Light Yellow Crystals Research Articles

ISOLASI DAN UJI AKTIVITAS ANTIBAKTERI SENYAWA METABOLIT SEKUNDER DARI EKSTRAK METANOL DAUN MARPUYAN (Rhodamnia cinerea Jack.)

A study on isolation and antibacterial activity of secondary metabolites from the methanol extract of Marpuyan (Rhodamnia cinerea Jack.) Leaves on Escherichia coli has been carried out. Isolation was carried out by column chromatography methods. Whereas the antibacterial activity test was carried out using agar diffusion method. The results of the isolation produced 17.9 mg of RC-F13 isolate compound in the form of light yellow crystals, with a melting point of 170-172oC and soluble in methanol. The results of identification of RC- F13 isolate compounds through testing with AlCl3 reagents, positive including the flavonoid group, were strengthened by the results of the UV spectrum and FT-IR spectrum. Based on the results of the UV spectrum, it was seen that the RC- F13 isolate compound showed λ max 353.60, 257.00 and 209.20 nm. The FT-IR spectrum shows the presence of several functional groups such as OH, C aliphatic C-H, C = O carbonyl, C = C aromatic and C-O. testing the antibacterial activity of methanol extract with a concentration of 20%; 10%; 1%; 0.1% and 0.01%, fraction 13 at 1% concentration; 0.1% and 0.01% and RC- F13 isolate compound concentration of 0.1%, against Escherichia coli bacteria did not show any antibacterial activity which was marked by the absence of clear areas around the disc.

Matthiasweilite, PbTe4+O3, a New Tellurite Mineral from the Delamar Mine, Lincoln County, Nevada, USA

ABSTRACT Matthiasweilite (IMA2021-069), Pb2+Te4+O3, is a new mineral discovered at the Delamar mine, Lincoln County, Nevada, USA. It is a secondary mineral, associated with adanite, choloalite, northstarite, and other oxysalts in a quartz-rich matrix, that developed in an altered primary ore along with altaite, tetrahedrite-(Zn), native gold, and other sulfides and selenides. The mineral occurs as tightly intergrown masses of light yellow crystals. The streak is white, luster is adamantine, Mohs hardness is 2½, tenacity is brittle, and fracture is conchoidal; no obvious cleavage is present. The calculated density is 7.282 g/cm3 for the empirical formula. Data from electron probe microanalysis and assuming O = 3 gives the empirical formula Pb0.99Te4+1.01O3. Matthiasweilite is triclinic, space group P, with cell parameters a = 7.0256(4), b = 10.6345(6), c = 11.9965(8) Å, α = 78.513(6), β = 83.104(6), γ = 84.083(6)°, V = 869.10(9) Å3, and Z = 10. The crystal structure (R1 = 0.0523 for 3416 I > 2σI reflections) consists of Te4+O3 trigonal pyramids that are linked via relatively short (<2.6 Å) Pb–O bonds to form a framework.

Diversity of endophytic fungi from the root bark of Syzygium zeylanicum, and the antibacterial activity of fungal extracts, and secondary metabolite

Abstract. Syarifah, Elfita, Widjajanti H, Setiawan A, Kurniawati AR. 2021. Diversity of endophytic fungi from the root bark of Syzygium zeylanicum, and the antibacterial activity of fungal extracts, and secondary metabolite. Biodiversitas 22: 4572-4582. The decoction of the root bark of Syzygium zeylanicum has been used as traditional medicine, such as for treating pathogenic bacterial infections. Endophytic fungi that live in medicinal plant tissues have a high species diversity and biological activities correlate with their host. Therefore, this study aimed to explore the diversity of endophytic fungi from the root bark of S. zeylanicum and to determine the antibacterial activity of endophytic fungi and their secondary metabolites. In this study, we isolate and identify the endophytic fungi from the root bark of S. zeylanicum, continued by screening their antibacterial activity against two Gram-negative bacteria (Escherichia coli InaCCB5 and Salmonella thypi ATCC1048 and two Gram-positive bacteria (Staphylococcus aureus InaCCB4 and Bacillus subtilis InaCCB1204) by the Kirby-Bauer method. The fungal extract with the highest antibacterial activity proceeded with the isolation and determination of the structure of their bioactive compounds. The isolates were morphologically identified. Isolates that showed strong antibacterial activity were identified by molecular identification. Isolation of bioactive compounds was carried out by chromatographic techniques and the determination of the structure of pure chemical compounds was performed by the spectroscopic analysis. In total, there were 8 isolates of endophytic fungi were obtained from the root bark of S. zeylanicum, namely SZR1 – SZR8. SZR2 isolate has the highest antibacterial activity. Molecular identification through phylogenetic analysis showed that SZR2 isolate had high similarity with Penicillium brefeldianum. Isolation of bioactive compounds from SZR2 produced compound 1 in the form of light yellow crystals which showed strong antibacterial activity against S. typhi, E. coli, and B. subtilis with MIC values of 64 g/mL. Compound 1 was identified as p-hydroxybenzaldehyde, which was also obtained in its host. In conclusion, the endophytic fungus Penicillium brefeldianum produces similar secondary metabolites and antibacterial activity as its host plant.

