The potential efficacy of sesquiterpenes and their derivatives in treating rheumatoid arthritis: A systematic review.

Rheumatoid arthritis (RA) is an autoimmune disorder primarily targeting peripheral joints. The global prevalence of RA is increasing, posing a significant challenge in patient care management. Despite therapeutic advancements, their inherent limitations highlight the need for further research on safer treatment interventions. Among potential candidates, sesquiterpenes, a subclass of plant secondary metabolites composed of three isoprene units, have exhibited remarkable efficacy in treating various inflammatory disorders, including RA. In this systematic review, we summarized the treatment evidence of sesquiterpenes and their derivatives on RA. Specific major sesquiterpenoids have been discussed in detail, as well as the possible mechanisms by which cells and chemical messengers are involved in treating RA. Our review indicated that sesquiterpenes are potential novel, bioactive compounds for RA prevention and treatment strategies.

Chemical composition of organic extracts of Phyla nodiflora L. in Syria by GC-MS.

Introduction: Phyla nodiflora L. is a perennial herbaceous plant belonging to the Verbenaceae family. It is widely used as an herbal drink to treat many diseases. It has antioxidant, antifungal and anti-inflammatory properties. In traditional medicine, it is used to treat skin infections. However, there is little information on the chemical composition of organic plant extracts. Therefore, the aim of this study was to determine the chemical composition of organic extracts of P. nodiflora L. Methods: In this study, organic extracts were prepared using a continuous Soxhlet extractor and four different solvents with increasing polarity from nonpolar to polar solvents (petroleum ether, chloroform, ethyl acetate, and isopropanol) to ensure the possibility of extracting a wide range of compounds. GC‒MS analysis was performed to determine the chemical constituents of the organic extracts. Results: Nineteen compounds were identified in the petroleum ether (Et) extract, 14 in the chloroform (Ch) extract, 18 in the ethyl acetate (Ea) extract and 15 in the isopropanol (Is) extract. The most important compounds in the Et extract were 1,1-diethoxyethane (33.9 %) and nonadecane (19.9 %). The most important compound in the Ch extract was octacosane (37.4 %). The most important compounds in the Ea extract were 3-hydroxy-dodecanoic acid (17.7 %) and geranyl isovalerate (15.5 %). The most important compound in the Is extract was behenic acid alcohol (18.6 %). The chemical structures of the major compounds were confirmed by mass spectrometry by studying their fragmentation mechanism and comparing the molecular weights of the resulting fragments with the molecular weights of the peaks present in each mass spectrum. Conclusions: The results of this study show that the dominant compounds in nonpolar extracts (petroleum ether and chloroform) are hydrocarbons, ethers, epoxides, and silicon compounds, while the dominant compounds in moderately polar extracts (ethyl acetate and isopropanol) are alcohols, carbonyl compounds, and oxygenated terpenes.

Characterization of the Phytotoxic Potential of Seven Copaifera spp. Essential Oils: Analyzing Active Compounds through Gas Chromatography-Mass Spectrometry Molecular Networking.

In recent years, there has been a need for environmentally friendly compounds for weed management in agriculture. This study is aimed to assess the phytotoxic constituents of oils obtained from oleoresins of seven Copaifera species (known as copaiba oils). Copaiba oils were separated from the resins by hydro-distillation, and the distillates were analyzed using gas chromatography-mass spectrometry (GC-MS) to characterize their chemical compositions. Multivariate analyses and molecular networking of GC-MS data were conducted to discern patterns in the chemical composition and phytotoxic activity of the oils, with the aim of identifying key compounds associated with phytotoxic activity. Seed germination bioassay revealed strong or complete germination inhibition against the monocot, Agrostis stolonifera but not the dicot Lactuca sativa. GC-MS analysis showed variations in composition among Copaifera species with some common compounds identified across multiple species. Caryophyllene oxide and junenol were associated with the observed phytotoxic effects. Automated flash chromatography was used to isolate the major compounds of the oils. Isolated compounds exhibited differing levels of phytotoxicity compared to the oils, suggesting the importance of interactions or synergism among oil components. These findings highlight the potential of copaiba oils as natural herbicidal agents and underscore the importance of considering species-specific responses in weed management strategies.

