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1.
Chem Biodivers ; 2020 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-32141193

RESUMO

Fifteen constituents, include one new lignan (schisandroside E, 1) and one new terpenoid (schisandenoid A, 2) as well as nine known lignans and four known terpenoids, were isolated from Schisandra chinensis leaves. The structures of compounds 1-2 were established by entirely meticulous spectroscopic analysis (NMR, MS, CD, IR and UV). All compounds were tested for cytotoxicity against MGC-803, Caco-2 and Ishikawa cell lines. Some compounds showed strong cytotoxicity against these three cancer cell lines with IC50﹤1 µM.

2.
Molecules ; 25(6)2020 Mar 11.
Artigo em Inglês | MEDLINE | ID: mdl-32168752

RESUMO

Withanolides from six parts (flower, leaf, stem, root, seed, and peel) of Datura metel L. (D metel L.) obtained from ten production areas in China were identified and quantified by UPLC-MS/MS. A total of 85 withanolides were characterized for the first time using the UPLC-Q-TOF-MS/MS system. Additionally, a simultaneous, rapid and accurate measurement method was developed for the determination of 22 bioactive withanolides from ten production areas with the UPLC-Q-TRAP-MS/MS system. The results show the total withanolide content is highest in the leaves (155640.0 ng/g) and lowest in the roots (14839.8 ng/g). Compared with other production areas, the total content of plants from Dujiangyan was the highest at 82013.9 ng/g (value range of ten areas: 82013.9-42278.5 ng/g). The results also show significant differences in the distribution of withanolides in the different plant parts, as well as across different production areas. This is a breakthrough report providing a simultaneous qualitative and quantitative analysis of 22 withanolides in D. metel L. It could be the basis for the more rational use of various parts of D. metel L., and the expansion of medicinal resources. This work also lays a solid foundation for research on the quality control of D. metel L.

3.
Fitoterapia ; 142: 104531, 2020 Feb 28.
Artigo em Inglês | MEDLINE | ID: mdl-32114039

RESUMO

Nine new (1-9) and three known (10-12) sesquiterpenoids were isolated from the ethanol-water (7:3, v/v) extract of the Datura metel L. leaves. The structures of 1-9 were elucidated by detailed spectroscopic analyses, including 1D and 2D NMR, HR-ESI-MS. All isolates (1-12) were evaluated for anti-inflammatory activity against the production of nitrogen oxide in lipopolysaccharide-induced RAW264.7 cells and compound 5 possessed the best inhibitory effect among them, with the IC50 value reaching 9.33-11.67 µM, which was lower than positive control, L-NMMA, with IC50 range from 13.64 to 17.02 µM.

4.
Int J Biol Macromol ; 151: 932-943, 2020 Feb 20.
Artigo em Inglês | MEDLINE | ID: mdl-32088239

RESUMO

In this paper, a sequential gas-liquid chromatography and mass spectrometry route was proposed for characterization of polysaccharides in Panax ginseng (PG), P. notoginseng (PN), and P. quinquefolius (PQ). Due to the reflection of stepped structure parameters, the resulting integrative profiles were tentatively defined as structural-fingerprinting of polysaccharides (SFP) with monosaccharide compositional fingerprinting (MCF), Smith degradation and non-degradation fingerprinting (SDF and SNF), and oligosaccharide compositional fingerprinting (OCF). The MCF, OCF and SDF did not allow for visual discrimination of the three species due to the high interspecific similarity of PG and PQ, whereas SNF could intuitively distinguish PG, PN, and PQ by the presence or absence of Rha and the peak area ratio of Glc/Gal. Similarity analysis, heatmap analysis and principal component analysis were further performed to discern three Panax species based on SNF data sets. The linear →4)-Hexp-(1 â†’ structures were clearly identified as the common structural backbones in side chains or smooth regions of the main chain in PPG, PPN, and PPQ using HILIC-UHPLC-ESI--MS/MS for characterization of partial acid hydrolyzates. The experimental results displayed that the established SFP approach possesses high comprehensibility as well as satisfactory generalization capability for analysis of plant polysaccharides.

5.
Fitoterapia ; 142: 104517, 2020 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-32070772

RESUMO

Eight new sesquiterpenoids named melongenaterpenes M-T (1-8), together with nine known compounds (9-17), were isolated from the 70% ethanol extract of the sepals of Solanum melongena L. The structures of all isolated compounds were elucidated based on 1D and 2D NMR spectra and a comprehensive comparison of their spectroscopic and physical data with values from the published literatures. Meanwhile, the cytotoxicity of all the isolated compounds was evaluated on the three human cancer lines of Hela, Ishikawa and MGC-803 by CCK8 assay, respectively.

