scholarly journals Microbial Transformation of Some Natural and Synthetic Aromatic Compounds by Fungi: Aspergillus and Neurospora Strains

2017 ◽  
Vol 12 (8) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Nurunajah Ab Ghani ◽  
Nor Hadiani Ismail ◽  
Yoshiaki Noma ◽  
Yoshinori Asakawa

Microbial transformation of chalcone (1), 4-hydroxychalcone (2) and 4′-hydroxychalcone (3), 1,1-diphenylmethane (4), 1,3-diphenylacetone (5), 1,3-diphenylpropane (6), bibenzyl (7), ( E)-stilbene (8a)- and ( Z)-stilbenes (8b), and phenylcyclohexane (9), (1 R,2 S)-1-phenyl-2-hydroxycyclohexane (9a) and (1 S,2 R)-1-phenyl-2-hydroxycyclohexane (9b), and a naturally occurring bis-bibenzyl, marchantin A (10) were performed by using Aspergillus niger TBUYN-2 and the other Aspergillus strains, and Neurospora crassa which were capable to hydrogenation and epoxidation of a conjugated double bond, and direct hydroxylation and hydroperoxidation on benzene ring, and hydroxylation and carbonization on cyclohexane ring. Aspergillus species converted chalcone (1) to dihydrochalcone (1a) almost quantitatively.

2018 ◽  
Vol 13 (8) ◽  
pp. 1934578X1801300
Author(s):  
Yoshinori Asakawa ◽  
Masako Sekita ◽  
Toshihiro Hashimoto

Microbial biotransformation of naturally occurring pungent sesquiterpene 1,2-dials, polygodial and cinnamodial, and a diterpene 1,2-dial, sacculatal as well as their tetrahydro derivatives was carried out by using Aspergillus niger. The pungent polygodial and sacculatal are toxic against A. niger not to produce any metabolites while A. niger biotransformed cinnamodial to the lactonized products in small amount. On the other hands, the dihydroxy derivatives of the former two dialdehydes were bioconverted by the same fungus to give hydroxy-, oxo-, carboxylic- and epoxy-products. The stereostructures of each metabolite and their metabolic pathways were described.


2010 ◽  
Vol 5 (9) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Yoshiaki Noma ◽  
Yoshinori Asakawa

The biotransformation of (-)-nopol benzyl ether (5) by Aspergillus Niger TBUYN-2 and A. niger Tiegh CBSYN was investigated. A. niger biotransformed 5 to afford (-)-4-oxonopol-2’,4’-dihydroxybenzyl ether (6), and (-)-4-oxonopol (7) as main products. Compound 6 showed strong antioxidant activity (IC50 30.2 μM), which was very similar to that of butyl hydroxyl anisol (BHA).


1958 ◽  
Vol 11 (3) ◽  
pp. 302 ◽  
Author(s):  
J Miller ◽  
AJ Parker

The substituent effects in aromatic nucleophilic substitution of groups attached to the benzene ring by a multiple-bond nitrogen atom are considered. Attachment is para to a replaceable halogen atom, and generally as a 4-substituent to l-chloro-2-nitrobenzene. Comparisons with some other groups are shown. Reasons are given for the greater T effect of a triple than of a double bond. Hammett substituent constants (σ*) are computed. Those for the nitroso and diazonium groups .are the largest so far obtained for electrically neutral and cationic groups respectively. The activating power of four of the nitrogen groups in electrophilic as well as nucleophilic substitution is discussed briefly.


2014 ◽  
Vol 70 (9) ◽  
pp. o936-o937
Author(s):  
Dongsoo Koh

In the structure of the title compound, C12H12O3, the dihydropyran ring is fused with the benzene ring. The dihydropyran ring is in a half-chair conformation, with the ring O and methylene C atoms positioned 1.367 (3) and 1.504 (4) Å, respectively, on either side of the mean plane formed by the other four atoms. The methoxy group is coplanar with the benzene ring to which it is connected [Cb—Cb—Om—Cmtorsion angle = −0.2 (4)°; b = benzene and m = methoxy], and similarly the aldehyde is coplanar with respect to the double bond of the dihydropyran ring [Cdh—Cdh—Ca—Oa= −178.1 (3)°; dh = dihydropyran and a = aldehyde]. In the crystal, molecules are linked by weak methyl–methoxy C—H...O hydrogen bonds into supramolecular chains along thea-axis direction.


2014 ◽  
Vol 70 (9) ◽  
pp. o1051-o1052 ◽  
Author(s):  
Ignez Caracelli ◽  
Stella H. Maganhi ◽  
Paulo J. S. Moran ◽  
Bruno R. S. de Paula ◽  
Felix N. Delling ◽  
...  

In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] isE, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in theorthoposition is twisted [O—N—C—C = 138.28 (13)°]. The molecules associateviaC—H...O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N...O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].


