Amino Derivatives Research Articles

Interaction of Some Amino-Nitrile Derivatives with Vascular Endothelial Growth Factor Receptor 1 (VEGFR1) Using a Theoretical Model.

Some studies indicate that the angiogenesis process is related to vascular endothelial growth factor, which can interact with endothelial cell surface receptors (VEGF-R1, VEGF-R2, and VEGF-R3); this biochemical process and other factors result in the promotion and growth of new blood vessels under normal conditions. However, some studies indicate that this phenomenon could also occur in cancer cells. It is important to mention that some amino derivatives have been prepared as VEGF-R1 inhibitors; however, their interaction with VEGF-R1 is not clear, perhaps due to different experimental approaches or differences in their chemical structure. The aim of this study was to evaluate the theoretical interaction of several amino-nitrile derivatives (Compounds 1 to 38) with VEGF-R1. The theoretical interaction of amino-nitrile derivatives with VEGF-R1 was carried out using the 3hng protein as the theoretical model. In addition, cabozantinib, pazopanib, regorafenib, and sorafenib were used as controls in the DockingServer program. The results showed different amino acid residues involved in the interaction of amino-nitrile derivatives with the 3hng protein surface compared with the controls. In addition, the inhibition constant (Ki) was lower for Compounds 10 and 34 than for cabozantinib. Other results show that Ki for Compounds 9, 10, 14, 27-29 and 34-36 was lower in comparison with pazopanib, regorafenib, and sorafenib. All theoretical data suggest that amino-nitrile derivatives could produce changes in the growth of some cancer cell lines through VEGFR-1 inhibition. Therefore, these amino-nitrile derivatives could be a therapeutic alternative to treat some types of cancer.

Liquid chromatography‐mass spectrometry‐based metabolomics reveals the comprehensive metabolites in Dioscorea opposita Thunb. peel

AbstractDioscorea opposita Thunb., a traditional medicinal and food homologous plant, has been used for thousands of years in folk medicine and nutritious food, partially due to the metabolites. However, detailed information on the metabolites in Dioscorea opposita Thunb. peel is still scarce. Herein, an ultra‐high‐performance liquid chromatography‐quadrupole/orbitrap high‐resolution mass spectrometry‐based metabolomics approach was used to reveal the comprehensive metabolites in Dioscorea opposita Thunb. peel. The proposed method provided tentative identification of 307 metabolites. Among them, 286 metabolites are reported herein in Dioscorea opposita Thunb. peel for the first time, namely: 87 lipids, 49 phenolic acids, 34 flavonoids, 29 amino acids and derivatives, 28 organic acids, 14 alkaloids, 10 lignans, and coumarins, eight saccharides and vitamins, six nucleotides and derivatives, two quinones, and 19 others. The obtained results highlight the importance of Dioscorea opposita Thunb. peel as a promising source of bioactive ingredients, and form a basis for future quantitative and bioavailability studies.

Network pharmacology and molecular docking combined with widely targeted metabolomics to elucidate the potential compounds and targets of Euphorbia helioscopia seeds for the treatment of pulmonary fibrosis

