Synthesis and antifungal activity of dehydroabietic acid-based thiadiazole-phosphonates

Holzforschung ◽  
2015 ◽  
Vol 69 (9) ◽  
pp. 1069-1075 ◽  
Author(s):  
Nai-Yuan Chen ◽  
Wen-Gui Duan ◽  
Lu-Zhi Liu ◽  
Fang-Yao Li ◽  
Min-Ping Lu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Fourier Transform ◽  
Antifungal Activity ◽  
Positive Control ◽  
Dehydroabietic Acid ◽  
Ionization Mass ◽  
Vis Spectroscopy ◽  
Antifungal Effects ◽  
C Nmr

Abstract In search of new potent bioactive compounds, a series of dehydroabietic acid-based thiadiazole-phosphonate compounds were designed and synthesized by the Mannich-type reaction. All target compounds were characterized by Fourier transform infrared, 1H nuclear magnetic resonance (NMR), 13C NMR, 31P NMR, electrospray ionization-mass spectrometry, and UV-vis spectroscopy. The preliminary bioassay experiments showed that, at the concentration of 50 μg ml-1, some of the target compounds exhibited excellent antifungal activity against the five fungi tested, in which several compounds displayed even better antifungal effects than the commercial antifungal drug azoxystrobin, which served as the positive control in this study.

Synthesis and antifungal activity of camphoric acid-based acylhydrazone compounds

Holzforschung ◽  
2014 ◽  
Vol 68 (8) ◽  
pp. 889-895 ◽  
Author(s):  
Xian-Li Ma ◽  
Fang-Yao Li ◽  
Wen-Gui Duan ◽  
Jing-Ni Liao ◽  
Zhi-duo Lin ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Fourier Transform ◽  
Antifungal Activity ◽  
Magnetic Resonance ◽  
Electrospray Ionization ◽  
Condensation Reaction ◽  
Ionization Mass ◽  
Camphoric Acid ◽  
C Nmr

Abstract In the search of novel potent bioactive compounds, 18 novel camphoric acid-based acylhydrazone compounds 4a–4r were designed and synthesized by the condensation reaction of N-amino camphorimide (3) with substituted benzaldehyde based on camphoric acid as the starting material. The target compounds were characterized by means of Fourier transform infrared (FTIR), 1H nuclear magnetic resonance (NMR), 13C NMR, electrospray ionization-mass spectrometry (ESI-MS), and elemental analysis. The preliminary bioassay showed that the following camphoric acid-based compounds exhibited excellent antifungal activity with an inhibition ratio of 95% against Physalospora piricola at the concentration of 50 μg ml-1: o-bromophenyl acylhydrazone (4f), p-bromophenyl acylhydrazone (4g), p-methoxyphenyl acylhydrazone (4m), and p-hydroxyphenyl acylhydrazone (4p).

Synthesis and biological activities of α-pinene-based dithiadiazoles

Holzforschung ◽  
2014 ◽  
Vol 68 (1) ◽  
pp. 75-83 ◽  
Author(s):  
Gui-Shan Lin ◽  
Chang-Hua Ma ◽  
Wen-Gui Duan ◽  
Bo Cen ◽  
Fu-Hou Lei ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Fourier Transform ◽  
Brassica Campestris ◽  
Concentration Level ◽  
Biological Activities ◽  
Ionization Mass ◽  
Inhibition Activity ◽  
Growth Inhibition Activity ◽  
C Nmr

Abstract This work is aiming at the preparation of new bioactive compounds from α-pinene as starting material. To this purpose, the intermediates (disubstituted phenyl acylamino thioureas, class G) were cyclized to dithiadiazoles (class H). The intermediates and target compounds were analyzed by Fourier transform infrared, 1H nuclear magnetic resonance (NMR), 13C NMR, and electrospray ionization-mass spectrometry and elemental analysis. The bioassay experiments showed that the compounds G and H have herbicidal, fungicidal, and plant growth-regulating activities. The compounds 2,2′-dimethylphenyl thiadiazole and 3,3′-dimethylphenyl thiadiazole exhibited a growth inhibition activity of 72% and 68% against the root of rape (Brassica campestris L.) at a concentration of 100 μg ml-1 (60–79% inhibition level). The compound 4,4′-dichlorophenyl acylamino thiourea displayed an inhibition activity of 75% against Physalospora piricola at a concentration level of 50 μg ml-1 (60–79% inhibition level).

scholarly journals New Neolignan and Dihydrostilbene Derivatives from Pouzolzia sanguinea Inhibit NO Production in LPS-Activated BV2 Cells

2020 ◽  
Vol 15 (8) ◽  
pp. 1934578X2094836
Author(s):  
Le Thi Hong Nhung ◽  
Phan Thi Quyen ◽  
Trinh Thi Thuy ◽  
Nguyen Thanh Tam ◽  
Nguyen Thi Hoang Anh ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
High Resolution ◽  
Inhibitory Concentration ◽  
Soluble Fraction ◽  
Positive Control ◽  
No Production ◽  
Ionization Mass ◽  
Bv2 Cells ◽  
New Compounds

Three dihydrostilbene derivatives (1-3) and 5 neolignans (4-8) were isolated from the ethyl acetate-soluble fraction of Pouzolzia sanguinea. Two new compounds (1 and 4) were obtained. Their structures, as well as their absolute configuration, were elucidated by means of high-resolution electrospray ionization mass spectrometry, nuclear magnetic resonance, and circular dichroism spectral data. Compounds 1-8 inhibited NO production in lipopolysaccharide-activated BV2 cells with half-maximal inhibitory concentration (IC50) values ranging from 22.7 ± 1.5 to 61.2 ± 3.1 µM. Of these, compounds 1 and 2 exhibited the most NO inhibitory activity with IC50 values of 22.7 ± 1.5 and 25.1 ± 2.1 µM, respectively, in comparison with the positive control, NG-monomethyl-L-arginine, IC50 value 22.1 ± 1.2 µM.