6.
Chem Biodivers ; 17(3): e1900697, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31943772

RESUMO

A new isoalloxazine alkaloid, named bupleurine A (1), along with five known compounds (2-6), were isolated from the aerial parts of Bupleurum chinense DC. The structure elucidation of the new alkaloid (1) was employed by combining NMR and HR-MS data with comparison of reference in the literature. Five known compounds (2-6) were isolated from Bupleurum genus for the first time. Additionally, their antiproliferative activities on HeLa cells were evaluated by MTT assay and IC50 of compounds 1 and 4-6 were below 10 µm after treatment for 24 h.

7.
Nat Prod Res ; : 1-9, 2020 Jan 17.
Artigo em Inglês | MEDLINE | ID: mdl-31951465

RESUMO

Two new alkaloids named Melongenamides H-I (1-2), together with twenty-one known compounds (3-23), were isolated from the 70% ethanol extract of the sepals of Solanum melongena L. The structures of all isolated compounds were determined by 1D and 2D NMR spectra and by comparing their spectroscopic and physical data with values from the published literatures. All the isolated compounds were evaluated the cytotoxicity against three human canner lines (Hela, Ishikawa and MGC-803) by CCK8 assay.

8.
Int J Biol Macromol ; 147: 350-362, 2020 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-31923501

RESUMO

Two pectin-polysaccharides, ASP-B2 (Mw, 5.32 kDa) and B3 (Mw, 30.51 kDa), were obtained from Acanthopanax senticosus leaves. An HILIC-UPLC-ESI--HCD-MS/MS technique was introduced for structural elucidations of skeletal structure of pectin-polysaccharides in addition to empolying SEC-MALLS, GC-MS, UPLC-ESI+-MS, methylation analysis, FT-IR and NMR methods. Skeletal structure of ASP-B2 was characterized by combining HG smooth region and RG hairy region with a 2:1 chain length ratio, wheres ASP-B3 had a distinguishing 3:1 chain length ratio (HG:RG). HG were defined as repeated →4GalA1→, and RG were featured by repeated →4GalA1 â†’ 2Rhap1 â†’ with branched points at C-3, C-4 and C-3,4 of rhamnosyl. Side chains mainly consisted of galactans, arabinans and arabinogalactans. Both showed a random coil conformation and no triple-helix conformation. ASP-B2 and B3 possess stronger DPPH and hydroxyl radical scavenging activities, with a relatively low reducing power. Thus, two polysaccharides can be further explored as novel natural antioxidant.

9.
Steroids ; 156: 108583, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-31982422

RESUMO

Five undescribed ergostane-type C28 sterols, daturmetesides A-E (1-5), were isolated from the leaves of Datura metel L. The chemical structures of these new compounds were characterized through extensive spectroscopic analysis and comparison with literatures. Among them, the absolute structures of daturmetesides A and C were unambiguously determined by X-ray crystallography. The anti-inflammatory effect of daturmetesides A-E was all tested by measuring nitric oxide production in lipopolysaccharide-activated RAW264.7 cells. Daturmetesides A, C and D moderatelylowered the NO production with IC50 values ranging from 17.05 ± 0.35 to 24.88 ± 0.93 µM.

10.
J Asian Nat Prod Res ; 22(3): 257-263, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30663894

RESUMO

Two new steroids meteloside F (1) and meteloside G (2), together with six known ones (3-8), were isolated and identified from the seeds of Datura metel L. The chemical constituents were isolated by silica gel, ODS chromatogram columns. and preparative HPLC. The structures of these compounds were established by one- and two-dimensional NMR spectra and HR-ESI-MS. The compounds exhibited inhibition on the nitric oxide release of lipopolysaccharide-induced RAW 264.7 cells with IC50 values from 30.2 to 44.8 µM. [Formula: see text].


