Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 4, 2003, Pages 890-896

  Oliva, Anna ^a,c   Meepagala, Kumudini M ^b   Wedge, David E ^b   Harries, Dewayne ^b   Hale, Amber L ^b   Aliotta, Giovanni ^a   Duke, Stephen O ^b  

^a SECOND UNIVERSITY OF NAPLES   (Italy)

^b NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

^c STONY BROOK UNIVERSITY   (United States)

Author keywords

Botrytis cinerea; C. fragariae; C. gloeosporioides; Colletotrichum acutatum; Fungicide; Furanocoumarin; Fusarium oxysporum; P. obscurans; Phomopsis viticola; Psoralen; Quinoline alkaloid; Quinolone alkaloid; Rue; Ruta graveolens

Indexed keywords

1 METHYL 2 (6' (3' ',4' ' METHYLENEDIOXYPHENYL)HEXYL) 4 QUINOLONE; 1-METHYL-2-(6'-(3' ',4' '-METHYLENEDIOXYPHENYL)HEXYL)-4-QUINOLONE; ALKALOID; FUNGICIDE; PSORALEN DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE;

ANALYTIC METHOD; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BIOASSAY; BOTRYTIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; COLLETOTRICHUM; DRUG EFFECT; DRUG ISOLATION; EXTRACTION; FUSARIUM; ISOLATION AND PURIFICATION; PLANT LEAF; PROTON NUCLEAR MAGNETIC RESONANCE; RUTA; SPECIES DIFFERENTIATION;

ALKALOIDS; BOTRYTIS; COLLETOTRICHUM; FUNGICIDES, INDUSTRIAL; FUSARIUM; PLANT LEAVES; PSORALENS; QUINOLINES; QUINOLONES; RUTA;

BOTRYOTINIA FUCKELIANA; BOTRYTIS; COLLETOTRICHUM; COLLETOTRICHUM FRAGARIAE; FUSARIUM; FUSARIUM OXYSPORUM; GLOMERELLA ACUTATA; PHOMOPSIS; PHOMOPSIS VITICOLA; RUTA; RUTA GRAVEOLENS; RUTACEAE;

EID: 0037433127     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0259361     Document Type: Article

References (25)

