ChemInform Abstract: STRUCTURE AND STEREOCHEMISTRY 4Aβ,7α,7Aβ‐NEPETALACTONE FROM NEPETA MUSSINI AND ITS RELATIONSHIP TO THE 4Aα,7α,7Aα‐ AND 4Aα,7α,7Aβ‐NEPETALACTONES FROM N. CATARIA

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

doi:10.1002/chin.198102325

Cited by 9 publications

(6 citation statements)

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“…Four nepetalactone stereoisomers with differing stereochemistry at the 4α and 7α positions are observed at different ratios in various Nepeta species (referred to as cis-cis ; cis-trans ; trans-cis ; and trans-trans ; Fig. 1 B) ( Bates et al., 1958 , Clark et al., 1997 , Eisenbraun et al., 1980 ). The ratio of the stereoisomers appears to play a role in the plants’ ability to deter insects ( Birkett et al., 2011 , Glinwood et al., 1999 ).…”

Section: Introductionmentioning

confidence: 99%

Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry

et al. 2018

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Nepetalactones are iridoid monoterpenes with a broad range of biological activities produced by plants in the Nepeta genus. However, none of the genes for nepetalactone biosynthesis have been discovered. Here we report the transcriptomes of two Nepeta species, each with distinctive profiles of nepetalactone stereoisomers. As a starting point for investigation of nepetalactone biosynthesis in Nepeta, these transcriptomes were used to identify candidate genes for iridoid synthase homologs, an enzyme that has been shown to form the core iridoid skeleton in several iridoid producing plant species. Iridoid synthase homologs identified from the transcriptomes were cloned, heterologously expressed, and then assayed with the 8-oxogeranial substrate. These experiments revealed that catalytically active iridoid synthase enzymes are present in Nepeta, though there are unusual mutations in key active site residues. Nevertheless, these enzymes exhibit similar catalytic activity and product profile compared to previously reported iridoid synthases from other plants. Notably, four nepetalactone stereoisomers with differing stereochemistry at the 4α and 7α positions – which are generated during the iridoid synthase reaction – are observed at different ratios in various Nepeta species. This work strongly suggests that the variable stereochemistry at these 4α and 7α positions of nepetalactone diastereomers is established further downstream in the iridoid pathway in Nepeta. Overall, this work provides a gateway into the biosynthesis of nepetalactones in Nepeta.

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Section: Introductionmentioning

confidence: 99%

Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry

et al. 2018

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“…In addition to Nepeta cataria , there are several other plants from the genus Nepeta that contain cat- attracting type I and II lactones (Formisano, Rigano and Senatore 2011, Regnier, Waller and Eisenbraun 1967, Bicchi, Mashaly and Sandra 1984, Eisenbraun et al 1980), of which Nepeta mussinii or catmint is arguably the best-known. Although all these plants are members of the Lamiaceae family, commonly referred to as the mint family, plants in the Nepeta genus are not closely related to plants in the Mentha genus, such as peppermint.…”

Section: Resultsmentioning

confidence: 99%

Behavioral differences among domestic cats in the response to cat-attracting plants and their volatile compounds reveal a potential distinct mechanism of action for actinidine

Bol¹,

Scaffidi

Bunnik³

et al. 2022

Preprint

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It has been known for centuries that cats respond euphorically to Nepeta cataria (catnip). Recently, we have shown that Lonicera tatarica (Tatarian honeysuckle), Actinidia polygama (silver vine) and Valeriana officinalis (valerian) can also elicit this "catnip response". The aim of this study was to learn if the behavior seen in response to these plants is similar to the response to catnip. Furthermore, we studied if these responses are fixed or if there are differences between cats. While nepetalactone was identified decades ago as the molecule responsible for the "catnip response", we know that this volatile is found almost exclusively in catnip. Therefore, we also aimed to identify other compounds in these alternative plants that can elicit the blissful behavior in cats. Bioassays with 6 cats were performed in a stress-free environment, where 6 plants and 13 single compounds were each tested for at least 100 and 17 hours, respectively. All responses were video recorded and BORIS software was used to analyze the cats' behavior. Both response duration and behavior differed significantly between the cats. While individual cats had preferences for particular plants, the behavior of individual cats was consistent among all plants. About half a dozen lactones similar in structure to nepetalactone were able to elicit the "catnip response", as were the structurally more distinct molecules actinidine and dihydroactinidiolide. Most cats did not respond to actinidine, whereas those who did, responded longer to this volatile than any of the other secondary plant metabolites, and different behavior was observed. Interestingly, dihydroactinidiolide was also found in excretions and secretions of the red fox, making this the first report of a compound produced by a mammal, that can elicit the "catnip response". A range of different cat-attracting compounds was detected by chemical analysis of plant materials but differences in cat behavior could not be directly related to differences in chemical composition of the plants. Together with among other results of habituation/dishabituation experiments, this indicates that additional cat-attracting compounds may be present in the plant materials that remain to be discovered. Collectively, these findings suggest that both the personality of the cat and genetic variation in the genes encoding olfactory receptors may play a role in how cats respond to cat-attracting plants. Furthermore, the data suggest a potential distinct mechanism of action for actinidine.

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“…13 C signals in the range of 70–80 ppm represented a sugar moiety. The assignment of the sugar as β- d -glucose was supported by comparison of the coupling constants of the protons to data from the literature [ 10 ] while the connectivity of the sugar and the cinnamic acid derivative to the nepetolactone skeleton [ 11 ] was established by HMBC cross peaks. Interpretation of coupling constants and NOESY experiments revealed the stereochemistry ( cf.…”

Section: Resultsmentioning

confidence: 99%

Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative

et al. 2015

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The chloroform extract of Valeriana wallichii (V. wallichii) rhizomes was investigated to elucidate the structures responsible for reported antileishmanial activity. Besides bornyl caffeate (1, already been reported by us previously), bioassay-guided fractionation resulted in two additional cinnamic acid derivatives 2–3 with moderate leishmanicidal activity. The structure of a novel nepetolactone derivative 4 having a cinnamic acid moiety was elucidated by means of spectral analysis. To the best of our knowledge villoside aglycone (5) was isolated from this plant for the first time. The bioassay-guided fractionation yielded two new (compounds 6–7) and two known valtrates (compounds 8–9) with leishmanicidal potential against Leishmania major (L. major) promastigotes. In addition, β-bisabolol (10), α-kessyl alcohol (11), valeranone (12), bornyl isovalerate (13) and linarin-2-O-methylbutyrate (14) were identified. This is the first report on the isolation of 4'-demethylpodophyllotoxin (15), podophyllotoxin (16) and pinoresinol (17) in V. wallichii. In total thirteen known and four new compounds were identified from the extract and their cytotoxic and antileishmanial properties were evaluated.

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ChemInform Abstract: STRUCTURE AND STEREOCHEMISTRY 4Aβ,7α,7Aβ‐NEPETALACTONE FROM NEPETA MUSSINI AND ITS RELATIONSHIP TO THE 4Aα,7α,7Aα‐ AND 4Aα,7α,7Aβ‐NEPETALACTONES FROM N. CATARIA

Abstract: Die Arbeit beschäftigt sich mit der Aufklärung der Strukturen der Stereoisomeren von Nepetalacton (I).

Cited by 9 publications

References 1 publication

Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry

Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry

Behavioral differences among domestic cats in the response to cat-attracting plants and their volatile compounds reveal a potential distinct mechanism of action for actinidine

Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative

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