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Inhibition of cell proliferation and induction of apoptosis by oleanane triterpenoid CDDO-Me in pancreatic cancer cells is associated with the suppression of hTERT gene expression and its telomerase activity. The mechanisms of the antisurvival and apoptosis-inducing activities of CDDO-Me and related derivatives of oleanolic acid have been defined; however, to date, no study has been carried out on the effect of CDDOs on human telomerase reverse transcriptase hTERT gene or telomerase activity.
In the present study, we examined the efficacy of CDDO-Me in preventing the development and progression of prostate cancer in the transgenic adenocarinoma of the mouse prostate TRAMP model. Even delayed administration of CDDO-Me started at 12 wk of age for 12 wk inhibited the development of adenocarcimona of the prostate.
Directory of Open Access Journals Sweden. Full Text Available Pancreatic ductal adenocarcinoma PDA is one of the most lethal human malignancy with dismal prognosis and few effective therapeutic options. Novel agents that are safe and effective are urgently needed.
Oleanolic acid-derived synthetic triterpenoids are potent antitumorigenic agents, but their efficacy or the mechanism of action for pancreatic cancer has not been adequately investigated. In this study, we evaluated the antitumor activity and the mechanism of action of methylcyano-3,dioxooleana-1,9 dienoate CDDO-Me , a oleanane -derived synthetic triterpenoid for human pancreatic cancer cell lines.
Pancreatic ductal adenocarcinoma PDA is one of the most lethal human malignancy with dismal prognosis and few effective therapeutic options. In this study, we evaluated the antitumor activity and the mechanism of action of methylcyano-3,dioxooleana-1,9 11 -dienoate CDDO-Me , a oleanane -derived synthetic triterpenoid for human pancreatic cancer cell lines. Oleanane -type triterpenoid saponins from Lysimachia fortunei Maxim. Six previously undescribed oleanane -type triterpenoid saponins, fortunosides A-F, together with six known ones, were isolated from the aerial parts of Lysimachia fortunei Maxim.
Three saponins with the aglycone protoprimulagenin A exhibited moderate cytotoxicity against all of the tested human cancer cell lines, with IC 50 values ranging from 4.
All rights reserved. CDDO-Me protects normal lung and breast epithelial cells but not cancer cells from radiation. Full Text Available Although radiation therapy is commonly used for treatment for many human diseases including cancer, ionizing radiation produces reactive oxygen species that can damage both cancer and healthy cells.
Synthetic triterpenoids , including CDDO-Me , act as anti-inflammatory and antioxidant modulators primarily by inducing the transcription factor Nrf2 to activate downstream genes containing antioxidant response elements AREs. In the present series of experiments, we determined if CDDO-Me can be used as a radioprotector in normal non-cancerous human lung and breast epithelial cells, in comparison to lung and breast cancer cell lines. A panel of normal non-cancerous, partially cancer progressed, and cancer cell lines from both lung and breast tissue was exposed to gamma radiation with and without pre-treatment with CDDO-Me.
CDDO-Me did not protect cancer lines tested from radiation-induced cytotoxicity, nor did it protect experimentally transformed human bronchial epithelial cells HBECs with progressive oncogenic manipulations.
A therapeutic window exists in which CDDO-Me protects normal cells from radiation by activating the Nrf2 pathway, but does not protect experimentally transformed or cancer cell lines. This suggests that use of this oral available, non-toxic class of drug can protect non-cancerous healthy cells during radiotherapy, resulting in better outcomes and less toxicity for patients.
Cytotoxic oleanane -type triterpenoid saponins from the Rhizomes of Anemone rivularis var. Phytochemical investigation of the n-BuOH extract of the rhizomes of Anemone rivularis var. The cytotoxicity of these compounds was evaluated against four human cancer cell line, including HL promyelocytic leukemia , HepG2 hepatocellular carcinoma , A lung carcinoma and HeLa cervical carcinoma.
The monodesmosidic saponins exhibited cytotoxic activity toward all tested cancer cell lines, with IC50 values in the 7. Synthetic oleanane triterpenoids : multifunctional drugs with a broad range of applications for prevention and treatment of chronic disease.
We review the rationale for the use of synthetic oleanane triterpenoids SOs for prevention and treatment of disease, as well as extensive biological data on this topic resulting from both cell culture and in vivo studies.
