Structural Elucidation of Presilphiperfolane-7α,8α-diol, a Bioactive Sesquiterpenoid from Pulicaria vulgaris: A Combined Approach of Solvent-Induced Chemical Shifts, GIAO Calculation of Chemical Shifts, and Full Spin Analysis.

Structural elucidation of a new triquinane sesquiterpenoid, presilphiperfolane-7α,8α-diol, 1a, isolated from Pulicaria vulgaris, was accomplished by combining solvent-induced removal of chemical shift degeneracy and computational (DFT-GIAO) prediction of NMR spectra with the analysis of 1H NMR splitting patterns. In addition to extensive NMR experiments (in 10 different solvents), MS, and FTIR, the identity of 1a was also confirmed by chemical transformations. The applied approach can facilitate structural elucidation of organic molecules and decrease the probability of an erroneous identification, permitting an unambiguous stereochemical elucidation and full NMR assignment. The pharmacological/toxicological profile of 1a was evaluated in several different models.

Chemical Composition of the Essential Oil and Diethyl Ether Extract of Trinia glauca (L.) Dumort. (Apiaceae) and the Chemotaxonomic Significance of 5-O-Methylvisamminol.

Analyses by GC, GC/MS, and NMR spectroscopy (1D- and 2D-experiments) of the essential oil and Et2O extract of Trinia glauca (L.) Dumort. (Apiaceae) aerial parts allowed a successful identification of 220 constituents, in total. The major identified compounds of the essential oil were (Z)-falcarinol (10.6%), bicyclogermacrene (8.0%), germacrene D (7.4%), δ-cadinene (4.3%), and ß-caryophyllene (3.2%), whereas (Z)-falcarinol (47.2%), nonacosane (7.4%), and 5-O-methylvisamminol (4.0%) were the dominant constituents of the extract of T. glauca. One significant difference between the compositions of the herein and the previously analyzed T. glauca essential oils (only two reports) was noted. (Z)-Falcarinol was the major constituent in our case, whereas germacrene D (14.4 and 19.6%) was the major component of the previously studied oils. Possible explanations for this discrepancy were discussed. 5-O-Methylvisamminol, a (furo)chromone identified in the extract of T. glauca, has a limited occurrence in the plant kingdom and is a possible excellent chemotaxonomic marker (family and/or subfamily level) for Apiaceae.

Essential-Oil Constituents and Alkanes of Cephalaria ambrosioides Roem. & Schult. (Family Caprifoliaceae, Subfamily Dipsacaceae) and (Chemo)taxonomic Discernment of the Subfamilies Dipsacaceae and Morinaceae.

Herein, the results of the first study of the volatile and alkane profiles of Cephalaria ambrosioides Roem. & Schult. (Caprifoliaceae, subfamily Dipsacaceae) were reported. The GC-FID and GC/MS analyses of the essential oils hydrodistilled from leaves and stems (CA1) and flowers (CA2) of C. ambrosioides allowed the identification of 284 different components. The main compounds of the studied oil samples were palmitic acid (24.3 and 32.5% for CA1 and CA2, resp.), hexahydrofarnesyl acetone (1.4 and 10.8% for CA1 and CA2, resp.), (Z)-hex-3-en-1-ol (7.0 and <0.1% for CA1 and CA2, resp.), and linoleic acid (1.9 and 6.5% for CA1 and CA2, resp.). Essential-oil compositional data of selected plant species belonging to the Dipsacaceae (15) and Morinaceae (2) subfamilies were used to resolve taxonomical ambiguities regarding the genus Cephalaria and its infrageneric relations, especially concerning the subfamily Morinaceae (formerly a genus within Dipsacaceae). The results of multivariate statistical analyses (25 different essential-oil samples) supported the exclusion of Morina species from the Dipsacaceae subfamily. The relative abundances of alkanes from n-, iso-, and anteiso-series followed a (distorted) Gaussian-like distribution and suggested that the biosyntheses of n- and branched alkanes in C. ambrosioides are possibly not controlled by the same elongase. Also, the obtained results suggested that there was a difference in the biosynthesis/accumulation of alkanes in the vegetative and reproductive parts of C. ambrosioides.

(Chemotaxonomic) Implications of Postharvest/Storage-Induced Changes in Plant Volatile Profiles--the Case of Artemisia absinthium L. Essential Oil.

