Extractives of fungi. V. Microbial transformation products of piperitone

1973 ◽  
Vol 26 (4) ◽  
pp. 845 ◽  
Author(s):  
EV Lassak ◽  
JT Pinhey ◽  
BJ Ralph ◽  
T Sheldon ◽  
JJH Simes
Keyword(s):  
Aspergillus Niger ◽  
Microbial Transformation ◽  
Transformation Products ◽  
Transformation Product ◽  
Major Transformation ◽  
A Minor

The products obtained from the transformation of (�)-piperitone (1) by Pro-actinomyces roseus, a species of Fusarium, and Aspergillus niger have been examined. Major transformation products include (�)-trans-6- hydroxy-p-menth-1-en-3-one (2) and (�)-7-hydroxy-p-menth-1-en-3-one (3); a minor transformation product has been tentatively identified as (�)-8-hydroxy-p-menth-1-en-3-one (4).

scholarly journals Microbial Transformation of Curcumol by Aspergillus niger

2013 ◽  
Vol 8 (2) ◽  
pp. 1934578X1300800
Author(s):  
Chen Li-Xia ◽  
Zhang Hui ◽  
Zhao Qian ◽  
Yin Shi-Yu ◽  
Zhang Zhong ◽  
...  
Keyword(s):  
Quality Control ◽  
Natural Products ◽  
Aspergillus Niger ◽  
Essential Oil ◽  
Microbial Transformation ◽  
2D Nmr ◽  
Transformation Product ◽  
Spectroscopic Methods ◽  
Antiviral Effects ◽  
Major Transformation

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.

scholarly journals A Novel Microbial Zearalenone Transformation through Phosphorylation

Toxins ◽  
2021 ◽  
Vol 13 (5) ◽  
pp. 294
Author(s):  
Yan Zhu ◽  
Pascal Drouin ◽  
Dion Lepp ◽  
Xiu-Zhen Li ◽  
Honghui Zhu ◽  
...  
Keyword(s):  
Microbial Transformation ◽  
Acid Tolerance ◽  
Transformation Product ◽  
The United States ◽  
Corn Silage ◽  
Rrna Gene ◽  
Bacillus Spp ◽  
High Concentrations ◽  
The 16S Rrna Gene ◽  
Bacillus Strains

Zearalenone (ZEA) is a mycotoxin widely occurring in many agricultural commodities. In this study, a purified bacterial isolate, Bacillus sp. S62-W, obtained from one of 104 corn silage samples from various silos located in the United States, exhibited activity to transform the mycotoxin ZEA. A novel microbial transformation product, ZEA-14-phosphate, was detected, purified, and identified by HPLC, LC-MS, and NMR analyses. The isolate has been identified as belonging to the genus Bacillus according to phylogenetic analysis of the 16S rRNA gene and whole genome alignments. The isolate showed high efficacy in transforming ZEA to ZEA-14-phosphate (100% transformation within 24 h) and possessed advantages of acid tolerance (work at pH = 4.0), working under a broad range of temperatures (22–42 °C), and a capability of transforming ZEA at high concentrations (up to 200 µg/mL). In addition, 23 Bacillus strains of various species were tested for their ZEA phosphorylation activity. Thirteen of the Bacillus strains showed phosphorylation functionality at an efficacy of between 20.3% and 99.4% after 24 h incubation, suggesting the metabolism pathway is widely conserved in Bacillus spp. This study established a new transformation system for potential application of controlling ZEA although the metabolism and toxicity of ZEA-14-phosphate requires further investigation.

scholarly journals 3.ALPHA.-Hydroxy-ML-236B(3.ALPHA.-hydroxycompactin), microbial transformation product of ML-236B (compactin)

1983 ◽  
Vol 36 (5) ◽  
pp. 608-610 ◽  
Author(s):  
NOBUFUSAS ERIZAWA ◽  
KEIKO NAKAGAWA ◽  
YOSHIO TSUJITA ◽  
AKIRA TERAHARA ◽  
HARUMITSUK UWANO
Keyword(s):  
Microbial Transformation ◽  
Transformation Product

scholarly journals Microbial Transformation of Some Steroids by Cladosporium Cladosporioides Mrc 70282

2018 ◽  
Vol 42 (8) ◽  
pp. 408-411 ◽  
Author(s):  
Kudret Yildirim ◽  
Ali Kuru ◽  
Raşit Fikret Yılmaz
Keyword(s):  
Microbial Transformation ◽  
Cladosporium Cladosporioides ◽  
A Minor

Incubation of testosterone, androstenedione and progesterone with Cladosporium cladosporioides MRC 70282 for 5 days is reported. Testosterone was hydroxylated at C-16β and then oxidised at C-16. This was accompanied by a minor independent oxidation at C-17 and epimerisation at C-17. Androstenedione was reduced at C-17 and hydroxylated at C-16β, and this was then oxidised to a ketone at C-16. This was accompanied by a minor epimerisation at C-17. Progesterone was hydroxylated at C-21, and this was accompanied by a minor independent 5α-reduction.

