Phytochemical Analysis最新文献

Introduction: Harmonization of methodological approaches to the analysis of herbal substances containing triterpenoid saponins, considered the largest group of phytochemicals, is essential for the pharmaceutical industry worldwide.

Objectives: This review aimed to perform a comparative analysis of the requirements for the standardization of herbal substances, herbal medicinal products (HMPs), and other herbal materials containing triterpenoid saponins in the pharmacopeial texts of the Russian Federation and the world's leading pharmacopeias.

Materials and methods: The review covers the data on the quantitative and qualitative analysis of herbal substances containing triterpenoid saponins, as presented in the State Register of Medicinal Products of Russia and the monographs of the world's leading pharmacopeias: the European Pharmacopeia, United States Pharmacopeia, British Pharmacopeia, Japanese Pharmacopeia, and the national pharmacopeias of the Eurasian Economic Union (EEU) Member States.

Results: This review compares and discusses the analytical methods used for the standardization of Aesculus hippocastanum L. seeds, Aralia elata (Miq.) Seem roots, Glycyrrhiza spp. roots, Orthosiphon aristatus (Blume) Miq. leaves, and Polemonium caeruleum L. rhizomes with roots. The most common analytical methods used are (HP)TLC and (U)HPLC. The Russian Pharmacopeia also includes titrimetry and spectrophotometry.

Conclusions: The appropriate selection of a group of biologically active compounds for HMP standardization is still challenging. We believe that a rational approach to the standardization of herbal substances and HMPs should be based on the use of herbal substances with maximum extractability and specific pharmacological activity. The harmonized procedures and reference substances for the identification and assay of active metabolites in HMPs must be implemented at all stages of production control from herbal substances to finished dosage forms.

Introduction: Shenqi Tongmai oral liquid (SQTM) is famous for its remarkable effect in the treatment of cardiovascular diseases. However, the SQTM quality evaluation system has not been established.

Objective: The objective of this study is to establish a method for the determination of nine components of SQTM and to screen quality control indicators to comprehensively evaluate the quality of SQTM.

Methods: The fingerprints of SQTM were established, and the contents of nine components in 17 batches of SQTM were determined based on quantitative analysis of multicomponents by single marker (QAMS). The antioxidant activity of samples was determined by the DPPH method and hydroxyl method, and the correlation between the content of nine components and antioxidant activity was analyzed by gray relational analysis (GRA), bivariate correlation analysis (BCA), and partial least squares regression (PLSR). The antioxidant activity of the monomers was confirmed through molecular docking techniques and in vitro experiments.

Results: There was no significant difference in the content between the QAMS method and the external standard method (p > 0.05). The findings from multivariate statistics, molecular docking, and in vitro validation indicated that rosmarinic acid, luteolin, and protocatechualdehyde exhibited significant antioxidant activities, which were important pharmacodynamic components that exerted antioxidant effects and could serve as quality markers (Q-Markers).

Conclusion: The study elucidated the Q-Markers of SQTM and provided a relatively comprehensive approach for the assay of SQTM, which is a promising advance in the quality control of SQTM.

Introduction: Wendan decoction (WDD), a classic Chinese medicine formula, has been used for the treatment of insomnia for hundreds of years. However, the current research on the chemical composition and the material basis of the medicinal effect of WDD is not perfect, which limits further research on it.

Objectives: In the present study, we aimed to propose a methodology for the quality control of WDD based on qualitative and quantitative analysis of its components.

Methods: The chemical composition of WDD was identified through UPLC-Q-Exactive Orbitrap MS technology. Then, high-performance liquid chromatography was utilized to establish the fingerprint of 10 batches of WDD and determine the content of some common peaks. The quality evaluation and quality control of WDD were implemented from three aspects: chemical composition, fingerprint, and content determination.

