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Triterpenoids

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https://www.readbyqxmd.com/read/28225183/protective-effects-of-araloside-c-against-myocardial-ischaemia-reperfusion-injury-potential-involvement-of-heat-shock-protein-90
#1
Min Wang, Yu Tian, Yu-Yang Du, Gui-Bo Sun, Xu-Dong Xu, Hai Jiang, Hui-Bo Xu, Xiang-Bao Meng, Jing-Yi Zhang, Shi-Lan Ding, Miao-di Zhang, Ming-Hua Yang, Xiao-Bo Sun
The present study was designed to investigate whether Araloside C, one of the major triterpenoid compounds isolated from Aralia elata known to be cardioprotective, can improve heart function following ischaemia/reperfusion (I/R) injury and elucidate its underlying mechanisms. We observed that Araloside C concentration-dependently improved cardiac function and depressed oxidative stress induced by I/R. Similar protection was confirmed in isolated cardiomyocytes characterized by maintaining Ca(2+) transients and cell shortening against I/R...
February 22, 2017: Journal of Cellular and Molecular Medicine
https://www.readbyqxmd.com/read/28218475/profound-changes-in-mirna-expression-during-cancer-initiation-by-aflatoxin-b1-and-their-abrogation-by-the-chemopreventive-triterpenoid-cddo-im
#2
Merricka C Livingstone, Natalie M Johnson, Bill D Roebuck, Thomas W Kensler, John D Groopman
Aflatoxin B1 (AFB1 ) is a potent human and animal hepatocarcinogen. To investigate the effects of aflatoxin on miRNA expression during the initiation phase of carcinogenesis, next-generation sequencing was used to analyze liver tissues from F344 rats exposed to 200 µg/kg per day AFB1 for 4 weeks. A panel of miRNAs was identified that was upregulated with AFB1 treatment compared to controls: rno-miR-434-3p, rno-miR-411-5p, rno-miR-221-3p, rno-miR-127-3p, rno-miR-205, rno-miR-429, rno-miR-34a-5p, rno-miR-181c-3p, rno-miR-200b-3p, and rno-miR-541-5p...
February 20, 2017: Molecular Carcinogenesis
https://www.readbyqxmd.com/read/28218000/chemical-constituents-and-anti-inflammatory-principles-from-the-fruits-of-forsythia-suspensa
#3
Ping-Chung Kuo, Hsin-Yi Hung, Chi-Wei Nian, Tsong-Long Hwang, Ju-Chien Cheng, Daih-Huang Kuo, E-Jian Lee, Shih-Huang Tai, Tian-Shung Wu
Fifty compounds were isolated from the fruits of Forsythia suspensa, including 13 new compounds characterized as eight new diterpenoids (1-8), three new lignans (9-11), a new iridoid (12), and a new triterpenoid (13). Their structures were established on the basis of spectroscopic and spectrometric analysis. Most of the isolated compounds were examined for their anti-inflammatory activity in vitro. The results showed that several compounds displayed significant inhibition of fMLP/CB-induced superoxide anion generation and elastase release, with IC50 values ranging from 0...
February 20, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28216107/an-endoplasmic-reticulum-engineered-yeast-platform-for-overproduction-of-triterpenoids
#4
Philipp Arendt, Karel Miettinen, Jacob Pollier, Riet De Rycke, Nico Callewaert, Alain Goossens
Saponins are a structurally diverse family of triterpenes that are widely found as main constituents in many traditional plant-based medicines and often have bioactivities of industrial interest. The heterologous production of triterpene saponins in microbes remains challenging and only limited successful pathway engineering endeavors have been reported. To improve the production capacities of a Saccharomyces cerevisiae saponin production platform, we assessed the effects of several hitherto unexplored gene knockout targets on the heterologous production of triterpenoids...
February 16, 2017: Metabolic Engineering
https://www.readbyqxmd.com/read/28215418/immunomodulatory-hemolytic-properties-and-cytotoxic-activity-potent-of-triterpenoid-saponins-from-cephalaria-balansae
#5
Hilal Top, Nazli Boke Sarikahya, Ayse Nalbantsoy, Suheyla Kirmizigul
Phytochemical investigations on n-butanol extract of Cephalaria balansae Raus. (Caprifoliaceae) led to the isolation of four previously undescribed triterpenoid saponins based on hederagenin type aglycone, namely, balansoides A-D, along with ten known compounds. Their structures were proposed based on 1D and 2D NMR spectroscopic data, HRESIMS analysis and chemical evidence as 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-galactopyranosyl-(1 → 6)-β-D-glucopyranosyl ester and 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester...
