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1.
J Nat Med ; 74(1): 142-152, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31463669

RESUMO

Cynandione A (CA), isolated from ethyl acetate extract of Cynanchum wilfordii (CW), is a bioactive phytochemical that has been found to be beneficial for the treatment of several diseases. Hepatic de novo lipogenesis is one of the main causes of non-alcoholic fatty liver disease (NAFLD), which is thought to be a hepatic manifestation of certain metabolic syndromes. However, it has not yet been reported if CA has any therapeutic value in these diseases. Here, we investigated whether CA can inhibit hepatic lipogenesis induced by liver X receptor α (LXRα) using an in vitro model. We found that the extract and ethyl acetated layer of CW decreased the mRNA levels of sterol regulatory element-binding protein-1c (SREBP-1c), which plays a crucial role in hepatic lipogenesis. Additionally, we observed that CA could suppress the level of SREBP-1c, which was increased using two commercial LXRα agonists, GW3954 and T0901317. Moreover, the enzymes that act downstream of SREBP-1c were also inhibited by CA treatment. To understand the mechanism underlying this effect, the levels of phosphorylated AMP kinase (pAMPK) were measured after CA treatment. Therefore, CA might increase the pAMPK level by inducing phosphorylation of liver kinase B1 (LKB1), which can then convert AMPK to pAMPK. Taken together, we conclude that CA has an alleviative effect on hepatic lipogenesis through the stimulation of the LKB1/AMPK pathway.


Assuntos
Proteínas Quinases Ativadas por AMP/metabolismo , Compostos de Bifenilo/farmacologia , Cynanchum/química , Lipogênese/efeitos dos fármacos , Proteínas Serina-Treonina Quinases/metabolismo , Animais , Células Hep G2 , Humanos , Hidrocarbonetos Fluorados/farmacologia , Fígado/efeitos dos fármacos , Receptores X do Fígado/metabolismo , Hepatopatia Gordurosa não Alcoólica/tratamento farmacológico , Fosforilação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Proteína de Ligação a Elemento Regulador de Esterol 1/genética , Sulfonamidas/farmacologia
2.
Zhongguo Zhong Yao Za Zhi ; 44(14): 2960-2965, 2019 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-31602840

RESUMO

The study aimed to investigate the mechanism of hepatoprotective effect of C-21 steroidal glucosides from Cynanchum auriculatum( Baishouwu) on oxidative stress in mice with liver injury. Mice were randomly divided into normal group,model group,positive control group,Baishouwu high group and Baishouwu low group. The liver injury model was induced by intraperitoneal injection of CCl4 peanut oil solution. All mice were sacrificed to collect blood and liver specimens. The activities of serum levels of ALT and AST were detected. The content of MDA and the activity of SOD in liver homogenate were examined by colorimetry method. Tissues were stained with hematoxylin-eosin for histological examination. The hepatic protein expressions of NF-κB p65,p-IκBα,i NOS and COX-2 were detected by Western blot. The mRNA expressions of TNF-α and IL-6 were determined by RT-PCR. It was found that treatment with C-21 steroidal glucosides from Baishouwu successfully attenuated liver injury induced by CCl4,as shown by decreased levels of serum biochemical indicators( AST,ALT)( P<0. 01). Administration of total C-21 steroidal glucosides enhanced the activity of SOD( P<0. 01) and decreased the content of MDA( P<0. 01) in liver homogenate. Microscopic features suggested that treatment with C-21 steroidal glucosides from Baishouwu was effective in inhibiting CCl4-induced hepatocyte edema and degeneration. Further studies showed that NF-κB p65 overexpression induced by CCl4 was decreased by C-21 steroidal glucosides,leading to the markedly down-regulated protein expression levels of p-IκBα,i NOS and COX-2,as well as the depression of TNF-α and IL-6 mRNA expressions. In conclusion,total C-21 steroidal glucosides from Baishouwu exhibited potent effect on oxidative stress pathway in mice with liver injury induced by CCl4,with enhanced activity of SOD,decreased content of MDA,and down-regulated levels of NF-κB p65,p-IκBα,i NOS and COX-2.