Results: The study initially identified 113 chemical components, including 51 flavonoids, 13 amino acids, seven nucleotides, five alkaloids, eight phenylpropanoids, eight terpenoids, 12 organic acids, and nine other compounds. In this study, the fingerprint of WDD was established by HPLC, and a total of 23 common peaks were found and seven common peaks were determined. The similarity (R) between 10 batches of WDD fingerprints and reference fingerprints was greater than 0.993. The results of methodological verification met the requirements.

Conclusion: Based on the three dimensions of qualitative analysis, fingerprint, and content determination, this study explored the quality control of WDD and selected seven flavonoids as quality evaluation indexes of WDD, thus laying a solid foundation for subsequent pharmacodynamic research.

Introduction: Diterpene lactones in Andrographis paniculata are essential bioactive compounds that contribute to the herb's medicinal properties. The main diterpene lactones in A. paniculata are andrographolide and its derivatives. Spontaneous degradation of the diterpene leads to a short-term stability and casts a significant problem in storage and distribution of A. paniculata raw materials and products.

Objective: To determine the stability of diterpene lactones in A. paniculata extracts and their transformation dynamics.

Materials and methods: A ¹H NMR-based metabolomics workflow and HPLC-based quantitative determination were used to map the stability profiles in A. paniculata extract stored in the standard storage conditions over a 6-month period.

Results: Qualitatively, NMR-based PCA detected both descending and ascending dynamics in transformation of diterpene lactones in A. paniculata extracts over a 6-month storage period. The contents of five lactone markers, compounds 1-5, in storage A. paniculata extracts were monitored to show that compounds 1 and 5 degraded with decelatory rates and presumably transformed via dehydration into compound 3, which otherwise increased also in a coherently decelatory manner. Lacking of the labile allylic hydroxyl group, compounds 2 and 4 were more stable and remained unchanged throughout the storage period.

Conclusion: The short-term stability of A. paniculata extracts and related products was primarily attributed to the dehydration of 1 and it allylic hydroxy analogs, for example, 5, into a diene as in 3. Compound 3 is hence recommended as a plausible candidate as the stability and age marker of A. paniculata raw materials and products.

Introduction: Antimicrobial resistance is a global public health problem that requires the development of new bioactive compounds. In this context, metabolomic analyses can expedite the research of fungal metabolites as a valuable resource.

Objectives: To investigate the metabolic profiles and isolate antibacterial compounds from micromycetes associated with Mexican cloud forest ants by utilizing network analysis of their chemical and bioactivity data.

Material and methods: 248 fungal strains isolated from six ant's species, soil of their anthills, and soil of the surroundings were evaluated for their in vitro inhibition growth of extensively drug-resistant Acinetobacter baumannii and hypervirulent Klebsiella pneumoniae; subsequently, their metabolites were dereplicated and analyzed by molecular networking and compound activity mapping from spectrometric data. Prioritization of some fungi for isolation of their major constituents was performed, and their structures were established by spectroscopic and spectrometric analysis and their bioactivity determined.

Results: From the fungal collection, 15 secondary metabolites (1-15) were dereplicated, and 10 compounds (16-25), including the new (E)-tridec-7-ene-3,5,6,10-tetraol (25), were isolated from Ascomycetes of Trichoderma, Cladosporium, and Clonostachys genera. Compounds 16-18 stood out for being bioactive. This study is the first report of antibacterial activity against A. baumannii for the tricyclic pyridin-2-ones deoxy-PF1140 (16) and PF1140 (17), with minimum inhibitory concentration of 50 μg/mL.

Conclusion: Network analysis and dereplication proved effective in bioprospecting for antibacterial compounds, offering valuable insights into the chemical diversity of cloud forest soil fungi and their potential applications. Moreover, this study broadens the knowledge of fungal secondary metabolites linked to leafcutter, fire, and warrior ants.

Introduction: Vitex L. is a large genus of tropical and subtropical trees used in medicine of many nations. Some species are used in gynecology due to flavonoids, iridoids, and diterpenes. Other species were shown to contain ecdysteroids and are used as tonic remedies.

