COLLOIDS AND SURFACES B-BIOINTERFACES
·
2022
·
IF 5.999
Zidan Luo,Mengfei Tian,Naveed Ahmad,Wu Qiu,Yu Zhang,Chunying Li,Chunjian Zhao
In this study, a switchable temperature-responsive ionic liquid-based surfactant-free microemulsion (TRIL-SFME) for extraction and in-situ separation of hydrophilic and lipophilic compounds from Camptotheca acuminata was firstly developed and systematically characterized. This TRIL-SFME was obtained using 1-hexyl-3-methylimidazolium tetrafluoroborate ([HMIM][BF 4 ]), 1,2-propanediol and H 2 O. The prepared TRIL-SFME presented low viscosity and rapid response to temperature. Firstly, the effect of temperatures on TRIL-SFME phase behavior was studied followed by determination of effect of liquid/solid ratio and extraction time on the extraction yields of the targeted compounds. The TRIL-SFME demulsified rapidly by thermal stimulus, resulting in in-situ separation and enrichment of compounds with varying polarity. The results of present study revealed that TRIL-SFME had higher extraction yields (1.50–5.79 folds) compared to traditional solvents and individual components of TRIL-SFME. Besides, in-situ separation and enrichment of hydrophilic compounds (phenolic acids) and lipophilic compounds (alkaloids) was accomplished in short time (within 3 min) by cooling the system to 4 ℃. Furthermore, the mesoscopic behavior between TRIL-SFME and targeted compounds was simulated by dissipative particle dynamics (DPD) to explore the extraction mechanism for the first time. The results illustrated the formation of W/IL structure of TRIL-SFME and clarified solubilization mechanism of TRIL-SFME system for targeted compounds, which is related to its special "water pool" structure. This novel and switchable TRIL-SFME is an environmentally friendly and promising alternative to simultaneously extract, in-situ separate and enrich the natural active compounds with different polarity from plant matrices.
研究领域:
植物化学
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分离科学
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药物化学
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产品关联
DOI
PubMed
高影响因子
SEPARATION AND PURIFICATION TECHNOLOGY
·
2024
·
IF 8.1
Feng-Ying Wu,Yan Cheng,Xin-Yue Yuan,Qi-Lei Sun,Fu-Min Xue
The study investigated the extraction of alkaloids and glycosides from the Camptotheca acuminata Decne using deep eutectic solvent (DES). 18 types of deep eutectic solvents (DESs) were prepared, and it was found that the extraction performance of choline chloride (ChCl)-formic acid (FA) was optimal, surpassing traditional solvents such as methanol/70 % methanol. In comparison to methanol, the extracted amount of compounds by DES was 2–3 times higher. The extraction processes involving the molar ratio of ChCl-FA, pH, DES/H 2 O mass ratio, solid/liquid ratio, as well as ultrasonic power were optimized. A mathematical model for solid/liquid extraction kinetics from Camptotheca acuminata Decne was developed. The extraction mechanism was investigated using scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), and 1 H nuclear magnetic resonance( 1 H NMR). The results revealed that the DES caused dissociation in Camptotheca acuminata Decne and formed hydrogen bonds with Camptothecin (CPT). Meanwhile, density functional theory (DFT) calculations verified that FA-based exhibited the highest extracted amount for CPT. In addition, this study investigated the recovery rate of DES, and the results showed that after 10 cycles, the DES system remained effective for the extraction of alkaloids and glycosides.
