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PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA · 2022 ·Vol. 120 ·期 1 ·e2209339120 · IF 12.779

Elucidation of the 1-phenethylisoquinoline pathway from an endemic conifer Cephalotaxus hainanensis

Fei Qiao,Yuedong He,Yuhao Zhang,Xuefei Jiang,Hanqing Cong,Zhiming Wang,Huapeng Sun,Yibei Xiao,Yucheng Zhao,Peter Nick

Cephalotaxines harbor great medical potential, but their natural source, the endemic conifer Cephalotaxus is highly endangered, creating a conflict between biotechnological valorization and preservation of biodiversity. Here, we construct the whole biosynthetic pathway to the 1-phenethylisoquinoline scaffold, as first committed compound for phenylethylisoquinoline alkaloids (PIAs), combining metabolic modeling, and transcriptome mining of Cephalotaxus hainanensis to infer the biosynthesis for PIA precursor. We identify a novel protein, ChPSS, driving the Pictet–Spengler condensation and show that this enzyme represents the branching point where PIA biosynthesis diverges from the concurrent benzylisoquinoline-alkaloids pathway. We also pinpoint ChDBR as crucial step to form 4-hydroxydihydrocinnamaldehyde diverging from lignin biosynthesis. The elucidation of the early PIA pathway represents an important step toward microbe-based production of these pharmaceutically important alkaloids resolving the conflict between biotechnology and preservation of biodiversity.

研究领域: 植物生物化学 · 药用植物学 · 生物技术 · 保护生物学
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ELECTROCHEMISTRY COMMUNICATIONS · 2019 · IF 4.197

Highly efficient electrochemiluminescence of quinoline and isoquinoline in aqueous solution

Xiangxiang Qin,Xia Xu,Jing Lu,Yinggui Zhu

This paper reports for the first time the strong cathodic electrochemiluminescence (ECL) behavior of quinoline, isoquinoline and their derivatives in aqueous solution with K 2 S 2 O 8 as coreactant. The effects of K 2 S 2 O 8 concentration, pH and scan rate on the ECL intensity have been studied in detail. Calculations of the HOMO-LUMO energy gap for the ECL reaction indicated that isoquinoline is more likely to produce an excited state radical ion than quinoline. The effects of different functional groups on the ECL of isoquinoline were then compared and a possible ECL reaction mechanism was discussed. This work provides a simple and sensitive ECL method for the detection of quinoline and isoquinoline, which are important drug intermediates.

CAS / MDL: 27655-40-9 486-73-7
研究领域: 分析化学 · 药物化学
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APPLIED CATALYSIS A-GENERAL · 2018 · IF 4.521

Highly active and recyclable Pt nanocatalyst for hydrogenation of quinolines and isoquinolines

Xiuru Xue,Min Zeng,Yanhua Wang

Thermoregulated phase-transfer Pt nanocatalyst was shown to be highly active, selective and recyclable in the hydrogenation of quinolines and isoquinolines. The catalyst could be easily separated from the product by simple phase separation and directly reused in the next cycle without evident loss in catalytic activity and selectivity, even after ten recycles. Importantly, for quinoline, the TON of 10,474 is the highest value ever reported among Pt catalysts. More remarkably, for isoquinoline, the TON of 5340 is far ahead of the highest record among transition metal catalysts.

研究领域: 催化化学 · 材料科学 · 有机合成
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2022 · IF 3.119

Solubility Data, Modeling, and Solvent Effect of 8-Isoquinolinamine in Four Mixed Solvents and Ten Monosolvents from 278.15 to 323.15 K

Renjie Xu,Ganbing Yao

The equilibrium solubility of 8-isoquinolinamine in methanol, ethanol, n-propanol, isopropanol, N,N-dimethylformamide (DMF), acetonitrile, acetone, propylene glycol (PG), ethylene glycol (EG), and water, and aqueous mixtures of methanol/ethanol/n-propanol/isopropanol plus water was experimentally measured by the isothermal saturation method at 278.15–323.15 K under 101.2 kPa. The mole fractions of 8-isoquinolinamine in monosolvents were obtained to be maximum in neat DMF. For the four binary mixed solvent systems, the amount of 8-isoquinolinamine dissolved in n-propanol + water is more than that in the other three systems. The mole fractions of 8-isoquinolinamine in pure solvents were correlated using the Apelblat model, van’t Hoff model, and Wilson model, and the calculated value of the Apelblat model was the closest to the experimental value. The Jouyban–Acree model, modified Apelblat–Jouyban–Acree model, and van’t Hoff–Jouyban–Acree model were applied to calculate the solubility of 8-isoquinolinamine in the four solvent mixtures. The feedback obtained by comparing the experimental data with the calculated data is that the calculated data from the Jouyban–Acree model was relatively close to the experimental results. Solvent effects as a powerful tool can be used to estimate interactions at the molecular level, and the results showed that solvent–solvent intermolecular interactions contribute to dissolution. van’t Hoff plots are adopted as a method to show the relationship between ln(x) and 1/T.

