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Bruceantin

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https://www.readbyqxmd.com/read/27686478/quassinoids-isolated-from-brucea-javanica-inhibit-pepper-mottle-virus-in-pepper
#1
Seung Mok Ryu, Jaeyoung Kwon, Young Hye Seo, Eun Gyeong Song, Seong Su Hong, Beom Seok Kim, Jin Sung Hong, Ki Hyun Ryu, Dongho Lee
A green fluorescent protein (GFP)-tagged pepper mottle virus (PepMoV) based leaf-disc method and systemic host method were developed to identify antiviral agents. Preliminary experiments using a PepMoV-GFP based leaf-disc method led to the isolation of five quassinoids, including brusatol (1), bruceantin (2), brucein A (3), bruceantinol (4), and brucein B (5), from the CH3 OH extract of Brucea javanica. All isolated compounds exhibited inactivation effects in systemic host plants, and compounds 3 and 4 were potent, with a minimum inhibitory concentration of 10μM...
January 2, 2017: Virus Research
https://www.readbyqxmd.com/read/27434731/bruceantin-inhibits-multiple-myeloma-cancer-stem-cell-proliferation
#2
Mark E Issa, Sarah Berndt, Gilles Carpentier, John M Pezzuto, Muriel Cuendet
Multiple myeloma (MM) continues to claim the lives of a majority of patients. MM cancer stem cells (CSCs) have been demonstrated to sustain tumor growth. Due to their ability to self-renew and to express detoxifying enzymes and efflux transporters, MM-CSCs are rendered highly resistant to conventional therapies. Therefore, managing MM-CSCs characteristics could have profound clinical implications. Bruceantin (BCT) is a natural product previously demonstrated to inhibit the growth of MM in RPMI 8226 cells-inoculated mouse xenograft models, and to cause regression in already established tumors...
September 2016: Cancer Biology & Therapy
https://www.readbyqxmd.com/read/25057897/anionic-polycyclization-entry-to-tricycles-related-to-quassinoids-and-terpenoids-a-stereocontrolled-total-synthesis-of-cassaine
#3
Kontham Ravindar, Pierre-Yves Caron, Pierre Deslongchamps
A full account of our anionic polycyclization approach to access highly functionalized tricycles related to quassinoids and terpenoids from several optically active bicyclic enone systems and Nazarov reagents is presented. (+)-Carvone is the only chiral source used to fix the entire stereochemistry of all of the tricycles, and the stereochemical outcome of this process was unambiguously determined by X-ray crystallographic analysis. The utility of this strategy was demonstrated by the stereocontrolled construction of advanced tricycles related to the highly potent anticancer natural product bruceantin, a member of quassinoid family, and the total synthesis of the cardioactive terpenoid (+)-cassaine, a nonsteroidal inhibitor of Na(+)-K(+)-ATPase...
September 5, 2014: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/24318349/antifeedant-activity-of-quassinoids
#4
V Leskinen, J Polonsky, S Bhatnagar
The antifeedant activity of 13 quassinoids of different structural types has been studied against the Mexican bean beetle (Epilachna varivestis Mulsant) 4th instar larvae and the southern armyworm (Spodoptera eridania Crawer) 5th instar larvae. All quassinoids tested displayed significant activity against the Mexican bean beetle and, thus, do not reveal a simple structure-activity relationship. Five quassinoids were active against the southern armyworm. Interestingly, four of these-bruceantin (I), glaucarubinone (VI), isobruceine A (VIII), and simalikalactone D (XI)-possess the required structural features for antineoplastic activity...
October 1984: Journal of Chemical Ecology
https://www.readbyqxmd.com/read/21143123/quassinoids-from-traditional-drugs-to-new-cancer-therapeutics
#5
REVIEW
G Fiaschetti, M A Grotzer, T Shalaby, D Castelletti, A Arcaro
Quassinoids are a group of compounds extracted from plants of the Simaroubaceae family, which have been used for many years in folk medicine. These molecules gained notoriety after the initial discovery of the anti-leukemic activity of one member, bruceantin, in 1975. Currently over 150 quassinoids have been isolated and classified based on their chemical structures and biological properties investigated in vitro and in vivo. Many molecules display a wide range of inhibitory effects, including anti-inflammatory, anti-viral, anti-malarial and anti-proliferative effects on various tumor cell types...