Crystal structure of 4-(anthracen-9-yl)pyridine.

The title compound, C19H13N, which crystallizes in the monoclinic C2/c space group with one half-mol-ecule in the asymmetric unit, was synthesized by Suzuki-Miyaura cross-coupling reaction of 9-bromo-anthracene with pyridin-4-ylboronic acid and purified by column chromatography on silica gel. Light-yellow crystals of 4-(anthracen-9-yl)-pyridine suitable for X-ray diffraction were collected by the solvent evaporation method. In the crystal, pairs of mol-ecules are connected by inter-molecular C-H⋯π (pyridine) inter-actions [d(H7⋯Cg) = 2.7391 (2) Å], forming cyclic centrosymmetric dimers, further resulting in an infinite one-dimensional linear chain along the c-axis direction. Weak face-to-face π-π stacking inter-actions [d(Cg⋯Cg) = 3.6061 (2) Å] link neighboring lamellar networks into the supra-molecular structure.

The crystal structure and thermal decomposition kinetics of cis-hexanitrostilbene

Hexanitrostilbene (HNS) is an energetic material with wide application and excellent comprehensive performance. cis-HNS is successfully prepared using crude HNS with a purity of 95% as the raw material and N-methyl pyrrolidone (NMP) as the solvent. After separation and purification, acetone is used as a solvent to obtain light-yellow crystals at room temperature. The molecular structure of cis-HNS is determined through analysis of Fourier transform infrared, 13C NMR and 1H NMR spectroscopy and single-crystal X-ray diffraction data. The thermal decomposition properties of cis and trans-HNS are studied using differential scanning calorimetry (DSC). When the heating rate is low, cis-HNS will undergo a crystal transformation after melting, from liquid cis-HNS to liquid trans-HNS, and then it will solidify and release heat. According to the results of DSC data, the apparent kinetic parameters of thermal decomposition of cis- and trans-HNS were obtained by Kissinger method [Kissinger (1957). Anal. Chem. 29, 1702–1706] and Ozawa method [Ozawa (1965). Bull. Chem. Soc. Jpn. 38, 1881–1886], respectively. The spontaneous combustion temperature and self-accelerating decomposition temperature of cis and trans-HNS are calculated by the Zhang-Hu-Xie-Li method [Zhang et al. (1994). Thermochim. Acta, 244, 171–176].

Antimicrobial evaluation of Amyrin acetate from the stem bark of Ficus sycomorus (Moraceae)

In this study, the antimicrobial evaluation of alpha Amyrin obtained from the stem bark of ficus sycomorus was reported. Standard method was adopted for the screening of phyto-chemicals, while a combination of column and preparative thin layer chromatography lead to the compound (FA) a light yellow crystal. The compound FA showed significant inhibition on the tested organisms, E.coli (IC50 = 0.81) S. typhi (IC50= 0.84) S. aureus (IC50= 0.66) K. Pneumonia (IC50= 0.06) and was identified based on spectra evidence to contain a mixture of α-amyrin acetate.

Synthesis and antibacterial activity of 4-piperidone curcumin analogues against gram-positive and gram-negative bacteria

The rapid development of antibiotics resistance makes antibiotics become less effective for the treatment of bacterial infections. Accordingly, it is so important to discovery and development of new antibacterial agents. Three 4-piperidone curcumin analogues (3,5-bis-(2-chlorobenzylidene)-4-piperidone (1), 3,5-bis-(4-chlorobenzylidene)-4-piperidone (2) and 3,5-bis-(2,4-dichlorobenzylidene)-4-piperidone (3) were synthesized from 4-piperidone monohydrate hydrochloride with 2-chlorobenzaldehyde, 4-chlorobenzaldehyde and 2,4-dichlorobenzaldehyde. The Claisen-Schmidt condensation reaction was used in acid condition. All the compounds showed light yellow crystal with percentage of yield 39, 41 and 34% respectively. All the structure compounds were confirmed by using IR, 1H-NMR, 13C-NMR, and MS. The evaluation of antibacterial activity conducted by Agar diffusion method against Gram-positive bacteria such as Bacillus subtilis (ATCC 6633) and Enterococcus faecalis (ATCC 29212), and Gram-negative bacteria such as Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853). The result showed that all the compounds showed significant activity but they were more effective against Gram-positive bacteria as compared to their Gram-negative counterparts. Analogues curcumin compound showed that there was antibacterial activity up to concentration 62,5 μg/mL on Gram positive bacteria and 125 μg/mL on Gram negative bacteria. The compound 3,5-bis-(2,4-dichlorobenzylidene)-4-piperidone (3) containing two substituent -Cl on ortho and para position in the benzene ring has best activity than compound 1 and 2.