研究领域:
药学
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分析化学
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植物化学
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提取技术
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产品关联
DOI
高影响因子
RSC Advances
·
2019
·Vol. 9
·期 17
·9449-9456
·
IF 3.049
Yuhua Zhang,Jiayi Jiang,Ningbo Qin,Qian Zhang,Chunyan Yan
Cambial meristematic cell (CMC) suspension cultures were investigated as a new biotransformation system for the first time. Four 4-methylcoumarins substrates were transformed by CMCs of Camptotheca acuminata into four corresponding products, including 4,8-dimethylcoumarin-7-O-β-D-glucopyranoside (I-1), 4,7-dimethylcoumarin-6-O-β-D-glucopyranoside (II-1), 6-hydroxy-7-methoxyl-4- methylcoumarin (III-1), and 4,7-dimethylcoumarin-5-O-β-D-glucopyranoside (IV-1), of which I-1, II-1, and IV-1 were new compounds. In addition, the biotransformation time and the amount of substrate were investigated to compare the biotransformation rate and optimize the biotransformation conditions of the four substrates in C. acuminata CMCs suspension cultures. The results suggested C. acuminata CMCs were able to select glycosylate phenolic hydroxyl groups of 4-methylcoumarins I, II, and IV, with high regio- and stereoselectivity, but no corresponding glycoside of any phenolic hydroxyl group of compound III was detected. Simultaneously, the result also showed that the C. acuminata CMCs were able to transform the 7-hydroxy groups of substrate III to its corresponding methylated products. Furthermore, the monoamine oxidase (MAO) inhibition activities of biotransformed products were evaluated, and the data showed that all the products possessed good MAO inhibition activities in vitro. In conclusion, C. acuminata CMCs could be applied to glycosylation biotransformation as a novel plant-based system due to the successful application of bioconversion of exogenous coumarins.
研究领域:
药理学
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植物生物技术
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生物化学
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产品关联
DOI
PubMed
高影响因子
Frontiers in Plant Science
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2022
·
IF 6.627
Qiao Chong,Chen Fei,Liu Zhan,Huang Tianfang,Li Wei,Zhang Guolin,Luo Yinggang
Tryptophan decarboxylases (TDCs) are a group of pyridoxal 5′-phosphate-dependent enzymes involved in the enzymatic conversion of tryptophan into tryptamine, a critical biogenic amine. We herein mined and cloned a TDC-encoding gene, CaTDC3, from camptothecin-producing plant Camptotheca acuminata. The intact CaTDC3 was heterologously overexpressed in Escherichia coli and the recombinant CaTDC3 was purified to homogeneity. High-performance liquid chromatography (HPLC)-diode array detector (DAD) and high resolution mass spectrometry (HRMS) data analyses of the CaTDC3-catalyzed reaction mixture confirmed the catalytically decarboxylative activity of CaTDC3. CaTDC3 shows strict stereoselectivity for L-tryptophan. Homology modeling and molecular docking implied CaTDC3’s recognition of L-tryptophan derivatives and analogs. Substrate scope investigations revealed that the appropriate substituent groups on the indole ring, i.e., hydroxylated and halogenated L-tryptophans, could be recognized by CaTDC3 and the decarboxylation reactions generated the corresponding tryptamines. The Cβ -methyl-L-tryptophans were decarboxylated by CaTDC3 efficiently. 1-Thio-L-tryptophan, the NH group of the indole ring replaced by an S atom, could be decarboxylated by CaTDC3. CaTDC3 catalyzed the decarboxylation of 7-aza-L-tryptophan, an N displacement of the C on the aromatic ring, to afford 7-aza-tryptamine. L-Kynurenine, an L-tryptophan degradation product, could be decarboxylated by CaTDC3. The present works uncover a catalytically promiscuous TDC and the TDC is a versatile decarboxylase in synthetic biology for specialized pharmaceutically important substances.
