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Abstract This study aimed at characterizing the modulation of skeletal muscle contraction and cardiorespiratory response of tambaqui, Colossoma macropomum submitted to baths using anaesthetic concentrations (capable of inducing fast, i.e. < 5 min, and full body immobilization) of propofol (PRP) and essential oil of Nepeta cataria (EON). For the evaluation of electromyography, electrocardiographic data, and opercular beat intensity (OBI) and rate (OBR), fish (5.6 ± 1.8 g, 8.0 ± 0.3 cm, total length) were assigned to the following groups: a) control (basal recording), b) ethanol-exposed fish (vehicle control), c) fish submitted to induction with EON at 175 μL L−1 and subsequent recovery, and d) fish submitted to induction with PRP at 4 μL L−1 and subsequent recovery. Eight fish (n = 8) per group were used. Both products induced full body immobilization and suppressed (99.9%) dorsal muscle contraction power, determining a general anaesthesia-like state. During exposure to either anaesthetic, cardiac function was transiently affected, with decreased heart rates (42–43%) and a mild arrhythmia in PRP recovering fish. Moreover, ventilatory capacity was reduced with this drug (85.3% and 59.6% decrease in OBI and OBR, respectively), yet without mortality. On the other hand, EON did not alter ECG tracings, allowing for the maintenance of normal ventilation intensity during exposure, albeit a slight increment in OBR occurred during deep anaesthesia. This study confirms propofol anaesthesia in fish and presents N. cataria essential oil as a novel and safe natural anaesthetic for juvenile Colossoma macropomum and potentially for other teleost species. Highlights • This is the first study using Nepeta cataria essential oil as an anaesthetic for fish. • Propofol and N. cataria essential oil blunted muscle contraction power in Colossoma macropomum. • Exposure to short-term baths using propofol and N. cataria essential oil did not compromise cardioventilatory function. [ABSTRACT FROM AUTHOR]

Iridoids are monoterpenes that are produced by various plants as chemical defense molecules. Lichman et al. recently described the timeline of molecular events that underpin the re-emergence of iridoid biosynthesis in an independent lineage of aromatic plants (catnip). This study represents a benchmark for studying enzyme and metabolite evolution in different clades across the tree of life. [ABSTRACT FROM AUTHOR]

Nepetalactones are accumulated as the main secondary metabolites in the majority of Nepeta species; however, their biosynthetic pathway remains to a great extent unknown, as well as their relationship to the overall physiology of these plants. Nepetalactones most certainly arise through general iridoid biosynthetic pathway leading to nepetalactol, a common precursor of all plant-derived iridoids that is formed in a reaction catalysed by iridoid synthase ( IS , EC 1.3.1.99). In this paper, we aimed to localize the sites of nepetalactone biosynthesis and accumulation by comparatively analysing the nepetalactones content and the expression of putative iridoid synthase ( NrIS ) in leaves of Nepeta rtanjensis Diklić & Milojević, a trans,cis -nepetalactone and dehydronepetalactone rich species. Another aim was to give an insight into the developmental regulation of nepetalactone biosynthesis in leaves of cultivated N. rtanjensis plants. Knowledge on the spatial-, and developmental- regulation of nepetalactone metabolism could greatly benefit potential growers by enabling them to adequately plan and manage plant cultivation, harvesting, and handling and thus increase yield of bioactive compounds. The expression profile of putative NrIS1 is highly correlated with trans,cis -nepetalactone and dehydronepetalactone content/ratio in leaves of different developmental stages. The results strongly indicate that developmental regulation of nepetalactone biosynthesis in leaves resides largely at the level of gene expression, and suggest an important role of NrIS1 . Young leaves exhibited the most intensive nepetalactone biosynthesis and accumulation, but also its conversion to dehydronepetalactone. Thus, the pattern of NL accumulation in leaves can be explained by both the rate of its biosynthesis and metabolic degradation. The gene expression patterns of NrIS1 and NrIS2 transcripts in trichomes and abraded leaves revealed trichomes as the main site of their activity. UHPLC/qqqMS profiling of nepetalactones in trichomes and abraded leaves, complemented with Raman spectroscopy and dichloromethane dipping experiment, supported glandular trichome-specific localization of nepetalactone biosynthesis and accumulation. [ABSTRACT FROM AUTHOR]

