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Triterpenoids

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https://www.readbyqxmd.com/read/28822185/-terpenoids-isolated-from-viburnum-ternatum
#1
Jiang Hu, Xia Mao, Nian-Hua Jing, Jun-You Shi, Hui-Qing Liu
Four iridoids (1-4), five iridoid glucosides (5-9), and three triterpenoids (10-12) were isolated from the ethyl acetate soluble fraction of 70% Me2CO extract of the aerial parts of Viburnum ternatum through various column chromatographies over silica gel, ODS, Sephadex LH-20 and MCI. Their structures were elucidated as ternatumin A (1), 2,9-dioxatricyclo[4.3.1.03,7]decanes (2), 7,10,2'-triacetylsuspensolide F (3), 7,10,2',3'-tetraacetylsuspensolide F (4), viburtinoside IV (5), viburtinoside II (6), viburtinoside B (7), luzonoside A (8), luzonoside B (9), 2α,3β,24-trihydroxy-12-ursen-28-oic acid (10), 6-hydroxy-20(29)-lupen-3-one (11), and pomalic acid (12) based on the their chromatographic properties, chemical and physicochemical methods, and spectroscopic data...
June 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/28820068/known-triterpenes-and-their-derivatives-as-scaffolds-for-the-development-of-new-therapeutic-agents-for-cancer
#2
Gregorio Peron, Giovanni Marzaro, Stefano Dall'Acqua
Plants produce several bioactive secondary metabolites whose are used as therapeutic agents to treat various diseases, among them cancer. Triterpenes are a category of secondary metabolites that exert inhibitory activity against multiple intracellular and extracellular targets in euchariotic cells. These targets are proteins involved in apoptosis, cell development and differentiation, angiogenesis, metastasis and inflammatory processes. The inhibition of their functions leads to decreased cellular growth, differentiation and migration, resulting in antitumor activity, as shown by the numerous published experimental results...
August 17, 2017: Current Medicinal Chemistry
https://www.readbyqxmd.com/read/28818803/polymorphic-characterization-and-bioavailability-of-20-r-25-methoxyl-dammarane-3%C3%AE-12%C3%AE-20-triol-a-novel-dammarane-triterpenoid-saponin-as-anticancer-agents
#3
Meng Ding, Lei Xu, Yumeng Zhang, Yuqing Zhao
This research, for the first time, obtained and reported three novel Form I, Form II, and Form III of 20(R)-25-methoxyl-dammarane-3β,12β,20-triol polymorphs, which were distinguished by PXRD, IR, DSC, and SEM. This study firstly exploited a rapid and feasible UHPLC-ESI-MS/MS method to determine plasma levels of 20(R)-25-OCH3-PPD within 4.5min. The composition of mobile phase was acetonitrile and 5mM ammonium acetate water (85:15, v/v) at a flow rate of 0.2mL/min on the BEH C18 Column (2.1mm×50mm, 1.7μm)...
August 8, 2017: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/28813688/isolation-and-characterization-of-non-sulfated-and-sulfated-triterpenoid-saponins-from-fagonia-indica
#4
Nayab Kanwal, Achyut Adhikari, Abdul Hameed, Rahman M Hafizur, Syed Ghulam Musharraf
Seven previously undescribed, sulfated triterpenoid glycosides, named nayabin A-G along with a known triterpenoid glycoside were isolated from the whole plant of Fagonia indica. Their structures were elucidated through spectral studies including 1D- ((1)H and (13)C), 2D-NMR spectroscopy (HSQC, HMBC, COSY and NOESY), and mass spectrometry (ESI-MS/MS). β-D-Glucopyranosyl 3β-hydroxy-23-O-β-D-glucopyranosyloxy-taraxast-20-en-28-oate, a known compound exerts glucose-dependent insulin secretory activity, which seems to exhibit a decreased risk of drug-induced hypoglycemia and may offer distinct advantages as anti-diabetic agent...
August 13, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28812026/evidence-of-immunosuppressive-and-th2-immune-polarizing-effects-of-antidiabetic-momordica-charantia-fruit-juice
#5
Rufine Fachinan, Adnette Fagninou, Magloire Pandoua Nekoua, Abdou Madjid Amoussa, Marius Adjagba, Latifou Lagnika, Anatole Lalèyè, Kabirou Moutairou, Akadiri Yessoufou
The mechanism of action of the antidiabetic capacity of Momordica charantia is still under investigation. Here, we assessed phytochemical compositions, antioxidant activity, and effects of total and filtered fruit and leafy stem juices of Momordica charantia on human T cell proliferation and differentiation through quantification of Th1/Th2 cytokines. In the absence of stimulation, total fruit and leafy stem juices induced significant T cell proliferation. Under PHA stimulation, both juices potentiated plant-induced T cell proliferation...
