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Rapid comparison of antitumor chemical constituents and mechanisms between Dendrobium nobile and Dendrobium officinale by UPLC-IT-TOF, network pharmacology and experimental verification

Liu Jie, Li Zhaoyang, Zeng Meiling, Liang Yan, Liang Bing, Ge Qiuping, Zhang Xiaoyan, Zhang Shilin, Zhou Wei

Acta Chromatographica

2023

Vol. 35, no. 2

123--138

Dendrobium nobile and Dendrobium officinale as the main varieties of traditional Chinese medicine Dendrobium are widely used in clinic. The study aimed to systematically explore chemical constituents and their antitumor effect of D. nobile and D. officinale by ultra-performance liquid chromatography coupled with ion trap time-of-flight mass spectrometry (UPLC-IT-TOF), network pharmacology and cancer cell experiments. D. nobile extract and D. officinale extract could significantly inhibit the proliferation of human lung cancer A549 cells, human liver cancer HepG2 cells and human breast cancer MCF-7 cells in the dose-dependent manner (P < 0.05), the antitumor effect of D. officinale extract was stronger than that of D. nobile extract at the same drug concentration. A total of 40 chemical constituents of D. nobile and D. officinale including phenanthrenes, bibenzyls and other types of compounds had been identified by UPLC-IT-TOF, LCMSsolution and MetID software according to retention times, accurate mass, MSⁿ fragmentation, reference compounds and natural product databases. Phenanthrenes with good antitumor activity were mainly present in D. nobile, bibenzyls were the main compounds of D. officinale. Integrated networks of Herb-Compounds-Targets-Cancer revealed that gigantol, moscatilin, tristin, moscatin and densiflorol B were regarded as key antitumor compounds of D. nobile and D. officinale, D. nobile and D. officinale shared 7 targets accounting for 70% of the antitumor core targets, more than half of their antitumor KEGG pathways were similar. The results of molecular docking and western blotting experiments indicated that the antitumor mechanisms of D. nobile and D. officinale may be through inhibiting PI3K-Akt and HIF-1α signaling pathways.

Antitumor chemical constituents of Toddalia asiatica (Linn) Lam root bark and its rational alternative medicinal parts by multivariate statistical analysis

Luo Cairong, Liu Jie, Liang Yan, Shen Xiangchun, Zhang Xiaoyan, Zhou Wei

Acta Chromatographica

2021

Vol. 33, no. 2

153--161

Toddalia asiatica (Linn) Lam (T. asiatica) as a traditional Miao medicine was investigated to find rational alternative medicinal parts for T. asiatica root bark and its antitumor chemical constituents by quantitative pharmacognostic microscopy, high performance liquid chromatography (HPLC) fingerprint and multivariate statistical analysis. A bivariate correlation analysis method based on microscopic characteristics and content of chemical constituents was established for the first time, there were some regular discoveries between powder microscopic characteristics and common chromatographic peaks of T. asiatica through quantitative pharmacognostic microscopy, cork cells, calcium oxalate square crystal, brown clump, starch granule and phloem fiber, as powder microscopic characteristics may be placed where the main chemical constitutes were enriched. Scores plot of principal component analysis (PCA) and dendrogram of hierarchical clustering analysis (HCA) showed that 18 T. asiatica samples were distinguished correctly, clustered clearly into two main groups as follows: S01∼S03 (root bark) and S07∼S09 (stem bark) in cluster 1, S04∼S06 and S10∼S18 in cluster 2. Nineteen common peaks were obtained in HPLC fingerprint of T. asiatica, loadings plot of PCA indicated seven compounds played important roles in different part of samples (P10 > P08 > P07 > P14 > P16 > P17 > P19), peaks 04, 06, 07, 08, 10 were identified as hesperidin, 4-methoxycinnamic acid, toddalolactone, isopimpinlline and pimpinellin. MTT assay was used to determine the inhibitory activity of different medicinal parts of T. asiatica on human breast cancer MCF-7 cells, all parts of T. asiatica had different inhibitory effects on MCF-7 cell lines, root and stem barks of T. asiatica showed the best inhibitory activity. The relationship between chemical constituents and the inhibitions on MCF-7 cell had been established, significant antitumor constituents of T. asiatica were identified by correlation analysis, the order of the antitumor effect of the main compounds was P07 (toddalolactone) > P16 > P06 (4-methoxycinnamic acid), P11 > P18 > P10 (pimpinellin) > P08 (isopimpinellin) > P01 > P19 > P14 > P04 (hesperidin) > P17, which were antitumor chemical constituents of T. asiatica root bark. T. asiatica stem bark was the most rational alternative medicinal part for T. asiatica root bark.

Rational Design, synthesis and Biological Evaluation of 3H-Naphtho[1,2,3-de]quinoline-2,7-diones: a New Class of Potential Antitumor Agents

Antonini L., Polucci P., Magnano A., Sparapani S., Martelli S.

Polish Journal of Chemistry

2004

Vol. 78 / nr 8

1019-1025

A series of novel potential DNA-binding antitumor agents, 6-[(_-aminoalkyl)amino]- 3H-naphtho[1,2,3-de]quinoline-2,7-diones 3a-j, has been prepared by nucleophilic substitution of commercially available 6-bromo-4-methyl-1-phenyl-3Hnaphtho[ 1,2,3-de]quinoline-2,7-dione with the suitable 1-[_-(alkylamino)alkyl]amine. In vitro cytotoxic potencies of these derivatives toward six tumor cell lines, including human colon adenocarcinoma (HT29) and human ovarian carcinoma (A2780 sensitive, A2780cisR cisplatin-resistant, CH1, CH1cisR cisplatin-resistant, and SKOV-3), are described and compared to that of reference drugs. The 6-[3-(diethylamino)propyl]- 3H-naphtho[1,2,3-de]quinoline-2,7-diones (3e), which possesses good cytotoxicity and low or none cross resistance with Cs on resistant cell lines, can be regarded as a new lead in the development of intercalating anticancer derivatives.