February 16, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28213589/sh479-a-betulinic-acid-derivative-ameliorates-experimental-autoimmune-encephalomyelitis-by-regulating-the-th17-treg-balance
#6
Jing Li, Ji Jing, Yang Bai, Zhen Li, Roumei Xing, Binhe Tan, Xueyun Ma, Wenwei Qiu, Changsheng Du, Bing Du, Fan Yang, Jie Tang, Stefan Siwko, Mingyao Liu, Huaqing Chen, Jian Luo
CD4+ T helper cells, especially Th17 cells, combined with immune regulatory network dysfunction, play key roles in autoimmune diseases including multiple sclerosis (MS). Betulinic acid (BA), a natural pentacyclic triterpenoid, has been reported to be involved in anti-inflammation, in particular having an inhibitory effect on pro-inflammatory cytokine IL-17 and IFN-γ production. In this study, we screened BA derivatives and found a BA derivative, SH479, which had a greater inhibitory effect on Th17 differentiation...
February 17, 2017: Molecular Pharmacology
https://www.readbyqxmd.com/read/28212341/physicochemical-characterization-and-biological-activities-of-the-triterpenic-mixture-%C3%AE-%C3%AE-amyrenone
#7
Rosilene G S Ferreira, Walter F Silva Júnior, Valdir F Veiga Junior, Ádley A N Lima, Emerson S Lima
α-Amyrenone and β-amyrenone are triterpenoid isomers that occur naturally in very low concentrations in several oleoresins from Brazilian Amazon species of Protium (Burseraceae). This mixture can also be synthesized by oxidation of α,β-amyrins, obtained as major compounds from the same oleoresins. Using a very simple, high yield procedure, and using a readily commercially available mixture of α,β-amyrins as substrate, the binary compound α,β-amyrenone was synthesized and submitted to physico-chemical characterization using different techniques such as high-performance liquid chromatography, nuclear magnetic resonance (¹H and (13)C), mass spectrometry, scanning electron microscopy, differential scanning calorimetry, thermogravimetry and derivative thermogravimetry, and Fourier transform infrared spectroscopy (FTIR)...
February 16, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28211011/teoa-a-triterpenoid-from-actinidia-eriantha-induces-autophagy-in-sw620-cells-via-endoplasmic-reticulum-stress-and-ros-dependent-mitophagy
#8
Dandan Zhang, Cuixia Gao, Ruyi Li, Lin Zhang, Jingkui Tian
2α,3α,24-Thrihydroxyurs-12-en-28-oicacid (TEOA), a pentacyclic triterpenoid, isolated from the roots of Actinidia eriantha, exhibits significant cytotoxicity against SW620, BGC-823, HepG-2, A549 and PC-3 cancer cells. In this study, we investigated the underlying molecular mechanism of the anticancer activity of TEOA in SW620 cells. We demonstrated that TEOA induced apoptosis through cleavage of caspase-9 and PARP in SW620 cells. In addition, evidence of TEOA-mediated autophagy included the induction of autophagolysosomes and activation of autophagic markers LC-3B and p62...
February 16, 2017: Archives of Pharmacal Research
https://www.readbyqxmd.com/read/28209994/reversal-of-the-apoptotic-resistance-of-non-small-cell-lung-carcinoma-towards-trail-by-natural-product-toosendanin
#9
Xin Li, Ming You, Yong-Jian Liu, Lin Ma, Pei-Pei Jin, Ri Zhou, Zhao-Xin Zhang, Baojin Hua, Xiao-Jun Ji, Xiao-Ying Cheng, Fangzhou Yin, Yan Chen, Wu Yin
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) selectively triggers cancer cell death via its association with death receptors on the cell membrane, but exerts negligible side effects on normal cells. However, some non-small-cell lung carcinoma (NSCLC) patients exhibited resistance to TRAIL treatment in clinical trials, and the mechanism varies. In this study, we described for the first time that toosendanin (TSN), a triterpenoid derivative used in Chinese medicine for pain management, could significantly sensitize human primary NSCLC cells or NSCLC cell lines to TRAIL-mediated apoptosis both in vitro and in vivo, while showing low toxicity against human primary cells or tissues...
February 17, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28208611/betulinic-acid-mediated-apoptosis-in-human-prostate-cancer-cells-involves-p53-and-nuclear-factor-kappa-b-nf-%C3%AE%C2%BAb-pathways
#10
Eswar Shankar, Ailin Zhang, Daniel Franco, Sanjay Gupta
Defects in p53 and nuclear factor-kappa B (NF-κB) signaling pathways are frequently observed in the initiation and development of various human malignancies, including prostate cancer. Clinical studies demonstrate higher expression of NF-κB/p65/RelA, NF-κB/p50/RelB, and cRel as well as downregulation of the p53 network in primary prostate cancer specimens and in metastatic tumors. Betulinic acid (BA), is a triterpenoid that has been reported to be an effective inducer of apoptosis through modification of several signaling pathways...
