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ETHNOPHARMACOLOGICAL RELEVANCE: The traditional Chinese medicine (TCM) "Shihu" has a long history of medicinal use in China from some species of Dendrobium. D. officinale is a major source of "Shihu" and is widely cultivated in south of China and listed separately as "Tiepi Shihu" by the Chinese Pharmacopoeia in now time. Traditionally, D. officinale has been widely used in daily health care and the treatment of diabetes and gastrointestinal diseases. AIM OF THIS REVIEW: In order to better develop and utilize D. officinale, we conducted this systematic review of previous studies, showed clear structure of all isolates from D. officinale together with pharmacological progress, hoping to provide references for further research and utilization. In addition, specific display of the chemical components and the research progress of related activities can help to better understand the traditional records and modern pharmaceutical applications of the plant medicine. MATERIALS AND METHODS: Information on phytochemistry and pharmacological studies of D. officinale was collected from various scientific databases including Web of Science, SciFinder, ACS, Springer, Scopus, PubMed, ScienceDirect, Google Scholar and CNKI. RESULTS: More than 180 compounds isolated from D. officinale, including bibenzyls, phenols, phenylpropanoids, lignans, flavonoids and polysaccharides are listed in this review. Furthermore, modern pharmacological researches such as hypoglycemia, immune regulation, antioxidant, cardiovascular regulation and gastrointestinal protection are summarized. CONCLUSION: Based on the summary of the research work of D. officinale, we systematically show the chemical composition of the plant, and concluded the relationship of those composition with plant habitat together with the relationship between the structure of chemical components and pharmacological activity. Moreover, we suggest that some of small molecule compounds could also be quality control of D. officinale besides polysaccharides.
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Bibencilos , Dendrobium , Medicamentos Herbarios Chinos , Dendrobium/química , Medicina Tradicional China , Medicamentos Herbarios Chinos/farmacología , Control de Calidad , Fitoquímicos/farmacología , Fitoquímicos/uso terapéutico , EtnofarmacologíaRESUMEN
The aerial part of âRubia cordifolia âL. has been used as an herbal medicine for a long time with various pharmacological activities, including anti-inflammatory, anticancer, and antibacterial activities. The most notable usage of these was that this herbal medicine had good therapeutic effects on diarrhea caused by various factors. However, the mechanism for the ethanolic extract of âR. cordifolia âL. (RCEE) to treat Ulcerative colitis (UC) effectively is still unclear. In this study, DSS successfully induced UC mice and then intervene using different polar parts of RCEE. The results indicated that RCEE-treatment inhibited colonic combination NLRP3 inflammasome formation and IL-6/JAK2/STAT3 activation in vivo, significantly ameliorating the clinical symptoms, including alleviating colonic mucosal damage and infiltration of macrophages, suppressing the release of inflammatory cytokines, and reducing mortality. Taken together, this study suggests that dual inhibition of NLRP3 inflammasome and IL-6/JAK2/STAT3 pathways activation using RCEE may be a promising therapeutic strategy for preventing the progression of UC.
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Dendrobium officinale is a valuable medicinal herb that is widely used in traditional Chinese medicine. The chemical constituents of D. officinale have attracted much attention and a large number of compounds have been reported including many bibenzyl derivatives. 13 bibenzyl derivatives from D. officinale were sent for molecular docking, surface plasmon resonance (SPR) assay and after detection of Mn-SOD and SIRT3 activities in or not in HaCaT cells, it was concluded that bibenzyl derivatives did not directly activate Mn-SOD but promoted SIRT3 proteins. In addition, HaCaT cells were irradiated with UV-B to induce an oxidative stress model in vitro to further verify the effect of bibenzyl derivatives. The results show that bibenzyl derivatives could directly bind to SIRT3, enhance the deacetylation and then activate Mn-SOD, so as to protect UV-B induced skin photoaging.
