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The considerable blue shift of Csp2–H stretching frequency.

The presence of O–H⋯O/S conventional hydrogen bonds in the complex governs a significant blue shift of Csp2–H bonds.

Hydrogen bonds (H-bonds) in the complexes between aldehydes and hydrogen chalcogenides, XCHO...nH2Z with X = H, F, Cl, Br, and CH3, Z = O, S, Se, and Te, and n = 1,2, were investigated using high-level ab initio calculations. The Csp2-H...O H-bonds are found to be about twice as strong as the Csp2-H...S/Se/Te counterparts. Remarkably, the S/Se/Te-H...S/Se/Te H-bonds are 4.5 times as weak as the O-H...O ones. The addition of the second H2Z molecule into binary systems induces stronger complexes and causes a positive cooperative effect in ternary complexes. The blue shift of Csp2-H stretching frequency involving the Csp2-H...Z H-bond sharply increases when replacing one H atom in HCHO by a CH3 group. In contrast, when one H atom in HCHO is substituted with a halogen, the magnitude of blue-shifting of the Csp2-H...Z H-bond becomes smaller. The largest blue shift up to 92 cm-1 of Csp2-H stretching frequency in Csp2-H...O H-bond in CH3CHO...2H2O has rarely been observed and is much greater than that in the cases of the Csp2-H...S/Se/Te ones. The Csp2-H blue shift of Csp2-H...Z bonds in the halogenated aldehydes is converted into a red shift when H2O is replaced by a heavier analogue, such as H2S, H2Se, or H2Te. The stability and classification of nonconventional H-bonds including Csp2-H...Se/Te, Te-H...Te, and Se/Te-H...O have been established for the first time.

Surface-enhanced Raman spectroscopy (SERS) was employed to gain an understanding of the chemical enhancement mechanism of 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), an Agent Orange, adsorbed on a silver substrate surface. Experimental measurements were performed using a micro-Raman spectrophotometer with an excitation wavelength of 532 nm and successfully detected 2,4,5-T at a relatively low concentration of 0.4 nM. Density functional theory (DFT) calculations on the interactions of the 2,4,5-T molecule with some small silver clusters, Agn with n = 4, 8, and 20, as well as with extended Ag surfaces, demonstrate that the most stable adsorption configuration is formed via coordination of Cl9 sites and carbonyl C═O group on the 2,4,5-T ligand to the Ag atoms on surfaces. Analyses of charge transfer mechanism and frontier orbitals distributions show an electron transfer from 2,4,5-T to the cluster in the ground state, and an inversed trend occurs for the excited singlet state process, consequently leading to a chemical enhancement of SERS signals. The obtained results are of importance for subsequent work in guiding the design of mobile sensors specifically used for services of rapid screening and detection of these toxic compounds present in the environment, as well as agricultural and food products. Extensive computations pointed out that small silver clusters, in particular of Ag20 size, can be used as appropriate models for a metal nanoparticle surface.

Substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones have been prepared via three-component reactions and the tautomerism of these 3-pyrroline-2-ones is due to the slight difference of energy, and the significantly large rate constant of transformation between two tautomers. 1,4,5-Trisubstituted pyrrolidine-2,3-dione derivatives were prepared from the above mentioned 2-pyrrolidinone derivatives and aliphatic amines, which exist in enamine form and are stabilized by an intramolecular hydrogen bond. A possible reaction mechanism between 3-pyrroline-2-one and aliphatic amine (CH3NH2) was proposed based on computational results and the main product is formed favorably following the PES via the lowest ΔG # pathway in both the gas-phase and an ethanol solvent model. DFT calculations showed that kinetic selectivity is more significant than thermodynamic selectivity for forming main products. ispartof: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY vol:18 pages:1140-1153 ispartof: location:Germany status: published