Surviving adversity: Exploring the presence of Lunularia cruciata (L.) Dum. on metal-polluted mining waste.

The tailings dump of Barraxiutta (Sardinia, Italy) contains considerable concentrations of heavy metals and, consequently, is scarcely colonized by plants. However, wild populations of the liverwort Lunularia cruciata (L.) Dum. form dense and healthy-looking carpets on this tailing dump. L. cruciata colonizing the tailing dump was compared with a control population growing in a pristine environment in terms of: (i) pollutant content, (ii) photochemical efficiency, and (iii) volatile secondary metabolites in thalli extracts. L. cruciata maintained optimal photosynthesis despite containing considerable amounts of soil pollutants in its thalli and had higher sesquiterpene content compared to control plants. Sesquiterpenes have a role in plant stress resistance and adaptation to adverse environments. In the present study, we propose enhanced sesquiterpenes featuring Contaminated L. cruciata as a defence strategy implemented in the post-mining environment.

Antioxidant Activity, Antiproliferative Activity, Antiviral Activity, NO Production Inhibition, and Chemical Composition of Essential Oils and Crude Extracts of Leaves, Flower Buds, and Stems of Tetradenia riparia.

The chemical composition of extracts (CEs) and essential oils (EOs) from Tetradenia riparia leaves, flower buds, and stems was analyzed. Antiproliferative activity against tumor cell lines, NO production inhibition, and antioxidant and antiviral activities were assessed. The CEs contained flavonoids, phenolic acids, coumarins, and saturated fatty acids. The EOs included monoterpenes, oxygenated sesquiterpenes, and diterpenes. NO production inhibition ranged from 76 to 247 µg mL-1, and antiproliferative activity exhibited GI50 between 20 and >204 µg mL-1, with low cytotoxicity (SI: 1.08 to 4.75). Reactive oxygen species inhibition ranged from 45 to 82%. Antioxidant activity varied when determined by the 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay (IC50: 0.51 to 8.47 mg mL-1) and ferric reducing antioxidant power (0.35 to 0.81 µM ferrous sulfate per mg). The reduction in ß-carotene-linoleic acid co-oxidation varied between 76.13 and 102.25%. The total phenolic content of CEs and EOs was 10.70 to 111.68 µg gallic acid mg-1. Antiviral activity against herpes simplex virus type 1 (HSV-1) showed an EC50 between 9.64 and 24.55 µg mL-1 and an SI between 8.67 and 15.04. Leaf EOs exhibited an EC50 of 9.64 µg mL-1 and an SI of 15.04. Our study unveils the diverse chemical composition and multifaceted pharmacological properties of T. riparia, demonstrating its potential as a valuable source of bioactive compounds for therapeutic applications.

Construction of an orthogonal transport system for Saccharomyces cerevisiae peroxisome to efficiently produce sesquiterpenes.

Subcellular compartmentalization is a crucial evolution characteristic of eukaryotic cells, providing inherent advantages for the construction of artificial biological systems to efficiently produce natural products. The establishment of an artificial protein transport system represents a pivotal initial step towards developing efficient artificial biological systems. Peroxisome has been demonstrated as a suitable subcellular compartment for the biosynthesis of terpenes in yeast. In this study, an artificial protein transporter ScPEX5* was firstly constructed by fusing the N-terminal sequence of PEX5 from S. cerevisiae and the C-terminal sequence of PEX5. Subsequently, an artificial protein transport system including the artificial signaling peptide YQSYY and its enhancing upstream 9 amino acid (9AA) residues along with ScPEX5* was demonstrated to exhibit orthogonality to the internal transport system of peroxisomes in S. cerevisiae. Furthermore, a library of 9AA residues was constructed and selected using high throughput pigment screening system to obtain an optimized signaling peptide (oPTS1*). Finally, the ScPEX5*-oPTS1* system was employed to construct yeast cell factories capable of producing the sesquiterpene α-humulene, resulting in an impressive α-humulene titer of 17.33 g/L and a productivity of 0.22 g/L/h achieved through fed-batch fermentation in a 5 L bioreactor. This research presents a valuable tool for the construction of artificial peroxisome cell factories and effective strategies for synthesizing other natural products in yeast.

