Antialgal and antifungal activity of natural hydroxamic acids and related compounds

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 6, 1996, Pages 1569-1571

  Bravo, Héctor R ^a   Lazo, Waldo ^a  

^a UNIVERSITY OF CHILE   (Chile)

Author keywords

Antialgal antifungal activity; Candida albicans; Chlorella xanthella; Hydroxamic acids

Indexed keywords

ALGAE; CANDIDA ALBICANS; CHLORELLA XANTHELLA; FUNGI;

EID: 0000264241     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf950345e     Document Type: Article

References (23)

1. Atkinson, J.; Morand, P.; Arnason, J. T.; Niemeyer, H. M.; Bravo, H. R. Analogues of the cyclic hydroxamic acid 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: decomposition to benzoxazolinones and reaction with β-mercaptoethanol. J. Org. Chem. 1991, 56, 1788-1800.
2. Barnes, J. P.; Putnam, A. R. Role of benzoxazinones in allelopathy by rye (Secale cereale L.). J. Chem. Ecol. 1987, 13, 889-906.
3. Barnes, J. P.; Putnam, A. R.; Burke, B. A.; Aasen, A. J. Isolation and characterization of allelochemicals in rye herbage. Phytochemistry 1987, 26, 1385-1390.
4. Bravo, H. R.; Lazo, W. Antimicrobial activity of cereal hydroxamic acids and related compounds. Phytochemistry 1993, 33, 569-571.
5. Copaja, S. V.; Bravo, H. R.; Niemeyer, H. M. Quantitation of N-(2-hydroxy-4-methoxyphenyl)-glyoxylohydroxamic acid, a reactive intermediate in reactions of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. J. Org. Chem. 1982, 47, 3542-3545.
6. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley: New York, 1979.
7. Hashimoto, Y.; Ishizaki, T.; Shudo, K. T. A multi-centered electrophile formed from a unique bioactive cyclic hydroxamic acid, 4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one. Tetrahedron 1991, 47, 1837-1860.
8. Hofman, J.; Hofmanova, O. 1,4-Benzoxazine derivatives in plants. Sephadex fractionation and identification of a new glucoside. Eur. J. Biochem. 1969, 8, 109-112.
9. Hofman, J.; Hofmanova, O. 1,4-Benzoxazine derivatives in plants. Absence of 2,4-dihydroxy-7-methoxy-2H-1,4-benxozazin-3(4H)-one from uninjured Zea mays plants. Phytochemistry 1971, 10, 1441-1444.
10. Johnson, C. D. The Hammett Equation; Cambridge University Press: Cambridge, U.K., 1973; pp 1-67.
11. Leighton, V.; Niemeyer, H. M.; Jonsson, L. M. V. Substrate specificity of a glucosyl transferase and N-hydroxylase involved in the biosynthesis of cyclic hydroxamic acids in Gramineae. Phytochemistry 1994, 36, 887-892.
12. Lyons, P. C.; Hipskind, J. D.; Wood, K. V.; Nicholson, R. L. Separation and quantification of cyclic hydroxamic acids and related compounds by high-pressure liquid chromatography. J. Agric. Food Chem. 1988, 36, 57-60.
13. Matlin, S. A.; Sammes, P. G.; Upton, R. M. The oxidation of trimethylsilylated to hydroxamic acids, J. Chem, Soc., Perkin Trans. 1 1979, 2481-2487.
14. Niemeyer, H. M. Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the Gramineae. Phytochemistry 1988, 27, 3349-3358.
15. Niemeyer, H. M.; Corcuera, L. J.; Pérez, F. J. Reaction of a cyclic hydroxamic acid from Gramineae with thiols. Phytochemistry 1982, 21, 2287-2289.
16. Otsuka, H.; Hirai, Y.; Nagao, T.; Yamasaki, K. Anti-inflammatory activity of benzoxazinoids from roots of Coix Lachryma-Iovivar Ma-Yuen. J. Nat. Prod. 1988, 51, 74-79.
17. Férez, F. J.; Niemeyer, H. M. The reduction of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one by thiols. Phytochemistry 1985, 24, 2963-2966.
18. Férez, F. J.; Niemeyer, H. M. Reaction of DIMBOA with amines. Phytochemistry 1989, 28, 1831-1834.
19. Queirolo, C. B.; Andreo, C. S.; Niemeyer, H. M.; Corcuera, L. J. Inhibition of ATPase from chloroplasts by a hydroxamic acid from Gramineae. Phytochemistry 1983, 22, 2455-2458.
20. Quiroz, A.; Niemeyer. H. M. Reaction of 7-substituted 4-hydroxyl-1,4-benzoxazin-3-ones in strongly acid media. Heterocycles 1991, 32, 1681-1685.
21. Sumida, S.; Ueda, M. Chlorella as a model system to study herbicidal mode of action and its application to a new herbicide, O-Ethyl-O-(3-methyl-6-nitrophenyl)-N-sec-butyl phosphorothioamidate (S-2846). In Mechanism of Pesticide Action; G. K. Kohn, Ed.; ACS Symposium Series 2; Washington, DC, 1974; pp 156-167.
22. Viertanen, A. I.; Hietala, P. K. Precursors of benzoxazolinone in rye plants. Precursor II. The Aglucone. Acta Chem. Scand. 1960, 14, 499-502.
23. Weiss, L. B.; Bravo, H. R. Substituent effect in frontier orbitals of cyclic hydroxamic acids. Heterocycles 1994, 38, 9-16.