scholarly journals Microbial Transformation of (-)-Nopol Benzyl Ether: Direct Dihydroxylation of Benzene Ring

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).

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.


2008 ◽  
Vol 63 (7-8) ◽  
pp. 561-564 ◽  
Author(s):  
Abou-El-Hamd H Mohamed ◽  
Ali K. Khalafallah ◽  
Afifi H. Yousof

Microbial transformation of glabratephrin, the major isolated compound from Tephrosia purpurea, afforded pseudosemiglabrin. The formation of the transformed compound seems to be performed via ring opening-closure of a five-membered ring causing transformation from a spiro into a fused system. The structure of the transformed compound was determined by comprehensive NMR studies, including DEPT, COSY, HMQC, NOE and MS.


1986 ◽  
Vol 49 (1) ◽  
pp. 126-132 ◽  
Author(s):  
Andrés García-Granados ◽  
Antonio Martínez ◽  
M. Esther Onorato ◽  
Jose M. Arias

2014 ◽  
Vol 63 (1) ◽  
pp. 111-114 ◽  
Author(s):  
EDYTA KOSTRZEWA-SUSŁOW ◽  
MONIKA DYMARSKA ◽  
TOMASZ JANECZKO

Microbial transformation of 3-methoxyflavone into 3'-hydroxyflavon-3-yloxymethyl myristate was presented. Six filamentous fungi were used as biocatalysts: a wild strain of Aspergillus niger KB, its four UV mutants (A. niger MB, SBP, SBJ, 13/5) and the strain of Penicillium chermesinum 113. The highest yields were observed for the strains of A. niger KB and A. niger SBP (69.8% and 63.1%, respectively).


2011 ◽  
Vol 29 (No. 6) ◽  
pp. 610-615 ◽  
Author(s):  
A. Esmaeili ◽  
S. Rohany ◽  
S. Safaiyan ◽  
Z.S. Amir

Citronellol and hydroxy citronellal are fragrance ingredients used in decorative cosmetics and fine fragrances. They have many applications in flavourings, extracts, foods, and drugs manufacturing. Their use worldwide is in the range exceeding 1000 metric tons per annum. Previous studies investigated the biotransformation of citral by the free cell method and immobilised cell method with Saccharomyces cerevisae. In this research, the microbial transformation of citral by the sporulated surface cultures method with Aspergillus niger-PTCC 5011 was studied. In experiments, A. niger was inoculated on solid media in conical flasks. The transformation took place for the periods of time of 6 days and 15 days. The results were analysed by the theoretical study, Fourier transform infrared spectroscopy, gas chromatography, and gas chromatography-mass spectroscopy. The major compounds produced in 6 days were acetone (26.2%) and hydroxy citronellal (37.0%), while the major compounds after the 15-day period were acetone (15.0%) and citronellol (36.0%). As citronellol has numerous commercial applications, the 15-day biotransformation period was found to be preferable.


Toxicon ◽  
2020 ◽  
Vol 181 ◽  
pp. 57-68 ◽  
Author(s):  
Mosaad A. Abdel-Wahhab ◽  
Aziza A. El-Nekeety ◽  
Amal S. Hathout ◽  
Asmaa S. Salman ◽  
Sekena H. Abdel-Aziem ◽  
...  

2005 ◽  
Vol 33 (5) ◽  
pp. 349-352 ◽  
Author(s):  
Igor A. Parshikov ◽  
Brushapathy Miriyala ◽  
Kannoth M. Muraleedharan ◽  
Mitchell A. Avery ◽  
John S. Williamson

2020 ◽  
Vol 16 (4) ◽  
pp. 514-520
Author(s):  
Marwa A. Sh. Shehab ◽  
Mohamed El-Naggar ◽  
Rabab A. Ismail ◽  
Hala M. El Kafrawy ◽  
Amira Abood ◽  
...  

Background: Amongst the quinolone core structures, 8-hydroxyquinoline (8-HQ or quinolinol) stands out as the greatest frequently used therapeutic moietiy. This includes the most critical molecules in medicinal chemistry. Quinolinol remains a broad-spectrum ligand capable of chelating to a large number of metal ions. Methods: The synthesized quinolinols Mannich bases were screened for their in vitro antimicrobial activity against Staphylococcus aureus (ATTCC 6538), Escherichia coli (ATTCC 7839), Klebsiella pneumonia (ATCC10131). The antifungal activity of the prepared compounds was assessed against Candida albicans (10231), Aspergillus niger and Penicillium sp. The antioxidant activity of the established compounds was assessed by means of α, α-diphenyl-β-picrylhydrazyl (DPPH) free radical scavenging method. Results: The antimicrobial outcomes indicated that all the synthesized compounds excluding 5 and 9b displayed reasonable antibacterial activity against Staphylococcus aureus (ATTCC 6538) and Escherichia coli (ATTCC 7839) with an inhibition zones ranging from 13 to 23 mm. However, in the case of Klebsiella pneumonia (ATCC10131) only compound 6 did not show any activity. The results also indicated that compounds 2b and 3 were the most potent antibacterial compounds against the verified strains with minimum inhibitory concentration (MIC) values ranging from 0.05 to 0.5mg/ml. In the antifungal assay, all compounds showed good activity against Candida albicans (10231) except compounds 5 and 9b. However, in the case of Aspergillus niger and Penicillium sp. only compounds 2b and 3 showed good activity. In the antifungal assay, MIC values for compounds 2b and 3 ranged from 0.25 to 2.5 mg/ml against the specified fungal strains. The antioxidant activity was assessed using the DPPH scavenging activity method. The results indicated that 2b was the most active among all tested compounds, with almost double the antioxidant activity as compared with that of trolox (positive control). Conclusion: In this work, we describe the synthesis of new Mannich bases comprising 8-HQ (1) and its derivative (8). The resulted Mannich bases of type 2 were used in transamination reactions with hydrazine and hydrazine derivatives. The structures of the newly synthesized Mannich bases were confirmed based on the NMR spectroscopic data and elemental analysis. Antimicrobial and antioxidant activities were also assessed.


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