Microbial Transformation of Tetracyclic Diterpenes: Conversion of Ent-Kaurenones by Aspergillus niger

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


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).


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.


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

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.


2013 ◽  
Vol 8 (2) ◽  
pp. 1934578X1300800
Author(s):  
Chen Li-Xia ◽  
Zhang Hui ◽  
Zhao Qian ◽  
Yin Shi-Yu ◽  
Zhang Zhong ◽  
...  

Curcumol is a representative index component for the quality control of the essential oil of Curcuma wenyujin Y.H. Chen et C. Ling, an antivirus and anticancer drug in China. Microbial transformation of curcumol (1) by Aspergillus niger AS 3.739 yielded two products. Their structures were elucidated as 3α-hydroxycurcumol (2) and 3α-(4′-methoxy-succinyloxy)-curcumol (3) by extensive spectroscopic methods including 2D-NMR and HRESI-MS. Among them, 3 is a new compound. Esterification of the substrate with succinic acid is a novel reaction in the field of microbial transformation of natural products. Compound 2, the major transformation product of 1, was a high regio- and stereo-specific hydroxylation product and showed significant antiviral effects.


1981 ◽  
Vol 45 (3) ◽  
pp. 791-793 ◽  
Author(s):  
Yoichi MIKAMI ◽  
Yumiko FUKUNAGA ◽  
Masatoshi ARITA ◽  
Yukiteru OBI ◽  
Takuro KISAKI

2014 ◽  
Vol 50 (4) ◽  
pp. 903-909
Author(s):  
Saeed Ahmad ◽  
Farhan Hameed Khaliq ◽  
Asadullah Madni ◽  
Muhammad Nabeel Shahid ◽  
Irfan Pervaiz

In the present research, the steroidal anti-asthmatic drug beclomethasone dipropionate was subjected to microbial biotransformation by Aspergillus niger. Beclomethasone dipropionate was transformed into various metabolites first time from microbial transformation. New drug metabolites produced can act as new potential drug molecules and can replace the old drugs in terms of safety, efficacy, and least resistance. They were purified by preparative thin layer chromatography technique, and their structures were elucidated using modern spectroscopic techniques, such as 13C NMR, 1H NMR, HMQC, HMQC, COSY, and NOESY, and mass spectrometry, such as EI-MS. Four metabolites were purified: (i) beclomethasone 17-monopropionate, (ii) beclomethasone 21-monopropionate, (iii) beclomethasone, and (iv) 9beta,11beta-epoxy-17,21-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 21-propionate.


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