Single-crystal Analysis Research Articles

Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry

The preparation, functionalization, and investigations in host-guest properties of high-level pillararene macrocycles have long been a big challenge because of the lack of efficient synthetic methods. Herein, a novel type of pillararene derivative, namely desymmetrized pillar[8]arene (DP[8]A), has been successfully synthesized via a facile two-step strategy with high yield. Compared with its pillar[8]arene counterpart, DP[8]A is composed of four alkoxy-substituted benzene units and four bare benzene rings. Single crystal analysis has been performed in order to unveil the molecular conformation and packing mode of DP[8]A, which indicated that DP[8]A possesses a unique chair-like structure and much smaller steric hindrance. Density functional theory (DFT) calculations and electrostatic potential map suggested the inhomogeneous electronic distribution in the DP[8]A cavity. Water-soluble carboxylate-modified DP[8]A, that is, CDP[8]A, was also prepared to investigate the host-guest properties in aqueous solution with methyl viologen (MV), where the binding constant and morphologies of the formed host-guest complexes have been studied. In all, this new version of eight-membered pillararene derivative might potentially serve as a powerful macrocycle candidate for further applications in supramolecular chemistry.

A comparative study of second order Non-linear optical crystals derived from chloro- and dichloro- aniline

Followed by one-pot mechanism Schiff base products derived from the substituted anilines are crystallized by the slow-evaporation technique. Both crystals are characterized by FT-IR, 1H NMR and 13C NMR spectral studies. Single crystal XRD analysis provides data of both crystals and it is well fitted with NMR and IR spectral results. The obtained results of IR frequencies and NMR chemical shifts are compared with theoretical predicted results obtained from DFT method. The energy gap Eg was calculated by HOMO and LUMO and other theoretical parameters are determined by using DFT method with B3LYP/6–311++ G (d,p) basis set and the energy gap is very small 3.59, 3.52 eV for PCA and DCA crystals. The supramolecular investigation of crystal structure explained by Hirshfeld analysis. Using quantum computations techniques, the topological parameters LOL and ELF, scatter graph and diagram of the crystals was the further characterization. The first order hyperpolarizability (β0) was calculated by B3LYP/6–311++ G (d,p) basis set. Using the Kurtz-Powder technique, the second order Non-linear optical activity of the crystal was obtained. Based upon these crystals, which are outstanding Nonlinear optical activity material and best for the laser safety devices.

Study on magnetic properties of two dysprosium(III)-substituted antimonotungstates with different substitution modes

Two Polyoxometalates have been constructed by simple hydrothermal synthesis using rare-earth (RE) and antimonotungstates (ATs) {B-α-SbW9O33} as raw materials with the molecular formulas of H4.5Na1.5(H2O)6(C3H5N2)3{Na(Sb3O)2[B-β-SbW8O31Dy(H2O)2]3}·12H2O (1) and H9(C3H5N2)5{[Sb6IIISbVDy2WO10(H2O)5][(B-β-SbW9O33)2(B-α-SbW9O33)]}·16H2O (2). X-ray Single crystal diffractometer analysis shows that both 1 and 2 possess trimer configurations. Polyoxoanion 1 is assembled from three trilacunary {B-β-SbW8O31Dy(H2O)2}p units linked via {Na(Sb3O)2} cluster, where the trilacunary {B-β-SbW8O31Dy(H2O)2} unit is formed by the tetralacunary {B-β-SbW8O31} unit captures one Dy(H2O)23+ cation. Polyoxoanion 2 is composed of a novel 5p−4f heterometallic cluster {Sb6IIISbVDy2WO12(H2O)5} simultaneously stabilized by two {B-β-SbW9O33} units and one {B-α-SbW9O33} unit. In addition, two-dimensional correlation infrared spectroscopy (2D COS-IR) under magnetic disturbance was measured to investigate the difference of the variable temperature magnetic susceptibility between two compounds to explore the source of magnetic properties, and further magnetic property tests indicate that 1 and 2 may exhibit single-molecule-magnet behavior with distinct frequency dependence. This work deepens the theory of 2D COS-IR and also enriches the theoretical and experimental data of magnetism.

