Microbial transformation of artemisinin by Aspergillus terreus

Yu, Hongchang; Zhu, Baowu; Zhan, Yulian

doi:10.1186/s40643-017-0164-6

Cited by 6 publications

(6 citation statements)

References 18 publications

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“…This is the first report of the production of 3 via mild biotransformation by a fungus. Compounds 4 and 5 were found in this study, in agreement with previous findings in the biotransformation of artemisinin by A. niger (Yu et al 2017;Zhan et al 2002bZhan et al , 2015. Compounds 4 and 5 were suggested to be formed simultaneously and independently as happened at a high temperature (Lin et al 1985) by reductive cleavage of the peroxide bridge of artemisinin (Fig.…”

Section: Discussionsupporting

confidence: 92%

“…Further biotransformation of artemisinin (1) by A. niger resulted in 5-β-hydroxyartemisinin and 7-β-hydroxyartemisinin (Parshikov et al 2006) similar as by E. amstelodami, and two novel compounds, 3-β-hydroxy-4,12-epoxy-1-deoxyartemisinin and 3,13-epoxyartemisinin together with known artemisinin G (7) and 3-α-hydroxydeoxyartemisinin by A. niger VKM F-1119 (Zhan et al 2015). A. terreus transformed artemisinin to deoxyartemisinin and 4-α-hydroxy-1-deoxyartemisinin (= 3-α-hydroxydeoxyartemisinin) (Yu et al 2017). The filamentous fungus A. flavus MTCC-9167 converted artemisinin to a new hydroxy derivative, 14-hydroxydeoxyartemisinin along with known deoxyartemisinin, artemisinin G (7) and 3-α-hydroxydeoxyartemisinin (Ponnapalli et al 2018).…”

Section: Discussionmentioning

confidence: 99%

“…Microbial transformation is also an efficient way to mimic the mammalian metabolism (Abourashed et al 1999). Previously, artemisinin (1) was transformed to various metabolites via deoxygenation (reduction) (Lee et al 1989;Yu et al 2017;Zhan et al 2002b), hydroxylation (Gaur et al 2014;Parshikov et al 2006Parshikov et al , 2004Zhan et al 2002a), oxidation (Liu et al 2006), C-acetoxylation (Goswami et al 2010), deoxygenation and hydroxylation (Lee et al 1989;Ponnapalli et al 2018), dihydroxylation (Zhan et al 2017) and epoxylation (Zhan et al 2015).…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of artemisinin to a novel derivative via ring rearrangement by Aspergillus niger

Luo

Mobley

Woodfine

et al. 2022

Appl Microbiol Biotechnol

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Artemisinin is a component part of current frontline medicines for the treatment of malaria. The aim of this study is to make analogues of artemisinin using microbial transformation and evaluate their in vitro antimalarial activity. A panel of microorganisms were screened for biotransformation of artemisinin (1). The biotransformation products were extracted, purified and isolated using silica gel column chromatography and semi-preparative HPLC. Spectroscopic methods including LC-HRMS, GC–MS, FT-IR, 1D and 2D NMR were used to elucidate the structure of the artemisinin metabolites.1H NMR spectroscopy was further used to study the time-course biotransformation. The antiplasmodial activity (IC50) of the biotransformation products of 1 against intraerythrocytic cultures of Plasmodium falciparum were determined using bioluminescence assays. A filamentous fungus Aspergillus niger CICC 2487 was found to possess the best efficiency to convert artemisinin (1) to a novel derivative, 4-methoxy-9,10-dimethyloctahydrofuro-(3,2-i)-isochromen-11(4H)-one (2) via ring rearrangement and further degradation, along with three known derivatives, compound (3), deoxyartemisinin (4) and 3-hydroxy-deoxyartemisinin (5). Kinetic study of the biotransformation of artemisinin indicated the formation of artemisinin G as a key intermediate which could be hydrolyzed and methylated to form the new compound 2. Our study shows that the anti-plasmodial potency of compounds 2, 3, 4 and 5 were ablated compared to 1, which attributed to the loss of the unique peroxide bridge in artemisinin (1). This is the first report of microbial degradation and ring rearrangement of artemisinin with subsequent hydrolysis and methoxylation by A.niger. Key points • Aspergillus niger CICC 2487 was found to be efficient for biotransformation of artemisinin • A novel and unusual artemisinin derivative was isolated and elucidated • The peroxide bridge in artemisinin is crucial for its high antimalarial potency • The pathway of biotransformation involves the formation of artemisinin G as a key intermediate

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Section: Discussionsupporting

confidence: 92%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Biotransformation of artemisinin to a novel derivative via ring rearrangement by Aspergillus niger