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The Dendrobium plants (members of the Orchidaceae family) are used as traditional Chinese medicinal herbs. Bibenzyl, one of the active compounds in Dendrobium officinale, occurs in low amounts among different tissues. However, market demands require a higher content of thes compounds to meet the threshold for drug production. There is, therefore, an immediate need to dissect the physiological and molecular mechanisms underlying how bibenzyl compounds are biosynthesized in D. officinale tissues. In this study, the accumulation of erianin and gigantol in tissues were studied as representative compounds of bibenzyl. Exogenous application of Methyl-Jasmonate (MeJA) promotes the biosynthesis of bibenzyl compounds; therefore, transcriptomic analyses were conducted between D. officinale-treated root tissues and a control. Our results show that the root tissues contained the highest content of bibenzyl (erianin and gigantol). We identified 1342 differentially expressed genes (DEGs) with 912 up-regulated and 430 down-regulated genes in our transcriptome dataset. Most of the identified DEGs are functionally involved in the JA signaling pathway and the biosynthesis of secondary metabolites. We also identified two candidate cytochrome P450 genes and nine other enzymatic genes functionally involved in bibenzyl biosynthesis. Our study provides insights on the identification of critical genes associated with bibenzyl biosynthesis and accumulation in Dendrobium plants, paving the way for future research on dissecting the physiological and molecular mechanisms of bibenzyl synthesis in plants as well as guide genetic engineering for the improvement of Dendrobium varieties through increasing bibenzyl content for drug production and industrialization.
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Dry eye is currently one of the most common ocular surface disease. It can lead to ocular discomfort and even cause visual impairment, which greatly affects the work and quality of life of patients. With the increasing incidence of dry eye disease (DED) in recent years, the disease is receiving more and more attention, and has become one of the hot research fields in ophthalmology research. Recently, with the in-depth research on the etiology, pathogenesis and treatment of DED, it has been shown that defects in immune regulation is one of the main pathological mechanisms of DED. Since the non-specific and specific immune response of the ocular surface are jointly regulated, a variety of immune cells and inflammatory factors are involved in the development of DED. The conventional treatment of DED is the application of artificial tears for lubricating the ocular surface. However, for moderate-to-severe DED, treatment with anti-inflammatory drugs is necessary. In this review, the immunomodulatory mechanisms of DED and the latest research progress of its related treatments including Chinese medicine will be discussed.
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Two new sesquiterpenoids, including a kessane-type sesquiterpenoid (1) and one bisabolane derivative (2), together with fourteen known sesquiterpenoids (3-16), were isolated from the roots and rhizomes of Valeriana amurensis. The structures of new compounds were established on the basis of extensive spectroscopic analysis. All isolates were evaluated for their effects on nerve growth factor (NGF)-mediated neurite outgrowth in pheochromocytoma (PC12) cells. As a results, four compounds including 10-12 and 15 showed potent promoting effects at the concentration of 10 µM on NGF-induced neurite outgrowth in PC12 cells with the differentiation rate of 11.84%, 12.21%, 13.77% and 12.16%, respectively.
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Factor de Crecimiento Nervioso/farmacología , Proyección Neuronal/efectos de los fármacos , Raíces de Plantas/química , Rizoma/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Valeriana/química , Animales , Espectroscopía de Resonancia Magnética con Carbono-13 , Factor de Crecimiento Nervioso/metabolismo , Células PC12 , Espectroscopía de Protones por Resonancia Magnética , Ratas , Sesquiterpenos/químicaRESUMEN
The cortex root of Paeonia ostii, is used as a traditional Chinese medicine for treating female diseases. Phytochemical investigation of the water-soluble fraction of the plant led to the isolation of two new acetoisovanillone glycosides: acetoisovanillone-3-O-ß-D-glucopyranoside (1) and 2-hydroxy-acetoisovanillone-3-O-ß-D-glucopyranoside (2). Their structures were elucidated by extensive spectroscopic methods.
