Search Results (21)

Camphora officinarum (syn. Cinnamomum camphora) is an ecologically, medicinally, and economically important tree species widely known for its essential oils (EOs), timber, and long history of use in traditional medicine. In recent years, renewed interest in this species has been driven by taxonomic revision, the discovery of chemically distinct chemotypes, and advances in genomics, metabolomics, and biotechnological processing. This review summarizes current knowledge on the botany, distribution, phytochemistry, biological properties, agro-industrial value, and biotechnological potential of C. officinarum. Particular attention is given to the genetic and metabolic basis of terpene diversity, especially the role of terpene synthase (TPS) gene expansion in the formation of camphor-, linalool-, borneol-, cineole-, and citral-type profiles. We also discuss developments in essential oil extraction, the utilization of non-volatile constituents such as flavonoids and lignans, and the nutritional value of seed kernel oil rich in medium-chain fatty acids (MCFAs). In addition, recent progress in tissue culture, multi-omics analysis, metabolic engineering, and nano-enabled delivery systems is reviewed. The paper also considers important safety and ecological issues, including the dose-dependent toxicity of camphor and the contrasting status of the species as a protected native resource in East Asia and an invasive plant in some introduced regions. Overall, this review provides an updated and balanced overview of C. officinarum, identifies key knowledge gaps, and highlights future prospects for sustainable utilization, conservation of native genetic resources, and exploitative control of invasive populations. Full article

Juniperus communis is the juniper with the widest geographical distribution, owing to its high ecological valence. Nevertheless, there is only a limited number of studies of its phenotypic and molecular variability. In this study, we coupled leaf essential oil (EO) composition with molecular and environmental data to better understand this species’ distribution and variability in the central Balkans. EOs were obtained by simultaneous hydrodistillation and extraction, and analysed using GC coupled with MS and FID detectors. For molecular analysis, inter-simple sequence repeats (ISSR) using five primers were analysed. Three chemotypes were most abundant in the study area: sabinene, an intermediate chemotype, and α-pinene. Several additional chemotypes were also identified. In total, 118 compounds present above 0.05% were detected and identified. Monoterpene hydrocarbons dominated the EO composition (43.8–79.1%). Multivariate analyses showed separation of populations from north to south. ISSRs yielded 78 polymorphic bands. Three genetic pools could also be identified that roughly correspond to this distribution, though data is not completely congruent with chemophenetic. Results indicate high genetic diversity, with high gene flow between populations, but also certain differentiation of populations. Full article

Background/Objectives: Propolis is a complex bee product with a composition that varies according to local vegetation, environmental conditions, and bee foraging behaviours. Recently, gas chromatography–mass spectrometry (GC–MS) has been employed in Uganda to analyse its volatile components. This study examined Ugandan propolis non-volatile metabolites to determine chemotypes and identify antibacterial compounds. Methods: Ethanolic extracts were analysed using liquid chromatography–high-resolution quadrupole time-of-flight mass spectrometry (LC-HR-QTOF-MS) in an untargeted MS/MS mode. Data processing was carried out using MZmine, then annotated with Global Natural Products Social Molecular Networking (GNPS) and SIRIUS. Chemometric methods assisted in identifying regional chemical signatures. Metabolites highlighted by the heatmap were evaluated for antibacterial activity using molecular docking against bacterial targets, followed by ADMET (absorption, distribution, metabolism, excretion, and toxicity) assessments. Results: Out of 3252 features, 234 and 52 putative compounds were annotated in GNPS and SIRIUS, respectively, as indicated by molecular networking, suggesting high chemical complexity. The chemical space mainly comprises flavonoids (including glycosides, aglycones, methylated, and prenylated derivatives), phenolic acids, amides, hydroxycinnamate derivatives, lignans, megastigmanes, and various diterpenoid skeletons. Multivariate analyses clearly distinguish geographical chemotypes, separating flavonoid-rich regions from diterpenoid-rich regions. Docking studies revealed flavonoids, diterpenoids, and lignans with strong predicted antibacterial activities and favourable ADMET profiles. Conclusions: This study provides the first LC–MS characterisation of the non-volatile metabolome of Ugandan propolis, thereby expanding its chemical diversity. Metabolomics and computational approaches lay a foundation for future ecological, chemotaxonomic, and pharmacological research. Full article