Chemical Compositions and In Vitro Antioxidant Activities of the Essential Oils of Sawdust and Resin-Rich Bark from Azorean Cryptomeria japonica (Cupressaceae).

In the Azores archipelago (Portugal), forest operations and wood industry generate large amounts of Cryptomeria japonica biomass residues (CJBR), which can be used to produce valuable essential oils (EOs). In this study, we evaluated the chemical composition and antioxidant activities of EOs from Azorean C. japonica sawdust (CJS) and resin-rich bark (CJRRB). The CJS and CJRRB EOs, obtained via hydrodistillation, showed different yield values (0.27% vs. 0.80% v/w, dry weight) and also different chemical profiles, as assessed using GC/MS. A total of 64 and 85 components were identified in CJS and CJRRB EOs, representing 95.7% and 96.9% of the total composition, respectively. The major components in CJS EO were oxygenated sesquiterpenes (mainly α+ß-eudesmol, 1-epicubenol, and cubebol), while in CJRRB EO, the major components were monoterpene hydrocarbons, including α-pinene, δ-3-carene, and limonene (66.6% vs. 6.4% for oxygenated sesquiterpenes and 0% vs. 64% for monoterpene hydrocarbons, respectively). Antioxidant activity was estimated using (i) two radical-based assays, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging activity, and (ii) a lipid model assay, ß-carotene-linoleic acid bleaching activity (BCBA). Both CJS and CJRRB EOs exhibited concentration-dependent antioxidant activities, and their DPPH, ABTS, and BCBA EC50 values were 1107 vs. 1275 µg/mL, 260 vs. 498 µg/mL, and 1764 vs. 662 µg/mL, respectively. The results indicate that both EOs were able to exert antioxidant activity via different mechanisms of action. Therefore, Azorean CJS and CJRRB may be sustainable sources for antioxidant compounds. This study expands the chemical and biological knowledge of CJBR EOs and, consequently, adds more value to the C. japonica EO industry.

Antimicrobial Activity of Drimanic Sesquiterpene Compounds from Drimys winteri against Multiresistant Microorganisms.

In this work, a group of ten sesquiterpene drimanes, including polygodial (1), isopolygodial (2), and drimenol (3) obtained from the bark of Drimys winteri F. and seven synthetic derivatives, were tested in vitro against a unique panel of bacteria, fungi, and oomycetes with standardized procedures against bacterial strains K. pneumoniae, S. tiphy, E. avium, and E. coli. The minimum inhibitory concentrations and bactericidal activities were evaluated using standardized protocols. Polygodial (1) was the most active compound, with MBC 8 µg/mL and MIC 16 µg/mL in E. avium; MBC 16 µg/mL and MIC 32 µg/mL in K. pneumoniae; MBC 64 µg/mL and MIC 64 µg/mL in S. typhi; and MBC 8 µg/mL and MIC 16 µg/mL and MBC 32 µg/mL and MIC 64 µg/mL in E. coli, respectively. The observed high potency could be attributed to the presence of an aldehyde group at the C8-C9 position. The antifungal activity of 1 from different microbial isolates has been evaluated. The results show that polygodial affects the growth of normal isolates and against filamentous fungi and oomycetes with MFC values ranging from 8 to 64 µg/mL. Sesquiterpene drimanes isolated from this plant have shown interesting antimicrobial properties.

Four undescribed sesquiterpenes from Artemisia mongolica and their anti-inflammatory activity.

Four undescribed sesquiterpene compounds (1-4) and six known compounds (5-10) were isolated from A. mongolica. Furthermore, compound 5 was a new natural product previously synthesized. The LPS-stimulated BV2 cells were used as a model to evaluate the anti-inflammatory activity of the isolated compounds, among them, compounds 2, 3 and 4 showed significant inhibition of NO levels with IC50 values of 27.48, 27.39 and 24.96 µM, respectively.