Asymmetric synthesis of enantiopure tetracyclic dispirooxindolopyrrolidine-piperidones via microwave-assisted multicomponent reaction: Crystallographic analysis, antimicrobial activity and in silico studies

In an attempt towards the development of new antimicrobials, we synthesized by microwave-assisted multicomponent reaction (MCR) of enantiopure (E,E)-3,5-bisarylidene-N-[(S)-(-)-methylbenzyl]-4-piperidones, isatin and α-amino esters a series of optically active tetracyclic dispirooxindolopyrrolidine-piperidones. The beneficial and promising features of this protocol such as simple operational procedure, short reaction time (10 min), and high product yields (up to 97 %) make it an efficient eco-friendly approach offering a powerful mean to expand the structural diversity of spirooxindoles. This approach appears hugely advantageous for high-throughput screening processes in drug discovery research. In addition, crystallographic parameters and inter- and intramolecular interactions occurring in spiropyrrolidine-fused piperidone derivative 4g were examined through single-crystal XRD analysis allowing to determine the absolute configuration of the enantiopure compound. The preliminary biological assessment of their antimicrobial activity indicates that most of the screened products display higher activity than the standard reference drugs Ampicillin and Griseofulvin. Some of them exhibited good to moderate activity against both bacteria and fungi. In addition, in silico molecular docking and predictive ADMET studies for the most active spirocompounds were carried out. Molecular docking confirmed the binding efficacy of candidates 4c and 4l through low score energy values and the establishment of diverse bonding interactions with the active site residues. Finally, the ADMET profiling of the most active spiroheterocycles proved their remarkable drug-like and pharmacokinetic properties.

TPE[2]arenes: Luminescent macrocyclic arenes with aggregation-induced emission and Al3+ detection

Luminescent macrocyclic arenes have attracted interest owing to their unique cyclic geometry and adaptive emission. Herein, a series of fluorescent macrocyclic arenes, denoted as TPE [2]arenes, were easily synthesized by the one-pot condensation of tetraphenylethene (TPE) moiety and paraformaldehyde in the presence of BF3·OEt2 and readily derivatized to yield cyclic arenes with diverse substitution patterns. The macrocyclic arenes shared similar cyclic skeleton with resorcin [4]arene, and existed as two enantiomers with boat conformation confirmed via single crystal analysis. Furthermore, TPE [2]arenes all retained the aggregation-induced emission properties owing to the incorporation of TPE moiety and obvious mechanochromic luminescence behavior due to the relative flexible skeleton. The carboxylic acid substituted analogues, namely TPE [2]arene-COOH, exhibited specific “turn-on” detection of Al3+ ion in aqueous media.

Wall-trapped acetylene tetramer in a metal-organic framework enables kinetic separation of C2H2/C2H4

Effective separation of acetylene/ethylene (C2H2/C2H4) mixtures by adsorption is a challenging but green method given their similar molecular characters. An increasing number of metal-organic frameworks (MOFs) have addressed the diffusion-related challenges to achieve the separation, yet almost all of them just focus on diffusion rates and disregard the geometrical arrangement of adsorbed molecules which exerts important effects in boosting the diffusion behaviors. Herein, we now present a paradigm using an ultramicroporous zinc-MOF (Zn-MOF, referred to as 1) with assessable size of 3.4 × 3.3 Å2, as demonstrated by single-crystal and theoretical analysis, which realizes the effective separation of C2H2 from its competitors. Static adsorption isotherms indicate that 1 possesses higher C2H2 uptake of 28.4 cm3 g−1 at 298 K and 0.1 bar, achieving a high IAST selectivity of 265 among the benchmark MOFs. Theoretical calculations reveal that C2H2 molecules are grasped through multiple binding interactions and adsorbed in the pore surface rather than the center of the pore, thus forming C2H2 tetramer through connecting four C2H2 motifs. Further, time-dependent kinetic tests coupled with molecular dynamics confirm the faster diffusion behavior for C2H2, mainly attributing to unimpeded diffusion channel. Column breakthrough tests demonstrate that 1 can easily accomplish exclusive separation of C2H2 from various binary ethane dehydrogenation (EDH) and senary non-oxidative coupling of methane (non-OCM) byproducts. Specially, structurally stable 1 can be readily synthesized utilizing inexpensive raw materials, yielding the cost of only $614 per kilogram. Accordingly, this work proposes a novel strategy of wall-trapped C2H2 tetramer in MOF that can effectively promote the kinetic behavior through available diffusion channel, expecting to offer a new perspective and provide guidance for future research.

