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diterpenoid alkaloid

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https://www.readbyqxmd.com/read/27860043/synthesis-of-atisine-ajaconine-denudatine-and-hetidine-diterpenoid-alkaloids-by-a-bioinspired-approach
#1
Xiao-Huan Li, Min Zhu, Zhi-Xiu Wang, Xiao-Yu Liu, Hao Song, Dan Zhang, Feng-Peng Wang, Yong Qin
A unified approach to four different (atisine, ajaconine, denudatine, and hetidine) diterpenoid alkaloid skeletons was developed and applied to the total synthesis of the natural products dihydroajaconine (2, atisine type) and gymnandine (4, denudatine type). The synthesis features a biogenetically inspired strategy that relies on C-H oxidation, aza-pinacol coupling, and aza-Prins cyclization as key steps.
November 17, 2016: Angewandte Chemie
https://www.readbyqxmd.com/read/27834099/chemical-composition-and-evaluation-of-prolyl-oligopeptidase-and-acetylcholinesterase-inhibitory-activities-of-leonurus-sibiricus-l-from-brazil
#2
Lucimara L Zachow, Janaína M Ávila, Geovane A Saldanha, Marco A Mostardeiro, Ubiratan F da Silva, Ademir F Morel, Ionara I Dalcol
Chemical investigation of the aerial parts of Leonurus sibiricus L. used in Brazilian folk medicine led to the identification of the following constituents: the labdane-type diterpenoid leojaponin, the phytosterols β-sitosterol and β-sitosterol glucoside and the alkaloid leonurine. The crude extracts obtained from methanol and methanol/1% HCl and pure compounds isolated from L. sibirius were investigated as acetylcholinesterase (AChE) and prolyl oligopeptidase (POP) inhibitors. Extracts obtained by maceration were active against POP (53-58%), but showed weak activity against AChE...
November 11, 2016: Natural Product Research
https://www.readbyqxmd.com/read/27768308/synthesis-of-chamobtusin-a-from-dehydroabietylamine
#3
Naoki Mori, Kazuma Kuzuya, Hidenori Watanabe
Chamobtusin A, a unique diterpene alkaloid isolated from Chamaecyparis obtusa cv. tetragon, is considered to be biosynthesized from an abietane diterpenoid. On the basis of this biosynthetic hypothesis, ferruginol (15) was synthesized from (+)-dehydroabietylamine, and then biomimetically transformed into (-)-chamobtusin A in 6 steps (12 steps from (+)-dehydroabietylamine).
October 21, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27761113/ester-hydrolysis-differentially-reduces-aconitine-induced-anti-hypersensitivity-and-acute-neurotoxicity-involvement-of-spinal-microglial-dynorphin-expression-and-implications-for-aconitum-processing
#4
Teng-Fei Li, Nian Gong, Yong-Xiang Wang
Aconitines, including bulleyaconitine A, probably the most bioactive and abundant alkaloids in Aconitum plant, are a group of diester C19-diterpenoid alkaloids with one acetylester group attached to C8 of the diterpenoid skeleton and one benzoylester group to C14. Hydrolysis of both groups is involved in the processing of Aconitum, a traditional Chinese medicinal approach. We recently demonstrated that bulleyaconitine A produced anti-hypersensitivity, which was mediated by stimulation of spinal microglial dynorphin A expression...
2016: Frontiers in Pharmacology
https://www.readbyqxmd.com/read/27686870/a-new-c20-diterpenoid-alkaloid-from-the-lateral-roots-of-aconitum-carmichaeli
#5
Jing Yu, Tian-Peng Yin, Jia-Peng Wang, Rui-Feng Mei, Le Cai, Zhong-Tao Ding
A new C20-diterpenoid alkaloid carmichaedine (1) and six known alkaloids (2-7) were isolated from the lateral roots of Aconitum carmichaeli. Their structures were established on the basis of extensive spectroscopic analyses. Compound 1 exhibited potent antibacterial activity against Bacillus subtilis with minimum inhibitory concentration of 8 μg/mL.
