scholarly journals Evaluation of Microbial Transformation of 10-deoxoartemisinin by UPLC-ESI-Q-TOF-MSE

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3874
Author(s):  
Yue Bai ◽  
Dong Zhang ◽  
Peng Sun ◽  
Yifan Zhao ◽  
Xiaoqiang Chang ◽  
...  
Keyword(s):  
Model Organism ◽  
Microbial Transformation ◽  
Ultra Performance Liquid Chromatography ◽  
Cunninghamella Elegans ◽  
Software Products ◽  
Flight Mass Spectrometry ◽  
Cunninghamella Blakesleeana ◽  
Biotransformation Products ◽  
Semisynthetic Derivative ◽  
First Time

10-deoxoartemisinin is a semisynthetic derivative of artemisinin that lacks a lactone carbonyl group at the 10-position, and has stronger antimalarial properties than artemisinin. However, 10-deoxoartemisinin has limited utility as a therapeutic agent because of its low solubility and bioavailability. Hydroxylated 10-deoxoartemisinins are a series of properties-improved derivatives. Via microbial transformation, which can hydroxylate 10-deoxoartemisinin at multiple sites, the biotransformation products of 10-deoxoartemisinin have been investigated in this paper. Using ultra-performance liquid chromatography-electrospray ionization-quadrupole time-of-flight mass spectrometry (UPLC-ESI-Q-TOF-MSE) combined with UNIFI software, products of microbial transformation of 10-deoxoartemisinin were rapidly and directly analyzed. The hydroxylation abilities of nine microorganisms were compared using this method. All of the microorganisms evaluated were able to hydroxylate 10-deoxoartemisinin, and a total of 35 hydroxylated products were identified. These can be grouped into dihydroxylated 10-deoxoartemisinins, monohydroxylated 10-deoxoartemisinins, hydroxylated dehydrogenated 10-deoxoartemisinins, and hydroxylated hydrogenated 10-deoxoartemisinins. Cunninghamella echinulata and Cunninghamella blakesleeana are able to hydroxylate 10-deoxoartemisinin, and their biotransformation products are investigated here for the first time. Cunninghamella elegans CICC 40250 was shown to most efficiently hydroxylate 10-deoxoartemisinin, and could serve as a model organism for microbial transformation. This method could be used to generate additional hydroxylated 10-deoxoartemisinins for further research.

scholarly journals A Microbial Transformation Model for Simulating Mammal Metabolism of Artemisinin

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 315 ◽  
Author(s):  
Yue Ma ◽  
Peng Sun ◽  
Yifan Zhao ◽  
Kun Wang ◽  
Xiaoqiang Chang ◽  
...  
Keyword(s):  
Chinese Herb ◽  
Microbial Transformation ◽  
Ultra Performance Liquid Chromatography ◽  
The Body ◽  
Transformation Model ◽  
Cunninghamella Elegans ◽  
C Elegans ◽  
Traditional Chinese Herb

Artemisinin (ART) is a highly effective antimalarial agent isolated from the traditional Chinese herb Qinghao. Metabolism of ART and its derivatives in the body is one of the most pressing issues for pharmaceutical scientists. Herein, an efficient in vitro microorganism model for simulation of metabolism of ART in vivo was developed employing Cunninghamella elegans. Metabolites in the microbial transformation system and plasma of mice pre-administrated ART orally were analyzed by ultra-performance liquid chromatography (UPLC)-electrospray ionization (ESI)-quadrupole time-of-flight (Q-TOF)-mass spectrometry (MSE) combined with UNIFI software. Thirty-two metabolites were identified in vitro and 23 were identified in vivo. After comparison, 16 products were found to be common to both models including monohydroxylated ART, dihydroxylated ART, deoxyartemisinin, hydroxylated deoxyartemisinin, hydroxylated dihydroartemisinin (DHA), and hydroxylated deoxy-DHA. These results revealed that C. elegans CICC 40250 functioned as an appropriate model to mimic ART metabolism in vivo. Moreover, an overall description of metabolites of ART from C. elegans CICC 40250 has been provided. Notably, DHA was detected and identified as a metabolite of ART in mouse plasma for the first time.