Cyanobacterial blooms are an escalating ecological concern driven by eutrophication and climate warming. Bloom-forming cyanobacteria can produce a broad spectrum of bioactive secondary metabolites. Among these, microcystins (MCs) are the most recognised hepatotoxins; however, natural populations of Planktothrix agardhii also synthesise numerous non-ribosomal peptides (NRPs) with poorly understood ecological roles and combined toxic effects. This review demonstrated the role of mixtures of P. agardhii cyanometabolites (oligopeptides and biogenic compounds) in cyanobacterial proliferation, emphasising the rapid evolution of chemotypes. The role of P. agardhii oligopeptides other than MCs in the cyanobacterial toxicity to duckweeds is also discussed. Laboratory experiments indicated that crude extracts containing complex peptide mixtures may inhibit Spirodela polyrhiza growth more strongly than pure MC-LR, suggesting synergistic effects within natural metabolite assemblages. Particular attention is given to variant-specific degradation pathways of MCs within duckweed-associated microbiota. By integrating biochemical, ecological, and microbiological perspectives, this synthesis outlines emerging directions in the study of mixtures of cyanobacterial peptides and other compounds, microbial degraders, and macrophyte-associated bioremediation strategies aimed at mitigating cyanotoxin risks in aquatic environments. Full article

Forsythia suspensa (Thunb.) Vahl, a pharmacopoeial medicinal plant, is valued for its therapeutic efficacy in heat-clearing detoxification, dispelling wind-heat, and promoting blood circulation to resolve stasis. Flavonoids, ubiquitous secondary metabolites in F. suspensa, are critically linked to pharmacological activities and exhibit diverse biological functions. To elucidate the chemotypic divergence and ecological drivers of its bioactive compounds, we conducted flavonoid metabolomic profiling across ten wild populations F. suspensa using UPLC-MS/MS. Results revealed significant inter-population variation in all twenty-nine flavonoid metabolites analyzed. Notably, Notably, Cinchonain Ic was significantly enriched in the JX population, Flavanomarein in the LT population, and Desmethylxanthohumol in the HX population. Association analysis with environmental variables further indicated that Sulfuretin, Apigenin-5-O-glucoside, and Flavanomarein were positively correlated with multiple precipitation-related variables (bio12-Annual Precipitation, bio14-Precipitation of Driest Month, bio17-Precipitation of Driest Month, and bio19-Precipitation of Coldest Quarter), whereas Vicenin 2 was negatively correlated with bio12, bio17, and bio19. Homoplantaginin showed a positive correlation with bio4 (Temperature Seasonality) and bio7 (Temperature Annual Range). Loureirin B was positively correlated with elevation but negatively correlated with high-temperature variables (bio5-Max Temperature of Warmest Month, bio8-Mean Temperature of Wettest Quarter, and bio10-Mean Temperature of Warmest Quarter). 5-Demethoxynobiletin was positively associated with both precipitation (bio12, bio17, bio19) and temperature variables (bio1-Annual Mean Temperature, bio6-Min Temperature of Coldest Month, bio9-Mean Temperature of Driest Quarter and bio11-Mean Temperature of Coldest Quarter). Cinchonain Ic was positively correlated with bio2 (Mean Monthly Temperature Range), and Oroxin A was negatively correlated with elevation. These findings demonstrated that flavonoids accumulation in F. suspensa was predominantly influenced by temperature heterogeneity, with precipitation serving as a secondary factor, while latitude and elevation play only limited roles. This study systematically investigates the divergence and environmental drivers of flavonoids in F. suspensa populations, clarifies the molecular ecological basis of its adaptation to environmental heterogeneity, and provides valuable insights for leveraging ecological factors to enhance medicinal potential, ultimately supporting targeted breeding and optimized field management strategies. Full article

