RESUMEN
Bletilla striata is the dried tuber of B. striata (Thund.) Reichb.f., which has antibacterial, anti-inflammatory, anti-tumor, antioxidant and wound healing effects. Traditionally, it has been used for hemostasis therapy, as well as to treat sores, swelling and chapped skin. In this study, we used the ultraviolet (UV) absorbance rate of B. striata extracts as the index, and the extraction was varied with respect to the solid-liquid ratio, ethanol concentration, ultrasonic time and temperature in order to optimize the extraction process for its sunscreen components. The main compounds in the sunscreen ingredients of Baiji (B. striata) were analyzed using ultra-high-performance liquid chromatography combined with quadrupole time-of-flight tandem mass spectrometry. The sunscreen properties were subsequently evaluated in vitro using the 3M tape method. The results show that the optimal extraction conditions for the sunscreen components of B. striata were a solid-liquid ratio of 1:40 (g/mL), an ethanol concentration of 50%, an ultrasonic time of 50 min and a temperature of 60 °C. A power of 100 W and an ultrasonic frequency of 40 Hz were used throughout the experiments. Under these optimized conditions, the UV absorption rate of the isolated sunscreen components in the UVB region reached 84.38%, and the RSD was 0.11%. Eighteen compounds were identified, including eleven 2-isobutyl malic acid glucose oxybenzyl esters, four phenanthrenes, two bibenzyl and one α-isobutylmalic acid. An evaluation of the sunscreen properties showed that the average UVB absorption values for the sunscreen samples from different batches of B. striata ranged from 0.727 to 1.201. The sunscreen ingredients of the extracts from B. striata had a good UV absorption capacity in the UVB area, and they were effective in their sunscreen effects under medium-intensity sunlight. Therefore, this study will be an experimental reference for the extraction of sunscreen ingredients from the B. striata plant, and it provides evidence for the future development of B. striata as a candidate cosmetic raw material with UVB protection properties.
Asunto(s)
Orchidaceae , Extractos Vegetales , Protectores Solares , Protectores Solares/química , Protectores Solares/farmacología , Protectores Solares/aislamiento & purificación , Orchidaceae/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Ondas Ultrasónicas , Espectrometría de Masas en Tándem , Humanos , Rayos UltravioletaRESUMEN
Six new ursane-type triterpenes with a phenylpropanoid unit and five known oleanane-type triterpenes were isolated from the leaves of Camellia ptilosperma. The undescribed compounds were identified by analysis of 1D and 2D NMR and HRESIMS spectroscopic data as ptilospermanols A-F. The cytotoxicity of new compounds against six human cancer cell lines and three mouse tumor cell lines was evaluated by MTT assay.
Asunto(s)
Antineoplásicos Fitogénicos , Antineoplásicos , Camellia , Triterpenos , Humanos , Animales , Ratones , Triterpenos/farmacología , Triterpenos/química , Camellia/química , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Estructura Molecular , Línea Celular TumoralRESUMEN
BACKGROUND: Flavonoid glycosides are known to possess diverse bioactivities including antitumor and anti-inflammatory properties. Hesperetin is abundant in nature and can be used to synthesize bioactive flavonoids. This has the advantages of low cost, short synthetic steps, simple operation, and good yields. OBJECTIVE: In this study, we aimed to synthesize bioactive flavonoids and flavonoid glycosides from hesperetin and evaluate the antitumor and anti-inflammatory activities of these compounds. METHODS: A series of flavonoids and their derivatives were synthesized by methoxylation, oxidative dehydrogenation, benzylation, debenzylation, and deacetylation as well as using a modified peroxyacetone method and a