研究领域: 化学 · 药物科学
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CLINICAL AND EXPERIMENTAL PHARMACOLOGY AND PHYSIOLOGY · 2025 ·Vol. 52 ·期 4 ·e70033 · IF 2.5

Norisoboldine Alleviates Isoproterenol-Induced Myocardial Ischemic Injury via the TLR4–MyD88-Dependent NF-κB Activation Pathway and Modulation of L-Type Calcium Channels

Xin Zhang,Xinliu Wang,Yuanyuan Wang,Xingyou Ma,Yunyun Geng,Shuxian Zang,Ziyun Ban,Yugai Jia,Yonggang Gao

Norisoboldine (NIB) displays beneficial effects on cardiovascular diseases, although its protective role and underlying mechanisms in myocardial ischemia (MI) injury remain elusive. The aim of this study is to explore the potential cardioprotective mechanism of NIB on MI injury caused by isoproterenol (ISO). We administered NIB to SD rats at 20 and 40 mg/kg daily for 7 days in this study; this was followed by an ISO injection to induce MI injury. Parameters such as electrocardiogram readings, heart rate, serum concentrations of creatine kinase (CK) and creatine kinase-MB (CK-MB), levels of inflammatory markers, some histopathological assessments and oxidative stress markers were evaluated. We conducted Western blot analyses to evaluate protein expression related to apoptosis and the TLR4–MyD88-mediated NF-κB activation pathway. The L-type Ca 2+ current (ICa-L) and contraction of isolated ventricular cells from rats were identified using patch-clamp methods and the IonOptix detection system. The treatment with NIB resulted in improvements in heart rate and ST-segment changes, a reduction in CK and CK-MB levels, the restoration of superoxide dismutase, catalase and glutathione levels and a decrease in malondialdehyde accumulation. Furthermore, NIB reduced the expression of inflammatory markers, lowered Ca 2+ levels and reactive oxygen species production and improved myocardial tissue morphology. It also countered ISO-induced alterations in apoptosis and the TLR4–MyD88-dependent NF-κB activation pathway. Additionally, NIB considerably attenuated ICa-L and reduced the contractile function of cardiomyocytes. These results suggest that NIB effectively mitigates ISO-induced MI injury through anti-inflammatory, antioxidative, and anti-apoptotic mechanisms, potentially involving the TLR4–MyD88-dependent NF-κB activation pathway and calcium balance.

CAS / MDL: 67-63-0
研究领域: 药理学 · 心血管疾病 · 分子生物学
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JOURNAL OF ORGANIC CHEMISTRY · 2022 · IF 4.198

Rh(III)-Catalyzed One-Pot Three-Component Diannulation of Benzils, Ammonium Acetate, and Alkynes to Build 1,1′-Biisoquinolines

Shihai Lv,Ya-Nan Tian,Yanyan Yang,Chaoying Wen,Shiqing Li

An efficient one-pot synthesis of 1,1′-biisoquinolines by a three-component reaction of commercially available raw materials (benzils, NH4OAc, and alkynes) is disclosed. This complicated reaction involves in situ diimine formation via benzil-NH4OAc condensation, Rh(III)-catalyzed 2-fold imine-directed C–H activation, and annulation with alkynes. Both symmetric and unsymmetric 1,1′-biisoquinolines could be assembled in moderate to high yields. The reaction mechanism is supported through ESI-MS, in which Cp*ClRh+, Cp*(OAc)Rh+, Cp*(OPiv)Rh+, and two rhodacycle intermediates are successfully detected to explain the evolution of rhodium species.