1. Kirst, H. A.; Michel, K. H.; Mynderase, J. S.; Chio, E. H.; Yao, R. C.; Nakasukasa, W. M.; Boeck, L. D.; Occlowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Thompson, G. D. Discovery, isolation and structure elucidation of a family of the structurally unique, fermentation derived tetracyclic macrolides. ACS Symp. Ser. 1992, No. 505, 214-225.
2. McChesney, J. D. Biological and chemical diversity and the search for new pharmaceuticals and other bioactive natural products. In Human Medicinal Agents from Plants; Kinghorn, A. D., Balandrin, M. F., Eds; ACS Symposium Series 534; American Chemical Society: Washington, DC, 1993; p 38-47.
3. Farr, D. F.; Bills, G. F.; Chamuris, G. P.; Rossman, A. Y. Fungi on Plant and Plant Products in the United States; American Phytopathological Society: St. Paul, MN, 1989; 1252 pp.
4. Maas, J. L. In Compendium of Strawberry Diseases; American Phytopathological Society: St. Paul, MN, 1998; pp 1-98.
5. Ali-Shtayeh, M. S.; Abu Ghdeib, S. I. Antifungal activity of plant extracts against dermatophytes. Mycoses 1999, 42, 665-672.
6. Trovato, A.; Monforte, M. T.; Forestieri, A. M.; Pizzimenti, F. In vitro anti-mycotic activity of some medicinal plants containing flavonoids. Boll. Chim. Farm. 2000, 139, 225-227.
7. Wolters, B.; Eilert, U. Antimicrobial substances in callus cutures of Ruta graveolens. Planta Med. 1981, 43, 166-174.
8. Aliotta, G.; Caiero, G.; De Feo, V.; Di Blasio, B.; Iacovino, R.; Oliva, A. Allelochemicals from rue (Ruta graveolens L.) and olive (Olea europaea L.) oil mill waste waters as potential natural pesticides. Curr. Top. Phytochem. 2000, 3, 167-177.
9. Ojala, T.; Remes, S.; Haansuu, P.; Vuorela, H.; Hiltunen, R., Haahtela, K.; Vuorela, P. Antimicrobial activity of some courmain containing herbal plants growing in Finland. J. Ethnopharmacol. 2000, 73, 299-305.
10. Oliva, A.; Lahoz, E., Contillo; R., Aliotta, G. Fungistatic activity of Ruta graveolens L. extract and its allelochemicals. J. Chem. Ecol. 1999, 25, 519-526.
11. Annunzioata, R.; Cenini, S.; Palmisano, G.; Tollari, S. 4(1H)-Quinoline alkaloids. An efficient synthesis of graveoline by palladium-catalysed reductive N-heterocyclisation. Synth. Comm. 1996, 26, 495-501.
12. Kostova, I.; Ivanova, A.; Mikhova, B.; Klaiber, I. Alkaloids and coumarins from Ruta graveolens. Monatsh. Chem. 1999, 130, 703-707.
13. Pussset, J.; Lopez, J. L.; Pais, M.; Al Neirabeyeh, M.; Veillon, J. M. Plants of New Caledonia. Part 132. Isolation and 2D NMR studies of alkaloids from Comptonella sessilifoliola. Planta Med. 1991, 57, 153-155.
14. Espinel-Ingrof, A.; Kerkering, T. M. Spectrophotometric method of inoculum preparation for the in vitro susceptibility testing of filamentous fungi. J. Clin. Microbiol. 1991, 29, 393-394.
15. Wedge, D. E.; Kuhajek, J. M. A microbioassay for fungicide discovery. SAAS Bull. Biochem. Biotechnol. 1998, 11, 1-7.
16. Wedge, D. E.; Nagel, D. G. A new 2D-TLC bioautography method for the discovery of novel antifungal agents to control plant pathogens. J. Nat. Prod. 2000, 63, 1050-1054.
17. Wedge, D. E.; Galindo, J. C. G.; Marcias, F. A. Fungicidal activity of natural and synthetic sesquiterpene lactone analogs. Phytochemistry 2000, 53, 747-757.
18. Novak, I.; Buzas, G.; Minker, E.; Koltai, M.; Szendrei, K. Active constituents of Ruta graveolens. Pharmazie 1965, 20, 738.
19. Reisch, J.; Novak, I.; Szendrei, K.; Minker, E. Chemistry of natural substances. XV. 2-[4-(3,4-Methylenedioxyphenyl)butyl]-4-quinolone, an alkaloid from Ruta graveolens. Naturwissenschaften 1967, 54, 517.
20. Sayed, K. E.; Al-Said, M. S.; El-Feraly, F. S.; Ross, S. A. New quinoline alkaloids from Ruta chalepensis. J. Nat Prod. 2000, 63, 995-997.
21. Somanathan, R.; Smith, K. M. Synthesis of some 2-alkyl-4-quinolone and 2-alkyl-4-methoxyquinoline alkaloids. J. Heterocycl. Chem. 1981, 18, 1077-1079.
22. Stebbing, A. R. Hormesis-the stimulation of growth by low levels of inhibitors. Sci. Total Environ. 1982, 22, 213-234.
23. Calabrese, E. J.; Baldwin, L. A. Reevaluation of the fundamental dose-response relationship. BioScience 1999, 49, 725-732.
24. Calabrese, E. J.; Baldwin, L. A. Chemical hormesis: Its historical foundations as a biological hypothesis. Toxicol. Pathol. 1999, 27, 195.
25. Stebbing, A. R. Hormesis: Interpreting the beta-curve using control theory. J. Appl. Toxicol. 2000, 20, 93-101.