August 11, 2016: Natural Product Research
https://www.readbyqxmd.com/read/27626453/the-search-for-herbal-antibiotics-an-in-silico-investigation-of-antibacterial-phytochemicals
#6
Mary Snow Setzer, Javad Sharifi-Rad, William N Setzer
Recently, the emergence and spread of pathogenic bacterial resistance to many antibiotics (multidrug-resistant strains) have been increasing throughout the world. This phenomenon is of great concern and there is a need to find alternative chemotherapeutic agents to combat these antibiotic-resistant microorganisms. Higher plants may serve as a resource for new antimicrobials to replace or augment current therapeutic options. In this work, we have carried out a molecular docking study of a total of 561 antibacterial phytochemicals listed in the Dictionary of Natural Products, including 77 alkaloids (17 indole alkaloids, 27 isoquinoline alkaloids, 4 steroidal alkaloids, and 28 miscellaneous alkaloids), 99 terpenoids (5 monoterpenoids, 31 sesquiterpenoids, 52 diterpenoids, and 11 triterpenoids), 309 polyphenolics (87 flavonoids, 25 chalcones, 41 isoflavonoids, 5 neoflavonoids, 12 pterocarpans, 10 chromones, 7 condensed tannins, 11 coumarins, 30 stilbenoids, 2 lignans, 5 phenylpropanoids, 13 xanthones, 5 hydrolyzable tannins, and 56 miscellaneous phenolics), 30 quinones, and 46 miscellaneous phytochemicals, with six bacterial protein targets (peptide deformylase, DNA gyrase/topoisomerase IV, UDP-galactose mutase, protein tyrosine phosphatase, cytochrome P450 CYP121, and NAD⁺-dependent DNA ligase)...
September 12, 2016: Antibiotics
https://www.readbyqxmd.com/read/27577933/bullatine-a-stimulates-spinal-microglial-dynorphin-a-expression-to-produce-anti-hypersensitivity-in-a-variety-of-rat-pain-models
#7
Qian Huang, Xiao-Fang Mao, Hai-Yun Wu, Teng-Fei Li, Ming-Li Sun, Hao Liu, Yong-Xiang Wang
BACKGROUND: Aconiti brachypodi Radix (Xue-shang-yi-zhi-hao) has been prescribed to manage chronic pain, arthritis, and traumatic injuries. Bullatine A, a C20-diterpenoid alkaloid, is one of its principle effective compounds. This study aimed to investigate the anti-hypersensitivity of bullatine A in a variety of rat pain models and explore its mechanisms of action. METHODS: Rat neuropathic pain, inflammatory pain, diabetic neuropathic pain, and bone cancer pain models were used...
2016: Journal of Neuroinflammation
https://www.readbyqxmd.com/read/27571684/simultaneous-determination-of-ten-aconitum-alkaloids-in-rat-tissues-by-uhplc-ms-ms-and-its-application-to-a-tissue-distribution-study-on-the-compatibility-of-heishunpian-and-fritillariae-thunbergii-bulbus
#8
Bin Yang, Yanyan Xu, Yuanyuan Wu, Huanyu Wu, Yuan Wang, Lei Yuan, Jiabin Xie, Yubo Li, Yanjun Zhang
A rapid, sensitive and selective ultra-high performance liquid chromatography with tandem mass spectrometry (UHPLC-MS/MS) method was developed and validated for simultaneous determination of ten Aconitum alkaloids in rat tissues. The tissue samples were prepared by a simple procedure protein precipitation with acetonitrile containing 0.1% acetic acid and separated on an Agilent XDB C18 column (4.6 mm×50mm, 1.8μm) using gradient elution with a mobile phase consisting of water and acetonitrile (both containing 0...
October 15, 2016: Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
https://www.readbyqxmd.com/read/27525345/syntheses-of-denudatine-diterpenoid-alkaloids-cochlearenine-n-ethyl-1%C3%AE-hydroxy-17-veratroyldictyzine-and-paniculamine
#9
Kevin G M Kou, Beryl X Li, Jack C Lee, Gary M Gallego, Terry P Lebold, Antonio G DiPasquale, Richmond Sarpong
The denudatine-type diterpenoid alkaloids cochlearenine, N-ethyl-1α-hydroxy-17-veratroyldictyzine, and paniculamine have been synthesized for the first time (25, 26, and 26 steps from 16, respectively). These syntheses take advantage of a common intermediate (8) that we have previously employed in preparing aconitine-type natural products. The syntheses reported herein complete the realization of a unified strategy for the preparation of C20, C19, and C18 diterpenoid alkaloids.
August 31, 2016: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/27405107/diterpenoid-alkaloids-from-delphinium-ajacis-and-their-anti-rsv-activities
#10
Li Yang, Yu-Bo Zhang, Ling Zhuang, Tao Li, Neng-Hua Chen, Zhong-Nan Wu, Pan Li, Yao-Lan Li, Guo-Cai Wang
Five new diterpenoid alkaloids, ajacisines A-E (1-5), were isolated from Delphinium ajacis, along with seven known alkaloids (6-12). On the basis of their spectral data (IR, UV, HR-ESI-MS, 1D and 2D NMR) and chemical properties, the structures of compounds 1-12 were identified. All isolated compounds were evaluated for their in vitro antiviral activities against respiratory syncytial virus, and compounds 3-5 and 8 exhibited moderate to weak effects with IC50 values of 75.2 ± 1.1, 35.1 ± 0.6, 10...
