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diterpenoid alkaloid

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https://www.readbyqxmd.com/read/29785743/four-new-diterpenoid-alkaloids-from-the-roots-of-aconitum-carmichaelii
#1
Yu Li, Feng Gao, Ji-Fa Zhang, Xian-Li Zhou
Aconitum carmichaelii, belonging to the Ranunculaceae family, is mainly distributed and cultivated in southwestern China. Its parent and lateral roots, two well-known traditional medicinal materials, are commonly called as "Chuanwu" and "Fuzi" in China, respectively. A. carmichaelii is widely used for the treatment of cadianeuria, neuralgia, and rheumatalgia in Chinese medicine. According to the pharmacology studies, diterpenoid alkaloids accounted for the major effects and toxicity of this plant, such as hypaconitine, mesaconitine, aconitine...
May 21, 2018: Chemistry & Biodiversity
https://www.readbyqxmd.com/read/29783906/bulleyaconitine-a-attenuates-hyperexcitability-of-dorsal-root-ganglion-neurons-induced-by-spared-nerve-injury-the-role-of-preferably-blocking-nav1-7-and-nav1-3-channels
#2
Man-Xiu Xie, Jie Yang, Rui-Ping Pang, Wei-An Zeng, Han-Dong Ouyang, Yan-Qing Liu, Xian-Guo Liu
Background Oral administration of Bulleyaconitine A, an extracted diterpenoid alkaloid from Aconitum bulleyanum plants, is effective for treating chronic pain in rats and in human patients, but the underlying mechanisms are poorly understood. Results As the hyperexcitability of dorsal root ganglion neurons resulting from the upregulation of voltage-gated sodium (Nav) channels has been proved critical for development of chronic pain, we tested the effects of Bulleyaconitine A on Nav channels in rat spared nerve injury model of neuropathic pain...
January 2018: Molecular Pain
https://www.readbyqxmd.com/read/29781312/diterpenoid-alkaloids-from-delphinium-naviculare-var-lasiocarpum-with-their-antifeedant-activity-on-spodoptera-exigua
#3
Lianhai Shan, Lin Chen, Feng Gao, Xianli Zhou
A new lycoctonine diterpenoid alkaloid navicularine, along with eighteen known diterpenoid alkaloids, were isolated from the whole plant of Delphinium naviculare var. lasiocarpum. Their structures were elucidated on the base of extensive spectroscopic analysis (HR-ESI-MS and NMR) and comparison with data reported in the literature. Most of alkaloids were tested for their antifeedant activity against larvae of Spodoptera exigua (Hübner). The compound shawurensine showed considerably potent antifeedant activity (EC50 = 0...
May 21, 2018: Natural Product Research
https://www.readbyqxmd.com/read/29774741/synthesis-of-vitepyrroloid-a-and-vitepyrroloid-b-by-late-stage-ni-catalyzed-c-sp2-c-sp3-cross-electrophile-coupling
#4
Martina Menger, Dieter Lentz, Mathias Christmann
A concise and scalable five-step synthesis of vitepyrroloids A and B, two cytotoxic labdane diterpenoid alkaloids from Vitex trifolia, is presented. The presented approach features a Ni-catalyzed cross-electrophile coupling between a (+)-sclareolide-derived alkyl iodide and 3-bromo-2-cyanopyrrole.
May 18, 2018: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29758520/probing-the-transcriptome-of-aconitum-carmichaelii-reveals-the-candidate-genes-associated-with-the-biosynthesis-of-the-toxic-aconitine-type-c-19-diterpenoid-alkaloids
#5
Dake Zhao, Yong Shen, Yana Shi, Xingqiao Shi, Qin Qiao, Shuhui Zi, Erqiang Zhao, Diqiu Yu, Edward J Kennelly
Aconitum carmichaelii has long been used as a traditional Chinese medicine, and its processed lateral roots are known commonly as fuzi. Aconitine-type C19 -diterpenoid alkaloids accumulating in the lateral roots are some of the main toxicants of this species, yet their biosynthesis remains largely unresolved. As a first step towards understanding the biosynthesis of aconitine-type C19 -diterpenoid alkaloids, we performed de novo transcriptome assembly and analysis of rootstocks and leaf tissues of Aconitum carmichaelii by next-generation sequencing...
