ABSTRACT
Eight previously undescribed cevanine-type steroidal alkaloids, cirrhosinones I-N and cirrhosinols A-B, along with five known analogs, were isolated from the bulbs of Fritillaria cirrhosa D. Don. Their structures were elucidated on the basis of comprehensive analysis of HRESIMS, 1D and 2D NMR spectroscopic data, and single-crystal X-ray diffraction analyses. All compounds revealed weak NO inhibitory activities in the LPS-stimulated NR8383 cells at the concentration of 20 µM, with inhibition ratios ranging from 5.1% to 14.3%.
Subject(s)
Alkaloids , Fritillaria , Plant Roots , Fritillaria/chemistry , Plant Roots/chemistry , Molecular Structure , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Cevanes/chemistry , Cevanes/pharmacology , Cevanes/isolation & purification , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Lipopolysaccharides/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Animals , Molecular Conformation , Crystallography, X-Ray , Cell Line , Rats , Steroids/chemistry , Steroids/isolation & purification , Steroids/pharmacology , Dose-Response Relationship, Drug , Structure-Activity Relationship , Models, MolecularABSTRACT
An unprescribed nortriterpenoid with an aromatic E ring, uncanortriterpenoid A (1), together with fourteen known triterpenoids (2-15), were isolated from the hook-bearing stems of Uncaria rhynchophylla Miq. Based on extensive spectroscopic analyses, the NMR data of 2, 5, and 10 in CD3OD were assigned for the first time, and the wrongly assigned δC of C-27 and C-29 of 2 were revised. Among the known compounds, 7, 13, and 15 were isolated from this species for the first time, and 15 represents the first lanostane triterpenoid bearing an extra methylidene at C-24 for the Rubiaceae family. Additionally, compounds 6 and 14 exhibited moderate ferroptosis inhibitory activity, with an EC50 value of 14.74 ± 0.20 µM for 6 and 23.11 ± 1.31 µM for 14.
Subject(s)
Plant Stems , Triterpenes , Uncaria , Uncaria/chemistry , Triterpenes/chemistry , Triterpenes/pharmacology , Triterpenes/isolation & purification , Plant Stems/chemistry , Molecular Structure , HumansABSTRACT
IR spectroelectrochemistry (EC-IR) is a cutting-edge operando method for exploring electrochemical reaction mechanisms. However, detection of interfacial molecules is challenged by the limited sensitivity of existing EC-IR platforms due to the lack of high-enhancement substrates. Here, we propose an innovative plasmon-enhanced infrared spectroelectrochemistry (EC-PEIRS) platform to overcome this sensitivity limitation. Plasmonic antennae with ultrahigh IR signal enhancement are electrically connected via monolayer graphene while preserving optical path integrity, serving as both the electrode and IR substrate. The [Fe(CN)6 ]3- /[Fe(CN)6 ]4- redox reaction and electrochemical CO2 reduction reaction (CO2 RR) are investigated on the EC-PEIRS platform with a remarkable signal enhancement. Notably, the enhanced IR signals enable a reconstruction of the electrochemical curve of the redox reactions and unveil the CO2 RR mechanism. This study presents a promising technique for boosting the in-depth understanding of interfacial events across diverse applications.
ABSTRACT
Fourteen previously undescribed steroidal alkaloids, including six jervine-type, wabujervine A-E and wabujerside A, seven cevanine-type, wabucevanine A-G, and one secolanidin-type, wabusesolanine A, along with thirteen known steroidal alkaloids, were isolated from the bulbs of Fritillaria unibracteata var. wabuensis. On the basis of comprehensive analysis of IR, HRESIMS, 1D and 2D NMR spectroscopic data, and single-crystal X-ray diffraction analyses, their structures were elucidated. In the zebrafish acute inflammatory models, nine compounds showed anti-inflammatory activity.
Subject(s)
Alkaloids , Fritillaria , Animals , Fritillaria/chemistry , Zebrafish , Alkaloids/chemistry , Anti-Inflammatory Agents/pharmacology , Plant Roots/chemistry , Steroids/chemistryABSTRACT
Nine undescribed steroidal alkaloid glycosides, unibrasolanosides A-F, unibraverazosides A-B, and unibratomatoside A, were isolated from the bulbs of Fritillaria unibracteata P. K. Hsiao & K. C. Hsia (Liliaceae). Their structures were elucidated by HRESIMS and 1D and 2D NMR data analyses as well as chemical methods and single-crystal X-ray diffraction analyses. Further investigation revealed that eight steroidal alkaloid glycosides displayed moderate anti-inflammatory activity in vivo in a CuSO4-induced transgenic zebrafish model.