Genesis of Diamond in Metal–Carbon and Metal–Sulfur–Carbon Melts: Evidence from Experimental Data

The experimental data on diamond growth in the Fe–Ni–S–C and Fe–S–C systems with a sulfur content of 5–14 wt % at 5.5 GPa and 1300–1350°C are reported. Colorless and light yellow diamond crystals with a weight of 0.1–0.8 ct were synthesized. It is shown in the Fe–S–C system that at 5.5. GPa diamond may crystallize in a very narrow temperature range, from 1300 to 1370°C. Based on comparative analysis of the experimental data and the results of the study of native iron inclusions in natural diamonds from kimberlite pipes, it is suggested that diamond genesis may be partly controlled by the pre-eutectic (by the concentration of sulfur in relation to metal) metal–sulfide melt.

(C4C1Im)6[Hg7Se10]: The Salt of a Molecular Selenido Mercurate Anion Obtained from Ionic Liquids

A binary selenido mercurate anion exhibiting a novel metalate topology was obtained as its salt (C4C1Im)6[Hg7Se10] (1) upon treatment of the ternary selenido mercurate K2[Hg2Se3] in the ionic liquid (C4C1Im)[BF4] (C4C1Im = 1‐butyl‐3‐methylimidazolium) in the presence of small amounts of 1,2‐diaminoethane (en) at slightly elevated temperatures (80 °C). The three‐dimensionally extended anionic substructure was disassembled this way with formation of the unprecedented heptanuclear anion [Hg7Se10]6–. The light yellow crystals of 1 are extremely sensitive to air and moisture. The structure of 1 was determined by single‐crystal X‐ray diffraction, and its heavy element composition was analyzed and confirmed by micro X‐ray fluorescence spectroscopy (μ‐XFS).

A concise study on dimedone: A versatile molecule in multi-component reactions, an outlook to the green reaction media

Dimedone is an interesting and versatile motif in most organic transformations. Its white to light yellow crystals have been utilized as substrate in wide range of organic reactions including multi-component transformations. The notability of dimedone is due to the acidic property of its methylene group which is in equilibrium with its tautomeric enol form. This phenomena permit dimedone to be utilized in several kinds of organic reactions eventuated to several organic molecules with potent pharmaceutical exclusivity. The mentioned nature of dimedone in addition with its low toxicity, easily accessibility and handling, moisture stability, and low cost make it interesting for organic chemists. During the last decades, perfuming an organic transformation based on green chemistry rules, is in demand. In this review the reactions of dimedone has been focused with an outlook to the solvent of media. Each section has been subdivided respect to the temperature of the transformations. All categorizations has been accomplished to the green media. The authors has also calculated the atom economy of each reaction on behalf of green chemistry concept.

The Role of Connectivity on Electronic Properties of Lead Iodide Perovskite-Derived Compounds.

We use a layered solution crystal growth method to synthesize high-quality single crystals of two different benzylammonium lead iodide perovskite-like organic/inorganic hybrids. The well-known (C6H5CH2NH3)2PbI4 phase is obtained in the form of bright orange platelets, with a structure comprised of single ⟨100⟩-terminated sheets of corner-sharing PbI6 octahedra separated by bilayers of the organic cations. The presence of water during synthesis leads to formation of a novel minority phase that crystallizes in the form of nearly transparent, light yellow bar-shaped crystals. This phase adopts the monoclinic space group P21/n and incorporates water molecules, with structural formula (C6H5CH2NH3)4Pb5I14·2H2O. The crystal structure consists of ribbons of edge-sharing PbI6 octahedra separated by the organic cations. Density functional theory calculations including spin–orbit coupling show that these edge-sharing PbI6 octahedra cause the band gap to increase with respect to corner-sharing PbI6 octahedra in (C6H5CH2NH3)2PbI4. To gain systematic insight, we model the effect of the connectivity of PbI6 octahedra on the band gap in idealized lead iodide perovskite-derived compounds. We find that increasing the connectivity from corner-, via edge-, to face-sharing causes a significant increase in the band gap. This provides a new mechanism to tailor the optical properties in organic/inorganic hybrid compounds.

