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diterpenoid alkaloid

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https://www.readbyqxmd.com/read/28919359/human-intestine-and-liver-microsomal-metabolic-differences-between-c19-diester-and-monoester-diterpenoid-alkaloids-from-the-roots-of-aconitum-carmichaelii-debx
#1
Min Zhang, Chong-Sheng Peng, Xiao-Bo Li
The roots of Aconitum carmichaelii Debx. show excellent effects against rheumatism and cardiovascular diseases, but the effective compounds, C19-diester and monoester diterpenoid alkaloids (DDAs and MDAs) are toxic for their narrow therapeutic windows. It is noteworthy to investigate intestinal metabolism of these toxic compounds mainly by oral administration, because gut also express drug-metabolizing enzymes as well as liver. This study initially focused on phase I and phase II metabolism of DDAs (including aconitine, mesaconitine and hypaconitine) and MDAs (including benzoylaconine, benzoylmesaconine and benzoylhypaconine) in human intestine microsomes (HIM), with comparison of metabolism in human liver microsomes (HLM)...
September 14, 2017: Toxicology in Vitro: An International Journal Published in Association with BIBRA
https://www.readbyqxmd.com/read/28858498/a-unifying-synthesis-approach-to-the-c18-c19-and-c20-diterpenoid-alkaloids
#2
Kevin G M Kou, Svitlana Kulyk, Christopher J Marth, Jack C Lee, Nicolle A Doering, Beryl X Li, Gary M Gallego, Terry P Lebold, Richmond Sarpong
The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C18, C19, and C20 families depending on the number of contiguous carbon atoms that constitute their central framework. Herein, we detail our efforts to prepare these molecules by chemical synthesis, including a photochemical approach, and ultimately a bioinspired strategy that has resulted in the development of a unifying synthesis of one C18 (weisaconitine D), one C19 (liljestrandinine), and three C20 (cochlearenine, paniculamine, and N-ethyl-1α-hydroxy-17-veratroyldictyzine) natural products from a common intermediate...
September 20, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28820600/magnesiate-addition-ring-expansion-strategy-to-access-the-6-7-6-tricyclic-core-of-hetisine-type-c20-diterpenoid-alkaloids
#3
Jason J Pflueger, Louis C Morrill, Justine N deGruyter, Melecio A Perea, Richmond Sarpong
A synthetic strategy to access the fused 6-7-6 tricyclic core of hetisine-type C20-diterpenoid alkaloids is reported. This strategy employs a Diels-Alder cycloaddition to assemble a fused bicyclic anhydride intermediate, which is elaborated to a vinyl lactone-acetal bearing an aromatic ring in five steps. Aromatic iodination is followed by magnesium-halogen exchange with a trialkyl magnesiate species, which undergoes intramolecular cyclization. Subsequent oxidation provides the desired 6-7-6 tricyclic diketoaldehyde, with carbonyl groups at all three positions for eventual C-N bond formation and subsequent elaboration...
August 18, 2017: Organic Letters
https://www.readbyqxmd.com/read/28813032/diterpenoid-alkaloids-from-consolida-regalis-s-f-gray-subsp-paniculata-host-soo-var-paniculata
#4
Filiz Mericl, Ali H Mericli, Haridutt K Desai, Ayhan Ulubelen, S William Pelletier
Seven diterpenoid alkaloids : delcosine(1), delsoline(2), gigactonine(3), lycoctonine(4), takaosamine(5), atisine(6) and hetisinone(7) have been isolated from the aerial parts of Consolida regalis subsp. paniculata var. paniculata. The presence of compounds 1,2,5,6 and 7 in this plant has not been previously reported.
August 16, 2017: Scientia Pharmaceutica
https://www.readbyqxmd.com/read/28799605/enabling-syntheses-of-diterpenoid-alkaloids-and-related-diterpenes-by-an-oxidative-dearomatization-diels-alder-cycloaddition-strategy
#5
REVIEW
Xiao-Yu Liu, Yong Qin
Covering: 2015 to March 2017ortho-Benzoquinones generated from dearomatization of aromatic compounds are highly reactive intermediates in organic synthesis. One of their most important applications involves the participation in Diels-Alder cycloadditions, facilitating rapid access to molecular complexity. This powerful strategy has recently been utilized in the syntheses of diverse diterpenoid alkaloids and their biogenetically relevant diterpenes, which is the subject of this Highlight.