BackgroundThe whole herb of Euphorbia helioscopia has been traditionally used for treating pulmonary tuberculosis, malaria, warts, lung cancer and bacillary dysentery for a long time in China. However, E. helioscopia seeds are often discarded and its medicinal value is often ignored, resulting in a waste of resources. MethodIn this work, widely targeted metabolomics based on UPLC-ESI-QTRAP-MS/MS methods and metware database (MWDB) were firstly used to identify the chemical compositions of EHS. Besides, network pharmacology, molecular docking and molecular dynamics simulation were performed for elucidating the potential compounds and targets of E. helioscopia seeds for the treatment of pulmonary fibrosis via common database (like TCMSP, Genecards, DAVID, STRING) and common software (like Sybyl, Cytoscape, Pymol and Schrödinger). ResultThe results of widely targeted metabolomics showed 231 compounds including 12 categories were identified. The highest content compositions are lipids (33.89%) followed by amino acids and derivatives (21.78%), nucleotides and derivatives (15.73%), as well as the content of functional ingredients like phenolic acids (7.33%), alkaloids (7.03%) and flavonoids (4.51%) are relatively high. Besides, the results of network pharmacology and molecular docking showed that EHS presented anti-pulmonary fibrosis medicinal value through multi-ingredients, multi-targets and multi-pathways approach. Key ingredients including 9-Hydroxy-12-oxo-15(Z)-octadecenoic acid, Nordihydrocapsiate, 1-O-Salicyl-d-glucose, 9-(Arabinosyl)hypoxanthine, Xanthosine and Galangin-7-O-glucoside. Key targets including SRC, HSP90AA1, AKT1, EGFR, JUN, EP300 and VEGFA, and key signaling pathways mainly related to AGE-RAGE, EGFR tyrosine kinase inhibitor resistance, VEGF and HIF-1 signaling pathway. Molecular dynamics simulation showed that HSP90AA1 and 9-Hydroxy-12-oxo-15(Z)-octadecenoic complex (with the highest docking score) have a stable combination effect. ConclusionIn conclusion, this study revealed the chemical compositions of EHS and its anti-pulmonary fibrosis medicinal effect for the first time, it will provide scientific insight for the development of EHS as medicinal resource.

SLC36 family of proton-coupled amino acid transporters in GtoPdb v.2023.1

Members of the SLC36 family of proton-coupled amino acid transporters are involved in membrane transport of amino acids and derivatives [29, 30]. The four transporters show variable tissue expression patterns and are expressed in various cell types at the plasma-membrane and in intracellular organelles. PAT1 is expressed at the luminal surface of the small intestine and absorbs amino acids and derivatives [4]. In lysosomes, PAT1 functions as an efflux mechanism for amino acids produced during intralysosomal proteolysis [2, 26]. PAT2 is expressed at the apical membrane of the renal proximal tubule [7] and at the plasma-membrane in brown/beige adipocytes [31]. PAT1 and PAT4 are involved in regulation of the mTORC1 pathway [12, 28]. More comprehensive lists of substrates can be found within the reviews under Further Reading and in the references [3].

Unprecedented facile approach of multiple amino-substituted triphenylamine derivatives for electrochromic devices with extremely high coloration efficiency and unexpected redox stability

Generally, the amino group is considered highly reactive and unstable. Thus, the amino derivatives would be entirely consumed by polymerization or end-capping to preserve the material stability in most research or application fields. Herein, we demonstrated that triphenylamine (TPA) with multiple para-amino substituents could reduce oxidation potential and provide extra oxidation sites while retaining their reversibility. Four para-amino-substituted TPA derivatives (TPA-1N, TPA-2N, TPA-3N, and TPA-ADM) designed and prepared in this study exhibited excellent stability under the electrochemical redox procedure, revealing more than 88% reversibility in the continuous cyclic voltammetry process up to 10,000 cycles. Among all the electrochromic devices, TPA-3N/HV performs the highest coloration efficiency (631 cm2/C), coloration speed (46.4 % s−1), and superior stability, manifesting a reversibility of 99% or 98% after 1000 cycles (switching) or 10 h (maintaining at coloring state), respectively.