Stable binary complexes of RCZOH⋯CH

A new benzofuran derivative, nervione (1), was isolated from Nervilia concolor (Blume) Schltr. (Orchidaceae). Eight previously reported compounds were also isolated: 5,7-dimethoxyflavone (2), 3,5,7-trimethoxyflavone (3), 7-methoxyflavone (4), 3,7-dimethoxy-5-hydroxyflavone (5), tetramethylscutellarein (4',5,6,7-tetramethoxyflavone) (6), 5,7-dimethoxy-4'-hydroxyflavone (7), rhamnetin (8), and 5,7-dihydroxy-3’,4’-dimethoxyflavone (9). The structures were elucidated by 1D, 2D NMR, and HRESIMS spectroscopy in addition to the literature. The relative configuration of 1 was defined using DP4+ probability while its absolute configuration was defined by comparison of the ECD spectrum of 1 with those of previously reported compounds. All isolated compounds were evaluated for alpha-glucosidase inhibition, revealing weak or no activity.

Chemical investigation on chloroform extract of Phlogacanthus turgidus led to the isolation of one new compound namely turgidol, together with five known triterpenoids, lupeol, lupenone, betulin, betulinic acid, and taraxerol. Their structures and stereochemistry have been determined by 1 D and 2 D NMR analysis, high resolution mass spectrometry, and compared with those in literatures. The relative configuration of turgidol was defined using DFT-NMR chemical shift calculations and subsequent DP4+ probability method. Turgidol, betulin, and betulinic acid were evaluated for cytotoxic activity toward K562 cancer cell line and the alpha-glucosidase inhibition.

Eight stable structures of nHCHO∙∙∙nH2O (n=1-3) were observed on potential surface energy at the MP2/aug-cc-pVDZ level of theory. All complexes were mainly stabilized by O-H∙∙∙O hydrogen bond and an additional contribution of Csp2-H∙∙∙O one. The larger positive cooperativity when adding H2O as compared to HCHO molecule is the most important factor in complex stabilization. The obtained results show that the O-H∙∙∙O is red-shifting hydrogen bond while Csp2-H∙∙∙O belongs to blue-shifting hydrogen bond. It is remarkable that an addition of H2O/HCHO into the binary system leads a Csp2-H bond contraction and an increase of its stretching frequency in Csp2-H∙∙∙O hydrogen bond, in which the larger marnitude of its blue-shifting enhancement is found as adding H2O molecule. This result is mainly governed by a decrease of electron density at σ*(Csp2-H) orbital and an increase in the s-character percentage of the Csp2 (Csp2-H).

In the study, we successfully decorated MnFe2O4 on BiVO4 to highly improve its photocatalytic activity for degradation of tetracycline as well as its magnetically recovery. The decoration of MnFe2O4 on BiVO4 led to formation of MnFe2O4/BiVO4 Z scheme heterojunction to effectively prevent the charge recombination in each material. Upon visible light, the MnFe2O4/BiVO4 heterojunction produced significant available amounts of e− and h+ existing in the conduction band of the MnFe2O4 and the valence band of the BiVO4, respectively. These produced e− on the conduction band of the MnFe2O4, which reduction potential was approximately −0.41 eV, exhibited strong reduction potential reducing oxygen to produce •O2− radicals while h+ on the valence band of the BiVO4, which oxidation potential was 2.77 eV, showed strong oxidation potential oxidizing water and hydroxyl groups to produce •OH radicals. These generated active oxygen radicals effectively degraded TC in water (~92%). The used photocatalysts were easily recovered from photocatalytic suspension using an external magnet due to high magnetically activity of the MnFe2O4, which tightly bonded with BiVO4 in the MnFe2O4/BiVO4 heterojunction. Finally, the recovered MnFe2O4/BiVO4 heterojunction was very active and stable for tetracycline degradation in long-term process.

