RESUMO
Bixasteroid (1), one new steroid together with five known compounds (2-6), were isolated from the ethyl acetate fraction of ethanol extract of Bixa orellana fruits. All of these known compounds were isolated from the plant for the first time. Their structures were elucidated on the basis of spectroscopic analysis, and the absolute configuration of compound 1 was determined by X-ray crystallographic data analysis as well as by the quantum chemical ECD calculations. All the isolated compounds were tested for their anti-inflammatory activities. Compounds 1 and 2 showed inhibiting NO release activities in LPS-induced RAW 264.7 macrophages with the IC50 values of 4.72 ± 0.28 and 5.48 ± 1.48 µM, respectively.
Assuntos
Bixaceae , Frutas , Bixaceae/química , Extratos Vegetais/química , Anti-Inflamatórios/farmacologia , MacrófagosRESUMO
Ten new dihydroagarofuran sesquiterpene polyol esters, tripterdines A-J (1-10) were isolated from the stem and branch of Tripterygium wilfordii. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses, including UV, IR, HRESIMS, NMR, and CD exciton chirality method. The structures of compounds 1, 3, and 6 were confirmed by X-ray crystallographic analyses. The anti-inflammatory and cytotoxic activities were assessed for all the compounds (1-10). Compounds 3, 5 and 10 exhibited potent anti-inflammatory activities with the secretion level of TNF-α ranging from 43.86% to 51.27%, and the IL-6 ranging from 32.44% to 50.64%. In addition, compounds 1, 3, 7 and 9 showed weak cytotoxicities against three human tumor cell lines (Huh7, MCF-7 and HCT-116).
Assuntos
Sesquiterpenos , Tripterygium , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Humanos , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Tripterygium/químicaRESUMO
Seven new phenylpropanoids, including two pairs of enantiomers of 8-O-4'-type neolignans, named (±)-xanthiifructins A-B (1a/1b-2a/2b), a pair of simple phenylpropanoid derivatives (±)-xanthiifructins C (3a/3b), and a racemic phenylpropanoid derivative xanthiifructin D (4), together with four known analogues (5-8) were isolated from the fruits of Xanthium sibiricum. Racemic xanthiifructins A-C were separated on chiral HPLC columns. Their structures were elucidated by comprehensive spectroscopic data analysis and comparison with the literatures. The anti-inflammatory and cytotoxic activities were evaluated for all isolates. Among them, (-)-xanthiifructin C (3b) exhibited potent inhibitory effect against nitric oxide production in lipopolysaccharide-activated RAW 264.7 mouse macrophage cells with an IC50 value of 9.94 ± 0.57 µM. All compounds obviously were inactive for three human tumor cell lines (MCF-7, HepG2, and A549) with IC50 values much more than 10 µM.
Assuntos
Xanthium , Animais , Anti-Inflamatórios/farmacologia , Frutas , Camundongos , Estrutura Molecular , Células RAW 264.7RESUMO
A pair of new enantiomeric trinorsesquiterpenes, (+)-genpenterpene A (1a) and (-)-genpenterpene A (1b), together with seven known compounds (2-8), were isolated from the aerial parts of Justicia gendarussa Burm.f.. All of these known compounds were isolated from this plant for the first time. Racemic genpenterpene A was separated by chiral HPLC column. Their chemical structures were elucidated based on extensive spectroscopic analysis, single crystal X-ray diffraction, and ECD calculations. (+)-genpenterpene A (1a) exhibited potent inhibitory effect against nitric oxide production in lipopolysaccharide-activated RAW 264.7 mouse macrophage cells with an IC50 value of 9.54 ± 1.02 µM.
Assuntos
Justicia , Animais , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Componentes Aéreos da Planta , Células RAW 264.7RESUMO
Lyciyunin, a new dimer of feruloyltyramine (1), together with five known tyramines (2-6), was isolated from the water-soluble fraction of an EtOH extract of the root of L. yunnanense. Based on HR-TOF-MS, NMR spectral data and quantum chemistry ECD calculations, the structure of this new compound was determined, including its absolute configuration. Compounds (1-6) were tested for their antioxidant activity using in vitro DPPH radical scavenging assay, and 1-6 showed the moderate antioxidant activities with IC50 values of 12.44 ± 0.39, 21.29 ± 0.75, 24.44 ± 1.63, 21.15 ± 0.66, 21.15 ± 0.66 and 45.15 ± 0.56 µM, respectively. Compounds (5-6) showed anti-inflammatory activity in LPS-induced RAW 264.7 macrophages with the IC50 values of 43.95 ± 6.11 and 33.50 ± 2.04 µM, respectively.
