Naturally Occurring Insecticides, Myristicin, an Insecticide and Synergist Occurring Naturally in the Edible Parts of Parsnips

Lichtenstein, E. P.; Casida, J. E.

doi:10.1021/jf60129a017

Cited by 89 publications

(51 citation statements)

References 5 publications

(7 reference statements)

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“…The functional moiety for the activity of the brasiliamides was expected to be a 3-methoxy-4,5-methylenedioxybenzyl moiety, namely a piperonyl group, since such natural compounds having a piperonyl group as myristicin and dillapiole have been reported as insecticides. 10) However, the activity of dihydrobrasiliamide B (3) was 400 mg W g of diet, weaker than that of 1, suggesting that a double bond in the tetrahydropyrazine ring was an essential moiety in these structures.…”

Section: Convulsive Activity Of 1-3mentioning

confidence: 97%

New Convulsive Compounds, Brasiliamides A and B, from Penicillium brasilianum Batista JV-379

Fujita

Makishima

Akiyama

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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New convulsive compounds, brasiliamides A (1) and B (2), were isolated by activity-guided fractionation from okara fermented with a soil isolate of Penicillium brasilianum Batista JV-379. Their structures were elucidated on the basis of spectral and chemical evidence and by X-ray crystallography of the hydrogenated product of 2. In the 1 H-and 13 C-NMR spectra of 2, the signals were complicated, all being doubled or broadened in several deuterated solvents at room temperature. The conformational change of 2 was clariˆed as the rotational isomerization of amide bonds in solution by NMR measurements at various temperatures. Four rotamers of 2 at two amide bonds were presented at -609 C in CDCl 3 , whereas only two isomers were apparent at room temperature, owing to rapid rotation of one of the amide bonds. Brasiliamides A and B respectively showed convulsive activity against silkworms with ED 50 values of 300 and 50 mg W g of diet.

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Section: Convulsive Activity Of 1-3mentioning

confidence: 97%

New Convulsive Compounds, Brasiliamides A and B, from Penicillium brasilianum Batista JV-379

Fujita

Makishima

Akiyama

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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“…The phenylpropanoid family is rich in biologically active compounds. Myristicin 2 was shown to be an insecticide (Lichtenstein and Casida, 1963;Lichtenstein et al, 1974;Berenbaum and Neal, 1985) and to synergize the activity of synthetic insecticides (Lichtenstein et al, Table 3, the most sensitive strain was S. simulans with a diameter of inhibition for the crude extract of 28 mm. This is relatively close to that obtained for 30 mg of ampicillin.…”

Section: Resultsmentioning

confidence: 99%

An antibacterial and antifungal phenylpropanoid from Carum montanum (Coss. et Dur.) Benth. et Hook.

Laouer

Elkolli

Prado

et al. 2009

Phytotherapy Research

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The volatile constituents of the aerial parts of Carum montanum (Coss. et Dur.) Benth. et Hook. were analysed by GC-FID and GC-MS, and the main component was isolated and identified as nothoapiole. The antibacterial and antifungal activities of this compound and of the total oil were investigated against Gram-negative (P. aeruginosa, E. coli), Gram-positive (E. faecalis, S. aureus, S. epidermitis, S. saprophyticus, S. simulans, S. lugdunensis) bacteria and on one strain of fungus (C. tropicalis).

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“…The juvenile hormone mimic, 1-(3,4-methylenedioxyphenyl)-trans-3-decene(1) (to which we have assigned the trivial name juvadecene in accord with previous terminology) identified in this study can be added to the known battery of biologically active components previously described in this plant [I, [9][10][11].…”

Section: Discussionmentioning

confidence: 99%

Juvadecene: Discovery of a juvenile hormone mimic in the plant, Macropiper excelsum

Nishida

Bowers

Evans

1983

Arch Insect Biochem Physiol

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A compound with significant insect juvenile hormone activity was isolated from the plant, Macropiper excelsurn. The chemical structure was determined by spectral methods to be 1-(3,4methylenedioxyphenyl)-trans-3-decene(l), and confirmed by synthesis. The hormonally active substance applied topically to last (fifth)-instar nymphs of the milkweed bug (Oncopeltus fasciatus) induced a supernumerary metamorphosis at 30 Fg. Higher doses were toxic.

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Naturally Occurring Insecticides, Myristicin, an Insecticide and Synergist Occurring Naturally in the Edible Parts of Parsnips

Cited by 89 publications

References 5 publications

New Convulsive Compounds, Brasiliamides A and B, from Penicillium brasilianum Batista JV-379

New Convulsive Compounds, Brasiliamides A and B, from Penicillium brasilianum Batista JV-379

An antibacterial and antifungal phenylpropanoid from Carum montanum (Coss. et Dur.) Benth. et Hook.

Juvadecene: Discovery of a juvenile hormone mimic in the plant, Macropiper excelsum

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