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Glicósidos/química , Paeonia , Femenino , Glicósidos/aislamiento & purificación , Humanos , Medicina Tradicional China , AguaRESUMEN
Pleiones are popular ornamental orchids and different species of Pleione are long being used as traditional medicine in many Asian countries. However, previous chemical investigations of the genus Pleione are restricted to only a few species. In the present study, high performance liquid chromatography (HPLC) fingerprint of Pleione plants was established, which in particular, eight common peaks were confirmed in 16 species/hybrids. Three of the compounds corresponding to the chromatographic peaks were identified by electrospray ionization tandem mass spectrometry (ESI-tandem-MS). HPLC analysis confirmed the studied taxa shared most of chemical compounds but the content of chemical compounds was significantly different between species. Comparison of hierarchical clustering result with phylogenetic tree revealed that closely related species have higher similarities in chemical constituents. In consideration of low chemical similarity between spring-flowering and autumn-flowering species, we suggest a discrimination of these two groups during medicinal use of the genus Pleione. Species with a large pseudobulb and with high content of a certain compound should be given priority in future artificial cultivation and medicinal cultivar breeding. We hope our findings will contribute to the quality control and promote conservation of such endangered plant group.
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Orchidaceae/química , Extractos Vegetales/química , Cromatografía Líquida de Alta Presión , Análisis por Conglomerados , Flores/anatomía & histología , Flores/química , Flores/metabolismo , Orchidaceae/clasificación , Orchidaceae/metabolismo , Filogenia , Plantas Medicinales/química , Plantas Medicinales/clasificación , Plantas Medicinales/metabolismo , Análisis de Componente Principal , Estaciones del Año , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Two polysaccharides, named DOP-1 and DOP-2, with molecular weights of 6.8 kDa and 14.3 kDa, respectively, were isolated and purified from the stems of Dendrobium officinale. Monosaccharide composition, Fourier-transform infrared spectroscopy, methylation, and nuclear magnetic resonance analyses indicated that DOP-1 and DOP-2 may have a backbone consisted of â4)-ß-d-Glcp-(1â, â4)-ß-d-Manp-(1â, â4)-2-O-acetyl-ß-d-Manp-(1â and â4)-3-O-acetyl-ß-d-Manp-(1â. In vivo assays showed that D. officinale polysaccharides (DOPs) exerted significant hypoglycemic effects accompanying increased serum insulin and glucagon-like peptide-1 (GLP-1) levels in streptozotocin-induced diabetic rats. Further in vitro experiments showed that DOP-induced GLP-1 secretion was inhibited by an intracellular calcium chelator, a Ca2+/calmodulin-dependent protein kinase (CaMK) II inhibitor, a specific calcium-sensing receptor antagonist, and a p38-mitogen-activated protein kinases (MAPK) inhibitor. These results indicated that DOPs may decrease fasting blood sugar levels by stimulating GLP-1 secretion and that intracellular DOP-induced GLP-1 secretion involved the Ca2+/calmodulin/CaMKII and MAPK pathways.
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Dendrobium/química , Diabetes Mellitus Experimental/tratamiento farmacológico , Péptido 1 Similar al Glucagón , Hipoglucemiantes , Extractos Vegetales , Polisacáridos , Animales , Línea Celular , Péptido 1 Similar al Glucagón/sangre , Péptido 1 Similar al Glucagón/metabolismo , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Secreción de Insulina , Masculino , Ratones , Extractos Vegetales/química , Extractos Vegetales/farmacología , Polisacáridos/química , Polisacáridos/farmacología , Ratas , Ratas Sprague-DawleyRESUMEN
Two unusual dendrobine-type alkaloids, findlayines E and F (1, 2), along with five known dendrobine-type alkaloids (3-7), were isolated from the stems of Dendrobium findlayanum Par. et Rchb. f. Compound 1 is the first example of dendrobine-type alkaloids with a 2-ethoxy-2-oxoethyl group attaching to the C-2, and compound 2 is a nor-dendrobine-type alkaloid, featuring a 5-decarboxylated structure. The structures of compounds 1 and 2 were elucidated by means of extensive spectroscopic analyses, and their absolute configuration were confirmed by electronic circular dichroism (ECD) calculations. All isolates were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549 and MCF-7 human cancer cells.
