Transformation of artemisinin by Cunninghamella elegans

doi:10.1007/S00253-003-1524-Z

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Transformation of artemisinin by Cunninghamella elegans

Journal Article•DOI•

Transformation of artemisinin by Cunninghamella elegans

Igor A. Parshikov¹, K. M. Muraleedharan¹, Mitchell A. Avery¹, John S. Williamson¹•Institutions (1)

University of Mississippi¹

21 Jan 2004-Applied Microbiology and Biotechnology (Springer-Verlag)-Vol. 64, Iss: 6, pp 782-786

TL;DR: 7β-hydroxyartemisinin, obtained from microbial transformation, is utilized as a semi-synthetic precursor for the synthesis of novel 7β-substituted art Artemisinin anti-malarial agents.

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Abstract: Semi-synthetic derivatives of the anti-malarial drug artemisinin hold great promise in the search for an effective and economical treatment of chloroquine-resistant forms of malaria. Unfortunately, synthetic functionalization of the artemisinin skeleton is often tedious and/or impractical. We seek to utilize 7β-hydroxyartemisinin, obtained from microbial transformation, as a semi-synthetic precursor for the synthesis of novel 7β-substituted artemisinin anti-malarial agents. Here we employ liquid cultures of Cunninghamella elegans as a means for the rational and economical bioconversion of artemisinin to 7β-hydroxyartemisinin in 78.6% yield. In addition, there were three other bioconversion products: 7β-hydroxy-9α-artemisinin (6.0%), 4α-hydroxy-1-deoxoartemisinin (5.4%), and 6β-hydroxyartemisinin (6.5%).

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Journal Article•DOI•

Cunninghamella--a microbial model for drug metabolism studies--a review.

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Sepuri Asha¹, M. Vidyavathi¹•Institutions (1)

Sri Padmavati Mahila Visvavidyalayam¹

01 Jan 2009-Biotechnology Advances

TL;DR: Emphasis is laid on the potential of Cunninghamella fungus to mimic mammalian drug biotransformations and to use as in vitro model for drug metabolism studies and for further toxicological and pharmacological studies of metabolites.

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196 citations

Cites background from "Transformation of artemisinin by Cu..."

...This species is used extensively as a microbial model for mammalian hepatic metabolism of aromatic xenobiotics (Parshikov et al., 2004; Shanmugam et al., 2003; Moody et al., 2002)....
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...4 α hydroxy-1-deoxo artemisinin; 6 β-hydroxy artemisinin Parshikov et al. (2004)...
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Journal Article•DOI•

Iron- and cobalt-catalyzed C(sp3)-H bond functionalization reactions and their application in organic synthesis.

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Yungen Liu¹, Tingjie You², Hai-Xu Wang², Zhou Tang², Cong-Ying Zhou², Chi-Ming Che¹, Chi-Ming Che² - Show less +3 more•Institutions (2)

Southern University of Science and Technology¹, University of Hong Kong²

03 Aug 2020-Chemical Society Reviews

TL;DR: Developments in iron- and cobalt-catalyzed C(sp3)-H bond functionalization reactions are described, with an emphasis on their applications in organic synthesis, i.e., the synthesis of natural products and pharmaceuticals and/or their modification.

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Abstract: Direct C-H bond functionalization catalyzed by non-precious transition metals is an attractive strategy in synthetic chemistry Compared with the precious metals rhodium, palladium, ruthenium, and iridium commonly used in this field, catalysis based on non-precious metals, especially the earth-abundant ones, is appealing due to the increasing demand for environmentally benign and sustainable chemical processes Herein, developments in iron- and cobalt-catalyzed C(sp3)-H bond functionalization reactions are described, with an emphasis on their applications in organic synthesis, ie, the synthesis of natural products and pharmaceuticals and/or their modification

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93 citations

Journal Article•DOI•

Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway: A review

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Mohamed-Elamir F. Hegazy, Tarik A. Mohamed, Abdelsamed I. Elshamy, Abou-El-Hamd H Mohamed¹, Usama A. Mahalel¹, Eman H. Reda, Alaa M. Shaheen, Wafaa A. Tawfik, Abdelaaty A. Shahat², Khalid A. Shams, Nahla S. Abdel-Azim, F. M. Hammouda - Show less +8 more•Institutions (2)

South Valley University¹, King Saud University²

01 Jan 2015-Journal of Advanced Research

TL;DR: In this paper, a review on the usage of microbial biocatalysts for some natural product classes and natural product drugs is presented, which is the first review published in the literature.

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91 citations

Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway: A review Production and hosting by Elsevier

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Mohamed Elamir F. Hegazy, Tarik A. Mohamed, Abdelsamed I. Elshamy, Abou El-Hamd H. Mohamed, Usama A. Mahalel, Eman H. Reda, Alaa M. Shaheen, Wafaa A. Tawfik, Abdelaaty A. Shahat, Khalid A. Shams, Nahla S. Abdel Azim, F. M. Hammouda - Show less +8 more

01 Jan 2015

TL;DR: Graphical abstracts as mentioned in this paper are used in this paper. But they do not specify the authorship of the abstracts, only the authors themselves, and their authorship is unknown.

