MOLECULES
·
2023
·Vol. 28
·期 6
·2531
·
IF 4.6
Da Song,Jia-Jun Liang,Shi-Biao Pu,Pan-Pan Zhang,Yun-Lin Peng,Xia Liu,Ting-Ting Feng,Xiang Pu,Ying Zhou,Xiong-Wei Liu,Xin Wei
Two new monoterpenoid indole alkaloids, gelselegandines F (1) and G (2), were isolated from the aerial parts ofGelsemium elegans. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD calculations were conducted at the B3LYP/6-311G(d,p) level and NMR calculations were carried out using the Gauge-Including Atomic Orbitals (GIAO) method. Structurally, the two new compounds possessed rare, cage-like, monoterpenoid indole skeletons. All isolated compounds and the total alkaloids extract were tested for cytotoxicity against four different tumor cell lines. The total alkaloids extract ofG. elegansexhibited significant antitumor activity with IC50values ranging from 32.63 to 82.24 ug/mL. In order to discover anticancer leads from the active extraction, both new indole compounds (1–2) were then screened for cytotoxicity. Interestingly, compound2showed moderate cytotoxicity against K562 leukemia cells with an IC50value of 57.02 uM.Keywords:gelselegandines F and G;cytotoxicity;leukemic cells;Gelsemium elegans
研究领域:
药理学
·
有机化学
·
癌症研究
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FITOTERAPIA
·
2025
·
IF 2.6
Li-Li Ye,Meng-Yue Yang,Xiang-Hai Cai
Eight new gelsedine-type oxindole alkaloids and ten known analogues were isolated from the stems and leaves of Gelsemium elegans . Gelseansdine A ( 1 ) was an N 4 -deficient Gelsemium alkaloid, while gelseansdines E–H ( 12 , 14 , 16 – 17 ) represented a class of alkaloids polymerized with iridoid. Their structures were elucidated based on UV, HRESIMS, NMR spectroscopy, and electronic circular dichroism (ECD) data analyses. Additionally, the isolated compounds were screened for their inhibitory activity on macrophage M2 polarization.
研究领域:
植物化学
·
药物化学
·
免疫学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Evidence-based Complementary and Alternative Medicine
·
2017
·
IF 1.74
Yinghao Wang,Heshan Wang,Shuisheng Wu,Desen Li,Sainan Chen
Gelsemium elegans (GE) is a kind of well-known toxic plant. It can be detoxified by Mussaenda pubescens (MP), but the detoxification mechanism is still unclear. Thus, a detoxification herbal formula (GM) comprising GE and MP was derived. The Caco-2 cells monolayer model was used to evaluate GM effects on transporting six kinds of indole alkaloids of GE. The bidirectional transport studies demonstrated that absorbance percentage of indole alkaloids in GE increased linearly over time. But in GM, Papp (AP→BL) values of the most toxic members, gelsenicine, humantenidine, and gelsevirine, were lower than that of Papp (BL→AP) (). The prominent analgesic effect members, gelsemine and koumine, were approximately 1.00 in values. Nowhere was this increasing efflux more pronounced than in the case of indole alkaloids with N-O structure. In the presence of verapamil, the values of humantenidine, gelsenicine, gelsevirine, and humantenine were decreased by 43.69, 41.42, 36.00, and 8.90 percent, respectively. The values in presence of ciclosporin were homologous with a decrease of 42.32, 40.59, 34.00, and 15.07 percent. It suggested that the efflux transport was affected by transporters. Taken together, due to the efflux transporters participation, the increasing efflux of indole alkaloids from GM was found in Caco-2 cells.
研究领域:
药理学
·
毒理学
·
中药学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FORENSIC SCIENCE INTERNATIONAL
·
2021
·
IF 2.395
Dong Qu,Dong-Fang Qiao,Xun-Cai Chen,Chun-Qiong Feng,Qi-Zhi Luo,Xiao-Hui Tan
We present a case of fatal poisoning from accidental ingestion of Gelsemium elegans ( G. elegans ), a rarely toxic plant. A 41-year-old man was found dead, at his home, 6 h after drinking homemade herbal liqueur during lunch. Autopsy and routine toxicological analyses identified neither significant pathological findings nor routine poisons. However, a local botanist revealed that the homemade herbal liqueur contained G. elegans , a poisonous plant specific to Asia. To ascertain whether the decedent had ingested G. elegans , we performed liquid chromatography-mass spectrometry (LC-MS) and found two alkaloids (gelsemine and koumine) in his blood, gastric contents, as well as the suspected herbal liqueur. The cause of death was therefore confirmed to be G. elegans poisoning. Case reports of fatal poisoning due to ingestion of G. elegans are quite rare in English. Therefore, the present case broadens the scope on the possibility of death due to ingestion of G. elegans for forensic pathologists and toxicologists.