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Alcaloides/farmacología , Dendrobium/química , Tallos de la Planta/química , Células A549 , Alcaloides/aislamiento & purificación , China , Células HL-60 , Humanos , Células MCF-7 , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacologíaRESUMEN
Three new sesquiterpene glycosides with alloaromadendrane and ylangene-derived type aglycones, named dendrofindlayanosides A-C (1-3), one new cyclopacamphane type sesquiterpene named dendrofindlayanobilin A (4), together with five known compounds have been isolated from stems of Dendrobium findlayanum. Their structures were determined on the basis of spectroscopic and chemical methods.
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Dendrobium/química , Plantas Medicinales/química , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , China , Espectroscopía de Resonancia Magnética , Estructura Molecular , Tallos de la Planta/químicaRESUMEN
The stems of Dryopteris crassirhizoma, one of the main components of Lianhua-Qingwen Formula (LQF) was traditionally used for heat-clearing and detoxifying. Dryocrassin ABBA is a key antiviral component in the herbal medicine while the compound is hard to get in large amounts with the features of homologous compounds, polyphenol groups, and low contents. Therefore, the present work aims to seek influenza H7N9 virus inhibitors from natural source by synthesis of dryocrassin ABBA and its analogues. As a result, total synthesis of the compound was achieved in nine steps with an over-all yield of 4.6%. Neuraminidases (NAs) inhibitory activities of the synthesized product and its analogues were evaluated afterward. Comparing with the positive control, OSV (9.6⯵M), it was very exciting that dryocrassin ABBA and its analogues (b5 and e2) showed better NAs inhibitory activity against Anhui H7N9 with IC50 values of 3.6⯵M, 2.5⯵M and 1.6⯵M. For the highly resistant Shanghai N9, these compounds can also show medium inhibitory activities. Docking results indicated the direct interaction of synthesized 3 hits with the key K294 by hydrogen bonds, but no direct interaction of OSV with the key K294 was observed in Shanghai N9. This study suggested that dryocrassin ABBA and its analogues especially AB, which consisted of polyphenol groups may have beneficial effects on treating avian influenza H7N9 virus.
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Antivirales/farmacología , Compuestos de Bencilideno/farmacología , Ciclohexanonas/farmacología , Farmacorresistencia Viral/efectos de los fármacos , Inhibidores Enzimáticos/farmacología , Subtipo H7N9 del Virus de la Influenza A/efectos de los fármacos , Neuraminidasa/antagonistas & inhibidores , Antivirales/síntesis química , Antivirales/química , Compuestos de Bencilideno/síntesis química , Compuestos de Bencilideno/química , Ciclohexanonas/síntesis química , Ciclohexanonas/química , Relación Dosis-Respuesta a Droga , Dryopteris/química , Inhibidores Enzimáticos/síntesis química , Inhibidores Enzimáticos/química , Subtipo H7N9 del Virus de la Influenza A/enzimología , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Estructura Molecular , Neuraminidasa/metabolismo , Relación Estructura-ActividadRESUMEN
One hitherto unknown 24-nor-13,27-cycloursane-type triterpenoid, lucumic acid A (1), one new 24-nor-ursane triterpenoid, lucumic acid B (2), along with six known triterpenoids were isolated from the ethanol extract of the leaves of Lucuma nervosa. Their structures were established on the basis of spectroscopic data interpretation. Lucumic acid A (1) is the first example of a 24-nor-triterpenoid with a 13,27-cyclopropane ring.