scholarly journals Synthesis, Biomacromolecular Interactions, Photodynamic NO Releasing and Cellular Imaging of Two [RuCl(qn)(Lbpy)(NO)]X Complexes

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2545
Author(s):  
Luna Song ◽  
Hehe Bai ◽  
Chenyang Liu ◽  
Wenjun Gong ◽  
Ai Wang ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Confocal Imaging ◽  
Epr Spectra ◽  
Distorted Octahedral Geometry ◽  
Ionization Mass ◽  
Time Resolved ◽  
Pbr322 Dna ◽  
Vis Spectroscopy ◽  
No Release ◽  
Ft Ir

Two light-activated NO donors [RuCl(qn)(Lbpy)(NO)]X with 8-hydroxyquinoline (qn) and 2,2′-bipyridine derivatives (Lbpy) as co-ligands were synthesized (Lbpy1 = 4,4′-dicarboxyl-2,2′-dipyridine, X = Cl− and Lbpy2 = 4,4′-dimethoxycarbonyl-2,2′-dipyridine, X = NO3−), and characterized using ultraviolet–visible (UV-vis) spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, nuclear magnetic resonance (1H NMR), elemental analysis and electrospray ionization mass spectrometry (ESI-MS) spectra. The [RuCl(qn)(Lbpy2)(NO)]NO3 complex was crystallized and exhibited distorted octahedral geometry, in which the Ru–N(O) bond length was 1.752(6) Å and the Ru–N–O angle was 177.6(6)°. Time-resolved FT-IR and electron paramagnetic resonance (EPR) spectra were used to confirm the photoactivated NO release of the complexes. The binding constant (Kb) of two complexes with human serum albumin (HSA) and DNA were quantitatively evaluated using fluorescence spectroscopy, Ru-Lbpy1 (Kb~106 with HSA and ~104 with DNA) had higher affinity than Ru-Lbpy2. The interactions between the complexes and HSA were investigated using matrix assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF-MS) and EPR spectra. HSA can be used as a carrier to facilitate the release of NO from the complexes upon photoirradiation. The confocal imaging of photo-induced NO release in living cells was successfully observed with a fluorescent NO probe. Moreover, the photocleavage of pBR322 DNA for the complexes and the effect of different Lbpy substituted groups in the complexes on their reactivity were analyzed.

scholarly journals Antiviral 4-Hydroxypleurogrisein and Antimicrobial Pleurotin Derivatives from Cultures of the Nematophagous Basidiomycete Hohenbuehelia grisea

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2697 ◽  
Author(s):  
Birthe Sandargo ◽  
Benjarong Thongbai ◽  
Dimas Praditya ◽  
Eike Steinmann ◽  
Marc Stadler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Biological Activities ◽  
Virus Infectivity ◽  
Ionization Mass ◽  
Lead Compound ◽  
Resolution Electron ◽  
Mammalian Liver

4-Hydroxypleurogrisein, a congener of the anticancer-lead compound pleurotin, as well as six further derivatives were isolated from the basidiomycete Hohenbuehelia grisea, strain MFLUCC 12-0451. The structures were elucidated utilizing high resolution electron spray ionization mass spectrometry (HRESIMS) and 1D and 2D nuclear magnetic resonance (NMR) spectral data and evaluated for their biological activities; for leucopleurotin, we provide Xray data. While most congeners showed moderate antimicrobial and cytotoxic activity, 4-hydroxypleurogrisein emerged as an inhibitor of hepatitis C virus infectivity in mammalian liver cells.

Molecular characterization of petroporphyrins in crude oil by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry

2001 ◽  
Vol 79 (5-6) ◽  
pp. 546-551 ◽  
Author(s):  
Ryan P Rodgers ◽  
Christopher L Hendrickson ◽  
Mark R Emmett ◽  
Alan G Marshall ◽  
Mark Greaney ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Fourier Transform ◽  
Crude Oil ◽  
Electrospray Ionization ◽  
Cyclotron Resonance ◽  
Spectrometric Analysis ◽  
Ionization Mass ◽  
Ion Cyclotron Resonance ◽  
Ion Cyclotron ◽  
Ft Icr

Petroporphyrin compositional analysis of a heavy crude oil has been realized by isolation and subsequent ESI-FT-ICR mass spectrometric analysis of the porphyrin-containing fractions. Vanadium octaethyl (V=O(II)OEP) and nickel octaethyl (Ni(II)OEP) porphyrin standards were analyzed to determine favorable electrospray ionization conditions and provide insight as to the molecular species present (e.g., adducts, multimers). Standard V=O(II)OEP and Ni(II)OEP solutions revealed the presence of both monomer and dimer species with a greater relative abundance of monomers. In contrast, mass spectral analysis of a porphyrin fraction from Cerro Negro crude oil was dominated by dimeric species. MS3 analysis identified a dioctylphthalate (DOP) contaminant, likely introduced during fractionation of the crude oil. DOP-porphyrin complexes and porphyrin-porphyrin dimers were then identified. Infrared multiphoton dissociation (IRMPD) of dimeric species produced the corresponding monomers with minimal fragmentation. The monomeric petroporphyrins were analyzed to reveal the metal (Ni(II) or V=O(II)), porphyrin type (e.g., etio vs. DPEP), and distribution of alkylation.Key words: petroporphyrin, porphyrin, petroleum, electrospray ionization, mass spectrometry, Fourier transform, ion cyclotron resonance, ICR, FT-ICR, FTMS.

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