- Algicidal and antifungal compounds from the roots of Ruta graveolens and synthesis of their analogs
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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.
- Meepagala, Kumudini M.,Schrader, Kevin K.,Wedge, David E.,Duke, Stephen O.
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- Synthesis of novel inhibitors of electron transport
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Molecular modelling comparisons of several known natural and synthetic inhibitors of electron transport, e.g. rotenone, papaverine, and piericidin A, suggested new 'hybrid' structure 8-12, and relatives as potential new inhibitors.Synthetic routes to these targets, some of which display significant biological activity, are outlined.
- Cockerill, G. Stuart,Levett, Philip C.,Whiting, Donald A.
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p. 1103 - 1114
(2007/10/02)
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