Genomic analysis of Paenibacillus macerans strain I6, which can effectively saccharify oil palm empty fruit bunches under nutrient-free conditions

The improper disposal of palm oil industrial waste has led to serious environmental pollution. In this study, we isolated Paenibacillus macerans strain I6, which can degrade oil palm empty fruit bunches generated by the palm oil industry in nutrient-free water, from bovine manure biocompost and sequenced its genome on PacBio RSII and Illumina NovaSeq 6000 platforms. We obtained 7.11 Mbp of genomic sequences with 52.9% GC content from strain I6. Strain I6 was phylogenetically closely related to P.macerans strains DSM24746 and DSM24 and was positioned close to the head of the branch containing strains I6, DSM24746, and DSM24 in the phylogenetic tree. We used the RAST (rapid annotation using subsystem technology) server to annotate the strain I6 genome and discovered genes related to biological saccharification; 496 genes were related to carbohydrate metabolism and 306 genes were related to amino acids and derivatives. Among them were carbohydrate-active enzymes (CAZymes), including 212 glycoside hydrolases. Up to 23.6% of the oil palm empty fruit bunches was degraded by strain I6 under anaerobic and nutrient-free conditions. Evaluation of the enzymatic activity of extracellular fractions of strain I6 showed that amylase and xylanase activity was highest when xylan was the carbon source. The high enzyme activity and the diversity in the associated genes may contribute to the efficient degradation of oil palm empty fruit bunches by strain I6. Our results indicate the potential utility of P.macerans strain I6 for lignocellulosic biomass degradation.

Metabolomic and transcriptomic responses of Adiantum (Adiantum nelumboides) leaves under drought, half-waterlogging, and rewater conditions.

Introduction: Adiantum nelumboides (Adiantum) is an endangered fern with a narrow distribution along the Yangtze River in China. Due to its cliff-dwelling habit, it experiences water stress conditions, which further endangers its survival. However, no information is available about its molecular responses to drought and half-waterlogging conditions. Methods: Here, we applied five and ten days of half-waterlogging stress, five days of drought stress, and rewatering after five days of drought stress, and studied the resulting metabolome profiles and transcriptome signatures of Adiantum leaves. Results and Discussion: The metabolome profiling detected 864 metabolites. The drought and half-waterlogging stress induced up-accumulation of primary and secondary metabolites including amino acids and derivatives, nucleotides and derivatives, flavonoids, alkaloids, and phenolic acid accumulation in Adiantum leaves. Whereas, rewatering the drought-stressed seedlings reversed most of these metabolic changes. Transcriptome sequencing confirmed the differential metabolite profiles, where the genes enriched in pathways associated with these metabolites showed similar expression patterns. Overall, the half-waterlogging stress for 10 days induced large-scale metabolic and transcriptomic changes compared to half-waterlogging stress for 05 days, drought stress for 05 days or rewatering for 05 days. Conclusion: This pioneering attempt provides a detailed understanding of molecular responses of Adiantum leaves to drought and half-waterlogging stresses and rewater conditions. This study also provides useful clues for the genetic improvement of Adiantum for drought/half-waterlogging stress tolerance.

SERS study of cyanine dyes: Optimization of metal core and molecular label choice for plasmonic nanotags

The combined use of dyes and plasmonic nanoparticles provides new opportunities for the development of surface-enhanced Raman scattering (SERS) tags for imaging and sensing applications. Here, we report for the first time the detailed SERS study of cyanine5.5 and cyanine7.5 derivatives interaction with gold nanoparticles. SERS spectra were recorded for the solutions of nanoparticles of six different morphologies to reveal the combination of dye and plasmonic core with the highest optical response. Three compounds were tested to select the most appropriate functional derivative: cyanine5.5 amine, sulfo-cyanine5.5 amine and sulfo-cyanine5.5 NHS ester. Bare CTAB-stabilized gold nanoparticles and gold nanoparticles covered by oppositely charged polymers were used in the SERS study. The effect of chloride anions was tested for dyes adsorbed on both uncoated and coated nanoparticles. Amino derivative of non-sulfonated cyanine5.5 demonstrated the most intensive and stable SERS response which increases with the addition of chloride even when dye molecules are adsorbed on polystyrene sulfonate polymer layer. The study allows one to get acquainted with many findings that are useful for obtaining SERS and bimodal Raman-fluorescence nanotags containing dyes.