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Ácido Oleanólico/análogos & derivados , Hojas de la Planta/química , Pouteria/química , Triterpenos/aislamiento & purificación , China , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/farmacología , Estructura Molecular , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/farmacología , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/química , Triterpenos/farmacologíaRESUMEN
Four new monoterpenoids, including two new acyclic monoterpenoids (2R, 6R)-2, 6-dimethyl-8-isovaleroxyoctan-1-ol (1) and (2S, 6S)-2, 6-dimethyl-8-isovaleroxyoctan-1-ol (2), as well as two new iridoids stenopterins F-G (3 and 4), together with fifteen known compounds (5-19), were isolated from whole dried material of Valeriana stenoptera. Stenopterin F was the first reported iridoids with n-butoxyl in the Valerianaceae family. The structures of new compounds were established on the basis of extensive spectroscopic analysis.
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Monoterpenos/química , Valeriana/química , Estructura MolecularRESUMEN
2,3-O-acetylated-1,4-ß-d-glucomannan (DOP-1-1) is a polysaccharide isolated from the stem of Dendrobium officinale. DOP-1-1 has been demonstrated to have remarkable immunomodulatory properties, but little is known about the influence of its structural diversity on bioactivity (and even less about the exact mechanism underlying its immune responses). First, DOP-1-1 was stabilized at different temperatures and pH conditions based on differential scanning calorimetry and size exclusion-chromatographyâ»high-performance liquid chromatography. Then, a detailed study on the effects of DOP-1-1 on a human leukemia monocytic cell line (THP-1) under normal conditions was undertaken. DOP-1-1 promoted the translocation of nuclear factor-kappa B (NF-κB) and degradation of IκB proteins. The expression of genes and proteins closely associated with the immune, survival and apoptotic functions of NF-κB were analyzed by quantitative real-time RT-PCR. Furthermore, CCL4 and IP10 were confirmed to be the novel targets of the immune response stimulated by DOP-1-1. The phosphorylation of NF-кB was inhibited by treatment with a toll-like receptor 4 (TLR4) antagonist (TAK-242) and myeloid differentiation factor 88 (MyD88) inhibitor (ST2825). These data suggested: (i) the O-acetylated glucomannan DOP-1-1 is present in the steady state in low-pH solutions; (ii) DOP-1-1 can induce an immune response through NF-кB mediated by a TLR4 signaling pathway; and (iii) CCL4 and IP10 could be the novel targets of the immune response stimulated by O-acetylated glucomannan.
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Dendrobium/química , Inmunidad/efectos de los fármacos , Mananos/farmacología , FN-kappa B/metabolismo , Receptor Toll-Like 4/metabolismo , Acetilación , Rastreo Diferencial de Calorimetría , Quimiocina CCL4/genética , Quimiocina CCL4/metabolismo , Cromatografía en Gel , Relación Dosis-Respuesta a Droga , Regulación de la Expresión Génica/efectos de los fármacos , Humanos , Mananos/química , Estructura Molecular , Fosforilación/efectos de los fármacos , Extractos Vegetales/química , Extractos Vegetales/farmacología , Transporte de Proteínas/efectos de los fármacos , Células THP-1RESUMEN