2017: BioMed Research International
https://www.readbyqxmd.com/read/28809973/competitive-affinity-based-proteome-profiling-and-imaging-to-reveal-potential-cellular-targets-of-betulinic-acid
#6
Haijun Guo, Jiaqian Xu, Piliang Hao, Ke Ding, Zhengqiu Li
Betulinic acid (BA), a pentacyclic triterpenoid natural product, has received considerable attention owing to the broad spectrum of biological activities such as anti-HIV, anti-inflammatory, and especially, antitumor. Despite numerous studies on the antitumor mechanisms over the past decade, the cellular targets in cancer cells remain obscure. Here, we developed two photoprobes, BA-1/BA-2, by attaching terminal alkyne-containing "minimalist" tetrazole/diazirine photo-crosslinkers (L3 and L7) at the C-3 and C-28 positions of BA, respectively, based on well-established structure-activity relationships...
August 15, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28807716/iritectol-g-a-novel-iridal-type-triterpenoid-from-iris-tectorum-displays-anti-epileptic-activity-in-vitro-through-inhibition-of-sodium-channels
#7
Chunlei Zhang, Juan Chen, Fang Zhao, Ruoyun Chen, Dequan Yu, Zhengyu Cao
Iritectol G, a novel iridal-type triterpenoid containing an uncommon tetrahydrofuran moiety, was isolated from the rhizomes of Iris tectorum. The structure was elucidated by comprehensive spectroscopic analysis. Iritectol G inhibited spontaneous and 4-aminopyridine-evoked calcium oscillations in primary cultured neocortical neurons with IC50 values of 8.2μM and 12.5μM, respectively. Further electrophysiological study demonstrated that iritectol G preferred to interact with inactivated state of voltage-gated sodium channel with an IC50 value of 7...
August 11, 2017: Fitoterapia
https://www.readbyqxmd.com/read/28802226/taraxerol-a-pentacyclic-triterpenoid-from-abroma-augusta-leaf-attenuates-diabetic-nephropathy-in-type-2-diabetic-rats
#8
Ritu Khanra, Niloy Bhattacharjee, Tarun K Dua, Ashis Nandy, Achintya Saha, Jatin Kalita, Prasenjit Manna, Saikat Dewanjee
Persistent hyperglycaemia coupled with inflammation plays an important role in the pathogenesis of diabetic nephropathy (DN). Present study examined the therapeutic potential of taraxerol isolated from the methanol extract of Abroma augusta leaf against DN using rodent model of type 2 diabetes (T2D). T2D was experimentally induced by high fat diet and a single low-single dose of streptozotocin (35mg/kg, i.p.). Accumulation of serum creatinine, urea, and uric acid, activation of lactate dehydrogenase and creatinin kinase, and release of urinary albumin represented the glomerular damage and the progression of nephropathy in T2D rats...
August 9, 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/28801631/rhodoterpenoids-a%C3%A2-c-three-new-rearranged-triterpenoids-from-rhododendron-latoucheae-by-hplc%C3%A2-ms%C3%A2-spe%C3%A2-nmr
#9
Fei Liu, Ya-Nan Wang, Yong Li, Shuang-Gang Ma, Jing Qu, Yun-Bao Liu, Chang-Shan Niu, Zhong-Hai Tang, Tian-Tai Zhang, Yu-Huan Li, Li Li, Shi-Shan Yu
Rhodoterpenoids A‒C (1‒3), three new rearranged triterpenoids, together with one new biogenetically related compound, rhodoterpenoid D (4), were isolated and efficiently elucidated from Rhododendron latoucheae by high-performance liquid chromatography-mass spectrometry-solid-phase extraction-nuclear magnetic resonance (HPLC‒MS‒SPE‒NMR). Compounds 1 and 2 possess an unprecedented skeleton with a 5/7/6/6/6-fused pentacyclic ring system, while compound 3 contains a unique 6/7/6/6/6-fused pentacyclic carbon backbone...
August 11, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28800422/cytotoxic-lanostane-triterpenoids-from-the-fruiting-bodies-of-piptoporus-betulinus
#10
Zeynep Tohtahon, Jingjing Xue, Jianxin Han, Yushuang Liu, Huiming Hua, Tao Yuan
Chemical investigation of a bioactive methanolic extract of the fruiting bodies of Piptoporus betulinus led to the isolation of five previously undescribed lanostane triterpenoids named piptolinic acids A-E, as well as five known lanostane triterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopic and HRESIMS analysis. Piptolinic acid A with an unusual moiety (3-hydroxy-4-methoxycarbonyl-3-methylbutyryloxy) at C-3 exhibited comparable cytotoxic activity against human promyelocytic leukemia cell line HL-60 (IC50 = 1...