SYNTHESIS OF 3,5-DIBROMO- AND 2,4,5-TRIBROMO-1,8-NAPHTHALIMIDES

3,5-Dibromo-1,8-naphthalic acid and 2,4,5-tribromo-1,8-naphthalic acid were synthesized by oxidation of 1,5,7-tribromoacenaphthylene and 3,5,6-tribromoacenaphthylene by sodium dichromate in anhydrous acetic acid. The obtained naphthalic acids were heated for 2 hours at 110 °C, at which the acids were completely converted to corresponding naphthalic anhydrides with the overall yields of 53% and 45% respectively. Anhydrides were crystallized from acetic anhydride to form white needle crystals with melting points 207.5-208 °C and 222-223 °C for 3,5-dibromo-1,8-naphthalic anhydride and 2,4,5-tribromo-1,8-naphthalic anhydride respectively. 3,5-Dibromo-1,8-naphthalimide and 2,4,5-tribromo-1,8-naphthalimide were obtained by ammonolysis of corresponding anhydrides with aqueous ammonia solution. Formation of naphthalimide cycle takes place in several stages. At the first step ammonia molecule attacks the electrophilic carbon atom of carbonyl group with opening of the anhydride cycle following with proton migration from nitrogen to oxygen atom to form the monoamide of 1,8-naphthalenedicarboxylic acid. Further, the nitrogen atom of the amide group attacks the carbon atom of the carboxylic group to form a six-membered imide ring with cleaving the water molecule. Thus, the first stage of ammonolysis was carried out at room temperature to avoid the ammonia evaporation, the further cyclization reaction was carried out at 80 оC. 3,5-Dibromo-1,8-naphthalimide has been obtained by this procedure with the yield of 90 % as light yellow crystals with melting point 292-293 °C. In case of 2,4,5-tribromo-1,8-naphthalimide the product contained some unreacted 2,4,5-tribromo-1,8-naphthalic anhydride as impurity. The reaction mixture was treated with a 2% aqueous solution of sodium hydroxide to remove anhydride impurity. Target 2,4,5-tribromo-1,8-naphthalimide was obtained with the yield of 67 % as light yellow crystals with melting point > 300 °C. The structure of the synthesized naphthalimide derivatives has been confirmed by IR and NMR 1Н spectroscopy.

ChemInform Abstract: Crystal Growth and Structure of the Barium Chloride Nitridotantalate(V) Ba3Cl2TaN3.

AbstractTransparent, light yellow single crystals of the new title compound are obtained from the reaction of Ba(N3)Cl with the container wall of arc‐welded Ta ampules (900 °C, 4 d).

Crystal Growth and Structure of the Barium Chloride Nitrido­tantalate(V) Ba3Cl2TaN3

AbstractTransparent, light yellow single crystals of the barium chloride nitridotantalate(V) Ba3Cl2TaN3 (hexagonal, P63cm; a = 1507.39(8) pm, c = 632.98(3) pm, c/a = 0.420; Z = 6) are obtained by the reaction of the barium azide chloride Ba(N3)Cl or its ternary decomposition products with the container wall of arc‐welded tantalum ampoules at 900 °C after four days. Its crystal structure displays one‐dimensional chains 1∞{[TaN2/2N2/1]4–} consisting of corner‐sharing [TaN4]7– tetrahedra (d(Ta–N) = 191–200 pm), which run along [001] and arrange as hexagonal rod packing. Charge compensation of these parallel 1∞{[TaN3]4–} strands occurs via Ba2+ cations and Cl– anions erecting a three‐dimensional network 3∞{[Ba3Cl2]4+} (d(Ba–Cl) = 318–339 pm) with narrow channels apt to embed the chains. Several Ba–N contacts ranging between 264 and 319 pm secure the interconnection between both structural arrays and complete the coordination numbers of the Ba2+ cations to seven or eight.

