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The expression of Spodoptera exigua p450 and UGT genes: tissue specificity and response to insecticides

Insect Science 2019年第2期26卷 199-216页

作者： Bo Hu Shu-Heng Zhang Miao-Miao Ren Xiang-Rui Tian Qi Wei David Kibe Mburu Jian-Ya Su Key Laboratory of Integrated Management of Crop Diseases and pests (Ministry of Education) College of Plant Protection Nanjing Agricultural University Nanjing China

Cytochrome p450 and UDp-glucosyltransferase (UGT) as phase I and phase II metabolism enzymes, respectively, play vital roles in the breakdown of endobiotics and xenobiotics. Insects can in crease the expression of detoxificatio n enzymes to cope with the stress from xenobiotics including insecticides. However, the molecular mechanisms for insecticide detoxification in Spodoptera exigua remain elusive, and the genes conferring insecticide metabolisms in this species are less well reported. In this study, 68 p450 and 32 UGT genes were identified. phylogenetic analysis showed gene expansions in CYp3 and CYp4 clans of p450 genes and UGT33 family of this pest. p450 and UGT genes exhibited specific tissue expression patterns. Insecticide treatments in fat body cells of S. exigua revealed that the expression levels of p450 and UGT genes were significantly influenced by challenges of abamectin, lambda-cyhalothrin, chlorantraniliprole, metaflumizone and indoxacarb. Multiple genes for detoxification were affected in expression levels after insecticide exposures. The results demonstrated that lambda-cyhalothrin, chlorantraniliprole, metaflumizone and indoxacarb induced similar responses in the expression of p450 and UGT genes in fat body cells;eight p450 genes and four UGT genes were co-up-regulated significantly, and no or only a few CYp/UGT genes were down-regulated significantly by these four insecticides. However, abamectin triggered a distinct response for p450 and UGT gene expression;more p450 and UGT genes were down-regulated by abamectin than by the other four compounds. In con elusion, p450 and UGT genes from S. exigua were identified, and different responses to abamectin suggest a different mechanism for insecticide detoxification.

关键词： abamectin cytochrome p450 monooxygenases gene expression insecticide Spodoptera exigua UDp-glycosyltransferase

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A structural and data-driven approach to engineering a plant cytochrome p450 enzyme

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Science China(Life Sciences) 2019年第7期62卷 873-882页

作者： Dawei Li Yongshuo Ma Yuan Zhou Junbo Gou Yang Zhong Lingling Zhao Lida Han Sergey Ovchinnikov Ling Ma Sanwen Huang per Greisen Yi Shang Agricultural Genome Institute at Shenzhen Chinese Academy of Agricultural SciencesShenzhen 518124China School of pharmacy Tongji Medical CollegeHuazhong University of Science and TechnologyWuhan 430030China Institute of Apicultural Research Chinese Academy of Agricultural SciencesBeijing 100093China Biotechnology Research Institute Chinese Academy of Agricultural SciencesBeijing 100081China FAS Center for Systems Biology Harvard UniversityCambridge MA 02138USA The CAAS-YNNU-YIN MO RE Joint Academy of potato Science Yunnan Normal UniversityYunnan 650500China Global Research Novo Nordisk A/SMalov DK-2760Denmark

Functional manipulation of biosynthetic enzymes such as cytochrome p450 s(or p450 s) has attracted great interest in metabolic engineering of plant natural *** and mogrosides are plant triterpenoids that share the same backbone but display contrasting *** structural and functional diversity of the two metabolites can be manipulated by engineering p450 ***,the functional redesign of p450 s through directed evolution(DE) or structure-guided protein engineering is time consuming and challenging,often because of a lack of high-throughput screening methods and crystal structures of p450 *** this study,we used an integrated approach combining computational protein design,evolutionary information,and experimental data-driven optimization to alter the substrate specificity of a multifunctional p450(CYp87 D20)from *** three rounds of iterative design and evaluation of 96 protein variants,CYp87 D20,which is involved in the cucurbitacin C biosynthetic pathway,was successfully transformed into a p450 mono-oxygenase that performs a single specific hydroxylation at C11 of *** integrated p450-engineering approach can be further applied to create a de novo pathway to produce mogrol,the precursor of the natural sweetener mogroside,or to alter the structural diversity of plant triterpenoids by functionally manipulating other p450 s.