August 8, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28800421/lanostane-type-triterpenoids-from-the-fruiting-body-of-ganoderma-calidophilum
#11
Sheng-Zhuo Huang, Qing-Yun Ma, Fan-Dong Kong, Zhi-Kai Guo, Cai-Hong Cai, Li-Li Hu, Li-Man Zhou, Qi Wang, Hao-Fu Dai, Wen-Li Mei, You-Xing Zhao
To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC50 values of 7...
August 8, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28798953/the-ethanolic-stem-bark-extract-of-antrocaryon-micraster-inhibits-carrageenan-induced-pleurisy-and-pedal-oedema-in-murine-models-of-inflammation
#12
Leslie B Essel, David D Obiri, Newman Osafo, Aaron O Antwi, Babatunde M Duduyemi
We investigated the antioxidant and anti-inflammatory effects of a 70% v/v ethanol extract of the stem bark of Antrocaryon micraster on murine models of carrageenan-induced pleurisy and paw oedema. Rat pleural fluid was analysed for volume, protein content, and leucocytes, while lung histology was assessed for damage. Lung tissue homogenates were assayed for glutathione (GSH), superoxide dismutase (SOD), catalase (CAT), malondialdehyde (MDA), and myeloperoxidase (MPO). Phytochemical analysis was carried out on the stem bark...
2017: International Scholarly Research Notices
https://www.readbyqxmd.com/read/28796242/the-triterpenoid-cddo-imidazolide-ameliorates-mouse-liver-ischemia-reperfusion-injury-through-activating-the-nrf2-ho-1-pathway-enhanced-autophagy
#13
Dongwei Xu, Lili Chen, Xiaosong Chen, Yankai Wen, Chang Yu, Jufang Yao, Hailong Wu, Xin Wang, Qiang Xia, Xiaoni Kong
Nuclear factor erythroid 2-related factor 2 (Nrf2)-mediated induction of antioxidants has been implicated to have protective roles in ischemia-reperfusion (I/R) injury in many animal models. However, the in vivo effects of CDDO-imidazole (CDDO-Im) (1-[2-cyano-3-,12-dioxooleana-1,9(11)-dien-28-oyl] imidazole), a Nrf2 activator, in hepatic I/R injury is lacking and its exact molecular mechanisms are still not very clear. The goals of this study were to determine whether CDDO-Im can prevent liver injury induced by I/R in the mouse, and to elucidate the molecular target of drug action...
August 10, 2017: Cell Death & Disease
https://www.readbyqxmd.com/read/28792469/cytotoxic-and-antiviral-triterpenoids-from-the-mangrove-plant-sonneratia-paracaseolaris
#14
Kai-Kai Gong, Ping-Lin Li, Dan Qiao, Xing-Wang Zhang, Mei-Jun Chu, Guo-Fei Qin, Xu-Li Tang, Guo-Qiang Li
A chemical investigation was conducted on the aerial parts of the mangrove plant Sonneratia paracaseolaris, yielding five new triterpenoid paracaseolins A-E (1-4, and 11) together with twelve known analogues (5-10, 12-17). Their structures were established by extensive spectroscopic methods and comparisons their spectroscopic data with those of the known related compounds. The cytotoxicities against P388, HeLa, A549, and K562 tumor cell lines and anti-H1N1 (Influenza A virus) activities for the isolates were evaluated...
August 9, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28783356/chemical-constituents-of-propolis-from-vietnamese-trigona-minor-and-their-antiausterity-activity-against-the-panc-1-human-pancreatic-cancer-cell-line
#15
Hai X Nguyen, Mai T T Nguyen, Nhan T Nguyen, Suresh Awale
The ethanol extract of propolis from the Vietnamese stingless bee Trigona minor possessed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells in nutrient-deprived medium, with a PC50 value of 14.0 μg/mL. Chemical investigation of this extract led to the isolation of 15 cycloartane-type triterpenoids, including five new compounds (1-5), and a lanostane-type triterpenoid. The structures of the new compounds were elucidated on the basis of NMR spectroscopic analysis. Among the isolated compounds, 23-hydroxyisomangiferolic acid B (5) and 27-hydroxyisomangiferolic acid (13) exhibited the most potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrition-deprived conditions, with PC50 values of 4...
