Group Of Sesquiterpenes Research Articles

The Content of Volatile Organic Compounds in Calypogeia suecica (Calypogeiaceae, Marchantiophyta) Confirms Genetic Differentiation of This Liverwort Species into Two Groups.

Calypogeia is a genus of liverworts in the family Calypogeiaceae. The subject of this study was Calypogeia suecica. Samples of the liverwort Calypogeia suecica were collected from various places in southern Poland. A total of 25 samples were collected in 2021, and 25 samples were collected in 2022. Volatile organic compounds (VOCs) from liverworts were analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 107 compounds were detected, of which 38 compounds were identified. The identified compounds were dominated by compounds from the sesquiterpene group (up to 34.77%) and sesquiterpenoids (up to 48.24%). The tested samples of Calypogeia suecica also contained compounds belonging the aromatic classification (up to 5.46%), aliphatic hydrocarbons (up to 1.66%), and small amounts of monoterpenes (up to 0.17%) and monoterpenoids (up to 0.30%). Due to the observed differences in the composition of VOCs, the tested plant material was divided into two groups, in accordance with genetic diversity.

Exogenous methyl jasmonate (MeJA) altered phytochemical composition and enhanced the expression of PatAACT gene of in vitro culture-derived patchouli var. Sidikalang (Pogostemon cablin Benth.)

The demand for economically valuable terpenoid-derived compounds, especially those extracted from patchouli plants, is experiencing exponential growth. These compounds are potentially applied in a wide range of industrial sectors including food manufacturing, perfumeries, and pharmaceuticals. Nevertheless, there is a need for further development in patchouli plant cultivation to align with market demands. Therefore, employing robust in vitro-based propagation methods could offer significant advantages. Furthermore, this technique is also used for plant metabolites enhancement. This strategy applies the methyl jasmonate (MeJA) elicitor to boost the production of secondary metabolites. In Indonesia, patchouli var. Sidikalang is extensively cultivated in many areas. This study aims to evaluate the effect of naphtaleneacetic acid (NAA) and 6-benzylamino purine (BAP) to increase plant growth via in vitro culture. Furthermore, we also investigate the effect of MeJA on the metabolite profiles and on the AACT gene expression. Our findings revealed that the combination of 2.5 µM of BAP and 0.25 µM of NAA resulted in optimal growth and high rate of organogenesis across all growth parameters. Our data also successfully identified 50 dominant compounds, each with varying percentage areas. Notably, patchouli alcohol emerged as the primary compound in the tricyclic sesquiterpene group, consistently present in all treatment groups. Furthermore, the expression of the PatAACT gene significantly increased by 7.42-fold after treatment with MeJA at 100 µM and by 2,9-fold after treatment with MeJA at 300 µM, compared to the control. Altogether, our findings might offer new insight in P. cablin propagation and new strategy for patchouli-derived metabolites using exogenous MeJA.

HS-SPME-GC-MS and Chemometrics for the Quality Control and Clustering of Monovarietal Extra Virgin Olive Oil: A 3-Year Study on Terpenes and Pentene Dimers of Italian Cultivars.

Terpenes and pentene dimers are less studied volatile organic compounds (VOCs) but are associated with specific features of extra virgin olive oils (EVOOs). This study aimed to analyze mono- and sesquiterpenes and pentene dimers of Italian monovarietal EVOOs over 3 years (14 cultivars, 225 samples). A head space-solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) method recently validated was used for terpene and pentene dimer quantitation. The quantitative data collected were used for both the characterization and clustering of the cultivars. Sesquiterpenes were the molecules that most characterized the different cultivars, ranging from 3.908 to 38.215 mg/kg; different groups of cultivars were characterized by different groups of sesquiterpenes. Pentene dimers (1.336 and 3.860 mg/kg) and monoterpenes (0.430 and 1.794 mg/kg) showed much lower contents and variability among cultivars. The application of Kruskal-Wallis test-PCA-LDA-HCA to the experimental data allowed defining 4 clusters of cultivars and building a predictive model to classify the samples (94.3% correct classification). The model was further tested on 33 EVOOs, correctly classifying 91% of them.