研究领域:
法医病理学
·
毒理学
·
植物学
·
法医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF PEST SCIENCE
·
2024
·
IF 4.3
Zheng Qun,Yan Wenjuan,Zhu Shiqi,Miao Xiaoran,Wu Jian,Lin Zewei,Huang Suqing,Cheng Dongmei,Xu Hanhong,Zhang Zhixiang,Zhang Peiwen
Gelsemium elegans Benth. ( Loganiaceae ), also known as heartbreak herb, can be used in the manufacture of herbal medicines. Insecticidal activity has also been found and can be used to develop botanical insecticides. This study aimed to reveal the insecticidal mechanism of its extracts against red fire ants and provide strategies for the development of biopesticides and the promotion of green and sustainable agriculture. 16s rRNA, pathohistological, behavioral, and enzyme activity assays were performed to reveal its biological effects, including the effects on non-target organisms. Our results showed that red fire ants exposed to G. elegans extracts exhibited slowed growth, reduced feeding, and decreased aggressiveness. The midgut and its peritrophic membrane of red fire ant were significantly disrupted, the diversity of gut microbial community was reduced, and the balance of microbial composition was disturbed. Significant increases in functional abundance of xenobiotics biodegradation and metabolism pathway and P450s enzyme activity confirmed the toxic stress of G. elegans extract. Functional prediction of Kyoto Encyclopedia of Genes and Genomes pathway showed that the functional abundance of novobiocin biosynthesis, flavonoid biosynthesis, lysosome, proteasome, and wingless/integrated signaling pathways were significantly inhibited in the gut. Besides, G. elegans extracts induced an increase in acetylcholinesterase activity. These results revealed dysregulation of immune system and metabolic functions in red fire ants, as well as toxic effects of G. elegans extracts on physiological functions and nerves. These findings revealed the insecticidal mechanism of G. elegans and supported the development of eco-friendly insecticides for red fire ants.
研究领域:
昆虫学
·
微生物学
·
药理学
·
农业科学
·
分子生物学
✓ 已验证
产品关联
DOI
高影响因子
Acta Pharmaceutica Sinica B
·
2025
·
IF 14.6
Niping Li,Yaorong Yang,Shengyuan Zhang,Bin Jiang,Wei Zhang,Haibo Wang,Lixin Chen,Liwei Wang,Yiyi Li,Lei Shi,Wencai Ye,Lei Wang
Gelsemium elegans ( G. elegans ) is an extremely poisonous plant that is widely distributed in southern China and southeastern Asia. G. elegans poisoning events occur frequently in southern China, and are therefore an urgent public health problem requiring multidisciplinary action. However, the toxic components and toxicological mechanisms remain unclear. Here, we describe a systematic investigation on the toxic components of G. elegans , resulting in the isolation and identification of 120 alkaloids. Based on acute toxicity screening, the structure–toxicity relationship of Gelsemium alkaloids was proposed for the first time. Moreover, gelsedine- and humantenine-type alkaloids were detected in the clinical blood sample, and were confirmed to be causative in the poisoning. The most toxic compound, gelsenicine ( 1 ), had selective inhibitory effects toward ventral respiratory group (VRG) neurons in the medulla, which is the main brain region controlling respiration in the central nervous system. Gelsenicine ( 1 ) strongly inhibited the firing of action potentials in VRG neurons through its ability to stimulate GABA A receptors, the main receptors involved in inhibitory neurotransmission. Application of GABA A receptor antagonists successively reversed action potential firing in gelsenicine ( 1 )-treated VRG neurons. Importantly, the GABA A receptor antagonists securinine and flumazenil significantly increased the survival of poisoned animals. Our findings provide insight into the components and mechanisms of G. elegans toxicity, and should assist the development of effective emergency treatments for G. elegans poisoning.