Objective: This study aimed to investigate content and patterns of distribution of ecdysteroids in native trees and their accumulation in in vitro cell cultures as potential biotechnological agents of Vitex species growing in remote flora of Russia and Vietnam.

Methodology: Targeted UPLC-MS/MS was used for the quantitation of the ecdysteroids in samples of plants and callus cultures of Vitex species. Determination of nucleotide sequences was carried out on ABI PRISM 3730xl sequencer. Phylogenetic tree was constructed using Mega v.7.0.

Results: Samples of Vitex agnus-castus L. from Russian Black Sea coast of the Caucasus, as well as samples of nine species of Vitex from Vietnam were collected for ecdysteroids quantification. Relationships between the content of ecdysteroids and the systematic position of the Vitex species were shown.

Conclusions: Higher levels of ecdysteroids were revealed in different plant parts of Vitex canescens Kurz, Vitex pinnata L., Vitex quinata (Lour.) F.N.Williams, and Vitex tripinnata (Lour.) Merr. It has been established that species rich in ecdysteroids, as well as those containing trace amount of ecdysteroids (V. agnus-castus L., Vitex negundo L., and Vitex rotundifolia L.f.) are grouped in certain clades isolated from each other on the molecular phylogenetic tree of the genus. The most promising raw materials are the young leaves of V. tripinnata (8562 μg/g of dry biomass), as well as the bark of V. canescens (16,520 μg/g) and V. quinata (19,130 μg/g). The bark of V. canescens could be a good source of turkesterone (11α-oxyecdysteroid) that has pronounced pharmacological effects. Its content reaches up to 1400 μg/g in the bark. Discovering ability of callus cultures for synthesis of ecdysteroids allows us to outline experimental ways to increase the level of ecdysteroid biosynthesis in biotechnological systems as alternative source of ecdysteroids.

Introduction: Peels are an abundant but still underutilized waste product in the Citrus fruit industry. They contain coumarins with antiadipogenic potential that could be promising targets in new valorization strategies for Citrus peels.

Objectives: In this study, these coumarins, that is, citropten, bergamottin, and 5-geranyloxy-7-methoxycoumarin (5G7MC), were investigated in Citrus limon peels of different commercial varieties by HPLC-DAD after extraction with ethanol and choline chloride-based natural deep eutectic solvents (NADES) as alternative extraction agents in green natural product extraction.

Results: Target coumarins were almost exclusively found in the flavedo (exocarp) peel layer and in whole peel samples, but not in the albedo (mesocarp) layer. Flavedo samples from varieties "Verdelli" (ES) and "Lisbon" (ZA) showed particularly high concentrations in ethanolic extracts. When applying NADES extraction, best results for citropten were achieved with malonic acid, 1,2-propanediol, and citric acid as hydrogen bond donors (HBDs), with higher yields than the reference solvent ethanol. For bergamottin and 5G7MC, promising results were obtained for 1,2-propanediol as HBD, though lower yields than with ethanol. The possible chlorination of coumarin epoxides byakangelicol and oxypeucedanin was recognized for acidic NADES in LC-MS analysis.

Conclusion: Overall, C. limon peels proved to be a relevant starting material for valorization through coumarin extraction with ethanol and NADES.

Objective: This study aimed to qualitatively study the main chemical components of apple peel in APORT, Kazakhstan, by ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) and to compare the components of apple peels with different provenances.

Methods: An ACQUITY UPLC HSS T3 (100 mm × 2.1 mm, 1.8 μm) column was used with 0.1% formic acid water (A)-acetonitrile (B) as the mobile phase and gradient elution at a flow rate of 0.2 mL/min and a column temperature of 40°C. Mass spectrometry analysis was performed using the ESI positive and negative ion modes to acquire the data.

Results: With the Mass Lynx 4.2 workstation, online database, retention time of chromatographic peaks of each compound, and secondary fragmentation law, 14 compounds were identified from APORT apple peel extraction samples for the first time, and the main component categories included flavonols, organic acids, dihydrochalcones, terpenes, flavanols, etc., and caffeic acid, crataegolic acid, quinine acid, and quercitrin were found to be unique in APORT apple peel.

