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diterpenoid alkaloid

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https://www.readbyqxmd.com/read/29148797/nigegladines-a-c-three-thymoquinone-dimers-from-nigella-glandulifera
#1
Jie Tian, Chao Han, Wen-Hua Guo, Yong Yin, Xiao-Bing Wang, Hong-Bin Sun, He-Quan Yao, Yong Yang, Chen Wang, Chang Liu, Ming-Hua Yang, Ling-Yi Kong
Nigegladines A-C (1-3), three thymoquinone dimers, were isolated from the seeds of Nigella glandulifera. Racemic 1 possesses a unique tricyclo[5.4.0.1(2,6)]dodecane carbon skeleton, and compounds 2 and 3 are two unusual diterpenoid alkaloids with indole cores. Their structures were determined by extensive spectroscopic analyses, and that of 1 was confirmed by single-crystal X-ray diffraction. Both (+)-1 and (-)-1 exhibited significant protective effects against hypoxia/reoxygenation-induced H9c2 myocardial cell injury...
November 17, 2017: Organic Letters
https://www.readbyqxmd.com/read/29133056/therapeutic-potential-of-songorine-a-diterpenoid-alkaloid-of-the-genus-aconitum
#2
REVIEW
Haroon Khan, Seyed Mohammad Nabavi, Antoni Sureda, Nikolay Mehterov, Diana Gulei, Ioana Berindan-Neagoe, Hiroaki Taniguchi, Atanas G Atanasov
Alkaloids are well-studied secondary metabolites, with recent preclinical studies evidencing that many of them exhibit anti-cancer, anti-depressant, anti-nociceptive, anti-inflammatory, anti-pyretic, anti-platelet, anti-oxidant, and anti-bacterial properties. Aconitum is a genus rich of diverse alkaloids. More than 450 alkaloids have been identified in a variety of species. Songorine is a C20 diterpenoid alkaloid and 12-keto analog of napelline, isolated from Aconitum soongaricum and was associated with a heterogeneous panel of biological functions...
November 10, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29115599/aconitine-induces-apoptosis-in-h9c2-cardiac-cells-via-mitochondria%C3%A2-mediated-pathway
#3
Xiangting Gao, Xincai Zhang, Jun Hu, Xuehua Xu, Yuanyi Zuo, Yun Wang, Jingfeng Ding, Hongfei Xu, Shaohua Zhu
Aconitine, a diterpenoid alkaloids derived from Aconitum plants, is widely employed to treat various diseases. The aim of the present study was to investigate the apoptotic effect of aconitine in H9c2 cardiac cells. H9c2 cell apoptosis induced by aconitine was detected by a Cell Counting kit‑8 assay, DAPI staining, Annexin V‑FITC/propidium iodide double staining and western blotting. The effects of aconitine on reactive oxygen species levels and mitochondrial membrane potential were confirmed by fluorescence microscopy and flow cytometry...
October 26, 2017: Molecular Medicine Reports
https://www.readbyqxmd.com/read/29104243/diverse-secondary-metabolites-from-the-marine-derived-fungus-dichotomomyces-cejpii-f31-1
#4
Yan-Xiu Chen, Meng-Yang Xu, Hou-Jin Li, Kun-Jiao Zeng, Wen-Zhe Ma, Guo-Bao Tian, Jun Xu, De-Po Yang, Wen-Jian Lan
By adding l-tryptophan and l-phenylalanine to GPY medium, twenty-eight compounds, including amides, polyketides, a sesquiterpenoid, a diterpenoid, a meroterpenoid, diketopiperazines, β-carbolines, fumiquinazolines, and indole alkaloids, were discovered from the marine-derived fungus Dichotomomyces cejpii F31-1, demonstrating the tremendous biosynthetic potential of this fungal strain. Among these compounds, four amides dichotomocejs A-D (1-4), one polyketide dichocetide A (5), and two diketopiperazines dichocerazines A-B (15 and 16) are new...