研究领域:
毒理学
·
药理学
·
神经科学
·
植物学
·
急诊医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Scientific Reports
·
2026
·
IF 4.9
Lu Zou,Ye Lin,Anzhong Wu,Junfei Huang,Runsang Pan,Hua Guo,Liya Liu
In this study, in response to a Gelsemium elegans Benth poisoning incident triggered by the consumption of homemade infused wine, the collected infused wine and the patient’s biological samples (blood and urine) were systematically examined using an integrated analytical strategy that combines UPLC-Q-TOF-MS non-targeted screening and UPLC-MS/MS targeted quantification. By constructing a database of Gelsemium elegans Benth alkaloid components, a total of nine major alkaloid components were identified, and a rapid quantitative analysis method was established for five of the key components (Gelsemine, Koumine, Gelsenicine, Gelsevirine, Humantenine). The results of the study showed that the content of Gelsemium elegans Benth alkaloids in infused wine was high, with Gelsenicine amounting to 60.87 µg/mL, which was estimated on the basis of its LD₅₀ (0.1–0.2 mg/kg bw) reported in the literature, and that an adult’s intake of 115–230 mL can be lethal. In the methodological validation, the spiked recoveries of infused wine and urine samples were 87.16%-105.53% with an RSD of < 7%, indicating that the method is accurate, reliable and does not require an internal standard, which makes it suitable for emergency testing in economically underdeveloped areas. In addition, Humantenine was detected in the urine of all poisoned individuals in this study, suggesting its potential as a potential marker for poisoning. Although the blood samples could not be quantified accurately due to matrix interference, the established coupling technology provides an effective analytical paradigm for the rapid identification and mechanism study of poisoning, and provides technical support for clinical diagnosis and public health emergency response.
✓ 已验证
产品关联
DOI
PubMed
高影响因子
BIOORGANIC CHEMISTRY
·
2021
·
IF 5.275
Ni-Ping Li,Jun-Shan Liu,Jiao-Wen Liu,Hai-Yan Tian,Hong-Ling Zhou,Yuan-Ru Zheng,Xiao-Jun Huang,Jia-Qing Cao,Wen-Cai Ye,Lei Wang
Two novel monoterpenoid indole alkaloids (MIAs), gelsechizines A-B ( 1 – 2 ), along with four known ones ( 3 – 6 ) were isolated from the fruits of Gelsemium elegans . Compound 1 features a new carbon skeleton with two additional carbon atoms forming a 4-methylpyridine unit. Their structures with absolute configurations were elucidated by NMR, MS, X-ray diffraction and electronic circular dichroism (ECD) calculations. Compounds 1 – 3 showed significant anti-inflammatory effects in vivo and in vitro , which may be related to the inhibition of the trecruitment of neutrophils and macrophages as well as the secretion of TNF- α and IL-6. Preliminary structure–activity relationship analysis revealed that the β - N -acrylate moiety plays an important role in the anti-inflammatory effect.
研究领域:
药理学
·
有机化学
·
炎症研究
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHEMISTRY & BIODIVERSITY
·
2023
·
IF 2.9
Pan-Pan Zhang,Jia-Jun Liang,Qing-Yu Lu,Xin Yin,Yong-Qiang Zhou,Ting-Ting Feng,Ying Zhou,Dong Chang,Xin Wei
Gelsegansymines A (1) and B (2), two new indole alkaloids along with six known analogues (3-8) were isolated from the aerial parts of Gelsemium elegans. Their structures were elucidated by means of spectroscopic techniques. Structurally, compounds 1 and 2 possessed the rare cage-like gelsedine skeleton hybrid with bicyclic monoterpenoid. The anti-inflammatory activities of isolated compounds (1-3) were tested on LPS induced RAW264.7 cells. Under the treated concentration without toxicity for cells, the cytokines levels of nitric oxide (NO), tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) were evaluated by Griess method and enzyme-linked immunosorbent assay (ELISA). The results showed that compounds 1-3 exhibited anti-inflammatory activities with dose-dependent manner range from 12.5 to 50 µmol/L. Furthermore, the inhibitory activities of compounds 1 and 2 on receptor activator of NF-κB ligand (RANKL) induced osteoclast formation were tested in vitro. Compounds 1 and 2 at 5 µmol/L exhibited the significant inhibitory effect on the osteoclastogenesis induced by RANKL. This work reported the anti-inflammatory and osteoclast inhibitory activities of new monoterpenoid indole hybrids, which may inspire the further light on the related traditional application research of G. elegans.
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）