Sesquiterpenoids from aged Artemisia argyi and their 3D-QSAR for anti-HBV activity.

Artemisia argyi Levl. Et Vant, commonly known as "Chinese Mugwort," has been utilized in traditional Chinese medicine and cuisine for centuries. Aged Chinese Mugwort has been uncovered to possess superior quality and safety, and its ethyl acetate extract has been found to exhibit anti-hepatitis B virus (HBV) activity. In this study, twenty-five sesquiterpenoids were isolated and characterized from three-year-aged A. argyi. Among them, 14 previously undescribed sesquiterpenoids (1-14), featuring double bond oxidation or ring opening. It is hypothesized that during the aging process, sesquiterpenes undergo oxidative transformation of their double bonds to form alcohols due to external factors and inherent properties. The anti-HBV activity and cytotoxicity of all compounds were assessed in vitro using HepG 2.2.15 cells, and their structure-activity relationships were analyzed through three-dimensional quantitative structure-activity relationship (3D-QASR) techniques. The α-methylene-γ-lactone sesquiterpenoid derivatives were discovered to have potent inhibitory activity against HBV. This research may broaden the potential applications of Chinese Mugwort and offer further guidance for its development and utilization as functional food or traditional Chinese medicine.

The sesquiterpene lactone mix: A review of past, present and future aspects.

The sesquiterpene lactones (SLs) are secondary plant metabolites, which are widespread in the Compositae/Asteraceae plant family. The first SLs were detected more than 100 years ago, and allergic contact dermatitis from Compositae has been reported since the beginning of the 1900s, but it was not until the late 1960s and early 1970s that a collaboration between dermatologists, chemists and botanists led to the detection of SLs as the main allergens of Compositae plants. In the 1980s, the SL mix, consisting of equimolar amounts of alantolactone, costunolide and dehydrocostus lactone, was developed as a screening agent for Compositae sensitisation. Today, after inclusion of SL mix in the baseline series, the mean prevalence of reactions in Europe is around 1%, and in North America 0.8%. In countries outside Europe and North America, the prevalence ranges between 0% and 10.7%. The detection rate of SL mix is lower than that of some plant extracts, and ideally, SL mix should be supplemented with a mix of SLs from locally prevalent allergenic plants. The prevalence of positive reactions to SL mix suggests continued baseline testing in most European countries, North America, New Zealand, Australia and probably some Chinese centres.

Eudesmane-type sesquiterpenoids from the aerial parts of Artemisia lavandulaefolia and their anti-pancreatic cancer activities.

Five undescribed eudesmane sesquiterpenoids, artemilavanins A-E, and one undescribed rearranged eudesmane sesquiterpenoid, artemilavanin F, were isolated from the 95% ethanol extract of the aerial parts of Artemisia lavandulaefolia DC., along with ten known compounds. The structures and configurations of undescribed compounds were mainly elucidated by spectroscopic analyses and single-crystal X-ray diffraction analysis. Among all isolated compounds, artemilavanin F exhibited inhibitory activity on PANC-1 pancreatic cancer cells with IC50 of 9.69 ± 2.39 µM. Artemilavanin F inhibited PANC-1 cell proliferation by induction of G2/M cell cycle arrest and apoptosis mediated by downregulation of cyclin-dependent kinases and accumulation of reactive oxygen species. Moreover, artemilavanin F inhibited the colony formation, cell migration and sphere formation of PANC-1 cells, indicating the suppression of stem-cell-like phenotype of PANC-1 cells. Further results confirmed that the expression of cancer stem cell markers such as Bmi1, CD44, CD133 were inhibited by artemilavanin F. Downregulation of epithelial-mesenchymal transition (EMT) markers such as N-cadherin and Oct-4 indicated the potential of artemilavanin F in prevention of metastasis.

Unusual 5/5 fused bicyclosesquiterpenoids from Eupatorium adenophorum.

The chemical analysis on the aerial sections of Eupatorium adenophorum Spreng. resulted in the identification of four unprecedented 5/5 fused bicyclosesquiterpenoids, eupatorid A (1), and its analogues named eupatorester A-C (2-4) using various chromatographic techniques. Their structures were unambiguously confirmed by detailed spectroscopic investigations (including 1D, 2D-NMR and HRMS), and single crystal X-ray diffraction. The anti-inflammatory activities, in vitro tumor growth inhibitory activities and antibacterial activities of these compounds were evaluated.

