Hepatophyta
Erianin induces apoptosis in human leukemia HL-60 cells. (1/44)
AIM: To investigate the effect of erianin on human HL-60 cell line and explore its mechanism of apoptosis in vitro. METHODS: Inhibition of proliferation was measured with colorimetric MTT assay. The morphologic changes were observed by fluorescence and electron microscopes. DNA fragmentation was visualized by agarose gel electrophoresis, and the DNA degradation was determined by flow cytometry. Immunohistochemical analysis was used to identify the expression of bcl-2 and bax genes. RESULTS: The growth of human HL-60 cells was significantly inhibited by erianin 20-81.9 nmol/L during 72 h treatment (P < 0.01). The IC50 value was 38 nmol/L after a 24-h exposure to erianin, while that of vincristine, the positive control, was 101 nmol/L. The typical morphologic changes were observed and the nuclear DNA fragmentation exhibited "ladder" pattern. The cell cycle of HL-60 cells was arrested in G2/M phase, and expression of bcl-2 gene was decreased while that of bax was increased. CONCLUSION: Erianin showed potent inhibitory activity on the proliferation of HL-60 cells. The inhibition might be relative to the apoptosis induced by erianin and the altered expression of bcl-2 and bax genes in HL-60 cells. (+info)The biology of the combretastatins as tumour vascular targeting agents. (2/44)
The tumour vasculature is an attractive target for therapy. Combretastatin A-4 (CA-4) and A-1 (CA-1) are tubulin binding agents, structurally related to colchicine, which induce vascular-mediated tumour necrosis in animal models. CA-1 and CA-4 were isolated from the African bush willow, Combretum caffrum, and several synthetic analogues are also now available, such as the Aventis Pharma compound, AVE8062. More soluble, phosphated, forms of CA-4 (CA-4-P) and CA-1 (CA-1-P) are commonly used for in vitro and in vivo studies. These are cleaved to the natural forms by endogenous phosphatases and are taken up into cells. The lead compound, CA-4-P, is currently in clinical trial as a tumour vascular targeting agent. In animal models, CA-4-P causes a prolonged and extensive shut-down of blood flow in established tumour blood vessels, with much less effect in normal tissues. This paper reviews the current understanding of the mechanism of action of the combretastatins and their therapeutic potential. (+info)New bibenzyl cannabinoid from the New Zealand liverwort Radula marginata. (3/44)
The ether extract of the New Zealand liverwort Radula marginata afforded a new cannabinoid type bibenzyl compound named perrottetinenic acid, and two new bibenzyls, together with a known cannabinoid, perrottetinene. Their structures were established by two dimensional (2D) NMR spectral data. The structure of perrottetinenic acid was a similar to that of Delta(1)-tetrahydrocannabinol, a known hallucinogen. Cannabinoid type bibenzyls have been isolated from liverwort Radula perrottetii, though have not previously been reported from the liverwort R. marginata. (+info)Phase I clinical trial of weekly combretastatin A4 phosphate: clinical and pharmacokinetic results. (4/44)
PURPOSE: A phase I trial was performed with combretastatin A4 phosphate (CA4P), a novel tubulin-binding agent that has been shown to rapidly reduce blood flow in animal tumors. PATIENTS AND METHODS: The drug was delivered by a 10-minute weekly infusion for 3 weeks followed by a week gap, with intrapatient dose escalation. Dose escalation was accomplished by doubling until grade 2 toxicity was seen. The starting dose was 5 mg/m2. RESULTS: Thirty-four patients received 167 infusions. CA4P was rapidly converted to the active combretastatin A4 (CA4), which was further metabolized to the glucuronide. CA4 area under the curve (AUC) increased from 0.169 at 5 mg/m2 to 3.29 micromol * h/L at 114 mg/m2. The mean CA4 AUC in eight patients at 68 mg/m2 was 2.33 micromol * h/L compared with 5.8 micromol * h/L at 25 mg/kg (the lowest effective dose) in the mouse. The only toxicity that possibly was related to the drug dose