Structure and stereochemistry 4a.beta.,7.alpha.,7a.beta.-nepetalactone from Nepeta mussini and its relationship to the 4a.alpha.,7.alpha.,7a.alpha.- and 4a.alpha.,7.alpha.,7a.beta.-nepetalactones from N. cataria

Eisenbraun, E. J.; Browne, Clinton E.; Irvin-Willis, R. L.; Mcgurk, D. J.; Eliel, Ernest L.; Harris, David L.

doi:10.1021/jo01307a016

Cited by 58 publications

(16 citation statements)

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“…1 ) [ 9 ]. Relative configurations of cis -fused nepetalactones and some related derivatives have been investigated [ 10 – 11 ]. Nepetalactone and cis - as well as trans -fused dihydronepetalactones have been isolated from the leaves and galls of the plant Actinidia polygama [ 8 ].…”

Section: Resultsmentioning

confidence: 99%

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

Zimmermann¹,

Hilgraf²,

Lehmann³

et al. 2012

Beilstein J. Org. Chem.

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SummaryStarting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1-cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7.

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Section: Resultsmentioning

confidence: 99%

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

Zimmermann¹,

Hilgraf²,

Lehmann³

et al. 2012

Beilstein J. Org. Chem.

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“…␣-Caryophyllene was tentatively identiÞed by the match of its mass spectrum with an available spectrum in the Wiley 138K mass spectral database. E,Z and Z,E nepetalactone were identiÞed by comparison of proton NMR spectra from a Varian VXR-300 Spectrometer to NMR data reported in previous literature (Eisenbraun et al 1980).…”

Section: Methodsmentioning

confidence: 99%

Catnip, <I>Nepeta cataria</I> (Lamiales: Lamiaceae)—A Closer Look: Seasonal Occurrence of Nepetalactone Isomers and Comparative Repellency of Three Terpenoids to Insects

Schultz¹,

Simbro²,

Belden³

et al. 2004

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Evidence of repellent properties in catnip, Nepeta cataria L., to flies and cockroaches was observed in preliminary studies. This study compared catnip essential oil from steam distillation and elemol, a major constituent of osage orange essential oil, to current commercial repellents. These comparative studies found both the catnip steam distillate and elemol to be as good, and in some cases better, at repelling house flies, Musca domestica L., and American cockroaches, Periplaneta americana L., than N,N-diethyl-m-toluamide (DEET) or citronellal. Both short-term and long-term repellency bioassays were used to assess repellency. Catnip essential oil showed greater repellency than DEET and citronellal in the short term. Extended repellency bioassays showed elemol to be more repellent than catnip steam distillate, citronellal, and DEET. Nepetalactone, the major constituent of catnip essential oil, is present as two isomers, and previous studies have shown the E,Z-nepetalactone [2-(2-hydroxy-1-methylethenyl)-5-methyl-cyclopentanecarboxylic acid delta lactone] isomer to be even more repellent to cockroaches than the dominant isomer, Z,E-nepetalactone. This study examined the seasonal variation of the two isomers, Z,E-and E,Z-nepetalactone, in catnip. Samples of fresh catnip mature leaves, immature leaves, and stems were steam-distilled separately, and isomer composition was analyzed using high-performance liquid chromatography and gas chromatography (GC). An analysis of variance (ANOVA) showed significant differences by week. The mature leaf essential oil samples were tested in a repellency bioassay and exhibited significant repellency to German cockroaches, Blattella germanica L. The catnip floral volatiles were sampled using solid phase microextraction, and analysis with GC/ mass spectrometry showed the presence of Z,E-nepetalactone, E,Z-nepetalactone, and β-caryophyllene as the major constituents. Phytophagous insects and potential pollinators present on sampling dates were recorded.ABSTRACT Evidence of repellent properties in catnip, Nepeta cataria L., to ßies and cockroaches was observed in preliminary studies. This study compared catnip essential oil from steam distillation and elemol, a major constituent of osage orange essential oil, to current commercial repellents. These comparative studies found both the catnip steam distillate and elemol to be as good, and in some cases better, at repelling house ßies, Musca domestica L., and American cockroaches, Periplaneta americana L., than N,N-diethyl-m-toluamide (DEET) or citronellal. Both short-term and long-term repellency bioassays were used to assess repellency. Catnip essential oil showed greater repellency than DEET and citronellal in the short term. Extended repellency bioassays showed elemol to be more repellent than catnip steam distillate, citronellal, and DEET. Nepetalactone, the major constituent of catnip essential oil, is present as two isomers, and previous studies have shown the E,Z-nepetalactone [2-(2-hydroxy-1-methylethenyl)-5-methyl-cyclopentaneca...

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“…(CDC13) 91.6 (C-l), 139.5 (C-3), 114.3 (C-4), 32.0 (C-5), 39.8 (C-6), 74.9 (C-7), 40.5 (C-8), 45.0 (C-9), 12.8 (C-10), 63.8(C-11), 171.0(C-1')", 43.5 (C-2')b, 25.8(C-3'), 22.4(C-4'), 173.0(C-1")', 43.6(C-2")b, 25.8(C-3">, 22.4 (C-4"). Nardostachys cbinensis (Valerianaceae) (6) 5 7,7-O-DIHYDROEBULOSIDE CHoOglu 2 10 446.49 {a] -73.8°(?)…”

mentioning

confidence: 99%

Iridoids. An Updated Review, Part II

Boros¹,

Stermitz²

1991

J. Nat. Prod.

205

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Structure and stereochemistry 4a.beta.,7.alpha.,7a.beta.-nepetalactone from Nepeta mussini and its relationship to the 4a.alpha.,7.alpha.,7a.alpha.- and 4a.alpha.,7.alpha.,7a.beta.-nepetalactones from N. cataria

Cited by 58 publications

References 0 publications

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

Catnip, <I>Nepeta cataria</I> (Lamiales: Lamiaceae)—A Closer Look: Seasonal Occurrence of Nepetalactone Isomers and Comparative Repellency of Three Terpenoids to Insects

Iridoids. An Updated Review, Part II

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