4.4 Article

Anti-cancer and anti-inflammatory new vakognavine-type alkaloid from the roots of Aconitum carmichaelii

Journal

TETRAHEDRON LETTERS
Volume 57, Issue 52, Pages 5881-5884

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.11.065

Keywords

Vakognavine-type alkaloid; Aconitum carmichaelii; Anti-cancer activity; Anti-inflammatory activity

Funding

  1. Macao Science and Technology Development Fund [086/2013/A3]
  2. Natural Science Foundation of China [51428303]
  3. Sino-Africa Joint Research Project [SAJC20160233]

Ask authors/readers for more resources

Vakognavine-type alkaloids are a rare kind of diterpenoid alkaloid isolated from Delphinium and Aconitum species. During our research on the chemical constituents of the roots of Aconitum carmichaelii, a new vakognavine-type alkaloid (1) along with a known vakognavine-type alkaloid, trifoliolasine E (2), and two known hetisine-type alkaloids (3 and 4) were obtained. The structures were elucidated by a combination of high resolution ESI-MS, 1D and 2D NMR spectra. Compound 1 showed strong inhibitory effects on HT-29, SGC-7901, and HepG2 cell lines with IC50 values of 0.948, 0.983, and 3.645 mu M, respectively, while trifoliolasine E (2) exhibited moderate activities. Compound 1 was also found to dose-dependently inhibit the activity of cyclooxygenase-2 (COX-2) with an IC50 value of 29.75 mu M. To the best of our knowledge, this is the first report on the bioactivity of vakognavine-type diterpenoid alkaloids. (C) 2016 Published by Elsevier Ltd.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Review Food Science & Technology

Antioxidant and anticancer potentials of edible flowers: where do we stand?

Sajad Fakhri, Merve Tomas, Esra Capanoglu, Yaseen Hussain, Fatemeh Abbaszadeh, Baiyi Lu, Xiaolan Hu, Jianlin Wu, Liang Zou, Antonella Smeriglio, Jesus Simal-Gandara, Hui Cao, Jianbo Xiao, Haroon Khan

Summary: Edible flowers are rich sources of phytochemicals with various therapeutic effects, such as anti-oxidative, anti-inflammatory, and anti-microbial properties. They exhibit promising anticancer effects by modulating oxidative stress pathways and apoptotic/inflammatory mediators.

CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION (2022)

Article Chemistry, Applied

Investigation and dynamic profiling of oligopeptides, free amino acids and derivatives during Pu-erh tea fermentation by ultra-high performance liquid chromatography tandem mass spectrometry

Shengshuang Chen, Yu Fu, Xiqing Bian, Ming Zhao, Yilang Zuo, Yahui Ge, Ying Xiao, Jianbo Xiao, Na Li, Jian-Lin Wu

Summary: This study utilized UHPLC-Q-TOF/MS to analyze the dynamic changes of oligopeptides, free amino acids, and derivatives during Pu-erh tea fermentation, and found that certain N-acetyl amino acids may act as potential inhibitors of neurokinin-1 receptor. Additionally, the results of metamicrobiology indicated that Aspergillus niger and Aspergillus luchuensis were more efficient in metabolizing proteins, oligopeptides, and amino acids during fermentation.

FOOD CHEMISTRY (2022)

Article Chemistry, Applied

Discovery of novel ascorbic acid derivatives and other metabolites in fruit of Rosa roxburghii Tratt through untargeted metabolomics and feature-based molecular networking

Yaqi Zhang, Xiqing Bian, Guanyu Yan, Baoqing Sun, Wen Miao, Mingzheng Huang, Na Li, Jian-Lin Wu

Summary: In this study, a non-targeted LC-MS approach was used to identify 251 metabolites in Fruit of Rosa roxburghii Tratt (FRR). Differential compounds were identified to distinguish FRR from related species, and FRR exhibited higher biofunction potential. A quantitative LC-MS method was established to determine the contents of specific compounds, and it was found that FRR had higher contents compared to a related species. Furthermore, new ascorbic acid derivatives were discovered in FRR. These findings provide important information for the exploitation of FRR.

FOOD CHEMISTRY (2023)

Article Clinical Neurology

Identification of proline, 1-pyrroline-5-carboxylate and glutamic acid as biomarkers of depression reflecting brain metabolism using carboxylomics, a new metabolomics method

Xiqing Bian, Na Zhou, Yiran Zhao, Yichao Fang, Na Li, Xin Zhang, Xuan Wang, Yunxia Li, Jian-Lin Wu, Tingting Zhou

Summary: This study aimed to illustrate the metabolic mechanisms of depression and diagnose depression through biomarkers. The results showed that proline, 1-pyrroline-5-carboxylate (P5C), and glutamic acid may be potential biomarkers for depression. Additionally, serum samples could be an alternative diagnostic approach for depression.

PSYCHIATRY AND CLINICAL NEUROSCIENCES (2023)

Article Chemistry, Applied

Polarity-extended composition profiling via LC-MS-based metabolomics approaches: A key to functional investigation of Citrus aurantium L

Wen Miao, Xiaojing Liu, Na Li, Xiqing Bian, Yiran Zhao, Jing He, Tingting Zhou, Jian-Lin Wu

Summary: In this study, multiple liquid chromatography-mass spectrometry (LC-MS) metabolomics approaches were used to comprehensively characterize the components of Citrus aurantium L. Thirteen polymethoxyflavones (PMFs), 28 carbohydrates, and 18 carboxylic acids were identified for the first time in C. aurantium. A total of 147 compositions were characterized, including 92 that were reported for the first time. Geographical features and principal discriminative compounds were determined, and the biofunctions of C. aurantium from different regions were speculated.