up to 40 mg/m2 was tumor pain. Dose-limiting toxicity was reversible ataxia at 114 mg/m2, vasovagal syncope and motor neuropathy at 88 mg/m2, and fatal ischemia in previously irradiated bowel at 52 mg/m2. Other drug-related grade 2 or higher toxicities seen in more than one patient were pain, lymphopenia, fatigue, anemia, diarrhea, hypertension, hypotension, vomiting, visual disturbance, and dyspnea. One patient at 68 mg/m2 had improvement in liver metastases of adrenocortical carcinoma. CONCLUSION: CA4P was well tolerated in 14 of 16 patients at 52 or 68 mg/m2; these are doses at which tumor blood flow reduction has been recorded. (+info)Comparative preclinical pharmacokinetic and metabolic studies of the combretastatin prodrugs combretastatin A4 phosphate and A1 phosphate. (5/44)
PURPOSE: Combretastatin A4 phosphate (CA4P) and its structural analog, combretastatin A1 phosphate (CA1P), are soluble prodrugs capable of interacting with tubulin and causing rapid vascular shutdown within tumors. CA4P has completed Phase I clinical trials, but recent preclinical studies have shown that CA1P displays a greater antitumor effect than the combretastatin A4 (CA4) analog at equal doses. The aim of this study, therefore, is to compare pharmacokinetics and metabolism of the two compounds to determine whether pharmacokinetics plays a role in their differential activity. EXPERIMENTAL DESIGN: NMRI mice bearing MAC29 tumors received injection with either CA4P or CA1P at a therapeutic dose of 150 mg x kg(-1), and profiles of both compounds and their metabolites analyzed by a sensitive and specific liquid chromatography/mass spectroscopy method. RESULTS: The metabolic profile of both compounds is complex, with up to 14 metabolites being detected for combretastatin A1 (CA1) in the plasma. Many of these metabolites have been identified by liquid chromatography/mass spectroscopy. Initial studies, however, focused on the active components CA4 and CA1, where plasma and tumor areas under the curve were 18.4 and 60.1 microg x h x ml(-1) for CA4, and 10.4 and 13.1 microg x h x ml(-1) for CA1, respectively. In vitro metabolic comparisons of the two compounds strongly suggest that CA1 is metabolized to a more reactive species than the CA4. CONCLUSIONS: Although in vitro studies suggest that variable rates of tumor-specific prodrug dephosphorylation may explain these differences in pharmacokinetics profiles, the improved antitumor activity and altered pharmacokinetic profile of CA1 may be due to the formation of a more reactive metabolite. (+info)Erianin induces a JNK/SAPK-dependent metabolic inhibition in human umbilical vein endothelial cells. (6/44)
BACKGROUND: Erianin is a natural product derived from Dendrobium chrysotoxum, with promising antitumor activity. MATERIALS AND METHODS: To evaluate the metabolic effect of erianin, a cytosensor assay for acidification rate, MTT assay, measurement of lactate, glucose and ATP were performed in human umbilical vein endothelial cells (HUVECs) exposed to 1-100 nM erianin. JNK/SAPK activity was detected by Western blot. RESULTS: Twelve- or 24- hour incubation with erianin induced a dose-dependent metabolic inhibition, as indicated by reduced acidification rate and cell viability, with an endothelium-selectivity. Erianin caused decreases in lactate production, glucose consumption and intracellular ATP level. Pretreatment with the JNK/SAPK inhibitor SP600125 significantly abolished these inhibitory responses, and especially restored the erianin-induced decreases in ATP and the erianin-induced phosphorylation of JNK/SAPK with dose- and time- dependence. CONCLUSION: Erianin inhibited endothelial metabolism in a JNK/SAPK-dependent manner. This mechanism may be involved in the potential antitumnor and antiangiogenic actions of erianin. (+info)A dual-color fluorescence imaging-based system for the dissection of antiangiogenic and chemotherapeutic activity of molecules. (7/44)