研究领域: 有机化学 · 合成化学
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Science China-Chemistry · 2019 ·Vol. 63 ·期 1 ·28-34 · IF 6.085

Integrating photocatalytic reduction of CO2 with selective oxidation of tetrahydroisoquinoline over InP–In2O3 Z-scheme p-n junction

Zhao Bohang,Huang Yi,Liu Dali,Yu Yifu,Zhang Bin

The development of a facile strategy to construct stable hierarchal porous heterogeneous photocatalysts remains a great challenge for efficient CO 2 reduction. Additionally, hole-trapping sacrificial agents (e.g., triethanolamine, triethylamine, and methanol) are mostly necessary, which produce useless chemicals, and thus cause costs/environmental concerns. Therefore, utilizing oxidation ability of holes to develop an alternative photooxidation reaction to produce value-added chemicals, especially coupled with CO 2 photoreduction, is highly desirable. Here, an in situ partial phosphating method of In 2 O 3 is reported for synthesizing InP–In 2 O 3 p-n junction. A highly selective photooxidation of tetrahydroisoquinoline (THIQ) into value-added dihydroisoquinoline (DHIQ) is to replace the hole driven oxidation of typical sacrificial agents. Meanwhile, the photoelectrons of InP–In 2 O 3 p-n junction can induce the efficient photoreduction of CO 2 to CO with high selectivity and stability. The evolution rates of DHIQ and CO are 2 and 3.8 times higher than those of the corresponding In 2 O 3 n-type precursor, respectively. In situ irradiated X-ray photoelectron spectroscopy and electron spin resonance are utilized to confirm that the direct Z-scheme mechanism of InP–In 2 O 3 p-n junction accelerate the efficient separation of photocarriers.

研究领域: 材料科学 · 环境科学
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FITOTERAPIA · 2021 · IF 2.882

Two new isoquinoline alkaloids from Cryptocarya wrayi and their biological activities

Yun-Lai Liu,Yong Wang,Xiao-Ru He,Li-She Gan,Fan Xu,Yun-Jing Xu,Xiao-Ning Wang,Tao Shen,Zhi-Wang Zhou

Two new isoquinoline alkaloids , cryptowrayines A ( 1 ) and B ( 2 ), along with one known pavine alkaloid (-)-12-hydroxyeschscholtzidine ( 3 ), were isolated from the twigs of Cryptocarya wrayi . The structures of new compounds were elucidated by extensive spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Both compounds 1 and 2 exhibited moderate quinone reductase inducing activity in Hepa 1c1c7 cells.

CAS / MDL: 56180-94-0
研究领域: 植物化学 · 药理学
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ENVIRONMENTAL RESEARCH · 2021 · IF 6.498

Dual light-driven p-ZnFe2O4/n-TiO2 catalyst: Benzene-breaking reaction for malachite green

Jiayi Li,Ying Huang,Minhua Su,Yuying Xie,Diyun Chen

Heterocyclic aromatic compounds such as malachite green can cause immense harm to the environment and mankind because of their toxic bio-accumulation and insufficient biodegradation. ZnFe 2 O 4 /TiO 2 (ZF-T) has attracted attentions as a visible-light-driven catalyst because it can break and mineralize benzene through photolysis. Compared with TiO 2 , which photodegrades only 53.5% malachite green, anatase TiO 2 loaded with ZnFe 2 O 4 has greater photocatalytic activity and can degrade up to 90.1% malachite green. Furthermore, a photocatalytic efficiency above 80% can be obtained through five consecutive cycles with a duration of 4 h. In this study, ZF-T was characterized, and its photolytic parameters, including dosage, pH, time, and ionic strength, were optimized. The photolytic products of malachite green were analyzed by ultraviolet–visible spectroscopy and liquid chromatography-mass spectrometry, which confirmed that ZF-T can drive visible light to produce •O 2 − and H + free radicals that can efficiently degrade heterocyclic aromatic hydrocarbons and cleave benzene rings. These outcomes deepen our understanding of the development and applications of visible-light-driven ZF-T composites in the field of wastewater purification.