Cytotoxic Pentaketide-Sesquiterpenes from the Marine-Derived Fungus Talaromyces variabilis M22734.

Talaromyces, a filamentous fungus widely distributed across terrestrial and marine environments, can produce a diverse array of natural products, including alkaloids, polyketones, and polyketide-terpenoids. Among these, chrodrimanins represented a typical class of natural products. In this study, we isolated three previously undescribed pentaketide-sesquiterpenes, 8,9-epi-chrodrimanins (1-3), along with eight known compounds (4-11). The structures of compounds 1-3 were elucidated using nuclear magnetic resonance (NMR) and mass spectrometry (MS), while their absolute configurations were determined through X-ray crystallography and electronic circular dichroism (ECD) computations. The biosynthetic pathways of compounds 1-3 initiate with 6-hydroxymellein and involve multiple stages of isoprenylation, cyclization, oxidation, and acetylation. We selected four strains of gastrointestinal cancer cells for activity evaluation. We found that compound 3 selectively inhibited MKN-45, whereas compounds 1 and 2 exhibited no significant inhibitory activity against the four cell lines. These findings suggested that 8,9-epi-chrodrimanins could serve as scaffold compounds for further structural modifications, potentially leading to the development of targeted therapies for gastric cancer.

Genome Mining of Fungal Unique Trichodiene Synthase-like Sesquiterpene Synthases.

Sesquiterpenoids served as an important source for natural product drug discovery. Although genome mining approaches have revealed numerous novel sesquiterpenoids and biosynthetic enzymes, the comprehensive landscape of fungal sesquiterpene synthases (STSs) remains elusive. In this study, 123 previously reported fungal STSs were subjected to phylogenetic analysis, resulting in the identification of a fungi-specific STS family known as trichodiene synthase-like sesquiterpene synthases (TDTSs). Subsequently, the application of hidden Markov models allowed the discovery of 517 TDTSs from our in-house fungi genome library of over 400 sequenced genomes, and these TDTSs were defined into 79 families based on a sequence similarity network. Based on the novelty of protein sequences and the completeness of their biosynthetic gene clusters, 23 TDTS genes were selected for heterologous expression in Aspergillus oryzae. In total, 10 TDTSs were active and collectively produced 12 mono- and sesquiterpenes, resulting in the identification of the first chamipinene synthase, as well as the first fungi-derived cedrene, sabinene, and camphene synthases. Additionally, with the guidance of functionally characterized TDTSs, we found that TDTSs in Family 1 could produce bridged-cyclic sesquiterpenes, while those in Family 2 could synthesize spiro- and bridged-cyclic sesquiterpenes. Our research presents a new avenue for the genome mining of fungal sesquiterpenoids.

Exploring the Larvicidal and Adulticidal Activity against Aedes aegypti of Essential Oil from Bocageopsis multiflora.

This study investigates the chemical composition of the essential oil obtained from the leaves of Bocageopsis multiflora (Mart.) R.E.Fr (Annonaceae), examining its effectiveness in combating both the larvae and adult forms of Aedes aegypti mosquitoes. Additionally, for a deeper understanding of the insecticidal activity, toxicity properties and molecular docking calculations were conducted using the main compounds of this essential oil. GC/MS analysis revealed the presence of 26 constituents, representing 95.2% of the essential oil, with the major components identified as the sesquiterpenes α-selinene, ß-selinene, and ß-elemene. Larvicidal assays demonstrated potent activity of this essential oil with significant LC50 values of 40.8 and 39.4 µg/mL at 24 and 48 h, respectively. Adulticidal assessments highlighted strong efficacy with LC50 of 12.5 µg/mL. Molecular docking analysis identified optimal interaction activities of α-selinene and ß-selinene with key Aedes proteins. The in silico studies comparing synthetic insecticides with the major sesquiterpenes of the essential oil revealed that ß-selinene exhibited a significantly higher binding affinity compared to the other two sesquiterpenes. Also, ADMET studies of the three main sesquiterpenes indicated acceptable drug-like properties. In these findings, safety evaluations showed low toxicity and skin sensitization for the main sesquiterpenes, contrasting with commercial synthetic insecticides. Therefore, in silico analyses suggest promising interactions with Aedes proteins, indicating its potential as an effective alternative to conventional insecticides These results show the larvicidal and adulticidal potential of the essential oil from Bocageopsis multiflora against Aedes aegypti, supported by its predominant constituents, α-selinene, ß-selinene and ß-elemene.