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 . [ABSTRACT FROM AUTHOR]

The aim of this study was to investigate volatile composition of the essential oil (EO) of Nepeta sintenisii Bornm. ( N. sintenisiig ), and its antioxidant, antimicrobial and cytotoxic activities. The EO was obtained by means of hydrodistillation and its components were analyzed using gas chromatography and mass spectrometry (GC/MS). The main constituents of the EO were found to be 4aα,7α,7aβ-Nepetalactone (51.74%), β-Farnesene (12.26%), 4aα,7α,7aα-Nepetalactone (8.01%), Germacrene-D (5.01%), and 4aα,7β,7aα-Nepetalactone (3.71%); these together constituted 95.81% of the extracted oil. The antimicrobial activity of the EO against eleven bacterial strains and one fungus was studied. The EO showed potent and broad-spectrum antibacterial effects against both Gram-positive and Gram-negative bacteria, and also possessed antifungal activity against Candida albicans . In vitro cytotoxicity evaluation against four cell lines of human ovarian carcinoma (A2780), cervical cancer (Hela), human colon adenocarcinoma (LS180), and human breast adenocarcinoma (MCF-7), and Human Umbilical Vein Endothelial Cells (HUVEC (as a normal cell line), showed a potent anti-proliferative activity of the oil with the lowest IC 50 value (20.37 μg/mL) belonging to the Hela cells. The IC 50 value for normal human cell line (HUVEC) was 219 μg/mL. Also, antioxidant activity of the EO was evaluated using 1,1-diphenyl-2-picrilhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) methods. The oil exhibited weak antioxidant activity in DPPH test (IC 50: 7.16 mg/mL) and FRAP (IC 50: 0.82 mM Fe 2+ /mg EO) assay. The present results suggested promising cytotoxic, antibacterial, and antifungal properties for the N. sintenisii EO. [ABSTRACT FROM AUTHOR]

Tick bites are a major public health concern due to the vector role that many tick species have in transmitting human pathogens. Synthetic repellents such as N‑diethyl-meta-toluamide (DEET) remain the standard for repellency. Still, there is a need for natural commercial alternatives with similar or better properties than DEET. We evaluated the repellency of two extracts, CR3 and CR9, derived for newly developed catnip cultivars on two tick species, Ixodes scapularis and Haemaphysalis longicornis. Dose-response in vitro assays showed that CR3 and CR9 extracts have similar repellency properties to DEET. At a 20% concentration, both CR3 and CR9 extracts exhibited a repellency of 100%. Catnip extracts maintained their repellency properties for at least 8 h. In a two-choice assay, I. scapularis, but not H. longicornis, was more sensitive to CR3 than DEET. In addition, CR3 reduces the life span of I. scapularis , suggesting that it has an acaricidal effect on ticks. In summary, CR3 and CR9 catnip extracts are promising tick repellents that should be further developed, alone or in combination with other tick repellents, and tested for their use as tick repellents for humans. [ABSTRACT FROM AUTHOR]

Highlights: [•] N. elliptica oil has dominant presence of (7R)-trans,trans-nepetalactone (1). [•] The antifungal activity of the oil and 1 was tested against phytopathogenic fungi. [•] Oil and 1 showed high inhibitory activity against H. maydis and F. oxysporum. [•] The activity may be accredited mainly to the presence of nepetalactone (1). [•] The oil and 1 have potential as natural fungicide for controlling fungal pathogens. [Copyright &y& Elsevier]

Rapid micropropagation of Nepeta rtanjensis, N. sibirica and N. nervosa was performed. Qualitative and quantitative nepetalactone content in methanol extracts of in vitro grown plants was analysed by reverse-phase HPLC coupled with UV and MS detection. Only trans,cis-nepetalactone was detected in shoots of N. rtanjensis, while cis,trans-nepetalactone stereoisomer was present in N. sibirica. No nepetalactone was observed in shoots of N. nervosa. The antimicrobial activity of methanol extracts, against eight bacterial and eight fungal species, was evaluated. All the tested extracts showed significant antibacterial and strong antifungal activity. However, N. rtanjensis extract exhibited the best antimicrobial potential. [Copyright &y& Elsevier]