Patterns of plant phytochemical composition vary between populations of any plant species and impact the cultural and economic value of important plant species. Phenotypic outcomes are a combination of genetic, environmental, and human influence. Thymus saturejoides is endemic to Morocco and Algeria and part of a suite of economically important wild plants used to produce essential oils for the global market in the region. Currently, little is known about the human and ecological factors that shape T. saturejoides phenotypic traits. In this paper, we examine the factors that drive phenotypic variation in the species T. saturejoides through the chemical composition of essential oil. We used a systematic review protocol to identify 15 published sources, from which we obtained data on chemical composition (secondary metabolites and/or chemotype) for 51 samples, as well as information on the geographic location of harvest listed in the paper. We used the geographic location information to determine elevation, temperature, precipitation, soil type, and soil carbon. We ran linear regression models to determine if any of these environmental variables were associated with the content of key chemicals known to mark quality and value in T. saturejoides. Elevation was statistically significant in the models for thymol, linalool, p-cymene, carvacrol (p = 0.072), and borneol (p = 0.056). Other environmental variables were not statistically significantly related to the content of any of the chemicals. Although we did not find an association between chemical composition and temperature or precipitation, this does not exclude the possibility that a relationship exists at a finer spatial or temporal scale, such as days, weeks, or months. Our findings could also suggest that genetic and human-related factors, such as time of harvest, are more important than environmental factors. Full article

Abies alba Mill. (Pinaceae), silver fir, is a widespread gymnosperm species in Europe, important for its ecological, economic, social, and cultural significance, as well as for its use for food and bioremediation purposes. The various parts of the plant (leaves, branches, cones, wood, bark) are also of pharmaceutical interest due to their composition of active compounds. In the last three decades, an impressive amount of research has been dedicated to this species. The variability of the chemical composition of essential oils (whether they come from leaves, oleoresin from branches, or other parts of the plant) is impressive, even in the case of specimens collected from the same geographical area. For essential oils prepared from needles or twigs and branches, limonene, β-pinene, α-pinene, camphene, β-phellandrene, and bornyl acetate are the leading compounds, although their wide variations seem to correspond to multiple chemotypes. Both bark and wood are rich in lignans and phenolic compounds. Matairesinol is apparently the dominant lignan in bark, and secoisolariciresinol and lariciresinol are the dominant ones in wood samples. Pharmacological studies with promising results have evaluated the antioxidant effect (mainly due to essential oils), but also the antimicrobial, antitumor, probiotic, antidiabetic, anti-steatosis, and anti-psoriatic activities. Full article

Artemisia annua L. is distributed throughout the world and it is an important medicinal plant in Korea to treat various human diseases. Recently, A. annua has also been considered to be an effective ethnobotanical drug against COVID-19. A. annua contains an appreciable amount of essential oil with different biological properties. However, the composition of essential oils in aromatic plants can be varied depending on several factors, including geographic, genetic, ecological, etc. Hence, the present study aimed to investigate the chemical diversity of essential oils of Korean A. annua collected from different locations in Korea by multivariate analysis. For this purpose, the seeds of A. annua were collected from 112 different locations in Korea and were grown under the same environmental conditions. Except for nine individuals which decayed during the cultivation, essential oils were isolated from the aerial parts of 103 A. annua individuals (AEOs) using the steam distillation extraction method, and their chemical compositions were determined by GC-MS analysis. Furthermore, a multivariate analysis was performed to distinguish the difference between 103 individuals of A. annua based on their essential oil compositions. The yield of A. annua essential oils ranged from 0.04 to 1.09% (v/w). Based on the GC-MS data, A. annua individuals were grouped into six chemotypes such as artemisia ketone, camphor, β-cubebene, eucalyptol, α-pinene, and β-selinene. The multivariate analysis results revealed that Korean A. annua could be largely grouped into three clusters such as artemisia ketone, eucalyptol, and β-selinene. Among 35 components selected for principal component analysis (PCA), PC1, PC2, and PC3 accounted for 82.55%, 8.74%, and 3.62%, respectively. Although all individuals of A. annua were cultivated under the same environmental conditions, there is an intraspecific chemical diversity that exists within Korean native species. Full article