Low-Molecular-Weight Compounds from Flowers of Apocynum lancifolium

Fifteen steroidal and phenolic compounds were previously isolated and identified from the EtOAc fraction of flowers of Apocynum lancifolium (Apocynaceae) collected in Xinjiang-Uyghur Autonomous Region, PRC [1]. In continuation of research on the chemical composition of flowers of A. lancifolium, we chromatographed the n-BuOH fraction over a column of AB-8 macroporous resin. Compounds were eluted sequentially by H2O and EtOH (30 and 80%). The two fractions obtained using EtOH (30 and 80%) were rechromatographed over a column of ODS-A 120c (octadecylsilyl silica gel) using MeOH–H2O mixtures (20, 40, 60, and 80% and MeOH) to produce five fractions. The eluates of all fractions were separated by chromatography over a column of Sephadex LH-20 using MeOH–H2O (1:1) and MeOH to isolate six known pure compounds, the chemical structures of which were elucidated using PMR, 13C NMR, and 2D spectra in addition a comparison with the literature. Umbelliferone (1). Colorless crystals, C9H6O3, mp 230°C. Compound 1 was identified as umbelliferone using spectral data [2]. Protocatechoic acid (3,4-dihydroxybenzoic acid) (2), C7H6O4, mp 200–202°C. Spectral data agreed with those published [3]. 1-(3,4-Dihydroxycinnamoyl)-cyclopentane-2 ,3 -diol (3). Light-yellow crystals, C14H16O6, [ ]D 20 –54.0° (c 0.1, DMSO), mp 128–130°C. 1H NMR spectrum (600 MHz, DMSO-d6, , ppm, J/Hz): 7.45 (1I, d, J = 15.8, H-7), 7.08 (1H, d, J = 1.7, H-2), 6.97 (1I, dd, J = 8.2, 1.7, H-6), 6.77 (1I, d, J = 8.2, H-5), 6.23 (1H, d, J = 15.8, H-8), 5.19 (1H, m, H-1 ), 3.94 (1H, br.s, H-3 ), 3.50 (1H, dd, J = 9.7, 2.3, H-2 ), 1.99 (1H, d, J = 12.2, H-4 ), 1.85 (2H, m, H-5 ), 1.70 (1H, m, H-4 ). 13C NMR spectrum (150 MHz, DMSO-d6, , ppm): 166.34 (N-9), 148.60 (N-4), 145.79 (N-3), 144.71 (N-7), 125.46 (N-1), 121.21 (N-6), 115.87 (N-5), 114.77 (N-2), 114.52 (N-8), 73.13 (N-2 ), 71.43 (N-1 ), 71.30 (N-3 ), 39.37 (N-5 ), 37.94 (N-4 ) [4]. L-Bornesitol (4). White crystals, C7H14O6, mp 210–212°C, [ ]D 20 –19.0° (c 0.1, DMSO). 1H NMR spectrum (600 MHz, DMSO-d6, , ppm, J/Hz): 4.58 (1I, d, J = 4.2, 5-II), 4.55 (1I, d, J = 4.5, 6-II), 4.51 (1I, d, J = 4.3, 4-II), 4.46 (1I, d, J = 3.6, 2-II), 4.40 (1I, d, J = 5.6, 3-II), 3.92 (1I, dd, J = 3.6, 2.6, I-2), 3.43 (1I, td, J = 9.4, 4.5, I-6), 3.34 (1I, td, J = 9.4, 4.3, I-4), 3.29 (3I, s, OCH3), 3.10 (1I, ddd, J = 9.7, 5.6, 2.6, I-3), 2.91 (1I, td, J = 9.3, 4.2, I-5), 2.82 (1I, dd, J = 9.7, 2.6, I-1). 13C NMR spectrum (150 MHz, DMSO-d6, , ppm): 81.71 (N-1), 68.31 (N-2), 71.73 (N-3), 72.49 (N-4), 75.32 (N-5), 71.81 (N-6), 56.65 (OCH3) [5]. 2D NOESY: H-1/H-3; 3-OH/6-OH, 5-OH, 4-OH; 4-OH/6-OH, 5-OH, 3-OH; 5-OH/6-OH, 4-OH, 3-OH; 6-OH/5-OH, 4-OH, 3-OH. Trifolin (kaempferol-3-O-D-galactoside) (5). Yellow powder, C21H20O11, mp 256–257°C. Acid hydrolysis of 5 produced kaempferol and -D-galactose. 1H NMR spectrum (600 MHz, DMSO-d6, , ppm, J/Hz): 8.07 (1H, d, J = 8.9, H-2 , 6 ), 6.86 (2H, d, J = 8.9, H-3 , 5 ), 6.42 (1H, d, J = 2.0, H-8), 6.19 (1H, d, J = 2.0, H-6), 5.40 (1H, d, J = 7.7, H-1 ), 3.66 (1H, br.s, H-4 ), 3.54 (1H, t, J = 8.6, H-2 ), 3.46 (1H, dd, J = 10.4, 6.0, H-6 ), 3.37 (1H, dd, J = 9.5, 3.0, H-3 ), 3.34 (1H, t, J = 6.0, H-5 ), 3.30 (1H, dd, J = 10.4, 6.0, H-6 ). 13C NMR spectrum (150 MHz, DMSO-d6, , ppm): 177.44 (C-4), 164.60 (C-7), 161.17 (C-5), 159.94 (C-4 ), 156.40 (C-9), 156.24 (C-2), 133.19 (C-3), 130.94 (C-2 ), 120.86 (C-1 ), 115.03 (C-3 ), 103.76 (C-10), 101.69 (C-1 ), 98.79 (C-6), 93.70 (C-8), 75.76 (C-5 ), 73.08 (C-3 ), 71.19 (C-2 ), 67.86 (C-4 ), 60.17 (C-6 ) [6].

