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United States Department of Agriculture

Agricultural Research Service

Research Project: CHEMISTRY OF NATURAL PRODUCTS FOR PEST MANAGEMENT AND CROP DEVELOPMENT

Location: Natural Products Utilization Research

Title: Bioassay-guided Isolation of Anti-Algal Constituents from Inula Helenium and Limonium Myrianthum

Authors
item Cantrell, Charles
item Mamonov, Leonid - INST. OF PLANT PHYS.
item Ryabushkina, Natalja - INST. OF PLANT PHYS.
item Kustova, Tatyana - INST. OF PLANT PHYS.
item Fischer, Nikolaus - UNIVERSITY OF MISSISSIPPI
item Schrader, Kevin

Submitted to: Archives for Organic Chemistry (ARKIVOC)
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: December 1, 2006
Publication Date: January 1, 2007
Citation: Cantrell, C.L., Mamonov, L.K., Ryabushkina, N., Kustova, T.S., Fischer, N.H., Schrader, K. 2007. Bioassay-guided Isolation of Anti-Algal Constituents from Inula Helenium and Limonium Myrianthum. Archives for Organic Chemistry (ARKIVOC). vii:65-75.

Interpretive Summary: Over 70 crude plant extracts, primarily from Kazakhstan, were screened against the freshwater phytoplanktons Oscillatoria perornata and Selenastrum capricornutum. Extracts from Limonium myrianthum and Inula helenium both demonstrated selective inhibition against the cyanobacterium O. perornata compared to activity against the beneficial green alga S. capricornutum. This odor-producing cyanobacterium, Oscillatoria perornata, has been attributed as the primary cause of off-flavor in pond-raised catfish in west Mississippi and elsewhere in the United States. Natural compounds were isolated from these active plant extracts and found to selectively inhibit the growth of O. perornata.

Technical Abstract: Over 70 crude plant extracts, primarily from Kazakhstan, were screened against the freshwater phytoplanktons Oscillatoria perornata and Selenastrum capricornutum. Extracts from Limonium myrianthum and Inula helenium both demonstrated selective inhibition against the odor-producing cyanobacterium O. perornata compared to activity against the green alga S. capricornutum. Bioassay-guided fractionation of the L. myrianthum dichloromethane extract resulted in the identification of nepodin, torachrysone, chrysophanol, and physcion. Nepodin demonstrated the desired selective inhibition with lowest-complete-inhibition concentration values of 100 ug/mL and >100 ug/mL towards O. perornata and S. capricornutum, respectively. Similarly, chrysophanol also demonstrated the desired selective inhibition with lowest-complete-inhibition concentration values of 10 ug/mL and >100 ug/mL, respectively. Bioassay-guided fractionation of the I. helenium hexane extract resulted in the isolation of alantolactone, isoalantolactone, and 11 aH,13-dihydroisoalantolactone. Activities of these three isolated constituents as well as those of synthetic isomers are reported.

Last Modified: 4/15/2014