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Junya Mizutani - One of the best experts on this subject based on the ideXlab platform.
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termite Antifeedant Activity in aframomum melegueta
Phytochemistry, 1995Co-Authors: Pierre Escoubas, Labunmi Lajide, Junya MizutaniAbstract:Abstract n-Hexane and methanolic seed extracts of Aframomum melegueta were studied for termite Antifeedant Activity against workers of Reticulitermes speratus. Strong Antifeedant Activity was observed when the termite workers were tested in a choice filter paper disk bioassay containing 1% crude extracts. Bioassay-directed fractionation led to the isolation of gingerdione, 5-oxo-1-(4-hydroxy-3-methoxyphenyl)decan-3-one, [6]-paradol, 1-(4-hydroxy-3-methoxyphenyl)decan-3-one, [6]-gingerol, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one and [6]-shogaol, 1-(4-hydroxy-3-methoxyphenyl)dec-5-en-3-one, as the Antifeedant compounds. [6]-Gingerol and [6]-shogaol exhibited the strongest Antifeedant Activity at 1000 ppm, corresponding to 8 μg cm−2.
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Termite Antifeedant Activity in Xylopia aethiopica
Phytochemistry, 1995Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:Abstract A hexane extract of Xylopia aethiopica fruits and an aqueous methanol extract of the seeds were studied for termite Antifeedant Activity against workers of the subterranean termite, Reticulitermes speratus . The crude extract, at 1%, exhibited strong Antifeedant Activity in a choice filter paper disk bioassay. Bioassay-directed fractionation led to the isolation and identification of six ent-kaurane diterpenes in the hexane extract. Feeding deterrent Activity varied significantly with the structures when the compounds were tested at concentrations ranging from 5000 ppm (40 μg cm −2 ) to 100 ppm (0.824 μg cm −2 ). (−)-Kaur-16-en-19-oic acid had the strongest termite Antifeedants Activity among the ent-kauranes isolated. Two phenolic amides and four lignanamides were also isolated from the aqueous methanolic extract of seeds. E -3-(4-hydroxy-3-methoxyphenyl)- N -2-[4-Hydroxyphenylethyl]2-Propenamide was more active than E -3-(3,4-dihydroxyphenyl)- N -2-[4-Hydroxyphenylethyl]2-propenamide, whilst grossamide and the new lignanamide, demethylgrossamide, as well as (−)-cannabisins B and D exhibited potent feeding deterrent Activity at 5000 ppm. The identity of these compounds was established by spectroscopic analysis and synthesis. Two synthetic amides, E -3-(3,4-methylenedioxyphenyl)- N -2-[4-Hydroxyphenylethyl] propenamide and E -3-(3,4-methylenedioxyphenyl)- N -2-[octadecyl]-2-propenamide were also tested for Antifeedant Activity.
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Termite Antifeedant Activity in Detarium microcarpum
Phytochemistry, 1995Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:A methanol extract of Detarium microcarpum leaves exhibited strong feeding deterrent Activity against workers of the subterranean termite, Reticulitermes speratus in a paper disk choice bioassay. Bioassay directed fractionation led to the isolation of four clerodane diterpenes, 3,13E-clerodien-15-oic acid, 4(18), 13E-clerodien-15-oic acid, 18-oxo-3,13E-clerodien-15-oic acid and 2-oxo-3,13E-clerodien-15-oic acid as the active compounds. With the exception of the latter, this is the first report of these compounds from D. microcarpum. The four compounds possessed strong Antifeedant Activity at 1% and their structures were confirmed by spectroscopic methods.
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Antifeedant Activity of metabolites of Aristolochia albida against the tobacco cutworm, Spodoptera litura
Journal of Agricultural and Food Chemistry, 1993Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:The Antifeedant Activity of the metabolites of Aristolochia albida root extracts was examined against tobacco cutworm larvae (Spodoptera litura, Noctuidae) using a leaf-disk choice bioassay. The Antifeedant activities of the crude methanolic extract and aristolochic acid were very strong. 6-Hydroxyaristolochic acid showed moderate Activity, while aristolic acid, aristolactam, and aristolone did not demonstrate any Antifeedant Activity at a 0.1% concentration. Methyl aristolochiate and methyl 6-hydroxyaristolochiate prepared by diazomethane treatment of the acids showed significantly lower activities when compared with the parent acids (.)