Seasonal Variability of Volatile Components in Calypogeia integristipula.

Liverworts contain a large number of biologically active compounds that are synthesised and stored in their oil bodies. However, knowledge about the chemical composition of individual species is still incomplete. The subject of the study was Calypogeia integristipula, a species representing leafy liverworts. Plant material for chemotaxonomic studies was collected from various locations in Poland. The chemical composition was determined in 74 samples collected from the natural environment in 2021 and 2022 in three growing seasons: spring, summer and autumn, and for comparison with samples originating from in vitro culture. The plants were classified as Calypogeia integristipula on the basis of morphological characteristics, oil bodies, and DNA markers. The volatile organic compounds (VOCs) from the biological material were extracted by headspace solid phase microextraction (HS-SPME). The samples were then analysed by gas chromatography-mass spectrometry (GC-MS). A total of 79 compounds were detected, of which 44 compounds were identified. The remaining compounds were described using the MS fragmentation spectrum. Cyclical changes in the composition of compounds associated with the growing season of Calypogeia integristipula were observed. Moreover, samples from in vitro culture and samples taken from the natural environment were shown to differ in the composition of chemical compounds. In terms of quantity, among the volatile compounds, compounds belonging to the sesquiterpene group (46.54-71.19%) and sesqiuterpenoid (8.12-22.11%) dominate. A smaller number of compounds belong to aromatic compounds (2.30-10.96%), monoterpenes (0.01-0.07%), monoterpenoids (0.02-0.33%), and aliphatic hydrocarbons (1.11-6.12%). The dominant compounds in the analysed liverworts were: anastreptene (15.27-31.14%); bicyclogermacrene (6.99-18.09%), 4,5,9,10-dehydro-isolongifolene (2.00-8.72%), palustrol (4.95-9.94%), spathulenol (0.44-5.11%).

Comparative study of the chemical composition and anti-proliferative activities of the aerial parts and roots of Apium graveolens L. (celery) and their biogenic nanoparticles

• The aerial parts and roots of celery showed potent antiproliferative effects against human tumor cells. • The secondary metabolites of both organs were explored by HPLC‒HESI‒HRMS metabolomics. • Potent cytotoxic nanoparticles were green synthesized from the extracts of both celery parts. • Molecular docking of the identified metabolites revealed their possible inhibition of GAK. • Celery and its biogenic nanoparticles are therefore relevant sources to functional food and drug development. Apiaceae plants are multipurpose folk remedies and bioactive foods that show a remarkable ability to biosynthesize a large number of secondary metabolites with antitumor and chemopreventive potential. Among the various members of the Apiaceae, celery ( Apium graveolens L.) has long been used as a popular edible and medicinal plant owing to its plentiful health benefits and nutraceutical properties; however, the anticancer potential of this important species has been seldom studied, mostly focusing on its seeds. Therefore, this work was designed to delve into the chemical composition and anti-proliferative potential of the total ethanolic extracts of the aerial parts (TEEAGA) and roots (TEEAGR) of A. graveolens var. dulce (Mill.) Pers. as well as their green synthesized silver nanoparticles (AgNPs). In general, both TEEAGA and TEEAGR exhibited moderate to potent inhibitory activities against human liver (HepG-2), colon (Caco-2), and breast (MCF-7) cancer cell lines, with interesting IC 50 profiles [(41.37 ± 0.12, 27.65 ± 0.27, and 9.48 ± 0.04 μg/mL) and (11.58 ± 0.02, 7.13 ± 0.03, and 6.58 ± 0.02 μg/mL), respectively] as compared with doxorubicin, while more pronounced anti-proliferative effects were observed for their biogenic AgNPs, which showed IC 50 values ranging between 25.41 ± 0.16 and 1.37 ± 0.03 μg/mL. Moreover, HPLC‒HESI‒HRMS-based metabolomics analysis of both extracts showed the presence of a varied group of secondary metabolites, including flavonoids, phenylpropanoids, phthalides, coumarins, and sesquiterpenes that further displayed moderate to promising binding affinities to the active site of cyclin G-associated kinase (GAK), particularly graveobioside A, graveobioside B, and celeroside C, suggesting their possible contribution as GAK modulators to the anti-proliferative potential of celery. These findings can help broaden future research on the utilization of different parts of celery and their NPs as functional foods and medicines in cancer chemoprevention and therapy.

