Phytochemical Analysis最新文献

Introduction: The metabolome of plants is influenced by various factors, especially environmental, as the season in which they are grown. So, distinct varieties of the identical plant might show an increase or decrease in metabolites. The diversity of content of primary and secondary metabolites can also determine the variation in their biological properties. Due to the current occurrence of various fennel varieties, the crop can now be grown for the entire year.

Objective: This work used an integrated approach of LC/MS and NMR analysis to characterize the metabolome of fennel waste of different varieties by multivariate statistical analysis.

Methods: The extracts were investigated by NMR and LC/MS analysis to focus attention on the primary and secondary metabolites. Both LC-HRMS and NMR data were analyzed by principal component analysis (PCA).

Results: The ¹H-NMR analysis led to the identification of 15 primary metabolites, such as amino acids, carbohydrates, and organic acid derivatives. The secondary metabolites identified by LC/MS analysis mainly belong to the phenolic, lipid, and fatty acid compounds classes.

Conclusion: This integrated approach guarantees a precise and complete overview of the variations in the metabolic expression of the fennel varieties grown in different seasons.

Objectives: The quality of 30 batches of the Tibetan Dracocephali tangutici Herba was evaluated using HPLC fingerprinting and DNA sequences.

Methods: Botanical identification of 30 batches of D. tangutici herba was conducted using the DNA barcoding approach, specifically analyzing the ITS and rbcL sequences. HPLC fingerprints of Tibetan Dracocephali tangutici Herba were established. The quality of 30 batches of D. tangutici herba was comprehensively evaluated using principal component analysis (PCA), orthogonal partial least squares discriminant analysis (OPLS-DA), and entropy weighting method (EWM) combined with grey relation analysis (GRA).

Results: The botanical provenance of all 30 batches of herbs was proven to be Dracocephali tangutici Maxim. using DNA barcoding techniques, namely, ITS sequence and rbcL sequence testing. A total of 17 common peaks were chosen from the HPLC fingerprinting analysis. Among these, three peaks were recognized by comparing them with three reference standards: chlorogenic acid, cryptochlorogenic acid, and salvianolic acid B. The similarity scores of the 30 batches of D. tangutici herba varied between 0.846 and 0.991. The 30 batches of samples were categorized into two groups using PCA. The findings from OPLS-DA indicated that chlorogenic acid and four flavonoids could be the crucial components for evaluating the quality of D. tangutici herba. Additionally, the combined evaluation results of EWM and GRA suggested that the quality of the 30 batches of samples varied significantly.

Conclusion: The results of this study can provide a reference basis for the development of quality standards for D. tangutici herba in Tibet.

Introduction: Farfarae Flos is widely used as a traditional herbal medicine. Currently, its size has been the primary grading criterion used in market circulation. Whether this empirical criterion can accurately reflect the quality of the medicinal material has not been systematically studied.

Objective: This study aimed to evaluate the quality of Farfarae Flos from different regions based on their grades.

Methods: Ultra-high performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-ESI-Q/TOF-MS/MS) were applied to study the chemical constituents of Farfarae Flos; high performance liquid chromatography (HPLC) was used to quantify the content of Farfarae Flos samples. Meanwhile, fingerprint analysis and chemometric methods, including principal component analysis (PCA) and analysis of variance (ANOVA), were used to evaluate the quality differences among 33 batches of Farfarae Flos samples of different grades.

Results: A total of 95 individual components were identified in Farfarae Flos. Fingerprint analysis revealed 23 common peaks, with fingerprint similarity among the 33 batches ranging from 0.838 to 0.995. PCA divided the 33 batches of Farfarae Flos into three categories based on their grades. ANOVA indicated significant differences in five of the 14 main active components across different grades of Farfarae Flos, with two components showing extremely significant differences. HPLC content determination showed that the content of 11 main active components was positively correlated with the grades of Farfarae Flos.

Conclusion: This method is straightforward, efficient, and reliable, offering a valuable reference for establishing quality grading standards and ensuring the quality control of Farfarae Flos.

Introduction: Angelica sinensis is one of the most popular traditional Chinese medicines (TCM) and has been extensively used to treat various diseases. Hundreds of endogenous ingredients have been isolated and identified from this herb, but their spatial distribution within the plant root is largely unknown.

Objectives: In this study, we tried to investigate and map within-tissue spatial distribution of metabolites in Angelica sinensis roots.

Material and methods: After optimization of experiment conditions, the 1,5-diaminonaphthalene (1,5-DAN) was chosen as the matrix and was sprayed on the surface of root sections. Then matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI-MSI) was employed to perform in situ detection and obtain detail spatial distribution information of metabolites in Angelica sinensis roots.

Results: The spatial distributions of a wide range of metabolites including organic acids, amino acids, oligosaccharides, and phospholipids were characterized and visualized in Angelica sinensis roots. Majority of these metabolites were located in the phloem and xylem, while ferulic acid was mainly present in the cork layer. The results revealed a dramatic metabolic heterogeneity among different regions of the roots and distinct spatial distribution patterns of different metabolites. Additionally, the metabolic pathways involved in the biosynthesis of choline were also successfully localized and visualized.