Labunmi Lajide - One of the best experts on this subject based on the ideXlab platform.
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termite Antifeedant Activity in aframomum melegueta
Phytochemistry, 1995Co-Authors: Pierre Escoubas, Labunmi Lajide, Junya MizutaniAbstract:Abstract n-Hexane and methanolic seed extracts of Aframomum melegueta were studied for termite Antifeedant Activity against workers of Reticulitermes speratus. Strong Antifeedant Activity was observed when the termite workers were tested in a choice filter paper disk bioassay containing 1% crude extracts. Bioassay-directed fractionation led to the isolation of gingerdione, 5-oxo-1-(4-hydroxy-3-methoxyphenyl)decan-3-one, [6]-paradol, 1-(4-hydroxy-3-methoxyphenyl)decan-3-one, [6]-gingerol, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one and [6]-shogaol, 1-(4-hydroxy-3-methoxyphenyl)dec-5-en-3-one, as the Antifeedant compounds. [6]-Gingerol and [6]-shogaol exhibited the strongest Antifeedant Activity at 1000 ppm, corresponding to 8 μg cm−2.
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Termite Antifeedant Activity in Xylopia aethiopica
Phytochemistry, 1995Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:Abstract A hexane extract of Xylopia aethiopica fruits and an aqueous methanol extract of the seeds were studied for termite Antifeedant Activity against workers of the subterranean termite, Reticulitermes speratus . The crude extract, at 1%, exhibited strong Antifeedant Activity in a choice filter paper disk bioassay. Bioassay-directed fractionation led to the isolation and identification of six ent-kaurane diterpenes in the hexane extract. Feeding deterrent Activity varied significantly with the structures when the compounds were tested at concentrations ranging from 5000 ppm (40 μg cm −2 ) to 100 ppm (0.824 μg cm −2 ). (−)-Kaur-16-en-19-oic acid had the strongest termite Antifeedants Activity among the ent-kauranes isolated. Two phenolic amides and four lignanamides were also isolated from the aqueous methanolic extract of seeds. E -3-(4-hydroxy-3-methoxyphenyl)- N -2-[4-Hydroxyphenylethyl]2-Propenamide was more active than E -3-(3,4-dihydroxyphenyl)- N -2-[4-Hydroxyphenylethyl]2-propenamide, whilst grossamide and the new lignanamide, demethylgrossamide, as well as (−)-cannabisins B and D exhibited potent feeding deterrent Activity at 5000 ppm. The identity of these compounds was established by spectroscopic analysis and synthesis. Two synthetic amides, E -3-(3,4-methylenedioxyphenyl)- N -2-[4-Hydroxyphenylethyl] propenamide and E -3-(3,4-methylenedioxyphenyl)- N -2-[octadecyl]-2-propenamide were also tested for Antifeedant Activity.
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Termite Antifeedant Activity in Detarium microcarpum
Phytochemistry, 1995Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:A methanol extract of Detarium microcarpum leaves exhibited strong feeding deterrent Activity against workers of the subterranean termite, Reticulitermes speratus in a paper disk choice bioassay. Bioassay directed fractionation led to the isolation of four clerodane diterpenes, 3,13E-clerodien-15-oic acid, 4(18), 13E-clerodien-15-oic acid, 18-oxo-3,13E-clerodien-15-oic acid and 2-oxo-3,13E-clerodien-15-oic acid as the active compounds. With the exception of the latter, this is the first report of these compounds from D. microcarpum. The four compounds possessed strong Antifeedant Activity at 1% and their structures were confirmed by spectroscopic methods.
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Antifeedant Activity of metabolites of Aristolochia albida against the tobacco cutworm, Spodoptera litura
Journal of Agricultural and Food Chemistry, 1993Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:The Antifeedant Activity of the metabolites of Aristolochia albida root extracts was examined against tobacco cutworm larvae (Spodoptera litura, Noctuidae) using a leaf-disk choice bioassay. The Antifeedant activities of the crude methanolic extract and aristolochic acid were very strong. 6-Hydroxyaristolochic acid showed moderate Activity, while aristolic acid, aristolactam, and aristolone did not demonstrate any Antifeedant Activity at a 0.1% concentration. Methyl aristolochiate and methyl 6-hydroxyaristolochiate prepared by diazomethane treatment of the acids showed significantly lower activities when compared with the parent acids (.)