The plant volatile profile and the essential-oil chemical composition change during the storage of plant material. The objective of this study was to develop a mathematical model able to predict, explain, and quantify these changes. Mathematical equations, derived under the assumption that the essential oil contained within plant material could be treated as an ideal solution (Raoult's law), were applied for tracking of postharvest changes in the volatile profile of Artemisia absinthium L. (the essential oils were analyzed by GC-FID and GC/MS). Starting from a specific chemical composition of an essential-oil sample obtained from plant material after a short drying period (typically 5-10 d), and by using the equations derived from this model, one could easily predict evaporation-induced changes in the volatile profile of the plant material. Based on the composition of the essential-oil sample obtained after a given storage time t, it is possible to identify those components that were involved in chemical reactions, both as reactants and possible products. The established model even allowed the recognition of pairs of transformation, i.e., 'daughter' products and their 'parent' compounds. The obtained results highlight that the essential-oil composition is highly dependent on the storage period of any plant material and urges caution in different types of phytochemical studies, especially chemotaxonomic ones, or practical application.

(Un)targeted metabolomics in Asteraceae: probing the applicability of essential-oil profiles of senecio L. (Senecioneae) taxa in chemotaxonomy.

The possible applicability of (un)targeted metabolomics (volatile metabolites) for revealing taxonomic/evolutionary relationships among Senecio L. species (Asteraceae; tribe Senecioneae) was explored. Essential-oil compositional data of selected Senecio/Senecioneae/Asteraceae taxa (93 samples in total) were mutually compared by means of multivariate statistical analysis (MVA), i.e., agglomerative hierarchical clustering and principal component analysis. The MVA input data set included the very first compositional data on the essential oil extracted from the aerial parts of S. viscosus L. as well as on four different Serbian populations of S. vernalis Waldst. & Kit. (oils from aerial parts and roots; eight samples in total). This metabolomic screening of Senecio/Senecioneae/Asteraceae species (herein presented results and data from the literature) pointed to short-chain alk-1-enes (e.g., oct-1-ene, non-1-ene, and undec-1-ene), with up to now restricted general occurrence in Plantae, as characteristic chemotaxonomic markers/targets for future metabolomic studies of Senecio/Senecioneae taxa. The MVA additionally showed that the evolution of the terpene metabolism (volatile mono- and sesquiterpenoids) within the Asteraceae tribe Senecioneae was not genera specific. However, the MVA did confirm plant-organ specific production/accumulation of volatiles within S. vernalis and suggested the existence of at least two volatile chemotypes for this species.

A 'low-level' chemotaxonomic analysis of the plant family Apiaceae: the case of Scandix balansae Reut. ex Boiss. (tribe Scandiceae).

Analyses by GC and GC/MS of an essential-oil sample obtained from dry fruits of Scandix balansae Reut. ex Boiss. allowed the identification of 81 components, comprising 91.4% of the total oil composition. Interestingly, the major identified volatile compounds were medium-chain-length n-alkanes, i.e., tridecane (6.7%), pentadecane (13.4%), and heptadecane (19.3%), and a long-chain homolog nonacosane (7.6%). A number of minor oil constituents, among them tetradecyl 3-methylbutanoate, and octadecyl 2-methylpropanoate, 3-methylbutanoate, and pentanoate, turned out to have a restricted natural occurrence not only in umbellifers but also in the Plant Kingdom, whereas the last ester is a new natural compound in general. The identity of these rare plant constituents that present excellent chemotaxonomic marker candidates for Scandix species was unambiguously confirmed by co-injection of the oil sample with appropriate standards, which were synthesized for this purpose and fully characterized ((1) H- and (13) C-NMR, IR, MS). To explore the possible applicability of the essential oils' compositional data in the taxonomy of Apiaceae, the herein studied and additional 58 oils obtained from Scandiceae taxa were compared using multivariate statistical analyses (MVA). MVA demonstrated that the evolution of the volatiles' metabolism of Scandiceae taxa was neither genera-specific nor follows their morphological evolution.

α-Linalool - a marker compound of forged/synthetic sweet basil (Ocimum basilicum L.) essential oils.

