A flavanone and two phenolic acids from Chrysanthemum morifolium with phytotoxic and insect growth regulating activity.
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 13CNMR 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-trihydroxyflavanone7-O-glucuronide (eriodictyol7-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.).
Beninger
Clifford W
CW
Department of Environmental Biology, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
Abou-Zaid
Mamdouh M
MM
Kistner
Adrienne L
AL
Hallett
Rebecca H
RH
Iqbal
Muhammad J
MJ
Grodzinski
Bernard
B
Hall
J Christopher
JC
D000821:Animal Feed; D000818:Animals; D002247:Carbon Isotopes; D005591:Chemical Fractionation; D002726:Chlorogenic Acid / Q000494:pharmacology / Q000633:toxicity; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D031202:Chrysanthemum / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D044950:Flavanones / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D006868:Hydrolysis; D062385:Hydroxybenzoates / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D007313:Insecta / Q000187:drug effects / Q000254:growth & development*; D007814:Larva / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects / Q000254:growth & development; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry
D002247:Carbon Isotopes; D044950:Flavanones; D062385:Hydroxybenzoates; D010936:Plant Extracts; D002726:Chlorogenic Acid; C017616:phenolic acid; C028610:flavanone