Chemical compositions of Sideritis albiflora Hub. – Mor.

Background and Aims: Sideritis species (Lamiaceae) which are quite widespread in the Mediterranean region and represented by 46 species and 53 taxa in Turkey, are often used as a antirheumatic, anti-inflammatory, antimicrobial and diuretic remedies. Methods: In this study, the infusion (INF), essential oil (EO) and methanolic extract (ME) of chemical compounds prepared from aerial parts of Sideritis albiflora Hub.-Mor. (endemic) were investigated. Results: The presence of chlorogenic acid, verbascoside, forsythoside, apigenin glucoside, and isoscutellarein derivatives in the infusion and methanol extract of the plant was determined by LC-MS / MS analysis. In addition, the main constituents of the essential oil were found as germacrene D (23.5%), ß-caryophyllene (13.6%) and caryophylene oxide (8.0%) by GC / MS and GC / FID simultaneously. Conclusion: In this study, the essential oil, the methanolic extract and the infusion of S. albiflora species were prepared and their chemical compositions elucidated. It was determined that the essential oil chemical compound composition is rich in terms of the sesquiterpene group. Infusions of aerial parts of some Sideritis species have traditionally been used in the treatment of many diseases. Accordingly, the fact that the phenolic compounds of S. albiflora infusion have not been studied before increases the importance of this study. In addition, the therapeutic effect was shown to be related to major S. albiflora compounds, and the correlation between in vitro activity and ethnobotanical use was evaluated. The effective phenolic compounds contained in S. albiflora are thought to support the traditional uses of the plant.

Epidermis-Specific Metabolic Engineering of Sesquiterpene Formation in Tomato Affects the Performance of Potato Aphid Macrosiphum euphorbiae

Tomato produces a number of terpenes in their glandular trichomes that contribute to host plant resistance against pests. While glandular trichomes of cultivated tomato Solanum lycopersicum primarily accumulate a blend of monoterpenes, those of the wild tomato species Solanum habrochaites produce various sesquiterpenes. Recently, we have identified two groups of sesquiterpenes in S. habrochaites accessions that negatively affect the performance and choice behavior of the potato aphid (Macrosiphum euphorbiae). Aphids are piercing-sucking herbivores that use their mouthpart to penetrate and probe plant tissues in order to ultimately access vascular tissue and ingest phloem sap. Because secondary metabolites produced in glandular trichomes can affect the initial steps of the aphid feeding behavior, introducing the formation of defensive terpenes into additional plant tissues via metabolic engineering has the potential to reduce tissue penetration by aphids and in consequence virus transmission. Here, we have developed two multicistronic expression constructs based on the two sesquiterpene traits with activity toward M. euphorbiae previously identified in S. habrochaites. Both constructs are composed of sequences encoding a prenyl transferase and a respective S. habrochaites terpene synthase, as well as enhanced green fluorescent protein as a visible marker. All three coding sequences were linked by short nucleotide sequences encoding the foot-and-mouth disease virus 2A self-processing oligopeptide which allows their co-expression under the control of one promoter. Transient expression of both constructs under the epidermis-specific Arabidopsis CER5-promoter in tomato leaves demonstrated that formation of the two sets of defensive sesquiterpenes, β-caryophyllene/α-humulene and (−)-endo-α-bergamotene/(+)-α-santalene/(+)-endo-β-bergamotene, can be introduced into new tissues in tomato. The epidermis-specific transgene expression and terpene formation were verified by fluorescence microscopy and tissue fractionation with subsequent analysis of terpene profiles, respectively. In addition, the longevity and fecundity of M. euphorbiae feeding on these engineered tomato leaves were significantly reduced, demonstrating the efficacy of this novel aphid control strategy.