February 10, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28195390/self-assembly%C3%A2-of%C3%A2-renewable%C3%A2-nano-sized-triterpenoids
#11
REVIEW
Braja Gopal Bag, Rakhi Majumdar
Studies on plant metabolites have gained renewed interest in recent years because these can serve as renewable chemicals for the development of a sustainable society.Among various plant secondary metabolites, terpenoids constitute the major component and triterpenoids are the 30C subset of it.In recent years, triterpenoids have drawn the attention of scientific community due to many of its potential and realized applications in medicine, drug delivery, thermochromic materials, pollutant capture, catalysis, liquid crystals, etc...
February 14, 2017: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
https://www.readbyqxmd.com/read/28194155/functional-characterization-of-cyp716-family-p450-enzymes-in-triterpenoid-biosynthesis-in-tomato
#12
Shuhei Yasumoto, Hikaru Seki, Yuko Shimizu, Ery O Fukushima, Toshiya Muranaka
Triterpenoids are a group of structurally diverse specialized metabolites that frequently show useful bioactivities. These chemicals are biosynthesized from the common precursor 2,3-oxidosqualene in plants. The carbon skeletons produced by oxidosqualene cyclase (OSC) are usually modified by cytochrome P450 monooxygenases (P450s) and UDP-dependent glycosyltransferases. These biosynthetic enzymes contribute to the structural diversification of plant triterpenoids. Until now, many P450 enzymes have been characterized as triterpenoid oxidases...
2017: Frontiers in Plant Science
https://www.readbyqxmd.com/read/28190466/the-total-triterpenoid-saponins-of-xanthoceras-sorbifolia-improve-learning-and-memory-impairments-through-against-oxidative-stress-and-synaptic-damage
#13
Xue-Fei Ji, Tian-Yan Chi, Peng Liu, Lu-Yi Li, Ji-Kai Xu, Qian Xu, Li-Bo Zou, Da-Li Meng
BACKGROUND: X. sorbifolia is a widely cultivated ecologicalcrop in the north of China which is used to produce biodiesel fuel. It also possesses special medicinal value and has attracted keen interests of researchers to explore its bioactivity. PURPOSE: To extract the total triterpenoid saponins from the husk of X. sorbifolia (TSX) and investigate its effects on Alzheimer's disease (AD). STUDY DESIGN: TSX was prepared via modern extraction techniques...
February 15, 2017: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
https://www.readbyqxmd.com/read/28188798/in-silico-investigation-of-cycloartane-triterpene-derivatives-from-cimicifuga-dahurica-turcz-maxim-roots-for-the-development-of-potent-soluble-epoxide-hydrolase-inhibitors
#14
Nguyen Phuong Thao, Jang Hoon Kim, Bui Thi Thuy Luyen, Nguyen Tien Dat, Young Ho Kim
In our search for natural soluble epoxide hydrolase (sEH) inhibitors from plants, we found that an ethanolic extract of the roots of Cimicifuga dahurica (Turcz.) Maxim. significantly inhibits sEH in vitro. A phytochemical study on the dichloromethane fraction of C. dahurica resulted in the isolation of two new cycloartane triterpenoids (1 and 6), together with 13 known cycloartane analogues (2-5 and 7-15). The structures of compounds were determined by spectroscopic methods. All of the triterpenoid derivatives inhibited sEH enzymatic activity in a concentration-dependent manner, and 13 of the tested compounds showed significant activity...
February 7, 2017: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/28186749/aedes-aegypti-larvicidal-sesquiterpene-alkaloids-from-maytenus-oblongata
#15
Seindé Touré, Charlotte Nirma, Michael Falkowski, Isabelle Dusfour, Isabelle Boulogne, Arnaud Jahn-Oyac, Maïra Coke, Didier Azam, Romain Girod, Céline Moriou, Guillaume Odonne, Didier Stien, Emeline Houël, Véronique Eparvier
Four new sesquiterpene alkaloids (1-4) with a β-dihydroagrofuran skeleton and a new triterpenoid (5) were isolated from an ethyl acetate extract of Maytenus oblongata stems. Their structures were elucidated using 1D and 2D NMR spectroscopy as well as MS and ECD experiments. The M. oblongata stem EtOAc extract and the pure compounds isolated were tested for larvicidal activity against Aedes aegypti under laboratory conditions, and compounds 2 and 3 were found to be active.
February 10, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28184196/ag36-inhibits-human-breast-cancer-cells-proliferation-by-promotion-of-apoptosis-in-vitro-and-in-vivo
#16
Li-Hua Mu, Yu-Ning Wang, Dong-Xiao Wang, Jing Zhang, Li Liu, Xian-Zhe Dong, Yuan Hu, Ping Liu
AG36 is the biotransformation product of triterpenoid saponin from Ardisia gigantifolia stapf. In this study, the antitumor activity and underlying molecular mechanisms of AG36 against human breast MCF-7, MDA-MB-231, and SK-BR-3 cancer cells were investigated. AG36 inhibited the viability of MCF-7, MDA-MB-231, and SK-BR-3 cells in a dose and time-dependent manner, with an IC50 of approximately 0.73, 18.1, and 23.4 μM at 48 h, respectively. AG36 obviously induced apoptosis and G2/M arrest of all the three breast cancer cells...