Recent advances in the chemistry of two-carbon nitro-containing synthetic equivalents

To date, nitro-containing compounds form one of the most important classes of organic compounds. The chemistry of these molecules attracts attention primarily due to their use as high-energy reagents and drugs. Also, the introduction of a nitro group is a popular synthetic strategy for constructing new organic molecules. The present review summarizes the latest research findings of compounds bearing a nitro group on a two-carbon moiety such as aminonitroethylenes, α,α-bis(alkylsulfanyl)nitroalkenes and their amino derivatives, α-nitroketones, alkyl nitroacetates and nitroacetonitrile. The literature data are systematized according to the type of chemical reactions such as reactions between nucleophiles and electrophiles, various cyclization reactions, reactions at the C–H bond, <i>etc</i>. The reactivities of the said nitro compounds and the conditions of chemical transformations are compared to assess the prospects of their application.<br> The bibliography includes 314 references.

Amino Derivatives of Acridine: Synthesis and Study of Anticholinesterase and Antioxidant Activity

Amino Derivatives of Acridine: Synthesis and Study of Anticholinesterase and Antioxidant Activity

Efficient and Reversible Capture of CO2 in CO2-Binding Organic Liquids Formed by 1,1,3,3-Tetramethylguanidine and Glycerol Derivatives

A class of CO2-binding organic liquids (CO2-BOLs) composed of 1,1,3,3-Tetramethylguanidine (TMG) and Glycerol (Gly) and Gly’s amino derivatives were developed for highly efficient and reversible CO2 capture. These CO2-BOLs exhibited high gravimetric CO2 solubility up to 0.196 g CO2·g–1 at 313.2 K and 1.0 atm, superior to most functionalized ILs and other absorbents. The influential factors of CO2 absorption, such as components of CO2-BOLs, absorption temperature, and CO2 partial pressure together with water contents were investigated, and the recyclability of CO2-BOLs was verified to be excellent. The absorption mechanism of CO2-BOLs was explored with the help of spectral analysis, quantum chemical calculation, and thermodynamic analysis. All the results revealed that chemisorption took place once these CO2-BOLs were exposed to CO2, and alkyl guanidine carbonates were produced. Besides, it is illustrated that introducing the amino group to Gly could reduce the nucleophilic reactivity of CO2-BOLs, along with the absorption enthalpy simultaneously.

INVESTIGATION OF THE WETTING EFFECT OF SURFACTANTS OF VARIOUS NATURE IN THE BITUMEN COMPOSITION

Asphalt concrete coverings are short-lived and are destroyed under the influence of external factors. The insufficient degree of adhesion at the interface between the bituminous binder and the hard surface of the mineral material causes a low hydrophobicity of asphalt concrete coatings, which is the main cause of damage and premature wear of the roadway. Optimization of the bitumen composition by introducing a variety of modifying agents can intensify the processes of wetting the hard surface with bitumen and increase the hydrophobicity of the surface films formed by it. The purpose is to establish the influence of various modifiers on the processes of wetting the surface of crushed stone with a bituminous composition, as well as to study the regularities of the influence of modifiers on the hydrophobicity of bituminous films. The methodology of this work included experimental determination of the wetting contact angle θ of a solid surface by the lying drop method at T=298 K. Results. Increasing the AC-2K content in bitumen from 0 to 1% reduced the contact wetting angle by 11.31° (relative to the base version without the modifier) to 114.35°. The AC-2 modifier contributes less to improving the wettability of the surface of the basic crushed stone with bitumen; with Cm=1%, the contact wetting angle is reduced to 118.68°. When modifying bitumen, PPS recorded a significantly smaller decrease in wetting contact angle at a higher concentration (Cm=2%) – by 2.4° (from 125.66° to 123.26°). The amino derivative AC-2K (Cm=1%) has the greatest water-repellent effect among the studied modifiers, increasing the wetting edge angle to 99.07°. Conclusion. The water-repellent properties of bituminous compositions are enhanced (Δθ=4.02°) at a narrow range of concentrations of the modifier AC-2K (with Сm=1%). The ultrasonic cavitation-derived AC-2K can be recommended for use in asphalt concrete coatings as an adhesive additive that provides a good wetting effect of bitumen in relation to the surface of the mineral filler while also increasing the hydrophobicity of bitumen films.

