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diterpenoid alkaloid

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https://www.readbyqxmd.com/read/28276773/two-new-c19-diterpenoid-alkaloids-from-aconitum-tsaii
#1
Gui-Qiong Li, Li-Mei Zhang, Da-Ke Zhao, Yan-Ping Chen, Yong Shen
Two new C19-diterpenoid alkaloids, 14-benzoylliljestrandisine (1) and 14-anisoylliljestrandisine (2), were isolated from the roots of Aconitum tsaii. Their structures were elucidated by different spectroscopic (IR, UV, 1D and 2D NMR) and mass-spectrometric techniques.
September 22, 2016: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/28276004/hydroxylation-metabolisms-of-crassicauline-a-in-rats-under-toxic-dose
#2
Xue Fan, Shan-Shan Yin, Xue-Jing Li, Kui Yang, Liang Xu, Ke Lan
BACKGROUND AND OBJECTIVES: Crassicauline A, a C19 diterpenoid alkaloid in Aconitum herbs, is an analgesic drug clinically used in China. The in vivo metabolism of crassicauline A is poorly understood, while potential bioactivation is anticipated via hydroxylation metabolism. This work, therefore, aimed to investigate the in vivo hydroxylation metabolism of crassicauline A in rats. METHODS: Using a de novo developed and validated UPLC-MS/MS method, excretion studies in rats were carried out to investigate the recoveries of crassicauline A and its hydroxylated metabolites in urine and feces...
March 8, 2017: European Journal of Drug Metabolism and Pharmacokinetics
https://www.readbyqxmd.com/read/28264454/an-investigation-on-the-quantitative-structure-activity-relationships-of-the-anti-inflammatory-activity-of-diterpenoid-alkaloids
#3
Xiao Li, Ning Li, Zhenyu Sui, Kaishun Bi, Zuojing Li
Diterpenoid alkaloids are extracted from plants. These compounds have broad biological activities, including effects on the cardiovascular system, anti-inflammatory and analgesic actions, and anti-tumor activity. The anti-inflammatory activity was determined by carrageenan-induced rat paw edema and experimental trauma in rats. The number of studies focused on the determination, quantitation and pharmacological properties of these alkaloids has increased dramatically during the past few years. In this work we built a dataset composed of 15 diterpenoid alkaloid compounds with diverse structures, of which 11 compounds were included in the training set and the remaining compounds were included in the test set...
February 27, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28259252/a-new-diterpenoid-alkaloid-isolated-from-delphinium-caeruleum
#4
Chao-Zhan Lin, Zhu-Jie Liu, Zeren-Dawa Bairi, Chen-Chen Zhu
The present study was designed to determine the chemical constituents of Delphinium caeruleum Jacq. ex Camb.. The chemical constituents were isolated and purified by column chromatography with silica gel, ODS, and Sephadex LH-20. Their structures were elucidated by IR, MS, and NMR. Ten compounds were obtained and identified as caerudelphinine A (1), lycoctonine (2), talitine B (3), talitine A (4), talitine C (5), tatsienine-V (6), d-magnoflorine (7), 2-trimethyl-ammonio-3-(3-indolyl) propionate (8), vakhmatine (9), and delatisine (10)...
January 2017: Chinese Journal of Natural Medicines
https://www.readbyqxmd.com/read/28208826/anticancer-activities-of-c18-c19-c20-and-bis-diterpenoid-alkaloids-derived-from-genus-aconitum
#5
REVIEW
Meng-Yue Ren, Qing-Tian Yu, Chun-Yu Shi, Jia-Bo Luo
Cancer is one of the most common lethal diseases, and natural products have been extensively studied as anticancer agents considering their availability, low toxicity, and economic affordability. Plants belonging to the genus Aconitum have been widely used medically in many Asian countries since ancient times. These plants have been proven effective for treating several types of cancer, such as lung, stomach, and liver cancers. The main effective components of Aconitum plants are diterpenoid alkaloids-which are divided into C18-, C19-, C20-, and bis-diterpenoid alkaloids-are reportedly some of the most promising, naturally abundant compounds for treating cancer...
