- Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)(+)-pulegone and menthone
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Intense applications of synthetic insecticides for the control of adult Musca domestica have led to the insects developing resistance to most of them. In consequence, there is interest in new active ingredients as alternatives to conventional insecticides. Essential oils (EO) are potential tools for controlling M. domestica because of their effectiveness and their minimal environmental effects. In a fumigant assay, M. domestica adults treated with Minthostachys verticillata EO [LC50 = 0.5 mg/dm3; majority components by SPME-GC: (4R)(+)-pulegone (67.5%), menthone (22.3%) and (4R)(+)-limonene (3.8%)], died within 15 min or less. The terpenes absorbed by the flies and their metabolites, analyzed using SPME fiber, were (4R)(+)-limonene (LC50 = 6.2 mg/dm3), menthone (LC 50 = 1.9 mg/dm3), (4R)(+)-pulegone (LC50 = 1.7 mg/dm3) and a new component, menthofuran (LC50 = 0.3 mg/dm3), in a relative proportion of 12.4, 6.5, 35.9 and 44.2% respectively. Menthofuran was formed by oxidation of either (4R)(+)-pulegone or menthone mediated by cytochrome P450, as demonstrated by a fumigation assay on flies previously treated with piperonyl butoxide, a P450 inhibitor, which showed a decrease in toxicity of the EO, (4R)(+)-pulegone and of menthone, supporting the participation of the P450 oxidizing system in the formation of menthofuran. The enzymatic reaction of isolated fly microsomes with the EO or the (4R)(+)-pulegone produced menthofuran in both cases. Contrary to expectations, the insect detoxification system contributed to enhance the toxicity of the M. verticillata EO. Consequently, resistant strains overexpressing P450 genes will be more susceptible to either M. verticillata EO or (4R)(+)-pulegone and menthone.
- Rossi, Yanina Estefania,Canavoso, Lilian,Palacios, Sara Maria
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- Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran
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TiCl4-Bu3N-mediated condensation of ketones with α,α-dimethoxyketones afforded trialkylsubstituted 2(5H)-furanones in a one-pot manner, wherein aldol addition and furanone formation occurred sequentially; its application to straightf
- Tanabe, Yoo,Mitarai, Kumi,Higashi, Takahiro,Misaki, Tomonori,Nishii, Yoshinori
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- One-step synthesis of furan rings from α-isopropylidene ketones mediated by iodine/DMSO: An approach to potent bioactive terpenes
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The system I2/dimethyl sulfoxide mediates the one-step transformation of α-isopropylidene ketones into furan rings following a biomimetic approach. This methodology has been used for the synthesis of terpene furans such as mintfurane, curzerene, atractylon, and isoatractylon, all of them possessing interesting biological activities. The synthesis of linderazulene directly from 4,5-epoxygermacrone via a cascade reaction shows the potential of this protocol. Additionally, this compound proved to show significant ixodicidal activity.
- Salihila, Jonida,Silva, Lúcia,Pérez Del Pulgar, Helena,Quílez Molina, Ana,González-Coloma, Azucena,Olmeda, A. Sonia,Quílez Del Moral, José F.,Barrero, Alejandro F.
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p. 6886 - 6894
(2019/06/14)
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- Furanoterpene synthesis via intramolecular nitrile oxide cycloaddition reaction: a total synthesis of (+)-menthofuran
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A fused furan assembling strategy based on an intramolecular dipolar cycloaddition reaction of nitrile oxide has been applied to a total synthesis of perfumy furanomonoterpene (+)-menthofuran (1).The key cycloaddition substrates (9) and (12) are easily prepared via straightforward routes starting from (+)-citronellal and these are treated with sodium hypochlorite and p-chlorophenyl isocyanate, respectively.The cycloaddition reactions generate 10 : 1 mixture of diastereoisomeric isoxazolines (2a) and (2b) in good to excellent yields.The isoxazolines (2a,b)thus obtained are converted to (+)-menthofuran (1) by sequential reductive hydrolysis and alkaline hydrolysis (or vice versa) followed by acid treatment of the resulting β,γ-dihydroxy ketone (14).
- Shishido, Kozo,Umimoto, Koji,Takata, Takeshi,Irie, Osamu,Shibuya, Masayuki
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p. 345 - 358
(2007/10/02)
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- TOTAL SYNTHESIS OF (+)-MENTHOFURAN
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Total synthesis of optically active menthofuran, a perfumy monoterpene, has been accomplished employing the intramolecular cycloaddition-based methodology for the construction of fused furans.
- Shishido, Kozo,Takata, Takeshi,Umimoto, Koji,Shibuya, Masayuki
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- Total synthesis of (±)-chondrillin, (±)-plakorin, and related peroxy ketals. development of a general route to 3,6-dihydro-1,2-dioxin-3-ols
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Seven-step syntheses of the antitumor cyclic peroxy ketals la, 2a, chondrillin (Ib), and plakorin (2b) from (methoxymethoxy)benzene (8) have been achieved in 26-28% overall yields. The key step is the photooxygenation of enone 4 with a sun lamp using rose bengal lactone or CuSO4 as a sensitizer which gives a mixture of peroxy hemiketals 15 and 16 in 75-85% yields. Acetal formation in acidic methanol completes the syntheses of 1 and 2. The mechanism of photooxygenation was ascertained using 3-nonen-2-one (22) as a model for 4. Irradiation converts 22 to the cis-enone 23 which undergoes photoenolization to give 24. Dienol 24 undergoes a sensitized reaction with oxygen to give 29 and 30. The detailed mechanism of this last step is not known, although singlet oxygen is probably not involved. This reaction is general for any enone or enal which can undergo photoenolization to give a dienol. Peroxy hemiketals 33a, 41, and 43-46 were prepared in 30-80% yields. Peroxy ketals can be used for the synthesis of furans, diones, and pyridazines.
- Snider, Barry B.,Shi, Zhongping
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p. 1790 - 1800
(2007/10/02)
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- PRACTICAL SYNTHESIS OF MENTHOFURAN
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A 3-step synthesis of menthofuran from isopulegol in 65-70percent is reported.
- Ho, Tse-Lok,Din, Zia Ud
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p. 813 - 816
(2007/10/02)
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