August 30, 2017: Natural Product Reports
https://www.readbyqxmd.com/read/28729705/diterpenoid-alkaloids-from-delphinium-anthriscifolium-var-majus
#6
Lian-Hai Shan, Ji-Fa Zhang, Feng Gao, Shuai Huang, Xian-Li Zhou
Extensive phytochemical investigation on the whole herbs of Delphinium anthriscifolium var. majus led to the identification of fourteen diterpenoid alkaloids, including three new C20-diterpenoid alkaloids (anthriscifolsines A-C, 1-3), six new C19-diterpenoid alkaloids (anthriscifolrines A-F, 4-9), and five know compounds (10-14). Among them, anthriscifolsine A represents a novel C20-diterpenoid alkaloid characterized by a seco C-ring. The structures of the isolated compounds were elucidated by extensive spectroscopic methods, including HR-ESI-MS, X-ray, and 1D and 2D NMR experiments...
July 20, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28718960/chemical-uplc-esi-ms-ms-profiling-of-aconitum-alkaloids-and-their-metabolites-in-rat-plasma-and-urine-after-oral-administration-of-aconitum-carmichaelii-debx-root-extract
#7
Mingjie Zhang, Manman Wang, Jiajia Liang, Yongqing Wen, Zhili Xiong
In this paper, an ultra high performance liquid chromatography tandem mass spectrometric (UPLC-ESI-MS/MS) method in positive ion mode was established to systematically identify and to compare the major aconitum alkaloids and their metabolites in rat plasma and urine after oral administration of Fuzi extract. A total twenty-nine components including twenty-five C19 -diterpenoid alkaloids and four C20 -diterpenoid alkaloids were identified in Fuzi extract. Thirteen of the parent components and five metabolites were detected in rat plasma and sixteen parent compounds and six metabolites in urine...
July 18, 2017: Biomedical Chromatography: BMC
https://www.readbyqxmd.com/read/28629532/hypaconitine-inhibits-tgf-%C3%AE-1-induced-epithelial-mesenchymal-transition-and-suppresses-adhesion-migration-and-invasion-of-lung-cancer-a549-cells
#8
Hai-Tao Feng, Wen-Wen Zhao, Jin-Jian Lu, Yi-Tao Wang, Xiu-Ping Chen
Epithelial-mesenchymal transition (EMT) has been implicated in tumor invasion and metastasis and provides novel strategies for cancer therapy. Hypaconitine (HpA), a diester-diterpenoid alkaloid isolated from the root of the Aconitum species, exhibits anti-inflammatory, analgesic, and especially, cardiotoxic activities. Here, we reported the anti-metastatic potentials of HpA in transforming growth factor-β1 (TGF-β1)-induced EMT in lung cancer A549 cells. The cytotoxic effect of HpA was determined by MTT assay...
June 2017: Chinese Journal of Natural Medicines
https://www.readbyqxmd.com/read/28614697/navicularines-a-c-new-diterpenoid-alkaloids-from-aconitum-naviculare-and-their-cytotoxic-activities
#9
Jiang-Bo He, Jie Luan, Xiao-Man Lv, Dan-Yun Rui, Jian Tao, Bo Wang, Yan-Feng Niu, Hong-Ping Ju
Three new bisditerpenoid alkaloids, navicularines A-C (1-3), and three known ones (4-6), were isolated from the ground parts of Aconitum naviculare. Their structures were elucidated by spectroscopic methods. All the new compounds were tested against five cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480). It was found that navicularine B exhibited certain cytotoxic activities in vitro, with IC50 values of 13.50, 18.52, 17.22, 11.18, and 16.36μM, respectively.