ABSTRACT
BACKGROUND: Cannabis is an important industrial crop species whose fibre, seeds, flowers and leaves are widely used by humans. The study of cannabinoids extracted from plants has been popular research topic in recent years. China is one of the origins of cannabis and one of the few countries with wild cannabis plants. However, the genetic structure of Chinese cannabis and the degree of adaptive selection remain unclear. RESULTS: The main morphological characteristics of wild cannabis in China were assessed. Based on whole-genome resequencing SNPs, Chinese cannabis could be divided into five groups in terms of geographical source and ecotype: wild accessions growing in the northwestern region; wild accessions growing in the northeastern region; cultivated accessions grown for fibre in the northeastern region; cultivated accessions grown for seed in northwestern region, and cultivated accessions in southwestern region. We further identified genes related to flowering time, seed germination, seed size, embryogenesis, growth, and stress responses selected during the process of cannabis domestication. The expression of flowering-related genes under long-day (LD) and short-day (SD) conditions showed that Chinese cultivated cannabis is adapted to different photoperiods through the regulation of Flowering locus T-like (FT-like) expression. CONCLUSION: This study clarifies the genetic structure of Chinese cannabis and offers valuable genomic resources for cannabis breeding.
Subject(s)
Cannabis , Genome, Plant , Cannabis/genetics , Humans , Phenotype , Plant Breeding , Selection, Genetic , Sequence Analysis, DNAABSTRACT
In light of related methods in Chinese Pharmacopoeia(2020 edition), this study established the quality standard for Lobeliae Chinensis Herba. The TLC identification method was established with silica gel GF_(254) thin layer plate, diosmin standard, linarin standard, and the reference material of Lobeliae Chinensis Herba. The loss on drying, total ash, acid-insoluble ash, and ethanol-soluble extracts of 18 batches of Lobeliae Chinensis Herba samples were determined according to the general principles in Chinese Pharmacopoeia. Then, HPLC was adopted in the establishment of characteristic chromatogram and content determination. The results showed that the established method can achieve good separation for diosmin, linarin, and lobetyolin. Based on the results of detection for 18 batches of Lobeliae Chinensis Herba samples, the draft quality standard was established, which was expected to provide reference for the revision of this medicinal herb in Chinese Pharmacopoeia.
Subject(s)
Drugs, Chinese Herbal , Lobelia/chemistry , Plants, Medicinal , Chromatography, High Pressure Liquid , Drugs, Chinese Herbal/standards , Plants, Medicinal/chemistryABSTRACT
Thirteen steroids(1-13) were isolated from the non-alkaloid constituents of Uncaria rhynchophylla by column chromatography on silica gel, ODS, Sephadex LH-20, and preparative HPLC chromatography, and their structures were elucidated by analyses of the MS and NMR spectral data. All the compounds were isolated from the genus Uncaria for the first time, and 1 was a new compound. The ~1H-NMR and ~(13)C-NMR data of two compounds(12 and 13) in deuteron-chloroform were completely assigned. This study enriched the steroid constituents of U. rhynchophylla and provided scientific references for the elucidation of active constituents and further development and utilization of U. rhynchophylla.
Subject(s)
Uncaria , Chromatography, High Pressure Liquid , Steroids , Uncaria/chemistryABSTRACT
Four p-coumaroylated sesquiterpenoids (1-4), including three new ones (1, 2, and 4), were isolated from the whole plants of Pilea cavaleriei. Their structures were established on the basis of comprehensive spectroscopic analysis and comparison with data reported in the literature. Compounds 1-4 were evaluated for their antimycobacterial activities, and 2 and 4 were active against Mycobacterium tuberculosis H37Rv with the MIC values of 19.6 ± 0.19 and 17.4 ± 0.12 µg/mL, respectively.
Subject(s)
Drugs, Chinese Herbal , Mycobacterium tuberculosis , Sesquiterpenes , Urticaceae , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Drugs, Chinese Herbal/chemistry , Microbial Sensitivity Tests , Sesquiterpenes/chemistry , Urticaceae/chemistryABSTRACT
Seven undescribed condensation derivatives of 4-isopropylbenzaldehyde with acetophenone, including one 1,3,5-trisubstituted pentane-1,5-dione, two 1,3,4,5,7-pentasubstituted heptane-1,7-diones and four 1,2,3,4,5-pentasubstituted cyclohexanols, together with two known flavonoids, were obtained from the red alga Laurencia tristicha. The relative configurations were elucidated by extensive spectroscopic data analysis of MS, 1D and 2D NMR, while the absolute configurations were determined by comparing the experimental and calculated electronic circular dichroism spectra. All the isolates were proven to be naturally occurring in the red alga by LC-MS analysis, and these 1,3,5-trisubstituted-pentane-1,5-dione, 1,3,4,5,7-pentasubstituted-heptane-1,7-diones and 1,2,3,4,5-pentasubstituted-cyclohexanols were reported from natural sources for the first time. The proposed biogenetic pathway of the isolates was also discussed.