glycoside condensation reaction. Their anti-inflammatory activities were evaluated for their inhibitory effects on nitric oxide (NO), tumor necrosis factor (TNF-α), and interleukin-6 (IL-6) production in LPS-induced RAW264.7 mouse macrophages. Their structures were characterized by HRMS, 1 H-NMR, and 13 C-NMR, and their cytotoxicity on the human triple-negative breast cancer cell (TNBC) line, SUM 149, was tested by using the MST assay. RESULTS: Most of the compounds markedly reduced NO production in LPS-stimulated murine macrophages at the tested concentrations in a dose-dependent manner. Among these, compounds 1, 7, 9, and 17 showed significant anti-inflammatory activities against NO production in LPS-induced RAW264.7 mouse macrophages. In addition, they could also reduce the release of TNF-α and IL-6 in a concentration-dependent manner. Most of the tested compounds showed remarkable anti-human TNBC activities. Compounds 1b-1m, 1, and 3 showed a certain degree of growth inhibition effect on the human TNBC cell lines and their IC50 values were all below 16.61â µM. In addition, compound 1l was the most cytotoxic with IC50 values of 1.38±0.31â µM, while the other compounds were inactive with inhibition rates <50 % at the highest concentration tested (20â µM). CONCLUSIONS: A novel series of flavonoids were synthesized from the natural flavonoid, hesperetin, including 17 new compounds. Screening tests indicated that most of these compounds reduced NO production in LPS-stimulated murine macrophages at concentrations of 15 to 60â µM, and the inhibition generally increased in a dose-dependent manner. Some compounds showed different degrees of cytotoxicity on the human TBNC cell lines, SUM 149.
Asunto(s)
Flavonoides , Neoplasias de la Mama Triple Negativas , Ratones , Animales , Humanos , Flavonoides/química , Glicósidos/farmacología , Factor de Necrosis Tumoral alfa/metabolismo , Interleucina-6/metabolismo , Lipopolisacáridos/farmacología , Antiinflamatorios/farmacología , Óxido NítricoRESUMEN
Triple-negative breast cancer (TNBC) is the most aggressive subtype of breast cancer. Many studies have shown a significant increase in the marker signal of the receptor for advanced glycation end-products (RAGE) with the malignant progression of tumor growth, metastasis and recurrence of breast cancer, including TNBC of primary tumors and lymph node metastases. Azeliragon is a RAGE inhibitor and it has been shown to actively inhibit the TNBC cell line, SUM149 (IC50 = 5.292 ± 0.310 µM). In order to develop a new anti-TNBC agent, we designed, synthesized and screened 26 Azeliragon triazole analogues to determine their anti-TNBC activities in vitro. The most active compound was KC-10 with an IC50 value of 0.220 ± 0.034 µM.
Asunto(s)
Antineoplásicos/farmacología , Diseño de Fármacos , Imidazoles/farmacología , Triazoles/farmacología , Neoplasias de la Mama Triple Negativas/tratamiento farmacológico , Antineoplásicos/síntesis química , Antineoplásicos/química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Productos Finales de Glicación Avanzada/antagonistas & inhibidores , Productos Finales de Glicación Avanzada/metabolismo , Humanos , Imidazoles/síntesis química , Imidazoles/química , Estructura Molecular , Relación Estructura-Actividad , Triazoles/síntesis química , Triazoles/química , Neoplasias de la Mama Triple Negativas/patologíaRESUMEN
Two new flavonoid glycosides were isolated from the aerial parts of Nervilia fordii by various chromatographies such as D101 macroporous resin, ODS and preparative HPLC chromatographic techniques. Their structures were elucidated as rhamnocitrin-3-O-ß-glucopyranosyl-4'-O-ß-galactosyl-(1â3)-glucopyranoside(1) and 7,3'-di-O-methylquercetin-4'-O-[ß-galactosyl-(1â3)-ß-glucopyranosyl]-3-O-ß-glucopyranoside(2) on the basis of extensive spectroscopic analyses, including 1D-, 2D-NMR, HR-ESI-MS and analytical hydrolysis.