July 12, 2016: Planta Medica
https://www.readbyqxmd.com/read/27378926/toxic-constituents-index-a-toxicity-calibrated-quantitative-evaluation-approach-for-the-precise-toxicity-prediction-of-the-hypertoxic-phytomedicine-aconite
#11
Ding-Kun Zhang, Rui-Sheng Li, Xue Han, Chun-Yu Li, Zhi-Hao Zhao, Hai-Zhu Zhang, Ming Yang, Jia-Bo Wang, Xiao-He Xiao
Complex chemical composition is an important reason for restricting herbal quality evaluation. Despite the multi-components determination method significantly promoted the progress of herbal quality evaluation, however, which mainly concerned the total amount of multiple components and ignored the activity variation between each one, and did not accurately reflect the biological activity of botanical medicines. In this manuscript, we proposed a toxicity calibrated contents determination method for hyper toxic aconite, called toxic constituents index (TCI)...
2016: Frontiers in Pharmacology
https://www.readbyqxmd.com/read/27357588/the-effects-of-rheum-palmatum-l-on-the-pharmacokinetic-of-major-diterpene-alkaloids-of-aconitum-carmichaelii-debx-in-rats
#12
Yan Li, Yun-Xia Li, Meng-Jie Zhao, An Yuan, Xiao-Hong Gong, Meng-Jun Zhao, Cheng Peng
BACKGROUND AND OBJECTIVES: Aconitum carmichaelii Debx. (Fuzi) is usually compatible with Rheum palmatum L. (Dahuang) in clinic. The study is conducted to investigate the influence of Dahuang on the pharmacokinetics of Fuzi. METHODS: Twelve rats were randomly divided into two groups. Fuzi group was orally administered a single dose of 38.4 mg/kg total alkaloids from Fuzi, and Fuzi-Dahuang group was given 38.4 mg/kg total alkaloids from Fuzi and 76.8 mg/kg Dahuang anthraquinones at the same time...
June 29, 2016: European Journal of Drug Metabolism and Pharmacokinetics
https://www.readbyqxmd.com/read/27328130/a-new-c20-diterpenoid-alkaloid-from-aconitum-soongaricum-var-pubescens
#13
Lin Chen, Lianhai Shan, Wenliang Xu, Jifa Zhang, Shuai Huang, Xianli Zhou
A new denudatine-type C20-diterpenoid alkaloid, pubesine (1), along with seven known diterpenoid alkaloids, altaconitine (2), 14-benzoylaconine (3), spicatine A (4), 14-benzoylaconine-8-palmitate (5), 14-O-acetylsenbusine A (6), senbusine A (7) and 14-acetylneoline (8) were isolated from the whole plant of Aconitum soongaricum var. pubescens. Their structures were elucidated by means of extensive spectroscopic analyses (NMR and HR-ESI-MS) and comparison with data reported in the literature. All compounds were evaluated for their cytotoxicity against H460, MCF-7 and Hep G2 human cancer cell lines...
June 21, 2016: Natural Product Research
https://www.readbyqxmd.com/read/27268073/diterpenoid-alkaloids-from-the-roots-of-aconitum-brachypodum-diels
#14
Li-Guo Yang, Ying-Jie Zhang, Jia-Ying Xie, Wei-Jun Xia, Hai-Yuan Zhang, Meng-Yun Tang, Shuang-Xi Mei, Tao Cui, Jing-Kun Wang, Zhao-Yun Zhu
A new diterpenoid alkaloid, named bullatine H (1), along with 10 known diterpenoid alkaloids were isolated from the roots of Aconitum brachypodum Diels (Ranunculaceae). The structure of 1 was elucidated by analysis of its spectroscopic data. It should be noted that compound 1 is the first example with 11, 13-dioxygenated denudatine-type diterpenoid alkaloid isolated from Aconitum brachypodum.
September 2016: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/27181938/expanding-diversity-without-protecting-groups-sclareolide-to-indolosesquiterpene-alkaloid-mycoleptodiscin-a-and-analogues
#15
Karre Nagaraju, Rambabu Chegondi, Srivari Chandrasekhar
Short and scalable synthesis of the complex pentacyclic indolosesquiterpene natural product mycoleptodiscin A has been achieved from commercially available diterpenoid (+)-sclareolide in 19% overall yield. This approach allows one to prepare various analogues of mycoleptodiscin using McMurry cyclization as a key reaction with just three chromatographic purifications.