2017: Frontiers in Pharmacology
https://www.readbyqxmd.com/read/28183232/triterpenoids-and-polysaccharide-peptides-enriched-ganoderma-lucidum-a-randomized-double-blind-placebo-controlled-crossover-study-of-its-antioxidation-and-hepatoprotective-efficacy-in-healthy-volunteers
#17
Hui-Fang Chiu, Hui-Yu Fu, Yan-Ying Lu, Yi-Chun Han, You-Cheng Shen, Kamesh Venkatakrishnan, Oksana Golovinskaia, Chin-Kun Wang
CONTEXT: Ganoderma lucidum (Leyss: Fr) Karst. (Polyporaceae) is an oriental medicinal fungus, commonly used in traditional Chinese medicine (TCM) for treating various condition or diseases such as hypertension, hyperglycaemia, hepatitis and cancer. OBJECTIVE: The current study examines whether triterpenoids and polysaccharide-enriched G. lucidum (GL) influence antioxidation and hepatoprotective efficacy by suppressing oxidative stress. MATERIALS AND METHODS: Forty-two healthy subjects (22 male and 20 female) were recruited and segregated into two groups as experimental or placebo and requested to intake GL (n = 21) or placebo (n = 21) capsule (225 mg; after lunch or dinner) for six consecutive months and vice versa with one month washout period in between...
December 2017: Pharmaceutical Biology
https://www.readbyqxmd.com/read/28178233/the-genome-of-chenopodium-quinoa
#18
David E Jarvis, Yung Shwen Ho, Damien J Lightfoot, Sandra M Schmöckel, Bo Li, Theo J A Borm, Hajime Ohyanagi, Katsuhiko Mineta, Craig T Michell, Noha Saber, Najeh M Kharbatia, Ryan R Rupper, Aaron R Sharp, Nadine Dally, Berin A Boughton, Yong H Woo, Ge Gao, Elio G W M Schijlen, Xiujie Guo, Afaque A Momin, Sónia Negrão, Salim Al-Babili, Christoph Gehring, Ute Roessner, Christian Jung, Kevin Murphy, Stefan T Arold, Takashi Gojobori, C Gerard van der Linden, Eibertus N van Loo, Eric N Jellen, Peter J Maughan, Mark Tester
Chenopodium quinoa (quinoa) is a highly nutritious grain identified as an important crop to improve world food security. Unfortunately, few resources are available to facilitate its genetic improvement. Here we report the assembly of a high-quality, chromosome-scale reference genome sequence for quinoa, which was produced using single-molecule real-time sequencing in combination with optical, chromosome-contact and genetic maps. We also report the sequencing of two diploids from the ancestral gene pools of quinoa, which enables the identification of sub-genomes in quinoa, and reduced-coverage genome sequences for 22 other samples of the allotetraploid goosefoot complex...
February 16, 2017: Nature
https://www.readbyqxmd.com/read/28173950/cytotoxic-triterpenoid-saponins-from-lysimachia-foenum-graecum
#19
Lu-Mei Dai, Ri-Zhen Huang, Bin Zhang, Jing Hua, Heng-Shan Wang, Dong Liang
Eleven oleanane-type triterpenoid saponins, foegraecumosides A-K, and eight known ones, were isolated from the aerial parts of Lysimachia foenum-graecum. Their structures were elucidated by spectroscopic data analyses and chemical methods. All isolated saponins were evaluated for their cytotoxicity against four human cancer cell lines (NCI-H460, MGC-803, HepG2, and T24). Seven saponins containing the aglycone cyclamiretin A exhibited moderate cytotoxicity against all tested human cancer cell lines, with IC50 values of 9...
February 4, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28173798/spasmogenic-and-spasmolytic-activity-of-rind-of-punica-granatum-linn
#20
Niaz Ali, Ayesha Jamil, Syed Wadood Ali Shah, Ismail Shah, Ghayour Ahmed
BACKGROUND: Rind of Punica granatum is traditionally used in treatment of abdominal cramps and various GIT disorders. So far spasmolytic activity of rind of Punica granatum has been reported using in vitro model. However, its mode of action is not explored yet. Therefore, the current work describes the possible mode of action for spasmolytic activity of methanolic extract of rind of Punica granatum (Pg. Cr). Acute toxicity study is also performed to determine its safe dose range. METHODS: Rind of Punica granatum was subjected to shade drying...
February 7, 2017: BMC Complementary and Alternative Medicine
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