Comparative analysis of complete Artemisia subgenus Seriphidium (Asteraceae: Anthemideae) chloroplast genomes: insights into structural divergence and phylogenetic relationships.

BACKGROUND: Artemisia subg. Seriphidium, one of the most species-diverse groups within Artemisia, grows mainly in arid or semi-arid regions in temperate climates. Some members have considerable medicinal, ecological, and economic value. Previous studies on this subgenus have been limited by a dearth of genetic information and inadequate sampling, hampering our understanding of their phylogenetics and evolutionary history. We therefore sequenced and compared the chloroplast genomes of this subgenus, and evaluated their phylogenetic relationships. RESULTS: We newly sequenced 18 chloroplast genomes of 16 subg. Seriphidium species and compared them with one previously published taxon. The chloroplast genomes, at 150,586-151,256 bp in length, comprised 133 genes, including 87 protein-coding genes, 37 tRNA genes, 8 rRNA genes, and one pseudogene, with GC content of 37.40-37.46%. Comparative analysis showed that genomic structures and gene order were relatively conserved, with only some variation in IR borders. A total of 2203 repeats (1385 SSRs and 818 LDRs) and 8 highly variable loci (trnK - rps16, trnE - ropB, trnT, ndhC - trnV, ndhF, rpl32 - trnL, ndhG - ndhI and ycf1) were detected in subg. Seriphidium chloroplast genomes. Phylogenetic analysis of the whole chloroplast genomes based on maximum likelihood and Bayesian inference analyses resolved subg. Seriphidium as polyphyletic, and segregated into two main clades, with the monospecific sect. Minchunensa embedded within sect. Seriphidium, suggesting that the whole chloroplast genomes can be used as molecular markers to infer the interspecific relationship of subg. Seriphidium taxa. CONCLUSION: Our findings reveal inconsistencies between the molecular phylogeny and traditional taxonomy of the subg. Seriphidium and provide new insights into the evolutionary development of this complex taxon. Meanwhile, the whole chloroplast genomes with sufficiently polymorphic can be used as superbarcodes to resolve interspecific relationships in subg. Seriphidium.

Chemical Constituents from Leaves of Baccharis sphenophylla (Asteraceae) and Their Antioxidant Effects.

Baccharis is one of the largest genera of Asteraceae and its species are used in folk medicine for several medicinal purposes due to the presence of bioactive compounds. We investigated the phytochemical composition of polar extracts of B. sphenophylla. Using chromatographic procedures, diterpenoids (ent-kaurenoic acid), flavonoids (hispidulin, eupafolin, isoquercitrin, quercitrin, biorobin, rutin, and vicenin-2), caffeic acid, and chlorogenic acid derivatives (5-O-caffeoylquinic acid and its methyl ester, 3,4-di-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, and 3,5-di-O-caffeoylquinic acid and its methyl ester) were isolated from polar fractions and are described. The extract, polar fractions, and fifteen isolated compounds were evaluated in relation to radical scavenging activity using two assays. Chlorogenic acid derivatives and flavonols exhibited higher antioxidant effects, confirming that B. sphenophylla is an important source of phenolic compounds with antiradical properties.

Derivatives of sesquiterpenes, 2-furaldehyde, phenols, and alkaloids isolated from Taraxacum mongolicum.

Four new compounds (1-4), together with 23 known compounds (5-27), were isolated from the whole plant of Taraxacum mongolicum. Among them, one racemic mixture (4) was separated with a chiral HPLC column. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of compounds 1, 3, and 4 were determined via comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 3 showed an inhibitory effect against aldose reductase with a 59.1% inhibition. Two known compounds (13 and 27) showed α-glucosidase inhibition of 51.5% and 56.0%, respectively.

Bioactive constituents from the rhizomes of Atractylodes macrocephala.