August 7, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28782948/design-synthesis-and-cancer-cell-growth-inhibitory-activity-of-triphenylphosphonium-derivatives-of-the-triterpenoid-betulin
#16
Olga V Tsepaeva, Andrey V Nemtarev, Timur I Abdullin, Leysan R Grigor'eva, Elena V Kuznetsova, Rezeda A Akhmadishina, Liliya E Ziganshina, Hanh H Cong, Vladimir F Mironov
A series of new triphenylphosphonium (TPP) derivatives of the triterpenoid betulin (1, 3-lup-20(29)-ene-3β,28-diol) have been synthesized and evaluated for cytotoxic effects against human breast cancer (MCF-7), prostate adenocarcinoma (PC-3), vinblastine-resistant human breast cancer (MCF-7/Vinb), and human skin fibroblast (HSF) cells. The TPP moiety was applied as a carrier group through the acyl linker at the 28- or 3- and 28-positions of betulin to promote cellular and mitochondrial accumulation of the resultant compounds...
August 7, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28781969/immunomodulatory-effects-of-taiwanese-neolitsea-species-on-th1-and-th2-functionality
#17
Yin-Hua Cheng, Ying-Chi Lin, Ih-Sheng Chen, Sian-De Liu, Jih-Heng Li, Chia-Chi Wang
Neolitsea species, medicinal plants belonging to Lauraceae, contain rich alkaloids, steroids, sesquiterpenoids, and triterpenoids which possess antimicrobial, antioxidant, and anti-inflammatory bioactivities. However, species differences in the immunomodulatory effects and evidence pertaining to the effects of Neolitsea species on adaptive immunity are scarce. This study aimed to evaluate the immunomodulatory properties of ten Taiwanese Neolitsea plants on T helper (Th) cell functionality, especially Th1 and Th2...
2017: Journal of Immunology Research
https://www.readbyqxmd.com/read/28771546/de-novo-leaf-and-root-transcriptome-analysis-to-identify-putative-genes-involved-in-triterpenoid-saponins-biosynthesis-in-hedera-helix-l
#18
Huapeng Sun, Fang Li, Zijian Xu, Mengli Sun, Hanqing Cong, Fei Qiao, Xiaohong Zhong
Hedera helix L. is an important traditional medicinal plant in Europe. The main active components are triterpenoid saponins, but none of the potential enzymes involved in triterpenoid saponins biosynthesis have been discovered and annotated. Here is reported the first study of global transcriptome analyses using the Illumina HiSeq™ 2500 platform for H. helix. In total, over 24 million clean reads were produced and 96,333 unigenes were assembled, with an average length of 1385 nt; more than 79,085 unigenes had at least one significant match to an existing gene model...
2017: PloS One
https://www.readbyqxmd.com/read/28766764/bioactive-triterpenes-from-the-root-of-salvia-miltiorrhiza-bunge
#19
Nguyen Huu Tung, Kensuke Nakajima, Takuhiro Uto, Nguyen Thanh Hai, Dinh Doan Long, Tomoe Ohta, Shigeru Oiso, Hiroko Kariyazono, Yukihiro Shoyama
Danshen (Salvia miltiorrhiza) is a well-known medicinal herb in the oriental medicine. The current study on bioactive triterpenoid in the root of S. miltiorrhiza led to the isolation of a new highly hydroxylated ursane-type triterpene, urs-12-ene-2α,3β,7β,16α-tetraol (1) and five known ones including 2β-hydroxypomolic acid (2), maslinic acid (3), asiatic acid (4), ursolic acid (5), and oleanolic acid (6). Their structures were elucidated on the basis of extensive spectroscopic analyses and comparison with literature data...
August 2, 2017: Phytotherapy Research: PTR
https://www.readbyqxmd.com/read/28766112/oleanolic-acid-and-ursolic-acid-as-potential-inhibitors-of-human-salivary-%C3%AE-amylase-insights-from-in-vitro-assays-and-in-silico-simulations
#20
Jiachen Sun, Shengjie Dong, Yueting Wu, Hui Zhao, Xia Li, Wenyuan Gao
It is known that inhibiting α-amylase, an important enzyme in digestion of starch and glycogen, is a useful strategy for treating disorders in carbohydrate uptake. Two natural components distributed in many fruits and plants, oleanolic acid and ursolic acid, are endowed with important pharmacological activities and wide therapeutic possibilities. Until now, only a tiny fraction of their applications have been identified and exploited. Our in vitro inhibition studies demonstrated that oleanolic acid and ursolic acid non-competitively inhibit the activity and function of human salivary α-amylase...
August 2017: Journal of Molecular Modeling
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