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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #100935
Title: STRUCTURE-ACTIVITY RELATIONSHIPS OF QUASSINOIDS ON PLANTS

Author
item Dayan, Franck
item Watson, Susan
item GALINDO, J - UNIV OF CADIZ,SPAIN
item HERNANDEZ, A - UNIVERSITY OF BASC COUNTY
item DOU, J - UNIVERSITY OF MISSISSIPPI
item MCCHESNEY, J - UNIVERSITY OF MISSISSIPPI
item Duke, Stephen

Submitted to: Pesticide Biochemistry and Physiology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/1/1999
Publication Date: N/A
Citation: N/A

Interpretive Summary: Quassinoids are natural products isolated from several plant species. These compounds are important because they can potentially be used as herbicides. There is little information about the structural features that make these molecules active. We discovered that a particular part of the molecule called an oxymethylene bridge is required to make these molecules act like herbicides. We used computer modeling to understand the reasons for this requirement.

Technical Abstract: Quassinoids are naturally occurring compounds isolated from several plant species of the Simaroubaceae family that have phytotoxic and allelopathic activities. There is relatively little information about the structural characteristics imparting biological activity to these diterpene lactones or their effects on plants. We studied the effects of the oxymethylene ring on the biological activity and molecular conformation of several quassinoids. The presence of this functionalization had a great effect on the 3-dimensional conformation and biological activity of these natural products. In the absence of the oxymethylene ring, the quassinoids were more planar and had little phytotoxic effect. In addition, this bridging function introduced a new reactive center that caused the terpene backbone to bend. Molecules with such conformation were highly phytotoxic, causing reduced root growth of lettuce (Lactuca sativa) and affecting all stages of mitosis in onion (Allium cepa) root tips.