We have developed a simple yet sensitive dual color fluorescence-based technique for dissecting the tumor-neovascularization relationship and evaluated the susceptibility of each component to therapeutic interventions. Green fluorescent protein (GFP)-expressing melanoma cells were cocultured with endothelial cells on different three-dimensional (3-D) matrices and exposed to multiple growth factors and molecules with established anti-angiogenic or anticancer activities. Cells were fixed and stained with propidium iodide, imaged using a confocal microscope, and stereologically analyzed. Three-dimensionality of the system was tested by depth-coding and pseudocolor 3-D reconstruction in the z-axis. Selective ablation of the tumor cells was affected by the anthracycline antibiotic doxorubicin. Treatment with vascular endothelial growth factor (VEGF) and hepatocyte growth factor (HGF) promoted the neovascular responses on matrigel and collagen-1 matrices. VEGF-induced angiogenesis was inhibited after treatment with combretastatin and thalidomide. In contrast, HGF exerted a protective effect against these anti-angiogenics in a matrigel matrix. However, this effect was lost when the matrix was substituted with collagen, suggesting that the extracellular matrix impinges on cellular function, possibly through an Akt-mediated mechanism. The VEGF-receptor antagonist PTK787 also selectively ablated the VEGF-induced angiogenic effect without inhibiting the HGF-induced response, demonstrating the sensitivity of the system to detect modulation of distinct signal cascades. The current model encompasses the possibility of studying tumor-angiogenesis-matrix interaction on the same platform, expanding the rapid screening of novel molecules in a simulated clinicopathological setting. (+info)Temporal targeting of tumour cells and neovasculature with a nanoscale delivery system. (8/44)
In the continuing search for effective treatments for cancer, the emerging model is the combination of traditional chemotherapy with anti-angiogenesis agents that inhibit blood vessel growth. However, the implementation of this strategy has faced two major obstacles. First, the long-term shutdown of tumour blood vessels by the anti-angiogenesis agent can prevent the tumour from receiving a therapeutic concentration of the chemotherapy agent. Second, inhibiting blood supply drives the intra-tumoural accumulation of hypoxia-inducible factor-1alpha (HIF1-alpha); overexpression of HIF1-alpha is correlated with increased tumour invasiveness and resistance to chemotherapy. Here we report the disease-driven engineering of a drug delivery system, a 'nanocell', which overcomes these barriers unique to solid tumours. The nanocell comprises a nuclear nanoparticle within an extranuclear pegylated-lipid envelope, and is preferentially taken up by the tumour. The nanocell enables a temporal release of two drugs: the outer envelope first releases an anti-angiogenesis agent, causing a vascular shutdown; the inner nanoparticle, which is trapped inside the tumour, then releases a chemotherapy agent. This focal release within a tumour results in improved therapeutic index with reduced toxicity. The technology can be extended to additional agents, so as to target multiple signalling pathways or distinct tumour compartments, enabling the model of an 'integrative' approach in cancer therapy. (+info)
COMBRETASTATIN ANALOGS FOR USE IN THE TREATMENT OF CANCER - Patent application
Combretastatin was first isolated from the bark of the African bush willow tree, which grows in the Eastern Cape region of...
Combretastatin - Wikipedia
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Dendrobium nobile Lindley and its bibenzyl component moscatilin are able to protect retinal cells from ischemia/hypoxia by...
Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4:...
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p38 MAPK, but not ERK1/2, is critically involved in the cytotoxicity of the novel vascular disrupting agent combretastatin A4 -...
Combretastatin A-4 Phosphate Affects Tumor Vessel Volume and Size Distribution as Assessed Using MRI-Based Vessel Size Imaging ...