研究领域:
生物化学
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酶学
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药理学
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合成生物学
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产品关联
DOI
PubMed
高影响因子
SEPARATION AND PURIFICATION TECHNOLOGY
·
2019
·
IF 5.107
Ting Wang,Pengfei Li,Yao Sun,Xiaomei Song,Hao Li,Liting Qin,Juying Zhou,Qin Huang,Fuhou Lei
In this work, camptothecin (CPT) molecularly imprinted polymer (MIP) microspheres were prepared via membrane emulsification-suspension polymerization using ethylene glycol maleic rosinate acrylate as a crosslinker, acrylic acid as a functional monomer, and CPT as a template molecule. The MIPs were characterized by scanning electron microscopy, laser granulometry, nitrogen sorption porosimetry, and thermogravimetric analysis. The results indicated that the MIPs had a regular spherical shape with porous surfaces and particle sizes mainly ranging from 3 to 5 μm. The surface areas of the MIPs and non-molecularly imprinted polymer (NIP) microspheres were 89.44 and 86.91 m 2 g −1 , respectively, and their respective average pore sizes were 11.42 and 10.84 nm. Furthermore, the MIPs and NIPs exhibited excellent thermal stabilities. The HPLC columns prepared with the MIPs and NIPs as the chromatographic stationary phase showed good fluidity. The effect of the MIP column on CPT was evaluated with HPLC, and the selectivity and separation performance of the MIP and NIP columns for CPT and 10-hydroxycamptothecin were evaluated. The chromatographic thermodynamics and separation mechanism were also studied. Finally, the MIP column was successfully applied to the separation and purification of CPT from an extract of Camptotheca acuminata fruit, and the reusability of the MIP column was also investigated.
研究领域:
药学
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分离科学
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材料科学
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产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
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2024
·
IF 7.7
Xiang Pu,Jiahua Zhang,Jinwei He,Zhihui Ai,Xiaoxue He,Xiaojun Zhou,Shiyuan Tong,Xinyue Dai,Qiqi Wu,Jiayu Hu,Jingshu He,Hanguang Wang,Wei Wang,Jinqiu Liao,Li Zhang
The biosynthetic route for flavonol in Camptotheca acuminata has been recently elucidated from a chemical point of view. However, the genes involved in flavonol methylation remain unclear. It is a critical step for fully uncovering the flavonol metabolism in this ancient plant. In this study, the multi-omics resource of this plant was utilized to perform flavonol O -methyltransferase-oriented mining and screening. Two genes, CaFOMT1 and CaFOMT2 are identified, and their recombinant CaFOMT proteins are purified to homogeneity. CaFOMT1 exhibits strict substrate and catalytic position specificity for quercetin, and selectively methylates only the 4′-OH group. CaFOMT2 possesses sequential O -methyltransferase activity for the 4′-OH and 7-OH of quercetin. These CaFOMT genes are enriched in the leaf and root tissues. The catalytic dyad and critical substrate-binding sites of the CaFOMTs are determined by molecular docking and further verified through site-mutation experiments. PHE181 and MET185 are designated as the critical sites for flavonol substrate selectivity. Genomic environment analysis indicates that CaFOMT s evolved independently and that their ancestral genes are different from that of the known Ca10OMT . This study provides molecular insights into the substrate-binding pockets of two new CaFOMTs responsible for flavonol metabolism in C. acuminata .
研究领域:
植物生物化学
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分子生物学
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植物化学
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
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2026
·
IF 8.7
Linan Sun,Ming Qu,Jingru Zhao,Chengbo Gu,Xue Wu,Han Yang,Yujie Fu
CPT-enriching molecularly imprinted materials have been developed. • CCS-Si and MIP-CPT exhibit high selectivity for CPT. • The efficiency of the molecularly imprinted extraction column can reach 89.45%. Camptothecin (CPT), a potent anticancer quinoline alkaloid derived from plant resources, is conventionally purified through multi-step processes with low selectivity, high solvent consumption and unsatisfactory recovery. In this study, a novel bio-based surface-imprinted adsorbent (CCS-Si&MIP-CPT) was rationally designed and fabricated using porous cellulose-silica hybrid microspheres as the support matrix, with CPT as the template molecule and methacrylic acid as the functional monomer. The physicochemical structure of the as-prepared material was fully characterized, and its adsorption kinetics, isotherms, selective recognition mechanism and reusability were systematically investigated. Furthermore, the material was applied as a solid-phase extraction (SPE) filler for the purification of CPT from crude camptotheca seed extracts, and its performance was benchmarked against established purification methods. The results show that the adsorption behaviour of CCS-Si&MIP-CPT toward CPT is in good agreement with the Langmuir isotherm and the pseudo-second-order kinetic model. Combined with molecular structure comparison of CPT analogs, the selective recognition mechanism was comprehensively elucidated from three perspectives: hydrogen-bonding functional group matching, steric hindrance effect of substituents, and complementarity of molecular size and overall shape. The renewable carrier design and its cyclic stability not only show potential for application in green separation technologies for natural medicine development, but also provide a theoretical foundation for the high-value utilization of plant resources.
