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diterpenoid alkaloid

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https://www.readbyqxmd.com/read/28208826/anticancer-activities-of-c18-c19-c20-and-bis-diterpenoid-alkaloids-derived-from-genus-aconitum
#1
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
#2
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
#3
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
#4
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
#5
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
#6
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
#7
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
#8
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
#9
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
#10
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
#11
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
#12
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
#13
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
#14
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
#15
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
#16
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
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
#17
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
#18
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
#19
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...
March 2017: Natural Product Research
https://www.readbyqxmd.com/read/27268073/diterpenoid-alkaloids-from-the-roots-of-aconitum-brachypodum-diels
#20
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
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