2011: Current Medicinal Chemistry
https://www.readbyqxmd.com/read/20944100/nf-kappab-inhibitors-from-brucea-javanica-exhibiting-intracellular-effects-on-reactive-oxygen-species
#6
Jeong-Ah Kim, Edward K Lau, Li Pan, Esperanza J Carcache De Blanco
AIM: Brucea javanica was studied to identify nuclear factor kappaB (NF-κB) inhibitors exhibiting reactive oxygen species (ROS) intracellular amplification. MATERIAL AND METHODS: Eight compounds were evaluated for selective cytotoxicity using HT-29, HeLa, and HL-60 cells, and in a NF-κB assay. Active compounds were then tested using ROS and mitochondria transmembrane potential (MTP) assays. NF-κB and nuclear factor activated T-cell (NFAT) translocation were also assessed using their respective whole cell assays...
September 2010: Anticancer Research
https://www.readbyqxmd.com/read/19412536/altering-chemosensitivity-by-modulating-translation-elongation
#7
Francis Robert, Marilyn Carrier, Svea Rawe, Samuel Chen, Scott Lowe, Jerry Pelletier
BACKGROUND: The process of translation occurs at a nexus point downstream of a number of signal pathways and developmental processes. Modeling activation of the PTEN/AKT/mTOR pathway in the Emu-Myc mouse is a valuable tool to study tumor genotype/chemosensitivity relationships in vivo. In this model, blocking translation initiation with silvestrol, an inhibitor of the ribosome recruitment step has been showed to modulate the sensitivity of the tumors to the effect of standard chemotherapy...
2009: PloS One
https://www.readbyqxmd.com/read/19362093/u2504-determines-the-species-specificity-of-the-a-site-cleft-antibiotics-the-structures-of-tiamulin-homoharringtonine-and-bruceantin-bound-to-the-ribosome
#8
Güliz Gürel, Gregor Blaha, Peter B Moore, Thomas A Steitz
Structures have been obtained for the complexes that tiamulin, homoharringtonine, and bruceantin form with the large ribosomal subunit of Haloarcula marismortui at resolutions ranging from 2.65 to 3.2 A. They show that all these inhibitors block protein synthesis by competing with the amino acid side chains of incoming aminoacyl-tRNAs for binding in the A-site cleft in the peptidyl-transferase center, which is universally conserved. In addition, these structures support the hypothesis that the species specificity exhibited by the A-site cleft inhibitors is determined by the interactions they make, or fail to make, with a single nucleotide, U2504 (Escherichia coli)...
May 29, 2009: Journal of Molecular Biology
https://www.readbyqxmd.com/read/19026551/bioactivity-guided-isolation-of-cytotoxic-constituents-of-brucea-javanica-collected-in-vietnam
#9
Li Pan, Young-Won Chin, Hee-Byung Chai, Tran Ngoc Ninh, Djaja Djendoel Soejarto, A Douglas Kinghorn
Five new triterpenoids (1-5), together with two known quassinoids, bruceantin (6) and bruceine A (7), and a known flavonolignan, (-)-hydnocarpin (8), were isolated from the chloroform-soluble subfraction of a methanol extract of the combined twigs, leaves, and inflorescence of Brucea javanica collected in Vietnam. The structures of the new compounds 1-5 were established on the basis of spectroscopic methods. All isolates were evaluated for cytotoxicity against a small panel of human cancer cell lines. Quassinoids 6 and 7 were found to be highly active against these cell lines...
March 15, 2009: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/16789880/synthesis-of-a-b-ring-partial-analogs-of-bruceantin-as-potential-antimalarial-agents
#10
Z Guo, S Vangapandu, A Nimrod, L A Walker, R D Sindelar
Bruceantin (1), a classical quassinoid with the highest reported antimalarial activity among the quassinoids examined thus far, was selected as a natural product lead for the design of a series of A/B-ring analogs. A viable strategy for the synthesis of the series was developed. The functionalized A-ring and the C-15 ester moiety in bruceantin are incorporated in all designed compounds. The preliminary bioassay results will be discussed in detail.