Introduction: Cistanche deserticola Ma (CD), an edible and medicinal plant native to Xinjiang, Inner Mongolia, and Gansu in China, is rich in bioactive polysaccharides known for their health-promoting properties. The polysaccharides of C. deserticola (CDPs) have been shown to possess a range of beneficial activities, including immunomodulatory, anti-aging, antioxidant, and anti-osteoporosis effects.

Objective: This study seeks to identify the optimal conditions for extracting CDPs using hot water. Additionally, it aims to evaluate their chemical properties, antioxidant activity, hypoglycemic effects, and cytotoxicity. The findings will provide a theoretical foundation for the potential use of CDPs in functional foods and pharmaceuticals.

Methodology: The study employed response surface methodology to optimize the hot water extraction conditions for CDPs. The extracted CDPs were characterized using a range of chemical, spectroscopic, and instrumental analyses. Furthermore, their antioxidant activity, hypoglycemic effects, and cytotoxicity were evaluated through relevant assays to assess their potential health benefits.

Results: Under optimal conditions, the yield of CDPs was 45.85% ± 1.91%. CDPs were identified as acidic heteropolysaccharides with a wide molecular weight distribution, ranging from 0.3 to 128.2 kDa. They were composed primarily of glucose (51.21%), arabinose (32.86%), galactose (17.88%), and smaller amounts of galacturonic acid (4.66%), rhamnose (1.85%), mannose (1.32%), glucosamine hydrochloride (1.08%), and xylose (0.56%). Antioxidant assays demonstrated that CDPs exhibited significant free radical scavenging activity, metal ion chelation, and reducing power. Additionally, CDPs inhibited α-glucosidase and α-amylase in vitro through a mixed-type mechanism, as well as static fluorescence quenching. Cytotoxicity assays showed that CDPs were nontoxic to L02 and AML12 cells.

Conclusion: This study offers a theoretical foundation for the potential use of CDPs in functional foods and pharmaceuticals and provides valuable insights for the development of new antioxidant and hypoglycemic agents from natural sources.

Introduction: Black rice (Oryza sativa L.) has gained prominence as a functional food because of its rich content of anthocyanins and polyphenols, offering potential health benefits. However, comprehensive research addressing the diverse anthocyanin compositions in black rice cultivars remains limited.

Objective: This study aimed to quantify anthocyanin contents, specifically kuromanin, cyanidin-3-glucoside, peonidin-3-O-glucoside, peonidin-3-glucoside chloride, and cyanidin-3-rutinoside chloride, in 150 rice varieties sourced from the North Eastern Region of India using a robust high-performance thin-layer chromatography (HPTLC) method.

Materials and methods: Rice grains of varying colors-black, orange-reddish, and white-were subjected to methanol extraction under dark conditions through cold maceration for 72 h. The resulting extracts underwent separation on HPTLC silica gel 60 F₂₅₄ plates utilizing an optimized mobile phase of ethyl acetate, 2-butanol, formic acid, and water (9:6:3:3::v/v/v/v).

Results: Anthocyanins were found to be present, and they were most visible in white light compared with UV light at 254 and 366 nm. They were analyzed via densitometry under white light illumination in transmission mode following development. Notably, anthocyanins were absent in grains of white and orange-reddish rice varieties, except for specific lines of Joha (JN 71, JN 83, JN 77, and JN 78) and all black rice variants. Among these, BR 15 exhibited the highest kuromanin content (74.14 ± 0.82 μg/mg), while BR8 showcased the highest peonidin-3-glucoside chloride concentration (27.59 ± 0.83 μg/mg).

Conclusion: This comprehensive analysis provides detailed insights into the anthocyanin compositions of 15 significant black rice cultivars, offering crucial data for breeding programs targeting enhanced anthocyanin-rich cultivars and the development of functional foods.