Biotransformation of Artemisinin to 14-Hydroxydeoxyartemisinin: C-14 Hydroxylation by <i>Aspergillus flavus</i>

Ponnapalli, Mangala Gowri; Sura, Madhu Babu; Sudhakar, Renu; Govindarajalu, Gokulapriya; Sijwali, Puran Singh

doi:10.1021/acs.jafc.8b03573

Cited by 13 publications

(12 citation statements)

References 29 publications

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“…The ability of this species to produce more than one type of degradative enzyme in high quantities may increase its potential to degrade PAH compounds (Barnes et al, 2018; Mohsenzadeh et al, 2012). These results are consistent with those of other studies in which fungi especially the genus Aspergillus has a great degradation ability for hydrocarbons (Al‐Hawash et al, 2018; Ponnapalli et al, 2018; Ye et al, 2011).…”

Section: Resultssupporting

confidence: 93%

“…The two species with the highest potential among the fungal isolates, A. flavus and A. fumigatus , were selected to test their ability to degrade PAHs as single isolates. These two fungi belong to the genus Aspergillus ; many species of this genus have been previously isolated and have demonstrated their ability as oil degraders (Al‐Hawash et al, 2018; Al‐Nasrawi, 2012; Mittal & Singh, 2008; Ponnapalli, Sura, Sudhakar, Govindarajalu, & Sijwali, 2018). In the present study, a significant amount of total PAHs was degraded after 15 days of incubation compared with the control treatment.…”

Section: Resultsmentioning

confidence: 99%

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Factors affecting polycyclic aromatic hydrocarbon biodegradation by Aspergillus flavus

Al‐Dossary

Abood

Al‐Saad

2020

Remediation Journal

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This study investigated the ability of fungi isolated from highly contaminated soil to biodegrade polycyclic aromatic hydrocarbon (PAH) compounds, as well as the effect of several parameters on the biodegradation ability of these fungi. The isolated fungi were identified using ITS rDNA sequencing and tested using 2,6‐dichlorophinolendophenol to determine their preliminary ability to degrade crude oil. The top‐performing fungi, Aspergillus flavus and Aspergillus fumigatus, were selected to test their ability to biodegrade PAH compounds as single isolates. After 15 days of incubation, A. flavus degraded 82.7% of the total PAH compounds, with the complete degradation of six compounds, whereas A. fumigatus degraded 68.9% of the total PAHs, with four aromatic compounds completely degraded. We also tested whether different temperatures, pH, and nitrogen sources influenced the growth of A. flavus and the degradation rate. The degradation process was optimal at a temperature of 30°C, pH of 5.5, and with nitrogen in the form of yeast extract. Finally, the ability of the fungal candidate, A. flavus, to degrade PAH compounds under these optimum conditions was studied. The results showed that 95.87% of the total PAHs, including 11 aromatic compounds, were completely degraded after 15 days of incubation. This suggests that A. flavus is a potential microorganism for the degradation of PAH compounds in aqueous cultures.

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Section: Resultssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Factors affecting polycyclic aromatic hydrocarbon biodegradation by Aspergillus flavus

Al‐Dossary

Abood

Al‐Saad

2020

Remediation Journal

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“…The biotransformation studies of 2 by Alternaria longipes AS 3.2875 have led to the isolation of six products of hydroxylation or glycosylation. Their structures were identified as 3-carbonyl-ursolic acid-28-O-β-D-glucopyranosyl ester (8), ursolic acid-3-O-β-D-glucopyranoside (9), ursolic acid-28-O-β-D-glucopyranosyl ester (10), 2α,3β-dihydroxy-ursolic acid-28-O-β-D-glucopyranosyl ester (11), 3β,21β-dihydroxyursolic acid-28-O-β-D-glucopyranosyl ester (12), and 3-O-(β-D-glucopyranosyl)ursolic acid-28-O-(β-D-glucopyranosyl) ester (13). Glycosylation reaction on pentacyclic triterpenoid fulfilled with difficulty in the process of chemical synthesis is facile by microbial transformation [20].…”

Section: Triterpenementioning

confidence: 99%

Microorganisms as Biocatalysts and Enzyme Sources

Cano-Flores¹,

Gómez²,

Escalona-Torres³

et al. 2020

Microorganisms

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Microbial-catalyzed biotransformations have considerable potential for the generation of an enormous variety of structurally diversified organic compounds, especially natural products with complex structures like triterpenoids, flavonoids, steroids, steroidal saponins, and sesquiterpenoids. They offer efficient and economical ways to produce semisynthetic analogues and novel lead molecules. Microorganisms such as bacteria and fungi could catalyze chemo-, regio-, and stereospecific hydroxylations of diverse substrates that are extremely difficult to produce by chemical routes. During recent years, considerable research has been performed on the microbial transformation of bioactive compounds, in order to obtain biologically active molecules with diverse structural features. In green chemistry, biotransformations are an important chemical methodology toward more sustainable industrial processes.

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“…Recently, a study on effective in vitro artemisinin-based treatments against SARS-CoV-2 has been reported . Therefore, the structural research of artemisinin intermediates has always remained of topmost interest to chemists and pharmacists . Diesterified polycyclic products keeping similar backbone structures to artemisinin intermediates has been paid a lot of attention in the field of synthetic organic chemistry as well.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Altenuene Backbones through Iodine(III)-Participated Umpolung Diesterification and Insights into the General [1,5]-H Shift in para-Dearomatization of Phenols via Quantum Chemical Calculations

Luo

Gao

et al. 2022

J. Org. Chem.

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Through PhI(OAc)2-oxidized dearomatization and diesterification of 3′-hydroxy-[1,1′-biphenyl]-2-carboxylic acids, a series of polycyclic compounds possessing an altenuene backbone were obtained in moderate to good yields. The Umpolung diesterification reaction was completed under mild reaction conditions without an additional nucleophilic reagent. This work offers a concise method for the synthesis of diverse natural altenuene analogues. The mechanism was proposed, and the [1,5]-H shift was studied in isomerization from the ketone-form structure to a phenol employing computational studies.

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Biotransformation of Artemisinin to 14-Hydroxydeoxyartemisinin: C-14 Hydroxylation by Aspergillus flavus

Cited by 13 publications

References 29 publications

Factors affecting polycyclic aromatic hydrocarbon biodegradation by Aspergillus flavus

Factors affecting polycyclic aromatic hydrocarbon biodegradation by Aspergillus flavus

Microorganisms as Biocatalysts and Enzyme Sources

Synthesis of Altenuene Backbones through Iodine(III)-Participated Umpolung Diesterification and Insights into the General [1,5]-H Shift in para-Dearomatization of Phenols via Quantum Chemical Calculations

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