A novel dimeric alkylresorcinol derivative, manilkzapotane (1), along with seven known compounds, lupeol acetate (2), lupeol (3), arjunolic acid (4), ergosterol peroxide (5), taraxerol (6), hederagonic acid (7), and glochidiol (8) were isolated from the stem bark of Manilkara zapota. Their structures were determined on the basis of spectroscopic data. DFT-NMR chemical shift calculations and a modified probability (DP4+) method were applied to define the relative configuration of 1. To the best of our knowledge, this represents the first isolation of a dimeric alkylresorcinol derivative from the Sapotaceae family.

g-C3N4/BiVO4, binary component heterojunction materials, were successfully synthesized for novel photocatalytic tetracycline (TC) decomposition. In the prepared binary component heterojunction, BiVO4 was well distributed on g-C3N4 layer. In addition, BiVO4 and g-C3N4 was intimately contacted. Both BiVO4 and g-C3N4, which band gap energies were approximately 2.46 and 2.71 eV, respectively, would also absorb significant amount of visible light to excite electrons (e−) from their valence bands to conduction bands. Thus, the e− on the conduction band of the BiVO4 could quickly transfer and combine with the h+ on the valence band of the g-C3N4. Therefore, the g-C3N4/BiVO4 could be easily excited by incident visible irradiation to produce large number of h+ on the valence band of the BiVO4 and e− on the conduction band of the g-C3N4. These produced e− and h+ were strong enough for reactions with water and oxygen to product huge amounts of hydroxyl radicals for novel TC degradation. The photocatalytic performance of these g-C3N4/BiVO4 materials highly depended on weight ratio of these used precursors. The g-C3N4/BiVO4-10 material, which the g-C3N4:BiVO4 weight ratio was 10%, presented the highest tetracycline degradation efficiency (95%). This was due to these excess of g-C3N4 covered more BiVO4 surface preventing incident light reaching to the material and also represented as active sites for recombination of charges (e− and h+) decreasing photocatalytic efficiency of the system. Finally, the synthesized g-C3N4/BiVO4 presented novel durability during long-term photocatalysis.

Surface enhanced Raman scattering (SERS) experiments and quantum chemical calculations (using density functional theory) on the interactions of chlorpyrifos (CPF), which is an intensively used pest...

A new diterpenoid, phyllane C (1), along with three known compounds, ovoideal E (2), spruceanol (3), and fluacinoid B (4) were isolated from the leaves of Phyllanthus acidus growing in Thailand. The structures were determined by analysis of their MS and NMR data as well as by comparison with literature values. DFT-NMR chemical shift calculations and subsequent DP4/DP4+ probability methods were applied to define the relative configuration of 1. Compound 3 showed a weak cytotoxicity against K562 cell line (IC50 41.9 ± 2.31 µg/mL).

This work is dedicated to theoretically investigate the formation process of C2H5OH···nCO2 (n = 1-5) complexes and to shed light on the nature of interactions formed under the variation of CO2 concentration. It is found that CO2 molecules tend to locate around the polarized -OH group to interact with the lone pairs of the O atom. The interaction of ethanol with three CO2 molecules (C2H5OH···3CO2) induces the most stable structure in the sequence considered. The atoms in molecules (AIM), NCIplot, and natural bond orbital (NBO) analyses point out that the Oethanol···CCO2 tetrel bond overcomes hydrogen, chalcogen, and CO2···CO2 tetrel-bonded interactions and mainly contributes to the strength of C2H5OH···nCO2 (n = 1-5) complexes. All intermolecular interactions in the examined complexes are weakly noncovalent, and their positive cooperativity is evaluated to be slightly weaker than that of CO2 pure systems. SAPT2+ and molecular electrostatic potential (MEP) calculations indicate that the electrostatic force is the main factor underlying the attractive interplay in the complexes of C2H5OH and CO2.