Assuntos
Doença Hepática Induzida por Substâncias e Drogas/tratamento farmacológico , Cynanchum/química , Glucosídeos/farmacologia , Estresse Oxidativo , Animais , Tetracloreto de Carbono , Hepatócitos/efeitos dos fármacos , Fígado/efeitos dos fármacos , Camundongos , Distribuição Aleatória
3.
J Food Sci ; 84(10): 2831-2839, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31573691

RESUMO

This study aims to investigate alterations in volatile compounds and chemical components that may affect the sensory properties of Cynanchi wilfordii roasted at 120 °C and 180 °C for various durations of time (0 to 4 min). For volatile compound profiles, tridecane, tetradecane, and ethyl hexyl ether were detected as major compounds of the sample without roasting. As the roasting temperature increased, the types of volatile compounds increased, whereas the content decreased with an increase in heterocyclic compound generation. The sample roasted at 120 °C for 1 min showed a notably different profile pattern from the other roasted samples. For the sniffing test performed by trained panelists using gas chromatography olfactometry, naphthalene and nonanal, which induce spicy and raw C. wilfordii, respectively, were perceived most intensely throughout all the samples. In the electronic tongue analysis, the sample roasting at 180 °C showed an increased and decreased pattern in umami taste and saltiness, respectively, with increased roasting time. Electronic tongue analysis results showed that the sample roasted at 180 °C for 4 min would have the best sensory preference. Along with the volatile compound profiles, the sample roasted at 120 °C for 1 min had more sourness than the other samples, and would potentially have distinctive sensory characteristics. This study should provide baseline data on variations in the sensory properties and industrial applications of C. wilfordii upon roasting. PRACTICAL APPLICATION: Various applications of food ingredients through changes in sensory characteristics by roasting will provide consumers more options for food selections. Accordingly, this study will be utilized by (1) individuals and food companies who are interested in functional foods, (2) individuals and food industries that seek optimum roasting conditions for proper sensory characteristics of foods, and (3) farmers and crop producers who seek for utilization the applications of Cynanchi wilfordii as a food ingredient.


Assuntos
Cynanchum/química , Aromatizantes/química , Compostos Orgânicos Voláteis/química , Cromatografia Gasosa , Culinária , Nariz Eletrônico , Temperatura Alta , Humanos , Paladar
4.
Fitoterapia ; 137: 104285, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31386897

RESUMO

Botanical-based natural products are an important resource for medicinal drug discovery and continue to provide diverse pharmacophores with therapeutic potential against cancer and other human diseases. A prototype Traditional Chinese Medicine (TCM) plant extract library has been established at the US National Cancer Institute, which contains both the organic and aqueous extracts of 132 authenticated medicinal plant species that collectively represent the potential therapeutic contents of most commonly used TCM herbal prescriptions. This library is publicly available in 96- and 384- well plates for high throughput screening across a broad array of biological targets, as well as in larger quantities for isolation of active chemical ingredients. Herein, we present the methodology used to generate the library and the preliminary assessment of the anti-proliferative activity of this crude extract library in NCI-60 human cancer cell lines screen. Particularly, we report the chemical profiling and metabolome comparison analysis of four commonly used TCM plants, namely Brucea javanica, Dioscorea nipponica, Cynanchum atratum, and Salvia miltiorrhiza. Bioassay-guided isolation resulted in the identification of the active compounds, and different extraction methods were compared for their abilities to extract cytotoxic compounds and to concentrate biologically active natural products.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Plantas Medicinais/química , Antineoplásicos Fitogênicos/isolamento & purificação , Brucea/química , Linhagem Celular Tumoral , China , Cynanchum/química , Dioscorea/química , Descoberta de Drogas , Humanos , Medicina Tradicional Chinesa , National Cancer Institute (U.S.) , Compostos Fitoquímicos/isolamento & purificação , Salvia miltiorrhiza/química , Estados Unidos
5.
Fitoterapia ; 136: 104171, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31085309