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Antioxidantes/farmacologia , Ácidos Cumáricos/química , Lycium/química , Tiramina/análogos & derivados , Tiramina/química , Animais , Anti-Inflamatórios não Esteroides/química , Antioxidantes/química , Dimerização , Avaliação Pré-Clínica de Medicamentos , Etanol/química , Lipopolissacarídeos/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Estrutura Molecular , Extratos Vegetais/química , Células RAW 264.7 , Tiramina/farmacologiaRESUMO
Three new compounds (1-3), together with six known compounds (4-9), were isolated from the ethyl acetate fraction of ethanol extract of the aerial parts of Justicia gendarussa Burm.f. All of these known compounds were isolated from the plant for the first time. Their structures including absolute configurations were elucidated on the basis of HR-ESI-MS, NMR spectroscopic analyses, single crystal X-ray diffraction and comparison with the literatures. Compounds 1-9 were tested for their antioxidant and anti-inflammatory activities. Compounds 5 and 8 showed the antioxidant activities with IC50 values of 28.61 ± 1.56 and 22.55 ± 1.38 µM, respectively. Compounds 2 and 3 showed anti-inflammatory activity in LPS-induced RAW 264.7 macrophages with the IC50 values of 20.95 ± 1.11 and 16.50 ± 1.04 µM, respectively.
Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Justicia , Componentes Aéreos da Planta/química , Anti-Inflamatórios/química , Antioxidantes/químicaRESUMO
This study was carried out to investigate the chemical constituents from Xanthii Fructus(the fruits of Xanthium sibiricum). The compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 and ODS chromatography and semi-preparative HPLC. Base on HR-ESI-MS, NMR and other spectral data, their structures were identified. The anti-inflammatory activity of the isolated compounds was evaluated by lipopolysaccharide(LPS)-induced macrophage RAW264.7 as a screening model. A total of twenty-one compounds were isolated from the EtOAc fraction of 95% ethanol extract and identified as uracil(1), thymine(2), uridine(3), indole-3-carbaldehyde(4), indole-3-carboxylic acid(5), 2'-O-methyluridine(6), guanosine(7), 2,4(1H,3H)-quinazolinedione(8), 3-hydroxy-3-(2-hydroxyethyl)indolin-2-one(9), nicotinamide(10), N-acetyl-L-phenylalaninol(11), heliolactam(12), terresoxazine(13), caudatin(14), qingyangshengenin(15), caudatin-3-O-ß-D-oleandropyranosyl-(1â4)-ß-D-cymaropyranosyl-(1â4)-ß-D-cymaropyranoside(16), caudatin-3-O-ß-D-cymaropyranosyl-(1â4)-ß-D-oleandropyranosyl-(1â4)-ß-D-cymaropyranosyl-(1â4)-ß-D-cymaropyranoside(17), caudatin-3-O-α-L-cymaropyranosyl-(1â4)-ß-D-cymaropyranosyl-(1â4)-ß-D-cymaropyranosyl-(1â4)-α-L-cymaropyranosyl-(1â4)-ß-D-oleandropyranosyl-(1â4)-ß-D-cymaropyranoside(18), qinyangshengenin-3-O-ß-D-oleandropyranosyl-(1â4)-ß-D-oleandropyranosyl-(1â4)-ß-D-cymaropyranoside(19), qinyangshengenin-3-O-ß-D-oleandropyranosyl-(1â4)-ß-D-cymaropyranosyl-(1â4)-ß-D-digitoxopyranoside(20), rostratamine-3-O-ß-D-oleandropyranosyl-(1â4)-ß-D-cymaropyranosyl-(1â4)-ß-D-cymaropyranoside(21). Compounds 5-21 are obtained from genus Xanthium for the first time. Compounds 12 and 13 indirectly exhibited anti-inflammatory activity by suppressing LPS-induced NO production in RAW264.7 cells with IC_(50) values of(15.45±0.56) and(20.14±0.78) µmol·L~(-1), respectively.