Biological Activity of Phytochemicals from Agricultural Wastes and Weeds on Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae)

Spodoptera frugiperda J.E. Smith (Lepidoptera: Noctuidae) is a polyphagous insect pest native to America. Due to its capacity for adaptation and migration, it is currently located in Africa, Asia, and Oceania, where it threatens agricultural crops. The ability of S. frugiperda to develop resistance to insecticides is one of the reasons for the continuous search for more effective, low-cost, and environmentally friendly control products. In the present work, the insecticidal activity of ethanolic and hexane extracts obtained from fresh and dehydrated leaves of Piper auritum Kunth (Piperales: Piperaceae), Piper umbellatum L. (Piperales: Piperaceae), and Cedrela odorata L. (Sapindales: Meliaceae) was studied against first instar larvae of S. frugiperda. The ethanolic extracts of the dehydrated leaves of C. odorata and P. auritum presented insecticidal activity as high (100% mortality at a concentration of 92 mg/cm2) as that obtained with the positive control, Melia azedarach L. (Sapindales: Meliaceae). The GC-MS analysis of the extracts revealed the presence of phytochemicals classified mainly into the groups of monoterpenes, sesquiterpenes, diterpenes, phenylpropanoids, alcohols, and fatty acids. P. auritum grows and propagates rapidly. In addition, due to its low toxicity in mammals and non-target insects, it is a plant with the potential to be used as a botanical insecticide. The exposure of S. frugiperda larvae to low concentrations of ethanolic extract of P. auritum allowed us to observe their biological activity in the development of this insect. The LC50 was 22.1 mg/cm2. At sublethal concentrations (LC21 and LC35) the low fertility of the emerging adults was noticeable.

Analysis Results of Yarrow Medicinal Plant Used as Gastroprotective and Its Use in Health

Introduction: Herbal treatments are a sub-branch of traditional and complementary medicine. People generally use it to strengthen health. It is mostly used with the advice of radio-television, internet and friends. Among the side effects, the most frequent allergic reactions can be seen. tandardized products should be used.It is reported that 80% of the essential oils of mercury (Achillea herba L.) must be monoterpene. Sesquiterpene group is guaianolite, germacranolite, edesmanolite and has anti-inflammatory, anti-edematous, antimicrobial effect. As flavonoid routine, it contains apigenin. Quinine has effects that increase secretion and appetite. It is spasmolytic due to azulene and flavonoids. It is used in gastric mucosa irritations. It is defined as a gastroprotective drug. Azulene and camazulene give wound healing properties to essential oil. The symptoms of inflammation are relieving. Method: Plants (Achillea herba L.) Grown in July Organic Farm in Konya region were used. Analyzes were conducted in the laboratory of the Western Mediterranean Antalya Regional Directorate of Agriculture and Forestry. Total volatile oil content flavonoid amount was determined in the analysis. The amount of essential oil of lavender plant grown in Konya region was measured by hydrodistillation method. Essential oil components were measured by GC-MS / FID method. Result: In this study, we aimed to present phytochemical analysis of mercury (Achillea herba L.)) Plant grown in Konya region. Total essential oil amount was found to be 0.62%. Piperitone takes the first place with 31.25% and p-mentha -1, 5-dien-8-ol with 14.49% and α-pinene with 10.61%. When the content analysis of European countries is examined in the literature studies, it is seen that the amount of Kamuzulen and monoterpene in the plants grown in Estonia region is higher than other European countries (Hungary, Greece, Moldova, Lithuania, and Germany). Millefolii herba is recommended as gastroprotective drug. It is also used after prostate adenectomy because of its antiinflammatory properties.