RESUMO

Seven undescribed C21 steroids, namely cynanchin A-G, together with thirteen known analogues, were isolated from the roots of cynanchum otophyllum. Their structures were elucidated by 1D, 2D NMR and MS spectra, as well as chemical methods. Meanwhile, all of isolates were tested for their anti-hepatic fibrosis activity. Among them, compounds 4-6, 10-12 and 14-17 showed moderate or significant inhibitory effects for the proliferation of hepatic stellate cells (HSCs) induced by transforming growth factor-ß1 (TGF-ß1) in vitro.


Assuntos
Cynanchum/química , Células Estreladas do Fígado/efeitos dos fármacos , Raízes de Plantas/química , Esteroides/farmacologia , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , China , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Esteroides/isolamento & purificação , Fator de Crescimento Transformador beta1
6.
Chem Biodivers ; 16(6): e1900062, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30983116

RESUMO

Seven new polyhydroxypregnane glycosides, named cynotophyllosides P-V, together with three known analogs were isolated from the roots of Cynanchum otophyllum C.K.Schneid. Their structures were elucidated by a variety of spectroscopic techniques, as well as acid-catalyzed hydrolysis. All isolates were tested for their immunological activities in vitro against Con A- and LPS-induced proliferation of mice splenocytes. Immunoenhancing (for 1, 9) and immunosuppressive (for 2) activities were observed. Furthermore, cynotophylloside R (3) showed immunomodulatory as it enhanced the proliferation of splenocytes in low concentration and suppressed immune cells in concentration more than 1.0 µg/ml.


Assuntos
Cynanchum/química , Glicosídeos/química , Pregnanos/química , Animais , Proliferação de Células/efeitos dos fármacos , Cynanchum/metabolismo , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Lipopolissacarídeos/farmacologia , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Conformação Molecular , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Baço/citologia , Baço/efeitos dos fármacos , Baço/metabolismo
7.
Nat Prod Res ; 33(16): 2314-2321, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-29480065

RESUMO

Three new acetophenones, named cynwilforones A-C (1-3), together with cynandione A (4) were isolated from the root bark of Cynanchum wilfordii (Maxim.) Hemsl. Their structures were deduced based on spectroscopic analysis and chemical methods. Compounds 1 and 4 exhibited potential hypoglycemic effects through inhibition of hepatic gluconeogenesis by down-regulating the expression of phosphoenolpyruvate carboxykinase and glucose-6-phosphatase. This is the first report that acetophenones from the root bark of C. wilfordii possesses potential hypoglycemic activity in vitro.


Assuntos
Acetofenonas/isolamento & purificação , Cynanchum/química , Hipoglicemiantes/farmacologia , Acetofenonas/química , Acetofenonas/farmacologia , Animais , Compostos de Bifenilo/isolamento & purificação , Células Cultivadas , Camundongos , Casca de Planta/química , Raízes de Plantas/química
8.
Nat Prod Res ; 33(14): 2032-2037, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29890861

RESUMO

A novel dimeric flavonol glycoside, Cynanflavoside A (1), together with six analogues, kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucopyranoside (2), quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucopyranoside (3), kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-xylopyranoside (4), quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-xylopyranoside (5), kaempferol-3-O-ß-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (6), and quercetin-3-O-galactoside (7) were isolated from the n-butyl alcohol extract of Cynanchum acutum subsp. sibiricum. Their structures were determined spectroscopically and compared with previously reported spectral data. All compounds were evaluated for their anti-complementary activity in vitro, and only compound 5 exhibited anti-complement effects with CH50 value of 0.33 mM.