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Abstract: Graphical abstract

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87 citations

Journal Article•DOI•

Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae

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Hui Wang¹, Lihong Liu¹, Yong-Xue Guo¹, Yuesheng Dong¹, Dai-Jia Zhang¹, Zhilong Xiu¹ - Show less +2 more•Institutions (1)

Dalian University of Technology¹

28 Feb 2007-Applied Microbiology and Biotechnology

TL;DR: Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae was investigated and it was found that biotransformation is a better method to increase the yield of resver atrol because of its high yield and mild conditions.

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Abstract: Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae was investigated in this study. Resveratrol is widely used in medicine, food, and cosmetic because of its pharmacological properties. However, it has a much lower content in plants compared with its glucoside piceid, which has a much lower bioavailability. Traditionally, the aglycone is acquired by acid or enzymatic hydrolysis of its glucoside, but the violent condition and the acid pollution in hydrolytic reaction and the high cost of the enzyme limit their industrial development. In this paper, fermentation of P. cuspidatum by A. oryzae was successfully performed, during which, piceid was converted to resveratrol with the highest yield of trans-resveratrol 1.35%, 3.6 times higher than that obtained from raw herb by microwave-assisted extraction. Scale-up production was also performed and the yield of trans-resveratrol was 3.1 times higher after 24 h incubation. Therefore, biotransformation is a better method to increase the yield of resveratrol because of its high yield and mild conditions.

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83 citations

Cites methods from "Transformation of artemisinin by Cu..."

...Hydroxylation of 10- deoxoartemisinin was performed by Aspergillus niger (Parshikov et al. 2004a,b)....
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Journal Article•DOI•

Metabolism of antimalarial sesquiterpene lactones.

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Ik-Soo Lee¹, Charles D. Hufford¹•Institutions (1)

University of Mississippi¹

01 Jan 1990-Pharmacology & Therapeutics

TL;DR: Microbial models served as effective predictors for the mammalian metabolism of artemisinin derivatives as well as producing quantities of metabolites for reference standards and structure elucidation studies.

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133 citations

"Transformation of artemisinin by Cu..." refers background in this paper

...Biotransformation of artemisinin and its derivatives has been described in humans, animals, and microorganisms, and usually include the metabolic processes: hydroxylation of methyl, methyne and methylene groups; deoxidation reactions; hydration reactions; and breakdown of heterocyclic rings (Abourashed et al. 1999; Grogan and Holland 2000; Hufford et al. 1990; Lee and Hufford 1990; Zhan at al. 2002a, 2002b; Ziffer et al. 1992)....
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...…many synthetic manipulations impossible and/or impracticable, yet there are reports indicating that the sequiterpene is susceptible to bioconversion by a variety of microorganisms (Fiaux de Medeiros et al. 2002; Lee and Hufford 1990; Lee et al. 1989; Zhan et al. 2002a, 2002b; Ziffer et al. 1992)....
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...The complexity of the artemisinin molecule renders many synthetic manipulations impossible and/or impracticable, yet there are reports indicating that the sequiterpene is susceptible to bioconversion by a variety of microorganisms (Fiaux de Medeiros et al. 2002; Lee and Hufford 1990; Lee et al. 1989; Zhan et al. 2002a, 2002b; Ziffer et al. 1992)....
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...…and usually include the metabolic processes: hydroxylation of methyl, methyne and methylene groups; deoxidation reactions; hydration reactions; and breakdown of heterocyclic rings (Abourashed et al. 1999; Grogan and Holland 2000; Hufford et al. 1990; Lee and Hufford 1990; Zhan at al....
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Journal Article•

Microbial models of mammalian metabolism of xenobiotics: An updated review.

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Ehab A. Abourashed¹, A. M. Clark, C. D. Hufford•Institutions (1)

University of Mississippi¹

01 May 1999-Current Medicinal Chemistry

TL;DR: The results of studies that were conducted over the last seven years are outlined to emphasize the similarities between the microbial and mammalian metabolic pathways of xenobiotics through the endorsement of the concept of microbial models of mammalian metabolism.

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Abstract: The utilization of microbes as models for mammalian metabolism of xenobiotics has been well established since the concept was first introduced by Smith and Rosazza in the early seventies. The core assumption of this concept rests on the fact that fungi are eukaryotic organisms that possess metabolizing enzyme systems similar to those present in mammalian systems. Hence, the outcome of xenobiotic metabolism in both systems is expected to be similar, if not identical, and, thus, fungi can be used to predict the outcome of mammalian metabolism of various xenobiotics, including drugs. Utilizing microbial models offers a number of advantages over the use of animals in metabolism studies, mainly reduction in use of animals, ease of setup and manipulation, higher yield and diversity of metabolite production, and lower cost of production. In a continuation to our contribution to this field, this review will outline the results of studies that were conducted over the last seven years to emphasize the similarities between the microbial and mammalian metabolic pathways of xenobiotics through the endorsement of the concept of microbial models of mammalian metabolism .

