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Triterpenoids

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https://www.readbyqxmd.com/read/28445411/discovery-of-farnesoid-x-receptor-antagonists-based-on-a-library-of-oleanolic-acid-3-o-esters-through-diverse-substituent-design-and-molecular-docking-methods
#1
Shao-Rong Wang, Tingting Xu, Kai Deng, Chi-Wai Wong, Jinsong Liu, Wei-Shuo Fang
The pentacyclic triterpene oleanolic acid (OA, 1) with known farnesoid X receptor (FXR) modulatory activity was modified at its C-3 position to find new FXR-interacting agents. A diverse substitution library of OA derivatives was constructed in silico through a 2D fingerprint similarity cluster strategy. With further docking analysis, four top-scored OA 3-O-ester derivatives were selected for synthesis. The bioassay results indicated that all four compounds 3 inhibited chenodeoxycholic acid (CDCA)-induced FXR transactivation in a concentration-dependent mode...
April 26, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28445407/application-of-uhplc-esi-q-tof-ms-to-identify-multiple-constituents-in-processed-products-of-the-herbal-medicine-ligustri-lucidi-fructus
#2
Hui Li, Weifeng Yao, Qinan Liu, Jia Xu, Beihua Bao, Mingqiu Shan, Yudan Cao, Fangfang Cheng, Anwei Ding, Li Zhang
Ligustri Lucidi Fructus (LLF), the fruit of Ligustrum lucidum Ait. (Oleaceae), has been used as a common herbal medicine in clinical practice in China for nearly 2000 years. In most cases, LLF is prescribed in decoctions in the form of processed products rather than crude drugs. In this study, an ultra-high performance liquid chromatography coupled with electrospray ionization-quadrupole-time of flight-mass spectrometry (UHPLC-ESI-Q-TOF-MS) method was established for rapid separation and identification of multiple constituents in the 80% methanol extract of processed-LLF...
April 26, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28443465/bauerenol-a-triterpenoid-from-indian-suregada-angustifolia-induces-reactive-oxygen-species-mediated-p38mapk-activation-and-apoptosis-in-human-hepatocellular-carcinoma-hepg2-cells
#3
Perumal Sathish Kumar, Madepalli Byrappa Gowdu Viswanathan, Muthappan Venkatesan, Kedike Balakrishna
The triterpenoid, bauerenol, from Suregada angustifolia (Baill. ex Muell.-Arg.) Airy Shaw (Euphorbiaceae) was screened for anti-cancer property using hepatocellular carcinoma cell line, HepG2. Bauerenol exhibited growth inhibitory and apoptosis inducing potential against HepG2 cancer cells. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide cytotoxic assay revealed that bauerenol treatment significantly reduced the growth of HepG2 cells in a time- and dose-dependent manner with 50% growth inhibitory concentration doses of 45 and 25 µg/mL at 24 and 48 h treatments, respectively...
April 2017: Tumour Biology: the Journal of the International Society for Oncodevelopmental Biology and Medicine
https://www.readbyqxmd.com/read/28441883/chemical-constituents-from-gueldenstaedtia-verna-and-their-anti-inflammatory-activity
#4
Xin Liu, Chengle Yin, Yue Cao, Jinge Zhou, Tao Wu, Zhihong Cheng
A new triterpenoid glycoside (1) and 15 known compounds (2-16) were isolated from the whole plants of Gueldenstaedtia verna. The new compound (1) was identified as complogenin 22-O-β-d-glucopyranoside by extensive spectroscopic techniques including 1D ((1)H and (13)C) and 2D NMR experiments (HSQC, HMBC and NOESY), HR-DART-MS and chemical methods. Most of the isolates were evaluated for their inhibitory activities on LPS-induced NO production in RAW 264.7 cells. The inhibitory effects of the active compounds, sulphuretin (8) and (22E,24S)-5α,8α-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol (13), on the production of pro-inflammatory mediators (including IL-6, IL1β and PGE2) were further estimated in vitro by ELISA in RAW 264...
April 25, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28441767/inhibitory-effect-of-triterpenoids-from-panax-ginseng-on-coagulation-factor-x
#5
Lingxin Xiong, Zeng Qi, Bingzhen Zheng, Zhuo Li, Fang Wang, Jinping Liu, Pingya Li
Enzymes involved in the coagulation process have received great attention as potential targets for the development of oral anti-coagulants. Among these enzymes, coagulation factor Xa (FXa) has remained the center of attention in the last decade. In this study, 16 ginsenosides and two sapogenins were isolated, identified and quantified. To determine the inhibitory potential on FXa, the chromogenic substrates method was used. The assay suggested that compounds 5, 13 and 18 were mainly responsible for the anti-coagulant effect...