Luo

Mobley

Woodfine

et al. 2022

Appl Microbiol Biotechnol

View full text Add to dashboard Cite

show abstract

“…88 The fast decompression in SFE converts thermal energy into mechanical energy, which results in physical tearing and dissociation of the biomass. 89 The process basically can be divided into two phases of steam boiling and explosion. Steam boiling is similar to thermal pre-treatment and is a thermochemical reaction, however, the second phase is an adiabatic expansion reaction when the sudden physical expansion of the material occurs, [89][90][91] and the explosion power density (P) can be described in the hypothesis of the expansion process as follows:…”

Section: Oxidation Methodsmentioning

confidence: 99%

Keratin: dissolution, extraction and biomedical application

et al. 2017

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Keratinous materials such as wool, feathers and hooves are tough unique biological co-products that usually have high sulfur and protein contents. A high cystine content (7-13%) differentiates keratins from other structural proteins, such as collagen and elastin. Dissolution and extraction of keratin is a difficult process compared to other natural polymers, such as chitosan, starch, collagen, and a large-scale use of keratin depends on employing a relatively fast, cost-effective and time efficient extraction method. Keratin has some inherent ability to facilitate cell adhesion, proliferation, and regeneration of the tissue, therefore keratin biomaterials can provide a biocompatible matrix for regrowth and regeneration of the defective tissue. Additionally, due to its amino acid constituents, keratin can be tailored and finely tuned to meet the exact requirement of degradation, drug release or incorporation of different hydrophobic or hydrophilic tails. This review discusses the various methods available for the dissolution and extraction of keratin with emphasis on their advantages and limitations. The impacts of various methods and chemicals used on the structure and the properties of keratin are discussed with the aim of highlighting options available toward commercial keratin production. This review also reports the properties of various keratin-based biomaterials and critically examines how these materials are influenced by the keratin extraction procedure, discussing the features that make them effective as biomedical applications, as well as some of the mechanisms of action and physiological roles of keratin. Particular attention is given to the practical application of keratin biomaterials, namely addressing the advantages and limitations on the use of keratin films, 3D composite scaffolds and keratin hydrogels for tissue engineering, wound healing, hemostatic and controlled drug release.

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“…In recent years, Saccharomyces cerevisiae has served as an important platform organism for bio-based production of an ever-increasing list of biofuels, bulk chemicals, and pharmaceuticals in a sustainable and green way (Engels et al 2008;Kondo et al 2012;Li et al 2016;Marienhagen and Bott 2013). Until recently, various important molecular compounds, such as artemisinin precursor, farnesene, and ginsenosides, have been synthesized with high efficiency in S. cerevisiae facilitating the rapid evolution of the fields of metabolic engineering and synthetic biology (Dai et al 2014;Ro et al 2006;Meadows et al 2016;Yu et al 2017). The design-build-test strategy of synthetic biology involves the construction and optimization of cell factories, often requiring dramatic reconstruction and frequent debugging of metabolic networks of S. cerevisiae (Carbonell et al 2016;Nielsen and Keasling 2016;Paddon and Keasling 2014;Smanski et al 2014).…”

Section: Introductionmentioning

confidence: 99%

Self-cloning CRISPR/Cpf1 facilitated genome editing in Saccharomyces cerevisiae

Wang

Wei

2018

Bioresour. Bioprocess.

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Background: Saccharomyces cerevisiae is one of the most important industrial microorganisms. A robust genome editing tool is vital for both fundamental research and applications. To save the time and labor consumed in the procedure of genome editing, a self-cloning CRISPR/Cpf1 system (scCRISPR/Cpf1), in which a self-cleaving plasmid and PCR-generated site-specific crRNA fragment were included, was developed. Results: Using scCRISPR/Cpf1 as the genetic tool, simple and fast singleplex and multiplex genomic integration of in vivo assembled DNA parts were investigated. Moreover, we validate the applicability of scCRISPR/Cpf1 for cell factory development by creating a patchoulol production strain through two rounds of iterative genomic integration. The results showed that scCRISPR/Cpf1 enables singleplex and tripleplex genomic integration of in vivo assembled DNA parts with efficiencies of 80 and 32%, respectively. Furthermore, the patchoulol production strain was successfully and rapidly engineered and optimized through two rounds of iterative genomic integration by scCRISPR/Cpf1. Conclusions: scCRISPR/Cpf1 allows for CRISPR/Cpf1-facilitated genome editing by circumventing the step to clone a site-specific crRNA plasmid without compromising efficiency in S. cerevisiae. This method enriches the current set of tools available for strain engineering in S. cerevisiae.

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Microbial transformation of artemisinin by Aspergillus terreus

Cited by 6 publications

References 18 publications

Biotransformation of artemisinin to a novel derivative via ring rearrangement by Aspergillus niger

Biotransformation of artemisinin to a novel derivative via ring rearrangement by Aspergillus niger

Keratin: dissolution, extraction and biomedical application

Self-cloning CRISPR/Cpf1 facilitated genome editing in Saccharomyces cerevisiae

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