MOLECULES
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2023
·Vol. 28
·期 11
·4503
·
IF 4.6
Lili Shi,Ziyu Cui,Wei Liu
β-carbolines (harman and norharman) are potentially mutagenic and have been reported in some vegetable oils. Sesame seed oil is obtained from roasted sesame seeds. During sesame oil processing, roasting is the key procedure to aroma enhancement, in which β-carbolines are produced. Pressed sesame seed oils cover most market share, while leaching solvents are used to extract oils from the pressed sesame cake to improve the utilization of the raw materials. β-carbolines are nonpolar heterocyclic aromatic amines with good solubility in leaching solvents (n-hexane); therefore, the β-carbolines in sesame cake migrated to the leaching sesame seed oil. The refining procedures are indispensable for leaching sesame seed oil, in which some small molecules can be reduced. Thus, the critical aim is to evaluate the changes in β-carboline content during the refining of leaching sesame seed oil and the key process steps for the removal of β-carbolines. In this work, the levels of β-carbolines (harman and norharman) in sesame seed oil during chemical refining processes (degumming, deacidification, bleaching and deodorization) have been determined using solid phase extraction and high performance liquid chromatography-mass spectrometry (LC-MS). The results indicated that in the entire refining process, the levels of total β-carbolines greatly decreased, and the adsorption decolorization was the most effective process in reducing β-carbolines, which might be related to the adsorbent used in the decolorization process. In addition, the effects of adsorbent type, adsorbent dosage and blended adsorbent on β-carbolines in sesame seed oil during the decolorization process were investigated. It was concluded that oil refining can not only improve the quality of sesame seed oil, but also reduce most of the harmful β-carbolines.Keywords:adsorbent;β-carbolines;harman;norharman;sesame seed oil
研究领域:
食品科学
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化学工程
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PubMed
高影响因子
CHIRALITY
·
2013
·Vol. 25
·期 10
·656-662
·
IF 1.894
Yangmin Ma,Hao Wu,Jin Zhang,Yanchao Li
A series of single isomers tetrahydro- β -carboline diketopiperazines were stereoselectively synthesized starting from l -tryptophan methyl ester hydrochloride and six aldehydes through a four-step reaction including Pictet-Spengler reaction, crystallization-induced asymmetric transformations (CIAT), Schotten-Baumann reaction, and intramolecular ester amidation. The chemical structures were characterized by nuclear magnetic resonance (NMR) and elemental analysis, among which two compounds were determined by x-ray single crystal diffraction. Moreover, antimicrobial activities of all the compounds were also tested. Chirality 25:656–662, 2013 . © 2013 Wiley Periodicals, Inc.
研究领域:
有机化学
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药物化学
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微生物学
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高影响因子
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2014
·
IF 2.129
Na Li,Jiang-Kun Dai,Hong-Tao Du,Mao-Sen Yuan,Ji-Wen Zhang,Jun-Ru Wang
A novel sensing system based on the β -carboline core has been designed and synthesized for Hg 2+ detection in water. We have demonstrated that a straight forward methodology can provide rapid, sensitive and selective recognition (cross-contamination experiments) for Hg 2+ over a wide pH range. The vivid fluorescence change from blue to colorless can be clearly discriminated by the naked eye. Furthermore, there is a good negative correlation between the fluorescent intensity and the concentration of Hg 2+ in the range 1.0 × 10 −6 M–7.0 × 10 −6 M. β -Carboline as a fluorophore synthesized via this route also provides a new strategy for the design of novel fluorescence probes and fluorochromes.