Characterization of lignans in Forsythiae Fructus and their metabolites in rats by ultra-performance liquid chromatography coupled time-of-flight mass spectrometry

2020 ◽  
Author(s):  
Feng-xiang Zhang ◽  
Zi-ting Li ◽  
Chang Li ◽  
Min Li ◽  
Zhi-hong Yao ◽  
...  
Keyword(s):  
Ring Opening ◽  
Furan Ring ◽  
Ultra Performance Liquid Chromatography ◽  
Rat Plasma ◽  
Chemical Information ◽  
Flight Mass Spectrometry ◽  
Blood And Urine Samples ◽  
Metabolic Reactions ◽  
First Time

Abstract Objectives This study was designed to profile the chemical information of Forsythiae Fructus (FF) and investigate the in-vivo FF-related xenobiotics, especially for lignans. Methods Rats were oral administrated of FF and pinoresinol-4-O-glucoside, respectively. Blood and urine samples were collected after ingestion, and xenobiotics was profiled by an UPLC/Qtof MS method. Key findings A total of 19 lignans were identified or tentatively characterized in FF, and 63 lignan-related xenobiotics were found in rat plasma and urine after ingestion of FF. It was found that lignans could be transformed into metabolites by furan ring opening, hydrogenation, demethylation, dehydration and phase II reactions (sulfation and glucuronidation). The whole metabolic behaviour of bisepoxylignan was revealed by evaluating the metabolism of pinoresinol-4-O-glucoside in vivo. It was found that the configuration of C-8/C-8ʹ was retained after furan ring opening and metabolic reactions always occurred at position of C-3/C-4/C-5 or C-3ʹ/C-4ʹ/C-5ʹ. Additionally, other types components in FF and in vivo were also characterized. Conclusions This work revealed the in-vivo metabolism of FF, and reported the characteristic metabolic reactions of lignans for the first time. It was also provided the foundation for the further investigation on pharmacodynamic components of FF or TCMs containing FF.

scholarly journals Characterization and identification of the major flavonoids in Phyllostachys edulis leaf extract by UPLC–QTOF–MS/MS

2020 ◽  
Vol 32 (4) ◽  
pp. 228-237 ◽  
Author(s):  
S.-Y. Shao ◽  
Y. Ting ◽  
J. Wang ◽  
J. Sun ◽  
X.-F. Guo
Keyword(s):  
Mass Spectrometry ◽  
Leaf Extract ◽  
Ultra Performance Liquid Chromatography ◽  
Rapid Identification ◽  
Phyllostachys Edulis ◽  
Practical Applications ◽  
Mass Spectral ◽  
Flight Mass Spectrometry ◽  
Product Ions ◽  
First Time

Phyllostachys edulis (PES), the most important bamboo species in China, is widely distributed in East Asia. Flavonoids, which are important bioactive natural compounds, often have similar structures, making their structural elucidation difficult. The aim of this study was to represent valuable, reliable mass spectral data for the identification of flavonoids in plant leaves. Ultra-performance liquid chromatography–quadrupole time-of-flight mass spectrometry (UPLC–Q-TOF-MS/MS) method was established for characterization and identification of the major flavonoids in PES leaf extract. A total of 13 flavonoids were simultaneously characterized, and their proposed characteristic product ions and fragmentation pathways were investigated. Thirteen compounds were separated on an Agilent Zorbax RRHD SB-C18 column (150 mm × 2.1 mm, 1.8 μm). On the basis of comparing with the 4 reference standards and the literature data, the other 9 flavonoids were identified by tandem mass spectrometry (MS/MS). Eight compounds (compounds 1, 4, 5, 8, 9, 10, 11, and 12) were found in PES leaves for the first time. An efficient UPLC–QTOF-MS/MS method was successfully applied for the structural identification of flavonoids in PES leaves. These results have practical applications for the rapid identification and structural characterization of these compounds in crude bioactive extracts or mixtures.