Characterization of the essential oils from leaves of different sweet potato cultivars grown in Brazil

Sweet potato (Ipomoea batatas (L.) Lam.) leaves are commonly used as human foodstuff in some African and Asian countries. Scientific knowledge about the chemical composition and biological properties of these leaves is useful to allow humans to properly use this specific part of this plant. Thus, this study aimed to evaluate the chemical composition, antioxidant and toxicological potentials of the essential oils obtained from the leaves of four cultivars of sweet potatoes (Batata Roxa, IAPAR 69, Beni Imo and Batata-doce Japonesa) grown in Brazil. Essential oils were isolated by hydrodistillation (100°C, 4 hours) and their components were analyzed by GC/MS and GC/FID techniques. The antioxidant activities and the toxicological potentials of these essential oils were determined by ABTS and Artemia salina assays, respectively. Twenty-three compounds were found in these essential oils, with the sesquiterpene group being the major one. The compounds β-caryophyllene, β-copaene, γ-elemene, and β-elemene were found in concentrations of 1.08 – 28.63% of the essential oil among cultivars. β-Caryophyllene, α-caryophyllene, and δ-cadinene may explain the characteristic aroma of these essential oils. Their moderate antioxidant capacities demonstrated by the mean IC50(ABTS) value of (2.53 ± 0.27) mg mL−1 could be explained by the synergistic effects of α-cadinol, α-caryophyllene, γ-elemene, δ-cadinene, germacrene B, and phytol. The LD50(ASB) values (minimum: 0.60 ppm for cv. Beni Imo; maximum: 4.78 ppm for cv. Batata Roxa) are probably associated with δ-cadinene, α-cadinol, phytol, and α-caryophyllene. The high cytotoxicity attributed to this kind of essential oil shows that its use as a natural food preservative can be harmful to human health. The use of sweet potato leaves as a human foodstuff must be also considered with caution. As far as we are aware, no studies on the essential oils of these cultivars of sweet potato grown in Brazil were previously reported in the literature.

Comparison of the separation process of crude citronella oil using vacuum fractionation distillation on a pilot plant scale and laboratory scale

Crude citronella oil contains a mixture of components such as a group of hydrocarbon monoterpenes compounds, oxygenated monoterpenes, and sesquiterpenes. Therefore, it has low economic value and low functional value. A single component with high purity can be obtained through chemical and physical properties analysis. Based on the physical properties of the constituent components of citronella oil, the boiling points of each component are quite adjacent so that a single component can be separated by the fractionation distillation process. This study aims at determining the optimum condition (temperature, pressure, and reflux ratio) of a pilot plant scale fractionation with 8 meters of the column and the capacity of 200kg (raschig ring packing; temperature range 115-118°C and 118-121°C, reflux ratio 4:1 and 2:1) and comparing it to the laboratory scale (raschig ring packing; temperature range 115-118°C and 118-121°C, reflux ratio 2:1). Although the laboratory scale of fractionation distillation produced good quality rhodinol with 85% purity, the scale-up version of the pilot plant scale still cannot be occupied. For the citronellal fraction, both fractionation distillation process produced poor quality with only 50% purity. This occurred due to the different dimensions that lead to a higher pressure drop. A higher pressure drop will change the optimum temperature conditions.

Study on Soil Properties towards Formation of High Quality Agarwood Resin in <i>Aquilaria crassna</i>

Agarwood has been used for its fragrance and medicinal properties in Asian culture for centuries. In recent years, agarwood gains its popularity in the west due to its usage in perfume formulation. Unfortunately its supply not meets the augmentation market demand. This is mostly because of depleting nature agarwood reservoir and lack of induction technique that can produce agarwood consistently in the plantation. In this study, we look into a case where artificial inducing technique successfully produced high quality agarwood. To assure its quality, agarwood chip was analysed by Gas Chromatography for its chemical profiles. Discovered compounds were identified as sesquiterpene group which also had been characterized as major agarwood compound listed on previous studies. Few compounds that are detected such as δ-cadinene (0.20%), jinkoh-eremol (22.09%), epi-α-cadinol (4.74%), agarospirol (3.75%) and others. Soil condition that contributes into this agarwood formation; soil analysis on physical properties, chemical properties and nutrients content of the soil have been analyzed. Based on the findings, soil condition is an important factor to successfully induced high quality agarwood.