Assuntos
Datura metel , Animais , Lipopolissacarídeos , Camundongos , Estrutura Molecular , Sementes , Esteroides
11.
Nat Prod Res ; 34(3): 359-368, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30600708

RESUMO

Phytochemical investigation of the roots of Solanum melongena L. resulted in the isolation of ten terpenes and sixteen lignans, including a new triterpene saponin, officinoterpenoside E (1) and twenty-five known compounds (2-26). All compounds were firstly isolated from S. melongena except 2, 13, 21, 22. The structures of these compounds were determined by 1 D and 2 D NMR spectra referring to the literatures, together with high-resolution mass spectrometric analysis. All compounds were evaluated for the cytotoxicity against three cancer cell lines (HepG2, Hela, and MCF-7) in vitro. The results showed that compounds 1, 6, 20, 25 and 26 exhibited moderate cytotoxicity against HepG2, Hela and MCF-7 cells with IC50 values in the range of 16.8 ± 1.7 to 29.1 ± 1.9 µM. Therefore, these terpenoids and lignans may have potential biological activity, and also seemed to be of great chemotaxonomic value for S. melongena.

12.
Fitoterapia ; 141: 104468, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31887326

RESUMO

Thirteen new withanolide aglycones, baimantuoluolines L-X (1-13) and one new withanolide glycoside, baimantuoluoside J (14) were isolated from Datura metel L. flowers. The structures of the new compounds were elucidated by the detailed analysis of 1D and 2D NMR techniques and mass spectrometry, together with the closely related literatures. Meanwhile, all isolated compounds were evaluated for their immunosuppressive activities against mice splenocyte proliferation and antiproliferative activities against human gastric adenocarcinoma cells (SGC-7901), human hepatoma (HepG2), and human breast cancer (MCF-7) in vitro. It was found that compounds 1-14 showed obvious immunosupressive effects and some of them have moderated antiproliferative activities.

13.
J Pharm Biomed Anal ; 178: 112898, 2020 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-31606564

RESUMO

A generic strategy based on chemical fingerprinting is proposed for the differentiation of polysaccharides from Astragalus membranaceus (AEP) and A. mongholicus (AOP), using multiple chromatographic and mass spectrometric techniques. Complete and mild acid hydrolysis and Smith degradation were employed for the depolymerization of polysaccharides. The corresponding digested products were efficiently separated and detected using GC-MS, HILIC-ELSD and HR-ESI--MS. The resulting bottom-up fingerprinting reflected the variations in native polysaccharides, which may be attributed to the three structural levels, which are monosaccharide compositions, glycosidic linkages, and skeletal structure. Similarity analysis from GC-MS and HILIC-ELSD fingerprinting showed that the correlation coefficients from homologous species were more than 0.914, whereas those from heterologous species were less than 0.796. It also noted that characteristic peak area ratio of Man/Gal in Smith fingerprinting could be used a feasible parameter for direct discrimination of AEP and AOP. Principal component analysis from m/z fingerprinting data resulted in clear clustering of AEP and AOP based on changes of oligosaccharides in mild acid hydrolyzates. By combining the accurate m/z, ESI--MS/MS and methylation assays, the structures of a series of hexose glycopolymers in mild acid hydrolyzates were characterized by predominant 1,6 glycosidic linkages along with minor 1,4 glycosidic linkages. The established chemical fingerprinting is not only an interconnected structure mapping but also a powerful approach for the evaluation of polysaccharides from traditional Chinese medicines.

14.
J Nat Prod ; 82(12): 3242-3248, 2019 Dec 27.
Artigo em Inglês | MEDLINE | ID: mdl-31742403

RESUMO

Melongenaterpenes A-L (1-12), 12 new sesquiterpenoids with rare spiro[4.5]decane skeletons, were isolated from the roots of Solanum melongena. Their 2D structures and relative configurations were determined based on NMR and HRESIMS data. The absolute configuration of melongenaterpene A (1) was defined by X-ray crystallographic analysis. The absolute configurations of the remaining compounds were determined by comparison of their NMR data with 1 and consideration of the biosynthetic pathway. This is the first report of the crystal structure of a vetispirane-type sesquiterpenoid. None of the compounds exhibited cytotoxic activity against the three human cancer cell lines HepG2, HeLa, and MCF-7.

