scholarly journals Antifungal and Antioxidant Pyrrole Derivative from Piper Pedicellatum

2013 ◽  
Vol 8 (10) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Chandan Tamuly ◽  
Partha P. Dutta ◽  
Manobjyoti Bordoloi ◽  
Jayanta Bora

In continuation of our search for efficient pest control natural products from the flora of the South Eastern Sub-Himalayan biodiversity region, we have investigated wild edible Piper pedicellatum C. DC (Piperaceae) from Arunachal Pradesh, India against five important plant pathogenic fungi through an activity guided method, and a new compound, pedicellamide, was isolated. The structure was determined on the basis of extensive spectroscopic studies and confirmed by X-ray crystallography. The compound exhibited antifungal activities against the phytopathogenic fungal organisms Rhizoctonia solani (MIC 38.4 ± 1.6 μg/mL), Fusarium oxysporum (MIC 29.7 ± 0.8 μg/mL), Aspergillus niger (MIC 48.6 ± 0.7 μg/mL), Puccinia gramini (MIC 46.8 ± 1.4 μg/mL) and Curvularia lunata (MIC 49.1 ± 0.1μg/mL). Additionally, the antioxidant potential of the compound was estimated by DPPH, ABTS and FRAP assay and found to be 2.87 ± 0.20, 2.19 ± 0.13 and 3.96 ± 0.17 VCEAC (μM/g), respectively.

2009 ◽  
Vol 64 (11-12) ◽  
pp. 790-792 ◽  
Author(s):  
Jin-Wen Shen ◽  
Bing-Ji Ma ◽  
Wen Li ◽  
Hai-You Yu ◽  
Ting-Ting Wu ◽  
...  

The methanolic extract of the fruiting bodies of the mushroom Armillariella tabescens was found to show antifungal activity against Gibberella zeae. The active compound was isolated from the fruiting bodies of A. tabescens by bioassay-guided fractionation of the extract and identifi ed as armillarisin B. Armillarisin B eventually corresponds to 2-hydroxy-2- phenylpropanediamide and its structure was confi rmed on the basis of spectroscopic studies including 2D NMR experiments.


1993 ◽  
Vol 71 (7) ◽  
pp. 1086-1093 ◽  
Author(s):  
Liqin Chen ◽  
Laurence K. Thompson ◽  
John N. Bridson

The preparation and properties of the thioether–pyridazine macrocycle (L4; C16H20S6N4) containing two pyridazine subunits, and its Cu(II), Cu(II)Cu(I), and Cu(I) complexes are described. The ligand is characterized by 1H nuclear magnetic resonance and mass spectrometry, and the complexes by infrared, eleetronic spectra, and magnetism, and in some cases by X-ray crystallography. The complex [Cu2(L4)Cl4]x, (1) crystallized in the triclinic system, space group [Formula: see text] with a = 8.6204(8) Å, b = 9.850(1) Å, c = 8.348(1) Å, α = 111.46(1)°, β = 102.50(1)°, γ = 71.818(9)°, V = 622.6(1) Å3, and Z = 1 (R = 0.043, Rw = 0.042 for 1312 reflections). Two monodentate pyridazine rings in the same ligand bind to one trans square-planar copper centre (CuN2Cl2) with two sulfurs from each ligand binding to another trans square-planar copper centre (CuS2Cl2) to form a polynuclear chain. The complex [Cu(L4)Cl2] (3) crystallized in the triclinic system, space group [Formula: see text] with a = 11.001(1) Å, b = 12.888(2) Å, c = 8.704(1) Å, α = 102.89(1)°, β = 103.36(1)°,γ = 75.84(1)°, V = 1145.8(3) Å3 and Z = 2 (R = 0.056, Rw = 0.044 for 2059 reflections). A trans square-planar structure (CuN2Cl2) exists for 3 with monodentate pyridazines. [Cu(L4)(NO3)2] (4) crystallized in the orthorhombic system, space group P212121, with a = 15.148(2) Å, b = 15.562(3) Å, c = 11.064(1) Å, V = 2608.2(7) Å3 and Z = 4 (R = 0.039, Rw = 0.034 for 1864 reflections). Two monodentate pyridazine rings and two bidentate nitrates bind to a pseudo-octahedral copper(II) centre.


2016 ◽  
Vol 11 (10) ◽  
pp. 1934578X1601101
Author(s):  
Shaojun Zheng ◽  
Longbo Li ◽  
Yu Wang ◽  
Rui Zhu ◽  
Hogjin Bai ◽  
...  

A series of 24 novel derivatives of the calycanthaceous alkaloids with a tetrahydropyrroloindol-based core structure was synthesized from tryptophan in good yields. Their structures were characterized by IR, 1H NMR, and 13C NMR spectroscopy and ESI-MS. The synthesized compounds were evaluated against a wide variety of plant pathogenic fungi. Compound a9 exhibited a high degree of activity against Curvularia lunata, with 91.0% activity at a concentration of 100 μg mL−1 and with an EC50 of 44.6 μg mL−1. a7, a8, a13, and a17 exhibited high degrees of activity against Sclerotinia sclerotiorum, with a8 being the most effective with an EC50 of 38.4 μg mL−1. Compound a9 illustrated activity against Botrytis cinerea, with an EC50 of 79.5 μg mL−1. Considering the compounds evaluated, the alkyl substituents of the chain may contribute to the significant variations in fungicidal potency. The structure antifungal activity relationships are also discussed. These results will pave the way for further design, structural modification, and development of calycanthaceous alkaloids as antimicrobial agents.


