Algicidal and antifungal compounds from the roots of Ruta graveolens and synthesis of their analogs |
| |
Authors: | Meepagala Kumudini M Schrader Kevin K Wedge David E Duke Stephen O |
| |
Institution: | USDA-ARS, Natural Products Utilization Research Unit, P.O. Box 8048, University, MS 38677, USA. kmeepaga@olemiss.edu |
| |
Abstract: | Bioassay-guided fractionation of the ethyl acetate extract of Ruta graveolens roots yielded rutacridone epoxide with potent selective algicidal activity towards the 2-methyl-isoborneol (MIB)-producing blue-green alga Oscillatoria perornata, with relatively little effect on the green alga Selenastrum capricornutum. The diol-analog of rutacridone epoxide, gravacridondiol, which was also present in the same extract, had significantly less activity towards O. perornata. Rutacridone epoxide also showed significantly higher activity than commercial fungicides captan and benomyl in our micro-bioassay against the agriculturally important pathogenic fungi Colletotrichum fragariae, C. gloeosporioides, C. acutatum, and Botrytis cineara and Fusarium oxysporium. Rutacridone epoxide is reported as a direct-acting mutagen, precluding its use as an agrochemical. In order to understand the structure-activity relationships and to develop new potential biocides without toxicity and mutagenicity, some analogs containing the (2-methyloxiranyl)-dihydrobenzofuran moiety with an epoxide were synthesized and tested. None of the synthetic analogs showed comparable activities to rutacridone epoxide. The absolute stereochemistry of rutacridone was determined to be 2'(R) and that of rutacridone epoxide to be 2'(R), 3'(R) by CD and NMR analysis. |
| |
Keywords: | Ruta graveolens Rutaceae Oscillatoria perornata Selenastrum capricornutum Algicide Fungicide Acridone alkaloids Colletotrichum fragariae C gloeosporioides C acutatum Botrytis cinearea Fusarium oxysporium |
本文献已被 ScienceDirect PubMed 等数据库收录! |
|