研究领域:
分析化学
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环境科学
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材料科学
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PubMed
高影响因子
Foods
·
2025
·Vol. 14
·期 2
·299
·
IF 5.1
Xiuxiu Liu,Wenyu Chen,Minghao Sun,Xufang Lv,Xing Shen,Zhongping Chai,Maomao Zeng
In this study, we aimed to investigate the inhibitory effects of cumin and cumin extracts from different origins (Hami, Turpan, and Hetian) on the formation ofβ-carboline heterocyclic amines (HCAs) in smoked meat and simulated systems, and to assess their potential as natural inhibitors in the food industry. The novelty of our research lies in the comprehensive comparative analysis of cumin extracts from different origins, which has not been fully explored in previous studies. We first conducted a quantitative analysis of the total phenol and flavonoid content in cumin extracts from the three origins and evaluated their antioxidant capacities. Subsequently, through simulation experiments, we assessed the inhibitory effects of these extracts on the formation ofβ-carboline heterocyclic amines and determined their free radical scavenging abilities. To further validate the practical application potential of these extracts, we prepared meat patty samples containing different concentrations of cumin powder, simulating actual processing conditions. The experimental results showed that while the total phenol content in cumin extracts from all origins was similar, averaging around 1.56 mg/g, there was a significant difference in the total flavonoid content, with the highest level observed in the Hetian cumin extract at 6.7 mg/g. Additionally, the Hetian cumin extract demonstrated superior antioxidant capacity, with an FRAP antioxidant activity reaching 21.04 μM TE/g dw, the highest among all samples. Our study also found that the inhibitory effect of cumin extracts on HCA formation was closely related to their free radical scavenging ability, with the Hetian cumin extract showing the strongest scavenging capacity. The addition of cumin powder to meat patties significantly reduced the content ofβ-carboline heterocyclic amines, particularly at lower cumin concentrations. In summary, our research results highlight the potential of cumin, especially from Hetian, as a natural inhibitor ofβ-carboline heterocyclic amine formation in processed meats. This study not only provides the food industry with a potential natural additive to improve food safety and quality, but also offers new directions for future research, namely by comparing natural plant extracts from different origins to explore their potential applications in food processing.
研究领域:
食品科学
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生物化学
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DOI
PubMed
高影响因子
MOLECULAR PHARMACEUTICS
·
2024
·
IF 4.5
Xudong Xie,Tiantian Sun,Heyu Pan,Dongliang Ji,Zhongyuan Xu,Ge Gao,Jiefei Miao,Lei Wang,Yanan Zhang,Ji Liu,Yong Ling,Xing Su
Chemo-photodynamic therapy is a treatment method that combines chemotherapy and photodynamic therapy and has demonstrated significant potential in cancer treatment. However, the development of chemo-photodynamic therapeutic agents with fewer side effects still poses a challenge. Herein, we designed and synthesized a novel series of β-carboline/furylmalononitrile hybrids 10a–i and evaluated their chemo-photodynamic therapeutic effects. Most of the compounds were photodynamically active and exhibited cytotoxic effects in four cancer cells. In particular, 10f possessed type-I/II photodynamic characteristics, and its 1O2 quantum yield increased by 3-fold from pH 7.4 to 4.5. Most interestingly, 10f exhibited robust antiproliferative effects by tumor-selective cytotoxicities and hypoxic-overcoming phototoxicities. In addition, 10f generated intracellular ROS and induced hepatocellular apoptosis, mitochondrial damage, and autophagy. Finally, 10f demonstrated extremely low acute toxicity (LD50 = 1415 mg/kg) and a high tumor-inhibitory rate of 80.5% through chemo-photodynamic dual therapy. Our findings may provide a promising framework for the design of new photosensitizers for chemo-photodynamic therapy.
研究领域:
药理学
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肿瘤学
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生物化学
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DOI
PubMed
高影响因子
BIOORGANIC CHEMISTRY
·
2025
·
IF 4.7
Yike Yang,Shanshan Su,Zhaoju Sun,Zhouqing Long,Xichun Fu,Jiao Meng,Xiang Zhou,Liwei Liu,Song Yang
The widespread prevalence of bacterial plant diseases imposes a severe constraint on global food production and crop security. To address the growing challenge of bacterial resistance, there is an urgent demand to develop novel agrochemicals that combine high efficacy with low toxicity. In this study, a natural product modification strategy was employed to design new bactericidal candidates with an innovative cation mechanism. Tryptamine was employed as a precursor to synthesize 1,2,3,4-tetrahydro-β-carboline (THC) intermediates via the Pictet-Spengler reaction. Subsequent acylation enabled the introduction of 3- N -substituted propionyl group as flexible bridge chain through an aza-Michael reaction. The resulting racemic THC derivatives were then evaluated for their antimicrobial activity. Notably, molecule B3 demonstrated exceptional inhibitory effects against Xanthomonas oryzae pv. oryzae ( Xoo , EC 50 = 1.32 μg/mL) and Xanthomonas axonopodis pv. citri ( Xac , EC 50 = 2.80 μg/mL), significantly outperforming commercial agents such as bismerthiazol (BT; EC 50 = 40.3 μg/mL for Xoo and 89.6 μg/mL for Xac ) and thiodiazole copper (TC; EC 50 = 58.2 μg/mL for Xoo and 37.3 μ g/mL for Xac ). Moreover, molecule B3 exhibited considerably higher activity than its parent molecule B (EC 50 = 7.27 μg/mL for Xoo and 4.89 μg/mL for Xac ). In vivo assays at 200 μg/mL, B3 provided protective effects of 53.87 % against Xoo and 91.2 % against Xac , exceeding those of TC. Mechanistic investigations revealed that molecule B3 disrupted the intracellular redox balance, and result in the accumulation of reactive oxygen species (ROS) and subsequent induction of apoptosis. These findings not only identify B3 as a promising ROS inducer for bactericide development but also offer novel insights into the role of ROS in combating bacterial diseases.