Thymus holosericeus Čelak. (Lamiaceae) is a taxonomically isolated and endangered local endemic thyme species which is geographically isolated in four Ionian Islands (West Greece). The present study investigated the essential oil (EO) composition, the ecological preferences, and their correlations in three T. holosericeus wild-growing populations from Zakynthos (ΤH-Z), Cephalonia (ΤH-C) and Lefkada (ΤH-L). The variations in essential oil yield and the composition of T. holosericeus populations were evaluated using hydrodistillation, GC/MS, TLC and NMR analysis. The climatic conditions of each sample were organized and analyzed in RStudio with the raster package and in SPSS with Pearson’s Canonical Correlation Analysis (CCA), respectively. The aerial parts of the plants varied in EO yields from 1.92 to 2.28% w/v. The analysis of EO constituents revealed noteworthy qualitative and quantitative inter-population variation. The composition of EOs revealed the presence of linalool (82.77%) and borneol (5.95%) as major compounds in ΤH-Z, while carvacrol (35.34%), geraniol (23.98%), linalool (14.37%), borneol (5.66%), thymol (4.27%) and p-cymene (4.08%) were the main compounds in ΤH-C and linalool (40.37%), geraniol (39.42%) and borneol (5.20%) were dominant components in ΤH-L. The results of the gas chromatography procedure have also been confirmed by ¹H and ¹³C-NMR and TLC analysis. The ecological profile showed an average annual precipitation of 942 ± 18.33 mm and the temperature limits in which T. holosericeus seems to adapt to are 6.80± 1.08 °C 27.70 ± 0.70 °C. Regarding the examined samples, TH-C was adapted to the driest summer and coldest winter conditions, TH-Z was adapted to the lowest annual precipitation with the most complex climatic conditions, and TH-L was adapted to the highest summer temperatures with the lowest precipitation in the wettest period of the year. For each sampled population, the CCA identified the association of the samples’ EOs composition with the prevailing local environmental conditions. Full article

Our previous research has proven that the immortelle (Helichrysum italicum) essential oil (EO) grown in Serbia possesses respectable biological potential and desirable composition of volatile compounds with the potential for a wide range of applications in the food, cosmetics, and pharmaceutical industries. Within this study, the impact of seasonal variations (temperature, precipitation, and insolation) during three successive years (2017, 2018, and 2019), on the volatile profile of γ-curcumene + ar-curcumene immortelle chemotype was determined. Steam distillation was utilized to extract EO from the plant material, followed by chromatographic mass spectrometric analysis revealing 50 volatile compounds. A multiple linear regression model was developed, and principal component analyses were conducted to deliver detailed information regarding the prediction, component profile, and parallel contents of active compounds of the immortelle EO. Under Serbian agro-ecological conditions, with appropriate harvest method, immortelle can achieve two harvests per year: the first in July, and the second in August. The γ-curcumene + ar-curcumene chemotype usually occurs as the dominant chemotype in the region of the ex-Yugoslavia countries. This chemotype probably developed as an adaptation to climatic conditions, and spring and summer precipitation positively influenced curcumene accumulation in plants. Such a phenomenon was especially noticeable in the first harvest. Full article

Microbe–invertebrate associations, commonly occurring in nature, play a fundamental role in the life of symbionts, even in hostile habitats, assuming a key importance for both ecological and evolutionary studies and relevance in biotechnology. Extreme environments have emerged as a new frontier in natural product chemistry in the search for novel chemotypes of microbial origin with significant biological activities. However, to date, the main focus has been microbes from sediment and seawater, whereas those associated with biota have received significantly less attention. This review has been therefore conceived to summarize the main information on invertebrate–bacteria associations that are established in extreme marine environments. After a brief overview of currently known extreme marine environments and their main characteristics, a report on the associations between extremophilic microorganisms and macrobenthic organisms in such hostile habitats is provided. The second part of the review deals with biotechnologically relevant bioactive molecules involved in establishing and maintaining symbiotic associations. Full article

Cuckoo wasps (Chrysididae, Hymenoptera) are known for their parasitoid or cleptoparasitic life histories. Indeed, the biology of only a few species has been studied in detail and often only little more is known than the host species. By mimicking their hosts’ cuticular hydrocarbon (CHC) profiles, species that parasitize single (or a few closely related) host species manage to deceive their hosts. However, the variability of the CHC profile in generalist cuckoo-wasp species is still unknown. Here, we used gas chromatography—mass spectrometry (GC-MS) and DNA barcoding to study intraspecific variation in cuticular hydrocarbons of one less host-specific species of cuckoo wasps, Trichrysis cyanea. Cuticular hydrocarbon (CHC) patterns were found to differ between males and females. Additionally, we found chemical polymorphism among females, which formed three distinct chemical subgroups characterized by different alkene patterns. A lack of divergence in the DNA barcoding region suggests that these different chemotypes do not represent cryptic species. Whether this intrasexual CHC-profile variation is an adaptation (mimicry) to different host species, or simply signaling the reproductive status, remains unclear. Full article