The Extraction of Essential Oil from Piper Cubeba by Using Solvent Free Microwave Extraction Method

This research aims to study the production of essential oil from Piper Cubeba using the solvent-free microwave extraction (SFME) method. Before extraction, the raw materials are prepared in the form of grains and powders to vary the size of the raw materials. Time variation was carried out at microwave power 180 Watt Analyses were then performed on the resulting essential oil using both physical and chemical tests of density and solubility with 96% alcohol. Analyses of chemical compounds within the essential oil were then performed using the Gas Chromatograph Mass Spectrometry (GC-MS). It was found that the production of essential oil from Piper Cubeba using the SFME method was affected by microwave power, grain size, and treatment duration. Results from physical and chemical analyses revealed that the resulting cubeb oil has 0.86 g/mL density, which means that essential oil produced using the SFME method is lighter compared than those produced using MAHD methods. Results from GC-MS analyses showed eight components detected from the production of essential oil from Piper cubeba using the SFMEmethod; Copaene (39.28%), Cubebene (23.83%), Isoledene (11.66%), Naphthalene (6.65%), Phellandrene (5.81%), Asarone (5.71%), Cadidene (4.90%), and Caryophyllene (2.16%) which contents belong to the sesquiterpene group

ANALISIS SENYAWA TERPENOID ANTIJAMUR PADA FRAKSI AKTIF EKSTRAK KULIT KAYU CEMPAKA PUTIH (MICHELIA ALBA) DENGAN METODE GAS CHROMATOGRAPHY-MASS SPECTROSCOPY

The bark extract of Michelia alba was able to inhibit the growth of Curvularia verruculosa fungus which was isolated from leaf spot disease in rice. Separation of the active compound was carried out by column chromatography method using the stationary phase of silica gel and the mobile phase of a mixture of n-hexane-acetone (3: 1). Separation of the active extracts resulted in 10 combined fractions, where 4 fractions showed very strong inhibition, namely the HAE fraction (31.50 mm), HAF (30.13), HAG (48.50), and HAH (34.88). The composition of terpenoid compounds in these fractions was analyzed by Gas Chromatography-Mass Spectrometry. The compound ledenoxid (II) and isoaromadendrene epoxide werefound in almost all of the active fractions, while spathulenol wasfound in the HAF and HAG fractions. Other terpenoid compounds found werecis-farnesol, trans-p-mentha-1 (7), 8-dien-2-ol, and neoclovenoxid-alcohol in the HAE fraction, (-)-caryophyllene oxide and tomentosin in the fraction of HAG. All of the detected terpenoid compounds were compounds from the sesquiterpene group.
 Keywords: Michelia alba extract, inhibitory power, Curvularia verruculossa, sesquiterpenes

Identification of a female-produced pheromone in a destructive invasive species: Asian longhorn beetle, Anoplophora glabripennis

Male-produced pheromone components have been reported in the Asian longhorn beetle, Anoplophora glabripennis (Motschulsky) (Coleoptera: Cerambycidae), but field attraction to these components has been less than overwhelming. Female ALBs were observed rhythmically extending the genitalia in a manner reminiscent of female calling behaviors in other cerambycid species. We thus hypothesized that female ALBs release volatile pheromone while performing this sex-specific behavior. A group of sesquiterpenes, including a major compound α-longipinene and several minor ones α-cubebene, α-ylangene, (−)-α-copaene, α-bergamotene, β-caryophyllene, and α-farnesene, found in genitalia extracts from virgin females elicited male antennal responses. Y-tube olfactometer assays indicated significant attraction of α-longipinene to both sexes in either the presence or absence of host volatiles. This compound was also detected in genitalia extracts from virgin males, though in much lower quantities than in females. Dose–response experiments conducted in the y-tube olfactometer and field both revealed that α-longipinene was attractive at the higher doses, but not at the lower ones. In the field, traps baited with a blend containing α-longipinene, α-cubebene, and β-caryophyllene captured significantly more ALB than solvent controls. The trap catches of α-longipinene combined with either the minor components or host compounds were both greater than those of α-longipinene alone, but the difference was not significant. These results indicate that α-longipinene is a new type of female-produced volatile pheromone in ALB, and the attraction may be synergistically enhanced by several minor components. Sesquiterpenes may play an important role in intraspecies chemical communication of this insect.