May 11, 2018: Phytochemistry
https://www.readbyqxmd.com/read/29757005/four-new-c-20-diterpenoid-alkaloids-from-aconitum-rotundifolium
#6
Ji-Fa Zhang, Yu Li, Feng Gao, Lian-Hai Shan, Xian-Li Zhou
Four new C20 -diterpenoid alkaloids, rotundifosines D-G (1-4), along with eight known ones (5-12) were isolated from the whole plant of Aconitum rotundifolium Kar. & Kir. The structures of the compounds were elucidated on the basis of spectroscopic analyses, including HR-ESI-MS and 1D, 2D NMR. Rotundifosine F (3) is a rare C20 -diterpenoid alkaloid with quaternary ammonium salt. Alkaloids 1-4, 5, 6, 9, and 12 were evaluated for cytotoxicity against MCF-7, HCT-116 and HepG2 human cancer cell lines.
May 14, 2018: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/29611891/a-unified-approach-for-the-assembly-of-atisine-and-hetidine-type-diterpenoid-alkaloids-total-syntheses-of-azitine-and-the-proposed-structure-of-navirine-c
#7
Dawei Ma, Jie Liu
A tetracyclic dinitrile was synthesized in 12 steps from cyclohex-2-en-1-one by using a chelation-triggered conjugate addition to g-hydroxy a,b-unsaturated nitrile and oxidative-dearomatization/Diels-Alder cycloaddition as the key steps. The first total synthesis of azitine (in 17 steps) was achieved through a simple reductive cyclization of this intermediate and subsequent transformations, while total synthesis of the proposed structure of navirine C (in 19 steps) was accomplished via a HAT reaction of the tetracyclic dinitrile, Pd/C-catalyzed reductive cyclization and subsequent functional group manipulation...
April 3, 2018: Angewandte Chemie
https://www.readbyqxmd.com/read/29600653/-content-determination-of-four-diester-diterpenoid-alkaloids-in-leaves-of-aconitum-kusnezoffii-by-hplc
#8
Ke Zan, Ci-Ren Wangjie, Jing Lu, Li-Nong Guo, Jian Zheng, Shuang-Cheng Ma
This present study is to develop an HPLC method for simultaneous determination of four diester diterpenoid alkaloids, beiwutine, mesaconitine, hypaconitine and aconitine in the leaves of Aconitum kusnezoffii, so as to provide evidence of the quality control of this herb. The four constituents were measured on a Waters XBridge CC₁₈ column(4.6 mmχ250 mm, 5 μm). The mobile phase was acetonitrile-40 mmol·L⁻¹ ammonium acetate solution(adjusted pH to 10.5 with ammonia solution)(33:67) with isocratic elution at a flow rate of 1...
February 2018: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/29569945/four-new-c-19-diterpenoid-alkaloids-from-the-roots-of-aconitum-ouvrardianum
#9
Wang-Yan Liu, Dan He, Da-Ke Zhao, Yan-Ping Chen, Yong Shen
Four new C19 -diterpenoid alkaloids, 3-dehydroxyl-lipoindaconitine (1), 8-dehydroxyl-bikhaconine (2), 19R-acetonyl-talatisamine (3), and 16-hydroxyl-vilmorisine (4), were isolated from the roots of Aconitum ouvrardianum. Their structures were elucidated by spectral analyses, including ESI-MS, HR-ESI-MS, IR, UV, 1D and 2D NMR.
March 23, 2018: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/29552850/-effects-of-different-decocting-methods-on-quality-of-mahuang-xixin-fuzi-decoction
#10
Li-Li Qiu, Can Li, Shan-Shan Fan, Xu Han, Yong Yang, Rong Rong
To compare the quality difference between Mahuang Xixin Fuzi decoction(MXF) prepared by traditional decocting method and that prepared by two commonly used decocting methods, and explore the scientific nature of the traditional decocting method. By taking effect-toxic components in MXF as the research object, this article investigated these three different decocting methods from the quantitative determination of effect-toxic components in MXF. By using multivariate statistical analysis methods, three characteristic constituents were identified as kakoul, mesaconitine (MA) and hypaconitine (HA) respectively...
January 2018: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/29484902/two-new-bis-c-20-diterpenoid-alkaloids-with-anti-inflammation-activity-from-aconitum-bulleyanum
#11
Xiao-Yan Duan, Da-Ke Zhao, Yong Shen
Two new bis-C20 -diterpenoid alkaloids, bulleyanines A and B (1 and 2), were isolated from Aconitum bulleyanum. Their structures were elucidated by comprehensive spectroscopic analyses including UV, IR, MS, 1D and 2D NMR. Biological activity tests indicated that compound 1 exhibited significant inhibitory activity against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 macrophages with the inhibition rate of 74.60% (40 μmol/L), while positive control dexamethasone gave 78.70% inhibition at 100 μg/ml...