Assuntos
Frutas , Xanthium , Cromatografia Líquida de Alta Pressão , Glicosídeos , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Seven previously undescribed sulfur-containing compounds, (+)- and (-)-xanthiazinone A, (+)- and (-)-xanthiazinone B, (+)- and (-)-xanthiazinone C and xanthiazinone D, and four known thiazinedione derivatives, together with three thiophene derivatives were isolated from the fruits of Xanthium sibiricum. Racemic xanthiazinones A-C were separated by chiral HPLC columns. Their chemical structures were elucidated based on extensive spectroscopic analyses, ECD calculations, and single crystal X-ray diffractions. The X-ray crystallographic analyses for xanthiazinones A-C represent the first example described for the structure elucidation of the thiazinedione with the five-membered lactone ring attached via an oxygen atom. Accordingly, the previously proposed structure for xanthiazinone was revised. The anti-inflammatory and cytotoxic activities were evaluated for all the isolated compounds. (+)-xanthiazinone B and 2-hydroxy-xanthiazone exhibited potent inhibitory effects against nitric oxide production in lipopolysaccharide-activated RAW 264.7 mouse macrophage cells with IC50 values of 8.75 and 10.90 µM, respectively. All compounds obviously were inactive for three human tumor cell lines (HepG2, MCF-7, and A549) with IC50 values more than 10 µM.
Assuntos
Xanthium , Animais , Anti-Inflamatórios , Frutas , Humanos , Camundongos , Enxofre , Compostos de EnxofreRESUMO
BACKGROUND: Melanoma is a high fatality skin cancer which lacks effective drugs. Sasanquasaponin, an important sort of constituents in theaceae, has been demonstrated to have potent anti-tumor effect in breast cancer and hepatocellular carcinoma. As a sasanquasaponin, we speculate that Sasanquasaponin III (SQS III) isolated from Schima crenata Korth may also have anti-tumor activity. PURPOSE: This study aims to investigate whether SQS III has anti-melanoma activity and examine the underlying mechanisms of SQS III against melanoma. METHODS/STUDY DESIGNS: The anti-proliferative effect of SQS III was assessed by cells viability assay. Annexin V-FITC/PI double staining assay was utilized for detection of apoptosis. Mitochondrial membrane potential and reactive oxygen species (ROS) production were detected using JC-1 and DCFH-DA assay, respectively. Autophagy was monitored using transmission electron microscopy (TEM) and GFP-LC3 transfection fluorescence analysis. Autophagosome-lysosome fusion and lysosomal degradation were determined using a GFP-LC3 & LAMP1 co-localization assay and DQ-BSA staining. Proteins related to apoptosis and autophagy were analyzed by Western blotting. RESULTS: Our results demonstrated that the SQS III exhibited potent anti-cancer activity in A375 cells by inducing both apoptosis and autophagy. In melanoma cells treated with SQS III, caspases were activated and PARP was cleaved, proving the occurrence of apoptosis. Mechanistic studies indicated that the pro-apoptosis activity of SQS III was mediated by death receptor pathway and mitochondrial dysfunction which was induced by ROS accumulation and reversed by the ROS inhibitor N-acetyl-cysteine (NAC). In addition to triggering apoptosis, SQS III may also cause autophagy in melanoma cells. Our results demonstrated that SQS III induced up-regulated expression of GFP-LC3, autophagosome-lysosomal fusion and lysosomal degradation. Additionally, the ROS accumulation was also involved in the activation of autophagy. Meanwhile, it was also found that after SQS III treatment, the expression of LC3-II was up-regulated and the AKT/mTOR signaling pathway was inhibited. The autophagy inhibitor 3-MA converted cytotoxicity and apoptosis of SQS III in A375 cells, which indicated that autophagy promoted the SQS III-induced apoptosis. CONCLUSION: SQS III showed potent anti-cancer activity by inducing apoptosis and autophagy, which provides insights into its possible use as a therapy for melanoma.