研究领域:
植物病理学
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药理学
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2022
·
IF 5.895
Shan-Shan Yang,Qing-Yun Lv,Juan Fu,Tian-Yi Zhang,Yi-Si Du,Xin-Juan Yang,Le Zhou
As our further research, a series of new 7-chloro-9-methyl-2-phenyl-3,4-dihydro-β-carbolin-2-iums were designed and synthesized. Twelve compounds were found with excellent inhibition activity in vitro on three to five out of six phytopathogenic fungi, superior to standard drugs thiabendazole and/or azoxystrobin. Especially, 18 displayed the highest activity against three out of the fungi and the highest comprehensive activity for all of the fungi. The test in vivo revealed that 18 at 50 μg/mL was able to completely control Physalospora piricola infections in apples over 8 days. Scanning/transmission electron microscopic observations found that 18 could damage the hyphal integrity and cell membrane structure of P. piricola. The safety evaluation showed that 18 had no effect on the germination rate of cowpea seed at ≤200 μg/mL. The SAR revealed that the combination of 7-Cl and 2′- or 4′-alkyl is conducive to improvement of the activity. Thus, 7-chloro-9-methyl-2-phenyl-3,4-dihydro-β-carbolin-2-ium is a promising antifungal lead scaffold.
研究领域:
植物病理学
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药物化学
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农学
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DOI
PubMed
高影响因子
BIOORGANIC CHEMISTRY
·
2024
·
IF 4.5
Li Guan,Aiyun Li,Pengfei Song,Wanzhen Su,Shengjie Zhang,Jiaxin Chen,Xiangying Jiao,Weize Li
Dual-specificity tyrosine phosphorylation-regulated kinase A (DYRK1A) is a potential drug target for diabetes. The DYRK1A inhibitor can promote β cells proliferation, increase insulin secretion and reduce blood sugar in diabetes. In this paper, a series β-carboline-cinnamic acid skeletal derivatives were designed, synthesized and evaluated to inhibit the activity of DYRK1A and promote pancreatic islet β cell proliferation. Pharmacological activity showed that all of the compounds could effectively promote pancreatic islet β cell proliferation at a concentration of 1 μM, and the cell viability of compound A1, A4 and B4 reached to 381.5 %, 380.2 % and 378.5 %, respectively. Compound A1, A4 and B4 could also inhibit the expression of DYRK1A better than positive drug harmine. Further mechanistic studies showed that compound A1, A4 and B4 could inhibit DYRK1A protein expression via promoting its degradation and thus enhancing the expression of proliferative proteins PCNA and Ki67. Molecular docking showed that β-carboline scaffold of these three compounds was fully inserted into the ATP binding site and formed hydrophobic interactions with the active pocket. Besides, these three compounds were predicted to possess better drug-likeness properties using SwissADME. In conclusion, compounds A1, A4 and B4 were potent pancreatic β cell proliferative agents as DYRK1A inhibitors and might serve as promising candidates for the treatment of diabetes.
研究领域:
药物化学
·
药理学
·
药物发现
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PubMed
高影响因子
FITOTERAPIA
·
2019
·
IF 2.431
Ning Wang,Jie Zhang,Qiao Li,Hui Xu,Geng Chen,Zhiyong Li,Difa Liu,Xin Yang
Indoleamine 2,3-dioxygenase (IDO) is one of the important targets for cancer immunotherapy through tryptophan pathway. Recently it has being paid great attention to search potent and safe IDO inhibitor from small-molecule compounds. Picrasma quassioides is a kind of medicinal plant abundant with tryptophan-derived indole alkaloids . By virtual screening and kinetic method for enzymatic analysis, lead compounds with potential IDO inhibitory activity were discovered for the first time from PQAs, the natural alkaloids in Picrasma quassioides . The results based on molecular docking analysis and structure-activity relationship (SAR) study demonstrated that coordinating with ferrous ion on the active site of IDO has a great impact on the inhibition potency, and β -carboline with carboxyl substituted on C-1 is the key pharmacophore for IDO inhibition of PQAs. Enzymatic assay provided further evidence for the effectiveness of β -carboline-1-carboxylic acid, which displayed as the most potent competitive inhibitor of IDO among these PQAs, and is even more potent than the recognized positive control 1-methyl tryptophan. This natural tryptophan-derived alkaloid thus deserved further deep research as a promising IDO modulator for cancer immunotherapy.