BACKGROUND: Ocimum basilicum L. (sweet basil) is known to occur as several chemotypes or cultivars that differ in their essential oil composition. The surprising discovery of 3,7-dimethylocta-1,7-dien-3-ol, the rare α isomer of the well-known monoterpene alcohol ß-linalool (3,7-dimethylocta-1,6-dien-3-ol), in samples of Serbian basil oil provoked an investigation of the origin of α-linalool in these samples. Three scenarios were considered, namely (a) the existence of a new natural chemotype, (b) an artefactual formation during the isolation procedure and (c) the case of a synthetic/forged oil. RESULTS: Noteworthy amounts (15.1-16.9%) of pure α-linalool were isolated from a commercial sample of basil oil, and detailed spectral analyses (MS, IR, (1) H and (13) C NMR) unequivocally confirmed its identity. The analysis by GC and GC/MS of an additional 20 samples of different O. basilicum oils commercially available on the Serbian market or isolated from plant material cultivated in Serbia resulted in the identification of 149 compounds. The obtained compositional data were compared using multivariate statistical analysis to reveal the possible existence of a new basil chemotype. CONCLUSION: The results of the chemical and statistical analyses give more pro arguments for the synthetic/forged oil hypothesis and suggest that α-linalool could be used as a marker compound of such O. basilicum oils.

Synthetic Analogs of the Sponge Sesterterpenoid Alotaketal C are Potent Inhibitors of SARS-CoV-2 Omicron BA.1 and BA.5 Infections of Human Lung Cells.

The protein kinase C-activating sponge natural product alotaketal C (1) potently inhibits the infection of human Calu-3 lung cells by SARS-CoV-2 Omicron BA.1 and BA.5 variants. Simplified analogs of 1 have been synthesized and tested for anti-SARS-CoV-2 activity providing SAR data for the antiviral pharmacophore of 1. Analogs 19 and 23, which are missing the C-11 substituents in 1 and have modified C-13 appendages, are ∼2- to 7-fold more potent than 1 and have equal or larger selectivity indices.

Chemical composition of Hypericum rumeliacum Boiss. essential oil. A new chemotype of this pharmacologically valuable species?

Analysis by GC and GC/MS of the essential-oil samples obtained from dry above-ground parts of Hypericum rumeliacum Boiss. (collected in the flowering and fruit-forming vegetative stages) allowed the identification of 212 components in total, comprising ≥97.8% of the total oil composition. In the flowering phase, the major identified volatile compounds were undecane (6.6%), dodecanal (10.8%), and germacrene D (14.1%), whereas α-pinene (7.3%), ß-pinene (26.1%), (Z)-ß-ocimene (8.5%), (E)-ß-ocimene (10.2%), bicyclogermacrene (7.7%), and germacrene D (15.1%) were dominant in the fruit-forming phase. Some of the minor constituents found in the studied oil samples (e.g., a homologous series of four 6-alkyl-5,6-dihydro-2H-pyran-2-ones, i.e., massoia dodeca-, trideca-, tetradeca-, and hexadecalactones) have a restricted occurrence in the Plant Kingdom, and their presence in Hypericum L. spp. has not been previously reported. The chemical compositions of the herein studied additional 34 oils obtained from selected Hypericum taxa were compared using multivariate statistical analysis (agglomerative hierarchical cluster analysis and principal component analysis). The results of these statistical analyses could not be used to either confirm or discard the existence of different H. rumeliacum chemotypes. However, they have implied that the volatile profile of this plant species is determined by the stage of its phenological development.

Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): biosynthetical and chemotaxonomical aspects.

Analysis by GC and GC/MS of the essential oil obtained from above-ground parts of Micromeria dalmatica Benth. allowed the identification of 116 components, comprising 93.6% of the total oil composition. The major compounds are 3-oxygenated p-menthane monoterpenes and were identified as pulegone (29.6%), menthone (11.7%), and piperitenone (10.8%). The chemical composition of this and additional 30 oils obtained from selected Micromeria Benth. taxa were compared by using multivariate statistical analysis (agglomerative hierarchical cluster analysis and principal component analysis (PCA)). The results of statistical analyses, as well as the domination of different concurrent p-menthane-skeleton-type monoterpene biosynthetical sub-branches in the compared M. dalmatica samples, implied the occurrence of at least two different chemotypes of the mentioned species.

Sulfur-containing ferrocenyl alcohols and oximes: new promising antistaphylococcal agents.