scholarly journals Metabolic Profiling of Alpinetin in Rat Plasma, Urine, Bile and Feces after Intragastric Administration

Molecules ◽  
2019 ◽  
Vol 24 (19) ◽  
pp. 3458
Author(s):  
Jieying Qiu ◽  
Hongyu Wu ◽  
Feng Feng ◽  
Xiaoying He ◽  
Caihong Wang ◽  
...  
Keyword(s):  
Formic Acid ◽  
High Strength ◽  
Gradient Elution ◽  
Ultra Performance Liquid Chromatography ◽  
Rat Plasma ◽  
Intragastric Administration ◽  
Flight Mass Spectrometry ◽  
Metabolic Reactions ◽  
First Time

Alpinetin, a bioactive flavonoid, has been known to have a diverse therapeutic effect, with namely anti-inflammatory, anticancer and antioxidant effects with low systemic toxicity. This study aimed to obtain metabolic profiles of alpinetin in orally administrated rats. The metabolites of alpinetin were systematically analyzed and identified by ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The chromatographic separation was achieved on a High Strength Silica (HSS) T3 (1.8 μm, 2.1 × 100 mm) column with the mobile phase consisting of water containing 0.1% formic acid and acetonitrile with 0.1% formic acid via gradient elution. An extracted ion chromatogram strategy based on multiple prototype/metabolite intermediate templates and 71 typical metabolic reactions was proposed to comprehensively profile the metabolites of alpinetin. With the metabolite profiling strategy, altogether 15 compounds were recognized from urine, plasma, bile and feces of rats after intragastric administration of alpinetin for the first time. The prototype, glucuronide conjugates and phenolic acids metabolites were the probable predominant form of alpinetin in rats. This work showed a comprehensive study of the probable metabolic pathways of alpinetin in vivo, which could provide meaningful information for future pharmacological studies.

scholarly journals Metabolite Differences of Polyphenols in Different Litchi Cultivars (Litchi chinensis Sonn.) Based on Extensive Targeted Metabonomics

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1181
Author(s):  
Nonghui Jiang ◽  
Huili Zhu ◽  
Wei Liu ◽  
Chao Fan ◽  
Feng Jin ◽  
...  
Keyword(s):  
Main Part ◽  
Ultra Performance Liquid Chromatography ◽  
Total Phenol Content ◽  
Phenol Content ◽  
Polyphenol Content ◽  
Reference Information ◽  
Phenolic Components ◽  
Early Maturing ◽  
Litchi Fruit ◽  
First Time

Litchi is an important fruit cultivated in tropical and subtropical areas with high nutritious and delicious flavor and the pulp is the main part of the fruit consumed. Previous studies found that litchi had high total phenol content and antioxidant activity, but most of them focused on the identification of single or a few phenolic components with a low throughput test, and the metabolic differences of cultivars are still unknown to a some extent. In this study we used widely targeted metabolome based on ultra-performance liquid chromatography coupled with mass spectrometry (UPLC-MS/MS) to analyze the polyphenol metabolites of five different genotypes of mature litchi fruit. A total of 126 polyphenol metabolites in eight categories were identified to reveal the composition and differences of polyphenol; 15 common differential metabolites and 20 specific differential metabolites to each cultivar were found for the first time. The results infer that flavonoids, flavonols, hydroxycinnamoyls and catechins are the main polyphenol metabolites of litchi pulp. Cluster analysis showed that there were three groups of polyphenols from high to low; early maturing Feizhixiao is a kind of high polyphenol content cultivars, especially in catechins, anthocyanins, flavonols, quinic acids and hydroxycinnamoyls. The polyphenols in the flesh of mature litchi are rich, and there are significant differences among cultivars; there was a level of correlation between the contents of phenolics and the maturity of litchi cultivars; the content of phenolics in early maturing litchi cultivars appeared higher than those of mid- to late-maturing cultivars. This experiment will provide significant reference information for cultivation, breeding, processing and consumption.

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