Twelve undescribed compounds including five sesquiterpenes (1-5), one monoterpene (6), and four lignans (7a/7b and 8a/8b), along with two other types (9 and 10) were isolated from the rhizomes of Atractylodes macrocephala. Among them, two pairs of enantiomers (7a/7b and 8a/8b) were successfully separated by chiral-phase HPLC, while racemate 9 could not be resolved. Their structures and absolute configurations were unambiguously elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Notably, compounds 1 and 2 are rare sesquiterpene hybrids featuring an eudesmanolactam linked to a resorcinol or methyl 2-methylpentanoat through a CN bond. Compound 3 represents the first example of eudesmanolide sesquiterpene with an oxygen-bridge between C-8 and C-14. Compounds 7a and 7b are a pair of rare enantiomeric benzodioxane norneolignans. Additionally, compound 2 exhibited weak cytotoxicity against SGC-7901 cells. Compound 4 significantly promoted the proliferation of LPS-induced IEC-6 cells with the rate of 117.2%.

Phylogenetic analysis of chloroplast genome of Tussilago farfara L / 药学学报

italic>Tussilago farfara L. is a perennial herb of Tussilago genus in the Compositae family. Its dried buds and leaves have good biological activities and have a long history of medicinal use in China and Europe. In this paper, we investigated the whole chloroplast genome characteristics, sequence duplication, structural variation and phylogeny of the Tussilago farfara L. After sequencing the Tussilago farfara L. chloroplast genome using Illumination technology, the complete Tussilago farfara L. chloroplast genome was further obtained by assembly and annotation, followed by a series of inverted repeat-large single copy/small single copy region contraction and expansion analysis, genome sequence variation, etc. The sequences of 13 homologous plants downloaded from NCBI were used to construct a neighbor-joining phylogenetic tree. The results showed that the total GC content of the chloroplast genome was 37.4% and the length was 150 300 bp; 125 genes were annotated, including 82 protein-coding genes, 35 tRNAs and 8 rRNAs; 148 (simple sequence repeats, SSR) loci were detected, and the relative synonymous codon usage showed that 31 codons out of 64 codons had a usage of >1. In the phylogenetic analysis, the chloroplast genomes of the seven species of Asteraceae, including the Yulin Tussilago farfara L., were highly conserved, and the sequence variation of the (large single-copy, LSC) and (small single-copy, SSC) regions was higher than that of the (inverted repeat, IR) region. This is in general agreement with the reported phylogeny of Yulin Tussilago farfara L. In this study, we obtained a high quality chloroplast genome and analyzed its genome characteristics, codon preference, SSR characteristics, SC/IR boundary, sequence variation and phylogeny, which can provide a basis for species identification, genetic diversity analysis and resource development of this medicinal plant.

The Ethnopharmacological Uses, Metabolite Diversity, and Bioactivity of Rhaponticum uniflorum (Leuzea uniflora): A Comprehensive Review.

Rhaponticum uniflorum (L.) DC. (syn. Leuzea uniflora (L.) Holub) is a plant species of the Compositae (Asteraceae) family that is widely used in Asian traditional medicines in China, Siberia, and Mongolia as an anti-inflammatory and stimulant remedy. Currently, R. uniflorum is of scientific interest to chemists, biologists, and pharmacologists, and this review includes information from the scientific literature from 1991 to 2022. The study of the chemodiversity of R. uniflorum revealed the presence of 225 compounds, including sesquiterpenes, ecdysteroids, triterpenes, sterols, thiophenes, hydroxycinnamates, flavonoids, lignans, nucleosides and vitamins, alkanes, fatty acids, and carbohydrates. The most studied groups of substances are phenolics (76 compounds) and triterpenoids (69 compounds). Information on the methods of chromatographic analysis of selected compounds, as well as on the quantitative content of some components in various organs of R. uniflorum, is summarized in this work. It has been shown that the extracts and some compounds of R. uniflorum have a wide range of biological activities, including anti-inflammatory, antitumor, immunostimulatory, anxiolytic, stress-protective, actoprotective, antihypoxic, anabolic, hepatoprotective, inhibition of PPARγ receptors, anti-atherosclerotic, and hypolipidemic. Published research on the metabolites and bioactivity of R. uniflorum does not include clinical studies of extracts and pure compounds; therefore, an accurate study of this traditional medicinal plant is needed.