A small library containing four different series of new ferrocene derivatives, 2-(alkylsulfanyl)-1-ferrocenylethan-1-ols, 3-(alkylsulfanyl)-1-ferrocenylpropan-1-ols, (E)- and (Z)-2-(alkylsulfanyl)-1-ferrocenylethan-1-one oximes, and (E)- and (Z)-3-(alkylsulfanyl)-1-ferrocenylpropan-1-one oximes (36 different compounds in total) was synthesized starting from ferrocene and the corresponding sulfanyl acids. All compounds were spectrally (IR and NMR) and electrochemically characterized. In general, the obtained compounds were found to exhibit very strong antimicrobial activities (broth microdilution assay) against the tested microorganisms (six common human pathogens). For the majority of the tested compounds, the determined MIC values were either under the 10 µg/ml MIC limit recognized to delimit efficient antimicrobials or were comparable to/lower than those of the used positive controls (tetracycline/nystatin). The most susceptible organism was found to be Staphylococcus aureus with MIC values even reaching 0.001 µg/ml. The presence of -CH(OH)(CH(2))(n)S- and -CH(=NOH)(CH(2))(n)S- (n=1 or 2) structural fragments seems to be essential for the observed strong activity (introduction of hydroxyimino and alcohol functionalities, instead of the keto function, resulted in a more than 10(5)-fold increase in antistaphylococcal activity in some instances). Nevertheless, a possible influence of the ferrocenyl-core redox chemistry (Fe(2+)/Fe(3+)) should not be disregarded. The studied alcohols exhibited a reversible one-electron redox couple at almost the same position as ferrocene, while the hydroxyimino group conjugated with cyclopentadienyl ring considerably shifted the redox potential of the ferrocene unit in oximes.

The most frequently encountered volatile contaminants of essential oils and plant extracts introduced during the isolation procedure: fast and easy profiling.

INTRODUCTION: Unfortunately, contaminants of synthetic/artificial origin are sometimes identified as major constituents of essential oils or plant extracts and considered to be biologically active native plant metabolites. OBJECTIVE: To explore the possibility of early recognition and to create a list of some of the most common semi-volatile contaminants of essential oils and plant extracts. METHODOLOGY: Detailed GC and GC-MS analyses of the evaporation residues of six commercially available diethyl ethers and of a plastic bag hydrodistillate were performed. Average mass scans of the total ion chromatogram profiles of the analysed samples were performed. RESULTS: Almost 200 different compounds, subdivided into two groups, were identified in the analysed samples: (i) compounds that could be only of a synthetic/artificial origin, such as butylated hydroxytoluene and o-phthalic acid esters, i.e. requiring exclusion from the list of identified plant constituents; (ii) compounds possibly of synthetic and/or natural plant origin, i.e. compounds derived from the fatty acid metabolism or products of anaerobic intracellular/microbial fermentation. Average mass scans of the total ion chromatogram profiles provide meaningful and convenient information on uncovering important solvent-derived contamination. CONCLUSION: A database of the most common semi-volatile contaminants of essential oils and plant extracts has been generated that provides information on the likelihood of rejection or acceptance of contaminants as possible plant constituents. The suggested average mass scan approach enables fast and easy profiling of solvents, allowing even inexperienced researchers to pinpoint contaminants.

Commercial Carlinae radix herbal drug: botanical identity, chemical composition and antimicrobial properties.

CONTEXT: Carlinae radix is an herbal drug, commonly used by the locals in southeastern Serbia for the treatment of respiratory and urogenital diseases and, externally, for various skin conditions. There still seems to be no detailed studies correlating the chemical composition of this drug and its ethnopharmacological uses. OBJECTIVE: Chemical composition, antimicrobial activity and mode of action of C. radix essential oil, isolated from commercial samples (confirmation of whose true biological identity was also the aim of this work) were analyzed. Antimicrobial potential of decoctions (extracts prepared by boiling plant material in a given solvent), used in ethnomedicine preferentially to the pure essential oil, was also investigated. MATERIALS AND METHODS: The essential oil obtained by hydrodistillation was screened for antimicrobial activity by disc diffusion and broth microdilution methods. Effects of the oil on the growth of Staphylococcus aureus cells were investigated using turbidimetric measurements and visualized using scanning electron microscopy. Analyses of the chemical composition of the oils were done using gas chromatography and gas chromatography/mass spectrometry. RESULTS AND DISCUSSION: Both the essential oil and the decocts exhibited a very high antimicrobial activity against all tested strains, with S. aureus as the most sensitive one [e.g., for the oil sample the values for minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) were 0.02, 0.04 µL/mL, respectively]. Growth curves of S. aureus demonstrated a significant decrease in turbidity (for the MIC concentration this amounted to ca. 70%) showing a concentration-dependent lysis of the cells, confirmed by scanning electron microscopy. Chemical composition, anatomical and morphological features of the sample pointed to Carlina acanthifolia L. (Asteraceae) instead of Carlina acaulis L. (Asteraceae). CONCLUSION: The results showed significant antimicrobial effect of the essential oil and the decoctions and support the use of this plant in ethnomedicine for the treatment of various human infections, especially those caused by S. aureus. Adulteration of the drug would not cause significant differences in its biological activity, since chemical composition of the sample showed high similarity with those containing C. acaulis roots.