研究领域:
药理学
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肿瘤学
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植物化学
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PubMed
高影响因子
JOURNAL OF BIOTECHNOLOGY
·
2018
·
IF 2.533
Qi Chen,Shaofei Zhang,Yunchang Xie
The enzymatic Pictet-Spengler (PS) reaction, catalyzed by Pictet-Spenglerase (PSase), is the feature of β-carboline (βC) alkaloid biosynthesis. NscbB is a rare microbial PSase discovered from a cryptic β-carboline alkaloid biosynthetic gene cluster (BGC) in the Nocardiopsis synnemataformans DSM 44143 (kidney transplant patient derived) by homologous alignment with its well-characterized counterpart McbB. The biochemical analysis showed that NscbB could catalyze l -tryptophan ( K M = 89.64 ± 8.69 μM) and methylglyoxal ( K M = 147.70 ± 16.38 μM), without cofactors, to form the two βC skeletons 1-acetyl-3-carboxy-β-carboline and 1-acetyl-β-carboline in vitro . Additionally, the heterologous expression of nscbB in E. coli BL21 (DE3) revealed the efficient bioproductivity of NscbB to bioproduce two βC skeletons, 1-acetyl-3-carboxy-β-carboline (5.5 mg/L) and 1-acetyl-β-carboline (3.1 mg/L), within 16 h fermentation. These results demonstrate NscbB is a novel and practical microbial PSase, which is useful for future bioactive βC alkaloid exploitation and development.
研究领域:
生物化学
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微生物学
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生物技术
·
酶学
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DOI
PubMed
高影响因子
BIOMEDICINE & PHARMACOTHERAPY
·
2021
·
IF 6.53
Kaihui Zhang,Meiqi Wang,Yufeng Yao,Tao Huang,Fangle Liu,Chenchen Zhu,Chaozhan Lin
A rapid, sensitive, and reliable ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method has been developed to simultaneously determine the major bioactive components of Xiaoyan Lidan Formula (XYLDF) in rat plasma, using sulfamethoxazole as the internal standard (IS). The seven major bioactive components are andrographolide, dehydroandrographolide, enmein, 1-methoxicabony-β-carboline, 4,5-dimethoxy-canthin-6-one, 4-methoxy-5-hydroxy-canthin-6-one, and 1-hydroxymethyl-β-carboline. After pretreating by protein precipitation with methanol, separation was performed on a UPLC C18 column using gradient elution with a mobile phase consisting of acetonitrile and 0.1% formic acid at a flowing rate of 0.7 mL/min. Detection was performed on TSQ Quantum mass spectrometry set at the positive/negative ionization and multiple reaction monitoring (MRM) mode. The intra- and inter-day precision were less than 9.8%, whereas the intra- and inter-day accuracy were within ± 13.4%. The method was validated and applied to compare the pharmacokinetic profiles of the analytes in serum of Alpha-naphthylisothiocyanate (ANIT)-induced cholestasis and control rats after oral administration of XYLDF. The results showed remarkable differences in pharmacokinetic properties of the analytes between cholestatic (model) and control groups, thereby providing essential scientific information for better understanding of mechanism of XYLDF and a reference for its clinical applications.
研究领域:
药理学
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分析化学
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临床医学
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PubMed
高影响因子
RSC Advances
·
2025
·Vol. 15
·期 59
·51110-51119
·
IF 4.6
Puying Qi,Hongwu Liu,Yue Li,Daiyu Tang,Lei Shao,Junjie Wang,Qifei Zhu,Taibai Jiang,Lixia Li,Shilong Jiang,Fan Wu,Yanhong Guo,Yong Liu,Lihong Shi,Yin Wang,Jun Sun
Xanthomonas oryzae pv. Oryzae, result in rice bacterial blight, is the most severe bacterial disease affecting rice, and in certain regions, it is considered the most critical disease overall, with the potential to reduce yields by as much as 50%. It is difficult to control rice bacterial blight and lacking of pesticides. 1,2,3,4-Tetrahydro-β-carboline (THC) and their analogues show a diverse range of activities; however, research specifically focusing on THC remains limited, particularly concerning its antibacterial properties. Given its promising characteristics, THC holds potential for development as an environmentally friendly green pesticide. These outcomes reveal that THC signally inhibits both the cell growth and biofilm formation, thereby reducing its pathogenicity. Consequently, THC holds promise as a novel green pesticide aimed at targeting bacterial biofilms to effectively manage rice bacterial leaf blight.
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高影响因子
危险品化学品经营许可证（带存储）