Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 20, 2005, Pages 7741-7748

  Cantrell, C L ^a   Schrader, K K ^a   Mamonov, L K ^b   Sitpaeva, G T ^c   Kustova, T S ^b   Dunbar, C ^d   Wedge, D E ^a  

^a NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

^b Institute of Plant Physiology Genetics and Bioengineering   (Kazakhstan)

^c Geology and Natural Resources of the Republic of Kazakhstan   (Kazakhstan)

^d UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Botrytis cinerea; Colletotrichum acutatum; Colletotrichum fragariae; Colletotrichum gloeosporioides; Fusarium oxysporum; Haplophyllum sieversil; Oscillatoria agardhil; Oscillatoria perornata; Phomopsis obscurans; Pseudanabaena; Selenastrum capricornutum

Indexed keywords

ALKALOID; EUDESMIN; FUNGICIDE; FURAN DERIVATIVE; LIGNAN; PLANT EXTRACT;

ALGA; ARTICLE; CHEMISTRY; COLLETOTRICHUM; DRUG EFFECT; ISOLATION AND PURIFICATION; RUTACEAE;

ALGAE; ALKALOIDS; COLLETOTRICHUM; FUNGICIDES, INDUSTRIAL; FURANS; LIGNANS; PLANT EXTRACTS; RUTACEAE;

BOTRYOTINIA FUCKELIANA; CHLOROPHYTA; COLLETOTRICHUM; COLLETOTRICHUM FRAGARIAE; FUSARIUM OXYSPORUM; GLOMERELLA ACUTATA; GLOMERELLA CINGULATA; HAPLOPHYLLUM; OSCILLATORIA; OSCILLATORIA PERORNATA; PHOMOPSIS OBSCURANS; PLANKTOTHRIX AGARDHII; PSEUDANABAENA; PSEUDANABAENA SP.; SELENASTRUM CAPRICORNUTUM;

EID: 27144462057     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051478v     Document Type: Article

References (33)

