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A Flavanone and Two Phenolic Acids from Chrysanthemum morifolium with Phytotoxic and Insect Growth Regulating Activity

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Abstract

Leaves of Chrysanthemum morifolium cv. Ramat were extracted sequentially with hexane, ethyl acetate, and methanol. The methanol fraction, when incorporated into artificial diet was found to reduce the growth of cabbage looper (Trichoplusia ni Hubner) larvae at concentrations between 500 and 5000 ppm of diet. Fractionation of the methanol extract on a Sephadex column yielded five fractions, three of which reduced the weight of larvae relative to the control. One fraction was analyzed using high performance liquid chromatography (HPLC) and found to contain three main constituents. These compounds were purified using a combination of gel permeation chromatography on Sephadex LH20 and HPLC, and analyzed by 1H and 13C NMR as well as undergoing chemical and physical analyses. The compounds were identified as: 1, chlorogenic acid (5-O-caffeoylquinic acid); 2, 3,5-O-dicaffeoylquinic acid; and 3, 3′, 4′, 5-trihydroxyflavanone 7-O-glucuronide (eriodictyol 7-O-glucuronide). At concentrations between 100 to 1000 ppm these compounds reduced both growth and photosynthesis of Lemna gibba L. with the order of efficacy being: flavanone > chlorogenic acid > 3,5-O-dicaffeoylquinic acid. Furthermore, when incorporated separately into artificial diet these compounds, at 10 to 1000 ppm, enhanced or reduced growth of the cabbage looper (Trichoplusia ni) and gypsy moth (Lymantria dispar L.).

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Authors and Affiliations

  1. Department of Environmental Biology, University of Guelph, Guelph, Ontario, Canada, N1G 2W1

    Clifford W. Beninger, Adrienne L. E. Kistner, Rebecca H. Hallett & J. Christopher Hall

  2. Natural Resources Canada, Great Lakes Forestry Centre, 1219 Queen St. E., Sault Ste.Marie, Ontario, Canada, P6A 2E5

    Mamdouh M. Abou-Zaid

  3. Department of Plant Agriculture, University of Guelph, Guelph, Ontario, Canada, N1G 2W1

    Muhammad J. Iqbal & Bernard Grodzinski

Authors
  1. Clifford W. Beninger
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  2. Mamdouh M. Abou-Zaid
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  3. Adrienne L. E. Kistner
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  4. Rebecca H. Hallett
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  5. Muhammad J. Iqbal
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  6. Bernard Grodzinski
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  7. J. Christopher Hall
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Correspondence to J. Christopher Hall.

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Beninger, C.W., Abou-Zaid, M.M., Kistner, A.L.E. et al. A Flavanone and Two Phenolic Acids from Chrysanthemum morifolium with Phytotoxic and Insect Growth Regulating Activity. J Chem Ecol 30, 589–606 (2004). https://doi.org/10.1023/B:JOEC.0000018631.67394.e5

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  • DOI: https://doi.org/10.1023/B:JOEC.0000018631.67394.e5

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