February 27, 2018: Journal of Asian Natural Products Research
https://www.readbyqxmd.com/read/29430945/diterpenoid-alkaloids-from-aconitum-brevicalcaratum-as-autophagy-inducers
#12
Haiyue Jiang, Shuai Huang, Feng Gao, Yongqi Zhen, Chunying Li, Xianli Zhou
A new C19 diterpenoid alkaloid, brevicanine (1) and six known ones (2-7) were isolated from Aconitum brevicalcaratum (Finet et Gagnep.) Diels. Their structures were elucidated on the basis of extensive spectroscopic analyses. The cytotoxicity of those compounds was investigated against HCT116 human cancer cell line, which showed none of them possessing considerable anti-proliferative activities. To evaluate the autophagy effect of compounds 1-7, Western blot was used to detect the expression of autophagic marker by stimulating human cancer HCT116 cells...
February 12, 2018: Natural Product Research
https://www.readbyqxmd.com/read/29404034/effect-of-processing-on-the-alkaloids-in-aconitum-tubers-by-hplc-tof-ms
#13
Min Liu, Yan Cao, Diya Lv, Wen Zhang, Zhenyu Zhu, Hai Zhang, Yifeng Chai
According to the Chinese Pharmacopoeia 2015, only processed Aconitum tubers can be clinically applied, and the effect of processing is unclear. This research aimed to explore the effect of processing on cardiac efficacy of alkaloids in Aconitum tubers. First, the chemical ingredients in unprocessed and processed Aconitum tubers were identified and compared by using high performance liquid chromatography time-of-flight mass spectrometry (HPLC-TOF/MS) and multivariate pattern recognition methods. Then the representative alkaloids in Aconitum tubers, aconitine, benzoylaconine, and aconine, which belong to diester-diterpenoid alkaloids, monoester-diterpenoid alkaloids, and amine-diterpenoid alkaloids, respectively, were selected for further validation of attenuated mechanism...
June 2017: Journal of Pharmaceutical Analysis
https://www.readbyqxmd.com/read/29382158/rapid-characterization-and-identification-of-non-diterpenoid-constituents-in-tinospora-sinensis-by-hplc-ltq-orbitrap-ms-n
#14
Qi-Shu Jiao, Lu-Lu Xu, Jia-Yu Zhang, Zi-Jian Wang, Yan-Yan Jiang, Bin Liu
Tinospora sinensis , a kind of Chinese folk medicine, has functions of harmonizing qi and blood, dredging the channels and collaterals, calming and soothing the nerves. In the present study, a method based on high-performance liquid chromatography coupled with linear ion trap-Orbitrap mass spectrometry (HPLC-LTQ-Orbitrap) was developed for the systematical characterization of the non-diterpenoid constituents which possessed remarkable biological activities in T . sinensis, like anti-tumor, anti-inflammatory, hypoglycemic activity and immunomodulatory activity...
January 29, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29375725/four-new-c-19-diterpenoid-alkaloids-from-delphinium-elatum
#15
Hiroshi Yamashita, Megumi Katoh, Akane Kokubun, Ayano Uchimura, Sakina Mikami, Ayana Takeuchi, Kyousuke Kaneda, Yuji Suzuki, Megumi Mizukami, 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 C19 -diterpenoid alkaloid components from Delphinium elatum cv. Pacific Giant, as well as their derivatives, exhibited cytotoxic activity against lung, prostate, nasopharyngeal, and vincristine-resistant nasopharyngeal cancer cell lines. Four new C19 -diterpenoid alkaloids, elapacigine ( 1 ), N -deethyl- N -formylpaciline ( 2 ), N -deethyl- N -formylpacinine ( 3 ), and N -formyl-4,19-secoyunnadelphinine ( 4 ), together with 11 known C19 -diterpenoid alkaloids were isolated in a phytochemical investigation on the seeds of D...