Assuntos
Cynanchum/química , Flavonóis/química , Glicosídeos/química , Proteínas Inativadoras do Complemento/isolamento & purificação , Proteínas Inativadoras do Complemento/farmacologia , Flavonóis/isolamento & purificação , Glicosídeos/isolamento & purificação , Quempferóis/química , Quempferóis/isolamento & purificação , Quercetina/análogos & derivados , Quercetina/isolamento & purificação
9.
Int J Mol Med ; 42(6): 3157-3170, 2018 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-30272289

RESUMO

Oxidative stress plays an important role in the pathology of liver disorders. Total C­21 steroidal glycosides (TCSGs), isolated from the root tuber of Cynanchum auriculatum Royle ex Wight, have been reported to exert numerous effects, including liver protective and antioxidant effects. In order to investigate the potential mechanisms underlying the protective effects of TCSGs on liver function, the present study used the human normal liver cell line, L02, to evaluate the effects of TCSGs on hydrogen peroxide (H2O2)­induced oxidative injury and inflammatory responses. The L02 cells were pretreated with various concentrations of TCSGs, followed by exposure to 1.5 mM H2O2. Cell viability was determined by a 3­(4,5­dimethylthiazol­2­yl)­2,5­diphenyltetrazolium bromide (MTT) assay. The levels of alanine aminotransferase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase (LDH) and nitric oxide (NO) were measured using colorimetric assays. The activities of superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH­Px) and the production of malondialdehyde (MDA) were also determined. Intracellular reactive oxygen species (ROS) levels were detected using a fluorescent probe. H2O2­induced oxidative toxicity was attenuated following treatment with TCSGs, as indicated by the increase in cell viability, the decreased levels of ALT, AST, LDH, NO, MDA and ROS, and the increased activities of SOD, CAT and GSH­Px. To further explore the possible mechanisms of action of TCSGs, the nuclear factor erythroid 2­related factor 2 (Nrf2) and nuclear factor­κB (NF)­κB pathways were examined. The results revealed that treatment with TCSGs markedly induced Nrf2 nuclear translocation and upregulated the expression of heme oxygenase­1 (HO­1) in the L02 cells damaged by H2O2. In addition, pretreatment with TCSGs inhibited the NF­κB signaling pathway by blocking the degradation of the inhibitor of nuclear factor κBα (IκBα), thereby reducing the expression and nuclear translocation of NF­κB, as well as reducing the expression of tumor necrosis factor­α (TNF­α), interleukin-6 (IL­6), inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX­2). On the whole, the findings of this study demonstrate that TCSGs can protect L02 cells against H2O2­induced oxidative toxicity and inflammatory injury by increasing the expression of Nrf2 and HO­1, mediated by the NF­κB signaling pathway.


Assuntos
Cynanchum/química , Glicosídeos/farmacologia , Peróxido de Hidrogênio/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Apoptose/efeitos dos fármacos , Biomarcadores , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Glicosídeos/química , Humanos , Inflamação/metabolismo , Mediadores da Inflamação/metabolismo , Modelos Biológicos , Estrutura Molecular , Fator 2 Relacionado a NF-E2/metabolismo , NF-kappa B/metabolismo , Oxirredução/efeitos dos fármacos , Extratos Vegetais/química , Espécies Reativas de Oxigênio/metabolismo , Transdução de Sinais/efeitos dos fármacos
10.
Chin J Nat Med ; 16(8): 610-614, 2018 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30197126

RESUMO

The present study was designed to further investigate the C21 steroidal glycosides in Cynanchum plants. Two new steroidal glycosides based on a 13, 14:14, 15-disecopregnane-type aglycone, komaroside P (1) and komaroside Q (2), together with three known compounds (3-5) were isolated from the whole herbs of Cynanchum komarovii. The aglycones of compounds 1 and 2 were two new disecopregnane. Their structures were elucidated on the basis of 1D, 2D NMR spectroscopic data and acid hydrolysis. All the compounds (1-5) showed potent inhibitory activities against human leukemia cell lines (HL-60) with IC50 values ranging from 16.6 to 26.3 µmol·L-1, compared to the positive control 5-fluorouracil (6.4 µmol·L-1).