Chemical structures and anti-tyrosinase activity of the constituents from Elephantopus scaber L.

Four undescribed compounds including one germacrane-type sesquiterpene lactones (1), alkaloid (2) along with two neolignans (3-4) were isolated from Elephantopus scaber L. Their structures and absolute configurations were elucidated unambiguously by means of 1D and 2D NMR spectroscopic data analysis, and quantum chemical electronic circular dichroism calculations, as well as single-crystal X-ray crystallography. Their anti-tyrosinase activities have been evaluated in vitro and compound 2 exhibited significant inhibitory activity. Furthermore, molecular docking was performed to study the interaction patterns between 2 and the tyrosinase.

Six new sesquiterpenoids from the fruits of Xanthium italicum.

Four new germacrane-type sesquiterpenoids (1-4) and two new guaiane-type sesquiterpenoids (5-6) were isolated from the fruits of Xanthium italicum Moretti. The structures of the new compounds were elucidated on the basis of spectroscopic analysis and X-ray diffraction experiment. Compounds 1, 2 and 6 showed the anti-inflammatory effects against the activation of NF-κB induced by lipopolysaccharide (LPS) with IC50 values of 20.12, 22.89 and 68.66 µM, respectively.

Allergic contact dermatitis to Compositae: An Australian case series.

BACKGROUND: Allergic contact dermatitis (ACD) to Compositae is caused by sensitisation to sesquiterpene lactones (SQLs) and subsequent exposure can occur from direct handling or from airborne transmission. Plants from the Compositae family are ubiquitous globally and their plant extracts are also used in various products. OBJECTIVES: Investigation of contact allergy (CA) and allergic contact dermatitis (ACD) to Compositae at a single dermatology centre. METHODS: A retrospective case review was performed on patients undergoing patch testing to Compositae between January 2011 and December 2020 in Melbourne, Australia. RESULTS: Of 3679 patients, 44 (1.2%) patch tested positive to Compositae and 19 (43.2%) reactions were deemed relevant. Thirteen cases (68.4%) were from direct contact with Compositae plants, mostly in gardeners. Six cases (31.6%) were from personal products and all these patients were female. Involvement of the face was significant (p = 0.007). Simultaneous allergic reactions included SQL mix in eight (42.1%), fragrance mix in seven (36.8%), potassium dichromate in three (15.8%) and colophonium in two (10.5%) cases. CONCLUSION: Contact with Compositae from gardening contributed most cases of ACD; however, personal products accounted almost one-third of cases. Treatment options remain limited and avoidance is the most important aspect of management.

Advances in research on the protective mechanisms of traditional Chinese medicine (TCM) in myocardial ischaemia-reperfusion injury.

CONTEXT: Developing effective drugs to treat myocardial ischaemia-reperfusion (MI/R) injury is imperative. Traditional Chinese medicines (TCMs) have had considerable success in the treatment of cardiovascular diseases. Elucidating the mechanisms by which TCMs improve MI/R injury can supplement the literature on MI/R prevention and treatment. OBJECTIVE: To summarise TCMs and their main protective mechanisms against MI/R injury reported over the past 40 years. METHODS: Relevant literature published between 1980 and 2020 in Chinese and English was retrieved from the Web of Science, PubMed, SpringerLink, PubMed Central, Scopus, and Chinese National Knowledge Infrastructure (CNKI) databases. Search terms included 'medicinal plants', 'myocardial ischaemia reperfusion injury', 'Chinese medicine prescriptions', 'mechanisms', 'prevention', 'treatment' and 'protection'. For inclusion in the analysis, medicinal plants had to be searchable in the China Medical Information Platform and Plant Database. RESULTS: We found 71 medicinal species (from 40 families) that have been used to prevent MI/R injury, of which Compositae species (8 species) and Leguminosae species (7 species) made up the majority. Most of the effects associated with these plants are described as antioxidant and anti-inflammatory. Furthermore, we summarised 18 kinds of Chinese compound prescriptions, including the compound Danshen tablet and Baoxin pill, which mainly reduce oxidative stress and regulate mitochondrial energy metabolism. DISCUSSION AND CONCLUSIONS: We summarised TCMs that protect against MI/R injury and their pharmacological mechanisms. This in-depth explanation of the roles of TCMs in MI/R injury protection provides a theoretical basis for the research and development of TCM-based treatment drugs.