Structural transformation is a unique characteristic of atomic clusters, but it turns out very different from cluster to cluster. This theoretical study proves that the isomeric transformation between hexagonal prism and hexagonal antiprism is found for the doubly doped Cr2Ge12 cluster but not for singly doped CrGe12 cluster. We confirm that the ground state of CrGe12 is the distorted hexagonal prism C2h at the 3Bg triplet state instead of various shapes predicted in the previous studies. Upon comparison between the estimation at the B3P86/6-311+G(d) level of theory and the detachment energies measured by photoelectron spectroscopy, hexagonal antiprismatic shape is identified as the most stable isomer of the Cr2Ge12 cluster and it is easy to transform to the hexagonal prism-a less stable isomer by the rotation of the hexagonal rings. That is the first evidence for the structural transformation between a hexagonal prism and an antiprism of the germanium clusters, referring to the ability of Ge-based clusters in the formation of tubular geometry by doping Cr atoms. All the low-energy isomers of both Cr-doped germanium clusters have high magnetic moments. Interestingly, there is a tuning in magnetic properties of Cr2Ge12 from the ferromagnetism of the lowest-lying hexagonal antiprism to the ferrimagnetism of the higher-energy hexagonal prism. The stronger Cr-Cr bond and stronger interaction between the Cr2 moiety and the antiprism cage are accounted for by the higher stability of the hexagonal antiprismatic isomer.

One new hopane-type triterpene, indicuen (

Geometrical structure, stability and cooperativity, and contribution of hydrogen bonds to the stability of complexes between chalcogenoaldehydes and water were thoroughly investigated using quantum chemical methods. The stability of the complexes increases significantly when one or more H

Two new cycloartanes, combretanones G and H (1 and 2), were isolated from the leaves of Combretum quadrangulare. Their structures were elucidated by applying a set of spectroscopic methods, while their relative configurations were determined using DFT-NMR chemical shift calculations and subsequent assignment of DP4 probabilities. Compounds 1 and 2 are C-23/C-24 stereoisomers of the previously-reported euphonerin E. Both exhibited moderate cytotoxicity against three human cancer cell lines. Compound 2 was shown to be a potent antiparasitic. Our results confirm the traditional medicinal uses of Combretum quadrangulare in Vietnam.

A new benzofuran derivative, nervione (

Chemical investigation on chloroform extract of

Flavonoids provide potential health benefits due to their antioxidant properties. The antioxidant activity of natural flavonoids is primarily exerted by phenolic hydroxyl groups; however, C–H bonds also contribute to these properties. In this study, the contributions of phenolic groups and C–H bonds to the antioxidant properties of 13 flavonoids were investigated by using the (RO)B3LYP/6-311++G(2df,2p)//B3LYP/6-311G(d,p) model chemistry in the gas phase and water and ethanol solvents. It was found that the C–H bonds have lower bond dissociation energies than O–H bonds in the 4-carbonyl and/or 3-hydroxyl group containing flavonoids and hence define antioxidant activity. The HOO· radical scavenging of the selected flavonoids is also investigated in detail through the potential energy surface, natural bond orbitals, and kinetic calculations. It was found that the favored radical scavenging mechanism of the flavonoids is hydrogen atom transfer, with the gas phase rate constants in the range of 7.23 × 103–2.07 × 109 L·mol–1·s–1. The results suggest that the flavonoids, isomelacacidin, isoteracacidin, melacacidin, and teracacidin, have antioxidant properties as high as typical phenolic compounds such as quercetin, trans-resveratrol, trolox, and ascorbic acid.

The methanol extract of Olax imbricata roots afforded one new sesquiterpenoid tropolone and three new 1,2,3,4-tetrahydronaphthalene derivatives, olaximbrisides A–D (1–4). Their structures were determined by 1D and 2D NMR experiments in combination of HRESIMS. The relative configurations were assigned by the NOESY experiments. The absolute configurations were established by a combination of X-ray diffraction analysis and electronic circular dichroism (ECD) experiments. All isolated compounds were evaluated for their cytotoxic effects against some cancer cell lines. Among them, compound 1 exhibited the cytotoxicities against MCF-7, HepG2 and LU cell lines with IC50 values of 16.3, 34.3 and 8.0 μM, respectively.