Pierre Escoubas - One of the best experts on this subject based on the ideXlab platform.
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termite Antifeedant Activity in aframomum melegueta
Phytochemistry, 1995Co-Authors: Pierre Escoubas, Labunmi Lajide, Junya MizutaniAbstract:Abstract n-Hexane and methanolic seed extracts of Aframomum melegueta were studied for termite Antifeedant Activity against workers of Reticulitermes speratus. Strong Antifeedant Activity was observed when the termite workers were tested in a choice filter paper disk bioassay containing 1% crude extracts. Bioassay-directed fractionation led to the isolation of gingerdione, 5-oxo-1-(4-hydroxy-3-methoxyphenyl)decan-3-one, [6]-paradol, 1-(4-hydroxy-3-methoxyphenyl)decan-3-one, [6]-gingerol, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one and [6]-shogaol, 1-(4-hydroxy-3-methoxyphenyl)dec-5-en-3-one, as the Antifeedant compounds. [6]-Gingerol and [6]-shogaol exhibited the strongest Antifeedant Activity at 1000 ppm, corresponding to 8 μg cm−2.
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Termite Antifeedant Activity in Xylopia aethiopica
Phytochemistry, 1995Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:Abstract A hexane extract of Xylopia aethiopica fruits and an aqueous methanol extract of the seeds were studied for termite Antifeedant Activity against workers of the subterranean termite, Reticulitermes speratus . The crude extract, at 1%, exhibited strong Antifeedant Activity in a choice filter paper disk bioassay. Bioassay-directed fractionation led to the isolation and identification of six ent-kaurane diterpenes in the hexane extract. Feeding deterrent Activity varied significantly with the structures when the compounds were tested at concentrations ranging from 5000 ppm (40 μg cm −2 ) to 100 ppm (0.824 μg cm −2 ). (−)-Kaur-16-en-19-oic acid had the strongest termite Antifeedants Activity among the ent-kauranes isolated. Two phenolic amides and four lignanamides were also isolated from the aqueous methanolic extract of seeds. E -3-(4-hydroxy-3-methoxyphenyl)- N -2-[4-Hydroxyphenylethyl]2-Propenamide was more active than E -3-(3,4-dihydroxyphenyl)- N -2-[4-Hydroxyphenylethyl]2-propenamide, whilst grossamide and the new lignanamide, demethylgrossamide, as well as (−)-cannabisins B and D exhibited potent feeding deterrent Activity at 5000 ppm. The identity of these compounds was established by spectroscopic analysis and synthesis. Two synthetic amides, E -3-(3,4-methylenedioxyphenyl)- N -2-[4-Hydroxyphenylethyl] propenamide and E -3-(3,4-methylenedioxyphenyl)- N -2-[octadecyl]-2-propenamide were also tested for Antifeedant Activity.
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Termite Antifeedant Activity in Detarium microcarpum
Phytochemistry, 1995Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:A methanol extract of Detarium microcarpum leaves exhibited strong feeding deterrent Activity against workers of the subterranean termite, Reticulitermes speratus in a paper disk choice bioassay. Bioassay directed fractionation led to the isolation of four clerodane diterpenes, 3,13E-clerodien-15-oic acid, 4(18), 13E-clerodien-15-oic acid, 18-oxo-3,13E-clerodien-15-oic acid and 2-oxo-3,13E-clerodien-15-oic acid as the active compounds. With the exception of the latter, this is the first report of these compounds from D. microcarpum. The four compounds possessed strong Antifeedant Activity at 1% and their structures were confirmed by spectroscopic methods.