Conclusion: This study comprehensively characterized the spatial distribution of metabolites in Angelica sinensis roots, which would prompt the understanding of its chemical separation, biosynthesis, and pharmacological activities.

Introduction: Aqueous stem bark extracts of Aspidosperma rigidum Rusby, Couroupita guianensis Aubl., Monteverdia laevis (Reissek) Biral, and Protium sagotianum Marchand have been reported as traditional remedies in several countries of the Amazonian region. Despite previous research, further investigation to characterize secondary metabolites and the biological activity of extracts is needed to derive potential applications.

Material and methods: Metabolic profiling was carried out using liquid and gas chromatography coupled with mass spectrometry (UHPLC-MS/MS and GC-MS). The chemical composition of the studied plants was further compared by principal component analysis (PCA). Additionally, chemical profiles were correlated with antimicrobial and toxicity activities, which suggested potential metabolites for future research.

Results: We identified 16 and 32 compounds by UHPLC-MS/MS and GC-MS analysis, respectively. Antimicrobial activity was detected in three stem bark extracts. C. guianensis showed inhibition of all tested microorganisms, including antibiotic-resistant strains. Molecular networking approaches, in silico tools, and Pearson's correlation showed that antifungal compounds could be a terpene glycoside (r = 0.918) and/or a phenolic (r = 0.882) metabolite class.

Conclusion: This study highlights the use of the established procedure in exploring the metabolomes of these species, which could be a novel source of antimicrobial drug discovery. Coupling the observed biological potential with UHPLC-MS/MS data has also accelerated the tracing of their bioactive compounds. These findings update the state of the art regarding the chemical composition and biological activity of the plant extracts, defining potential new applications for the pharmaceutical applications.

Introduction: Rheumatoid arthritis (RA) is a chronic autoimmune disease that primarily manifests with symptoms such as heat and toxin. However, the key components and molecular mechanisms of Zhizi Baipi decoction (ZBD) in the treatment of RA are still unclear.

Objectives: The study aimed to explore the mechanism of action of ZBD for treating RA through ingredient analysis, network pharmacology, and experimental validation.

Material and methods: The chemical constituents of ZBD were identified by ultra-high performance liquid chromatography coupled with Q-TOF-mass spectrometry (UPLC-Q-TOF-MS^E). Additionally, the active ingredients of ZBD treating RA were screened by network pharmacology and using molecular docking to verify the binding energy of the active ingredients and ZBD's targets. Then we elucidated ZBD's mechanism of action on collagen-induced arthritis (CIA) model rats. Subsequently, experimental validations were used to validate the findings of network pharmacology.

Results: A total of 84 chemical constituents was identified by UPLC-Q-TOF-MS^E. The results of network pharmacology indicated that ZBD could exert its therapeutic effect on RA through the vascular endothelial growth factor (VEGF) pathway. Molecular docking revealed a strong binding capacity between the target KDR and the active ingredients. Additionally, we quantified the five active ingredients of ZBD. In vivo experiments demonstrated that ZBD inhibited synovial angiogenesis and alleviated the occurrence and progression of RA.

Conclusion: Overall, ZBD has a significant therapeutic effect on RA. The results of qualitative analysis, network pharmacology, molecular docking, and in vivo experiments indicated that the main active components of ZBD could modulate the VEGF pathway to treat RA.

Introduction: Antimicrobial resistance and free radical-mediated oxidative stress and inflammation involved in many pathological processes have become treatment challenges. One strategy is to search for antimicrobial and antioxidant ingredients from natural aromatic plants. This study established a rapid and high-throughput effect-component analysis method to screen active ingredients from Ligusticum chuanxiong essential oil (CXEO).

Objective: The study aims to screen phthalides with antimicrobial and antioxidant activities from CXEO by high-performance thin-layer chromatography (HPTLC)-bioautography combined with HPLC-TOF/MS method.

Methods: Antimicrobial activity was evaluated by disc diffusion and micro broth dilution methods. Antioxidant capacity was performed by DPPH scavenging test. Phthalides in CXEO were identified using HPLC-TOF/MS method. HPTLC-bioautography technique was established to screen phthalides of antifungal and antioxidant activities.

Results: CXEO had significant inhibitory activity against Candida albicans, weak or undetected inhibitory activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. For tested strains of C. albicans, inhibition zone diameters ranged from 13 to 17 mm, and MICs were from 0.5 to 2 mg mL^-1. CXEO also had strong antioxidant activity, IC₅₀ value for scavenging DPPH free radicals was 1.014 ± 0.014 mg mL^-1. Nine phthalides in CXEO were tentatively identified. Ligustilide and senkyunolide A were screened to have both antimicrobial activity against C. albicans and strong DPPH scavenging property.

Conclusion: HPTLC-bioautography-MS-guided strategy is very practical for high-throughput screening of antifungal and antioxidant phthalides from CXEO. In vitro experiments have shown that phthalides and CXEO have good biological activities, which may be used to the treatment of C. albicans infection or oxidative stress damage caused by various diseases. The therapeutic potential should be validated in vivo in the future.