Assuntos
Cynanchum/química , Glicosídeos/química , Esteroides/química , Sobrevivência Celular/efeitos dos fármacos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células HL-60 , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Esteroides/isolamento & purificação , Esteroides/farmacologia
11.
Int J Biol Macromol ; 119: 1068-1076, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30096394

RESUMO

In the present study, a novel polysaccharide fraction (CAP2-1) from Cynanchum auriculatum Royle ex Wight was obtained by hot water extraction, ethanol precipitation and sequential purification through anion-exchange and size-exclusion chromatography. CAP2-1 was a homogeneous heteropolysaccharide composed of mannose, rhamnose, glucuronic acid, galacturonic acid, galactose and arabinose, with an average molecular weight of 830.93 kDa. FT-IR and NMR spectra of CAP2-1 exhibited typical characteristic signals of polysaccharide. For antioxidant activity evaluation in vitro, CAP2-1 showed effective scavenging capacities against ABTS, DPPH and superoxide anion radical in a dose-dependent manner, with IC50 values at 0.1232, 0.5543 and 0.5881 mg/mL, respectively. At cellular level, CAP2-1 provided a significant protective effect against hydrogen peroxide-induced oxidative stress in HepG2 cells by a compositive oxidation defense mechanism. CAP2-1 could reduce oxidative stress by significantly enhancing the contents of antioxidant enzyme SOD and non-enzymatic antioxidant GSH in oxidative damaged cells, in addition to scavenging ROS directly and improving cell viability and membrane integrity, consequently achieving the intracellular antioxidant activity. The results unveiled that CAP2-1 could be explored as a promising natural antioxidant for application in functional foods.


Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Cynanchum/química , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Polissacarídeos/química , Polissacarídeos/farmacologia , Antioxidantes/isolamento & purificação , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Peso Molecular , Monossacarídeos , Oxirredução/efeitos dos fármacos , Extratos Vegetais/isolamento & purificação , Polissacarídeos/isolamento & purificação , Espécies Reativas de Oxigênio/metabolismo , Espectroscopia de Infravermelho com Transformada de Fourier
12.
Molecules ; 23(5)2018 May 16.
Artigo em Inglês | MEDLINE | ID: mdl-29772722

RESUMO

Genus Cynanchum L. belongs to the family Asclepiadaceae, which comprise more than 200 species distributed worldwide. In Chinese medical practice, numerous drugs (such as tablets and powders) containing different parts of plants of this genus are used to treat snake bites, bruises, osteoblasts, rheumatoid arthritis and tumors. A search for original articles published on the cynanchum genus was performed by using several resources, including Flora of China Official Website and various scientific databases, such as PubMed, SciFinder, the Web of Science, Science Direct, and China Knowledge Resource Integrated (CNKI). Advances in the botanical, ethnomedicinal, phytochemical, and pharmacological studies of this genus are reviewed in this paper. Results showed that more than 440 compounds, including C21 steroids, steroidal saponins, alkaloids, flavonoids and terpene, have been isolated and identified from Cynanchum plants up to now. In vivo and in vitro studies have shown that plants possess an array of biological activities, including anti-tumor, neuroprotective and anti-fungal effects. Popular traditional prescription of Cynanchum sp. was also summed up in this paper. However, many Cynanchum species have received little or no attention. Moreover, few reports on the clinical use and toxic effects of Cynanchum sp. are available. Further attention should be focused on the study of these species to gather information on their respective toxicology data and relevant quality-control measures and clinical value of the crude extracts, active compounds, and bioactive metabolites from this genus. Further research on Cynanchum sp. should be conducted, and bioactivity-guided isolation strategies should be emphasized. In addition, systematic studies of the chemical composition of plants should be enhanced.