Subject(s)
Laurencia , Rhodophyta , Acetophenones , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Longxue Tongluo Capsules(LTC) has good efficacy against blood stasis syndrome during the recovery period of ischemic stroke. Its main active ingredient is the phenolic extract of Chinese dragon's blood. In our previous study, the primary mass fragmentation pathways of phenolic derivatives from LTC were clarified. Herein, the metabolites in rat plasma were characterized following the oral administration of loureirin A and loureirin C using liquid chromatography coupled with hybrid ion trap/time-of-flight mass spectro-metry(LC-IT-TOF-MS), with 18 and 55 metabolites identified, respectively. On this basis, with the help of the obtained accurate molecular weight, characteristic fragment ions, reference comparison, combined with LTC database and natural products database self-created in our group, 18 prototypes and 106 metabolites were tentatively identified in rat plasma after oral gavage of LTC at a dose of 500 mg·kg~(-1). Glucuronidation, sulfonation, and methylation were major biotransformation pathways of LTC. This study preliminarily clarified the LTC constituents absorbed into blood and laid the foundation for clarifying the effective substances of LTC.
Subject(s)
Drugs, Chinese Herbal , Administration, Oral , Animals , Capsules , Chromatography, High Pressure Liquid , Chromatography, Liquid , Gas Chromatography-Mass Spectrometry , RatsABSTRACT
One new cis p-coumaroyl copaborneol-type sesquiterpenoid (1), together with its known trans isomer (2) and six other known p-coumaroyl humulane-type sesquiterpenoids (3-8), were isolated from the whole plants of Pilea cavaleriei. Their structures were determined by spectroscopic data. Compounds 1-4 exhibited moderate antimycobacterial activity against Mycobacterium tuberculosis H37Rv.
Subject(s)
Sesquiterpenes/isolation & purification , Urticaceae/chemistry , Anti-Bacterial Agents/pharmacology , Carbon-13 Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Mycobacterium tuberculosis/drug effects , Proton Magnetic Resonance Spectroscopy , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacologyABSTRACT
Zaoren Anshen prescription preparations(ZRASs), which are prepared from three traditional Chinese herb medicines, namely fried Zizyphi Spinosae Semen, Salvia Miltiorrhizae Radix et Rhizoma and vinegar-processed Schisandrae Chinensis Fructus, are a series of proprietary Chinese medicines for the treatment of insomnia, amnesia and dizzy in clinic. In recent years, pharmacodynamic effect, chemical constituents and quality control of ZRASs had been extensively studied for the purpose of ensuring their safety, efficacy and stability, and a great progress had been made. However, there is no review of the research advance of ZRASs up to date. The present review summarized the research advance of ZRASs in quality control standards, chemical constituents, pharmacodynamic effects, and chemical analysis for the first time, with the aim to provide a reference for further studies on the effective constituents and quality control of ZRASs.
Subject(s)
Drugs, Chinese Herbal , Salvia miltiorrhiza , Drugs, Chinese Herbal/pharmacology , Medicine, Chinese Traditional , Prescriptions , RhizomeABSTRACT
One new laurane-type sesquiterpene, 10-hydroxyepiaplysinol (1), along with two known related sesquiterpenes, epiaplysinol (2) and ar-bisabol-9-en-7,11-diol (3), and one carotenoid metabolite, loliolide (4), were obtained from the red alga Laurencia tristicha. Their structures were elucidated based on comprehensive spectroscopic data analysis. Of the known compounds, 4 was isolated from the genus Laurencia for the first time. Additionally, the antioxidant activities of eleven laurane-type sesquiterpenes from L. tristicha were evaluated.
