Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits ofAmorpha fruticosa
- 11 January 2017
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 80 (1) , 169-180
Abstract
Fourteen new natural products, namely, 2-[(Z)-styryl]-5-geranylresorcin-1-carboxylic acid (1), amorfrutin D (2), 4-O-demethylamorfrutin D (3), 8-geranyl-3,5,7-trihydroxyflavanone (4), 8-geranyl-5,7,3′-trihydroxy-4′-methoxyisoflavone (5), 6-geranyl-5,7,3′-trihydroxy-4′-methoxyisoflavone (6), 8-geranyl-7,3′-dihydroxy-4′-methoxyisoflavone (7), 3-O-demethyldalbinol (8), 6a,12a-dehydro-3-O-demethylamorphigenin (9), (6aR,12aR,5′R)-amorphigenin (10), amorphispironones B and C (11 and 12), resokaempferol 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside (13), and daidzein 7-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (14), together with 40 known compounds, were isolated from the fruits of Amorpha fruticosa. The structures of the new compounds were elucidated by 1D and 2D NMR spectroscopic analysis as well as from the mass spectrometry data. ECD calculations were performed to determine the absolute configurations of 11 and 15. Compounds 1, 4–6, and 16–23 showed potent to moderate antibacterial activities against several Gram-positive bacteria with MIC values ranging from 3.1 to 100 μM. In addition, compounds 11 and 24–33 were significantly cytotoxic against the L5178Y mouse lymphoma cell line and exhibited IC50 values from 0.2 to 10.2 μM.Keywords
Funding Information
- Bundesministerium für Forschung, Technologie und Raumfahrt
- European Regional Development Fund (GINOP-2.3.2-15-2016-00008)
- Direktorat Jenderal Pendidikan Tinggi
This publication has 66 references indexed in Scilit:
- ECD cotton effect approximated by the Gaussian curve and other methodsChirality, 2009
- Kaempferol Glycosides from Lobularia maritima and Their Potential Role in Plant InteractionsChemistry & Biodiversity, 2009
- Phenolic Constituents of Amorpha fruticosa That Inhibit NF-κB Activation and Related Gene ExpressionJournal of Natural Products, 2008
- Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cellsCytotechnology, 2006
- Essential Oil ofAmorpha fruticosaL.Journal of Essential Oil Research, 2001
- Dimethylchromene rotenoids from Tephrosia candidaPhytochemistry, 1997
- Novel Bioactive Cubé Insecticide Constituents: Isolation and Preparation of 13-homo-13-Oxa-6a,12a-dehydrorotenoidsThe Journal of Organic Chemistry, 1997
- Structural Elucidation and Chemical Conversion of Amorphispironone, a Novel Spironone from Amorpha fruticosa, to Rotenoids.Chemical and Pharmaceutical Bulletin, 1993
- Rotenoids and 7,2,'4',5'-Tetramethoxyisoflavone in Amorpha fruticosa L. FruitsPlanta Medica, 1980
- Total Synthesis of (±)-Sermundone and An Alternative Cyclization Method to DehydrorotenoidstAgricultural and Biological Chemistry, 1972