The aromatic species Piper gaudichaudianum Kunth (Piperaceae) is widely used in Brazil for medicinal and ritualistic applications. In the current study, chemophenetic patterns were realized across season and circadian rhythm based on the chemical profile of essential oils (EOs) from leaves. Hydrodistilled essential oils were analyzed by GC-MS and GC-FID, and a new calculation of metabolite oxidation level, averaged for each individual molecule component of the EO, was used to explore the patterns of metabolism/biosynthesis. This new index used an intermediate calculation, the ‘weighted average redox standard’ (S_RO), to enable a value for mixtures of metabolites to be generated, the ‘general mixture redox index’ (GM_OR). The indices were subjected to a proof-of-concept approach by making comparison to outcomes from multivariate analyses, i.e., PCA and HCA. Chemical analysis demonstrated that the essential oils were dominated by sesquiterpenes, constructed of 15 classes of compound (C-skeletons), and 4 C-skeletons were recognized in the monoterpene group, giving a total of 19. The variation of chemical profiles was distinct at different phenological stages, but stronger chemical variation was evident between day and night as compared to season. Furthermore, due to comprehensive sampling across different regions, nine chemotypes were recognized, including those previously reported. The S_RO and GM_RO indices demonstrate that phenological variation of chemistry is mainly an outcome of redox fluctuations in terpene biosynthesis, changing from day to night. These indices also corroborate that chemical diversity is increased with oxidative metabolism. Lastly, the current study demonstrates pronounced phenotypic plasticity in P. gaudichaudianum, which makes it a suitable candidate to help further our understanding of chemophenetics and chemical ecology. Full article

This study evaluated the effects of ecology (plant community, topography and pedology), as well as of climate, on the composition of essential oils (EOs) from two officinal wild plant species (Lamiales) from Apulia, namely Satureja cuneifolia Ten. and Thymus spinulosus Ten. Few scientific data on their chemical composition are available, due to the fact that the first has a limited distribution range and the second is endemic of southern Italy. Results for both species, never officially used in traditional medicine and/or as spices, showed that the ecological context (from a phytosociological and ecological point of view) may influence their EO composition, and hence, yield chemotypes different from those reported in the literature. S. cuneifolia and Th. spinulosus can be considered good sources of phytochemicals as natural agents in organic agriculture due to the presence of thymol and α-pinene. Overall, the obtained trend for EOs suggests a potential use of both species as food, pharmacy, cosmetics and perfumery. Hence, their cultivation and use represent a positive step to reduce the use of synthetic chemicals and to meet the increasing demand for natural and healthier products. Full article

Marrubium vulgare is a cosmopolitan medicinal plant from the Lamiaceae family, which produces structurally highly diverse groups of secondary metabolites. A total of 160 compounds were determined in the volatiles from Serbia during two investigated years (2019 and 2020). The main components were E-caryophyllene, followed by germacrene D, α-humulene and α-copaene. All these compounds are from sesquiterpene hydrocarbons class which was dominant in both investigated years. This variation in volatiles composition could be a consequence of weather conditions, as in the case of other aromatic plants. According to the unrooted cluster tree with 37 samples of Marrubium sp. volatiles from literature and average values from this study, it could be said that there are several chemotypes: E-caryophyllene, β-bisabolene, α-pinene, β-farnesene, E-caryophyllene + caryophyllene oxide chemotype, and diverse (unclassified) chemotypes. However, occurring polymorphism could be consequence of adaptation to grow in different environment, especially ecological conditions such as humidity, temperature and altitude, as well as hybridization strongly affected the chemotypes. In addition, this paper aimed to obtain validated models for prediction of retention indices (RIs) of compounds isolated from M. vulgare volatiles. A total of 160 experimentally obtained RIs of volatile compounds was used to build the prediction models. The coefficients of determination were 0.956 and 0.964, demonstrating that these models could be used for predicting RIs, due to low prediction error and high r². Full article