One new hopane-type triterpene, indicuen (1), along with eight known compounds (2���9) were isolated from the n-hexane extract of the lichen Parmotrema indicum Hale. The chemical structures of isolated compounds were identified by interpretation of their spectroscopic data (1D, 2D NMR and HRESIMS) combined with DFT-NMR chemical shift calculations and subsequent assignment of DP4+ probabilities and by comparison with the literature. Indicuen represents for a rare hopane bearing a 1-carboxyethyl substituent at C-21 in lichens. Compounds 1���3 and 5���8 were evaluated for ��-glucosidase inhibition and cytotoxicity against K562 and HepG2 cancer cell lines. Compounds 1, 5 and 7 exhibited moderate ��-glucosidase inhibition with IC50 values of 201.1, 156.3 and 187.4 ��M, respectively. Compound 1 also showed weak cytotoxicity toward K562 cell line while others showed no activity.

Chemical investigation of chloroform extract of

A novel dimeric alkylresorcinol derivative, manilkzapotane (

From the leaves of

A new diterpenoid, phyllane C (

Stabilization for tetrylone complexes, which carry ylidone(0) ligands [(CO)5W-X (YCp*)2] (X = Ge, Sn, Pb; Y = B-Tl), has become an active theoretical research because of their promising application. Structure, bonding, and quantum properties of the transition-metal donor-acceptor complexes were theoretically investigated at the level of theory BP86 with several types of basis sets including SVP, TZVPP, and TZ2P+. The optimized structures reveal that all ligands X (YCp*)2 are strongly bonded in tilted modes to the metal fragment W(CO)5, and Cp* rings are mainly η5-bonded to atom X. DFT-based bonding analysis results in an implication that the stability of W-X bond strength primarily stems from the donation (CO)5W ← X(YCp*)2 formed by both σ- and π-bondings and the electrostatic interaction ΔE elstat. The W-X bond possesses a considerable polarizability toward atom X, and analysis on its hybridization is either sp2-characteristic or mainly p-characteristic. EDA-NOCV-based results further imply that the ligands XY perform as significant σ-donors but minor π-donors. The visual simulations of NOCV pairs and the deformation densities assemble a comprehensive summary on different components of the chemical bond via σ- and π-types in the complexes. This work contributes to the literature as an in-depth overview on predicted molecular structures and quantum parameters of the complexes [(CO)5W-X(YCp*)2] (X = Ge, Sn, Pb; Y = B-Tl), conducive to either further theoretical reference or extending experimental research.

GC-MS was applied to identify 24 main substances in Melaleuca cajuputi essential oil (TA) extracted from fresh cajeput leaves through steam distilling. The inhibitory capability of active compounds in the TA from Thua Thien Hue, Vietnam over the Angiotensin-Converting Enzyme 2 (ACE2) protein in human body - the host receptor for SARS-CoV-2 and the main protease (PDB6LU7) of the SARS-CoV-2 using docking simulation has been studied herein. The results indicate that the ACE2 and PDB6LU7 proteins were strongly inhibited by 10 out of 24 compounds accounting for 70.9% in the TA. The most powerful anticoronavirus activity is expressed in the order: Terpineol (TA2) ≈ Guaiol (TA5) ≈ Linalool (TA19) > Cineol (TA1) > β-Selinenol (TA3) > α-Eudesmol (TA4) > γ-Eudesmol (TA7). Interestingly, the synergistic interactions of these 10 substances of the TA exhibit excellent inhibition into the ACE2 and PDB6LU7 proteins. The docking results orient that the natural Melaleuca cajuputi essential oil is considered as a valuable resource for preventing SARS-CoV-2 invasion into human body.

