title: Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa.
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 IC50values from 0.2 to 10.2 μM.
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.|Department of Chemistry Education, Faculty of Education, Tanjungpura University , 78124 Pontianak, Indonesia.
authors.forename: Rini
authors.initials: R
authors.lastname: Muharini
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.
authors.forename: Adriana
authors.initials: A
authors.lastname: Díaz
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.|Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University , Mansoura 35516, Egypt.
authors.forename: Weaam
authors.initials: W
authors.lastname: Ebrahim
authors.affiliation: Department of Organic Chemistry, University of Debrecen , Debrecen 4032, Hungary.
authors.forename: Attila
authors.initials: A
authors.lastname: Mándi
authors.affiliation: Department of Organic Chemistry, University of Debrecen , Debrecen 4032, Hungary.
authors.forename: Tibor
authors.initials: T
authors.lastname: Kurtán
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.
authors.forename: Nidja
authors.initials: N
authors.lastname: Rehberg
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Kalscheuer
authors.affiliation: Institute of Complex Systems: Strukturbiochemie, Forschungszentrum Juelich , 52428 Juelich, Germany.
authors.forename: Rudolf
authors.initials: R
authors.lastname: Hartmann
authors.affiliation: Department of Pharmacognosy, Faculty of Pharmacy, King Saud University , Riyadh, Saudi Arabia.
authors.forename: Raha S
authors.initials: RS
authors.lastname: Orfali
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Peking University , Beijing 100191, People's Republic of China.
authors.forename: Wenhan
authors.identifier: 0000-0002-4978-4083
authors.initials: W
authors.lastname: Lin
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.
authors.forename: Zhen
authors.identifier: 0000-0003-3314-7853
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.
authors.forename: Peter
authors.initials: P
authors.lastname: Proksch
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007887:Fabaceae / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008223:Lymphoma / Q000737:chemistry / Q000188:drug therapy*; D051379:Mice; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D007529:Isoflavones; D010636:Phenols; D010936:Plant Extracts