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Bibenzyl
ISBN 0-412-55070-9. Keserű, G. M.; Nógrádi, M. (1995). "The chemistry of macrocyclic bis(bibenzyls)". Natural Product Reports. ...
Dihydrostilbenoid
Bis(bibenzyls) and macrocyclic bis(benzyls) can be found in bryophytes, such as the compounds plagiochin E, 13,13'-O- ... Prenylated bibenzyls can be isolated from the New Zealand liverwort Marsupidium epiphytum or from Radula kojana. One unique ... doi:10.1016/S0031-9422(96)00387-1. Guo, H; Xing, J; Xie, C; Qu, J; Gao, Y; Lou, H (2007). "Study of bis(bibenzyls) in ... Bibenzyls (3,4'-dihydroxy-5,5'-dimethoxybibenzyl, 3,3'-dihydroxy-5-methoxybibenzyl (batatasin III)) can be found in the orchid ...
Perrottetinene
Cullmann F, Becker H (1999-04-01). "Prenylated Bibenzyls from the Liverwort Radula laxiramea". Zeitschrift für Naturforschung C ...
Marsupidium epiphytum
Prenylated bibenzyls can be isolated from M. epiphytum. Marsupidium epiphytum on Te Papa New Zealand's national museum website ... Toyota, Masao; Omatsu, Ikuko; Braggins, John; Asakawa, Yoshinori (2011). "Novel Prenyl Bibenzyls from the New Zealand Liverwort ...
Phenanthrenoid
... dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum". Phytochemistry. 44 (1): 157-165. doi:10.1016/s0031- ...
Bulbophyllum vaginatum
Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum. Leong Y-W, KAng C-C, Harrison LJ and ...
Argyrochosma nivea
Isonotholaenic acid, a dihydrostilbenoid, and other bibenzyls can be found in A. nivea. This compound shows an anti-chagasic ...
Dehalogenation
Toluene and bi-benzyls were produced as the product of the reaction. Morrison and his co-workers also reported dehalogenation ...
List of MeSH codes (D02)
... bibenzyls MeSH D02.455.426.559.389.140.400 - 2-hydroxy-5-nitrobenzyl bromide MeSH D02.455.426.559.389.140.450 - lignans MeSH ... bibenzyls MeSH D02.455.426.559.389.150.700.100 - chlorotrianisene MeSH D02.455.426.559.389.150.700.125 - clomiphene MeSH ...
Bauhinia purpurea
... bibenzyls, dibenzoxepins, mixture of phytol fatty esters, lutein, β-sitosterol, isoquercitin and astragalin.[citation needed] ...
Plagiochasma intermedium
... on www.uniprot.org Antifungal macrocyclic bis(bibenzyls) from the Chinese liverwort Ptagiochasm ...
Riccardin C
... bibenzyls) from the Chinese liverwort Ptagiochasm intermedlum L. Chun-Feng Xie, Jian-Bo Qu, Xiu-Zhen Wu, Na Liu, Mei Ji and ...
Marchantia polymorpha
... produces the antifungal bis[bibenzyls] dihydrostilbenoids plagiochin E, 13,13'-O-isoproylidenericcardin D ...
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HeteroCycles
Distribution of Cyclic and Acyclic Bis-bibenzyls in the Marchantiophyta (Liverworts), Ferns and Higher Plants and Their ... At present more than 70 of bis-bibenzyls have been found in liverworts. The structurally unique cyclic and acyclic bis- ... The Marchantiophyta (liverworts) are rich sources of cyclic and acyclic bis-bibenzyls which are very rare natural products in ... The present paper deals with the distribution of bis-bibenzyls in liverworts, fern and higher plants and their biological ...