June 3, 2016: Organic Letters
https://www.readbyqxmd.com/read/27151482/an-in-silico-investigation-of-phytochemicals-as-antiviral-agents-against-dengue-fever
#16
Chelsea N Powers, William N Setzer
A virtual screening analysis of our library of phytochemical structures with dengue virus protein targets has been carried out using a molecular docking approach. A total of 2194 plant-derived secondary metabolites have been docked. This molecule set comprised of 290 alkaloids (68 indole alkaloids, 153 isoquinoline alkaloids, 5 quinoline alkaloids, 13 piperidine alkaloids, 14 steroidal alkaloids, and 37 miscellaneous alkaloids), 678 terpenoids (47 monoterpenoids, 169 sesquiterpenoids, 265 diterpenoids, 81 steroids, and 96 triterpenoids), 20 aurones, 81 chalcones, 349 flavonoids, 120 isoflavonoids, 74 lignans, 58 stilbenoids, 169 miscellaneous polyphenolic compounds, 100 coumarins, 28 xanthones, 67 quinones, and 160 miscellaneous phytochemicals...
2016: Combinatorial Chemistry & High Throughput Screening
https://www.readbyqxmd.com/read/27131574/natural-products-for-treatment-of-bone-erosive-diseases-the-effects-and-mechanisms-on-inhibiting-osteoclastogenesis-and-bone-resorption
#17
Jing An, Dingjun Hao, Qian Zhang, Bo Chen, Rui Zhang, Yi Wang, Hao Yang
Excessive bone resorption plays a central role on the development of bone erosive diseases, including osteoporosis, rheumatoid arthritis, and periodontitis. Osteoclasts, bone-resorbing multinucleated cells, are differentiated from hemopoietic progenitors of the monocyte/macrophage lineage. Regulation of osteoclast differentiation is considered an effective therapeutic target to the treatment of pathological bone loss. Natural plant-derived products, with potential therapeutic and preventive activities against bone-lytic diseases, have received increasing attention in recent years because of their whole regulative effects and specific pharmacological activities, which are more suitable for long-term use than chemically synthesized medicines...
April 28, 2016: International Immunopharmacology
https://www.readbyqxmd.com/read/27048641/qualitative-and-quantitative-assessments-of-aconiti-lateralis-radix-praeparata-using-high-performance-liquid-chromatography-coupled-with-diode-array-detection-and-hybrid-ion-trap-time-of-flight-mass-spectrometry
#18
Na Zhang, Yuelin Song, Qingqing Song, Shepo Shi, Qian Zhang, Yunfang Zhao, Jun Li, Pengfei Tu
Dual roles have been widely disclosed for Aconiti Lateralis Radix Praeparata (Chinese name: Fuzi) by acting as an effective herbal medicine accompanied with high toxicity risk and narrow therapeutic range. Aconite alkaloids, also known as diterpenoid alkaloids (DAs), have been proved to be primary therapeutic as well as toxic material basis of Fuzi. In the present study, we aim to characterize qualitative profile along with quantitative features of DAs in Fuzi, which could benefit the quality control of Fuzi as well as its safe medication in clinic...
July 2016: Journal of Chromatographic Science
https://www.readbyqxmd.com/read/26959036/eutypenoids-a-c-novel-pimarane-diterpenoids-from-the-arctic-fungus-eutypella-sp-d-1
#19
Liu-Qiang Zhang, Xiao-Chong Chen, Zhao-Qiang Chen, Gui-Min Wang, Shi-Guo Zhu, Yi-Fu Yang, Kai-Xian Chen, Xiao-Yu Liu, Yi-Ming Li
Eutypenoids A-C (1-3), pimarane diterpenoid alkaloid and two ring A rearranged pimarane diterpenoids, were isolated from the culture of Eutypella sp. D-1 obtained from high-latitude soil of the Arctic. Their structures, including absolute configurations, were authenticated on the basis of the mass spectroscopy (MS), nuclear magnetic resonance (NMR), X-ray crystallography, and electronic circular dichroism (ECD) analysis. The immunosuppressive effects of eutypenoids A-C (1-3) were studied using a ConA-induced splenocyte proliferation model, which suggested that 2 exhibited potent immunosuppressive activities...
March 7, 2016: Marine Drugs
https://www.readbyqxmd.com/read/26882669/further-studies-on-structure-cardiac-activity-relationships-of-diterpenoid-alkaloids
#20
Zhong-Tang Zhang, Xi-Xian Jian, Jia-Yu Ding, Hong-Ying Deng, Ruo-Bing Chao, Qiao-Hong Chen, Dong-Lin Chen, Feng-Peng Wang
The cardiac effect of thirty-eight diterpenoid alkaloids was evaluated on the isolated bullfrog heart model. Among them, twelve compounds exhibited appreciable cardiac activity, with compounds 3 and 35 being more active than the reference drug lanatoside. The structure-cardiac activity relationships of the diterpenoid alkaloids were summarized based on our present and previous studies [2]: i) 1α-OMe or 1α-OH, 8-OH, 14-OH, and NH (or NMe) are key structural features important for the cardiac effect of the aconitine-type C19-diterpenoid alkaloids without any esters...
December 2015: Natural Product Communications
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