Abstract: The chemical composition of Matricaria chamomilla L. and Nepeta cataria L. essential oils was determined by GC–MS on an apolar stationary phase by comparison of the characteristic fragmentation patterns with those of the Wiley 275L database. The GC–MS chromatograms were compared with those obtained by fast GC equipped with a direct resistively heated column (Ultra Fast Module 5% phenyl, 5m×0.1mm, 0.1μm film thickness). Analytical conditions were optimised to reach a good peak resolution (split ratio=1:100), with analysis time lower than 5min versus 35–45min required by conventional GC–MS. The fast chromatographic method was completely validated for the analysis of mono- and sesquiterpene compounds. Essential oils were then fractionated by column chromatography packed with silica gel. Three main fractions with high degree of purity in E-β-farnesene were isolated from the oil of M. chamomilla. One fraction enriched in (Z,E)-nepetalactone and one enriched in β-caryophyllene were obtained from the oil of N. cataria. These semiochemical compounds could act as attractants of aphid’s predators and parasitoids. [Copyright &y& Elsevier]

Abstract: Volatiles released by seedlings of Norway spruce infested with the aphid Cinara pilicornis were analyzed using SPME–GC–MS. Among the stress-induced compounds released by the host plant, citronellol, cis–trans-nepetalactone and cis–trans-nepetalactol was found. These compounds originated from the aphids and they were assumed to be pheromone components for this aphid species. To determine the relative stereochemistry of the nepetalactone, a diagnostic method was developed. The method was based on multivariate analysis of tabulated relative intensities of mass fragments of the four nepetalactone diastereomers. In the practical method described, a few pairs of fragments in the mass spectra were compared and, in combination with the Kovat''s index, were used to unambiguously identify the relative stereochemistry of the nepetalactone. [Copyright &y& Elsevier]

Abstract: Electroantennogram (EAG) responses were recorded from alate fundatrigeniae (spring migrants), gynoparae (the winged female form that produces sexual females) and males, the three migratory forms of the damson-hop aphid, Phorodon humuli (Schrank). EAG responses of gynoparae and males showed typical dose response characteristics to (E)-2-hexenal, (-)-R-carvone, hexanenitrile and (1RS,4aR,7S,7aS)-nepetalactol, the sex pheromone of this species. The 34 plant volatiles elicited broadly similar EAG response profiles in the three migratory forms. Green leaf volatiles produced large responses in all forms; however, the relative order of responsiveness varied. EAG responses to isomers of the monoterpene carvone differed between forms, with males being most, and spring migrants least, responsive. The hop-plant volatile and aphid alarm pheromone, (E)-β-farnesene, evoked similar EAG responses in all forms. By contrast, males were most responsive to the three sex pheromone components, (-)-(4aS,7S,7aR)-nepetalactol, (+)-(4aS,7S,7aR)-nepetalactone and (1RS,4aR,7S,7aS)-nepetalactol. Males were no more responsive to their own sex pheromone, (1RS,4aR,7S,7aS)-nepetalactol, than to the other aphid sex pheromone components tested. Spring migrants and gynoparae also responded to the three sex pheromone components. This study indicates that migratory forms of P. humuli detect a wide range of volatile compounds, and that they are equally well-adapted for the detection of volatiles associated with host and non-host plants and with other species of aphid. [Copyright &y& Elsevier]