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产品关联
DOI
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2025
·
IF 6.2
Tengteng Yang,Wenquan Wang,Xiaoli Wang,Qiaowei Miao,Junhai Liu,Hansheng Wang,Lun Liu,Xiaohui Ji,Chenyang Wei
Camptothecin (CPT) has significant biological activity and has been extensively studied. This study established an efficient and green ultrasonic-assisted deep eutectic solvent (UAE-DES) and combined it with macroporous resin purification technology to extract and purify CPT and 10-hydroxycamptothecin (HCPT) from Camptotheca acuminata fruit. In total, 33 natural DES were prepared, among which choline chloride-1,4-butanediol was the most effective. The single-factor and response surface optimization extraction experiments were carried out to determine optimal conditions as follows: ultrasonic time = 27 min, solid-liquid ratio = 1:35 g/mL, ultrasonic temperature = 70 °C, DES moisture content, = 29 %, and total extraction rate = 0.1318 %. Furthermore, the scanning electron microscopy revealed that the UAE-DES treatment significantly disrupted the cell-wall structure of C. acuminata fruits, promoting the release of the target constituents. Moreover, AB-8-type macroporous resin was employed to optimize adsorption and desorption, which optimized 63.4 % and 77.3 % adsorption and desorption of CPT and HCPT, respectively. Density functional theory (DFT) was employed for assessing electrostatic potential (ESP), complexation energy, and reduced density gradient (RDG), to identify the non-covalent interactions between DES, conventional solvent ethanol, and CPT-like compounds during the extraction process. This study comprehensively explained the extraction mechanism and confirmed that DES had better extraction potential and good biocompatibility. These findings provide a theoretical basis and technical support for the green and efficient extraction and purification of CPT-like compounds.
研究领域:
天然产物化学
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药物分析
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植物药学
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绿色化学
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分子互作机制
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产品关联
DOI
高影响因子
RSC Advances
·
2017
·Vol. 7
·期 20
·12185-12193
·
IF 3.108
Yuhua Zhang,Keming Jiang,Degang Qing,Bing Huang,Jiayi Jiang,Shumei Wang,Chunyan Yan
Camptotheca acuminata Decne (Nyssaceae) is a major natural source of the anticancer drug camptothecin (CPT) and its derivatives. The leaves and stems are two of the main regions that accumulate CPT in C. acuminata. In this study, we successfully isolated cambial meristematic cells (CMCs) and dedifferentiated cells (DDCs) from C. acuminata stems and leaves, identified their characteristic features using micrograph analysis, and assessed their hypersensitivity to γ-irradiation and zeocin. The growth and kinetics curves of CMCs and DDCs were also studied. Furthermore, the accumulation of CPT and 10-hydroxycamptothecin (HCPT)—a more potent and less toxic CPT derivative—was assessed by liquid chromatography, and the transcriptional levels of nine genes encoding key enzymes involved in CPT and HCPT biosynthesis was assessed using quantitative real-time polymerase chain reaction (PCR) in CMCs and DDCs. The results showed that CMCs induced were particularly hypersensitive to γ-irradiation and zeocin and presented with abundant and small vacuoles, whereas DDCs were not. The above morphological and physiological characteristics of CMCs were consistent with previous reports. B5 medium was determined as the best growth medium for CMCs and DDCs. The accumulation of CPT and HCPT was higher in CMCs than DDCs, and the expression of IPI, G10H, ASA1, TSB, TDC1, TDC2, and STR was significantly upregulated in CMCs compared with DDCs; HMGR2 and HMGR3 were downregulated in CMCs. We speculate that the high accumulation of CPT and HCPT in CMCs was due to the upregulation of these seven genes.