Subject(s)
Laurencia , Sesquiterpenes , Antioxidants , Molecular Structure , TerpenesABSTRACT
OBJECTIVE: Dietary salt intake may vary depending on different lifestyles. We aimed to estimate the different salt intakes and evaluate the knowledge and self-awareness about salt among people speaking the Teochew, Teochew-Hakka and Hakka dialects in the Chaoshan region of southern China. DESIGN: The study followed a cluster sampling of residents in Chaoshan region. General characteristics, lifestyles, health status as well as knowledge and self-awareness related to salt intake were investigated using a questionnaire. Anthropometric variables as well as Na and K excretion in a 24-h urine collection were measured. SETTING: Chaoshan region of China. PARTICIPANTS: Four hundred fifteen adults who spoke only one of these three dialects. RESULTS: The salt intake of adults who spoke the Teochew, Teochew-Hakka and Hakka dialects was 7·19 (interquartile range (IQR) 5·29-10·17), 9·03 (IQR 6·62-11·54) and 10·12 (IQR 7·61-12·82) g/d, respectively, with significant differences between Teochew and Teochew-Hakka speakers and between Teochew and Hakka speakers (both P < 0·05). The Na:K ratio for adults who spoke the three dialects was 3·00 (IQR 2·00-4·11), 3·50 (IQR 2·64-4·82) and 4·52 (IQR 3·35-5·97), respectively, and differed significantly among the groups (all P < 0·05). Multiple linear regression analysis showed increased Na:K ratio associated with hypertension (ß = 0·71, P = 0·043) in Hakka speakers. Knowledge and self-awareness about salt intake were poor in this population. CONCLUSIONS: Salt intake was closely related to lifestyles and was higher than the upper limit (5 g/d) recommended by the WHO in adults of Chaoshan, especially those speaking the Hakka dialect.
Subject(s)
Feeding Behavior , Sodium Chloride, Dietary , Adult , Awareness , China , Humans , Language , Sodium Chloride, Dietary/administration & dosageABSTRACT
AIMS/INTRODUCTION: Elevated concentrations of fasting plasma glucose (FPG) or hemoglobin A1c (HbA1c) are well-established independent risk factors for progression to diabetes, cardiovascular comorbidities and mortality. Most previous studies on the relationships of anthropometric measures with hyperglycemia were carried out among adults and adolescents, but few data are available for the performance predication of the predictors for diagnosing elevated FPG or HbA1c among young children. MATERIALS AND METHODS: Involving 5,556 students of aged 7-9 years, a school-based cross-sectional survey was carried out between March and June 2019 in Shenzhen, China. Receiver operating characteristic curve analysis was utilized. RESULTS: The median was 4.6 (interquartile range [IQR] 4.3-4.8) mmol/L for FPG and 5.3% (IQR 5.1-5.5%) for HbA1c levels for all participants. For detecting elevated FPG, weight (0.651, IQR 0.583-0.719) and waist circumference (0.650, IQR 0.584-0.717) showed the highest area under the curve and 95% confidence interval, followed by body mass index and the z-score of body mass index (both 0.635, IQR 0.567-0.703); other anthropometric measures showed poorer diagnostic efficiencies or no ability. For detecting elevated HbA1c, lower efficiencies for the Conicity Index (0.651, IQR 0.583-0.719), waist-to-height ratio, waist-to-hip ratio and waist-to-chest ratio were shown. The correlations of FPG and HbA1c levels with anthropometric indices were weak (Spearman's r ≤ 0.179). CONCLUSIONS: None of the evaluated anthropometric indicators approached an adequate predictive accuracy for the detection of elevated FPG or HbA1c levels in Shenzhen children aged 7-9 years. The current study did not recommend anthropometry screening for prediabetes in young children.
Subject(s)
Anthropometry , Blood Glucose/analysis , Glycated Hemoglobin/analysis , Hyperglycemia/diagnosis , Mass Screening/statistics & numerical data , Asian People/statistics & numerical data , Body Mass Index , Child , China , Cross-Sectional Studies , Diabetes Mellitus/diagnosis , Diabetes Mellitus/etiology , Fasting/blood , Female , Humans , Hyperglycemia/complications , Male , Mass Screening/methods , Predictive Value of Tests , ROC Curve , Risk Assessment , Risk Factors , Waist Circumference , Waist-Height RatioABSTRACT
Three pairs of enantiomers mucroniferals A-C (1-3), with a novel skeleton of 1,4-epoxynaphthalene-2,3-dicarboxylic acid first reported from nature source, were isolated from Corydalis mucronifera. Their structures were elucidated based on extensive spectroscopic data analysis of MS, 1D and 2D NMR, and their absolute configurations were confirmed by single-crystal X-ray diffraction analysis and comparison of the experimental and calculated ECD data. Mucroniferals A-C showed broad-spectrum inhibitory activities on seedling growth of all plants tested (Lepidium apetalum, Raphanus sativus, Lactuca sativa, and Arabidopsis thaliana) with a dose-dependent relationship. Additionally, mucroniferals A and B exhibited significant inhibitory effects on germination of most seeds at concentration of 80 µg/mL, and the inhibition was reversible.