Emphasis is placed on understanding mechanisms of action. SOs are noncytotoxic drugs with an excellent safety profile. Several hundred SOs have now been synthesized and in vitro have been shown to: 1 suppress inflammation and oxidative stress and therefore be cytoprotective, especially at low nanomolar doses, 2 induce differentiation, and 3 block cell proliferation and induce apoptosis at higher micromolar doses. In these interactions, Michael addition of SOs to reactive cysteine residues in specific molecular targets triggers biological activity.
Ultimately, SOs are multifunctional drugs that regulate the activity of entire networks. Recent progress in the earliest clinical trials with 2-cyano-3,dioxooleana-1,9 11 -dienoic acid CDDO methyl ester bardoxolone methyl is also.
Synthetic triterpenoid induces PGDH expression and suppresses inflammation-driven colon carcinogenesis. Colitis-associated colon cancer CAC develops as a result of inflammation-induced epithelial transformation, which occurs in response to inflammatory cytokine-dependent downregulation of hydroxyprostaglandin dehydrogenase PGDH and subsequent suppression of prostaglandin metabolism.
Synthetic triterpenoids are a class of small molecules that suppress COX-2 as well as inflammatory cytokine signaling. Similarly, CDDO-Me suppressed azoxymethane plus dextran sodium sulfate-induced carcinogenesis in wild-type animals, highlighting the potential of small molecules of the triterpenoid family as effective agents for the chemoprevention of CAC in humans. Polyoxygenated ursane and oleanane triterpenes from Siphonodon celastrineus. Twenty polyoxygenated triterpenes, including nineteen ursanes and one oleanane , were characterized from the stem material of Siphonodon celastrineus Celastraceae through the application of spectroscopic techniques and chemical transformation.
Three of the ursane-type triterpenoids possessed the rare 13,cyclopropane ring skeleton. Reaction of lupane and oleanane triterpenoids with Lawesson's reagent. Lupane, friedelane, oleanane , and ursane triterpenes from the stem of Siphonodon celastrineus Griff. Twenty-one triterpenes consisting of a lupane derivative, two friedelanes, an oleanane derivative, and 17 ursane-type triterpenoids , together with three known triterpenes, three sterols, a fatty acid, a sesquiterpene alkaloid, and a glycerol derivative, were isolated from the stem of Siphonodon celastrineus.
Their structures were characterized by various spectroscopic techniques, as well as comparison with literature data. Twenty-seven metabolites of these were evaluated for cytotoxic activity against six human cancer cell lines. The biosynthetic formation of a 1,4-dioxane bridge is also discussed. Nonsterol Triterpenoids as Major Constituents of Olea europaea.
Plant triterpenoids represent a large and structurally diverse class of natural products. A growing interest has been focused on triterpenoids over the past decade due to their beneficial effects on human health. We show here that these bioactive compounds are major constituents of several aerial parts floral bud, leaf bud, stem, and leaf of olive tree, a crop exploited so far almost exclusively for its fruit and oil.
Twenty sterols and twenty-nine nonsteroidal tetra- and pentacyclic triterpenoids belonging to seven types of carbon skeletons oleanane , ursane, lupane, taraxerane, taraxastane, euphane, and lanostane were identified and quantified by GC and GC-MS as free and esterified compounds.
The oleanane -type compounds, oleanolic acid and maslinic acid, were largely predominant in all the organs tested, whereas they are practically absent in olive oil.
In floral buds, they represented as much as 2. In callus cultures, lanostane-type compounds were the most abundant triterpenoids.
In all the tissues analyzed, free and esterified triterpene alcohols exhibited different distribution patterns of their carbon skeletons. Taken together, these data provide new insights into largely unknown triterpene secondary metabolism of Olea europaea.
Immunosuppressive potential of bardoxolone methyl using a modified murine local lymph node assay LLNA. We assessed its immunosuppressive potential by using the modified mouse lymph node assay LLNA including immunosuppression-related gene expression analysis.
It has been already reported that a decrease in lymph node weight was induced by several types of immunosuppressive chemicals such as calcineurin inhibitors, antimetabolites, steroids, and alkylators. In addition, changes in Zfp and Fmo2 expression was reported in response after only treatment of antimetabolites. From these results, CDDO-Me is considered to have an immunosuppressive action and similar mechanism to antimetabolites.