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Antifeedant Activity of metabolites of Aristolochia albida against the tobacco cutworm, Spodoptera litura
Journal of Agricultural and Food Chemistry, 1993Co-Authors: Labunmi Lajide, Pierre Escoubas, Junya MizutaniAbstract:The Antifeedant Activity of the metabolites of Aristolochia albida root extracts was examined against tobacco cutworm larvae (Spodoptera litura, Noctuidae) using a leaf-disk choice bioassay. The Antifeedant activities of the crude methanolic extract and aristolochic acid were very strong. 6-Hydroxyaristolochic acid showed moderate Activity, while aristolic acid, aristolactam, and aristolone did not demonstrate any Antifeedant Activity at a 0.1% concentration. Methyl aristolochiate and methyl 6-hydroxyaristolochiate prepared by diazomethane treatment of the acids showed significantly lower activities when compared with the parent acids (.)
Koichiro Komai - One of the best experts on this subject based on the ideXlab platform.
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synthesis and insect Antifeedant Activity of aurones against spodoptera litura larvae
Journal of Agricultural and Food Chemistry, 2007Co-Authors: Masanori Morimoto, Hiromi Fukumoto, Toki Nozoe, And Ai Hagiwara, Koichiro KomaiAbstract:A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect Antifeedant Activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 μmol/cm2. The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect Antifeedant Activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect Antifeedant Activity, but 4,5,6- and 3‘,4‘,5‘-trisubstituted compounds did not show this Activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect Antifeedant Activity against S. litura. Although the melting points did not correlate well with the insect Antifeedant Activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological Activity (pED50) and a hydrogen-bondi...
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Insect Antifeedant Activity of flavones and chromones against Spodoptera litura.
Journal of agricultural and food chemistry, 2003Co-Authors: Masanori Morimoto, Kumiko Tanimoto, Sachiko Nakano, Takayoshi Ozaki, And Ayako Nakano, Koichiro KomaiAbstract:The Antifeedant polymethylated flavones 5-hydroxy-3,6,7,8,4'-heptamethoxyflavone, 5-hydroxy-3,6,7,8-tetramethoxyflavone, and 5,6-dihydroxy-3,7-dimethoxyflavone have been isolated from the cudweed, Gnaphalium affine D. Don (Compositae). These flavonoids and authentic analogues showed insect Antifeedant Activity against the common cutworm (Spodoptera litura F.). In a previous paper, it was suggested that there was no substituent on the B-ring of the flavonoid for the beneficial Antifeedant Activity against the common cutworm. These flavonoids having a phenyl group as the B-ring and the chromone as elimination of the B-ring from the flavonoids were used to test the hypothesis of the previously described B-ring effect. The known fact is that Sculletaria baicarensis (Rutaceae) produced the 2-phenyl flavone. Test compounds and their methylated derivatives were prepared from this material for the structure-Activity relationship (SAR) study of insect Antifeedant Activity. In spite of the 2-phenyl flavonoids, some tested compounds did not show any insect Antifeedant Activity against the common cutworm, although these inactive flavonoids were deficient in the 6-substituent group on the A-ring of the flavonoid. This 6-position-substituted derivative almost showed strong insect Antifeedant Activity against common cutworm. Moreover, the tested flavonoids having a hydroxyl group as a substituent on any of the positions tended to increase the Activity. These results suggested the importance of the 6-position substitution on the flavonoid; however, hydrophilic substituents decreased the Activity. Baicalein (5,6,7-trihydroxyflavone) derivatives did not show any Activity despite having the 6-substituent derivative. Although the Activity of some chromones increased the Activity of the flavone, the bulky B-ring was a disadvantage for the Antifeedant Activity. It was suggested that the charge on C(3) and C(5) of the flavonoid was important for the biological Activity. Additionally, an adequate hydrogen bonding property, which is different from lipophilicity, was an advantage for the Activity on the basis of a QSAR analysis.
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Antifeedant Activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F.
Phytochemistry, 2002Co-Authors: Masanori Morimoto, Kumiko Tanimoto, Akiko Sakatani, Koichiro KomaiAbstract:Abstract The insect Antifeedant anthraquinone aldehyde nordamnacanthal (1,3-dihydroxy-anthraquinone-2-al) was identified in Galium aparine L., and isolated from the root powder of akane (Rubia akane), a member of the Rubiaceae. Structure–Activity relationship (SAR) studies using a series of anthraquinone analogues suggested that the aldehyde group on the anthraquinone was more important than the quinone moiety for Antifeedant Activity against the common cutworm (Spodoptera litura). High levels of nordamnacanthal were found in the seed leaf stage and in callus tissue induced from seedlings of G. aparine, but its concentration decreased with plant development. Since these compounds are natural pigments for dying textiles, we also evaluated the Antifeedant Activity against the carpet beetle (Attagenus japonicus ), a textile pest was also evaluated. While nordamnacanthal had strong Antifeedant Activity against the common cutworm, it did not show any Antifeedant Activity against the carpet beetle. The most effective Antifeedant against the carpet beetle was the major constituent in the extract of R. trictorum, lucidin-3-O-primeveroside, a food pigment.