Two new lindenane sesquiterpenes were obtained from the roots of Lindera myrrha. These compounds were structurally elucidated by HRMS data, extensive NMR analyses, and comparison between experimental and theoretical 13C-NMR data. Myrrhalindenane A is the first monomeric seco-d lindenane displaying a non-rearranged, cyclohexanic C-ring. Myrrhalindenane B is the second occurrence of an angular lindenane-sesquiterpene related to a C6-C7 lactonization.

This work is dedicated to theoretically investigate the formation process of C2H5OH···nCO2 (n = 1–5) complexes and to shed light on the nature of interactions formed under the variation of CO2 concentration. It is found that CO2 molecules tend to locate around the polarized −OH group to interact with the lone pairs of the O atom. The interaction of ethanol with three CO2 molecules (C2H5OH···3CO2) induces the most stable structure in the sequence considered. The atoms in molecules (AIM), NCIplot, and natural bond orbital (NBO) analyses point out that the Oethanol···CCO2 tetrel bond overcomes hydrogen, chalcogen, and CO2···CO2 tetrel-bonded interactions and mainly contributes to the strength of C2H5OH···nCO2 (n = 1–5) complexes. All intermolecular interactions in the examined complexes are weakly noncovalent, and their positive cooperativity is evaluated to be slightly weaker than that of CO2 pure systems. SAPT2+ and molecular electrostatic potential (MEP) calculations indicate that the electrostatic force is the main factor underlying the attractive interplay in the complexes of C2H5OH and CO2.

Eighteen active substances, including 17 organosulfur compounds found in garlic essential oil (T), were identified by GC-MS analysis. For the first time, using the molecular docking technique, we report the inhibitory effect of the considered compounds on the host receptor angiotensin-converting enzyme 2 (ACE2) protein in the human body that leads to a crucial foundation about coronavirus resistance of individual compounds on the main protease (PDB6LU7) protein of SARS-CoV-2. The results show that the 17 organosulfur compounds, accounting for 99.4% contents of the garlic essential oil, have strong interactions with the amino acids of the ACE2 protein and the main protease PDB6LU7 of SARS-CoV-2. The strongest anticoronavirus activity is expressed in allyl disulfide and allyl trisulfide, which account for the highest content in the garlic essential oil (51.3%). Interestingly, docking results indicate the synergistic interactions of the 17 substances, which exhibit good inhibition of the ACE2 and PDB6LU7 proteins. The results suggest that the garlic essential oil is a valuable natural antivirus source, which contributes to preventing the invasion of coronavirus into the human body.

From the leaves of Ricinus communis Linn., one new alkaloid, named ricicomin A (1) together with three known ones, ricinine (2), N-demethylricinine (3) and 4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoic acid (4) were justified by repeated chromatographic methods. Their structures were determined by comprehensive IR, HR-ESI-MS and NMR analyses. Compound 4 was identified for the first time from the genus Ricinus. DFT-NMR chemical shift calculations and subsequent DP4+ probability methods were applied to confirm the chemical structure of 1. Compounds 1–3 did not display cytotoxic effect against three human cancer cell lines (MCF-7, HepG2 and HeLa) using SRB assay.