15.
J Sep Sci ; 42(22): 3403-3412, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31513345

RESUMO

A simple and sensitive analysis using ultra high performance liquid chromatography with a tandem mass spectrometric system operated in selected reaction monitoring mode was developed for the determination of 11 phenolic acids, atractyloside, and carboxyatractyloside in rat plasma. The two classes of analytes were then separated on a Waters ACQUITY™ UPLC HSS T3 column (50 mm × 2.1 mm, 1.8 µm) using gradient elution with a mobile phase of 0.2% formic acid in water containing 10 mM ammonium acetate and methanol. Detection was accomplished by selected reaction monitoring scanning via an electrospray source operating in negative ionization mode. The calibration curve was linear (R2  = 0.990) over a concentration range of 1.20-3500 ng/mL, while the validated lower limit of quantification was 1.20 ng/mL. The precision varied from 0.84 to 4.62%, and the accuracy varied within ±5%. The method proved robust with sample freezing and thawing and with short- and long-term sample storage. The established method was used for simultaneous quantification and was successfully used for the first time for the pharmacokinetic evaluation of 13 compounds after the intragastric administration of raw and processed Fructus Xanthii in rats. The results indicated that processing affects the absorption and metabolism of Fructus Xanthii extract. Importantly, the results also indicated the importance of processing for the clinical application of traditional Chinese medicine.

16.
J Asian Nat Prod Res ; : 1-13, 2019 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-31496278

RESUMO

A UPLC-MS/MS method was developed and validated the determination and pharmacokinetic study of magnoflorine, cauloside C, hederagenin, and oleanolic acid from Caulophyllum robustum. Digoxin was used as the internal standard. The pretreated plasma samples were carried out on a Waters ACQUITYUPLC HSS T3 column at 35 °C with a mobile phase of acetonitrile-water (90:10, v/v) at a flow rate of 0.2 mL/min. This article describes the most simple, sensitive, and validated UPLC-MS/MS method to date for the simultaneous successful determination of four compounds in rat plasma after oral administration of the extract of C. robustum and their pharmacokinetic studies.

17.
Int J Biol Macromol ; 137: 1232-1244, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31295497

RESUMO

Auricularia auricular-judae polysaccharides (AAPs) have been accepted as one important biological constituent. Quality analysis of A. auricular-judae is generally difficult due to technical issues in separating and detecting AAPs. Here, we describe a stepped chromatographic and mass spectrometric approach for discrimination and characterization of AAPs. HPSEC-MALLS-RID and GC-MS techniques have earlier been shown to be ineffective in evaluating wild and cultured AAPs based on molecular weight distributions and monosaccharide compositions. Nevertheless, direct ESI--MS oligosaccharide fingerprints coupled with PCA have the remarkable ability to discriminate wild and cultured ones. HILIC-UPLC-ESI--MS has indicated that wild and cultured AAPs have distinct peak number and intensities in mild acid hydrolysates. HILIC-UPLC-ESI--HCD-MS/MS was further applied in deducing interglycosidic linkages and sequence of monosaccharide residues in oligosaccharides. We demonstrate that linear GlcAw → Hexm → GlcAx → Hexn → GlcAy → Hexp → GlcAz → Hexq → (w, x, y, z = 0, 1; m, n, p, q ≥ 0; Hex1 → 6Hex, GlcA1 → 4Hex, Hex1 → 4GlcA) was constructed as the general skeleton of AAPs based on C- and B-type ions as well as cross-ring cleavage A-type series ions. The established workflow has been confirmed to be a feasible approach for comprehensive characterization of polysaccharides in foods and plants.


Assuntos
Basidiomycota/química , Carpóforos/química , Polissacarídeos Fúngicos/química , Basidiomycota/crescimento & desenvolvimento , Sequência de Carboidratos , Cromatografia Líquida de Alta Pressão , Polissacarídeos Fúngicos/isolamento & purificação , Hidrólise , Espectrometria de Massas , Metilação , Peso Molecular
18.
Chin J Nat Med ; 17(6): 401-412, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31262453

RESUMO

Atherosclerosis (AS) is a chronic inflammatory disease associated with high morbidity and mortality. The incidence of AS is increasing in the last decades. So development of safe and effective therapeutics for treating AS has become prominently important. Although there are numerous chemical drugs available for treating AS, some drugs are not effective and some have serious side effects. Traditional Chinese medicine (TCM) has a long history for the prevention and treatment of AS due to its less side effects and superior efficacy. This paper describes the effectiveness and underlying mechanisms for prevention and treatment of AS by TCM or its active components. Some TCM, e.g. XuemaiNing, Tongxinluo and Salvia miltiorrhiza have been reported to have cardio-protective effect. Some active components of TCM, e.g. saikosaponin-A, kuwanon G, luteolin and ß-elemene have been isolated from various TCM and demonstrated to have beneficial effects on prevention and treatment of AS.