Influence of the Solvent on the Stability of Aminopurine Tautomers and Properties of the Amino Group

Amino derivatives of purine (2-, 6-, 8-, and N-NH2) have found many applications in biochemistry. This paper presents the results of a systematic computational study of the substituent and solvent effects in these systems. The issues considered are the electron-donating properties of NH2, its geometry, π-electron delocalization in purine rings and tautomeric stability. Calculations were performed in ten environments, with 1 < ε < 109, using the polarizable continuum model of solvation. Electron-donating properties were quantitatively described by cSAR (charge of the substituent active region) parameter and π-electron delocalization by using the HOMA (harmonic oscillator model of aromaticity) index. In aminopurines, NH2 proximity interactions depend on its position and the tautomer. The results show that they are the main factor determining how solvation affects the electron-donating strength and geometry of NH2. Proximity with the NH∙∙∙HN repulsive interaction between the NH2 and endocyclic NH group results in stronger solvent effects than the proximity with two attractive NH∙∙∙N interactions. The effect of amino and nitro (previously studied) substitution on aromaticity was compared; these two groups have, in most cases, the opposite effect, with the largest being in N1H and N3H purine tautomers. The amino group has a smaller effect on the tautomeric preferences of purine than the nitro group. Only in 8-aminopurine do tautomeric preferences change: N7H is more stable than N9H in H2O.

Ultra-performance liquid chromatography-tandem mass spectrometry revealed the significantly different metabolic profiles of Auricularia cornea growing on weakly acidic and weakly alkaline substrates.

Auricularia cornea is a widely prized basidiomycetous mushroom with culinary and medicine value, which is cultivated artificially on a large scale in China. However, little attention has been paid to the differences in metabolic profiles under different pH growth conditions. In the present study, weakly acidic and weakly alkaline artificial substrates were developed and used for the cultivation of A. cornea, and the metabolic profiles of its fruiting bodies were determined using ultra performance liquid chromatography-tandem mass spectrometry. The results show that the weakly alkaline substrate environment promoted mycelial growth, increased body surface area, and improved yield and transformation efficiency, but attenuated metabolite accumulation by A. cornea. A total of 412 different metabolites were identified in negative and positive ion mode, of which 99 had significantly different amounts and covered 51 metabolic pathways. Principal component analysis and orthogonal patrial least squares discriminant analysis showed clear separation between two treatments, indicating different metabolic profiles. The different metabolites mainly included seven chemical categories, including amino acids and derivatives, nucleotides and derivatives, phenolic acids, organic acids, lipids, flavonoids and alkaloids. This study revealed the biological significance of these metabolites, which could be useful for further unexplored compounds and possible biological functions of A. cornea.

A novel visualization method for the composition analysis of processed garlic by MALDI-TOF imaging mass spectrometry (MSI) and Q-TOF LC-MS/MS

Laba garlic is a kind of vinegar processed garlic (Allium sativum L.) product with multiple health effects. This study applied matrix-assisted laser desorption/ionization imaging mass spectrometry (MALDI-TOF MSI) and Q-TOF LC-MS/MS for the first time to investigate the garlic tissue spatial distribution changes of low molecular weight compounds during the Laba garlic processing. The distribution characteristics of the compounds were observed in processed and unprocessed garlic including amino acids and derivatives, organosulfur compounds, pigment precursors, polysaccharides and saponins. During Laba garlic processing, some bioactive compounds such as alliin and saponins were lost because they were transformed into other compounds or leached into the acetic acid solution, and some new compounds including pigments-related compounds occurred. This study provided a basis for the spatial distributions and changes of compounds in garlic tissue during Laba garlic processing, which suggested that the bioactivities of garlic might be changed after processing owing to the transformation and change of the constituents.