April 24, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28441516/epoxynemanione-a-nemanifuranones-a-f-and-nemanilactones-a-c-from-nemania-serpens-an-endophytic-fungus-isolated-from-riesling-grapevines
#6
Ashraf Ibrahim, Dan Sørensen, Hilary A Jenkins, Linda Ejim, Alfredo Capretta, Mark W Sumarah
Ten polyketide specialized metabolites, epoxynemanione A, nemanifuranones A-F, and nemanilactones A-C, were isolated from the culture filtrate of Nemania serpens (Pers.) Grey (1821), an endophytic fungus from a Riesling grapevine (Vitis vinifera) found in Canada's Niagara region. Additionally, four known metabolites 2-(hydroxymethyl)-3-methoxy-benzoic acid, phyllostine, 5-methylmellein and a nordammarane triterpenoid were isolated. A related known metabolite 2,3-dihydro-2-hydroxy-2,4-dimethyl-5-trans-propenylfuran-3-one has also been included for structural and biological comparison to the nemanifuranones...
April 22, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28438659/the-nrf2-activator-dh404-attenuates-adverse-ventricular-remodelling-post-myocardial-infarction-by-modifying-redox-signalling
#7
Kristen J Bubb, Cindy Kok, Owen Tang, Nathalie B Rasko, Asa Birna Birgisdottir, Thomas Hansen, Rebecca Ritchie, Ravinay Bhindi, Scott A Reisman, Colin Meyer, Keith Ward, Keyvan Karimi Galougahi, Gemma A Figtree
BACKGROUND: The novel synthetic triterpenoid, bardoxolone methyl, has the ability to upregulate cytoprotective proteins via induction of the nuclear factor erythroid-2-related factor 2 (Nrf2) pathway. This makes it a promising therapeutic agent in disease states characterized by dysregulated oxidative signalling. We have examined the effect of a Nrf2 activator, dihydro-CDDO-trifluoroethyl amide (DH404), a derivative of bardoxolone methyl, on post-infarct cardiac remodeling in rats. METHODS/RESULTS: DH404, administered from day 2 post myocardial infarction (MI: 30 min transient ischemia followed by reperfusion) resulted in almost complete protection against adverse ventricular remodeling as assessed at day 28 (left ventricular end-systolic area: sham 0...
April 21, 2017: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/28438039/anti-complementary-constituents-of-anchusa-italica
#8
Yu-Zhen Hou, Kui-Kui Chen, Xi-Ling Deng, Ze-Long Fu, Dao-Feng Chen, Qi Wang
Activity-guided fractionation for complement inhibitors led to the isolation of 24 known compounds from Anchusa italica. Chemical types include eight megastigmane compounds, five triterpenoid compounds, five lignan compounds, three flavonoid compounds, two alkaloid compounds and one phenthyl alcohol compound. Among which, a lignan (medioresinol), an alkaloid (5-hydroxypyrrolidin-2-one) and a flavonoid (5-hydroxyl-3', 4', 6, 7-tetramethoxy flavone) exhibited better anticomplementary effects with CH50 values ranging from 0...
April 24, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28434194/cytotoxic-triterpenoids-from-the-stalks-of-microtropis-triflora
#9
Xiao-Wei Zhang, Kui-Wu Wang, Man-Qing Zhou
Bioassay-guided phytochemcal investigation of the stalks of Microtropis triflora Merr. et Freem led to the isolation of ten triterpenes 1-10, including one novel compound 24-epoxy-2α, 24-dihydroxy-29-friedelanoic acid (1). Their chemical structures were identified on the basis of spectroscopic analysis, including HRESI mass spectrometry, 1D and 2D NMR ((1) H, (13) C, (1) H-(1) H COSY, HSQC, HMBC and NOESY), and by comparison with the data reported. The cytotoxicities of the compounds 1-10 against a panel of cultured human tumor cell lines (Bcap37, SMMC7721, Hela, CNE) were evaluated...