研究领域: 环境科学 · 材料科学
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Methods and Applications in Fluorescence · 2022 ·Vol. 10 ·期 3 ·035004 · IF 3.849

A novel AIEE active anti-B18H22 derivative-based Cu2+ and Fe3+ fluorescence off-on-off sensor

Linli Xiong,Yong Zheng,Haibo Wang,Jiangyang Yan,Xuguang Huang,Hongyun Meng,Chunhua Tan

A novel fluorescence sensor for successive detection of Cu2+ and Fe3+ based on anti-B18H22 derivative which possesses 5-hydroxyisoquinoline as an ionophore was synthesized via a one-pot and its structure and photophysical properties were characterized by NMR, HRMS, FTIR, UV–vis, PL and theoretical calculation. The fluorophore displays two emission peaks at 460 nm and 670 nm in THF solution coming from the emission of the locally excited state and intramolecular charge transfer fluorescence, respectively. The complex exhibited obvious aggregation-induced emission enhancement (AIEE) characteristics in THF/H2O solution by increasing the aqueous concentration from 70% to 95%. The AIEE molecules showed a high selectivity towards Cu2+ over other metal ions by forming a 2:1 metal-to-ligand complex in THF/H2O (fw = 20%) solution, the fluorescence intensity increased as a linear function of the Cu2+ concentration at 460 nm due to the inhibition of PET effect. The fluorescent emission was quenched linearly by the addition of Fe3+, which provides a method for successive determination of Cu2+ and Fe3+ based on 'off-on-off' fluorescence of the fluorescent. The detection limit of Cu2+ and Fe3+ was 5.7 × 10−6 M and 7.2 × 10−5 M respectively. Morever, a rapid identification of Cu2+ in the aqueous solution by naked eyes can be realized. In addition, the molecules were pH-sensitive, the fluorescence quenching can be observed in strongly alkaline environment. The method has been applied to the determination of copper ions in water samples with satisfactory results.

研究领域: 化学 · 材料科学
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FOOD CHEMISTRY · 2024 · IF 8.5

Exploring the roles of excess amino acids, creatine, creatinine, and glucose in the formation of heterocyclic aromatic amines by UPLC-MS/MS

Haolin Zhang,Xiaomei Lv,Weiming Su,Bing-Huei Chen,Yu-Wen Lai,Ruiwei Xie,Qiuyi Lin,Lei Chen,Hui Cao

The prevention and control of heterocyclic aromatic amines (HAA) formation to mitigate of potential risks to humans, can be achieved by targeting their precursors. In this study, the detailed roles of individual and excess component (20 common α-amino acids, creatine, creatinine, and glucose) on HAA formation in roasted beef patties were examined using UPLC-MS/MS. The results confirmed the reported classical precursors of HAAs. Some components regulated the competitive production of Norharman and Harman. Glycine (Gly) and glucose favored Norharman formation, while cysteine (Cys) and phenylalanine (Phe) for Harman. Serine (Ser) and threonine (Thr) were identified as potential precursors for IQx-type HAAs. Interestingly, methionine (Met), Gly, Thr, Cys, alanine (Ala), and Ser were revealed as more targeted underlying precursors for 1,6-DMIP and 1,5,6-TMIP, and the formation mechanism was inferred. Furthermore, Pro, Leu, His, Ile, Lys and Asp were considered as great inhibitors for HAAs.

CAS / MDL: 50-99-7
研究领域: 食品科学 · 分析化学 · 毒理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Analytical Methods · 2025 · IF 2.6

Supramolecular solvent-based ultrasound-assisted extraction of fangchinoline and tetrandrine from the roots of Stephaniae tetrandrae

Yingzhen Wang,Bingyue Cao,Shanshan Shi,Shulin Gao,Dandan Ge

A supramolecular solvent (SUPRAS) based ultrasound-assisted extraction method was developed for the extraction of fangchinoline and tetrandrine from Radix Stephaniae tetrandrae. SUPRASs were prepared in aqueous solutions containing hexafluorobutanol (HFB) and alkanols for the first time. HFB was used as a coacervation agent and density-regulating agent for the SUPRAS preparation. The biosurfactants, namely hexanol, octanol, and decanol were selected as the amphiphiles. The possible mechanism of the new SUPRAS formation was studied. The hydrogen-bond and hydrophobic interactions between HFB and alkanols are the main driving forces for the new SUPRAS formation. The crucial parameters influencing the extraction yields of FAN and TET, such as type and content of amphiphile, type and content of coacervation agent, volume of SUPRAS, ultrasound time, and extraction temperature were investigated and optimized. HFB-hexanol SUPRAS was found to be the most effective extraction solvent for the extraction of fangchinoline and tetrandrine from Stephaniae tetrandrae. Under the optimized conditions, HFB-hexanol SUPRAS showed extraction yields of 7.11 and 13.89 mg g-1 for FAN and TET, respectively. The values were higher than those of obtained with other extraction methods. The developed method has a great potential for extracting alkaloids from natural plant materials.

研究领域: 植物化学 · 分析化学
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