Asunto(s)
Flavonoides/aislamiento & purificación , Glicósidos/aislamiento & purificación , Orchidaceae/química , Cromatografía Líquida de Alta Presión , Medicamentos Herbarios Chinos/química , Hidrólisis , Estructura MolecularRESUMEN
To study the chemical constituents of Nervilia fordii (Hance) Schltr., various chromatographic methods were used, including D101 macroporous resin, silica gel, ODS and preparative HPLC chromatographic techniques. A new labdane diterpenoid glycoside named as nervilifordoside A was isolated from 60% EtOH extract of Nerviliafordii. The structure of compound 1 was elucidated as 12, 17-epoxy-3-hydroxy-17-methoxy-labdan-13-en-16, 15-olide 3-O-alpha-rhamnopyranosyl-(1 --> 2)-O-beta-glucopyranoside on the basis of HR-MS, 1D and 2D NMR spectroscopic data as well as chemical methods.
Asunto(s)
Orchidaceae/química , Plantas Medicinales/química , Cromatografía Líquida de Alta Presión , Estructura MolecularRESUMEN
Five new flavonoid glycosides, namely nervilifordins F-J (1-5), were isolated from the 60% EtOH extract of the aerial parts of Nervilia fordii, along with three first isolated flavonoids (7, 8, and 13) and five known flavonoids (6, 9-12). The structures of new compounds were elucidated on the basis of 1D and 2D NMR and MS studies. Their anti-inflammatory activities were tested by measuring their inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages. Compounds 2 and 5 showed interesting inhibition effects with their EC50 values of 15.15 µM and 14.80 µM, respectively.
Asunto(s)
Antiinflamatorios/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Flavonoides/aislamiento & purificación , Glicósidos/aislamiento & purificación , Animales , Antiinflamatorios/química , Antiinflamatorios/farmacología , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Flavonoides/química , Flavonoides/farmacología , Glicósidos/química , Glicósidos/farmacología , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Resonancia Magnética Nuclear Biomolecular , Orchidaceae/químicaRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Viburnum taitoense Hayata has been used as folk medicine by the minority people in Southwestern China for a long history, especially in Guangxi Zhuang Autonomous Region. The minority in Guangxi including Zhuang, Miao and Yao people use the ethanol extract of V. taitoense Hayata to treat the fracture, kill the pain of rheumatism because of its definite therapeutic effects. AIM OF THE STUDY: So far, the scientific investigation of V. taitoense Hayata is done very little. Here, we first prepared the ethyl acetate extract of V. taitoense (EEVt), secondly measured the contents of phenols, flavonoids, and terpenoids in EEVt, and thirdly, the anti-inflammatory and analgesic activities of EEVt were investigated by invitro model of RAW 264.7 cells and invivo models of inflammation and pain in rats and mice. MATERIALS AND METHODS: The contents of phenols, flavonoids, and terpenoids in EEVt were determined by UV spectrophotometry, respectively. The anti-inflammatory effect of EEVt (5, 25, 50, 100, and 200 µg/mL) in vitro was tested by determining its inhibitory effect on the nitric oxide production of RAW264.7 cells activated by lipopolysaccharide (LPS). The anti-inflammatory and analgesic effects of EEVt in vivo were investigated in the following experimental rats and mice models: carrageenan-induced paw edema, corton-oil-induced ear edema, acetic acid writhing test, and formalin pain test. RESULTS: The contents of total phenolic, total flavonoids, and total triterpenoids in V. taitoense were measured to be 3.46 ± 0.04%, 2.38 ± 0.04%, and 14.96 ± 0.17%, respectively. In vitro test showed that EEVt at different tested dosages (5, 25, 50, 100, and 200 µg/mL) had no significant toxicity to RAW264.7 macrophages. At dosages of 37.5 and 75 µg/mL of EEVt significant inhibitory (p < 0.001) on the productions of nitric oxide (NO). High dosage (200 µg/mL) of EEVt displayed highly significant inhibitory (p < 0.001) on the productions of proinflammatory cytokines IL-6, IL-1ß, and TNF-α from the LPS-induced RAW264.7 macrophages. EEVt showed obvious anti-inflammatory activity at different time points after carrageenan injection (p < 0.05) in vivo test, and its anti-inflammatory activity reached the strongest 4 h. Similarly, through the ear swelling test, EEVt (200 mg/kg) showed significant (p < 0.05) anti-inflammatory activity. Besides, formalin and acetic acid writhing experiments also showed that EEVt has significant (p < 0.05) analgesic activity. CONCLUSION: EEVt was confirmed to be definite anti-inflammatory and analgesic effects, and the phytochemicals of EEVt was disclosed to be rich in triterpenoids, which was worthy to be further investigated.
