Isolation and identification of secondary metabolites of Clitocybe nuda responsible for inhibition of zoospore germination of Phytophthora capsici

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 30, 2012, Pages 7341-7344

  Chen, Jin Tong ^a   Su, Huey Jen ^b   Huang, Jenn Wen ^c  

^a FISHERIES RESEARCH INSTITUTE   (Taiwan)

^b MEIHO UNIVERSITY   (Taiwan)

^c NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

antifungal substance; Clitocybe nuda; indole 3 carbaldehyde; p benzoquinone; Phytophthora capsici; secondary metabolite

Indexed keywords

ANTI-FUNGAL; CLITOCYBE NUDA; INDOLE-3-CARBALDEHYDE; P-BENZOQUINONE; PHYTOPHTHORA CAPSICI; SECONDARY METABOLITES;

CHROMATOGRAPHY; ETHANOL; ION EXCHANGE; METABOLITES; SILICA GEL;

CULTIVATION;

2 METHOXY 5 METHYL 6 METHOXYMETHYL P BENZOQUINONE; 2-METHOXY-5-METHYL-6-METHOXYMETHYL-P-BENZOQUINONE; 3 INDOLECARBALDEHYDE; 6 HYDROXY 2H PYRAN 3 CARBALDEHYDE; 6-HYDROXY-2H-PYRAN-3-CARBALDEHYDE; ALDEHYDE; ANTIINFECTIVE AGENT; BENZOQUINONE DERIVATIVE; DEXTRAN; INDOLE DERIVATIVE; INDOLE-3-CARBALDEHYDE; PYRAN DERIVATIVE; SEPHADEX;

AGARICALES; ARTICLE; DRUG EFFECT; GERMINATION; ISOLATION AND PURIFICATION; METABOLISM; MICROBIOLOGY; PHYSIOLOGY; PHYTOPHTHORA; PLANT DISEASE;

AGARICALES; ALDEHYDES; ANTI-INFECTIVE AGENTS; BENZOQUINONES; DEXTRANS; GERMINATION; INDOLES; PHYTOPHTHORA; PLANT DISEASES; PYRANS;

CLITOCYBE; FUNGI; NUDA; PHYTOPHTHORA CAPSICI;

EID: 84864761592     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf301570y     Document Type: Article

References (39)

