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United States Department of Agriculture

Agricultural Research Service

Research Project: DISCOVERY AND DEVELOPMENT OF NATURAL PRODUCTS FOR CONTROL OF PLANT DISEASES IN AGRICULTURE

Location: Natural Products Utilization Research

Title: Antifungal Activity of Thiophenes from Echinops Ritro

Authors
item Fokialakis, Nikolas - UNIV. OF ATHENS/USDA
item Cantrell, Charles
item Duke, Stephen
item Skaltsounis, Alexios - UNIV. OF ATHENS
item Wedge, David

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: December 20, 2005
Publication Date: February 8, 2006
Citation: Fokialakis, N., Cantrell, C.L., Duke, S.O., Skaltsounis, A.L., Wedge, D.E. 2006. Antifungal activity of thiophenes from echinops ritro. Journal of Agricultural and Food Chemistry. 54: 1651-1655.

Interpretive Summary: Extracts from thirty plants from Greece were evaluated for their antifungal activity using direct-bioautography assays with three Colletotrichum species that cause strawberry anthracnose. Root extracts from Echinops ritro possessed the most potent antifungal compounds found among the thirty plants studied. A class of phytochemicals called thiophenes were isolated and further studied for their biological activity. Three thiophenes were shown to be active at 30 uM against Colletotrichum acutatum, C. fragariae, C. gloeosporioides, Fusarium oxysporum, Phomopsis viticola, and P. obscurans.

Technical Abstract: Extracts from thirty plants of the Greek flora were evaluated for their antifungal activity using direct-bioautography assays with three Colletotrichum species. Among the bioactive extracts, the dichloromethane extract of the radix of Echinops ritro was the most potent. Bioassay-guided fractionation of this extract led to the isolation of eight thiophenes. Antifungal activities of isolated compounds together with a previously isolated thiophene from E. transiliensis were first evaluated by bioautography and subsequently evaluated in greater detail using a 96-well microtiter assay against Colletotrichum acutatum, C. fragariae, C. gloeosporioides, Botrytis cinerea, Fusarium oxysporum, Phomopsis viticola, and P. obscurans. 5'-(3-buten-1-ynyl)-2,2'-bithiophen (1), alpha-terthienyl (2) and 2-[pent-1,3-diynyl]-5[4-hydroxybut-1-ynyl]-thiophene (5) at 3 and 30 uM were active against all three Colletotrichum species, Fusarium oxysporum, Phomopsis viticola, and P. obscurans.

Last Modified: 8/22/2014