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98 citations

"Transformation of artemisinin by Cu..." refers background in this paper

...Biotransformation of artemisinin and its derivatives has been described in humans, animals, and microorganisms, and usually include the metabolic processes: hydroxylation of methyl, methyne and methylene groups; deoxidation reactions; hydration reactions; and breakdown of heterocyclic rings (Abourashed et al. 1999; Grogan and Holland 2000; Hufford et al. 1990; Lee and Hufford 1990; Zhan at al. 2002a, 2002b; Ziffer et al. 1992)....
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...…and usually include the metabolic processes: hydroxylation of methyl, methyne and methylene groups; deoxidation reactions; hydration reactions; and breakdown of heterocyclic rings (Abourashed et al. 1999; Grogan and Holland 2000; Hufford et al. 1990; Lee and Hufford 1990; Zhan at al....
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Book Chapter•DOI•

Microbial models for drug metabolism.

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R. Azerad¹•Institutions (1)

Paris Descartes University¹

01 Jan 1999-Advances in Biochemical Engineering \/ Biotechnology

TL;DR: Emphasis is laid on the potential for selected microorganisms to mimic all patterns of mammalian biotransformations and to provide preparative methods for structural identification and toxicological and pharmacological studies of drug metabolites.

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Abstract: This review describes microbial transformation studies of drugs, comparing them with the corresponding metabolism in animal systems, and providing technical methods for developing microbial models. Emphasis is laid on the potential for selected microorganisms to mimic all patterns of mammalian biotransformations and to provide preparative methods for structural identification and toxicological and pharmacological studies of drug metabolites.

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91 citations

"Transformation of artemisinin by Cu..." refers background in this paper

...Fungi from the genus Cunninghamella are well known for their ability to transform a variety of organic compounds (Azerad 1999; Parshikov et al. 1994; Sutherland et al. 1994)....
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Journal Article•DOI•

Orally active, hydrolytically stable, semisynthetic, antimalarial trioxanes in the artemisinin family

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Gary H. Posner¹, Michael H. Parker¹, John Northrop¹, Jeffrey S. Elias¹, Poonsakdi Ploypradith¹, Suji Xie¹, Theresa A. Shapiro¹ - Show less +3 more•Institutions (1)

Johns Hopkins University¹

28 Jan 1999-Journal of Medicinal Chemistry

TL;DR: All of these C-10 nonacetal, chemically robust, enantiomerically pure compounds 4-9 have high antimalarial potencies in vitro against Plasmodium falciparum malaria parasites, and furans 5a and 5b and pyrrole 7a are antimalarially potent also in vivo even when administered to rodents orally.

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Abstract: In only three chemical operations, natural trioxane lactone artemisinin (1) was converted into a series of C-10 carbon-substituted 10-deoxoartemisinin compounds 4-9. The three steps involved lactone reduction, replacement of the anomeric lactol OH by F using diethylaminosulfur trifluoride, and finally boron trifluoride-promoted substitution of F by aryl, heteroaryl, and acetylide nucleophiles. All of these C-10 nonacetal, chemically robust, enantiomerically pure compounds 4-9 have high antimalarial potencies in vitro against Plasmodium falciparum malaria parasites, and furans 5a and 5b and pyrrole 7a are antimalarially potent also in vivo even when administered to rodents orally.

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81 citations

"Transformation of artemisinin by Cu..." refers background in this paper

...Quantitative structural activity relationship (QSAR) studies of its skeleton (Avery et al. 1999; Posner et al.1999) suggest that structural manipulation of the sesquiterpene lactone may yield more desirable anti-malarial analogs....
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Journal Article•DOI•

C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene.

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Sanchai Ekthawatchai¹, Sumalee Kamchonwongpaisan², Palangpon Kongsaeree², Bongkoch Tarnchompoo², Yodhathai Thebtaranonth², Yongyuth Yuthavong² - Show less +2 more•Institutions (2)

Mahidol University¹, Thailand National Science and Technology Development Agency²

22 Nov 2001-Journal of Medicinal Chemistry

TL;DR: Nucleophilic additions of lithium keto and ester enolates and mono- and bifunctional Grignard reagents to artemisitene provided C-16-derived artemisinin monomers, dimers, trimers, and tetramers whose antimalarial and cytotoxic activities have been evaluated.

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Abstract: Nucleophilic additions of lithium keto and ester enolates and mono- and bifunctional Grignard reagents to artemisitene provided C-16-derived artemisinin monomers, dimers, trimers, and tetramers whose antimalarial and cytotoxic activities have been evaluated.

...read moreread less

74 citations

"Transformation of artemisinin by Cu..." refers background in this paper

...Introduction Each year, it is estimated that almost 2 million people die from malaria, most of these victims being African children (Hu et al. 1992; Ekthawatchai et al. 2001)....
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