Integrated Transcriptomic and Metabolomic Analyses Reveal the Molecular and Metabolic Basis of Flavonoids in Areca catechu L.

Areca catechu L., of the Arecaceae family, is widely distributed in tropical Asia. In A. catechu, the extracts and compounds, including flavonoids, have various pharmacological activities. Although there are many studies of flavonoids, the molecular mechanism of their biosynthesis and regulation remains unclear in A. catechu. In this study, 331 metabolites were identified from the root, stem, and leaf of A. catechu using untargeted metabolomics, including 107 flavonoids, 71 lipids, 44 amino acids and derivatives, and 33 alkaloids. The transcriptome analysis identified 6119 differentially expressed genes, and some were enriched in the flavonoid pathway. To analyze the biosynthetic mechanism of the metabolic differences in A. catechu tissues, 36 genes were identified through combined transcriptomic and metabolomic analysis, in which glycosyltransferase genes Acat_15g017010 and Acat_16g013670 were annotated as being involved in the glycosylation of kaempferol and chrysin by their expression and in vitro activities. Flavonoid biosynthesis could be regulated by the transcription factors, AcMYB5 and AcMYB194. This study laid a foundation for further research on the flavonoid biosynthetic pathway of A. catechu.

Cyan Fluorescent Carbon Quantum Dots with Amino Derivatives for the Visual Detection of Copper (II) Cations in Sea Water

Amino- and carboxyl-functionalized carbon quantum dots (Amino-CQDs) were synthesized through fast and simple microwave treatment of a citric acid, ethylenediamine and ethylenediaminetetraacetic acid (EDTA) mix. The reproducible and stable optical properties from newly synthesized CQD dispersion with a maximum absorbance spectra at 330 nm and the symmetric emission maximum at 470 nm made the Amino-CQDs a promising fluorescence material for analytical applications. The highly aminated and chelate moieties on the CQDs was appropriate for a copper (Cu2+) cation sensor in the linear range from 1 × 10-4 mg/mL to 10 mg/mL with a limit of detection at 0.00036 mg/mL by static fluorescence quenching effects. Furthermore, Amino-CQDs demonstrated stable fluorescence parameters for assays in diluted alkali metal solution (Na+ and K+) and sea water. Finally, a visual sensor, based on Amino-CQDs, was successfully created for the 0.01-100 mg/mL range to produce a colorimetric effect that can be registered by computer vision software (Open CV Python).

Characterization of substrates and inhibitors of the human heterodimeric transporter 4F2hc-LAT1 using purified protein and the scintillation proximity radioligand binding assay.

Amino acids have diverse and essential roles in many cellular functions such as in protein synthesis, metabolism and as precursors of different hormones. Translocation of amino acids and derivatives thereof across biological membranes is mediated by amino acid transporters. 4F2hc-LAT1 is a heterodimeric amino acid transporter that is composed of two subunits belonging to the SLC3 (4F2hc) and SLC7 (LAT1) solute carrier families. The ancillary protein 4F2hc is responsible for the correct trafficking and regulation of the transporter LAT1. Preclinical studies have identified 4F2hc-LAT1 as a valid anticancer target due to its importance in tumor progression. The scintillation proximity assay (SPA) is a valuable radioligand binding assay that allows the identification and characterization of ligands of membrane proteins. Here, we present a SPA ligand binding study using purified recombinant human 4F2hc-LAT1 protein and the radioligand [3H]L-leucine as tracer. Binding affinities of different 4F2hc-LAT1 substrates and inhibitors determined by SPA are comparable with previously reported K m and IC 50 values from 4F2hc-LAT1 cell-based uptake assays. In summary, the SPA is a valuable method for the identification and characterization of ligands of membrane transporters including inhibitors. In contrast to cell-based assays, where the potential interference with other proteins such as endogenous transporters persists, the SPA uses purified protein making target engagement and characterization of ligands highly reliable.