The complete chloroplast genome sequence of medicinal plant Centipeda minima (Compositae).

The complete chloroplast genome sequence of Centipeda minima (L.) A. Braun et Aschers (Compositae) has been characterized by Illumina pair-end sequencing. The chloroplast genome is 152,351 bp in length, including a pair of inverted repeats (IRs) of 25,004 bp (12.1%) and a large single copy (LSC) and a small single copy (SSC) region of 83,972 bp (55.1%) and 18,371 bp (32.8%), respectively. The chloroplast genome includes 127 genes, which contain 83 protein-coding genes, 36 transfer RNA genes, and 8 ribosomal RNA genes. The nucleotide composition is asymmetric (31.1% A, 18.5% C, 19.0% G, 31.4% T). The overall GC content of C. minima chloroplast genome is 37.5%. Phylogenetic analysis illustrates that C. minima is closely related to other Asteraceae species, including Helianthus annuus subsp. texanus, Tithonia diversifolia and Xanthium sibiricum with a strong bootstrap value of 100.

Phytochemical investigation of the fruits of Xanthium strumarium and their cytotoxic activity.

Eight pentacyclic triterpenoids including two new ones (1, 2) were isolated from the fruits of Xanthium strumarium. Their structures were elucidated by extensive spectroscopic analysis. All isolates were evaluated for in vitro cytotoxic activity on HepG2, A549, HCT116 and SW480 cancer cells. Among them, the new compound 2 was found to exhibit significant cytotoxic activity on A549, HCT116 and SW480 cancer cells with IC50 values of 9.68, 4.27 and 7.58 µM, respectively. Further, 2 was selected for cell cycle analysis and results revealed that 2 could cause HCT116 cell cycle arrest in G1 phase. In addition, Annexin V-FITC/PI staining assay showed that 2 could induce the death of HCT116 cells.

Achillea fragrantissima (Forssk.) Sch.Bip. methanolic extract exerts potent antimicrobial activity and causes cancer cell death via induction of caspase-dependent apoptosis and S-phase arrest.

This study was done to evaluate the anticancer potential of Achillea fragrantissima (Forssk.) Sch.Bip. leaves methanolic extract in detail for the first time, in addition to investigating its antimicrobial activity. The antimicrobial assay revealed that the extract exerted high activity against P. vulgaris (MIC = 156.25 µg/ml) and C. albicans (MIC = 625 µg/ml), while moderate activity was observed against other microbes. The extract was also screened against HepG2, A549, HCT116 and MCF7 cancer cells and was found to be active across all cells with highest selectivity and cytotoxic activity being observed for A549 cells (IC50 = 1.21 µg/ml). Further mechanistic studies on A549 cells showed that the extract resulted in S-phase arrest and induced apoptosis via activation of caspase-3, p53 and Bax, in addition to downregulation of Bcl-2. HR-LCMS analysis indicated the presence of 3-hydroxycoumarin, quercetin 3,3'-dimethyl ether and skullcapflavone II which might be responsible for the extract's bioactivity.

Chlorinated bisabolene sesquiterpenoids from the whole plant of Parasenecio rubescens.

Four new chlorinated bisabolene-type sesquiterpenoids (1-4) were isolated during the phytochemical investigation of an acetone extract of the whole plant of Parasenecio rubescens. The structures of 1-4 were determined by analysis of their HRESIMS and NMR spectroscopic data, and the absolute configuration of 1 was established through single-crystal X-ray diffraction. All isolates were evaluated for their cytotoxicity against three cancer cell lines (B16 mouse melanoma, HepG2 human hepatocellular carcinoma, and MCF7 human breast adenocarcinoma), as well as their antimicrobial effects against Staphylococcus aureus, Escherichia coli, and Monilia albicans. As a result, compounds 1-4 displayed a certain degree of antimicrobial activities.