A Photochemical Study of Diclofenac and Its Major Transformation Products

2010 ◽  
Vol 86 (3) ◽  
pp. 528-532 ◽  
Author(s):  
Johan Eriksson ◽  
Jesper Svanfelt ◽  
Leif Kronberg
Keyword(s):  
Transformation Products ◽  
Major Transformation

Microbial Transformation of Isosteviol Lactone and Evaluation of the Transformation Products on Androgen Response Element

2008 ◽  
Vol 71 (4) ◽  
pp. 602-607 ◽  
Author(s):  
Bo-Hon Chou ◽  
Li-Ming Yang ◽  
Shwu-Fen Chang ◽  
Feng-Lin Hsu ◽  
Chia-Hsin Lo ◽  
...  
Keyword(s):  
Microbial Transformation ◽  
Transformation Products ◽  
Response Element ◽  
Androgen Response Element

Biotransformation of Glabratephrin, a Rare Type of Isoprenylated Flavonoids, by Aspergillus niger

2008 ◽  
Vol 63 (7-8) ◽  
pp. 561-564 ◽  
Author(s):  
Abou-El-Hamd H Mohamed ◽  
Ali K. Khalafallah ◽  
Afifi H. Yousof
Keyword(s):  
Aspergillus Niger ◽  
Ring Opening ◽  
Microbial Transformation ◽  
Membered Ring ◽  
Nmr Studies ◽  
Rare Type ◽  
Tephrosia Purpurea ◽  
Isolated Compound

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.

High-Throughput Identification of Microbial Transformation Products of Organic Micropollutants

2010 ◽  
Vol 44 (17) ◽  
pp. 6621-6627 ◽  
Author(s):  
Damian E. Helbling ◽  
Juliane Hollender ◽  
Hans-Peter E. Kohler ◽  
Heinz Singer ◽  
Kathrin Fenner
Keyword(s):  
High Throughput ◽  
Microbial Transformation ◽  
Transformation Products ◽  
Organic Micropollutants

scholarly journals Photocatalytic Degradation of Diclofenac by Hydroxyapatite–TiO2 Composite Material: Identification of Transformation Products and Assessment of Toxicity

Materials ◽  
2018 ◽  
Vol 11 (9) ◽  
pp. 1779 ◽  
Author(s):  
Sapia Murgolo ◽  
Irina Moreira ◽  
Clara Piccirillo ◽  
Paula Castro ◽  
Gianrocco Ventrella ◽  
...  
Keyword(s):  
Chemical Structure ◽  
Wastewater Treatment Plants ◽  
Transformation Products ◽  
Environmental Water ◽  
Transformation Product ◽  
Target Compound ◽  
Germination Inhibition ◽  
Potential Applicability ◽  
Environmental Water Matrices

Diclofenac (DCF) is one of the most detected pharmaceuticals in environmental water matrices and is known to be recalcitrant to conventional wastewater treatment plants. In this study, degradation of DCF was performed in water by photolysis and photocatalysis using a new synthetized photocatalyst based on hydroxyapatite and TiO2 (HApTi). A degradation of 95% of the target compound was achieved in 24 h by a photocatalytic treatment employing the HApTi catalyst in comparison to only 60% removal by the photolytic process. The investigation of photo-transformation products was performed by means of UPLC-QTOF/MS/MS, and for 14 detected compounds in samples collected during treatment with HApTi, the chemical structure was proposed. The determination of transformation product (TP) toxicity was performed by using different assays: Daphnia magna acute toxicity test, Toxi-ChromoTest, and Lactuca sativa and Solanum lycopersicum germination inhibition test. Overall, the toxicity of the samples obtained from the photocatalytic experiment with HApTi decreased at the end of the treatment, showing the potential applicability of the catalyst for the removal of diclofenac and the detoxification of water matrices.

Microbial Transformations of Azaarenes in Creosote-Contaminated Soil and Ground Water: Laboratory and Field Studies

1988 ◽  
Vol 20 (11-12) ◽  
pp. 17-23 ◽  
Author(s):  
Wilfred E. Pereira ◽  
Colleen E. Rostad ◽  
David M. Updegraff ◽  
Jon L. Bennett
Keyword(s):  
Ground Water ◽  
Contaminated Soil ◽  
Isotope Labeling ◽  
Microbial Transformation ◽  
Wood Preservative ◽  
Transformation Products ◽  
Gas Chromatography Mass Spectrometry ◽  
Experimental Conditions ◽  
Hydroxylation Reaction ◽  
Contaminated Aquifers

Azaarenes or aromatic nitrogen heterocycles are a class of compounds found in wood-preservative wastes containing creosote. The fate and movement of these compounds in contaminated aquifers is not well understood. Water-quality studies in an aquifer contaminated with creosote near Pensacola, Florida, indicated that ground water was contaminated with several azaarenes and their oxygenated and alkylated derivatives, suggesting that these oxygenated compounds may be products of microbial transformation reactions. Accordingly, laboratory studies were designed to investigate the fate of these compounds. Under aerobic conditions, soil pseudomonads isolated from creosote-contaminated soil converted quinoline to 2(lH)quinolinone that subsequently was degraded to unknown products. A methanogenic consortium isolated from an anaerobic sewage digestor, in presence of ground-water and creosote-contaminated soil, converted quinoline, isoquinoline, and 4-methylquinoline to their respective oxygenated analogs. In addition, N-, C-, and O-methylated analogs of oxygenated azaarenes were identified by gas chromatography-mass spectrometry (GC-MS) in anaerobic cultures. Under the experimental conditions, 2-methylquinoline was biorefractory. Presence of similar biotransformation products in anaerobic cultures and contaminated ground water from the Pensacola site provided further evidence that these compounds indeed were microbial transformation products. Stable isotope labeling studies indicated that the source of the oxygen atom for this hydroxylation reaction under aerobic and anaerobic conditions was water. A mechanism was proposed for this hydroxylation reaction. Whereas parent azaarenes are biodegradable in both anaerobic and aerobic zones, oxygenated and alkylated analogs are more biorefractory and, hence, persistent in anaerobic zones of contaminated aquifers.

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