研究领域:
药理学
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植物生物学
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分子生物学
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产品关联
DOI
高影响因子
SEPARATION AND PURIFICATION TECHNOLOGY
·
2018
·
IF 3.927
Guoqiang Cui,Xuebing Yang,Tingting Liu,Zaizhi Liu,Lei Yang
An efficient approach for enzyme-enhanced extraction using an ionic liquid solution (ILEEE) of the major alkaloidal components camptothecin (CPT) and 10-hydroxycamptothecin (HCPT) from the samara of Camptotheca acuminata is presented. The enzyme pretreatment in an aqueous ionic liquid (IL) media was used for the enhancement of extraction yield. The activity of hemicellulase was investigated in various ILs with imidazolium-based cations ([C 2 MIM] + , [C 4 MIM] + , [C 6 MIM] + , [C 8 MIM] + , [C 10 MIM] + ) and anions (Br − , Cl − , Ac − , HSO 4 − , NO 3 − ). The optimal ionic liquid for the hemicellulase extraction process was found to be a 0.75 M [C 8 MIM]Br aqueous solution. Single factor experiments and Box–Behnken design found the optimal operational parameters for ILEEE to be an incubation temperature of 40 °C, incubation time of 12 h, extraction phase of pH 4, liquid-solid ratio of 30 mL/g, 0.75 M [C 8 MIM]Br and a hemicellulase concentration of 0.441 mg/mL. Under these optimized extraction conditions, the total yield of CPT and HCPT was 1043 ± 51.2 μg/g. SEM images of the samples revealed that hemicellulases hydrolyze the cell wall, leading to structure breakdown, which enabled [C 8 MIM]Br to have a high dissolving power for the targeted components. These factors are the main causes for the increasing in the total yield of the CPT and HCPT when using the ILEEE extraction method.
研究领域:
药学
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化学工程
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生物技术
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DOI
高影响因子
MOLECULES
·
2019
·Vol. 24
·期 4
·815
·
IF 3.06
Zhaoxia Jin,Ruyi Wan,Ruxue Yan,Yingying Su,Honglan Huang,Lihan Zi,Fang Yu
Camptothecin (CPT) has strong antitumor activity and is used as an anticancer therapeutic agent. To better understand and decipher the pathway of CPT biosynthesis inCamptotheca acuminata, the main purpose here was focused on creating an effective extraction strategy for a rich intermediate metabolite profile. In the present study, a 70% aqueous acetonitrile was verified as an optimal extraction solvent for microwave-assisted extraction (MAE) of metabolites by spiking experiments. Based on multi-objective optimization, the best extraction conditions of a solid-liquid ratio of 1:20, microwave power of 230 W, and a time of 4 min were achieved using a full factorial 34experimental design. Crude extracts obtained from the shoot apex ofC. acuminatausing MAE have been qualitatively profiled by high-performance liquid chromatography coupled with linear ion trap quadrupole-orbitrap mass spectrometry (HPLC-LTQ-Orbitrap-MS/MS) and a HPLC triple quadrupole-MS (HPLC-TSQ-MS) analysis was conducted for their metabolite content in different tissues. CPT, and ten related metabolites and their isomers, including tryptamine, loganic acid, secologanic acid, strictosidinic acid, strictosamide, strictosamide epoxide, strictosamide diol, strictosamide ketolactam, pumiloside, and deoxypumiloside, were detected and tentatively identified. Scanning electron microscopy (SEM) imaging of the shoot apex demonstrated that severe cell disruption was evident after intensified extraction processes. The study showed the difference of metabolite profiles and the enhancement of metabolite content after microwave-pretreated techniques, and the established MAE procedure is an effective methodology to preserve valuable metabolite compounds for analysis.Keywords:microwave assisted extraction;Taguchi experimental design;metabolites;camptothecin;HPLC-LTQ-MS/MS
研究领域:
植物化学
·
药物化学
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分析化学
✓ 已验证
DOI
PubMed
高影响因子
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