Assuntos
Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Autofagia/efeitos dos fármacos , Melanoma/tratamento farmacológico , Saponinas/farmacologia , Theaceae/química , Antineoplásicos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Proteínas Proto-Oncogênicas c-akt/genética , Proteínas Proto-Oncogênicas c-akt/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Proteínas Quinases S6 Ribossômicas 70-kDa/genética , Proteínas Quinases S6 Ribossômicas 70-kDa/metabolismo , Saponinas/química , Transdução de Sinais/efeitos dos fármacos , Serina-Treonina Quinases TOR/genética , Serina-Treonina Quinases TOR/metabolismoRESUMO
Plant-derived extracts are a promising source of new drugs. Schima superba is traditionally used in China for heat clearing, detoxification, and treatment of furuncles. In this study, the anticandidal properties and mechanism of action of S. superba (SSE) were explored using a stem bark extract. SSE possessed high polyphenol and saponin contents of 256.6 ± 5.1 and 357.8 ± 31.5 µg/mg, respectively. A clear inhibition zone was observed for C. albicans growth through the disc diffusion method and the 50% inhibition of C. albicans by SSE was 415.2 µg/mL. Transcriptomic analysis in C. albicans treated with different doses of SSE was conducted through RNA-seq. Average values of 6068 genes and 20,842,500 clean reads were identified from each sample. Among these samples, 1680 and 1956 genes were differentially expressed genes (DEGs) from the SSE treatments of 0.2 and 0.4 mg/mL, respectively. C. albicans growth was inhibited by the changes in gene expression associated with the cell wall and membrane composition including the regulation of chitin degradation and ergosterol biosynthesis. This result could be reflected in the irregularly wrinkled morphology of the ruptured cell as revealed through SEM analysis. ESI-MS and NMR analyses revealed that the major compound purified from SSE was sasanquasaponin III and the 50% inhibition of C. albicans was 93.1 µg/mL. In summary, the traditional Chinese medicine S. superba can be applied as an anticandidal agent in complementary and alternative medicine.
Assuntos
Antifúngicos , Candida albicans/crescimento & desenvolvimento , Casca de Planta/química , Extratos Vegetais , Theaceae/química , Antifúngicos/química , Antifúngicos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologiaRESUMO
BACKGROUND: There have been some reports implicating the pharmacologic action of Dihydrosanguinarine (DHSA), but little research including the effects of it on cancer cells. PANC-1 cells have mutations in K-Ras and TP53, which respectively express mutant K-Ras and p53 protein, and the mutations in Ras/p53 have been believed with closely relationship to the occurrence of various tumors. PURPOSE: To reveal the inhibition of Dihydrosanguinarine on pancreatic cancer cells (PANC-1 and SW1990) proliferation by inducing G0/G1 and G2/M phase arrest via the downregulation of mut-p53 protein, inducing apoptosis and inhibiting invasiveness through the Ras/Mek/Erk signaling pathway. METHODS: Human pancreatic cancer cell lines were cultured with cisplatin and DHSA. Then, cell proliferation, the cell cycle and apoptosis were measured by CCK-8 and flow cytometry. The migratory and invasive abilities of pancreatic cancer cells were evaluated by transwell assay. The expression levels of mRNA and protein were measured by RT-PCR and western blotting. RESULTS: The results showed that DHSA treatment inhibited cell proliferation, migration and invasion in a time- and dose-dependent manner and led to induction of cell cycle arrest and apoptosis. G0/G1 and G2/M phase arrest inhibited the viability of PANC-1 cells by downregulating the expression of mut-p53 protein. Decreased levels of C-Raf and Erk phosphorylation in DHSA-treated PANC-1 and SW1990 cells were observed in a time- and dose-dependent manner. However, the total expression of p53 and Ras proteins had a different change in PANC-1 and SW1990 cells. CONCLUSIONS: Our findings offer the novel perspective that DHSA inhibits pancreatic cancer cells through a bidirectional regulation between mut-p53/-Ras and WT-p53/-Ras to restore the dynamic balance by Ras and p53 proteins.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Benzofenantridinas/farmacologia , Isoquinolinas/farmacologia , Neoplasias Pancreáticas/tratamento farmacológico , Proteína Supressora de Tumor p53/genética , Apoptose/efeitos dos fármacos , Apoptose/genética , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Pontos de Checagem do Ciclo Celular/genética , Linhagem Celular Tumoral , Movimento Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Humanos , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Neoplasias Pancreáticas/metabolismo , Neoplasias Pancreáticas/patologia , Fosforilação/efeitos dos fármacos , Proteínas Proto-Oncogênicas p21(ras)/genética , Quinases raf/genética , Quinases raf/metabolismo , Proteínas ras/genética , Proteínas ras/metabolismoRESUMO
Three new lignanamides, that is, a new lignanamide (1), and a pair of enantiomers (2a and 2b) were isolated from the EtOAc-soluble fraction of an EtOH extract of the root of Lycium chinense. The structures of these new compounds, including their absolute configuration, were established on the basis of HR-ESI-MS, NMR spectroscopic data and quantum chemical ECD calculations. Compound 2a showed significant anti-inflammatory activity in LPS-induced RAW 264.7 macrophages with the IC50 value of 10.77 ± 2.14 µM, comparing to that of positive control quercetin (17.21 ± 0.50 µM).