DeCS
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HIGHLIGHTS: HPLC-ESI-MS/MS method for the analysis of bibenzyls and bis (bibenzyls) in Dendrobium officinale. Easy-to-use ... A total of nine isolated bibenzyls and their glycosides, 22 bis (bibenzyls), and two phenylpropanol bibenzyl derivatives were ... Identification of bibenzyls and evaluation of imitative wild planting techniques in Dendrobium officinale by HPLC-ESI-MSn. ... In addition, the relative content of bibenzyls increased with the growth of the original plant. This study provided a ...
Research Breakdown on Dendrobium - Examine
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Benzyl Compounds | Profiles RNS
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Studies on Antioxidant Activity of Bibenzyls and Phenolic Components from Dendrobium nobile--《Chinese Pharmaceutical Journal...
16 showed weak activity.CONCLUSION Most of the bibenzyls and phenolic components exhibited antioxidant activity in different ... was evaluated by DPPH free radical scavenging assay and oxygen radical absorbance capacity assay.RESULTS Three new bibenzyls ... OBJECTIVE To study the antioxidant activity of bibenzyls and phenolic components isolated from the 60% EtOH extract of ... OBJECTIVE To study the antioxidant activity of bibenzyls and phenolic components isolated from the 60% EtOH extract of ...
Journal of Pre-Clinical and Clinical Research - Keyword bis-bibenzyls
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MeSH Browser
Bibenzyls Preferred Term Term UI T004730. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1968). ... Bibenzyls Preferred Concept UI. M0002454. Registry Number. 0. Scope Note. Compounds that include 1,2-diphenylethane in their ... Bibenzyls. Tree Number(s). D02.455.426.559.389.140.308. Unique ID. D001632. RDF Unique Identifier. http://id.nlm.nih.gov/mesh/ ...
MeSH Browser
Bibenzyls Preferred Term Term UI T004730. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1968). ... Bibenzyls Preferred Concept UI. M0002454. Registry Number. 0. Scope Note. Compounds that include 1,2-diphenylethane in their ... Bibenzyls. Tree Number(s). D02.455.426.559.389.140.308. Unique ID. D001632. RDF Unique Identifier. http://id.nlm.nih.gov/mesh/ ...
Chrysotoxine, a novel bibenzyl compound selectively antagonizes MPP<sup>+</sup>, but not rotenone, neurotoxicity in...
c33c
Rare and precious chinese materia medica: Pseudobulbus cremastrae seu pleiones Norimoto H, Murayama C, Zhao F, Wei HY - Chin...
Li Y, Zhang F, Wu ZH, Zeng KW, Zhang C, Jin HW, et al. Nitrogen-containing bibenzyls from Pleione bulbocodioides: Absolute ... Li et al.[50],[51] isolated five novel compounds, including four pyrrolidone-substituted bibenzyls and a prenylated flavone, ... Li B, Noriko M, Masea Y, Shuzo T. A polyphenol and two bibenzyls from Pleione bulbocodioides. Cheminform 1998;47:1637-40. ... Wang Y, Guan SH, Meng YH, Zhang YB, Cheng CR, Shi YY, et al. Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their ...
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NDF-RT Code NDF-RT Name
Cuparene
Search | Global Index Medicus
Angiogenesis Inhibitors , Pharmacology , Animals , Benzyl Compounds , Pharmacology , Bibenzyls , Pharmacology , Cell Count , ... In the present study, we investigated the inhibitory effects of six bibenzyls isolated from Dendrobium species on vascular ... All those bibenzyls inhibited VEGF-induced tube formation at 10 micromol x L(-1) except tristin, and of which moscatilin was ...
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Diethylstilbestrol | Profiles RNS
Titus L, Hatch EE, Drake KM, Parker SE, Hyer M, Palmer JR, Strohsnitter WC, Adam E, Herbst AL, Huo D, Hoover RN, Troisi R. Reproductive and hormone-related outcomes in women whose mothers were exposed in utero to diethylstilbestrol (DES): A report from the US National Cancer Institute DES Third Generation Study. Reprod Toxicol. 2019 03; 84:32-38 ...