Subject(s)
Corydalis/chemistry , Germination/drug effects , Plant Growth Regulators/pharmacology , Seedlings/drug effects , Arabidopsis/drug effects , Lepidium/drug effects , Lactuca/drug effects , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Growth Regulators/isolation & purification , Raphanus/drug effects , TibetABSTRACT
BACKGROUND: and purpose: We investigated the effectiveness of cupping therapy with three different pressures in patients with chronic fatigue syndrome (CFS). MATERIALS AND METHODS: The participants were randomly assigned to three groups, as follows: cupping pressure of -0.02 mpa (n = 38), -0.03 mpa (n = 38), or -0.05 mpa (n = 36). Each group received cupping treatment that consisted of 10 sessions over 5 weeks (2 sessions per week). The primary outcomes were Fatigue Scale (FS-14) score and Fatigue Assessment Instrument (FAI) score after 5 and 10 sessions. The secondary outcomes were the Self-Rating Anxiety Scale (SAS) score, the Self-Rating Depression Scale (SDS) score, and the Pittsburgh Sleep Quality Index (PSQI) score. RESULTS: There were 91 participants who completed the trial. After five sessions of treatment, the primary outcome of FS-14 score decreased by 3.20 (2.19, 4.21) in the -0.02 mpa group, by 2.39 (1.51, 3.27) in the -0.03 mpa group, and by 3.40 (2.28, 4.52) in the -0.05 mpa group (P = 0.667). After 10 sessions of treatment, the outcome of FS-14 score decreased by 5.00 (3.79, 6.21) in the -0.02 mpa group, by 4.06 (3.07, 5.05) in the -0.03 mpa group, and by 4.77 (3.52, 5.94) in the -0.05 mpa group (P = 0.929). And, the results were statistically different between 5 sessions and 10 sessions of treatment (P < 0.01). However, there were no statistical differences in FAI, SAS, SDS, and PSQI scores between the three groups after 5 sessions and 10 sessions of treatment. CONCLUSIONS: In conclusion, cupping therapy has significantly relieved fatigue symptoms and improved emotion and sleep condition of CFS patients, and 10 sessions of treatment had superior results compared with 5 sessions in each group. Moreover, in 5 sessions of treatment, cupping with high pressure showed better improvement in fatigue syndromes and sleep condition according to effective rates. TRIAL REGISTRATION: Chinese clinical trial registry (ChiCTR1800017590); Ethical approval number: ChiECRCT-20180085.
Subject(s)
Cupping Therapy/methods , Fatigue Syndrome, Chronic/therapy , Adult , Female , Humans , Male , Middle Aged , Single-Blind Method , Sleep Wake Disorders/therapy , Young AdultABSTRACT
Six undescribed quinoline alkaloids, named dasycarines A-E, and 18 known ones were isolated from the root bark of Dictamnus dasycarpus. All the structures were elucidated on the basis of comprehensive analysis of UV, IR, NMR, and HRMS spectroscopic data, and the absolute configurations were assigned via comparison of the calculated and experimental ECD data. (+)-Dasycarine A (1a) and (-)-Dasycarine A (1b) are a pair of enantiomers of dimeric furoquinoline alkaloid, which are the first dimeric via [2 + 2] cycloaddition of furan. The structure and absolute configuration of (-)-dasycarine A was determined via X-ray crystallography. Additionally, all the isolated compounds were tested for their inhibitory effects on NO production stimulated by LPS in BV-2 microglial cells. Three compounds showed strong inhibition with IC50 values below 5.0 µM; nine compounds exhibited inhibition with IC50 values in the range of 7.8-28.4 µM. Furthermore, we demonstrated that preskimmianine suppressed the levels of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nuclear factor kappa B (NF-κB) in LPS-induced BV-2 microglial cells.
Subject(s)
Alkaloids , Dictamnus , Quinolines , Anti-Inflammatory Agents , Plant BarkABSTRACT
Three new compounds (1-3), named dasycarine G (1), dasycarether (2), and dasycarester (3), along with seven known compounds (4-10) obtained from the genus Dictamnus for the first time, were isolated from the root bark of Dictamnus dasycarpus. Their structures were elucidated on the basis of spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR, and CD). In the in vitro assay, compounds 1, 5, 6, 9, and 10 exhibited NO inhibitory effects of LPS-induced BV-2 cells with IC50 values in the range of 10.4 µM to 27.2 µM.