Anti-Helicobacter pylori agents from the cashew apple

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 2, 1999, Pages 533-537

  Kubo, Jun ^a   Lee, Jae Ran ^a   Kubo, Isao ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

(E) 2 hexenal; Anacardic acids; Antibacterial activity; Helicobacter pylori; Urease inhibitory activity

Indexed keywords

2 HEXENAL; 2-HEXENAL; ALDEHYDE; AMOXICILLIN; ANACARDIC ACID; CLARITHROMYCIN; ENZYME INHIBITOR; METRONIDAZOLE; SALICYLIC ACID DERIVATIVE; TETRACYCLINE DERIVATIVE; UREASE;

ANGIOSPERM; ANTIBACTERIAL ACTIVITY; APPLE; ARTICLE; CHEMISTRY; DRUG EFFECT; ENZYME INHIBITION; ERADICATION THERAPY; GASTRITIS; HELICOBACTER PYLORI; INDUSTRIALIZATION; ISOLATION AND PURIFICATION; MICROBIOLOGICAL EXAMINATION; PEPTIC ULCER;

ALDEHYDES; ANACARDIC ACIDS; ENZYME INHIBITORS; HELICOBACTER PYLORI; MICROBIAL SENSITIVITY TESTS; ROSALES; SALICYLIC ACIDS; UREASE;

ANACARDIACEAE; ANACARDIUM OCCIDENTALE; BACTERIA (MICROORGANISMS); HELICOBACTER PYLORI; MAGNOLIOPHYTA; MALUS X DOMESTICA; NEGIBACTERIA;

EID: 0345040184     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9808980     Document Type: Article

References (36)