The roots and rhizomes of Valeriana jatamansi have long been used as folk medicine in Asia and usually named as "Zhizhuxiang" in Chinese for the treatment of abdominal distention and pain. However, its active ingredients and molecular targets for treatment of abdominal pain remain unrevealed. Inhibitors of Cav2.2 N-type voltage-gated calcium channels (VGCCs) are actively sought after for their potential in treating pain, especially chronic pain. As far as we know, the method used for seeking analgesic active ingredient from plant material has rarely been reported. The analgesic potentials of the EtOH extract (0.01 mg/ml) of the roots and rhizomes of V. jatamansi and its EtOAc, n-BuOH and H2O soluble parts (0.01 mg/ml, respectively) were tested herein on Cav2.2, using whole-oocyte recordings in vitro by tow-electrode voltage clamp. The results indicated that the EtOAc-soluble part exhibited the most potent inhibition of Cav2.2 peak current (20 mv). The EtOAc-soluble part was then subjected to silica gel column chromatography (CC) and giving 9 fractions. Phytochemical studies were carried out by repeated CC and extensive spectroscopic analyses after the fraction (0.01 mg/ml) was identified to be active and got seventeen compounds (1-17). All isolates were then sent for further bioactive verification (1 and 3 at concentration of 10 µM, others at 30 µM). In addition, the selectivity of the active compounds 1 and 3 were tested on various ion channels including Cav1.2, Cav2.1 and Cav3.1 VGCCs and Kv1.2, Kv2.1, Kv3.1 and BK potassium channels. The results indicated that compound 1 and 3 (an abundant compound) inhibited Cav2.2 with an EC50 of 3.3 and 4.8 µM, respectively, and had weaker or no effect on Cav1.2, Cav2.1 and Cav3.1 VGCCs and Kv1.2, Kv2.1, Kv3.1 and BK potassium channels. Compounds 1 and 3 appear to act as allosteric modulators rather than pore blockers of Cav2.2, which may play crucial role in attenuating nociception. The results of present research indicated that the ethnopharmacological utilization of V. jatamansi for relieving the abdominal distention and pain may mediate through Cav2.2 channel. Our work is the first demonstration of inhibition of Cav2.2 by iridoids, which may provide a fresh source for finding new analgesics.
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Dendrobii Caulis (DC), named 'Shihu' in Chinese, is a precious herb in traditional Chinese medicine. It is widely used to nourish stomach, enhance body fluid production, tonify "Yin" and reduce heat. More than thirty Dendrobium species are used as folk medicine. Some compounds from DC exhibit inhibitory effects on macrophage inflammation. In the present study, we compared the anti-inflammatory effects among eight Dendrobium species. The results provided evidences to support Dendrobium as folk medicine, which exerted its medicinal function partially by its inhibitory effects on inflammation. To investigate the anti-inflammatory effect of Dendrobium species, mouse macrophage cell line RAW264.7 was activated by lipopolysaccharide. The nitric oxide (NO) level was measured using Griess reagent while the pro-inflammatory cytokines were tested by ELISA. The protein expressions of inducible NO synthase (iNOS), cyclooxygenase-2 (COX-2) and mitogen-activated protein kinases (MAPKs) phosphorylation were evaluated by Western blotting analysis. Among the eight Dendrobium species, both water extracts of D. thyrsiflorum B.S.Williams (DTW) and D. chrysotoxum Lindl (DCHW) showed most significant inhibitory effects on NO production in a concentration-dependent manner. DTW also significantly reduced TNF-α, MCP-1, and IL-6 production. Further investigations showed that DTW suppressed iNOS and COX-2 expression as well as ERK and JNK phosphorylation, suggesting that the inhibitory effects of DTW on LPS-induced macrophage inflammation was through the suppression of MAPK pathways. In conclusion, D. thyrsiflorum B.S.Williams was demonstrated to have potential to be used as alternative or adjuvant therapy for inflammation.