Phenolic Constituents of Pulicaria gnaphaloides

In continuation of our research on the chemical constituents of Pulicaria gnaphaloides [1], we isolated eight phenolic compounds (1–8) using column chromatography of EtOAc fractions and elution by CHCl3 and a CHCl3–MeOH gradient (9:1 and 4:1). The structures of the isolated compounds were elucidated using spectral data (PMR, 13C NMR, DEPT, HSQC, HMBC, COSY) and comparisons with the literature in addition to direct comparison with authentic samples. They were identified as p-hydroxybenzoic acid (1), 3,4-dihydroxybenzoic acid methyl ester (2), luteolin (3), quercetin (4), isoquercitrin (5), hyperoside (6), rutin (7), and quercetin 3-rhamnosyl-(1 6)-galactoside (8). p-Hydroxybenzoic acid (1), C7H6O3, white crystals, mp 159.5°C. Compound 1 was identified as p-hydroxybenzoic acid using spectral data [2]. 3,4-Dihydroxybenzoic Acid Methyl Ester (2). C8H8O4, white crystals, mp 137–138°C. Its spectral data agreed with those published [2]. Luteolin (3). C15H10O6, light-yellow powder, mp 328–330°C. PMR and 13C NMR spectra agreed with those published [3]. Quercetin (4). C15H10O7, light-yellow crystals, mp 305–307°C. Spectral data and a comparison with the literature identified 4 as quercetin [2]. Isoquercitrin (5). C21H20O12, yellow powder, mp 248–250 C. 1H NMR spectrum (600 MHz, DMSO-d6, , ppm, J/Hz): 7.58 (1I, d, J = 1.8, H-2 ), 7.57 (1I, d, J = 9.0, I-5 ), 6.85 (1I, dd, J = 1.8; 9.0, H-6 ), 6.39 (1I, d, J = 2.4, I-8), 6.19 (1I, d, J = 2.4, I-6), 5.46 (1I, d, J = 7.8, I-1 ), 12.63 (1I, 5-II), 10.92 (1I, 7-II), 9.67 (1I, 4 -II), 9.41 (1I, 3 -II). 13C NMR spectrum (150 MHz, DMSO-d6, , ppm): 156.29 (N-2), 133.28 (N-3), 177.38 (N-4), 161.21 (N-5), 98.65 (N-6), 162.21 (N-7), 93.47 (N-8), 156.11 (N-9), 103.90 (N-10), 121.56 (N-1 ), 116.15 (N-2 ), 144.78 (N-3 ), 148.44 (N-4 ), 113.41 (N-5 ), 121.12 (N-6 ), 104.84 (N-1 ), 74.07 (N-2 ), 76.48 (N-3 ), 70.91 (N-4 ), 77.55 (N-5 ), 60.95 (N-6 ) [4]. Acid hydrolysis of 5 produced quercetin and D-glucose. Hyperoside (6). C21H20O12, yellow powder, mp 231–232°C. Acid hydrolysis detected quercetin and D-galactose [1]. Rutin (7). C27H30O16, yellow powder, mp 193–195°C. Acid hydrolysis of 7 produced quercetin, D-glucose, and L-rhamnose [5]. Quercetin 3-rhamnosyl-(1 6)-galactoside (8). C27H30O16, yellow powder, mp 186–188 C. 1H NMR spectrum (400 MHz, DMSO-d6, , ppm, J/Hz): 7.55 (2H, dd, J = 1.8, 8.5, H-2 , 6 ), 6.84 (1H, d, J = 8.5, H-5 ), 6.33 (1H, d, J = 2.0, H-8), 6.14 (1H, d, J = 2.0, H-6), 5.33 (1H, d, J = 7.5, H-1 ), 4.39 (1H, s, H-1 ), 1.01 (3H, d, J = 6.0, CH3-6 ), 3.04–3.40 galactose and rhamnose protons, 12.56 (1I, s, 5-II). 13C NMR spectrum (100 MHz, DMSO-d6, , ppm): 156.94 (N-2), 133.62 (N-3), 177.52 (N-4), 161.55 (N-5), 99.48 (N-6), 165.21 (N-7), 94.20 (N-8), 156.74 (N-9), 103.81 (N-10), 121.99 (N-1 ), 116.52 (N-2 ), 145.24 (N-3 ), 149.07 (N-4 ), 115.63 (N-5 ), 121.43 (N-6 ), 101.79 (N-1 ), 74.51 (N-2 ), 76.29 (N-3 ), 70.97 (N-4 ), 76.87 (N-5 ), 67.42 (N-6 ), 101.17 (N-1 ), 70.77 (N-2 ), 70.39 (N-3 ), 72.26 (N-4 ), 68.66 (N-5 ), 18.17 (N-6 ) [6]. Acid hydrolysis of 8 produced quercetin, D-galactose, and L-rhamnose. p-Hydroxybenzoic acid, 3,4-dihydroxybenzoic acid methyl ester, luteolin, quercetin, and quercetin 3-rhamnosyl(1 6)-galactoside were isolated for the first time from the genus Pulicaria; isoquercitrin and rutin, for the first time from Pulicaria gnaphaloides.

