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

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 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.).

Identification of the phenolic components of chrysanthemum flower (Chrysanthemum morifolium Ramat)

“…These compounds have been previously identified in chrysanthemum flower (Beninger et al, 2004;Clifford et al, 2007;Kim & Lee, 2005) and arnica flower (Lin & Harnly, 2008c), both plants in same Family of Compositae.…”

“…This flower is also widely used as a food supplement, or herb tea, and is considered a health food by many consumers (Chu, Fu, Guan, & Ye, 2004;Lai, Lim, Su, Shen, & Ong, 2007). The chrysanthemum flower contains significant amounts of flavonoids and hydroxycinnamoylquinic acids that are considered to be the biologically active components (Beninger et al, 2004;Chen, Li, Lu, Jiang, & Zeng, 2007;Clifford, Wu, Kirkpatrick, & Kuhnert, 2007;Guo, Wang, Cheng, Wen, Wang & Liang, 2008;Harborne & Baxter, 1999;Jiang, Xia, Xu, & Zheng, 2004;Kim & Lee, 2005;Lai et al, 2007;Li & Jiang, 2006;Miyazawa & Hisama, 2003;Wang, Yang, & Guo, 2008). Among them, acacetin 7-O-galactoside and apigenin 7-O-beta-D-(4"-caffeoyl) glucuronide were isolated as the anti-HIV compounds of this herb (Hu, Chen, Shi, Kilkuskie, Cheng, & Lee, 1994;Lee, Kim, & Lee, 2003).…”

Identification of Chlorogenic Acid as a Resistance Factor for Thrips in Chrysanthemum

“…This leads to a reduced bioavailability of amino acids and a decreased digestibility of dietary proteins (Felton et al, 1989(Felton et al, , 1991. This negative effect on herbivores has primarily been shown for caterpillars in vitro (Bernays et al, 2000;Beninger et al, 2004) and in vivo (Elliger et al, 1981;Huang and Renwick, 1995;Mallikarjuna et al, 2004). In addition a harmful effect of chlorogenic acid has been shown for different leaf beetles (Fulcher et al, 1998;Ikonen, et al, 2002;Jassbi, 2003) as well as for a leafhopper (Dowd and Vega, 1996) and for aphids (Miles and Oertli, 1993).…”

Simultaneous enhanced removal of Cu, PCBs, and PBDEs by corn from e-waste-contaminated soil using the biodegradable chelant EDDS

“…A number of studies have shown that in chelate-buffered nutrient solutions and chemically enhanced phytoremediation of heavy metals from contaminated soil, the uptake of metals by plants is strongly dependent on the concentration of the metal-chelate complex and the breakdown of the root exclusion mechanisms (Beninger et al 2004;Hattori et al 2006;Luo et al 2006b). In the present study, the application of 1 mM kg −1 EDDS enhanced the accumulation of Cu in root with a 0.071 translocation factor (TF, C shoot /C root ), while a higher efficiency of phytoextraction was achieved in the 3 mM EDDS (TF=0.10) and 5 mM EDDS (TF=0.12) treatments compared to the control (TF=0.03).…”