Assuntos
Cynanchum/química , Medicamentos de Ervas Chinesas/farmacologia , Compostos Fitoquímicos/farmacologia , Animais , Antifúngicos/química , Antifúngicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Cynanchum/classificação , Medicamentos de Ervas Chinesas/química , Etnobotânica , Etnofarmacologia , Flavonoides/química , Flavonoides/farmacologia , Humanos , Medicina Tradicional , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/farmacologia , Compostos Fitoquímicos/química , Fitosteróis/química , Fitosteróis/farmacologia
13.
Bioorg Med Chem Lett ; 28(9): 1520-1524, 2018 05 15.
Artigo em Inglês | MEDLINE | ID: mdl-29625825

RESUMO

Eight new C21 steroidal glycosides, namely cynanotins A-H (1-8), together with fifteen known analogues, were isolated from the roots of Cynanchum otophyllum. Their structures were elucidated by spectroscopic analysis and chemical methods. In this study, all of isolates were tested for their vitro inhibitory activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480). Compounds 3-15 showed moderate cytotoxic activities against HL-60 cell lines with IC50 values ranging from 11.4 to 37.9 µM. Compounds 5, 9, and 10 showed marked or moderate cytotoxic activities against five human tumor cell lines with IC50 values ranging from 11.4 to 36.7 µM. Compound 11 displayed moderate cytotoxic activities against HL-60, SMMC-7721, MCF-7 and SW480 cell lines with IC50 values of 12.2-30.8 µM. Compared to the positive control (IC50: 35.0 µM), compounds 5, 9-11 exhibited more potential inhibitory activity against MCF-7 cells (IC50: 16.1-25.6 µM).


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Cynanchum/química , Glicosídeos/farmacologia , Esteroides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Estrutura Molecular , Esteroides/química , Esteroides/isolamento & purificação , Relação Estrutura-Atividade
14.
Molecules ; 23(3)2018 Mar 14.
Artigo em Inglês | MEDLINE | ID: mdl-29538318

RESUMO

A new phenolic compound, 2-O-ß-laminaribiosyl-4-hydroxyacetophenone (1), was isolated from Cynanchi Wilfordii Radix (CWR, the root of Cynanchum wilfordii Hemsley), along with 10 known aromatic compounds, including cynandione A (2), bungeisides-C (7) and -D (8), p-hydroxyacetophenone (9), 2',5'-dihydroxyacetophenone (10), and 2',4'-dihydroxyacetophenone (11). The structure of the new compound (1) was elucidated using spectroscopic methods and chemical methods. The structure of cynandione A (2), including a linkage mode of the biphenyl parts that remained uncertain, was unambiguously confirmed using the 2D 13C-13C incredible natural abundance double quantum transfer experiment (INADEQUATE) spectrum. Additionally, health issues related to the use of Cynanchi Auriculati Radix (CAR, the root of Cynanchum auriculatum Royle ex Wight) instead of CWR have emerged. Therefore, constituents present in methanolic extracts of commercially available CWRs and CARs were examined using UV-sensitive high-performance liquid chromatography (HPLC), resulting in common detection of three major peaks ascribed to cynandione A (2), p-hydroxyacetophenone (9), and 2',4'-dihydroxyacetophenone (11). Thus, to distinguish between these ingredients, a thin-layer chromatography (TLC) method, combined with only UV irradiation detection, focusing on wilfosides C1N (12) and K1N (13) as marker compounds characteristic of CAR, was performed. Furthermore, we propose this method as a simple and convenient strategy for the preliminary distinction of CWR and CAR to ensure the quality and safety of their crude drugs.