Volatiles of Curcuma mangga Val. & Zijp (Zingiberaceae) from Malaysia.

Analysis by GC and GC/MS of the essential oil obtained from Malaysian Curcuma mangga Val. & Zijp (Zingiberaceae) rhizomes allowed the identification of 97 constituents, comprising 89.5% of the total oil composition. The major compounds were identified as myrcene (1; 46.5%) and ß-pinene (2; 14.6%). The chemical composition of this and additional 13 oils obtained from selected Curcuma L. taxa were compared using multivariate statistical analyses (agglomerative hierarchical cluster analysis and principal component analysis). The results of the statistical analyses of this particular data set pointed out that 1 could be potentially used as a valuable infrageneric chemotaxonomical marker for C. mangga. Moreover, it seems that C. mangga, C. xanthorrhiza Roxb., and C. longa L. are, with respect to the volatile secondary metabolites, closely related. In addition, comparison of the essential oil profiles revealed a potential influence of the environmental (geographical) factors, alongside with the genetic ones, on the production of volatile secondary metabolites in Curcuma taxa.

Plant volatiles providing additional evidences to the occurence of a wild-growing population of Calamintha vardarensis (Greuter et Burdet) Silic outside of its natural habitat.

The essential-oil profile of a Calamintha species, wild-growing in the urban settings of the city of Nis (South Serbia) and botanically tentatively identified as C. vardarensis (endemic species native to FYR Macedonia and East Serbia), has been statistically (multivariate statistical analyses) compared with those of other Calamintha species, including two previously investigated C. vardarensis populations, as a means of corroboration of the surprising occurence of this Calamintha population outside of its natural distributional range. Agglomerative hierarchical clustering reveals a close link of C. vardarensis from Nis (with neo-menthol (40.0%), menthone (21.8%), and pulegone (27.2%) as its major oil contributors) and C. vardarensis from FYR Macedonia.

Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae).

The first GC and GC/MS analyses of the essential oils hydrodistilled from dry leaves of Arctostaphylos uva-ursi and Vaccinium vitis-idaea enabled the identification of 338 components in total (90.4 and 91.7% of the total GC peak areas, respectively). Terpenoids, fatty acids, fatty acid- and carotenoid derived compounds were predominant in the two samples. Both oils were characterized by high relative percentages of α-terpineol and linalool (4.7-17.0%). Compositional data on the volatiles of the presently analyzed and some other Ericaceae taxa (literature data) were mutually compared by means of multivariate statistical analyses (agglomerative hierarchical cluster analysis and principal component analysis). This was done in order to determine, based on the essential oil profiles, possible mutual relationships of the taxa within the family, especially that of species from the genera Arctostaphylos and Vaccinium. Results of the chemical and statistical analyses pointed to a strong relation between the genera Vaccinium and Arctostaphylos.

Combination of Selective PARP3 and PARP16 Inhibitory Analogues of Latonduine A Corrects F508del-CFTR Trafficking.

The marine natural product latonduine A (1) shows F508del-cystic fibrosis transmembrane regulator (CFTR) corrector activity in cell-based assays. Pull-down experiments, enzyme inhibition assays, and siRNA knockdown experiments suggest that the F508del-CFTR corrector activities of latonduine A and a synthetic analogue MCG315 (4) result from simultaneous inhibition of PARP3 and PARP16. A library of synthetic latonduine A analogs has been prepared in an attempt to separate the PARP3 and PARP16 inhibitory properties of latonduine A with the goal of discovering selective small-molecule PARP3 and PARP16 inhibitory cell biology tools that could confirm the proposed dual-target F508del-CFTR corrector mechanism of action. The structure activity relationship (SAR) study reported herein has resulted in the discovery of the modestly potent (IC50 3.1 µM) PARP3 selective inhibitor (±)-5-hydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one (5) that shows 96-fold greater potency for inhibition of PARP3 compared with its inhibition of PARP16 in vitro and the potent (IC50 0.362 µM) PARP16 selective inhibitor (±)-7,8-dichloro-5-hydroxy-4-(pyridin-2-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one (6) that shows 205-fold selectivity for PARP16 compared with PARP3 in vitro. At 1 or 10 µM, neither 5 or 6 alone showed F508del-CFTR corrector activity, but when added together at 1 or 10 µM each, the combination exhibited F508del-CFTR corrector activity identical to 1 or 10 µM latonduine A (1), respectively, supporting its novel dual PARP target mechanism of action. Latonduine A (1) showed additive in vitro corrector activity in combination with the clinically approved corrector VX809, making it a potential new partner for cystic fibrosis combination drug therapies.