Cuspidate A, new anti-fungal triterpenoid saponin from Lepidagathis cuspidata. One new triterpenoid saponin named cuspidate A 1 along with a known oleanane -based triterpenoid saponin clemontanoside-C were isolated from the roots of Lepidagathis cuspidata. The structure of new compound 1 was established after detailed analysis of spectroscopic data including 1D and 2D NMR spectra.
This is the first report on clemontanoside-C from this genus. These saponins were found to be effective against the selected fungal strains Aspergillus flavus, Rhizopus stolinifer, Penicillum nodatum, Aspergillus fumigates. Compound 1 showed better activity, comparable to the synthetic drug, while compound 2 showed a moderate effect against all studied fungal strains. Quantitative determination for cytotoxic Friedo-nor- oleanane derivatives from five morphological types of Maytenus ilicifolia Celastraceae by reverse-phase high-performance liquid chromatography.
Five different morphological types of Maytenus ilicifolia of the same age and harvested under the same conditions showed distinct accumulations of some friedo-nor- oleananes. A rapid, sensitive and reliable reverse-phase HPLC method employing an external standard was used for the determination of the cytotoxic triterpenoids , 20 alpha-hydroxymaytenin, 22 beta-hydroxymaytenin, maytenin, celastrol and pristimerin in each of the five types.
Well resolved peaks with good detection response and linearity in the range 1. Triterpenoids from Arctium lappa. Antimicrobial steroidal saponin and oleanane -type triterpenoid saponins from Paullinia pinnata. Paullinia pinnata L. Sapindaceae is an African woody vine, which is widely used in traditional medicine for the treatment of human malaria, erectile dysfunction and bacterial infections. A phytochemical investigation of its methanol leaf and stem extracts led to the isolation of seven compounds which were evaluated for their antimicrobial properties.
The extracts were fractionated and compounds were isolated by chromatographic methods. Their structures were elucidated from their spectroscopic data in conjunction with those reported in literature. The antimicrobial activities of the crude extracts, fractions and compounds were evaluated against bacteria, yeasts and dermatophytes using the broth micro-dilution technique.
Compounds 5 and 7 showed the best antibacterial and anti-yeast activities respectively MIC value range of 0. The results of the present findings could be considered interesting, taking into account the global disease burden of these susceptible microorganisms, in conjunction with the search for alternative and complementary medicines. Cytotoxic triterpenoid saponins from Clematis tangutica.
Eight previously undescribed oleanane -type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica Maxim. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods acid hydrolysis and mild alkaline hydrolysis. Clematangoticosides D-G were found to be unusual 23, bidesmosidic glycosides. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.
For centuries oak wood Quercus robur has been used in aging of wines and spirits, which is based on pleasant flavors given to beverages by phenolics transferred to the liquid during the maturation process. Other metabolites, such as triterpenoids , can also be released. Searching for extractable triterpenoids in oak heartwood, 12 new, , and five known, , oleanane types were isolated and characterized.
A galloyl unit attached to the triterpenoid moiety was established as the key feature for such effect. These results highlight the occurrence of triterpenoids in oak heartwood and their relevance for chemoprevention of breast cancer. Candidate genes involved in the biosynthesis of triterpenoid saponins in Platycodon grandiflorum identified by transcriptome analysis. Full Text Available Background: Platycodon grandiflorum is the only species in the genus Platycodon of the family Campanulaceae, which has been traditionally used as a medicinal plant for its lung-heat-clearing, antitussive, and expectorant properties in China, Japanese and Korean.
Oleanane -type triterpenoid saponins were the main chemical components of P. Hence, P. In addition, the genomic information of this important herbal plant is unavailable. Principal Findings:A total of 58,, clean reads were obtained, which were assembled into 34, unigenes, with an average length of bp and N50 of 1, bp by analyzing the transcriptome data of P.
This ritual is held routinely every year at mid-period between the postharvest of agricultural crops and field preparations for the next planting period. In this ritual, the trees used are in local language called "pare", "jita", "nio", "peri", and "laka", and the livestocks are "manu" and "rongo". However, before the ritual was performed other trees were used in the framework to prepare later ritual, i. The roles of trees and livestocks in the "Djoka Dju" ritual were discussed.