitosterols from Rhododendron formosanum: 1H and 13C NMR chemical shift assignmentsMagnetic Resonance in Chemistry, 2006
- Standardized Methods for the Determination of Antioxidant Capacity and Phenolics in Foods and Dietary SupplementsJournal of Agricultural and Food Chemistry, 2005