April 23, 2017: Chemistry & Biodiversity
https://www.readbyqxmd.com/read/28432923/triterpenoid-saponins-from-the-roots-of-spergularia-marginata
#10
David Pertuit, Mustafa Larshini, Malika Aitsidi Brahim, Mohamed Markouk, Anne-Claire Mitaine-Offer, Thomas Paululat, Stéphanie Delemasure, Patrick Dutartre, Marie-Aleth Lacaille-Dubois
Phytochemical investigations of the roots of Spergularia marginata had led to the isolation of four previously undescribed triterpenoid saponins, a known one and one spinasterol glycoside. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 4)-3-O-sulfate-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranosyl 21-O-acetyl acacic acid...
April 19, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28423926/antibacterial-activity-of-a-triterpenoid-saponin-from-the-stems-of-caesalpinia-pulcherrima-linn
#11
Nidhi Asati, R N Yadava
A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-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. The new compound 1 has m.p. 272-274°C, m.f. C46H74O17, [M](+) m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses...
April 20, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28423649/stellettin-b-induces-apoptosis-in-human-chronic-myeloid-leukemia-cells-via-targeting-pi3k-and-stat5
#12
Yali Chen, Qianxiang Zhou, Lei Zhang, Yuxu Zhong, Guanwei Fan, Zhe Zhang, Ran Wang, Meihua Jin, Yuling Qiu, Dexin Kong
Novel agents are still urgently expected for therapy of chronic myeloid leukemia (CML). The in vitro anti-leukemia activity of Stellettin B (Stel B), a triterpenoid we isolated from marine sponge Jaspis stellifera, on human CML K562 and KU812 cells was recently investigated. Stel B inhibited K562 and KU812 cell proliferation with IC50 as 0.035 μM and 0.95 μM respectively. While no obvious cell cycle arrest was observed, apoptosis was induced in K562 cells after Stel B treatment. The Stel B-induced apoptosis might be in mitochondrial pathway, with increase of Bad and Bax, decrease of Bcl-2 and activation of caspase-9...
March 7, 2017: Oncotarget
https://www.readbyqxmd.com/read/28420183/anti-proliferative-effect-of-triterpenoidal-glycosides-from-the-roots-of-anemone-vitifolia-through-a-pro-apoptotic-way
#13
Changcai Bai, Yunyun Ye, Xiao Feng, Ruifeng Bai, Lu Han, Xiuping Zhou, Xinyao Yang, Pengfei Tu, Xingyun Chai
A cytotoxicity-guided phytochemical investigation of Anemone vitifolia roots led to the isolation of six oleanane saponins (1-6), which were reported from the species for the first time. Their structures were determined by comparing its MS and NMR data with those in literature. Compounds 1-4 showed significant inhibitory effects on the proliferation of hepatocellular carcinoma HepG2 cells with IC50 values ranging from 2.0 to 8.5 μM, compared to positive control methotrexate with IC50 value of 15.8 μM. Flow cytometry analysis revealed that compounds 1-4 exerted anti-proliferative effects through a pro-apoptotic way of hepatocellular carcinoma cells...
April 17, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28407906/antioxidant-and-antibiofilm-activities-of-secondary-metabolites-from-ziziphus-jujuba-leaves-used-for-infusion-preparation
#14
Silvia Damiano, Martino Forino, Arpan De, Luca A Vitali, Giulio Lupidi, Orazio Taglialatela-Scafati
Ziziphus jujuba Mill., jujube, leaf infusions are popular bedtime beverages as they improve sleep by soothing the nerves. With the aim of providing further insights into the polyphenol content of jujube leaf infusion and their antioxidant activities, a 2,2-diphenyl-1-picrylhydrazyl (DPPH)-guided purification of the aqueous extract of Z. jujuba Mill. leaves was conducted. Three major antioxidant polyphenols (i.e. quercitrin, catechin and gallocatechin) of the leaves were identified. In addition, a significant antibiofilm bioactivity against Streptococcus mutans, a causative agent of human dental caries, was detected for the aqueous leaf extract and its bio-guided separation resulted in the identification of the lupane triterpenoid alphitolic acid as the main antibiofilm metabolite...
September 1, 2017: Food Chemistry
https://www.readbyqxmd.com/read/28403639/a-new-cycloartane-triterpenoid-glycoside-from-souliea-vaginata
#15
Hai-Feng Wu, Xin Liu, Yin-Di Zhu, Jing Zhou, Ying-Ying Gong, Guo-Xu Ma, Xu-Dong Xu, Yi-Lin Liu, Zheng-Hong Luo, Di-Zhao Chen, Qiong-Yu Zou, Zi-Jian Zhao
One new cycloartane triterpenoid glycoside, soulieoside Q (1), together with four known compounds (2-5) were isolated from the ethanolic extract of the rhizomes of Souliea vaginata Maxim. The structure of the new compound was determined by extensive spectroscopic analysis including 1D and 2D NMR and HRESIMS, as well as chemical methods. Compound 1 was evaluated for its cytotoxic activities against HepG2 and A549 cancer cell lines.