January 2005: Medicinal Chemistry
https://www.readbyqxmd.com/read/15326546/natural-inhibitors-of-carcinogenesis
#11
REVIEW
A Douglas Kinghorn, Bao-Ning Su, Dae Sik Jang, Leng Chee Chang, Dongho Lee, Jian-Qiao Gu, Esperanza J Carcache-Blanco, Alison D Pawlus, Sang Kook Lee, Eun Jung Park, Muriel Cuendet, Joell J Gills, Krishna Bhat, Hye-Sung Park, Eugenia Mata-Greenwood, Lynda L Song, Meishiang Jang, John M Pezzuto
Previous collaborative work by our group has led to the discovery of several plant isolates and derivatives with activities in in vivo models of cancer chemoprevention, including deguelin, resveratrol, bruceantin, brassinin, 4'-bromoflavone, and oxomate. Using a panel of in vitro bioassays to monitor chromatographic fractionation, a diverse group of plant secondary metabolites has been identified as potential cancer chemopreventive agents from mainly edible plants. Nearly 50 new compounds have been isolated as bioactive principles in one or more in vitro bioassays in work performed over the last five years...
August 2004: Planta Medica
https://www.readbyqxmd.com/read/14987068/antitumor-activity-of-bruceantin-an-old-drug-with-new-promise
#12
REVIEW
Muriel Cuendet, John M Pezzuto
Bruceantin was first isolated from Brucea antidysenterica, a tree used in Ethiopia for the treatment of cancer, and activity was observed against B16 melanoma, colon 38, and L1210 and P388 leukemia in mice. Phase I and II clinical trials were then initiated, but no objective tumor regressions were observed and clinical development was terminated. Recently, the activity of bruceantin has been studied with a number of leukemia, lymphoma, and myeloma cell lines. Cell differentiation was induced and c-MYC was down-regulated, suggesting a mechanistic correlation between c-MYC down-regulation and induction of cell differentiation or cell death...
February 2004: Journal of Natural Products
https://www.readbyqxmd.com/read/14871997/multiple-myeloma-regression-mediated-by-bruceantin
#13
Muriel Cuendet, Konstantin Christov, Daniel D Lantvit, Yunfan Deng, Samad Hedayat, Lawrence Helson, James D McChesney, John M Pezzuto
PURPOSE: Bruceantin has been shown to induce cell differentiation in a number of leukemia and lymphoma cell lines. It also down-regulated c-MYC, suggesting a correlation of down-regulation with induction of cell differentiation or cell death. In the present study, we focused on multiple myeloma, using the RPMI 8226 cell line as a model. EXPERIMENTAL DESIGN: The effects of bruceantin on c-MYC levels and apoptosis were examined by immunoblotting, 4',6-diamidino-2-phenylindole staining, evaluation of caspase-like activity, and 3,3'-dihexyloxacarbocyanine iodide staining...
February 1, 2004: Clinical Cancer Research: An Official Journal of the American Association for Cancer Research
https://www.readbyqxmd.com/read/12399973/brusatol-mediated-induction-of-leukemic-cell-differentiation-and-g-1-arrest-is-associated-with-down-regulation-of-c-myc
#14
E Mata-Greenwood, M Cuendet, D Sher, D Gustin, W Stock, J M Pezzuto
Employing the natural product quassinoid brusatol, we currently report cellular and molecular events leading to cell death or terminal differentiation in a panel of leukemic cells. Brusatol and bruceantin exerted significant cytotoxic effects with several leukemic cell lines, but not with K562 or normal lymphocytic cells. Cell lines that were less sensitive to the cytotoxic effects of brusatol responded primarily through induction of terminal differentiation. The differentiated phenotype in cell lines derived from acute or chronic myeloid leukemias (HL-60, K562, Kasumi-1, NB4, U937, BV173) was characterized for producing superoxide and non-specific esterase, and some with up-regulation of CD13 (cluster of differentiation) and down-regulation of CD15...