Chemical composition of the essential oils of serbian wild-growing Artemisia absinthium and Artemisia vulgaris.

The chemical composition of the aerial and root essential oils, hydrodistilled from Artemisia absinthium L. and Artemisia vulgaris L. (wild-growing populations from Serbia), were studied by gas chromatography, gas chromatography-mass spectrometry, and 13C nuclear magnetic resonance. During the storage of plant material under controlled conditions, a significant decrease of essential oil yields (isolated directly after drying and after 1 year of storage) and significant differences in their chemical compositions were observed. A possible mechanism for the observed oil component interconversion has been discussed. The noticeable differences in the chemical composition of the oils isolated from roots and aerial parts of A. absinthium and A. vulgaris were also correlated with the diverging biosynthetic pathways of volatiles in the respective plant organs. The antimicrobial activities against the common human pathogens of all of the isolated oils were tested according to National Committee on Clinical Laboratory Standards. The oils showed a broad spectrum of antimicrobial activity against the tested strains. Therefore, these oils can be used as flavor and fragrance ingredients.

New volatile sulfur-containing compounds from wild garlic (Allium ursinum L., Liliaceae).

In many countries, the leaves of Allium ursinum L. (Liliaceae) are a popular substitute for garlic and, for centuries, the herb has been taken internally to treat an array of medical conditions. Herein, we report the chemical composition of 12 different A. ursinum essential-oil samples (five populations; fresh/air-/oven-dried plant material; leaves/inflorescences). GC-MS/GC-FID analyses, quantitative structure-property relationship modeling (simple 0D/1D-descriptors) of retention indices and the synthesis of selected compounds, enabled the identification of >200 different constituents, mainly organo(poly)sulfides. Some of these were new compounds (allyl (methylthio)methyl, (methylthio)methyl (Z)/(E)-1-propenyl and allyl 1-(methylthio)propyl disulfides) or were previously not detected in samples of natural origin (heptyl methyl, methyl octyl, allyl hexyl (1), allyl octyl (2) and propyl (propylthio)methyl sulfides). A multivariate statistical analysis revealed the onset of significant changes in the plant material volatile profile during the drying process.

Toxic essential oils. Part IV: The essential oil of Achillea falcata L. as a source of biologically/pharmacologically active trans-sabinyl esters.

Herein we report on the comprehensive chemical analysis of the essential oils obtained from above- and underground parts of a previously unreported chemotype of Achillea falcata L. (Asteraceae) and, for the first time, on the biological/toxicological profile of its dominant/newly discovered volatile metabolites. Detailed spectral analyses, in combination with chemical synthesis and theoretical study, of selected constituents, enabled the identification of trans-sabinol and its esters - the formate, tiglate (new compounds), acetate, butanoate, isobutanoate, 2-methylbutanoate and 3-methylbutanoate - in both aerial and underground parts of A. falcata. Evaluation of acute toxicity in Artemia salina model, in vitro and in silico (molecular docking) evaluation of acetylcholinesterase inhibitory activity and in vivo (mice) evaluation of antinociceptive activity (hot plate, tail immersion and acetylcholine-induced abdominal writhing tests) of trans-sabinol and its esters suggested that they may interact with different targets in crustacean/mammalian organisms. Alongside moderate acute toxicity (LD50 (48 h) = 0.03-0.26 mmol/L), the tested compounds exert influence on both the peripheral and central nervous systems (in the hot plate test, trans-sabinyl tiglate, at 50 mg/kg, produced a 140% baseline increase 15 min after the treatment) and to moderately inhibit acetylcholinesterase (at the concentration of 20 µg/mL, these compounds caused a reduction of acetylcholinesterase activity up to 40%).