Assuntos
Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Lycium/química , Animais , Avaliação Pré-Clínica de Medicamentos , Lipopolissacarídeos/toxicidade , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Extratos Vegetais/química , Raízes de Plantas/química , Células RAW 264.7 , Espectrometria de Massas por Ionização por Electrospray , EstereoisomerismoRESUMO
A new lignanamide (1), lyciumamide K, together with four known analogues (2-5), was isolated from the root of Lycium yunnanense Kuang. Based on HR-ESI-MS, NMR spectral data and quantum chemistry ECD calculations, the structure of this new compound was confirmed, including its absolute configuration. Evaluation of the antioxidant activity of compounds 1-5 in the oxygen radical absorption capacity (ORAC) assay showed that they all exhibited significant antioxidant activities. Particularly, compound 1 showed the best activity with ORAC values (U/mol) of 7.90 ± 0.52. Thus, the new lignanamide may be a good source of bioavtive and protective compounds.
Assuntos
Sequestradores de Radicais Livres/isolamento & purificação , Lignanas/isolamento & purificação , Lycium/química , Dipeptídeos/química , Dipeptídeos/isolamento & purificação , Dipeptídeos/farmacologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/químicaRESUMO
An actinomycete strain 200-09, isolated from a soil sample collected from the coast of Hawaii, USA, was identified as Streptomyces antibioticus on the basis of its morphological, physiological and biochemical characteristics as well as 16S rDNA analysis. A new antimycin-type antibiotic, kitamycin C (1), together with kitamycin A (2), kitamycin B (3), urauchmycin B (4), deisovaleryblastomycin (5) was isolated from a cultured broth of strain 200-09. The structure of the new compound was determined by spectroscopic data, including HR-ESI-MS and NMR. All the compounds exhibited antifungal activities against Candida albicans with MIC of about 25.0 µg mL-1.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Macrolídeos/química , Macrolídeos/farmacologia , Streptomyces antibioticus/química , Antibacterianos/química , Antifúngicos/química , Antimicina A/análogos & derivados , Antimicina A/farmacologia , Candida albicans/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Sesquiterpene lactones (SLs) are the active constituents of a variety of medicinal plants and found to have potential anticancer activities. However, the intracellular molecular targets of SLs and the underlying molecular mechanisms have not been well elucidated. In this study, we observed that EM23, a natural SL, exhibited anti-cancer activity in human cervical cancer cell lines by inducing apoptosis as indicated by caspase 3 activation, XIAP downregulation and mitochondrial dysfunction. Mechanistic studies indicated that EM23-induced apoptosis was mediated by reactive oxygen species (ROS) and the knockdown of thioredoxin (Trx) or thioredoxin reductase (TrxR) resulted in a reduction in apoptosis. EM23 attenuated TrxR activity by alkylation of C-terminal redox-active site Sec498 of TrxR and inhibited the expression levels of Trx/TrxR to facilitate ROS accumulation. Furthermore, inhibition of Trx/TrxR system resulted in the dissociation of ASK1 from Trx and the downstream activation of JNK. Pretreatment with ASK1/JNK inhibitors partially rescued cells from EM23-induced apoptosis. Additionally, EM23 inhibited Akt/mTOR pathway and induced autophagy, which was observed to be proapoptotic and mediated by ROS. Together, these results reveal a potential molecular mechanism for the apoptotic induction observed with SL compound EM23, and emphasize its putative role as a therapeutic agent for human cervical cancer.
Assuntos
Lactonas/farmacologia , MAP Quinase Quinase 4/metabolismo , Sesquiterpenos/farmacologia , Tiorredoxina Dissulfeto Redutase/antagonistas & inibidores , Tiorredoxina Dissulfeto Redutase/metabolismo , Neoplasias do Colo do Útero/tratamento farmacológico , Apoptose/efeitos dos fármacos , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Ativação Enzimática , Feminino , Células HL-60 , Humanos , Células K562 , Células MCF-7 , Espécies Reativas de Oxigênio/metabolismo , Transfecção , Neoplasias do Colo do Útero/enzimologia , Neoplasias do Colo do Útero/patologiaRESUMO
Two new ent-kaurane diterpene glycosides, ranunculosides A (1) and B (2), and a new benzophenone, ranunculone C (3), were isolated from the aerial part of Ranunculus muricatus Linn. The chemical structures of compounds 1-3 were established to be (2S)-ent-kauran-2ß-ol-15-en-14-O-ß-d-glucopyranoside, (2S,4S)-ent-kauran-2ß,18-diol-15-en-14-O-ß-d-glucopyranoside, and (R)-3-[2-(3,4-dihydroxybenzoyl)-4,5-dihydroxy-phenyl]-2-hydroxylpropanoic acid, respectively, by spectroscopic data and chemical methods. The absolute configuration of 1 was determined by the combinational application of RP-HPLC analysis and Mosher's method.