Chemical profiling and cytotoxic activity of 150-year old original sample of Jerusalem Balsam

Herbal formulations have been used in ethnomedicine and pharmacy around the world for thousands of years. One of them is Jerusalem Balsam (JB), which came into use in the seventeenth century. Today, people still produce and use it regularly as prophylactic supplement.JB has been widely used in Europe since the nineteenth century, as a remedy possessing antibacterial, antifungal and anti-inflammatory activities. The composition of the product was not known, although possible formulations were reported. In this study the original sample, which dated back to 1870, was investigated for chemical composition and cytotoxic activity. The obtained results were compared with results from more recently produced samples. Several tests were carried out, namely GC-MS, UPLC-PDA-Q-TOF-MS and MTT.Only the 150-year old sample showed a significant cytotoxic activity on cancer cell lines. At a concentration of 125 μg/mL after 72 h of incubation, the original sample inhibited almost 90% of cell metabolic activity, while contemporary samples showed none or little activity. None of the tested samples showed a significant impact on normal cells. These results may be attributed to the activities of benzoic acid and its derivatives, cinnamic acid derivatives, vanillin, group of sesquiterpenes and cembrene.

Essential Oil Yield and Composition of the Balkan Endemic Satureja pilosa Velen. (Lamiaceae).

Satureja pilosa Velen. senso lato is a Balkan endemic plant that is not well characterized and is found on rocky outcrops of limestone base in Stara Planina (the Balkan Mountains) and the Rhodope Mountains. The objective of this study was to assess the variability of essential oil (EO) content and composition of S. pilosa collected at 33 locations across the Balkan and Rhodope Mountains in Bulgaria using advanced statistical methods including cluster analysis. The EO content in dried aboveground biomass varied from 0.52% to 2.03%. More than 21 EO constituents were identified, belonging to the groups of monoterpenes and sesquiterpenes. The monoterpenes were the predominant class, comprising 84.8% to 96.1% of the total EO. Thymol and carvacrol were the major constituents of the phenolic monoterpenoids. Thymol varied from 36.6% to 67.1% and carvacrol varied from 52.4% to 93.0% of the total oil. p-Cymene also varied widely, from 9.6%–34.0%. There were significant variations between locations and within a location in the EO content and composition. This study identified several chemotypes: (1) thymol and p-cymene; (2) thymol, p-cymene and γ-terpinene; (3) carvacrol and p-cymene; (4) carvacrol, p-cymene and γ-terpinene; and (5) carvacrol. This is the first comprehensive study on the endemic plant S. pilosa that identified several chemotypes based on the EO composition. The S. pilosa EO from the five different chemotypes exhibited larvicidal and mosquito repellent activity against Aedes aegypti. The identified chemotypes can be utilized for the development of new varieties with desirable compositions to meet specific industry needs and new mosquito management control products.

A New Modeling Approach for Estimating Abiotic and Biotic Stress-Induced de novo Emissions of Biogenic Volatile Organic Compounds From Plants

The emission of biogenic volatile organic compounds (BVOCs) is usually thought to depend on species-specific emission capacities that vary with seasonal and phenological conditions. Actual – so called constitutive - emissions are then calculated from prevailing temperature and radiation. However, various abiotic and biotic stressors such as ozone, extreme radiation and temperature conditions, as well as wounding e.g. from insect feeding, can lead to de-novo emissions of stress-induced BVOCs (sBVOCs) that may excel constitutive emissions by more than an order of magnitude. These emissions often have a considerable different compound composition and are short-lived but can prolong under continuous stress for quite some time. Thus they may easily have a large impact on overall regional BVOC emissions. However, sBVOCs are generally not considered in models since up to date no consistent mechanism has been suggested. This manuscript suggests a new mechanism based on the finding that sBVOCs originate from a handful of biosynthetic pathways which synthesize compounds in the groups of monoterpenes, sesquiterpenes, and green leave volatiles, as well as methyl salicylate, ethanol/acetaldehyde, methanol/formaldehyde, and acetone. Isoprene is also considered but since it is often constitutively emitted, the specific role of stress induction is difficult to determine for this compound. A function is proposed that describes the production of all de-novo sBVOCs sufficiently well and scales with stress intensity. It is hypothesized that the response delay and the form of the function is specific for the production pathway and valid for ozone as well as wounding (herbivory) induced stress. Model parameters are then derived from pooled literature data based on a meta-analysis of suitable induction-response measurements of different plant species. The overall emission amount then derives from the intensity and frequency of the stress impulse. We present a number of literature studies that are used to parameterize the new model as well as a selection of evaluations for single- and multiple-stress inductions. Furthermore, coupling and interaction with constitutive emission models as well as limitations and possible further developments are discussed.