Synthesis, DFT investigations, antioxidant, antibacterial activity and SAR-study of novel thiophene-2-carboxamide derivatives

Synthetic strategy for the synthesis of thiophene 2-carboxamide derivatives substituted with hydroxyl, methyl and amino groups at position-3 was proposed. The strategy includes the cyclization of the precursor ethyl 2-arylazo-3-mercapto-3-(phenylamino)acrylate derivatives, 2-acetyl-2-arylazo-thioacetanilide derivatives and N-aryl-2-cyano-3-mercapto-3-(phenylamino)acrylamide derivatives with N-(4-acetylphenyl)-2-chloroacetamide in alcoholic sodium ethoxide. IR, 1H NMR, and mass spectroscopic analyses were used to characterize the synthesized derivatives. In addition, molecular, electronic properties of the synthesized products were studied by the density functional theory (DFT) where they exhibited close HOMO–LUMO energy gap (ΔEH-L) in which the amino derivatives 7a-c have the highest while the methyl derivatives 5a-c were the lowest. Using the ABTS method, the antioxidant properties of the produced compounds were evaluated, where amino thiophene-2-carboxamide 7a exhibit significant inhibition activity 62.0% compared to ascorbic acid The antibacterial activity against two pathogenic Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two of pathogenic Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) revealed that 7b records the highest activity index compared to ampicillin 83.3, 82.6, 64.0, 86.9%, respectively. Furthermore, the thiophene-2-carboxamide derivatives were docked with five different proteins with the use molecular docking tools and the results explained interactions between amino acid residue of enzyme and compounds. Compounds 3b and 3c showed the highest binding score with 2AS1 protein. Graphical

Cytogenetic Characterization and Metabolomic Differences of Full-Sib Progenies of Saccharum spp.

Sugarcane smut is a worldwide fungal disease. Disease resistance breeding is the most economical and effective measure to prevent and control sugarcane smut. The cytogenetic characteristics and metabolomic differences of sugarcane F1s are closely related to disease resistance. Zhongzhe 1 and G160 sugarcane from the same parents (ROC25 and Yunzhe89-7) were used; the plants were grown in accordance with the barrel method. When the seedlings had 4-5 leaves, genomic in situ hybridization (GISH) was performed; digoxigenin (DIG)-labeled female parental (ROC25)DNA and biotin-labeled male parental (Yunzhe89-7) DNA were used as probes, and the karyotypes of two hybrids were analyzed. The new sugarcane smut-resistant variety (Zhongzhe 1) and the susceptible variety (G160) derived from the same parent were analyzed via gas chromatography-mass spectrometry technology (GC-MS) to compare the metabolomic differences between them. GISH analysis revealed that the chromosome ploidy number of Zhongzhe 1 sugarcane and G160 sugarcane were 114 and 110, respectively. However, the two contain different numbers of chromosomes from the female (ROC25) and male (Yunzhe89-7) parents. Moreover, 258 significantly changed metabolites were identified in smut-resistant Zhongzhe 1, as compared with the smut-susceptible G160 sugarcane: 56 flavonoids, 52 phenolic acids, 30 lipids, 26 organic acids, 26 amino acids and derivatives, 19 nucleotides and derivatives, 5 alkaloids, 9 terpenoids, and 35 others. Multivariate statistical analysis revealed a distinct difference in metabolic pathways between Zhongzhe 1 sugarcane and G160, and both of these varieties had unique functional metabolites. Differences in chromosome composition may constitute the genetic basis for the difference in resistance to smut disease between Zhongzhe 1 sugarcane and G160 sugarcane, and a high accumulation of flavonoids, lipids, terpenoids and tannins may constitute the basis of resistance to smut disease for the Zhongzhe 1 variety.