February 13, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28074665/diterpenoid-alkaloids-from-the-root-of-aconitum-sinchiangense-w-t-wang-with-their-antitumor-and-antibacterial-activities
#6
Xiaoxia Liang, Lan Chen, Lei Song, Wenbo Fei, Min He, Changliang He, Zhongqiong Yin
A phytochemical study of the root barks of Aconitum sinchiangense W. T. Wang, a traditional Chinese herb medicine, led to the isolation of 15 diterpenoid alkaloids, including one new C19-diterpenoid alkaloid, sinchiangensine A (1), whose structure was determined by spectral methods including 2D NMR. Additionally, sinchiangensine A and its known analogue 3 were first reported as potential antitumor and antibacterial diterpenoid alkaloids, which showed significant antitumor activities against tumour cells (HL-60, A-549, SMCC-7721, MCF-7 and SW480), with IC50 comparable to cisplatin, and significant antibacterial activities against Staphylococcus aureus ATCC-25923 with MIC value of 0...
January 11, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28033733/isolation-crystal-structure-determination-and-cholinesterase-inhibitory-potential-of-isotalatizidine-hydrate-from-delphinium-denudatum
#7
Hanif Ahmad, Shujaat Ahmad, Ezzat Khan, Adnan Shahzad, Mumtaz Ali, Muhammad Nawaz Tahir, Farzana Shaheen, Manzoor Ahmad
CONTEXT: Delphinium denudatum Wall (Ranunculaceae) is a rich source of diterpenoid alkaloids and is widely used for the treatment of various neurological disorders such as epilepsy, sciatica and Alzheimer's disease. OBJECTIVE: The present study describes crystal structure determination and cholinesterase inhibitory potential of isotalatazidine hydrate isolated from the aerial part of Delphinium denudatum. MATERIALS AND METHODS: Phytochemical investigation of Delphinium denudatum resulted in the isolation of isotalatazidine hydrate in crystalline form...
December 2017: Pharmaceutical Biology
https://www.readbyqxmd.com/read/27989510/concurrent-bullatine-a-enhances-morphine-antinociception-and-inhibits-morphine-antinociceptive-tolerance-by-indirect-activation-of-spinal-%C3%AE%C2%BA-opioid-receptors
#8
Qian Huang, Ming-Li Sun, Yuan Chen, Xin-Yan Li, Yong-Xiang Wang
ETHNOPHARMACOLOGICAL RELEVANCE: Bullatine A, a C20-diterpenoid alkaloid and one of the major effective ingredients in Aconiti brachypodi Radix (Xue-shang-yi-zhi-hao), can block pain hypersensitivity in a variety of rodent models through expression of spinal microglial dynorphin A. AIM OF THE STUDY: To assess the interaction between bullatine A and morphine on antinociception in acute nociception and pain hypersensitivity states, with the exogenous synthetic dynorphin A as a comparison MATERIALS AND METHODS: Spinal nerve ligation-induced neuropathic rats and naïve mice were used for assessing the acute and chronic interactions of bullatine A/dynorphin A with morphine...
January 20, 2017: Journal of Ethnopharmacology
https://www.readbyqxmd.com/read/27975956/four-new-diterpenoid-alkaloids-from-aconitum-japonicum
#9
K Wada, K Takeda, M Haraguchi, Y Abe, N Kuwahara, S Suzuki, A Terui, T Masaka, N Munakata, M Uchida, M Nunokawa, H Yamashita, M Goto, K H Lee
No abstract text is available yet for this article.
December 2016: Planta Medica
https://www.readbyqxmd.com/read/27936494/five-new-c19-diterpenoid-alkaloids-from-delphinium-tianshanicum-w-t-wang
#10
By Ji-Fa Zhang, Lian-Hai Shan, Feng Gao, Shuai Huang, Xian-Li Zhou
Five new diterpenoid alkaloids tianshanitine A-E (1-5), along with ten known compounds (6-15), were isolated from the ethanolic extracts of the whole plant of Delphinium tianshanicum W. T. Wang. Their structures were determined based on extensive spectroscopic analyses, including 1D, 2D NMR, HRESIMS, and the structure of tianshanitine C (3) was confirmed by X-ray diffraction analysis. Tianshanitine A (1) is the first example of natural diterpenoid alkaloid containing a benzoyl group at C-1 position. Tianshanitine B (2) is a rare natural diterpenoid alkaloid including a hydroxyl group at C-16 position...
December 9, 2016: Chemistry & Biodiversity
https://www.readbyqxmd.com/read/27860043/synthesis-of-atisine-ajaconine-denudatine-and-hetidine-diterpenoid-alkaloids-by-a-bioinspired-approach
#11
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.
December 12, 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
#12
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
#13
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).
December 2, 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
#14
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
#15
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.
January 2017: Natural Product Research
https://www.readbyqxmd.com/read/27626453/the-search-for-herbal-antibiotics-an-in-silico-investigation-of-antibacterial-phytochemicals
#16
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
#17
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
#18
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
#19
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
#20
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...
January 2017: Planta Medica
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