Introduction: Wenyujin Rhizoma Concisum, named as Pian Jianghuang (PJH) in China, is the decoction piece from the dried rhizome of Curcuma wenyujin Y. H. Chenet C. Ling, has been used to relieve pain for many years in China. However, the qualities of PJH in different districts differ greatly due to their growing environments, which would affect their clinical applications.

Objective: To evaluate the qualities of PJH from different districts in China.

Methods: HPLC, Heracles NEO ultrafast gas-phase electronic nose, and Fourier transform near-infrared (FT-NIR) spectroscopy were applied to estimate the qualities of PJH from different districts in China.

Results: By HPLC, the average contents of neocurdione, curdione, germacrone, and furanodiene were 0.203%, 0.151%, 0.022%, and 0.022% in Fujian (FJ); 0.447%, 0.786%, 0.298%, and 0.276% in Zhejiang (ZJ); 0.082%, 0.259%, 0.038%, and 0.019% in Yunnan (YN); 0.041%, 0.022%, 0.260%, and 0.024% in Guangxi (GX); and 0.026%, 0.091%, 0.260%, and 0.016% in Anhui (AH), respectively. By Heracles NEO ultrafast gas-phase electronic nose, the unique odor components in PJH from FJ, YN, and GX were 1,2,4-thiadiazole,5-ethoxy-3-(trichloromethyl), 5,6,7,8-tetrahydroquinoxaline, and 1,3,5-trimethylbenzene, respectively, while ZJ and AH both contained two unique odor components, respectively: pentyl pentanoate and dill ether (ZJ), myrcene, and 2-pentadecanone (AH). Moreover, PJH from above five districts could be discerned quickly by FT-NIR.

Conclusion: The application of multidimensional analytical techniques in quality assessment of PJH from different districts in China would provide a new idea for quality control and geographical origin traceability of traditional Chinese materia medica.

Introduction: As a widely used Chinese herbal medicine, Mume Fructus pulp (MFP) has rich nutritional value and biological activity, but its quality control research is relatively scarce.

Objectives: The objective of the study was to evaluate the quality difference between MFPs from different origins and its adulterant apricot pulp (APP), and to identify potential quality markers.

Methods: The chemical compositions were identified by untargeted metabolomics analysis based on ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry combined with feature-based molecular networking. The effect of the test samples on the gene expression of the pro-inflammatory cytokines was investigated by RT-qPCR and ELISA analyses to determine their anti-inflammatory potential. Antioxidant activity was assessed by a free radical scavenging assay. Subsequently, the relationship between biological activity and chemical composition was analyzed by chemometrics, and the quality index of MFP was preliminarily determined. Based on network pharmacology and molecular docking, quality markers of MFP and their possible molecular mechanisms were further determined.

Results: There were significant differences in the contents of flavonoids and organic acids, as well as the anti-inflammatory and antioxidant activities of MFPs from different habitats. Its adulterant APP was not only different from MFP in composition, but also had significantly weaker biological activity. Sixteen compounds were positively correlated with the antioxidant or anti-inflammatory effects of MFP. Combined with network pharmacology and molecular docking, citric acid, maleic acid, rutin, quercetin, isoquercetin, spiraeoside, and hesperidin were identified as potential quality markers of MFP.

Conclusion: This study showed the potential of untargeted metabolomic analysis combined with bioactivity assays in the identification of herbal quality markers.

Introduction: Ziziphora clinopodioides subsp. bungeana (Juz.) Rech.f. is used in traditional medicine for various purposes. Previous phytochemical studies focused on phenolic compounds, but triterpenoids were almost overlooked.

Objective: The study focused on the isolation of compounds with dual antidiabetic activity from the aerial parts of Z. clinopodioides subsp. bungeana.

Materials and methods: Separation of CHCl₃-soluble fraction by silica gel column chromatography using different mobile phases and purification of compounds by semi-preparative HPLC or preparative TLC. The structures of pure compounds were elucidated by 1D and 2D NMR experiments along with HRMS. Compound 1 was additionally identified by the single crystal X-ray diffraction method. α-Glucosidase inhibitory assay and GLUT4 expression and translocation in C2C12 myotubes were conducted to evaluate antidiabetic potential of isolated compounds.

Results: This phytochemical study led to the isolation of 20 compounds, including a unique monoterpene diperoxy dimer (1). Compounds 7 and 9-11 displayed more potent α-glucosidase inhibitory activity (IC₅₀ 45.3-135.3 μM) than acarbose used as a positive control (IC₅₀ 264.7 μM), while only pomolic acid (5) increased GLUT4 translocation in C2C12 myotubes in a significant manner.

Conclusion: Extensive chromatographic separation led to the isolation and identification of a unique monoterpene diperoxy dimer (1) from aerial parts of Z. clinopodioides subsp. bungeana. Some triterpenes inhibited α-glucosidase, another increased GLUT4 translocation. Although none of the isolated compounds demonstrated dual antidiabetic activity, selected triterpenes proved to be potent antidiabetic agents in vitro.