Natural Products as Sources of New Fungicides (I): Synthesis and Antifungal Activity of Acetophenone Derivatives Against Phytopathogenic Fungi

Chemical Biology and Drug Design

Volumn 81, Issue 4, 2013, Pages 545-552

  Ma, Ya Tuan ^a   Fan, Hua Fang ^a   Gao, Yu Qi ^a   Li, He ^a   Zhang, An Ling ^a   Gao, Jin Ming ^a  

^a NORTHWEST A F UNIVERSITY   (China)

Author keywords

2,4 dihydroxy 5 methylacetophenone; Acetophenone derivatives; Antifungal activity; Natural products; Structure activity relationship

Indexed keywords

ACETOPHENONE DERIVATIVE; BENZYL DERIVATIVE; FUNGICIDE; HYMEXAZOL; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ALTERNARIA; ALTERNARIA SOLANI; ANTIFUNGAL ACTIVITY; ARTICLE; BOTRYTIS CINEREA; CARBON NUCLEAR MAGNETIC RESONANCE; COLLETOTRICHUM; COLLETOTRICHUM GLOEOSPORIODES; CONTROLLED STUDY; FUNGAL VIRULENCE; FUSARIUM OXYSPORUM; GROWTH RATE; IC 50; IN VITRO STUDY; MYCELIAL GROWTH; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS;

ACETOPHENONES; ANTIFUNGAL AGENTS; BIOLOGICAL AGENTS; FUNGI; MICROBIAL SENSITIVITY TESTS; OXAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

FUNGI;

EID: 84875429220     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12064     Document Type: Article

References (19)

1. Cohen M.L. (2000) Changing patterns of infectious disease. Nature;406:762-767.
2. Janisiewicz W.J., Korsten L. (2002) Biological control of postharvest diseases of fruits. Annu Rev Phytopathol;40:411-441.
3. Mueller A.A., Reiter S.A., Heider K.G., Wagner H. (1999) Plant-derived acetophenones with antiasthmatic and anti-inflammatory properties: inhibitory effects on chemotaxis, right angle light scatter and actin polymerization of polymorphonuclear granulocytes. Planta Med;65:590-594.
4. VanEtten H.D., Sandrock R.W., Wasmann C.C., Soby S.D., McCluskey K., Wang P. (1995) Detoxification of phytoanticipins and phytoalexins by phytopathogenic fungi. Can J Bot;73:518-525.
5. Lv J., Qian Y., Liu T., Wang Y. (2007) Synthesis and evaluation of amphiphilic cationic quinine-derived for antibacterial activity against methicillin-resistant Staphylococcus aureus. Bioorg Med Chem Lett;17:4102-4106.
6. Konstantinova L.S., Bol'shakov O.I., Obruchnikova N.V., Laborie H., Tanga A., Sopéna V., Lanneluc I., Picot L., Sablé S., Thiéry V., Rakitin O.A. (2009) One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1, 2, 3-dithiazoles and evaluation of their antimicrobial and antitumor activity. Bioorg Med Chem Lett;19:136-141.
7. Gul H.I., Vepsalainen J., Gul M., Erciyas E., Hanninen O. (2000) Cytotoxic activities of mono and bis Mannich bases derived from acetophenone against Renca and Jurkat cells. Pharm Acta Helv;74:393-398.
8. Sivakumar P.M., Sheshayan G., Doble M. (2008) Experimental and QSAR of acetophenones as antibacterial agents. Chem Biol Drug Des;72:303-313.
9. Zheng C.D., Li G., Li H.Q., Xu X.J., Gao J.M., Zhang A.L. (2008) DPPH-scavenging activities and structure-activity relationships of phenolic compounds. Nat Prod Commun;5:1759-1765.
10. Simonsen H.T., Adsersen A., Bremner P., Heinrich M., Wagner Smitt U., Jaroszewski J.W. (2004) Antifungal constituents of Melicope borbonica. Phytother Res;18:542-545.
11. Tomás-Barberán F., Iniesta-Sanmartín E., Tomás-Lorente F., Rumbero A. (1990) Antimicrobial phenolic compounds from three Spanish Helichrysum species. Phytochemistry;29:1093-1095.
12. Brucker R.M., Baylor C.M., Walters R.L., Lauer A., Harris R.N., Minbiole K.P.C. (2008) The identification of 2, 4-diacetylphloroglucinol as an antifungal metabolite produced by cutaneous bacteria of the salamander Plethodon cinereus. J Chem Ecol;34:39-43.
13. Ligon J.M., Hill D.S., Hammer P.E., Torkewitz N.R., Hofmann D., Kempf H.J., van Pee K.H. (2000) Natural products with antifungal activity from Pseudomonas biocontrol bacteria. Pest Manag Sci;56:688-695.
14. Gao J.-M., Li Y., Xie S.-D., Zhang A.-L., Shi X.-W., Zhang W.-L. (2009) Isolation of antifungal agent 2, 4-dihydroxy-5-methylacetophenone from Polyporus picipes cultures, China Patent Application Code, 200910020963.7.
15. Dai H.-L., Liu W.-Q., Xu H., Yang L.-M., Lv M., Zhang Y.-T. (2009) Anti human immunodeficiency virus-1 (HIV-1) agents 1. Discovery of benzyl phenyl ethers as new HIV-1 inhibitors in vitro. Chem Pharm Bull;57:84-86.
16. Li X.-J., Zhang Q., Zhang A.-L., Gao J.-M. (2012) Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities. J Agric Food Chem;60:3424-3431.
17. Ma Y.T., Wang J.J., Liu X.W., Yang S.X., Gao J.M. (2010) 1-[4-(3-chloropropoxy)-2-hydroxyphenyl]ethanone. Acta Cryst;66:o52.
18. Ma Y.T., Zhang A.L., Yuan M.S., Gao J.M. (2010) 1-[4-(3, 5-difluorobenzyloxy)-2-hydroxyphenyl]ethanone. Acta Cryst;66:o2468.
19. Ma Y.T., Yang C.L., Li Z.S., Li Z.Q., Ding J.N. (2010) 1-(4-benzyloxy-2-hydroxyphenyl)ethanone. Acta Cryst;67:o3225.