Anion-exchange and anthracene-encapsulation within copper(II) and manganese(II)-triazole metal-organic confined space in a single crystal-to-single crystal transformation fashion.

A new multidentate ligand 1-(9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl)-1H-1,2,4-triazole (tatrz) was designed and synthesized. Using tatrz as a building block, three novel coordination frameworks, namely, {[Cu(tatrz)2(NO3)2]·(CH3OH)·4H2O}n (1), {[Cu(tatrz)2(H2O)2](BF4)2}n (2), and [Mn(tatrz)2(SCN)2(CH3OH)]·2H2O (3) can be isolated. Anion-exchange experiment indicates that NO3(-) anions in the two-dimensional (2D) copper framework of 1 can be completely exchanged by ClO4(-) in an irreversible single crystal-to-single crystal (SC-SC) transformation fashion, as evidenced by the anion-exchange products of {[Cu(tatrz)2(H2O)2](ClO4)2·4CH3OH} (1a). Further, if 1a was employed as a precursor in N,N-dimethylformamide (DMF), an isomorphic solvate of {[Cu(tatrz)2(DMF)2](ClO4)2·2H2O}n (1b) can be generated during the reversible dynamic transformation process. When 1 was immersed in CH3OH, a distinct 2D layer {[Cu(tatrz)2(NO3)2]·4.4CH3OH·0.6H2O}n (1c) was isolated. Interestingly, the solvent-exchange conversion is also invertible between 1 and 1c, which exhibits spongelike dynamic behavior with retention of crystalline integrity. If the 2-fold interpenetrating three-dimensional (3D) framework 2 is selected, it can be transformed into another 2-fold interpenetrating 3D framework {[Cu(tatrz)2(H2O)2](ClO4)2·5.56H2O}n (2a) in a reversible SC-SC transformation fashion. However, when the light yellow crystals of mononuclear complex 3 were exposed to trichloromethane containing aromatic organic anthracene (atan), through our careful observation, the crystals of 3 were dissolved and reassembled into dark brown crystals of 2D crystalline coordination framework {[Mn(tatrz)2(SCN)2]·(atan)}n (3a). X-ray diffraction revealed that in 3a, atan acting as an organic template was encapsulated in the confined space of the 2D grid. Luminescent measurements illustrate that 3a is the first report of multidimensional polymers based on triazole derivatives as luminescent probes of Mg(2+).

Neue Sulfido-Antimonate der schweren Alkalimetalle: Synthese, Kristallstruktur und chemische Bindung von (K=Rb=Cs)3SbS3 und Cs3SbS4 · H2O / New Sulfido Antimonates of the Heavy Alkali Metals: Synthesis, Crystal Structure and Chemical Bonding of (K=Rb=Cs)3SbS3 and Cs3SbS4 · H2O