Effects of long term storage on secondary metabolite profiles of cannabis resin

The structural identification and the monitoring of the relative concentrations of a wide range of major (3) and minor secondary (16) metabolites used as marker substances for profiling of cannabis resin using GC-FID at the Swedish National Forensic Centre (NFC) has facilitated the mapping of their chemical and physical behaviors over a period of 48months whilst stored under different conditions (exposure to light, exposure to air, temperature). In all cases the behavior of this group of sesquiterpenes, sesquiterpenoids, cannabinoids and waxes could be directly related to their chemical lability/functionality. In particular, the identification of homologue triads for both Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD) together with a group of seemingly chemically inert substances (for example, cannabicyclol(CBL) and the waxes (n-alkanes)) has created new tools for the establishment of common origins between samples of cannabis resins aged under different conditions.Since sampling of the resin blocks in NFC’s method for profiling of cannabis resin is made below the surface, the effects of light incursion were found to be negligible. The effects of exposure to air (and indirectly temperature) were found to be more significant, not unexpectedly as many of the observed transformations were based on oxidation or rearrangement processes.

SECRETORY STRUCTURES AND ESSENTIAL OIL COMPOSITION OF SELECTED INDUSTRIAL SPECIES OF LAMIACEAE

The objective of the study was to perform micromorphological analyses of the secretory structures of leaves and stems of oil-bearing industrial plants from the Lamiaceae family such as lemon balm (Melissa officinalis L.), peppermint (Mentha × piperita L.), sage (Salvia officinalis L.), marjoram (Origanum majorana L., syn. Origanum dubium Boiss.), rosemary (Rosmarinus officinalis L.) and common thyme (Thymus vulgaris L.) using light microscope and scanning electron microscope. In addition, an estimation of the content of volatile substances in the plant species under study was performed using GC-MS, as well as the qualitative and quantitative analysis of essential oil, that is an important component in terms of the estimation of raw material applicability for use in the industry. In the epidermal cells of studied plants, 2 types of Lamiaceae-type glandular trichomes were identified: short- and long-stalked capitate glandular trichomes with single- and bicellular secretory capitulum, and peltate glandular trichomes with eight- and over a dozen-cell secretory capitulum. Capitate trichomes were densely distributed on the surface of the epidermis, while peltate trichomes were sparse, though regular, and were situated in depressions. Glandular trichomes were found more frequently on leaves than on stems. The cuticle of the abaxial of leaf was characterized in most cases by the occurrence of larger average diameter peltate trichomes compared to the cuticle of the adaxial side of leaf. Peppermint produced the largest structures accumulating essential oil on the leaves (average diameter of peltate trichomes – 78.48 µm on the adaxial side of leaf, up to 96.43 µm), while on the stem, the highest average diameter of the peltate trichomes was observed in sage (an average of 75.53 µm, up to 85.99 µm). The lemon balm was characterized by the presence of capitate and peltate trichomes with the smallest diameter (an average of 44.26 µm). Lemon balm was characterized by the greatest density of glandular trichomes compared to other plant species. Among the plants studied, the highest content of oil was noted in the case of thyme and peppermint (2.22% and 2.20% v/w, respectively), and the lowest in green parts of lemon balm (0.17% v/w). The isolated essential oils contained predominantly components from the groups of monoterpenes and sesquiterpenes, and it is the presence of those substances that determines the possibility of utilizing the plants studied for a variety of purposes.