1. Duke, S. O.; Baerson, S. R.; Dayan, F. E.; Rimando, A. M.; Scheffler, B. E.; Tellez, M. R.; Wedge, D. E.; Schrader, K. K.; Akey, D. H.; Arthur, F. H.; De Lucca, A. J.; Gibson, D. M.; Harrison, H. F., Jr.; Peterson, J. K.; Gealy, D. R.; Tworkoski, T.; Wilson, C. L.; Morris, J. B. United States Department of Agriculture-Agricultural Research Service research on natural products for pest management. Pest Manage. Sci. 2003, 59, 708-717.
2. Tucker, C. S. Off-flavor problems in aquaculture. Rev. Fish. Sci. 2000, 8, 45-88.
3. Martin, J. F.; Izaguirre, G.; Waterstrat, P. A planktonic Oscillatoria species from Mississippi catfish ponds that produces the off-flavor compound 2-methylisoborneol. Water Res. 1991, 25, 1447-1451.
4. van der Ploeg, M.; Tucker, C. S.; Boyd, C. E. Geosmin and 2-methylisoborneol production by cyanobacteria in fish ponds in the southeastern United States. Water Sci. Technol. 1992, 25, 283-290.
5. Schrader, K. K.; Dennis, M. E. Cyanobacteria and earthy/musty compounds found in commercial catfish (Ictalurus punctatus) ponds in the Mississippi Delta and Mississippi-Alabama Blackland Prairie. Water Res. 2005, 39, 2807-2814.
6. Filippini, R.; Piovan, A.; Innocenti, G.; Caniato, R.; Cappelletti, E. M. Production of coumarin compounds by Haplophyllum patavinum in vivo and in vitro. Phytochemistry 1998, 49, 2337-2340.
7. Gunes, H. S. (-)-Haplonolide, a novel terpenoid from Haplophyllum vulcanicum (Rutaceae). J. Fac. Pharm. Gazi Uni. 2001, 18, 35-41.
8. Ivanova, A.; Mikhova, B.; Stambolijska, T.; Kostova, I. Lignan and coumarin glycosides from Haplophyllum suaveolens. Z. Naturforsch., C: J. Biosci. 2001, 56, 329-333.
9. Innocenti, G.; Puricelli, L.; Piacente, S.; Caniato, R.; Filippini, R.; Cappelletti, E. M. Patavine, a new arylnaphthalene lignan glycoside from shoot cultures of Haplophyllum patavinum. Chem. Pharm. Bull. 2002, 50, 844-846.
10. Prieto, J. M.; Giner, R. M.; Recio, M. C.; Schinella, G.; Manez, S.; Rios, J. L. Diphyllin acetylapioside, a 5-lipoxygenase inhibitor from Haplophyllum hispanicum. Plant. Med. 2002, 68, 359-360.
11. Puricelli, L.; Innocenti, G.; Piacente, S.; Caniato, R.; Filippini, R.; Cappelletti, E. M. Production of lignans by Haplophyllum patavinum in vivo and in vitro. Heterocycles 2002, 56, 607-612.
12. Al-Rehaily, A. J.; Al-Howiriny, T. A.; Ahmad, M. S.; Al-Yahya, M. A.; El-Feraly, F. S.; Hufford, C. D.; McPhail, A. T. Alkaloids from Haplophyllum tuberculatum. Phytochemistry 2001, 57, 597-602.
13. Khalifa, A. A.; Youssef, D. T. Lignans and an alkaloid from Haplophyllum tuberculatum. Bull. Pharm. Sci. 1999, 22, 157-166.
14. Ulubelen, A.; Mericli, A. H.; Kaya, U. An alkaloid and lignans from Haplophyllum telephioides. Phytochemistry 1994, 35, 1600-1601.
15. Ulubelen, A.; Mericli, A. H.; Mericli, F.; Sonmez, U.; Ilarslan, R. Alkaloids and coumarins from Haplophyllum thesioides. Nat. Prod. Lett. 1993, 1, 269-272.
16. Ahmad, S. Flindersine from Fagara heitzii. J. Nat. Prod. 1984, 47, 391-392.
17. Campbell, W. E.; Davidowitz, B.; Jackson, G. E. Quinolinone alkaloids from an Agathosma species. Phytochemistry 1990, 29, 1303-1306.
18. Al-Rehaily, A. J.; Ahmad, M. S.; Muhammad, I.; Al-Thukair, A. A.; Perzanowski, H. P. Furoquinoline alkaloids from Teclea nobilis. Phytochemistry 2003, 64, 1405-1411.
19. Roy, S. C.; Rana, K. K.; Guin, C. Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol monomethyl ether and furofuran lignans (±)-sesamin, (±)-eudesmin, (±)-piperitol methyl ether, (±)-pinoresinol, (±)-piperitol, and (±)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source. J. Org. Chem. 2002, 67, 3242-3248.
20. Espinel-Ingroff, 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.
21. Wedge, D. E.; Kuhajek, J. M. A microbioassay for fungicide discovery. SAAS Bull. Biochem. Biotechnol. 1998, 11, 1-7.
22. Homans, A. L.; Fuchs, A. Direct bioautography on thin-layer chromatograms as a method for detecting fungitoxic substances. J. Chromatogr. 1970, 51, 327-329.
23. Wedge, D. E.; Nagle, 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.
24. Tellez, M. R.; Dayan, F. E.; Schrader, K. K.; Wedge, D. E.; Duke, S. O. Composition and some biological activities of the essential oil of Callicarpa americana (L.). J. Agric. Food Chem. 2000, 48, 3008-3012.
25. Wedge, D. E.; Galindo, J. C. G.; Macias, F. A. Fungicidal activity of natural and synthetic sesquiterpene lactone analogs. Phytochemistry 2000, 53, 747-757.
26. van der Ploeg, M.; Dennis, M. E.; and de Regt, M. Q. Biology of Oscillatoria cf. chalybea, a 2-methylisoborneol producing blue-green alga of Mississippi catfish ponds. Water Sci. Technol. 1995, 31, 173-180.
27. Schrader, K. K.; de Regt, M. Q.; Tucker, C. S.; Duke, S. O. A rapid bioassay for selective algicides. Weed Technol. 1997, 11, 767-774.
28. Schrader, K. K.; de Regt, M. Q.; Tidwell, P. D.; Tucker, C. S.; Duke, S. O. Compounds with selective toxicity towards the off-flavor metabolite-producing cyanobacterium Oscillatoria cf. chalybea. Aquaculture 1998, 163, 85-99.
29. Latip, J.; Hartley, T. G.; Waterman, P. G. Lignans and coumarins metabolites from Melicope hayesii. Phytochemistry 1999, 51, 107-110.
30. Wedge, D. E.; Curry, K. J.; Boudreaux, J. E.; Pace, P. F.; Smith, B. J. A microtiter assay demonstrates sensitivity and resistance profiles for Botrytis cinerea isolates from Louisiana strawberry farms. Adv. Strawberry Res. 2001, 20, 27-33.
31. Schrader, K. K.; Tucker, C. S.; de Regt, M. Q.; Kingsbury, S. K. Evaluation of limnocorrals for studying the effects of phytotoxic compounds on plankton and water chemistry in aquaculture ponds. J. World Aquacult. Soc. 2000, 31, 403-415.
32. Schrader, K. K.; Nanayakkara, N. P. D.; Tucker, C. S.; Rimando, A. M.; Ganzera, M.; Schaneberg, B. T. Novel derivatives of 9,-10-anthraquinone are selective algicides against the musty-odor cyanobacterium Oscillatoria perornata. Appl. Environ. Microbiol. 2003, 69, 5319-5327.
33. Schrader, K. K.; Duke, S. O.; Kingsbury, S. K.; Tucker, C. S.; Duke, M. V.; Dionigi, C. P.; Millie, D. F.; Zimba, P. V. Evaluation of ferulic acid for controlling the musty-odor cyanobacterium, Oscillatoria perornata, in aquaculture ponds. J. Appl. Aquacult. 2000, 10, 1-16.