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.

A simple and green offline-online capillary electrophoresis stacking strategy for the simultaneous determination of hydrophobic compounds in complicated samples using sodium dodecyl sulfate as the solubilizer and pseudophase.

BACKGROUND: Capillary electrophoresis is a powerful analytical method featured with high separation efficiency, minimal sample requirements, and reduced organic solvents consumption. However, its low sensitivity hinders its wide application in determination of trace analytes especially for the weakly ionized hydrophobic compounds. Offline and Online capillary electrophoresis stacking methods are more favored to enhance detection sensitivity of analytes. The determination of two sesquiterpenes and an alkaloid from the dried root of Lindera aggregata merged as an example for developing a simple, sensitive and green method for the simultaneous determination of two hydrophobic compounds in complicated matrix samples. RESULTS: An offline-online capillary electrophoresis stacking strategy by integrating micro matrix solid phase dispersion with field-amplified sample stacking and micelle to cyclodextrin stacking has been developed for the simultaneous determination of dehydrocostus lactone, linderane, norisoboldine in complex matrices. The optimized parameters were set at 65 mM sodium dihydrogen phosphate, 35 % methanol, 180 s for sample injection and 210 s for cyclodextrin injection, 20 mM sodium dodecyl sulfate of sample matrix for online stacking; 1:1 sample to MCM-48, 180 s grinding time, and 1000 µL of 20 mM sodium dodecyl sulfate elution for offline procedure. Under the optimum conditions, the method showed good linearity with correlation coefficients (R2 ≥ 0.9927), low limits of detection within the range of 25-50 ng mL-1, satisfactory repeatability and reproducibility below 3.98 %, and acceptable recoveries between 94 % and 97 %. The developed method was successfully applied to two real samples, the root of L. aggregata and rat feces. SIGNIFICANCE: Sodium dodecyl sulfate is firstly used as an eluent in micro matrix solid phase dispersion and plays a dual role throughout the analytical procedure, including extraction solvent in sample preparation and micelle pseudophase during online stacking. It brings great procedure convenience to the method. The sensitivity of this method can improve up to 1283-folds compared with the normal mode. Moreover, the overall strategy indicates satisfied green potential evaluated by greenness assessment tools.

[Active constituents of essential oil from Curcuma phaeocaulis for treatment of dysmenorrhea].

This study aims to identify the active constituents of essential oil from the rhizomes of Curcuma phaeocaulis for the treatment of dysmenorrhea. The compounds were separated and purified by molecular distillation, silica gel and Sephadex LH-20 column chromatography, preparative thin layer chromatography, and semi-preparative high performance liquid chromatography. Their structures were identified by mass spectrometry and nuclear magnetic resonance spectroscopy. The animal model of primary dysmenorrhea and the contraction model of isolated uterine smooth muscle of rats were established to examine the active constituents in the essential oil for treating dysmenorrhea. Six sesquiterpenes were isolated and identified as dehydrocommiterpene A(1), comosone Ⅱ(2), 5α(H)-eudesma-3(4),7(11)-dien-9ß-ol-6-one(3), guaia-6(7)-en-11-ol(4), curcumenol(5), and isocurcumenol(6), among which compound 1 was a novel compound. The animal experiments showed that the essential oil from C. phaeocaulis significantly lowered the level of PGF_(2α) in uterine tissue compared with the model group. The experiment with the contraction model of isolated uterine smooth muscle demonstrated that the components with high boiling points outperformed those with low boiling points in relaxing the uterine smooth muscle, and compounds 1, 2, 5, and 6 isolated from the fraction with a high boiling point had the effect of relaxing the uterine smooth muscle. Among them, compounds 5 and 6 inhibited the extracellular Ca~(2+) influx and intracellular Ca~(2+) release to relax the uterine smooth muscle. In conclusion, the components with high boiling points and sesquiterpenes are the active components in the essential oil of C. phaeocaulis for treating dysmenorrhea.