Comparing Microcrystal Electron Diffraction (MicroED) and X-ray crystallography as methods for structure determination of Oseltamivir phosphate

Oseltamivir phosphate is a pharmaceutical used in the treatment of influenza viruses. Panče Naumov et al. took two years of dedicated single crystal cultivation and successfully obtained low-quality single crystals through a diffusion method. Cultivation of Oseltamivir phosphate single crystals was proved to be difficult and can extend over several months or more. We employed microcrystalline electron diffraction (MicroED) for direct powder measurements, eliminating the need for lengthy single-crystal cultivation, and the time to obtain the molecular structure of Oseltamivir phosphate was shortened from several months to five hours. Comparative analyses of single crystal (Crystal 1) and MicroED (Crystal 2) results revealed equivalent crystal structures, with minimal differences in hydrogen bond distances, identical powder X-ray diffraction patterns, and negligible variations in Hirshfeld surface analysis. The differential scanning calorimetry (DSC) analysis showcased a higher melting point of Oseltamivir phosphate (206.0 °C) than Oseltamivir (110.7 °C), indicating that Oseltamivir phosphate had high temperature stability, and may result in the selection of Oseltamivir phosphate as a formulation form. The study establishes and verifies a congruence between MicroED detection and traditional single-crystal detection methods and may be applied in the elucidation of compound structures and the surveillance of drug polymorphism.

Ion pair induced supramolecular assembly for development of novel pyridine 2, 6 diamide spacer acyl hydrazone-based derivatives for selective sensing of ZnCl2 and AlCl3

The work reports the development of a novel pyridine 2, 6 diamide spacer acyl hydrazone-based dual sensor H2L via two intermediates 1 and 2. The sensor as well as intermediates have been spectroscopically characterized. The structure of intermediate 1 is validated by its single crystal data analysis. As H2L bears both amide and acyl hydrazone moiety which have selective detection ability of anion and cation respectively, after rigorous characterization, the sensors are exposed to check their dual binding behavior. The results of several spectroscopic studies disclose the fact that H2L can optically and fluorometrically detect Al (III) and Zn (II) among several competitive cations and Cl− among competitive anions in semi-aqueous and aqueous medium respectively. Interestingly in a 9:1 DMSO-water medium, the probe can act as an ion pair sensor and in this medium, the probe can simultaneously detect Zn (II)/Cl- and Al (III)/Cl- forming H2L-ZnCl2, H2L-AlCl3 adduct. The 1:1 probe-analyte ion-pair binding is confirmed by NMR and mass spectral study. The Density Functional Theory (DFT) study optimizes the structures of the probe-analyte complexes. Impressively the probe has the potential to detect and quantify the Al (III) from market-available drug samples.

Dinuclear cadmium(II) complexes with distorted octahedral/monocapped trigonal prism coordination geometries: synthesis, crystal structure, DFT/TD-DFT calculation and photocatalytic degradation of methylene blue

Two Cd(II) complexes [Cd2(L1)2(dca)(NO3)] (1) and [Cd2(L2)2(SCN)(NO3)] (2) (HL1 = 2-methoxy-6-[(2-phenylamino-ethylimino)-methyl]-phenol; and HL2 = 2-[(2-ethylamino-ethylimino)-methyl]-6-methoxy-phenol), have been synthesized and characterized by single crystal structure analysis, IR and mass spectroscopic studies. Both the complexes 1 and 2 possess a triclinic crystal system with space group P1¯. In complex 1, geometry around one metal centre is distorted octahedral and other centre is distorted monocapped trigonal prism, whereas in complex 2, both the metal centres possess distorted octahedral geometries. Strong NH⋅⋅⋅O and weak aromatic CH⋅⋅∙O hydrogen bonding interactions in 1 and strong NH⋅⋅⋅O and NH⋅⋅⋅S hydrogen bonding in 2 results 1D and 2D supramolecular structures, respectively. Experimentally determined electronic spectral data have been compared with the calculated data obtained by DFT and TD-DFT calculation. Photocatalytic abilities of 1 and 2 have been examined by using spectroscopic technique and found that in presence of UV light both the complexes catalytically decomposed methylene blue by 54.0 % and 50.3 %, respectively.

What is the Limit Size of 2D Conjugated Extension on Central Units of Small Molecular Acceptors in Organic Solar Cells?