November 1, 2017: Marine Drugs
https://www.readbyqxmd.com/read/29052027/four-new-diterpenoid-alkaloids-from-aconitum-japonicum-subsp-subcuneatum
#5
Hiroshi Yamashita, Keiko Takeda, Machiko Haraguchi, Yuki Abe, Natsumi Kuwahara, Shota Suzuki, Ayaka Terui, Takumi Masaka, Naoko Munakata, Mariko Uchida, Masashi Nunokawa, Kyousuke Kaneda, Masuo Goto, Kuo-Hsiung Lee, Koji Wada
Diterpenoid alkaloids with remarkable chemical properties and biological activities are frequently found in plants of the genera Aconitum, Delphinium, and Garrya. Accordingly, several diterpenoid alkaloid constituents of Aconitum and Delphinium plants as well as their derivatives exhibited cytotoxic activity against lung, prostate, nasopharyngeal, and vincristine-resistant nasopharyngeal cancer cell lines. Four new C19-diterpenoid alkaloids, 14-anisoyllasianine (1), 14-anisoyl-N-deethylaconine (2), N-deethylaljesaconitine A (3), and N-deethylnevadensine (4), together with 17 known C19- and C20-diterpenoid alkaloids, were isolated in a phytochemical investigation of rhizoma of Aconitum japonicum THUNB...
October 19, 2017: Journal of Natural Medicines
https://www.readbyqxmd.com/read/29039205/synthesis-of-cardiopetaline-via-a-wagner-meerwein-rearrangement-without-preactivation-of-the-pivotal-hydroxy-group
#6
Yoshitake Nishiyama, Satoshi Yokoshima, Tohru Fukuyama
A synthesis of cardiopetaline has been accomplished via a Wagner-Meerwein rearrangement of a diol having the denudatine skeleton. The Wagner-Meerwein rearrangement could be facilitated simply by heating the diol with p-toluenesulfonic acid in pivalic acid, without preactivating the pivotal hydroxy group. This strategy does not require differentiation of several hydroxy groups in the substrate for the Wagner-Meerwein rearrangement and could be applied to the synthesis of more highly oxygenated aconitine-type diterpenoid alkaloids...
October 17, 2017: Organic Letters
https://www.readbyqxmd.com/read/28985284/determination-of-five-aminoalcohol-diterpenoid-alkaloids-in-the-lateral-root-of-aconitum-carmichaeli-by-hplc-elsd-with-spe
#7
Dan Huang, Xinqing Zhao, Xiuxiu Liu, Ruobing Chao
A convenient and accurate high-performance liquid chromatography coupled with evaporative light scattering detection (HPLC-ELSD) method using solid phase extraction (SPE) was established for quantification of five aminoalcohol-diterpenoid alkaloids (ADAs), including mesaconine, aconine, hypaconine, fuziline and neoline, in the lateral roots of Aconitum carmichaeli (Fuzi) for the first time. The Fuzi extractive was purified using strong cation-exchange SPE. The chromatographic separation was performed on a Gemini C18 column (150 × 4...
July 14, 2017: Journal of Chromatographic Science
https://www.readbyqxmd.com/read/28970156/leishmanicidal-activity-of-the-root-bark-of-erythrophleum-ivorense-fabaceae-and-identification-of-some-of-its-compounds-by-ultra-performance-liquid-chromatography-quadrupole-time-of-flight-mass-spectrometry-uplc-qtof-ms-ms
#8
Francis A Armah, Isaac K Amponsah, Abraham Y Mensah, Rita A Dickson, Paul A Steenkamp, Ntakadzeni E Madala, Christian K Adokoh
ETHNOPHARMACOLOGICAL RELEVANCE: Leishmaniasis is one of the neglected tropical disease caused by a protozoan of the genus Leishmania transmitted by sandflies. High cost and lack of oral formulation of existing drugs, rapid developments of resistance by the parasite coupled with serious side effects require new treatments to augment or replace currently available therapies. The major merits of herbal medicine seem to demonstrate perceived efficacy, low incidence of serious adverse effects and low cost...
September 29, 2017: Journal of Ethnopharmacology
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
#9
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
#10
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
#11
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
#12
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
#13
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
#14
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
#15
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
#16
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
#17
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
#18
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
#19
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
#20
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
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