[Difference of effective component content and key enzyme gene expression of biosynthesis in Atractylodes chinensis with different leaf shapes].

In this study, four Atractylodes chinensis(A. chinensis) with different leaf shapes, such as the split leaf, long and narrow leaf, oval leaf, and large round leaf, were used as experimental materials to establish a method for simultaneously determining atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon in the rhizome of A. chinensis. The expression of key enzyme genes for biosynthesis of acetyl-CoA carboxylase(ACC), 3-hydroxy-3-methylglutaryl-CoA reductase(HMGR), and farnesyl pyrophosphate synthase(FPPS) was detected by real-time fluorescence quantitative polymerase chain reaction(qRT-PCR). High performance liquid chromatography(HPLC) was used to compare the difference in the content of four active components in A. chinensis with different leaf shapes, and the correlation between the content of active components and the expression of key enzyme genes in biosynthesis was discussed. The results show that there was good linearity among atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon in the range of 3.30-33.00 µg·mL~(-1)(r =0.999 7), 12.04-120.40 µg·mL~(-1)(r =0.999 5), 29.16-291.60 µg·mL~(-1)(r =0.999 5), and 14.20-142.00 µg·mL~(-1)(r =0.999 5), respectively. The average recoveries were 99.77%(RSD=2.1%), 98.56%(RSD=1.2%), 103.0%(RSD=1.2%), and 100.6%(RSD=1.5%), respectively. The method was accurate and had good reproducibility, which could be used to simultaneously detect atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon. The results showed that there were significant differences in the content of four active components in A. chinensis with different leaf shapes. The content of atractylodin, atractylenolide Ⅰ, and ß-eudesmol in A. chinensis with split leaves was the highest, which were 1.341 9, 5.237 2, and 12.084 3 mg·g~(-1), respectively. The content of atractylon in A. chinensis with long and narrow leaves was the highest(5.470 1 mg·g~(-1)). The content of atractylodin, atractylenolide Ⅰ, ß-eudesmol, and atractylon in A. chinensis with oval leaves was the lowest. The total content of the four effective components in descending order was A. chinensis with split leaves > A. chinensis with long and narrow leaves > A. chinensis with large round leaves > A. chinensis with oval leaves. The gene expression levels of key enzymes ACC, HMGR, and FPPS in A. chinensis with split leaves were the highest(P < 0.05), and the gene expression levels of key enzymes ACC and HMGR in A. chinensis with oval leaves were the lowest(P < 0.05). The gene expression level of key enzyme FPPS in A. chinensis with large round leaves was the lowest. In A. chinensis with different leaf shapes, the key enzyme gene ACC was significantly positively correlated with the polyacetylene component, namely atractylodin(P < 0.01), and the key enzyme genes HMGR and FPPS were positively correlated with the sesquiterpene components, namely atractylenolide Ⅰ, ß-eudesmol, and atractylon. In summary, the quality of A. chinensis with split leaves is the best, and the biosynthesis of atractylodin is significantly correlated with the gene expression of key enzyme ACC, which provides a theoretical basis for screening and optimizing the germplasm resources of A. chinensis and improving the quality of medicinal materials.

Atramacrolodes A-D (1-4), Four Undescribed Eudesmane-Type Sesquiterpenes from the Rhizome of Atractylodes macrocephala.