July 2017: Fitoterapia
https://www.readbyqxmd.com/read/28590124/terpenoids-from-euphorbia-soongarica-and-their-multidrug-resistance-reversal-activity
#10
Jie Gao, Haji A Aisa
Ten new terpenoids, including five diterpenoids (1-5), three nortriterpenoids (6-8), and two triterpenoids (9, 10), and 15 known terpenoids (11-25) were isolated from an acetone extract of Euphorbia soongarica. Sooneuphoramine (1) is the first example of a euphoractine B-type diterpenoid alkaloid, while sooneuphanones A-C (6-8) are rare nortriterpenoids from the Euphorbia genus. The isolated terpenoids were tested for their cytotoxicity and multidrug resistance (MDR) reversal activity, 10 of which showed moderate cytotoxicity against the KB and KBv200 cell lines, while 11 compounds exhibited P-gp modulating potential...
June 23, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28569094/c18-diterpenoid-alkaloids-from-delphinium-anthriscifolium-var-majus
#11
Lian-Hai Shan, Ji-Fa Zhang, Feng Gao, Shuai Huang, Xian-Li Zhou
Five new C18-diterpenoid alkaloids, anthriscifoltines C-G (1-5), along with four known diterpenoid alkaloids anthriscifolcines C-F (6-9), were isolated from the extract of Delphinium anthriscifolium var. majus. Their structures were elucidated by extensive spectroscopic analyses (including 1D-, 2D-NMR, and HR-ESI-MS). Compounds 1-5 were also evaluated for their cytotoxic activity against MCF-7, HepG2, and H460 human cancer cell lines.
June 1, 2017: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/28457693/antioxidant-and-anticholinesterase-potential-of-diterpenoid-alkaloids-from-aconitum-heterophyllum
#12
Hanif Ahmad, Shujaat Ahmad, Syed Adnan Ali Shah, Abdul Latif, Mumtaz Ali, Farman Ali Khan, Muhammad Nawaz Tahir, Farzana Shaheen, Abdul Wadood, Manzoor Ahmad
Extensive chromatographic separations performed on the basic (pH=8-10) chloroform soluble fraction of Aconitum heterophyllum resulted in the isolation of three new diterpenoid alkaloids, 6β-Methoxy, 9β-dihydroxylheteratisine (1), 1α,11,13β-trihydroxylhetisine (2), 6,15β-dihydroxylhetisine (3), and the known compounds iso-atisine (4), heteratisine (5), hetisinone (6), 19-epi-isoatisine (7), and atidine (8). Structures of the isolated compounds were established by means of mass and NMR spectroscopy as well as single crystal X-ray crystallography...
July 1, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28453270/vitepyrroloids-a-d-2-cyanopyrrole-containing-labdane-diterpenoid-alkaloids-from-the-leaves-of-vitex-trifolia
#13
Pan Luo, Wenjuan Xia, Susan L Morris-Natschke, Kuo-Hsiung Lee, Yu Zhao, Qiong Gu, Jun Xu
Vitepyrroloids A-D (1-4), four new 2-cyano-substituted pyrrole-ring-containing labdane diterpenoids, were isolated from the leaves of Vitex trifolia. Their structures were elucidated based on spectroscopic data analysis. The absolute configuration of compound 1 was determined by X-ray diffraction. Compounds 1-4 are unprecedented labdane diterpenoids featuring a 2-cyano-substituted pyrrole ring. Compound 1 showed cytotoxic activity against a human nasopharyngeal carcinoma cell line (CNE1) with an IC50 value of 8...
May 26, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28387961/chemical-profiling-combined-with-omics-technologies-cp-omics-a-strategy-to-understand-the-compatibility-mechanisms-and-simplify-herb-formulas-in-traditional-chinese-medicines
#14
Tengfei Xu, Zifeng Pi, Shu Liu, Fengrui Song, Zhiqiang Liu
INTRODUCTION: The compatibility mechanisms of formulas in traditional Chinese medicine (TCM) are indistinct. In order to better understand the compatibility mechanisms and the quality control of the formulas, it is necessary to simplify formulas in TCM research. OBJECTIVE: Developing a novel method by multi-analysing the contents of different compounds in formula and inferred simplified formula simultaneously. METHODOLOGY: Chemical profiling combined with "omics" technologies (CP-omics) was employed in the present study...
April 7, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/28276773/two-new-c19-diterpenoid-alkaloids-from-aconitum-tsaii
#15
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.
May 2017: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/28276004/hydroxylation-metabolisms-of-crassicauline-a-in-rats-under-toxic-dose
#16
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
#17
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
#18
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
#19
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
#20
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
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