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Structure-Activity Relationship for the Insect Antifeedant Activity of Benzofuran Derivatives
Bioscience biotechnology and biochemistry, 1999Co-Authors: Masanori Morimoto, Masamitsu Urakawa, Tatsuo Fujitaka, Koichiro KomaiAbstract:Coumaran (2,3-dihydrobenzofuran), a secondary metabolite of Cyperus nipponicus, inhibits the feeding of polyphagous insects. This secondary metabolite is regarded as one of the defensive systems of the Cyperaceae. A number of naturally occurring benzofurans that differ in their substitution pattern and oxidation state have been investigated for their ability to inhibit insect feeding by a bioassay with the common cutworm (Spodoptera litura F. Noctuidae) that applies the leaf disk method. The evaluation of the Antifeedant Activity of each test compound used the ED50 value based on the dose-response curve that was calculated with the probit method. The 2,3-dihydrobenzofuran derivative, 7-acetyl-4,6-dimethoxy-2-isopropenyl-2,3-dihydrobenzofuran, had an ED50 value of 1.3 μg (5.4×10-9 mol)/cm2 against the common cutworm. The introduction of methoxy and acetyl groups increased the insect Antifeedant Activity. Furthermore, the insect Antifeedant Activity increased with decreasing lipophilicity of the test compounds.
Masanori Morimoto - One of the best experts on this subject based on the ideXlab platform.
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Piperine analogs in a hydrophobic fraction from Piper ribersoides (Piperaceae) and its insect Antifeedant Activity
Applied Entomology and Zoology, 2013Co-Authors: Takashi Kitayama, Hiromi Fukumoto, Kanako Yasuda, Takeharu Kihara, Masanori MorimotoAbstract:Piper ribersoides Wall. (Piperaceae), which is called “Khua Sa khan” in the local language, is mainly grown in Laos. This plant is used as a food in Laos, but no report on its metabolites exists. Crushed stems were immersed in methanol. The ethyl acetate fraction showed potential insect Antifeedant Activity for Spodoptera litura (Fabricius) (Lepidoptera: Noctuidae), and some of the active compounds were piperine analogs. Piperine and its geometrical isomer independently showed potent Antifeedant activities, and piperine was presumably the main active compound in the methanol extract. Interestingly, we discovered that the Antifeedant Activity was reduced when they were mixed (50:50).
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synthesis and insect Antifeedant Activity of aurones against spodoptera litura larvae
Journal of Agricultural and Food Chemistry, 2007Co-Authors: Masanori Morimoto, Hiromi Fukumoto, Toki Nozoe, And Ai Hagiwara, Koichiro KomaiAbstract:A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect Antifeedant Activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 μmol/cm2. The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect Antifeedant Activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect Antifeedant Activity, but 4,5,6- and 3‘,4‘,5‘-trisubstituted compounds did not show this Activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect Antifeedant Activity against S. litura. Although the melting points did not correlate well with the insect Antifeedant Activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological Activity (pED50) and a hydrogen-bondi...
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Insect Antifeedant Activity of flavones and chromones against Spodoptera litura.