Electrophysiological responses of three different olfactory sensilla (proximal primary rhinaria (PPR), distal primary rhinaria (DPR) and secondary rhinaria (SR)) to the sex pheromone components, nepetalactol, nepetalactone, and a plant volatile, (E)-2-hexenal, were investigated in four different morphs of the black bean aphid, Aphis fabae Scopoli. The DC responses recorded directly from the antennal sensilla and termed electrosensillograms (ESGs) were generally much larger (up to 14 mV) than electroantennogram (EAG) responses (up to 2.5 mV). Characteristic morph-specific response profiles to these compounds were observed in each type of rhinarium and response waveforms were different between (E)-2-hexenal and the sex pheromone components. (E)-2-Hexenal elicited the largest responses at PPR, while nepetalactol and nepetalactone elicited the largest responses at SR in gynoparae and males. Nepetalactol and nepetalactone also showed significant activities on DPR and PPR in all morphs. In contrast, (E)-2-hexenal had almost no activity on SR. However, almost all of the SR investigated in males and gynoparae were sensitive to both nepetalactol and nepetalactone. A small sub-set of male SR responded mainly to nepetalactol. SR of winged virginoparae did not respond to the sex pheromone compounds. Paraffin oil (the solvent control) also elicited significant responses at PPR in virginoparae but not in other morphs. In a further experiment, SR of winged virginoparae showed no response to 30 other plant volatile compounds or the alarm pheromone component, (E)-β-farnesene. Nepetalactol and nepetalactone had similar dose-response profiles in the SR of gynoparae. The results indicate that SR in males and gynoparae are highly specialised to detect sex pheromone compounds, while the DPR and PPR are relatively broadly tuned to both plant volatiles and sex pheromone components. The presence of SR in winged virginoparae that are not responsive to sex pheromone components, alarm pheromone, or any of the plant volatile compounds tested may indicate a possible role of these sensilla to detect, as yet, unknown compound(s) with a high specificity. The present study also suggests that PPR may play a role in detecting paraffin-related compounds such as cuticular hydrocarbons of plants. [Copyright &y& Elsevier]

Electroantennogram (EAG) responses to the aphid sex pheromone components, (1R,4aS,7S,7aR)-nepetalactol and (4aS,7S,7aR)-nepetalactone, and a plant volatile, (E)-2-hexenal, were investigated at three different positions (5/6th, 4/5th and 3/4th inter-segmental regions) along the antennae of four different morphs in two host-alternating aphid species, Aphis fabae Scopoli and Rhopalosiphum padi (L.). Position-dependent and morph-specific EAG responses were elicited in both species. The nepetalactol and nepetalactone isomers elicited large EAG responses at all three recording positions in males of both species, such that primary rhinaria as well as secondary rhinaria appeared to respond. Asexual female morphs showed relatively smaller EAG responses to these compounds. The secondary rhinaria, which have been reported as sex pheromone receptors in males, were not very different in their number and distribution between gynoparae and alate virginoparae, but the gynoparae showed significantly larger EAG responses to nepetalactol and nepetalactone. The alate virginoparae showed EAG responses that were similar to those of apterous virginoparae, which lack secondary rhinaria. Taking the EAG response profiles together with the distribution of the secondary rhinaria, it is suggested that the function of secondary rhinaria differs between the morphs. Secondary rhinaria appear to detect sex pheromone components in males and gynoparae but not in the alate virginoparae. If they are functional in the latter morph, they are likely to play a role in detecting specific, but as yet unknown, volatile compounds. Some 30 plant volatiles were tested but none evoked an EAG response that could be allocated to the secondary rhinaria. In contrast to the very different EAG response profiles to the pheromone compounds between morphs, EAG responses to (E)-2-hexenal were similar in all forms and both species. These findings suggest that this plant volatile was detected only by the two primary rhinaria, which are common to all morphs. The present study showed that EAG responses were not a simple summation of receptor potentials between recording and reference electrodes in aphids. The localised distribution pattern of olfactory receptor neurones around the recording electrode was also likely to contribute to the EAG responses. [ABSTRACT FROM AUTHOR]

Abstract: 4S,4aS,7S,7aR; 4R,4aS,7S,7aR; 4S,4aS,7S,7aS, and 4R,4aS,7S,7aS diastereomers of iridomyrmecin have been prepared in 5 steps from 4aS,7S,7aR and 4aS,7S,7aS-nepetalactones, major components of catnip oil. 4S,4aS,7S,7aR and 4R,4aS,7S,7aR-iridomyrmecin have been identified as defensive compounds from Iridomyrmex ants. [Copyright &y& Elsevier]

1R,2S,5R,8R; 1R,2S,5R,8S; 1S,2S,5R,8R; and 1S,2S,5R,8S-Iridodials have been prepared in five steps from 4aS,7S,7aR and 4aS,7S,7aS-nepetalactones, major components of catnip oil. 1R,2S,5R,8R-Iridodial has been identified as a male-produced male-aggregation pheromone for Chrysopa oculata, the first pheromone of any kind identified for lacewings. [Copyright &y& Elsevier]