November 2002: Leukemia: Official Journal of the Leukemia Society of America, Leukemia Research Fund, U.K
https://www.readbyqxmd.com/read/11754601/novel-esters-of-glaucarubolone-as-inducers-of-terminal-differentiation-of-promyelocytic-hl-60-cells-and-inhibitors-of-7-12-dimethylbenz-a-anthracene-induced-preneoplastic-lesion-formation-in-mouse-mammary-organ-culture
#15
E Mata-Greenwood, J F Daeuble, P A Grieco, J Dou, J D McChesney, R G Mehta, A D Kinghorn, J M Pezzuto
In an effort to discover new chemotherapeutic/chemopreventive agents from natural sources, brusatol (1) was found to induce HL-60 cellular differentiation, accompanied by strong antiproliferative and cytotoxic effects. A series of natural and semisynthetic quassinoids (1-48) was designed to effect both antiproliferative and differentiation-inducing properties. Compounds were assessed in vitro using the HL-60 promyelocytic cell model. Changes in activity due to structural modification of the core structure glaucarubolone (24) were consistent with activities reported in other cell systems...
December 2001: Journal of Natural Products
https://www.readbyqxmd.com/read/9313855/synthesis-of-cytotoxic-fluorinated-quassinoids
#16
N Ohno, N Fukamiya, M Okano, K Tagahara, K H Lee
The C-15 senecioyl side chain of brusatol was interchanged with fluorinated acyl groups, and the C-3 hydroxy group of bruceolide was esterified with fluorinated acyl chlorides. These fluorinated quassinoids 11, 12, 13, and 17 showed significant cytotoxic activity against eight human cancer cell lines including small and non-small cell lung, colon, CNS, ovarian and renal cancers, leukemia, and melanoma with 17 being about 100 times more potent than 11, 12, and 13. The activity of 17 was similar to that of bruceantin (1) in this in vitro cell line panel...
August 1997: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/7707371/fine-structure-of-the-peptidyl-transferase-centre-on-23-s-like-rrnas-deduced-from-chemical-probing-of-antibiotic-ribosome-complexes
#17
COMPARATIVE STUDY
C Rodriguez-Fonseca, R Amils, R A Garrett
Ribosomal binding sites were investigated for the diverse group of antibiotics: anisomycin, anthelmycin, blasticidin S, bruceantin, carbomycin, chloramphenicol, griseoviridin, narciclasine, T2 toxin, tylosin and virginiamycin M1 all of which are considered to inhibit the peptidyl transferase reaction by different mechanisms. The drugs also exhibit differing degrees of specificity for bacterial, archaeal and eukaryotic ribosomes despite a high level of conservation of sequence and secondary structure at the peptidyl transferase centre of the 23 S-like rRNAs...
March 24, 1995: Journal of Molecular Biology
https://www.readbyqxmd.com/read/7457834/radioimmunoassay-for-the-detection-and-quantitation-of-bruceantin
#18
K L Fong, D H Ho, C J Carter, N S Brown, R S Benjamin, E J Freireich, G P Bodey
No abstract text is available yet for this article.
July 1, 1980: Analytical Biochemistry
https://www.readbyqxmd.com/read/7399092/bruceantin-an-inhibitor-of-the-initiation-of-protein-synthesis-in-eukaryotes-proceedings
#19
Y M Beran, C R Benzie, J E Kay
No abstract text is available yet for this article.
June 1980: Biochemical Society Transactions
https://www.readbyqxmd.com/read/7299649/antitumor-agents-xlii-comparison-of-antileukemic-activity-of-helenalin-brusatol-and-bruceantin-and-their-esters-on-different-strains-of-p-388-lymphocytic-leukemic-cells
#20
COMPARATIVE STUDY
I H Hall, K H Lee, M Okano, D Sims, T Ibuka, Y F Liou, Y Imakura
Based on the fact that some known antineoplastic agents possess an ester moiety within their structure, the esters of helenalin, a sesquiterpene lactone, and of brusatol and bruceantin, quassinoids, were synthesized and tested for antileukemic activity in the P-388 screen. These agents gave different T/C% values dependent on the P-388 lymphocytic leukemia strain and the host strain of mice used. Later studies demonstrated that the agents caused different degrees of inhibition of nucleic acid and protein synthesis in the various P-388 strains...
October 1981: Journal of Pharmaceutical Sciences
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