Journal of agricultural and food chemistry, 2003Co-Authors: Masanori Morimoto, Kumiko Tanimoto, Sachiko Nakano, Takayoshi Ozaki, And Ayako Nakano, Koichiro KomaiAbstract:The Antifeedant polymethylated flavones 5-hydroxy-3,6,7,8,4'-heptamethoxyflavone, 5-hydroxy-3,6,7,8-tetramethoxyflavone, and 5,6-dihydroxy-3,7-dimethoxyflavone have been isolated from the cudweed, Gnaphalium affine D. Don (Compositae). These flavonoids and authentic analogues showed insect Antifeedant Activity against the common cutworm (Spodoptera litura F.). In a previous paper, it was suggested that there was no substituent on the B-ring of the flavonoid for the beneficial Antifeedant Activity against the common cutworm. These flavonoids having a phenyl group as the B-ring and the chromone as elimination of the B-ring from the flavonoids were used to test the hypothesis of the previously described B-ring effect. The known fact is that Sculletaria baicarensis (Rutaceae) produced the 2-phenyl flavone. Test compounds and their methylated derivatives were prepared from this material for the structure-Activity relationship (SAR) study of insect Antifeedant Activity. In spite of the 2-phenyl flavonoids, some tested compounds did not show any insect Antifeedant Activity against the common cutworm, although these inactive flavonoids were deficient in the 6-substituent group on the A-ring of the flavonoid. This 6-position-substituted derivative almost showed strong insect Antifeedant Activity against common cutworm. Moreover, the tested flavonoids having a hydroxyl group as a substituent on any of the positions tended to increase the Activity. These results suggested the importance of the 6-position substitution on the flavonoid; however, hydrophilic substituents decreased the Activity. Baicalein (5,6,7-trihydroxyflavone) derivatives did not show any Activity despite having the 6-substituent derivative. Although the Activity of some chromones increased the Activity of the flavone, the bulky B-ring was a disadvantage for the Antifeedant Activity. It was suggested that the charge on C(3) and C(5) of the flavonoid was important for the biological Activity. Additionally, an adequate hydrogen bonding property, which is different from lipophilicity, was an advantage for the Activity on the basis of a QSAR analysis.
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Antifeedant Activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F.
Phytochemistry, 2002Co-Authors: Masanori Morimoto, Kumiko Tanimoto, Akiko Sakatani, Koichiro KomaiAbstract:Abstract The insect Antifeedant anthraquinone aldehyde nordamnacanthal (1,3-dihydroxy-anthraquinone-2-al) was identified in Galium aparine L., and isolated from the root powder of akane (Rubia akane), a member of the Rubiaceae. Structure–Activity relationship (SAR) studies using a series of anthraquinone analogues suggested that the aldehyde group on the anthraquinone was more important than the quinone moiety for Antifeedant Activity against the common cutworm (Spodoptera litura). High levels of nordamnacanthal were found in the seed leaf stage and in callus tissue induced from seedlings of G. aparine, but its concentration decreased with plant development. Since these compounds are natural pigments for dying textiles, we also evaluated the Antifeedant Activity against the carpet beetle (Attagenus japonicus ), a textile pest was also evaluated. While nordamnacanthal had strong Antifeedant Activity against the common cutworm, it did not show any Antifeedant Activity against the carpet beetle. The most effective Antifeedant against the carpet beetle was the major constituent in the extract of R. trictorum, lucidin-3-O-primeveroside, a food pigment.
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Structure-Activity Relationship for the Insect Antifeedant Activity of Benzofuran Derivatives
Bioscience biotechnology and biochemistry, 1999Co-Authors: Masanori Morimoto, Masamitsu Urakawa, Tatsuo Fujitaka, Koichiro KomaiAbstract:Coumaran (2,3-dihydrobenzofuran), a secondary metabolite of Cyperus nipponicus, inhibits the feeding of polyphagous insects. This secondary metabolite is regarded as one of the defensive systems of the Cyperaceae. A number of naturally occurring benzofurans that differ in their substitution pattern and oxidation state have been investigated for their ability to inhibit insect feeding by a bioassay with the common cutworm (Spodoptera litura F. Noctuidae) that applies the leaf disk method. The evaluation of the Antifeedant Activity of each test compound used the ED50 value based on the dose-response curve that was calculated with the probit method. The 2,3-dihydrobenzofuran derivative, 7-acetyl-4,6-dimethoxy-2-isopropenyl-2,3-dihydrobenzofuran, had an ED50 value of 1.3 μg (5.4×10-9 mol)/cm2 against the common cutworm. The introduction of methoxy and acetyl groups increased the insect Antifeedant Activity. Furthermore, the insect Antifeedant Activity increased with decreasing lipophilicity of the test compounds.