2005 ◽  
Vol 60 (10) ◽  
pp. 1021-1026 ◽  
Author(s):  
Khodayar Gholivand ◽  
Zahra Shariatinia ◽  
Mehrdad Pourayoubi ◽  
Sedigheh Farshadian

New diazaphospholes and diazaphosphorinanes with formula were synthesized and characterized by 1H, 13C, 31P NMR and IR spectroscopy and elemental analysis. The structure of compound 1 has been determined by X-ray crystallography. A one-dimensional polymeric chain was observed in the crystalline lattice produced by intermolecular -P=O. . .H-N- and -C=O. . .H-N-hydrogen bonds. Compounds 1 and 2 contain five-membered rings and show high values for 2J(PNH) and 2J(P,C) coupling constants due to the ring strain. These constants are reduced seriously in compounds with six-membered rings. In compound 6 with CCl3C(O)NH moiety, all phosphorus-hydrogen couplings are zero.


2009 ◽  
Vol 20 (3) ◽  
pp. 481-488 ◽  
Author(s):  
Khodayar Gholivand ◽  
Zahra Shariatinia ◽  
Sheida Ansar ◽  
Seyedeh Mahdieh Mashhadi ◽  
Farzaneh Daeepour

2003 ◽  
Vol 17 (2-3) ◽  
pp. 345-353 ◽  
Author(s):  
Eriko Mano ◽  
Hironari Kamikubo ◽  
Yasushi Imamoto ◽  
Mikio Kataoka

Photoactive yellow protein (PYP) is a photoreceptor protein for the negative phototaxis ofEctothiorhodospira halophila. The crystal structures of several photo‒intermediates have been revealed by X-ray crystallography. In the crystal structure of the active intermediate, PYPM, no significant structural changes were observed except for the vicinity of the chromophore. On the contrary, spectroscopic studies with solution condition demonstrated that global structural changes occur during the photo‒cycle. In order to reveal the origin of the discrepancies, we measured the reaction kinetics upon illumination under crystal condition and to compare them with those observed under solution condition. The reactive portion decreases with the increase of crystallinity. The rate constant of PYPMdecay also decreases with the increase of crystallinity. These results suggest two possibilities: (1) PYP in crystal does not react by the illumination; (2) the photoreaction rate is highly accelerated in crystal. Consequently, the photoreaction in crystal is considered to be highly influenced by the force constraint from crystalline lattice.


1992 ◽  
Vol 70 (7) ◽  
pp. 1886-1896 ◽  
Author(s):  
Liqin Chen ◽  
Laurence K. Thompson ◽  
John N. Bridson

The preparations of thioether–pyridazine macrocycles containing three (L1) and two (L2) pyridazine subunits and their copper complexes are described. The ligands are characterized by 1H nuclear magnetic resonance and mass spectrometry and in one case by X-ray crystallography, and the complexes by infrared, electronic, and electron spin resonance (esr) spectra and in some cases by X-ray crystallography. The complex [Cu3(L1)2Cl6]•2CHCl3 (1) crystallized in the triclinic system, space group [Formula: see text] with a = 13.661(2) Å, b = 14.174(3) Å, c = 9.412(2) Å, α = 101.08(2)°, β = 96.94(2)°, γ = 75.76(2)°, V = 1728.2(6) Å3, and Z = 2 (R = 0.056, Rw = 0.048 for 2080 reflections). Two monodentate pyridazine rings in each ligand bind to one square-planar copper centre with the third monodentate pyridazine in each ligand linking the two to the central square-planar copper. The complex [Cu(L2)Cl2] (2) crystallized in the orthorhombic system, space group Pnma, with a = 8.571(1) Å, b = 16.104(3) Å, c = 13.961(2) Å, V = 1927(1) Å3, and Z = 4 (R = 0.037, Rw = 0.033 for 1070 reflections). A cis square-planar structure exists for 2 with monodentate pyridazines. [Cu(L2)2]•(ClO4)2•CH3CN•CHCl3 (5) crystallized in the triclinic system, space group [Formula: see text] with a = 12.888(4) Å, b = 17.462(6) Å, c = 10.906(1) Å, α = 96.07(2)°, β = 104.18(2)°, γ = 94.51(2)°, V = 2352(1) Å3, and Z = 2 (R = 0.053, Rw = 0.044 for 2941 reflections). Two ligands involving monodentate pyridazine rings bind to a square-planar copper(II) centre. The protonated ligand salt [L2H](ClO4)•H2O (6) crystallized in the monoclinic system, space group P21/n, with a = 14.762(4) Å, b = 8.637(5) Å, c = 16.267(4) Å, β = 92.78(2)°, V = 2072(1) Å3, and Z = 4 (R = 0.064, Rw = 0.053 for 1456 reflections). No sulfur coordination is observed in these complexes and there is no apparent spin exchange in the trinuclear derivative.


Author(s):  
Ahmed A. Abdulrraziq ◽  
Sami M. Salih ◽  
Sultan F. Alnomasy ◽  
Ziyad M. Aldosari ◽  
Bader S. Alotaibi

Arum cyreniacum is an important member of the family of Araceae because of its bio-activities. Hence this work aimed to establish a link between Arum cyreniacum and its uses as bio-control against plant pathogenic fungi which had never hitherto been established. This work was carried out to evaluate the activity of the aqueous extracts of tubers, leaves, and flowers of Arum cyreniacum against three different types of pathogenic fungi, Fusarium solani, Rhizopus microspores and Aspergillus niger. The antifungal activity of the aqueous extracts of Arum cyreniacum was determined by poisoned food technique. The results showed that Arum cyreniacum had an inhibitory effect in a dose-dependent manner on Fusarium solani, Rhizopus microspores, while Aspergillus niger was resistant to all extracts. However, the great inhibition activity against tested fungi was associated with increasing concentrations of the aqueous extracts of Arum cyreniacum. Data in this work indicated that the use of Arum cyreniacum could be a valid alternative for bio-control of plant pathogenic fungi.


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