In vitro antifungal activity of the diterpenoid 7α-hydroxy-8(17)- labden-15-oic acid and its derivatives against botrytis cinerea

Molecules

Volumn 14, Issue 6, 2009, Pages 1966-1979

  Mendoza, Leonora ^a   Espinoza, Pamela ^a   Urzua, Alejandro ^a   Vivanco, Marcela ^a   Cotoras, Milena ^a  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

Author keywords

Acetylsalvic acid; Antifungal compounds; Botrytis cinerea; Diterpenoids; Eupatorium salvia; Salvic acid

Indexed keywords

ANTIFUNGAL AGENT; DITERPENE;

ARTICLE; BOTRYTIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; EUPATORIUM; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF; TOMATO;

ANTIFUNGAL AGENTS; BOTRYTIS; DITERPENES; EUPATORIUM; LYCOPERSICON ESCULENTUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANT LEAVES;

EID: 67649865802     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14061966     Document Type: Article

References (23)

1. Elad, Y.; Evensen, K. Physiologcal aspects of resistance to Botrytis cinerea. Phytopathology 1995, 85, 637-643.
2. Latorre, B.A.; Flores, V.; Sara, A.M.; Roco, A. Dicarboximide-resistant strains of Botrytis cinerea from table grapes in Chile: survey and characterization. Plant. Dis. 1994, 78, 990-994.
3. Grayer, R.J.; Kokubun, T. Plant-fungal interactions: the search for phytoalexins and other antifungal compounds from higher plants. Phytochemistry 2001, 56, 253-263.
4. Salah, M.A.; Bedir, E.; Toyang, N.J.; Khan, I.A.; Harries, M.D.; Wedge, D.E. Antifungal clerodane diterpenes from Macaranga monandra (L) Muell. Et Arg (Euphorbiaceae). J. Agric. Food Chem. 2003, 51, 7607-7610.
5. Scher, J.M.; Speakman, J.B.; Zapp, J.; Becker H. Bioactivity guided isolation of antifungal compounds from the liverwort Bazzania trilobata (L.) S.F. Gray. Phytochemistry 2004, 65, 2583-2588.
6. Cotoras, M.; Mendoza, L; Folch, C. Characterizacion of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3?-hidroxy-kaurenoic Acid. J. Agric. Food Chem. 2004, 52, 2821-2826.
7. Bouchra, C.; Achouri, M.; Hassani, L.M.I.; Hmamouchi, M. Chemical composition and antifungal activity of essential oils of seven Moroccan Labiatae against Botrytis cinerea Pers: Fr. J. Ethnopharmacol. 2003, 89, 165-169.
8. Haraguchi, H.; Kuwata, Y.; Inada, K.; Shingu, K.; Miyahara, K.; Nagao, M.; Yagi, A. Antifungal activity from Alpinia galanga and the competition for incorporation of unsaturated fatty acids in cell growth. Planta Med. 1996, 62, 308-313.
9. Haraguchi, H.; Oike, S.; Muroi, H.; Kubo, I. Mode of antibacterial action of totarol, a diterpene from Podocarpus nagi. Planta Med. 1996, 62, 122-125.
10. Tapia, L; Torres, J.; Mendoza, L.; Urzúa, A.; Ferreira, J.; Pavani, M.; Wilkens, M. Effect of 13-epi-Sclareol on the Bacterial Respiratory Chain. Planta Med. 2004, 70, 1058-1063.
11. Urzúa, A.; Caroli, M.; Vasquez, L.; Mendoza, L.; Wilkens, M.; Tojo, E. Antimicrobial study of the resinous exudate and of diterpenoids isolated from Eupatorium salvia (Asteraceae). J. Ethnopharmacol. 1998, 2, 251-254.
12. Hoeneisen, M.; Sammes, P.; Silva, M.; Watson, W. A new diterpenic acid and other constituents from Eupatorium salvia. Rev. Latinoamer Quim. 1979, 10, 37-40.
13. Calabuig, M.T.; Cortés, M.; Francisco, C.G.; Hernández, R.; Suárez, E. Labdane diterpenes from Cistus symphytifolius. Phytochemistry 1981, 20, 2255-2258
14. Arnoldi, A.; Merlini, L. Lipophilicity-antifungal activity relationships for some isoflavonoid phytoalexins. J .Agric. Food Chem. 1990, 38, 834-838.
15. Yang, G.; Jiang, X.; Yang, H. Development of novel pesticides based on phytoalexins: Part 2. Quantitative structure-activity relationships of 2-heteroaryl-4-chromanone derivatives. Pest Manag. Sci. 2002, 58, 1063-1067.
16. Zou, X.J.; Jin, G.Y.; Zhang, Z.X. Synthesis, fungicidal activity, and QSAR of pyridazinonethiadiazoles. J. Agric. Food Chem. 2002, 50, 1451-1454.
17. Voda, K.; Boh B.; Vrtacnik M. A quantitative structure-antifungal activity relationship study of oxygenated aromatic essential oil compounds using data structuring and PLS regression analysis. J. Mol. Model. 2004, 10, 76-84.
18. Niewiadomy, A.; Matysiak, J.; Fekner, Z.; Czeczco, R. Synthesis, antifungal activity and SAR of N-substituted and N, N-disubstituted 2,4-dihydroxythiobenzamides. J. Pestic. Sci. 2006, 31, 14-22.
19. Lunde, C.S.; Kubo, I. Effect of Polygodial on the Mitochondrial ATPase of Saccharomyces cerevisiae. Antimicrob. Agents Chemother. 2000, 44, 1943-1953.
20. Tamura, H.; Mizutani, A.; Yukioka, H.; Miki, N.; Ohba, H.; Masuko, M. Effect of the methoxyiminoacetamide fungicide, SSF129, on respiratory activity in Botrytis cinerea. Pestic. Sci, 1999, 55, 681-686.
21. Munμoz, G.; Hinrichsen, P.; Brygoo Y.; Giraud, T. Genetic characterisation of Botrytis cinerea populations in Chile. Mycol. Res. 2002, 106, 594-601.
22. Mendoza, L.; Araya-Maturana, R.; Cardona, W.; Delgado-Castro, T.; García, C., Lagos C.; Cotoras, M. In vitro sensitivity of Botrytis cinerea to anthraquinone and anthrahydroquinone derivates. J. Agric. Food Chem. 2005, 53, 10080-10084.
23. Thevissen, K.; Terras, F.R.G.; Broekaert, W.F. Permeabilization of fungal membranes by plant defensins inhibit fungal growth. Appl. Environ. Microbiol. 1999, 65, 5451-5458.