Assuntos
Cynanchum/química , Fenóis/análise , Fenóis/química , Acetofenonas/química , Acetofenonas/isolamento & purificação , Compostos de Bifenilo/química , Compostos de Bifenilo/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Raízes de Plantas/química
15.
Bioorg Med Chem Lett ; 28(7): 1252-1256, 2018 04 15.
Artigo em Inglês | MEDLINE | ID: mdl-29526485

RESUMO

Bioassay-guided fractionation of the methanolic extract from the roots of Cynanchum atratum has resulted in the isolation of three new pregnane glycosides (1-3) along with four known compounds (4-7). Their structures were identified by analysis of the spectroscopic data including extensive 2D NMR. All of the isolates were evaluated for their potential to inhibit the melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Of these, compounds 4-7 dose-dependently inhibited the melanin production with the IC50 values ranging from 4 µM to 33 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Cynanchum/química , Glicosídeos/farmacologia , Melaninas/antagonistas & inibidores , Melanoma Experimental/tratamento farmacológico , Extratos Vegetais/farmacologia , Pregnanos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Melaninas/biossíntese , Melanoma Experimental/metabolismo , Melanoma Experimental/patologia , Conformação Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química , Pregnanos/química , Pregnanos/isolamento & purificação , Relação Estrutura-Atividade
16.
Int J Biol Macromol ; 114: 130-136, 2018 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-29572138

RESUMO

In this study, a novel method was developed to conjugate quercetin with Cynanchum auriculatum starch. Quercetin was first succinylized and then grafted onto C. auriculatum starch through a N,N'­carbonyldiimidazole mediated reaction. The obtained water soluble quercetin grafted starch (quercetin-g-starch) was characterized by several instrumental methods. UV-vis spectrum of quercetin-g-starch aqueous solution exhibited two absorption bands at around 300 and 430nm. Fourier-transform infrared spectrum of quercetin-g-starch showed characteristic bands at 1731 and 1568cm-1, assigning to CO stretching of esterified carboxyl group and CC stretching of aromatic ring, respectively. Proton nuclear magnetic resonance spectrum of quercetin-g-starch showed partial proton signals of starch (3.30-5.47ppm) and quercetin (6.19-7.68ppm). All above results suggested quercetin was successfully grafted onto C. auriculatum starch. Besides, quercetin-g-starch particles were irregular in shape and were in an amorphous state. Notably, the thermal stability, resistant starch content as well as antioxidant activity of C. auriculatum starch was greatly enhanced by grafting with quercetin. This indicated the potential of quercetin-g-starch in the development of a novel resistant starch with antioxidant activity.


Assuntos
Antioxidantes/química , Cynanchum/química , Quercetina/química , Amido/química
17.
J Dairy Sci ; 101(4): 2842-2850, 2018 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-29428763

RESUMO

The herbaceous plant Cynanchum otophyllum Schneid. is widely used as a milk coagulant to make a Chinese traditional milk product, milk cake. However, the milk-clotting compounds and their mechanism remain unclear. In this study, crude proteases were extracted from the dried leaves of Cynanchum otophyllum Schneid. using citric acid-phosphate buffer and then partially purified by weak anion exchange chromatography. Two proteases, QA and QC, with molecular weights of 14 and 27 kDa, respectively, were shown to exhibit milk-clotting activity. A study of the effects of pH and temperature on the milk-clotting activity and proteolytic activity of the proteases showed that they exhibited good pH stability from pH 5.5 to 7.5 and good thermal stability at temperatures from 50 to 70°C. The QA and QC were the cysteine proteases, able to hydrolyze ß-casein and κ-casein completely, and α-casein partially. The cleavage site on κ-casein determined by Orbitrap (Thermo Fisher Scientific, San Jose, CA) analysis showed that QA and QC could cleave κ-casein at Ser132-Thr133. Overall, the results suggest that the Cynanchum otophyllum Schneid. proteases are a promising milk-clotting enzyme that could be used for manufacturing milk cake and cheese.