1. Alizadeh, A.; Tsao, P. H. Phytophthora capsici. In Phytophthora Diseases Worldwide; Erwin, D. C., Ribeiro, O. K., Eds.; American Phytopathological Society (APS) Press: St. Paul, MN, 1996; pp 262-268.
2. Hwang, B. K.; Kim, D. H. Phytophthora blight of pepper and its control in Korea Plant Dis. 1995, 79, 221-227
3. Muto, M.; Takahashi, H.; Ishihara, K.; Yuasa, H.; Huang, J. W. Antimicrobial activity of medicinal plant extracts used by indigenous people in Taiwan Plant Pathol. Bull. 2005, 14, 13-24
4. Anke, T. Basidiomycetes: A source for new bioactive secondary metabolites Prog. Ind. Microbiol. 1989, 27, 51-66
5. Arnone, A.; Nasini, G.; Vajna de Pava, O. Marasmane sesquiterpenes from the basidiomycete Clitocybe hydrogramma Phytochemistry 1997, 46, 1099-1101
6. Benedict, R. G.; Brady, L. R. Antimicrobial activity of mushroom metabolites J. Pharm. Sci. 1972, 61, 1820-1822
7. Hautzel, R.; Anke, H. Screening of basidiomycetes and ascomycetes for plant growth regulating substances. Introduction of the gibberellic acid induced de novo synthesis of hydrolytic enzymes in embryoless seeds of Triticum aestivum as a test system Z. Naturforsch. 1990, 45, 1093-1098
8. Korzybski, T.; Kowszyk, G. Z.; Kurylowicz, W. Antifungal antibiotics (polyenes). In Antibiotics: Origin, Nature and Properties; Korzybski, T., Ed.; Oxford: London, U.K., 1967; pp 769-820.
9. Anke, T. The antifungal strobilurins and their possible ecological role Can. J. Bot. 1995, 73, 940-945
10. Anke, T. Strobilurins. In Fungal Biotechnology; Anke, T., Ed.; Chapman and Hall: London, U.K., 1997; pp 206-212.
11. Suay, I.; Arenal, F.; Asensio, F. J.; Basilio, A.; Cabello, M. A.; Díez, M. T.; García, J. B.; Val, A. G.; Gorrochategui, J.; Hernández, P.; Peláez, F.; Vicente, M. F. Screening of basidiomycetes for antimicrobial activities Antonie van Leeuwenhoek 2000, 78, 129-139
12. Dulger, B.; Ergul, C. C.; Gucin, F. Antimicrobial activity of the macrofungus Lepista nuda Fitoterapia 2002, 73, 695-697
13. Mustafa, Y.; Bilgili, F. Antimicrobial activities of fruit bodies and/or mycelial cultures of some mushroom isolates Pharm. Biol. 2006, 44, 660-667
14. Sangita, D.; Agate, A. D. Antibacterial activity of some Indian mushrooms Int. J. Med. Mushrooms 2000, 2, 141-150
15. Chen, J. T.; Huang, J. W. Control of plant diseases with secondary metabolites of Clitocybe nuda New Biotechnol. 2009, 26, 193-198
16. Chen, J. T.; Peng, J. T.; Chen, M. H.; Chien, S. Y. Effects of indoor composting and conventional composting on the yield of Agaricus bisporus J. Taiwan Agric. Res. 2010, 59, 19-28
17. Ko, W. H.; Chase, L.; Kunimoto, R. A microsyringe method for determining concentration of fungal propagules Phytopathology 1973, 63, 1206-1207
18. Mehrotra, R.; Vishwakarma, R. A.; Thakur, R. S. Anietane diterpenoid from Coleus zeylanicus Phytochemistry 1989, 28, 3135-3137
19. 13C-NMR-spektroskopie chinoider verbindungen-I: Substituierte p -benzochinone und 2-cyclohexenone Tetrahedron 1976, 32, 1431-1436
20. Kiuchi, F.; Takashima, H.; Tsuda, Y. Dimerization of 2,5- dihydroxybezoquinones in water Chem. Pharm. Bull. 1998, 46, 1129-1234
21. Machado, G.; Carrera, P.; Pomini, A. M.; Marsaioli, A. J. Chemical defense in harvestmen (arachnida, opiliones): Do benzoquinone secretions deterinvertebrate and vertebrate predators J. Chem. Ecol. 2005, 31, 2519-2539
22. Lana, E. J. L.; Carazza, F.; Takahashi, J. Antibacterial evaluation of 1,4-benzoquinone derivatives J. Agric. Food Chem. 2006, 54, 2053-2056
23. Kwon, H. C.; Choi, S. U.; Lee, K. R. Phytochemical constituents of Artemisia stolonifera Arch. Pharm. Res. 2001, 24, 312-315
24. Muhammad, I.; Takamatsu, S.; Walker, L. A.; Mossa, J. S.; Fong, H. H. S.; El-Feraly, F. S. Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata Phytother. Res. 2003, 17, 887-891
25. Dowd, P.; Zheng, Z. B. On the mechanism of the anticlotting action of vitamin E quinine Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8171-8175
26. Gonzalez-Ibarra, M.; Farfán, N.; Trejo, C.; Uribe, S.; Lotina-Hennsen, B. Selective herbicide activity of 2,5-di(benzylamine)- p -benzoquinone against the monocot weed Echinochloa crusgalli. An in vivo analysis of photosynthesis and growth J. Agric. Food Chem. 2005, 53, 3415-3420
27. Abraham, I.; Joshi, R.; Pardasani, P.; Pardasani, R. T. Recent advances in 1,4-benzoquinone chemistry J. Braz. Chem. Soc. 2011, 22, 385-421
28. Schulte, K. E.; Rücker, G.; El-Kersch, M. Nicotin and 3-formoyl-4-hydroxy-2 H -pyranaus Herpestis moniera Phytochemistry 1972, 11, 2649-2651
29. Abdel-Halim, O. B.; Marzouk, A. M.; Mothana, R.; Awadh, N. A new tyrosinase inhibitor from Crinum yemense as potential treatment for hyperpigmentation Pharmazie 2008, 63, 405-408
30. Su, H. J.; Lin, M. J.; Tsou, Y. J.; Ko, W. H. Pseudallin, a new antibiotic produced by the human pathogenic fungus Pseudallescheria boydii, with ecological significance Bot. Stud. 2012, 53, 239-242
31. Bernart, M.; Gerwick, H. W. 3-(Hydroxyacetyl)indole, a plant growth regulator from the Oregon red alga Prionitis lanceolata Phytochemistry 1990, 29, 3697-3698
32. Wu, P. L.; Hsu, Y. L.; Jao, C. W. Indole alkaloids from Cephalanceropsis gracilis J. Nat. Prod. 2006, 69, 1467-1470
33. Shimizu, K.; Geng, X.; Hashiguchi, M.; Suhara, H.; Fukunaga, S.; Yasutake, S.; Kondo, R.; Tsutsui, M.; Sato, I. Indole-3-carbaldehyde: A tyrosinase inhibitor from fungus YL185 J. Wood Sci. 2003, 49, 349-354
34. Yue, Q.; Miller, C. J.; White, J. F.; Richardson, M. D. Isolation and characterization of fungal inhibitors from Epichloe festucae J. Agric. Food Chem. 2000, 48, 4687-4692
35. Turner, W. B. Fungal Metabolites; Academic Press: London, U.K., 1983; Vol. 1, p 446.
36. Muszyńska, B.; Sułkowska-Ziaja, K.; Ekiert, H. Indole compounds in fruiting bodies of some edible Basidiomycota species Food Chem. 2011, 125, 1306-1308
37. Muszyńska, B.; Sułkowska-Ziaja, K. Analysis of indole compounds in edible Basidiomycota species after thermal processing Food Chem. 2012, 132, 455-459
38. Morgan, Y. R.; Turner, P.; Kennedy, B. J.; Hambley, T. W.; Lay, P. A.; Biffin, J. R.; Regtop, H. L.; Warwick, B. Preparation and characterization of dinuclear copper-indomethacin anti-inflammatory drugs Inorg. Chim. Acta 2001, 324, 150-161
39. Gutierrez-Lugo, M. T.; Woldemichael, G. M.; Singh, M. P.; Suarez, P. A.; Maiese, W. M.; Montenegro, B. N. Isolation of three new naturally occurring compounds from the culture of Micromonospora sp. P1068 Nat. Prod. Res. 2005, 19, 645-652