2D conjugated extension on central units of small molecular acceptors (SMAs) has gained great successes in reaching the state-of-the-art organic photovoltaics. Whereas the limit size of 2D central planes and their dominant role in constructing 3D intermolecular packing networks are still elusive. Thus, by exploring a series of SMAs with gradually enlarged central planes, it is demonstrated that, at both single molecular and aggerated levels, there is an unexpected blue-shift for their film absorption but preferable reorganization energies, exciton lifetimes and binding energies with central planes enlarging, especially when comparing to their Y6 counterpart. More importantly, the significance of well-balanced molecular packing modes involving both central and end units is first disclosed through a systematic single crystal analysis, indicating that when the ratio of central planes area/end terminals area is no more than 3 likely provides a preferred 3D intermolecular packing network of SMAs. By exploring the limit size of 2D central planes, This work indicates that the structural profiles of ideal SMAs may require suitable central unit size together with proper heteroatom replacement instead of directly overextending 2D central planes to the maximum. These results will likely provide some guidelines for future better molecular design.

(C8H6BrN2O)NO3: A Hybrid Nonlinear Optical Crystal With an Appropriate Birefringence

AbstractOrganic planar groups have recently been used to construct nonlinear optical materials because of their large hyperpolarizability, and then most of the products have birefringence which is unfavorable to phase matching. Here, a new organic–inorganic hybrid nonlinear optical crystal (C8H6BrN2O)NO3 is synthesized by combining the π‐conjugated organic [C8H6BrN₂O]+ cation and inorganic [NO3]− anion as the fundamental building blocks. Surprisingly, it not only shows a large second‐harmonic generation response of 3.8 times that of the commercial K2HPO4 crystals, but also has a moderate birefringence of 0.08 at 550 nm. Furthermore, it demonstrates high thermal stability up to 220 °C despite its hybrid material characteristics. Single crystal structure analysis and theoretical calculations confirm that the specific arrangement of NLO‐active [C8H6BrN₂O]+ groups with halogen branch chains and strong hydrogen bonding between two π‐conjugated groups leads to moderate birefringence and large frequency‐doubling effect. These findings provide a method to explore hybrid nonlinear optical crystals.

A Novel Homoconjugated Propellane Triimide: Synthesis, Structural Analyses, and Gas Separation.

Rigid three-dimensional (3D) polycyclic propellanes have garnered interest due to their unique conformational spaces, which display great potential use in selectivity, separation and as models to study through-space electronic interactions. Herein we report the synthesis of a novel rigid propellane, trinaphtho[3.3.3]propellane triimide, which comprises three imide groups embedded on a trinaphtho[3.3.3]propellane. This propellane triimide exhibits large bathochromic shift, amplified molar absorptivity, enhanced fluorescence, and lower reduction potential when compared to the subunits. Computational and experimental studies reveal that the effective through-space π-orbitals interacting (homoconjugation) occurs between the subunits. Single-crystal XRD analysis reveals that the propellane triimide has a highly quasi-D3h symmetric skeleton and readily crystallizes into different superstructures by changing alkyl chains at the imide positions. In particular, the porous 3D superstructure with S-shaped channels is promising for taking up ethane (C2H6) with very good selectivity over ethylene (C2H4), which can purify C2H4 from C2H6/C2H4 in a single separation step. This work showcases a new class of rare 3D polycyclic propellane with intriguing electronic and supramolecular properties.

Solvent Free, Selective Oxidation of Styrene Catalyzed by Cobalt Acylpyrazolone Supported onto Neutral Alumina: Synthesis and Spectral Characterization

AbstractThe present work describes the synthesis of the Cobalt acylpyrazolone complex supported over neutral alumina and its use as a heterogeneous catalyst for selective oxidation of styrene. The catalyst mentioned here was characterized by various physicochemical techniques such as FT‐IR, TGA, CV, SCXRD, PXRD and BET. This heterogeneous catalyst has successfully been used to oxidize styrene to benzaldehyde in a solvent‐free condition with good conversion (87 %) and high selectivity (90 %) using H2O2 and TBHP as oxidants. The effects of the reaction parameters (catalyst concentration, reaction duration, and temperature) have also been investigated. The existing complex was discovered to be recyclable and sustainable with no change in conversion or selectivity for benzaldehyde. FT‐IR spectra of the regenerated catalyst indicated that the catalyst was undegraded and stable after the reaction. The novel feature of the current work reported in this paper is the selective oxidation of styrene without the need for solvents under mild conditions. Single Crystal Analysis.

A Domino Protocol toward High-performance Unsymmetrical Dibenzo[d,d']thieno[2,3-b;4,5-b']dithiophenes Semiconductors.