Four undescribed sesquiterpenes, atramacrolodes A-D (1-4), along with six known compounds 5-10 were isolated from the rhizome of Atractylodes macrocephala. Compound 3 possessed a new skeleton based on an unprecedented carton-carton connection. Their structures were determined by UV, IR, HRESIMS, NMR spectra, 13C NMR calculation with DP4+ analysis, and the comparison of experimental and calculated ECD spectra. Compounds 5 and 8 showed protective effects against paracetamol-induced liver cell injury.

Glandular Trichomes and Essential Oils Variability in Species of the Genus Phlomis L.: A Review.

The genus Phlomis is one of the largest genera in the Lamiaceae family and includes species used since ancient times in traditional medicine, as flavoring for food and as fragrance in cosmetics. The secretory structures (represented by glandular trichomes) as well as the essential oils produced by them constitute the subject of this review. While representatives of this genus are not typically regarded as large producers of essential oils compared to other species of the Lamiaceae family, the components identified in their essential oils and their biological properties necessitate more investigation of this genus. A comprehensive analysis of the specialized literature was conducted for each of the 93 currently accepted species to identify all the results obtained by researchers regarding the secretory structures and essential oils of this genus up to the present time. Glandular trichomes, still insufficiently studied, present morphological peculiarities that differentiate this genus within the family: they are of two categories: capitate (with a wide distribution in this genus) and dendroid. The peltate trichomes, characteristic of many species of this family, are absent. The essential oils from the species of the genus Phlomis have been much more widely studied than the secretory structures. They show considerable variability depending on the species and the environmental conditions.

A comprehensive review of secondary metabolites from the genus Agrocybe: Biological activities and pharmacological implications.

The genus Agrocybe, situated within the Strophariaceae family, class Agaricomycetes, and phylum Basidiomycota, encompasses a myriad of species exhibiting significant biological activities. This review presents an integrative overview of the secondary metabolites derived from Agrocybe species, elucidating their respective biological activities and potential pharmacological applications. The metabolites under scrutiny encompass a diverse array of biological macromolecules, specifically polysaccharides and lectins, as well as a diverse group of 80 documented small molecular chemical constituents, classified into sterols, sesquiterpenes, volatile compounds, polyenes, and other compounds, their manifesting anti-inflammatory, anticancer, antioxidant, hepatoprotective, antimicrobial, and antidiabetic activities, these metabolites, in which polysaccharides exhibit abundant activities, underscore the potential of the Agrocybe genus as a valuable source of biologically active natural products. The present review emphasises the need for escalated research into Agrocybe, including investigations into the biosynthetic pathways of these metabolites, which could foster the development of novel pharmaceutical therapies to address various health challenges.

Unravelling the Function of the Sesquiterpene Cyclase STC3 in the Lifecycle of Botrytis cinerea.

The genome sequencing of Botrytis cinerea supplies a general overview of the map of genes involved in secondary metabolite synthesis. B. cinerea genomic data reveals that this phytopathogenic fungus has seven sesquiterpene cyclase (Bcstc) genes that encode proteins involved in the farnesyl diphosphate cyclization. Three sesquiterpene cyclases (BcStc1, BcStc5 and BcStc7) are characterized, related to the biosynthesis of botrydial, abscisic acid and (+)-4-epi-eremophilenol, respectively. However, the role of the other four sesquiterpene cyclases (BcStc2, BcStc3, BcStc4 and BcStc6) remains unknown. BcStc3 is a well-conserved protein with homologues in many fungal species, and here, we undertake its functional characterization in the lifecycle of the fungus. A null mutant ΔBcstc3 and an overexpressed-Bcstc3 transformant (OvBcstc3) are generated, and both strains show the deregulation of those other sesquiterpene cyclase-encoding genes (Bcstc1, Bcstc5 and Bcstc7). These results suggest a co-regulation of the expression of the sesquiterpene cyclase gene family in B. cinerea. The phenotypic characterization of both transformants reveals that BcStc3 is involved in oxidative stress tolerance, the production of reactive oxygen species and virulence. The metabolomic analysis allows the isolation of characteristic polyketides and eremophilenols from the secondary metabolism of B. cinerea, although no sesquiterpenes different from those already described are identified.