Assuntos
Aterosclerose/tratamento farmacológico , Medicamentos de Ervas Chinesas/uso terapêutico , Animais , Aterosclerose/prevenção & controle , Humanos , Medicina Tradicional Chinesa , Plantas Medicinais/química
19.
J Nat Med ; 73(4): 800-804, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31177356

RESUMO

A new triterpene named klodorol B (1), together with six known compounds, were isolated from the green walnut husks of Juglans mandshurica Maxim. Their structures were determined using spectroscopic methods on the basis of 1D and 2D NMR, and high-resolution electrospray ionization mass spectrometry. The isolated compounds were evaluated for their cytotoxic activities on human gastric carcinoma (BGC-823), human liver cancer (HepG-2) and human lung cancer (A549) cell lines. .


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Juglans/química , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Pulmonares/tratamento farmacológico , Extratos Vegetais/farmacologia , Neoplasias Gástricas/tratamento farmacológico , Triterpenos/farmacologia , Células A549 , Linhagem Celular Tumoral , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Nozes/química , Triterpenos/análise
20.
Molecules ; 24(11)2019 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-31181689

RESUMO

BACKGROUND: Psoriasis is a chronic, immune-mediated inflammatory skin disease, and the inflammatory response plays an important role in its development and progression. Datura metel L. is a traditional Chinese medicine that exhibited a significant therapeutic effect on psoriasis in our previous study due to its remarkable anti-inflammatory effect. Meanwhile, the mechanism underlying its effects on psoriasis is still unclear. METHODS: An imiquimod-induced psoriasis-like dermatitis mouse model was constructed to evaluate the protective effect of the effective part of Datura metel L. (EPD), which was verified by evaluations of the Psoriasis Area and Severity Index (PASI) score. Hematoxylin and eosin (H&E) staining, immunohistochemical examination, enzyme-linked immunosorbent assay (ELISA), and Western blot were used to measure the inflammatory cytokines and the protein expression associated with the Toll-like receptor 7- myeloid differentiation primary response gene 88-nuclear Factor-κB-nucleotide-binding oligomerization domain (Nod)-like receptor family pyrin domain-containing 3 (TLR7/8-MyD88-NF-κB-NLRP3) inflammasome pathway. RESULTS: EPD significantly decreased the PASI, reduced epidermal thickness, and decreased the proliferation and differentiation of epidermal cells in psoriasis-like dermatitis C57BL/6 mice induced by imiquimod (IMQ). Furthermore, EPD reduced the infiltration of CD3+ cells to psoriatic lesions, as well as ameliorated the elevations of intercellular adhesion molecule 1 (ICAM-1) and inhibited the production of imiquimod-induced inflammatory cytokines, including IL-1ß, IL-2, IL-6, IL-10, IL-12, IL-17, IL-22, IL-23, tumor necrosis factor-α (TNF-α), monocyte chemotactic protein 1 (MCP-1), and interferon-γ (IFN-γ). Besides, EPD decreased the imiquimod-induced expression levels of TLR7, TLR8, TRAF6, MyD88, p-IKKα, p-IKBα, p-NF-κB, NLRP3, apoptosis-associated speck-like protein contained a caspase recruitment domain (ASC), cysteinyl aspartate specific proteinase 1 (caspase-1), and IL-1ß. CONCLUSION: This study demonstrated that EPD exhibited a protective effect on an imiquimod-induced psoriasis mice model by inhibiting the inflammatory response, which might be ascribed to the inhibition of the TLR7/8-MyD88-NF-κb-NLRP3 inflammasome pathway.


Assuntos
Citocinas/metabolismo , Datura metel/química , Medicamentos de Ervas Chinesas/administração & dosagem , Imiquimode/efeitos adversos , Psoríase/tratamento farmacológico , Transdução de Sinais/efeitos dos fármacos , Animais , Modelos Animais de Doenças , Regulação para Baixo , Medicamentos de Ervas Chinesas/farmacologia , Regulação da Expressão Gênica/efeitos dos fármacos , Masculino , Glicoproteínas de Membrana/metabolismo , Camundongos , Fator 88 de Diferenciação Mieloide/metabolismo , NF-kappa B/metabolismo , Proteína 3 que Contém Domínio de Pirina da Família NLR/metabolismo , Psoríase/induzido quimicamente , Psoríase/imunologia , Receptor 7 Toll-Like/metabolismo , Receptor 8 Toll-Like/metabolismo
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