Unsymmetric organic semiconductors have many advantages such as good solubility, rich intermolecular interactions for potential various optoelectronic applications. However, their synthesis is more challenging due to intricate structures thus normally suffering tedious synthesis. Herein, we report a trisulfur radical anion (S3⋅-) triggered domino thienannulation strategy for the synthesis of dibenzo[d,d']thieno[2,3-b;4,5-b']dithiophenes (DBTDTs) using readily available 1-halo-2-ethynylbenzenes as starting materials. This domino protocol features no metal catalyst and the formation of six C-S and one C-C bonds in a one-pot reaction. Mechanistic study revealed a unique domino radical anion pathway. Single crystal structure analysis of unsymmetric DBTDT shows that its unique unsymmetric structure endows rich and multiple weak S⋅⋅⋅S interactions between molecules, which enables the large intermolecular transfer integrals of 86 meV and efficient charge transport performance with a carrier mobility of 1.52 cm2 V-1 s-1. This study provides a facile and highly efficient synthetic strategy for more high-performance unsymmetric organic semiconductors.

A Domino Protocol toward High‐performance Unsymmetrical Dibenzo[d,d′]thieno[2,3‐b;4,5‐b′]dithiophenes Semiconductors

AbstractUnsymmetric organic semiconductors have many advantages such as good solubility, rich intermolecular interactions for potential various optoelectronic applications. However, their synthesis is more challenging due to intricate structures thus normally suffering tedious synthesis. Herein, we report a trisulfur radical anion (S3⋅−) triggered domino thienannulation strategy for the synthesis of dibenzo[d,d′]thieno[2,3‐b;4,5‐b′]dithiophenes (DBTDTs) using readily available 1‐halo‐2‐ethynylbenzenes as starting materials. This domino protocol features no metal catalyst and the formation of six C−S and one C−C bonds in a one‐pot reaction. Mechanistic study revealed a unique domino radical anion pathway. Single crystal structure analysis of unsymmetric DBTDT shows that its unique unsymmetric structure endows rich and multiple weak S⋅⋅⋅S interactions between molecules, which enables the large intermolecular transfer integrals of 86 meV and efficient charge transport performance with a carrier mobility of 1.52 cm2 V−1 s−1. This study provides a facile and highly efficient synthetic strategy for more high‐performance unsymmetric organic semiconductors.

Lanthanoid(Ⅲ) complexes containing bipyridinedicarboxylic acid ligand: Synthesis, spectroscopic characterization, thermal analysis, and crystal structures

The present report deals with the synthesis of the two complexes of respective formula {[Ce(bpydcb)(HCOO)(H2O)]·H2O}n (1) and [Eu2(bpydcb)3(H2O)2(DMF)]·3H2O·0.5DMF (2) the structure of both of them elucidated by single-crystal X-ray diffraction and powder X-ray diffraction to demonstrated that complexes 1 and 2 crystallize in a similar space group P21/c as a monoclinic system with high crystal purity. X-ray Single crystal diffraction analysis demonstrates, nine-coordinate environment of Ce (Ⅲ) in the complex 1 and octa-coordinate environment of Eu (Ⅲ) in the complex 2. And discovered the tricapped trigonal prism of cerium complex and the triangular dodecahedron of europium complex. Meanwhile, the complexes were characterized by elemental, infrared, ultraviolet, fluorescence and thermal analysis. Fluorescence testing shows that complex 1 emits ligand fluorescence, while complex 2 emits fluorescence from the ligand to the central ion, emitting characteristic fluorescence of europium ion, both complexes can emit strong fluorescence. The thermogravimetric analysis results show that the thermal stability of complex 1 is better than that of complex 2, and its organic framework only begins to collapse after 375 ℃.

Rational design of cuprofullerene bipyridine nanozyme with high peroxidase-like activity for colorimetric sensing of bleomycin.

The high catalytic activity of Cu-based nanozymes mainly depends on the efficient Fenton-like reaction of Cu+/ H2O2, but Cu+ cannot exist stably. Trying to find a material that can stably support Cu+ while promoting the electron cycle of Cu2+/Cu+ still faces serious challenges. C60 is expected to be an ideal candidate to solve this problem due to its unique structure and rich physicochemical properties. Here, we designed and synthesized a C60-doped Cu+-based nanozyme (termed as C60-Cu-Bpy) by loading high catalytic active site Cu+ onto C60 and coordinating with 2,2'-bipyridine (Bpy). The single crystal diffraction analysis and a series of auxiliary characterization technologies were used to demonstrate the successful preparation of C60-Cu-Bpy. Significantly, the C60-Cu-Bpy exhibited superior peroxidase-like activity during the catalytic oxidation of 3,3',5,5'-tetramethylbenzidine (TMB). Then, the catalytic mechanism of C60-Cu-Bpy as peroxidase was elucidated in detail, mainly benefiting from the dual function of C60. On the one hand, C60 acted as a carrier to directly support Cu+, which has the ability to efficiently decompose H2O2 to produce reactive oxygen species. The other was that C60 acted as an electron buffer, contributing to promoting the Cu2+/Cu+ cycle to facilitate the reaction. Furthermore, a colorimetric sensor for the quantitative analysis of bleomycin was established based on the principle of bleomycin specific inhibition of C60-Cu-Bpy peroxidase-like activity, with satisfactory results in practical samples. This study provides a new strategy for the direct synthesis of Cu+-based nanozymes with high catalytic performance.