April 13, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28402700/characterizing-novel-anti-oncogenic-triterpenoids-from-ganoderma
#16
Xiangmin Li, Yizhen Xie, Burton B Yang
No abstract text is available yet for this article.
April 12, 2017: Cell Cycle
https://www.readbyqxmd.com/read/28393564/an-efficient-semi-synthesis-of-1-hydroxyl-oleanolic-acid-analogs
#17
Da-Hui Zhang, Wei-Shuo Fang, Shao-Rong Wang
An efficient route for the semi-synthesis of either 1α- or 1β-OH epimers of 1-hydroxy-3-deoxyolean-12-en-28-oic acid (1), 6-8 steps from oleanolic acid is reported. The synthesis involves stereoselective formation of α,β-unsaturated epoxy ketone and subsequent Wharton reaction as key steps, offering a new access to the 1-O-substituted oleanolic acid-type pentacyclic triterpenoids.
April 9, 2017: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/28392270/new-ursane-type-triterpenoids-from-clerodendranthus-spicatus
#18
Yong Luo, Li-Zhi Cheng, Qi Luo, Yong-Ming Yan, Shu-Mei Wang, Qin Sun, Yong-Xian Cheng
Five new ursane-type triterpenoids, spicatusoids A-E (1, 3-6), and three known ones (2, 7, and 8), and a known oleanane-type triterpenoid (9) were isolated from the aerial parts of Clerodendranthus spicatus. Their structures were elucidated by spectroscopic methods. In particular, the structure of 3 including its absolute configuration was confirmed by single-crystal X-ray diffraction analysis. Cell viability of all the compounds against rat kidney fibroblast cells (NRK-49F) with or without TGF-β1 induction and human cancer cells (HL-60, SMMC-7721, A-549, MCF-7, and SW-480) was examined by using MTT or MST assays...
April 7, 2017: Fitoterapia
https://www.readbyqxmd.com/read/28390973/neolignans-and-serratane-triterpenoids-with-inhibitory-effects-on-xanthine-oxidase-from-palhinhaea-cernua
#19
Jing Li, Ping-Sheng Xu, Lei-Hong Tan, Zhen-Xing Zou, Yi-Kun Wang, Hong-Ping Long, Gan Zhou, Guang Li, Kang-Ping Xu, Gui-Shan Tan
Three new neolignans, lycocernuasides B-D (1-3), three new serratane triterpenoids, lycernuic ketones D (8) and E (9), and lycernuic A (10), together with six known compounds, were isolated from the 75% aqueous EtOH extract of Palhinhaea cernua. Their structures and absolute configurations were established primarily by NMR, HRESIMS and circular dichroism (CD). All compounds were evaluated the inhibitory activities of xanthine oxidase. Compounds 1-3 displayed moderate inhibitory effects on xanthine oxidase with IC50 values of 30...
April 5, 2017: Fitoterapia
https://www.readbyqxmd.com/read/28390176/cucurbitacin-b-protects-against-pressure-overload-induced-cardiac-hypertrophy
#20
Yang Xiao, Zheng Yang, Qing-Qing Wu, Xiao-Han Jiang, Yuan Yuan, Wei Chang, Zhou Yan Bian, Jin Xiu Zhu, Qi-Zhu Tang
Lack of effective anti-cardiac hypertrophy drugs creates a major cause for the increasing prevalence of heart failure. In the present study, we determined the anti-hypertrophy and anti-fibrosis potential of a natural plant triterpenoid, Cucurbitacin B both in vitro and in vivo. Aortic banding (AB) was performed to induce cardiac hypertrophy. After 1 week of surgery, mice were receive cucurbitacin B treatment (Gavage, 0.2 mg/kg body weight/2 day). Afer 4 weeks of AB, cucurbitacin B demonstrated a strong anti- hypertrophy and anti-fibrosis ability as evidenced by decreased of heart weight, myocardial cell cross-sectional area and interstitial fibrosis, ameliorated of systolic and diastolic abnormalities, normalized in gene expression of hypertrophic and fibrotic markers, reserved microvascular density in pressure overload induced hypertrophic mice...
April 8, 2017: Journal of Cellular Biochemistry
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