flavanone and two phenolic acids from Chrysanthemum morifolium with phytotoxic and insect growth regulating activity

• Published in: Journal of chemical ecology Vol. 30; no. 3; pp. 589 - 606
• Main Authors: Beninger, C.W, Abou-Zaid, M.M, Kistner, A.L.E, Hallett, R.H, Iqbal, M.J, Grodzinski, B, Hall, C
• Format: Journal Article
• Language: English
• Published: New York, NY Springer 01.03.2004; Springer Nature B.V
• Subjects: Acids; Animal and plant ecology; Animal Feed; Animal, plant and microbial ecology; Animals; Autoecology; Biological and medical sciences; Carbon Isotopes; Chemical Fractionation; Chlorogenic Acid - pharmacology; Chlorogenic Acid - toxicity; Chromatography, Gel; Chromatography, High Pressure Liquid; Chrysanthemum - chemistry; Chrysanthemum morifolium; Diet; Dose-Response Relationship, Drug; flavanones; Flavanones - chemistry; Flavanones - isolation & purification; Flavanones - toxicity; Fractionation; Fundamental and applied biological sciences. Psychology; General aspects; growth and development; Hydrolysis; Hydroxybenzoates - chemistry; Hydroxybenzoates - isolation & purification; Hydroxybenzoates - toxicity; insect growth regulators; Insecta - drug effects; Insecta - growth & development; Insects; Larva - metabolism; Larvae; Lemna gibba; Liquid chromatography; Lymantria dispar; Lymantriidae; Magnetic Resonance Spectroscopy; Mass Spectrometry; Methanol; Molecular Structure; Moths - drug effects; Moths - growth & development; Noctuidae; phenolic compounds; Phenology; Phenols; Photosynthesis; phototoxins; Physical growth; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Leaves - chemistry; plant-insect relations; Toxicity; Trichoplusia ni; Monocotyledones; Lymantriidae; Lemnaceae; Trichoplusia ni; Phenolic acid; Growth; Chemical compound; Insecta; Compositae; Dendranthema grandiflora; Lemna gibba; Phytotoxicity; Arthropoda; Dicotyledones; Angiospermae; Lepidoptera; Phenols; Spermatophyta; Noctuidae; Invertebrata; Lymantria dispar
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1023/B:JOEC.0000018631.67394.e5

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.).