ABSTRACT
A strategy combining collision cross section(CCS) prediction and quantitative structure-retention relationship(QSRR) model for quinoline and isoquinoline alkaloids was established based on UHPLC-IM-Q-TOF-MS and applied to Phellodendri Chinensis Cortex and Phellodendri Amurensis Cortex. The strategy included the following three steps.(1) The molecular features were extracted by the "find features" algorithm.(2) The potential quinoline and isoquinoline alkaloids were screened by filtering the original characteristic ions extracted from Phellodendri Chinensis Cortex and Phellodendri Amurensis Cortex by the established CCS vs m/z prediction interval.(3) According to the retention time of candidate compounds predicted by QSRR model, the chemical constituents were identified in combination with the characteristic fragment ions and pyrolysis law of secondary mass spectrometry. With the strategy, a total of 80 compounds were predicted, and 15 were identified accurately. The strategy is effective for the identification of small analogs of traditional Chinese medicine.
Subject(s)
Chromatography, High Pressure Liquid , Algorithms , Alkaloids , Isoquinolines , QuinolinesABSTRACT
Objective: To study the quinoline alkaloids from the ethanol extract of Scolopendra subspinipes mutilans (SSM). Methods: The chemical constituents were isolated and purified by macroporous resin column, medium pressure preparation chromatography, and semi-preparative HPLC. Their structures were elucidated by IR, MS, and NMR experiments. Results: Three quinolone alkaloids were obtained and identified as 3-hydroxy-4-methoxyquinolin-8-yl hydrogen sulfate (1), jineol-8-sulfate (2), and jineol (3), respectively. Conclusion: Compound 1 is a new compound from SSM.
ABSTRACT
The root bark of Dictamnus dasycarpus is one of common traditional Chinese medicines (TCMs). Quinoline alkaloids are one of the main active substances in this TCM and possess many biological activities including anti-titumor, anti-inflammation, anti-bacteria, anti-oxidation, and anti-platelet aggregation activities. In this study, eight quinoline alkaloids 1-8 were firstly separated from the root barks of D. dasycarpus. It was difficult to isolate more quinoline alkaloids from the remaining fraction 8 in D. dasycarpus by this conventional chemical separation, so the target analysis method combined LC-MS guided-separation of quinoline alkaloids from fraction 8 was established. MS/MS fragmentation patterns of eight quinoline alkaloids reference standard compounds 1-8 were studied by ultra-performance liquid chromatography-electrospary ionization-mass spectrometry (UPLC-ESI-MS/MS). Based on the feature fragment ion 200, the parent ion scan mode was established for the target analysis of quinoline alkaloids in fraction 8. Finally, 8-methoxyflindersine (9) and N-metilatanina (10) were discovered and isolated quickly from fraction 8 guided by LC-MS, and their structures were identified by NMR and MS. Among them, compound 10 was isolated from the genus Dictamnus for the first time. These results indicated that this method is not only quick and sensitive for analyzing the quinoline alkaloids, but also to effectively guided-separate this kind of alkaloids in the root barks of D. dasycarpus.
Subject(s)
Alkaloids , Chromatography, High Pressure Liquid , Dictamnus , Chemistry , Ions , Phytochemicals , Plant Roots , Chemistry , Quinolines , Spectrometry, Mass, Electrospray Ionization , Tandem Mass SpectrometryABSTRACT
Abstract Choisya ternata Kunth, C. ternata var. sundance Kunth and the hybrid Choisya 'Aztec-Pearl' are three related species belonging to the Rutaceae family. Ethanol extracts were prepared from the leaves of these three species and evaluated in relation to their antioxidant activity using in vitro and ex vivo models. The ethanol extracts belonging to the three species produced a very high antioxidant profile as evidenced by the DPPH radical scavenging activity, the determination of total phenolics and flavonoid equivalent. The generation of reactive species of oxygen in leukocytes stimulated with LPS was dramatically reduced when the three ethanol extracts were used. The alkaloids anhydroevoxine and choisyine were isolated from the ethanol extract of C. ternata using HEMWat (4:6:5:5) as the solvent system by means of high-speed countercurrent chromatography. This was the first time quinoline alkaloids were isolated from this species using HSCCC. These compounds were also assayed for their capacity to inhibit the generation of ROS in leukocytes stimulated by LPS and the results also suggested that they are reactive oxygenase inhibitors.
ABSTRACT
Objective: To study the alkaloids from Ervatamia hainanensis. Methods: The alkaloids were isolated and purified by silica gel, MCI, Sephadex LH-20 column chromatography, and semi-preparative HPLC, and their structures were elucidated by physical and spectroscopic analysis. Results: Twelve alkaloids were obtained and identified as coronaridine (1), 19-epi-heyneanine (2), 9,10-dimethoxycoronaridine (3), vobasine (4), vobasine N(4)-oxide (5), 3-oxo-19-epi-heyneanine (6), strictamine (7), deacetylakuammiline (8), pandine (9), rhazicine (10), rhazicine N(4)-oxide (11), and rhazimine (12). Conclusion: Compounds 8 and 10-12 are isolated from the genus Ervatamia Stapf for the first time, while compounds 3 and 5-7 are firstly obtained from E. hainanensis.
ABSTRACT
AIM@#To investigate the quinoline alkaloids from the roots of Dictamnus angustifolius G.Don ex Sweet (Rutaceae).@*METHOD@#The quinoline alkaloids were isolated by various column chromatographic methods and their structures were elucidated on the basis of spectral analysis.@*RESULTS@#A new quinoline alkaloid, 5-methoxylrobustine (1), along with five known quinoline alkaloids were obtained, and their structures were identified as dictamnine (2), robustine (3), isopteleine (4), γ-fagarine (5), and skimmianine (6). Cytotoxicity testing of these alkaloids showed that all of them had weak cytotoxic activities against human breast cancer cells (MCF7).@*CONCLUSION@#Compound 1 is a new quinoline alkaloid. Alkaloid 3 showed stronger anti-proliferation effect than the other alkaloids.