Ribavirin and remdesivir have been preclinically reported as potential drugs for the treatment of SARS-CoV-2 infection, while light silver tetrylene complexes (NHEPh–AgCl and (NHEPh–AgCl)2 with E = C, Si, and Ge) have gained significant interest due to their promising applicability on the cytological scale. Firstly, the structures and bonding states of silver–tetrylene complexes (NHE–Ag) and bis-silver–tetrylene complexes (NHE–Ag-bis) were investigated using density functional theory (DFT) at the BP86 level with the def2-SVP and def2-TZVPP basis sets. Secondly, the inhibitory capabilities of the carbene complexes (NHC–Ag and NHC–Ag-bis) and the two potential drugs (ribavirin and remdesivir) on human-protein ACE2 and SARS-CoV-2 protease PDB6LU7 were evaluated using molecular docking simulation. The carbene ligand NHC bonds in a head-on configuration with AgCl and (AgCl)2, whereas, the other NHE (E = Si and Ge) tetrylene ligands bond in a side-on mode to the metal fragments. The bond dissociation energy (BDE) of the NHE–Ag bond in the complex families follows the order of NHC–Ag > NHSi–Ag > NHGe–Ag and NHSi–Ag-bis > NHGe–Ag-bis > NHC–Ag-bis. The natural bond orbital analysis implies that the [NHEPh→AgCl] and [(NHEPh)2→(AgCl)2] donations are derived mainly from the σ- and π-contributions of the ligands. The docking results indicate that both the ACE2 and PDB6LU7 proteins are strongly inhibited by silver–carbene NHC–Ag, bis-silver–carbene NHC–Ag-bis, ribavirin, and remdesivir with the docking score energy values varying from −17.5 to −16.5 kcal mol−1 and −16.9 to −16.6 kcal mol−1, respectively. The root-mean-square deviation values were recorded to be less than 2 A in all the calculated systems. Thus, the present study suggests that silver–carbene NHC–Ag and bis-silver–carbene NHC–Ag-bis complexes are potential candidates to inhibit ACE2 and PDB6LU7, and thus potentially conducive to prevent infection caused by the SARS-CoV-2 virus.

Structural transformation is a unique characteristic of atomic clusters, but it turns out very different from cluster to cluster. This theoretical study proves that the isomeric transformation between hexagonal prism and hexagonal antiprism is found for the doubly doped Cr

Four stable configurations were found upon adsorption of the chloramphenicol on a period slab model of the vermiculite surface, using the PBE and C09-vdW functionals in a projector-augmented wave (PAW) method approach. The adsorption is a strong chemisorption process, characterized by an adsorption energy of −106.5 kcal mol−1 at the most stable configuration. Stability of configurations contributed mainly by Mg⋯O/Cl attractive electrostatic interactions and C/O H⋯O hydrogen bonds. It is remarkable that the vermiculite is found to be a solid material with good potential to be used for adsorption and consequent removal of this type of antibiotic drugs.

A new labdane-type diterpenoid, 9-epi-vitexnegundin (1), was isolated from the leaves of Vitex negundo L. together with seven known compounds: 8,13-diepi-manoyl oxide (2), 8-epi-sclareol (3), sclareol (4), 9,13-epoxy-labd-14-ene (5), vitedoin B (6), argyol (7), and predicularis-lactone (8). The chemical structures were elucidated by analysis of spectroscopic data and comparison with published NMR data. The DP4+ probability method was used to determine the relative stereochemistry of 9-epi-vitexnegundin. Complete NMR assignments of compound 2 were determined, revising the previously-reported NMR data for this compound. The stereochemistry of 9,13-epoxy-labd-14-ene (5) was elucidated for the first time, based on NOESY correlations. All isolated compounds 1–8 were evaluated for cytotoxicity against the K562 cell line, as were vitexnegundin (9), vitexilactone (10), vitetrifolin D (11), 13-hydroxy-5(10), 14-halimadien-6-one (12), artemetin (13), vitexicarpin (14), penduletin (15). Compounds 10–15 exhibited moderate cytotoxicity, with IC50 values in the range 15.7–79.8 µM.

A benzothiazolium-derived colorimetric and fluorescent chemosensor (L) for mercury ions has been prepared. The detection limits of the colorimetric and fluorescent method are 15.3 and 11.8 ppb, respectively, much lower than the reported chemosensors based on similar derivatives of benzothiazolium. The optimized molecular structures, absorption and fluorescence characteristics of the chemosensor and its complex with mercury ions were performed using calculations at the B3LYP/LanL2DZ level of theory, in combination with Atoms in Molecules and Natural Bond Orbitals analyses.