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).

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 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.

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.

scholarly journals Targeted Isolation of Indole Alkaloids from Streptomyces sp. CT37

Molecules ◽  
2020 ◽  
Vol 25 (5) ◽  
pp. 1108 ◽  
Author(s):  
Qing Fang ◽  
Fleurdeliz Maglangit ◽  
Morgane Mugat ◽  
Caroline Urwald ◽  
Kwaku Kyeremeh ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Indole Alkaloids ◽  
Mass Spectrometric ◽  
Ionization Mass ◽  
Biosynthetic Pathways ◽  
Inhibition Activity ◽  
Streptomyces Sp ◽  
Moderate Growth ◽  
Nmr Data ◽  
Growth Inhibition Activity

Four compounds (1–4) were isolated from the extracts of Streptomyces sp. CT37 using bioassay in conjunction with mass spectrometric molecular networking (MN) driven isolation. Their complete structures were established by high-resolution electrospray ionization mass spectrometry (HR-ESIMS), and 1D and 2D nuclear magnetic resonance (NMR) data. Legonimide 1 was identified as a new alkaloid containing a rare linear imide motif in its structure, while compounds 2–4 were already known and their structures were elucidated as 1H-indole-3-carbaldehyde, actinopolymorphol B, (2R,3R)-1-phenylbutane-2,3-diol, respectively. The biosynthetic pathways of 1–4 were proposed based on the reported biogenesis of indole alkaloids in literature. Bioactivity tests for 1 and 2 revealed moderate growth inhibition activity against Candida albicans ATCC 10231 with MIC95 values of 21.54 µg/mL and 11.47 µg/mL, respectively.

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.

scholarly journals A new tetracyclic diterpenoid from the seeds of Euphorbia lathyris

2020 ◽  
Vol 44 (5-6) ◽  
pp. 322-325
Author(s):  
Lie-Feng Ma ◽  
Yue Zhang ◽  
Xuan Zhang ◽  
Meng-Jia Chen ◽  
Zha-Jun Zhan ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
High Resolution ◽  
Spectroscopic Data ◽  
Resonance Spectroscopy ◽  
Ionization Mass ◽  
Two Dimensional ◽  
Detailed Interpretation ◽  
A Minor ◽  
Euphorbia Lathyris

Eupholathone, a minor diterpenoid with an unusual tetracyclic skeleton, was obtained from the seeds of Euphorbia lathyris, along with two known lathyrane diterpenoids, euphorbia factors L2 and L3. The structure of eupholathone was elucidated by detailed interpretation of its spectroscopic data, especially two-dimensional nuclear magnetic resonance spectroscopy and high-resolution electrospray ionization mass spectrometry.

The Nature of Oxygen in Sporopollenin from the Pollen of Typha angustifolia L.

2000 ◽  
Vol 55 (3-4) ◽  
pp. 129-136 ◽  
Author(s):  
Friedhelm Ahlers ◽  
Henning Bubert ◽  
Stefan Steuernage ◽  
Rolf Wiermann
Keyword(s):  
Experimental Data ◽  
Nuclear Magnetic Resonance ◽  
Fourier Transform ◽  
Complex Structure ◽  
Resonance Spectroscopy ◽  
Hydroxyl Groups ◽  
Spectroscopic Methods ◽  
Typha Angustifolia ◽  
Ester Linkage ◽  
C Nmr

Abstract Native and peracetylated sporopollenin from the pollen of Typha angustifolia L. was investigated using several spectroscopic methods, inducing Fourier transform infrared spectroscopy (FTIR), solid-state 13C-nuclear magnetic resonance spectroscopy ( 13C-NMR) and Xray photoelectron spectrometry (XPS). Interpretation of the experimental data shows that the greater part of oxygen found in sporopollenin originates from hydroxyl groups and must be derived from aliphatics and not from aromatics. This result indicates that not only aromatics and long unbranched aliphatics but also poly-hydroxyl aliphatic components are involved in the complex structure of the polymer. Furthermore, it is most probable that the monomers of the sporopollenin skeleton are linked by ether- and not by ester-linkage. Two possible approaches are suggested for the characterisation of sporopollenin structure.

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