The new sulfido antimonates(III) (Rb=Cs)3SbS3 were prepared from the alkali metal sulfides Rb2S=Cs2S2 and elemental antimony and sulfur or Sb2S3 at reaction temperatures of about 700 °C. The known isotypic potassium compound was similarily synthesized from the elements. The structures of the light-yellow crystals were refined using single-crystal X-ray data. Both compounds are isotypic to the respective Na salt forming the Na3AsS3 structure type (cubic, space group P213, K/Rb/Cs: a = 947:21(7)=982:28(5)=1025:92(5) pm, Z = 4, R1 = 0:0159=0:0560=0:0582). The Ψ - tetrahedral SbS3- 3 anions with Sb-S bond lengths of 242 pm are arranged in a cubic face centered packing, in which the three crystallographically different A+ cations occupy the tetrahedral and octahedral voids, overall exhibiting a distorted octahedral sulfur coordination. The chemical bonding and the characteristics of the stereochemically active lone electron pair have been investigated by means of FP-LAPW band structure calculations. Needle-shaped crystals of the monohydrate of the antimony(V) salt Cs3SbS4 · H2O were obtained from a suspension of Sb2O3, CsOH and elemental sulfur. Cs3SbS4 · H2O crystallizes in a new structure type (monoclinic, space group P21/c, a = 987:17(10), b = 994:83(7), c = 1600:46(14) pm, β = 126:895(8)°, Z = 4, R1 = 0:0234). As expected, the Sb-S distances (233.1 - 234.7 pm) in the nearly ideally tetrahedral anion SbS3- 4 are considerably shorter than in the antimonates(III) but match the bond lengths in the anhydrous sulfido antimonate(V) Cs3SbS4. Due to their similar fcc-like anion packing and the stereochemically active lone electron pair of Sb in the antimonates(III), the whole series of compounds A3SbIII,VS3/4 shows a uniform structure relation, which is elucidated using crystallographic group-subgroup relations

Rosmarinic acid from eelgrass shows nematicidal and antibacterial activities against pine wood nematode and its carrying bacteria.

Pine wilt disease (PWD), a destructive disease for pine trees, is caused by the pine wood nematode (PWN), Bursaphelenchus xylophilus and additional bacteria. In this study, extracts of Zostera marina showed a high nematicidal activity against PWN and some of the bacteria that it carries. Light yellow crystals were obtained from extracts of Z. marina through solvent extraction, followed by chromatography on AB-8 resin and crystallization. The NMR and HPLC analysis showed that the isolated compound was rosmarinic acid (RosA). RosA showed effective nematicidal activity, of which the LC50 (50% lethal concentration) to PWN at 24 h, 48 h and 72 h was 1.18 mg/g, 1.05 mg/g and 0.95 mg/g, respectively. To get a high yield rate of RosA from Z. marina, single factor experiments and an L9 (34) orthogonal experiment were performed. This extraction process involved 70% ethanol for 3 h at 40 °C. The extraction dosage was 1:50 (w/v). The highest yield of RosA from Zostera was 3.13 mg/g DW (dried weight). The crude extracts of Zostera marina (10 mg/mL) and RosA (1 mg/mL) also showed inhibitory effects to some bacterial strains carried by PWN: Klebsiella sp., Stenotrophomonas maltophilia, Streptomyces sp. and Pantoea agglomerans. The results of these studies provide clues for preparing pesticide to control PWD from Z. marina.

Interstitial Incorporation of Plutonium into a Low-Dimensional Potassium Borate

The molten boric acid flux reaction of PuBr(3) with KBO(2) at 200 °C results in the formation of large light-yellow crystals of K[B(5)O(7)(OH)(2)]·H(2)O:Pu(4+). Single-crystal X-ray diffraction experiments on the Pu-doped K[B(5)O(7)(OH)(2)]·H(2)O demonstrate two features: (1) K[B(5)O(7)(OH)(2)]·H(2)O:Pu(4+) adopts a one-dimensional borate chain structure with void spaces between the chains. (2) The doping plutonium atoms do not reside on the potassium sites. The latter are not fully occupied. Both laser-ablation inductively coupled plasma mass spectrometry (LA-ICP-MS) and energy-dispersive spectrometry analyses indicate that plutonium atoms are uniformly distributed in crystals of K[B(5)O(7)(OH)(2)]·H(2)O with an atomic K:Pu ratio of approximately 65:1 measured by LA-ICP-MS. UV-vis-NIR spectra taken from both freshly made and one day old crystals show that the plutonium present within the crystals is predominantly characterized by Pu(IV). A small amount of Pu(III) is also present initially, but slowly oxidized to Pu(IV) via interaction with oxygen in the air. X-ray absorption near-edge structure and extended X-ray absorption fine structure spectroscopic measurements confirm that plutonium is mainly present as a form similar to that of a PuO(2) cluster. The combined results suggest that the clusters containing Pu(IV) ions are uniformly distributed in the void spaces between the borate chains.