Specific features of Copper(II) chloride complexes with Caffeine: Synthesis, Structure, DFT calculations

The present article is devoted to the consideration of the interconversions of copper(II) chloride complexes with caffeine (caf) ([CuII2(μ2-Cl)2(caf)2(H2O)2] (1),[CuII3(μ-Cl)6(caf)(H2O)]n (1a), [Cu4(μ2-Cl)6(μ4-O)(caf)4](1b), 2[CuII(caf)Cl2].0.25THF (1c), [CuII(caf)2Cl2] (2)), depending on the synthesis conditions, and to studies on the four-nuclear copper(II) bromide complex with acetamide (AcAm) ([Cu4(μ2-Br)6(μ4-O)(AcAm)4](3)). The results obtained have been confirmed by different methods (powder XRD, single crystal XRD analysis, IR-, ESI-MS-, EPR-spectroscopy, and magnetic properties studies). Two bromide ions in (3) are non-equivalent to the other four and this fact may result in the modification of the exchange integral between bonded copper ions. Single crystal XRD data have been compared with the results of DFT calculations. It has been found that the thermodynamic stability of the complexes grows with an increase in the number of copper atoms and bridging chloride ions and a decrease in the number of water molecules in the formula unit of the compound. The calculation results for complexes with acetamide are in a good correlation with those of caffeine and experimental data.

Synthesis of palladium complexes containing benzimidazole core and their catalytic activities in direct arylation of heteroaromatic species

Herein, we report the synthesis of four new palladium complexes containing a benzimidazole core and examine their catalytic activities in the direct arylation of heteroaromatic species with aryl bromides. The complexes were characterized by 1H and 13C NMR spectroscopy, FT-IR spectroscopy, and elemental analysis. In the 13C NMR spectra, NCHN peaks of Pd(II) complexes were observed between 143.2 and 144.9 ppm. Also, the structure of 2b was determined by single-crystal XRD analysis. The obtained data suggest that the lengths of the Pd–N and Pd–Cl bonds are like those of previous Pd complexes. Direct arylation reactions, using KOAc as base and DMAc as solvent under inert conditions, were carried out with the synthesized complexes in the presence of various aryl bromides, and 2-acetylthiophene, 2-furaldehyde, and 1-methylpyrole-2-carboxaldehyde. Moderate to high yields were obtained under 1% mol catalyst loading conditions. The results showed that electron-donating and electron-withdrawing substituents on the aryl halides may produce coupling products in good yields in the presence of 2a–d. These findings contribute to the synthesis and design of palladium complexes containing benzimidazole cores.

A new nor-neolignan compound identified from Itea yunnanensis

Various separation methods in combination with spectral data analysis, X-ray single crystal diffraction analysis, and litera-ture data comparison were employed to clarify the chemical constituents of Itea yunnanensis. Seven compounds were obtained from I. yunnanensis, which were identified as(S)-3-[1-(4-hydroxyphenyl)propane-2-yl]-4-methoxybenzoate methyl ester(1), iteafuranal B(2), syringaresinol(3), dihydrokaempferol(4), trimethoxybenzene(5), eicosane(6), and nonacosane(7), respectively. Among them, compound 1 was a new nor-neolignan compound named iteanorneoligan A, and the rest of the compounds were identified from I. yunnanensis for the first time. The anti-hepatocellular carcinoma effect of the compound was evaluated based on Sk-hep-1 cells model via MTT assay, and compound 2 showed a significant inhibitory effect on the proliferation of Sk-hep-1 cells with an IC_(50) of 9.4 μmol·L~(-1). The antioxidant capacity was determined via DPPH, ABTS~(·+), and O■ radical scavenging ability, and compound 1 exhibited a significant ABTS~(·+) radical scavenging effect with an IC_(50) of 0.178 mg·mL~(-1).