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diterpenoid alkaloid

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
Haiyue Jiang, Shuai Huang, Feng Gao, Yongqi Zhen, Chunying Li, Xianli Zhou
A new C 19 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
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
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
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
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...
January 12, 2018: Phytochemistry
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...
January 12, 2018: Organic Letters
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...
December 14, 2017: Journal of Ethnopharmacology
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
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
Ji-Fa Zhang, Lin Chen, Shuai Huang, Lian-Hai Shan, Feng Gao, Xian-Li Zhou
Twenty-five diterpenoid alkaloids were isolated from the roots of two Aconitum species. The structures of seven new C19-diterpenoid alkaloids, apetaldines A-G (1-7), and 10 known alkaloids (8-17) from Aconitum apetalum and eight known alkaloids (18-25) from Aconitum franchetii var. villosulum were elucidated via HRESIMS, IR, and NMR data. Alkaloids 1-10, 15, 16, and 18-25 were screened for their antifeedant activity. Among the compounds tested, chasmanthinine (19) showed highly potent antifeedant activity with an effective concentration for 50% feeding reduction (EC50) at 0...
November 20, 2017: Journal of Natural Products
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[,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...
December 1, 2017: Organic Letters
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
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...
January 2018: Molecular Medicine Reports
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
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
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
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
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
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)...
December 2017: Toxicology in Vitro: An International Journal Published in Association with BIBRA
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