Asunto(s)
Analgésicos/farmacología , Antiinflamatorios/farmacología , Inflamación/tratamiento farmacológico , Dolor/tratamiento farmacológico , Extractos Vegetales/farmacología , Viburnum/química , Acetatos/química , Analgésicos/uso terapéutico , Animales , Antiinflamatorios/uso terapéutico , Conducta Animal/efectos de los fármacos , Carragenina/toxicidad , China , Citocinas/antagonistas & inhibidores , Modelos Animales de Enfermedad , Edema/inducido químicamente , Edema/tratamiento farmacológico , Flavonoides/análisis , Flavonoides/química , Formaldehído/toxicidad , Inflamación/inducido químicamente , Lipopolisacáridos/toxicidad , Medicina Tradicional/métodos , Ratones , Óxido Nítrico/antagonistas & inhibidores , Dolor/inducido químicamente , Fenoles/análisis , Fenoles/química , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , Células RAW 264.7 , Ratas Sprague-Dawley , Terpenos/análisis , Terpenos/químicaRESUMEN
Five previously undescribed lanostane-type triterpenoids, including two triterpenoids with a rearranged side chain (applanoic acids E and F), one C21 nortriterpenoid (16,17-dehydroapplanone E), as well as two highly oxygenated lanostane triterpenoids (methyl applaniate B and applanoic acid G), were isolated from the fruiting bodies of Ganoderma applanatum (Pers.) Pat. Their structures were elucidated on the basis of spectroscopic analysis, X-ray crystallography and ECD data. Applanoic acid E, 16,17-dehydroapplanone E, and methyl applaniate B showed inhibitory effects on the release of NO by LPS-induced BV-2 cells.
Asunto(s)
Ganoderma , Triterpenos , Cuerpos Fructíferos de los Hongos , Lipopolisacáridos , Estructura MolecularRESUMEN
Nervilia fordii (Hance) Schltr. has been widely used as a medicinal and edible herb in Southwest China and Southeast Asia. In this study, NFP-1, a new water-soluble polysaccharidewith a purity of 97.8%, was purified from water extract of Nervilia fordii by DEAE-cellulose and Sephadex G-100 chromatography. NFP-1 has a relative molecular weight of 950â¯kDa determined by high performance gel-permeation chromatography (HPGPC). Its monosaccharide compositions were analyzed by high performance liquid chromatography (HPLC) after pre-column derivatizing its hydrolysate with 1-phenyl-3-methyl-5-pyrazolone (PMP). NFP-1 mainly consists of galactose, arabinose, rhamnose, and galacturonic acid. Based on FT-IR, methylation and GC-MS analysis, and NMR, the structure unit of NFP-1 was established as â4)-α-Rhap-(2â 4)-α-GalpA-(1â2)-α-Rhap-(1â2)-α-Rhap-(4â1)-ß-Galp-T containing two branch chains of â2,4)-α-Rhap-(1â5)-α-Araf-(1â3)-α-Araf-(1â, and â2,4)-α-Rhap-(1â4)-ß-Galp-(1â. The immunomodulatory assays revealed the dual-functionalities of NFP-1. NFP-1 could significantly induce the secretion of nitric oxide (NO), and promote the secretions of TNF-α, IL-6, and IL-1ß in RAW264.7 macrophages. NFP-1 could also significantly inhibit the production of NO, depress the secretions of TNF-α, IL-6 and IL-1ß in RAW264.7 macrophages activated by lipopolysaccharide (LPS), and promote the production of IL-10 meanwhile. Our study suggested that Nervilia fordii could be an ideal medicinal or functional food due to its dual immunomodulatory activities.