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Dendrobium/química , Regulación Enzimológica de la Expresión Génica/efectos de los fármacos , Inflamación/inducido químicamente , Lipopolisacáridos , Macrófagos , Proteínas Quinasas Activadas por Mitógenos/antagonistas & inhibidores , Extractos Vegetales/farmacología , Animales , Antiinflamatorios/farmacología , Ciclooxigenasa 2/genética , Citocinas/metabolismo , Inflamación/tratamiento farmacológico , Macrófagos/efectos de los fármacos , Macrófagos/enzimología , Ratones , Proteínas Quinasas Activadas por Mitógenos/genética , Proteínas Quinasas Activadas por Mitógenos/metabolismo , Óxido Nítrico/análisis , Óxido Nítrico Sintasa de Tipo II/genética , Fosforilación/efectos de los fármacos , Células RAW 264.7 , Transducción de Señal/efectos de los fármacosRESUMEN
Ten previously undescribed stilbenoids, including six bibenzyls (bleochrins A-F, 1-6), three phenanthrenes derivatives (bleochrins G-J, 7-10) along with eleven known compounds were isolated from the rhizomes of Bletilla ochracea Schltr. The structural characterizations of 1-21 were accomplished by spectroscopic data, while the absolute stereostructure of 6 was confirmed by electronic circular dichroism (ECD) data analyses. All isolated metabolites except 7 were evaluated for cytotoxic activity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480). Four isolates exhibited significant inhibitory ability against HL-60, SMMC-7721, and MCF-7 cell lines, with IC50 values ranging from 0.79 to 6.57⯵M. The isolates were tested further for inhibitory effects on the NO production of the liposaccharide (LPS)-induced RAW264.7 macrophages and showed activity with IC50 values at 15.29-24.02⯵M.
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Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Bibencilos/farmacología , Orchidaceae/química , Fenantrenos/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Bibencilos/aislamiento & purificación , Línea Celular Tumoral , China , Humanos , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Fenantrenos/aislamiento & purificación , Células RAW 264.7 , Rizoma/químicaRESUMEN
Four new dihydrophenanthrenofuran, bleochranols A-D (1-4), along with 21 known compounds including phenanthrenes (5-14) and bibenzyls (15-25) were isolated and elucidated from the rhizomes of Bletilla ochracea. Combination of 1D/2D NMR techniques and the Electronic Circular Dichroism (ECD) spectroscopy based on the empirical helicity rules, chemical structure of those isolates were determined. All the compounds were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7 and SW480 human cancer cell lines by MTS assay and anti-inflammatory activity by nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. Among the 25 tested compounds, bleochranol A (1) showed remarkable cytotoxic activity against HL-60, A-549, and MCF-7 with IC50 values of 0.24⯱â¯0.03, 3.51⯱â¯0.09 and 3.30⯱â¯0.99⯵M respectively. The anti-inflammatory assay showed that compound 12 exhibited most potential activity against NO production in RAW 264.7 macrophages with IC50 2.86⯱â¯0.17⯵M. The results indicated that the main chemical constituents of B. ochracea were phenanthrene and bibenzyl and similar to that of B. striata.
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Antiinflamatorios/aislamiento & purificación , Orchidaceae/química , Estilbenos/aislamiento & purificación , Animales , Antiinflamatorios/farmacología , Bibencilos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Fenantrenos/aislamiento & purificación , Extractos Vegetales/química , Células RAW 264.7 , Rizoma/química , Estilbenos/farmacologíaRESUMEN
A new bibenzyl derivative, dendrocandin V (1) and a new sesquiterpene amino ether, wardianumine A (2), together with eleven known compounds, including phenanthrenes (denbinobin (3), 9,10-dihydro-denbinobin (4), mostatin (5), loddigesiinols A (6)), bibenzyls (moscatilin (7), 5-hydroxy-3,4'-dimethoxybibenzyl (8), 3,4-dihydroxy-5,4'-dimethoxy bibenzyl (9), dendrocandin A (10), gigantol (11), dendrocandin U (12)) and an alkaloids (dihydroshihunine, 13) were isolated from the EtOH extraction of stems of Dendrobium wardianum Warner. Isolation of the new compound 2 indicated that N,N-dimethylethanolamine as the key adduction in the synthesis of dendroxine and its analogs in Dendrobium species. The hypothetical biosynthetic pathway of 2 was then postulated. Inspired by literature and traditional usage of the herbal medicine, some compounds were sent for cytotoxic activity and the results indicated that compounds 1, 3, 4, 5 showed cytotoxic activities against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480) with IC50 from 2.33-38.48µM. Among those compounds, 3 and 4 showed cell line selectivity with strong activity comparable to DDP.