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      Screening of Panamanian Plant Extracts for Pesticidal Properties and HPLC-Based Identification of Active Compounds

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          Abstract

          A library of 600 taxonomically diverse Panamanian plant extracts was screened for fungicidal, insecticidal, and herbicidal activities. A total of 19 active extracts were submitted to HPLC-based activity profiling, and extracts of Bocconia frutescens, Miconia affinis, Myrcia splendens, Combretum aff. laxum, and Erythroxylum macrophyllum were selected for the isolation of compounds. Chelerythrine ( 2), macarpine ( 3), dihydrosanguinarine ( 5), and arjunolic acid ( 8) showed moderate-to-good fungicidal activity. Myricetin-3- O-(6’’- O-galloyl)-β-galactopyranoside ( 13) showed moderate insecticidal activity, but no compound with herbicidal activity was identified.

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          Most cited references42

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          Natural products that have been used commercially as crop protection agents.

          Many compounds derived from living organisms have found a use in crop protection. These compounds have formed the basis of chemical synthesis programmes to derive new chemical products; they have been used to identify new biochemical modes of action that can be exploited by industry-led discovery programmes; some have been used as starting materials for semi-synthetic derivatives; and many have been used or continue to be used directly as crop protection agents. This review examines only those compounds derived from living organisms that are currently used as pesticides. Plant growth regulators and semiochemicals have been excluded from the review, as have living organisms that exert their effects by the production of biologically active secondary metabolites. Copyright 2007 Society of Chemical Industry.
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            Flavonol 3-O-glycosides series of Vitis vinifera Cv. Petit Verdot red wine grapes.

            Petit Verdot grape skins by solid-phase extraction using a combination of reverse-phase and ion-exchanging materials. This procedure allowed us to separate a fraction of anthocyanin-free flavonol 3-O-glycosides that was further split into neutral and acidic subfractions, thus facilitating flavonol identification. By means of semipreparative reverse-phase high-performance liquid chromatography, we isolated several of these flavonol 3-O-glycosides for structural elucidation. The identification of different flavonol 3-O-glycosides was based on liquid chromatography-diode array detection-electrospray ionization-tandem mass spectrometry and NMR data when available. The results suggest that red grape flavonol 3-O-glycosides comprise three different complete series, according to the nature of the sugar moiety linked to the C-3 position. The 3-O-glucosides were the main derivative of the six possible flavonol aglycones (kaempferol, quercetin, isorhamnetin, myricetin, laricitrin, and syringetin), whereas the 3-O-galactoside derivatives were found as minor compounds for all of the flavonol aglycones. The 3-O-glucuronides are the third kind of red grape flavonol derivatives and normally account as minor compounds for all of the flavonol aglycones, with the exception of quercetin 3-O-glucuronide, which was as abundant as quercetin 3-O-glucoside. In addition, the presence of quercetin 3-O-(6"-rhamnosyl)-glucoside (rutin) was also detected as a trace compound in the skins of Petit Verdot grapes.
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              Concepts and technologies for tracking bioactive compounds in natural product extracts: generation of libraries, and hyphenation of analytical processes with bioassays.

              Since the advent of high-throughput screening (HTS) in the early 1990s, a wealth of innovative technologies have been proposed and implemented for the effective localization and characterization of bioactive constituents in complex matrices. The latest developments in this field are reviewed under the perspective of their applicability to natural product-based drug discovery. The approaches discussed here include TLC-based bioautography, HPLC-based assays with on-line, at-line and off-line detection, as well as affinity-based methods, such as frontal affinity chromatography, pulsed ultrafiltration mass spectrometry, imprinted polymers, and affinity capillary electrophoresis. Selected practical examples are given to illustrate the strengths and limitations of these approaches in contemporary natural product lead discovery. In addition, compatibility issues of natural product extracts and HTS are addressed, and selected protocols for the generation of high quality libraries are presented.
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                Author and article information

                Journal
                Sci Pharm
                Sci Pharm
                SciPharm
                Scientia Pharmaceutica
                The Austrian Journal of Pharmaceutical Sciences (Austria )
                0036-8709
                2218-0532
                2015
                11 December 2014
                : 83
                : 2
                : 353-367
                Affiliations
                [1 ]Division of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland
                [2 ]CIFLORPAN, College of Pharmacy, University of Panama, Apartado 0824-00172, Panama, Republic of Panama
                [3 ]BASF SE, Carl-Bosch-Strasse 38, D-67056 Ludwigshafen, Germany
                Author notes
                [* ]Corresponding author. E-mail: matthias.hamburger@ 123456unibas.ch (M. Hamburger)
                Article
                SciPharm-83-353
                10.3797/scipharm.1410-10
                4729439
                26839818
                ae65cea1-5acc-4023-902d-8c109871cdd5
                Copyright: © Guldbrandsen et al.

                This is an Open Access article distributed under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/3.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                : 17 October 2014
                : 11 December 2014
                Categories
                Research Article

                Pharmacology & Pharmaceutical medicine
                panamanian plant extracts,hplc-based activity profiling,fungicide,insecticide,herbicide

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