1. Bauer, K.; Garbe, D.; Surburg. Common Fragrance and Flavor Materials; VCH: Weinheim, 1990; p 13.
2. Bhattacharya, S. K.; Mukhopadhyay, M.; Mohan Rao, P. J. R.; Bagchi, A.; Ray, A. B. Pharmacological investigation on sodium salt and acetyl derivative of anacardic acid. Phytother. Res. 1987, 1, 127-134.
3. Blaser, M. J. H. pylori: microbiology of a 'slow' bacterial infection. Trends Microbiol. 1993, 1, 255-60.
4. Cesareo, S. D.; Langton, S. R. Kinetic properties of Helicobacter pylori urease compared with jack bean urease. FEMS Microbiol. Lett. 1992, 99, 15-22.
5. Coates, N. J.; Gilpin, M. L.; Gwynn, M. N.; Lewis, D. L.; Milner, P. H.; Spear, S. R.; Tyler, J. W. SB-202742, A novel lactamase inhibitor isolated from Spondias mombin. J. Nat. Prod. 1994, 57, 654-657.
6. Duckworth, H. W.; Coleman, J. E. Physicochemical and kinetic properties of mushroom tyrosinase. J. Biol. Chem. 1970, 245, 1613-1625.
7. Dunn, B. E.; Campbell, G. P.; Perez-Perez, G. I.; Blaser, M. J. Purification and characterization of urease from Helicobacter pylori. J. Biol. Chem. 1990, 265, 9464-9469.
8. Gellerman, J. L.; Wash, N. J.; Werner, N. K.; Schlenk, H. Antimicrobial effects of anacardic acids. Can. J. Microbiol. 1969, 15, 1219-1223.
9. Goodwin, C. S.; Armstrong, J. A.; Marshall, B. J. Campylobacter pyloridis, gastritis, and peptic ulceration. J. Clin. Pathol. 1986, 39, 353-365.
10. Gorin, G.; Chin, C. C. A new method of assay and specific enzymic activity. Anal. Biochem. 1966, 17, 49-59.
11. Grazzini, R.; Hesk, D.; Heiminger, E.; Hildenbrandt, G.; Reddy, C. C.; Cox-Foster, D.; Medford, J. Craig, R.; Mumma, R. O. Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids. Biochem. Biophys. Res. Commun. 1991, 176, 775-780.
12. Harris, A. W.; Misiewicz, J. J. Helicobacter pylori; Blackwell Healthcare Communications: London, 1996; pp 34-46.
13. Himejima, M.; Kubo, I. Antimicrobial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil. J. Agric. Food Chem. 1991, 39, 418-421.
14. Irie, J.; Murata, M.; Homma, S. Glycerol-3-phosphate dehydrogenase inhibitors, anacardic acids, from Gingko biloba. Biosci. Biotechnol. Biochem. 1996, 60 240-243.
15. Itokawa, H.; Totsuka, N.; Nakahara, K.; Maezuru, M.; Takeya, K.; Kondo, M.; Inamatsu, M.; Morita, H. A quantitative structure-activity relationship for antitumor activity of long-chain phenols from Gingko biloba L. Chem. Pharm. Bull. 1989, 37, 1619-1621.
16. Kubo, A.; Lunde, C. S.; Kubo, I. Antimicrobial activity of the olive oil flavor compounds. J. Agric. Food Chem. 1995, 43, 1629-1633.
17. Kubo, I.; Komatsu, S.; Ochi, M. Molluscicides from the cashew Anacardium occidentale and their large-scale isolation. J. Agric. Food Chem. 1986, 34, 970-973.
18. Kubo, I.; Kim, M.; Naya, K.; Komatsu, S.; Yamagiwa, Y.; Ohashi, K.; Sakamoto, Y.; Hirakawa, S.; Kamikawa, T. Prostaglandin synthetase inhibitors from an African medicinal plant Ozoroa mucronata. Chem. Lett. 1987, 1101-1104.
19. Kubo, I.; Ochi, M.; Vieira, P. C.; Komatsu, S. Antitumor agents from the cashew Anacardium occidentale apple juice. J. Agric. Food Chem. 1993a, 41, 1012-1015.
20. Kubo, I.; Muroi, H.; Himejima, M.; Yamagiwa, Y.; Mera, H.; Tokushima, K.; Ohta, S.; Kamikawa, T. Structure-antibacterial activity relationships of anacardic acids. J. Agric. Food Chem. 1993b, 41, 1016-1019.
21. Kubo, I.; Kinst-Hori, I.; Yokokawa, Y. Tyrosinase inhibitors from Anacardium occidentale fruits. J. Nat. Prod. 1994, 57, 545-552.
22. Kubo, I.; Muroi, H.; Kubo, A. Structural functions of antimicrobial long-chain alcohols and phenolics. Bioorg. Med. Chem. 1995, 3, 873-880.
23. Maciel, M. I.; Hansen, T. J.; Aldinger, S. B.; Laboes, J. N. Flavor chemistry of cashew apple juice. J. Agric. Food Chem. 1986, 34, 923-927.
24. Marshall, B. J.; Armstrong, J. A.; McGechie, D. B.; Glancy, R. J. Attempt to fulfill Koch's postulates for pyloric Campylobacter. Med. J. Aust. 1985, 142, 436-439.
25. Mégraud, F.; Neman-Simha, V.; Brügmann, D. Further evidence of the toxic effect of ammonia produced by Helicobacter pylori urease on human epithelial cells. Infect. Immun. 1992, 60, 1858-1863.
26. Muroi, H.; Kubo, I. Bactericidal activity of anacardic acid against Streptococcus mutans and their potentiation. J. Agric. Food Chem. 1993, 41, 1780-1783.
27. Muroi, H.; Kubo, I. Bactericidal activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus. J. Appl. Bacteriol. 1996, 80, 387-394.
28. Muroi, H.; Kubo, A.; Kubo, I. Antimicrobial activity of cashew apple flavor compounds. J. Agric. Food Chem. 1993, 41, 1106-1109.
29. Nagabhushana, K. S.; Shobha, S. V.; Ravindranath, B. Selective ionophoric properties of anacardic acid. J. Nat. Prod. 1995, 58, 807-810.
30. Shobha, S. V.; Ramadoss, C. S.; Ravindranath, Inhibition of soybean lipoxygenase-I by anacardic acids, cardols, and cardanols. J. Nat. Prod. 1994, 57, 1755-1757.
31. Spencer, G. F.; Tjarks, L. W.; Kleiman, R. Alkyl and phenyl-alkyl anacardic acids from Knema elegans seed oil. J. Nat. Prod. 1980, 43, 724-730.
32. Sullivan, J. T.; Richards, C. S.; Lloyd, H. A.; Krishna, G. Anacardic acid: Molluscicide in cashew nut shell liquid. Planta Med. 1982, 44, 175-177.
33. Toyomizu, M.; Sugiyama, S.; Jin, R. L.; Nakatsu, T. α-Glucosidase and aldose reductase inhibitors-constituents of cashew, Anacardium occidentale, nut shell liquids. Phytother. Res. 1993, 7, 252-254.
34. Tyman, J. H. P. Nonisoprenoid long chain phenols. Chem. Soc. Rev. 1979, 8, 499-537 and references cited therein.
35. Warren, J. R.; Marshall, B. J. Unidentified curved bacilli on gastric epithelium in active chronic gastritis. Lancet I 1983, 1273-1275.
36. Yamagiwa, Y.; Ohashi, K.; Sakamoto, Y.; Hirakawa, S.; Kamikawa, T.; Kubo, I. Syntheses of anacardic acids and ginkgoic acid. Tetrahedron 1987, 43, 3387-3394.