FOOD CHEMISTRY (2023)

Article Plant Sciences

Neoline, fuziline, songorine and 10-OH mesaconitine are potential quality markers of Fuzi: In vitro and in vivo explorations as well as pharmacokinetics, efficacy and toxicity evaluations

Xiaocui Li, Weiqing Hou, Tingting Lin, Jiadong Ni, Huawei Qiu, Yu Fu, Zhongxiang Zhao, Caihua Yang, Na Li, Hua Zhou, Rong Zhang, Zhongqiu Liu, Ling Fu, Lijun Zhu

Summary: After evaluating the efficacy and toxicity of Fuzi, seven potential efficacy- or toxicity-specific quality markers were found. Among them, NE, FE, and SE were more efficacy-specific than BMA, and 10-OH MA was as toxicity-specific as MA.

JOURNAL OF ETHNOPHARMACOLOGY (2023)

Article Environmental Sciences

DEHP exposure elevated cardiovascular risk in obese mice by disturbing the arachidonic acid metabolism of gut microbiota

Xuyang Chai, Luyao Wen, Yuanyuan Song, Xiaochong He, Jingxian Yue, Jianlin Wu, Xin Chen, Zongwei Cai, Zenghua Qi

Summary: This study investigates the key characteristics of cardiovascular risk in diet-induced obese mice and corresponding normal mice exposed to DEHP at environmentally relevant concentrations. The results suggest that the cardiovascular system of obese individuals is more susceptible to DEHP exposure. DEHP exposure induces gut microbial remodeling and alters arachidonic acid metabolism, which is associated with adverse cardiovascular events. The findings provide new insights into DEHP-induced cardiovascular damage in obese individuals and suggest the potential use of arachidonic acid as a modulator of gut microbiota to prevent related diseases.

SCIENCE OF THE TOTAL ENVIRONMENT (2023)

Article Pharmacology & Pharmacy

Ultrasensitive quantification of trace amines based on N-phosphorylation labeling chip 2D LC-QQQ/MS

Xiqing Bian, Yida Zhang, Na Li, Menglin Shi, Xiaolin Chen, Hui-Lu Zhang, Jie Liu, Jian-Lin Wu

Summary: Trace amines (TAs) are metabolically related to catecholamine and associated with cancer and neurological disorders. A sensitive method using diisopropyl phosphite coupled with chip two-dimensional liquid chromatography tandem triple-quadrupole mass spectrometry (LC-QQQ/MS) was developed to simultaneously determine TAs and associated metabolites. The results showed significantly altered TAs and associated metabolites in hepatoma cells after sorafenib treatment, indicating the potential for elucidating disease mechanisms and diagnosing diseases based on the physiological functions of TAs.

JOURNAL OF PHARMACEUTICAL ANALYSIS (2023)

Review Biochemistry & Molecular Biology

Decoding Metabolic Reprogramming in Plants under Pathogen Attacks, a Comprehensive Review of Emerging Metabolomics Technologies to Maximize Their Applications

Ahmed Serag, Mohamed A. Salem, Shilin Gong, Jian-Lin Wu, Mohamed A. Farag

Summary: Plants interact with various organisms and face diverse aggressions. They have the ability to synthesize a wide array of chemical compounds, but only a small portion has been characterized for defense responses. Our knowledge of their biosynthetic pathways and functions is still incomplete. Recent progress has been made in phenylpropanoids and oxylipids metabolism. Advanced analysis methods, including different metabolomics approaches, imaging, flux analysis, and bioinformatics tools, are needed for monitoring plant metabolic reprogramming. Future developments are necessary to better understand intricate metabolic interactions in plants.

METABOLITES (2023)

Article Chemistry, Applied

Carboxyl-containing components delineation via feature-based molecular networking: A key to processing conditions of fermented soybean

Yuye Gao, Yu Fu, Na Li, Yuetong Jiang, Xiaojing Liu, Congcong Gao, Lishuang Wang, Jian-Lin Wu, Tingting Zhou

Summary: A method was established to determine the composition and content of carboxyl-containing components (CCCs) in fermented soybeans, and the optimal fermentation conditions were selected. Sixteen chemical markers with significant differences were screened. This study is important for the development of functional foods and the quality evaluation of fermented foods.

FOOD CHEMISTRY (2023)

Article Food Science & Technology

Aroma correlation assisted volatilome coupled network analysis strategy to unveil main aroma-active volatiles of Rosa roxburghii

Ya-Hui Ge, Xue Li, Mingzheng Huang, Zhengxu Huang, Manman Wu, Baoqing Sun, Lishuang Wang, Jian-Lin Wu, Na Li

Summary: We proposed an aroma correlation assisted volatilome coupled network analysis strategy to study Rosa roxburghii and discovered various aroma-active volatiles. The predominant aromas in R. roxburghii were found to be contributed by a series of homologous C6-and C8-acids, alcohols, aldehydes, esters, and terpenoids. Two aroma-active and aroma-contributing volatile groups, acid-aldehyde-alcohol-ester and terpenoid groups, were identified with the network analysis. Furthermore, the accumulation of C6-and C8-family homologous aliphatic volatiles was explained with linoleic and linolenic acid derived pathways. This strategy is practical for investigating the main aroma-active volatiles based on volatilome.

FOOD RESEARCH INTERNATIONAL (2023)

Article Chemistry, Organic

Pyrrolidine-based C1-symmetric chiral transition metal complexes as catalysts in the asymmetric organic transformations

Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh

Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.

TETRAHEDRON LETTERS (2024)