Assuntos
Cynanchum/química , Leite/química , Peptídeo Hidrolases/metabolismo , Animais , Caseínas/química , Cisteína Proteases/isolamento & purificação , Cisteína Proteases/metabolismo , Hidrólise , Peso Molecular , Proteólise , Temperatura
18.
Phytochem Anal ; 29(5): 472-475, 2018 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-29430752

RESUMO

INTRODUCTION: Precise identification of botanical origin of plant species is crucial for the quality control of herbal medicine. In Korea, the root part of Cynanchum auriculatum has been misused for C. wilfordii in the herbal drug market due to their morphological similarities. Currently, DNA analysis using the polymerase chain reaction (PCR) method is employed to discriminate between these species. OBJECTIVE: In order to develop a new analytical tool for the rapid discrimination of C. wilfordii and C. auriculatum, terahertz (THz) spectroscopy was employed. METHODOLOGY: Authentic samples of C. wilfordii and C. auriculatum were provided from the National Institute and standardized pellets for each species were prepared to get optimum results with terahertz time-domain spectroscopy (THz-TDS) in frequency range 0.2-1.20 THz. RESULTS: The C. wilfordii pellet showed longer time delay compare to the sample of C. auriculatum and this was due to the difference in permittivity. The pellet samples of C. wilfordii and C. auriculatum showed a permittivity difference of about 0.08 at 0.2-1.20 THz. CONCLUSION: The experimental results indicated that THz-TDS analysis can be an effective and rapid method for the discrimination of C. wilfordii and C. auriculatum, and this application can be expanded for the discrimination of other similar herbal medicines.


Assuntos
Cynanchum/química , Espectroscopia Terahertz/métodos , Cynanchum/classificação , Padrões de Referência , Especificidade da Espécie
19.
Cancer Lett ; 420: 195-207, 2018 04 28.
Artigo em Inglês | MEDLINE | ID: mdl-29425683

RESUMO

Uncontrolled excessive activation of Hedgehog (Hh) signaling pathway is linked to a number of human malignant tumorigenesis. To obtain valuable Hh pathway inhibitors from natural product, in present study, a pair of novel epimers, Cynanbungeigenin C (CBC) and D (CBD) from the plant Cynanchum bungei Decne were chemically characterized by multiple spectroscopic data and chemical derivatization, and evaluated for their inhibition on Hh pathway. Mechanistically, CBC and CBD block Hh pathway signaling not through targeting Smo and Sufu, but at the level of Gli. In addition, both eipmers significantly suppress Hh pathway-dependent Ptch+/-; p53-/- medulloblastoma in vitro and in vivo. Furthermore, both CBC and CBD inhibited two Smo mutants induced Hh pathway activation, which suggested that they are potential compounds for the treatment of medulloblastoma with primary or acquired resistance to current Smo inhibitors. These results highlight the potential of CBC and CBD as effective lead compounds in the treatment of medulloblastoma and other Hh-dependent malignancy.


Assuntos
Neoplasias Cerebelares/tratamento farmacológico , Cynanchum/química , Meduloblastoma/tratamento farmacológico , Fitosteróis/administração & dosagem , Fitosteróis/isolamento & purificação , Transdução de Sinais/efeitos dos fármacos , Animais , Neoplasias Cerebelares/metabolismo , Células HEK293 , Proteínas Hedgehog/metabolismo , Humanos , Meduloblastoma/metabolismo , Camundongos , Células NIH 3T3 , Fitosteróis/química , Fitosteróis/farmacologia , Extratos Vegetais/análise , Ensaios Antitumorais Modelo de Xenoenxerto , Proteína GLI1 em Dedos de Zinco/metabolismo
20.
J Asian Nat Prod Res ; 20(3): 263-269, 2018 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-28537086

RESUMO

Two new C21 steroidal glycosides, cynataihosides E (1) and F (2), together with a known one, sublanceoside H2 (3), were isolated from Cynanchum taihangense. The aglycone of cynataihoside F (2) was also a new compound. Their structures were elucidated on the basis of NMR spectroscopic data, HR-ESI-MS analysis, and chemical evidence. Their cytotoxic activities against three human tumor cell lines (HL-60, THP1, and Caco2) were reported.


Assuntos
Cynanchum/química , Glicosídeos/isolamento & purificação , Esteroides/isolamento & purificação , Células CACO-2 , Glicosídeos/química , Glicosídeos/farmacologia , Células HL-60 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química , Esteroides/química , Esteroides/farmacologia
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