Assuntos
Benzofenonas/isolamento & purificação , Diterpenos/isolamento & purificação , Glicosídeos/isolamento & purificação , Ranunculus/química , Benzofenonas/química , Cromatografia Líquida de Alta Pressão , Diterpenos/química , Glicosídeos/química , Conformação Molecular , Extratos VegetaisRESUMO
OBJECTIVE: To study the alkaloids of Macleaya cordata and their anti-tumor activities. METHOD: Alcohol and liquid-liquid extraction were used methods were used to extract the alkaloids constituents, and silica gel, reverse-phase octadecylsilyl (ODS), sephadex LH-20 chromatographic methods and HPLC were applied to isolate and purify compounds. MS, NMR spectroscopic methods were used to determine their structures. Furthermore, the cytotoxicity of these chemical components for MCF-7 and SF-268 cell lines was measured by MTT method. RESULT: Twelve alkaloids were isolated from the fruits of M. cordata, and their structures were identified as: maclekarpine E (1), 6-acetonyldihyrochelerythrine (2), cavidilinine (3), 6-acetonyldihyrosanguinnarine (4), O-methylzanthoxyline (5), 6-methoxy-dihydrosanguinarine (6), spallidamine (7), 6-hydroxyldihydrochelerythrine (8), arnotianamida (9), dihydrosanguinarine (10), protopine (11), and cryptopine (12). CONCLUSION: Compounds 1, 3, 7-9 were isolated from M. cordata for the first time, and compound 5 is a new natural product. The results of cytotoxic assay indicated that compound 6 showed strong cytotoxicity against MCF-7 and SF-268 cell lines with IC50 values of 0.61 µmol · L(-1) and 0.54 µmol · L(-1), respectively.
Assuntos
Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Papaveraceae/química , Alcaloides/farmacologia , Linhagem Celular Tumoral , HumanosRESUMO
A new cytotoxic benzophenanthridine isoquinoline alkaloid, named cordatine (1), together with one known alkaloid 8-methoxydihydrochelerythrine (2), was isolated from the fruits of Macleaya cordata. The structure of the new compound was elucidated by spectroscopic methods including 1D and 2D NMR, HR-ESI-MS. Both compounds indicated significant cytotoxicity against MCF-7 and SF-268 cell lines.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Benzofenantridinas/isolamento & purificação , Benzofenantridinas/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Frutas/química , Papaveraceae/química , Alcaloides/química , Antineoplásicos Fitogênicos/química , Benzofenantridinas/química , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Humanos , Isoquinolinas , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
A novel triterpenoid 3α,16ß,23,24-tetrahydroxy-28-nor-ursane-12,17,19,21-tetraen (1) was isolated from the fruits of Gardenia jasminoides var. radicans Makino. The structure of the new compounds was elucidated on the basis of spectroscopic analysis including MS and NMR data. Compound 1 was in vitro tested for cytostatic activity on human throat cancer (Hep-2) cell line by 3-(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyltetrazolium bromide method and showed mild anticancer activity with the IC50 of 31.2 µM.
Assuntos
Frutas/química , Gardenia/química , Triterpenos/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Células Hep G2 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Extratos Vegetais/química , Triterpenos/isolamento & purificaçãoRESUMO
The leaves of Rhododendron seniavinii Maxim with little phytochemical information are used as folk remedies for the treatment of acute and chronic bronchitis in China. In our pursuing for the biologically active chemical constituents in the leaves, a new flavonoid glycoside 5,7,3'-trimethoxy-quercetin-3-O-ß-D-glucopyranoside (1) was isolated from the water extract of its leaves, together with two known compounds 5,7,3'-trimethoxy-quercetin (2) and ovafolinin B-9'-O-ß-D-glucopyranoside (3). The structures of the new flavonoid glucoside as well as two known compounds were elucidated by spectroscopic and chemical methods.