2012 ◽  
Vol 2012 ◽  
pp. 1-7 ◽  
Author(s):  
Ayssar Nahlé ◽  
Ideisan I. Abu-Abdoun ◽  
Ibrahim Abdel-Rahman

The inhibition and the effect of temperature and concentration of trans-4-hydroxy-4′-stilbazole on the corrosion of mild steel in 1 M HCl solution was investigated by weight loss experiments at temperatures ranging from 303 to 343 K. The studied inhibitor concentrations were between  M and  M. The percentage inhibition increased with the increase of the concentration of the inhibitor. The percentage inhibition reached about 94% at the concentration of  M and 303 K. On the other hand, the percentage inhibition decreased with the increase of temperature. Using the Temkin adsorption isotherm, the thermodynamic parameters for the adsorption of this inhibitor on the metal surface were calculated. Trans-4-hydroxy-4′-stilbazole was found to be a potential corrosion inhibitor since it contained not only nitrogen and oxygen, but also phenyl and pyridine rings that are joined together with a double bond (–C=C–) in conjugation with these rings.


1967 ◽  
Vol 45 (11) ◽  
pp. 2137-2153 ◽  
Author(s):  
A. Fuchs ◽  
R. Rohringer ◽  
D. J. Samborski

Wheat leaves infected with stem rust, especially those of susceptible plants, contained more phenylalanine and tyrosine than healthy leaves. The utilization of phenylalanine was increased in both the susceptible and resistant reaction, but the utilization of tyrosine was increased only in the susceptible reaction. No evidence of interconversion of these amino acids was obtained.In n-butanol extracts, which contained glycosides, many constituents were labelled after feeding of L-phenylalanine-U-14C. Most of the n-butanol extractives from resistant-reacting leaves contained more label than those from susceptible-reacting leaves or from healthy leaves. However, one of the n-butanol extractives from susceptible-reacting leaves was 5–10 times as active as that isolated from the other tissues.With L-phenylalanine-U-14C and ferulate-U-14C as precursors, more activity was recovered in insoluble than in soluble esters (of ferulate and p-coumarate). With L-tyrosine-U-14C as precursor, the reverse was observed. After infection, the proportion of label in insoluble esters increased more in resistant leaves than it did in susceptible leaves, regardless of the precursor used.A major portion of the activity from these precursors was recovered in the insoluble residue that contained protein and other polymers. In the experiment with L-phenylalanine-U-14C, this residue was fractionated into protein and non-hydrolyzable material. Susceptible-reacting leaves contained equal amounts of activity in these fractions, while resistant-reacting leaves incorporated 2.5 times as much activity into the non-hydrolyzable material as into protein.


2012 ◽  
Vol 610-613 ◽  
pp. 3574-3579
Author(s):  
Cui Hua Wang ◽  
Sheng Long Yang ◽  
Chao Lu ◽  
Hong Xia Yu ◽  
Lian Shen Wang ◽  
...  

By using CoMFA and CoMSIA methods, the new quantitative structures of 25 aromatic hydrocarbons and the 96 hr-EC50 data with C. vulgaris have been investigated to obtain more detailed insight into the relationships between molecular structure and bioactivity. Compared to CoMFA (the average Q2LOO option =0.610), CoMSIA (the average Q2LOO =0.736) has the better results with robustness and stability. CoMSIA analysis using steric, electrostatic, hydrophobic, and H-bond donor and acceptor descriptors show H-bond donor is the common factor for influencing the toxicity, the steric and electrostatic descriptors are next and the hydrophobic descriptor was last. From the contour maps, the number of benzene ring is more crucial for the compound toxicity and the compounds with more benzene ring make toxicity increased. Under the same number of benzene ring, the kind of substituent group and the formed ability of H-bond are the other parameters to influencing the aromatic hydrocarbons toxicity.


1994 ◽  
Vol 14 (1) ◽  
pp. 501-508
Author(s):  
J J Bonner ◽  
C Ballou ◽  
D L Fackenthal

The heat shock transcription factor (HSF) is a trimer that binds to DNA containing inverted repeats of the sequence nGAAn. HSF can bind DNA with the sequence nGAAnnTTCn or with the sequence nTTCnnGAAn, with little preference for either sequence over the other. However, (nGAAnnTTCn)2 is considerably less active as a heat shock response element (HSE) than is (nTTCnnGAAn)2. The electrophoretic mobilities of DNA-protein complexes and chemical cross-linking between protein monomers indicate that the sequence (nGAAnnTTCn)2 is capable of binding a single HSF trimer. In contrast, the sequence with higher biological activity, (nTTCnnGAAn)2, is capable of binding two trimers. Thus, the ability of four-nGAAn-element HSEs to bind one or two trimers depends on the permutation with which the elements are presented. A survey of naturally occurring HSEs shows the sequence (nTTCnnGAAn)2 to be the more prevalent. We suggest that the greater ability of one permutation over the other to bind two HSF trimers accounts for the initial identification of the naturally occurring heat shock consensus sequence as a region of dyad symmetry.


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