April 2018: Phytochemistry Letters
https://www.readbyqxmd.com/read/29335190/phytochemistry-and-pharmacology-of-the-genus-leonurus-the-herb-to-benefit-the-mothers-and-more
#16
REVIEW
Rui-Han Zhang, Zhi-Ke Liu, Da-Song Yang, Xing-Jie Zhang, Han-Dong Sun, Wei-Lie Xiao
Plants belonging to the genus Leonurus, also named motherwort, are traditionally used for anti-gynecological disorder in East Asia, and for sedative in Europe. Chemical investigation of the genus Leonurus not only enriched the natural products library, but also enlarged the pharmacological application of this traditional herb. In this review, we systematically summarized the structures of 259 compounds isolated from the genus Leonurus, featured with 147 labdane diterpenoids. The reported bioactivity studies up to 2017 are presented in the second part, with the main focus on the isolated compounds and also concerning the extracts...
March 2018: Phytochemistry
https://www.readbyqxmd.com/read/29328664/aconicarmisulfonine-a-a-sulfonated-c-20-diterpenoid-alkaloid-from-the-lateral-roots-of-aconitum-carmichaelii
#17
Qinglan Guo, Huan Xia, Gaona Shi, Tiantai Zhang, Jiangong Shi
A novel sulfonated C20 -diterpenoid alkaloid with an unprecedented carbon skeleton and significant analgesic activity (46.7% inhibition at 0.1 mg/kg, i.p.), named aconicarmisulfonine A (1), was isolated from an aqueous extract of the lateral roots of Aconitum carmichaelii. Its structure was determined by comprehensive analysis of spectroscopic data, especially by 2D NMR spectroscopic data combined with ECD calculation and single-crystal X-ray diffraction. The plausible biosynthetic pathways of compound 1 are also discussed...
February 2, 2018: Organic Letters
https://www.readbyqxmd.com/read/29248451/features-and-outcomes-of-drugs-for-combination-therapy-as-multi-targets-strategy-to-combat-alzheimer-s-disease
#18
REVIEW
Atish Kumar Sahoo, Jagnehswar Dandapat, Umesh Chandra Dash, Satish Kanhar
ETHNOPHARMACOLOGICAL RELEVANCE: Alzheimer's disease (AD), a deleterious neurodegenerative disorder that impairs memory, cognitive functions and may lead to dementia in late stage of life. The pathogenic cause of AD remains incompletely understood and FDA approved drugs are partial inhibitors rather than curative. Most of drugs are synthetic or natural products as galanthamine is an alkaloid obtained from Galanthus spp. Huperzine A, an alkaloid found in Huperzia spp., gingkolides a diterpenoids from Gingko biloba and many ethnobotanicals like Withania somnifera (L...
April 6, 2018: Journal of Ethnopharmacology
https://www.readbyqxmd.com/read/29212360/a-new-denudatine-type-c-20-diterpenoid-alkaloid-from-aconitum-sinchiangense-w-t-wang
#19
Ahmatbeck Samanbay, Bo Zhao, Haji Akber Aisa
A new denudatine-type C20 -diterpenoid alkaloid, designated as sinchianine (1), together with eight known diterpenoid alkaloids, 12-acetyl-12-epi-napelline (2), 12-epi-napelline (3), neoline (4), talatisamine (5), 14-O-acetylsenbusine A (6) and benzoylaconine (7), songorine (8) and aconitine (9), were isolated from the whole herb of Aconitum sinchiangense W. T. Wang. Their structures were elucidated on the basis of extensive spectroscopic analyses (NMR and HR-ESI-MS) and comparison with data reported in the literature...
December 6, 2017: Natural Product Research
https://www.readbyqxmd.com/read/29205735/stereoselective-total-synthesis-of-hetisine-type-c-20-diterpenoid-alkaloids-spirasine-iv-and-xi
#20
Quanzheng Zhang, Zhongshan Zhang, Zhong Huang, Changhui Zhang, Song Xi, Min Zhang
The first total synthesis of the architecturally complex hetisine-type heptacyclic C20 -diterpenoid alkaloids (±)-spirasine IV and XI is reported. The A/F/G/C tetracyclic skeleton with the challenging N-C6 and C14-C20 linkages was efficiently constructed by an intramolecular azomethine-ylide-based 1,3-dipolar cycloaddition with unusual regioselectivity. SmI2 -mediated free-radical addition to the arene moiety without prior dearomatization and a stereoselective intramolecular aldol reaction further enabled rapid access to the hetisine core, providing a bicyclo[2...
January 22, 2018: Angewandte Chemie
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