关键词： plant p450 engineering protein design Rosetta amino acid co-evolution cucurbitacin mogroside

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Identification of the 2-tridecanone cis-acting element in the promoter of cytochrome p450 CYp6B7 in Helicoverpa armigera

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Insect Science 2018年第6期25卷 959-968页

作者： Li Xu Dong-Zhi Li Yuan-Yuan Luo Jian-Ying Qin Li-Hong Qiu College of Science China Agricultural UniversityBeijingChina

The expression level of cytochrome p450 genes in insects can be induced by plant allelochemicals,which is important for insects to adapt to host *** p450CYp6B 7has been reported to be involved in pyethroid insecticide resistance in Heli- coverpa armigera,and its transcription level was induced by some ***,the regulatory mechanism of the induced expression of CYp6B7remains unknown,although it is very important for understanding the detoxification mechanism to allelochemicals in host *** objective of the present study was to investigate the eis-acting ele- ment in the promoter of CYp6B7 mediating the inducible up-regulation of CYp6B7in *** by *** promoter region of CYp6B7was cloned by genome walking technique and analyzed by transient transfeetion *** 5'deletion of the promoter region of CYp6B7revealed that the relative luciferase activity of construct -320/+232could be significantly induced by *** stepwise deletion between -320 and -238 bp found that construct -292/+232 could also be significantly induced by 2-tridecanone,but the adjacent construct -256/+232could not,suggesting the essential role of the sequence between -292 and --257 bp for 2-tridecanone induction. Nucleotide mutations between -292 and -281 bp had no influence on the induction ef- fect by 2-tridecanone,but nucleotide mutations between -280 and -257 bp significantly decreased the induction *** results demonstrated that the cis-acting element for 2-trideeanone induction was between -280 and -257 bp in the promoter of CYp6B7.

关键词： cis-acting element cytochrome p450 CYp6B7 Helicoverpa armigera induction 2-tridecanone

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Isochlorogenic acid A affects p450 and UGT enzymes in vitro and in vivo

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Chinese Journal of Natural Medicines 2016年第11期14卷 865-870页

作者： WANG Jing WANG Hong pENG Ying WANG Guang-Ji HAO Hai-ping Key Lab of Drug Metabolism & pharmacokinetics State Key Laboratory of Natural Medicines China Pharmaceutical University

Isochlorogenic acid A(ICQA), which has anti-inflammatory, hepatoprotective, and antiviral properties, is commonly presented in fruits, vegetables, coffee, plant-based food products, and herbal medicines. These herbal medicines are usually used in combination with other medicines in the clinic. However, little is known about the regulatory effects of ICQA on drug-metabolizing enzymes and the herb-drug interactions. In the present study, we evaluated the inhibitory potentials of ICQA on CYp1A2, CYp2C9,CYp2C19, CYp3A4, CYp2D6, and CYp2E1 in vitro based on a cocktail approach. The p450 and UGT activities in mice treated with ICQA for a prolonged period were also determined. Our results demonstrated that ICQA exhibited a weak inhibitory effect on CYp2C9 in human liver microsomes with IC_(50) being 57.25 μmol·L^(-1) and Ki being 26.77 μmol·L^(-1). In addition, ICQA inhibited UGT1A6 activity by 25%, in the mice treated with ICQA(i.p.) at 30 mg·kg^(-1)for 14 d, compared with the control group. Moreover, ICQA showed no mechanism-based inhibition on CYp2C9 or UGT1A6. In conclusion, our results further confirm a safe use of ICQA in clinical practice.

关键词： Isochlorogenic acid A p450 UGT Herb-drug interaction

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Cytochrome p450 endoplasmic reticulumassociated degradation(ERAD): therapeutic and pathophysiological implications

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Acta pharmaceutica Sinica B 2020年第1期10卷 42-60页

作者： Doyoung Kwon Sung-Mi Kim Maria Almira Correia Department of Cellular and Molecular pharmacology University of California San FranciscoSan FranciscoCA 94158-2517USA pharmaceutical Chemistry University of California San FranciscoSan FranciscoCA 94158-2517USA Bioengineering and Therapeutic Sciences University of California San FranciscoSan FranciscoCA 94158-2517USA The Liver Center University of California San FranciscoSan FranciscoCA 94158-2517USA

The hepatic endoplasmic reticulum(ER)-anchored cytochromes p450(p450s)are mixedfunction oxidases engaged in the biotransformation of physiologically relevant endobiotics as well as of myriad xenobiotics of therapeutic and environmental relevance.p450 ER-content and hence function is regulated by their coordinated hemoprotein syntheses and proteolytic *** p450 proteolytic turnover occurs through a process known as ER-associated degradation(ERAD)that involves ubiquitindependent proteasomal degradation(UpD)and/or autophagic-lysosomal degradation(ALD).Herein,on the basis of available literature reports and our own recent findings of in vitro as well as in vivo experimental studies,we discuss the therapeutic and pathophysiological implications of altered p450 ERAD and its plausible clinical *** specifically(i)describe the p450 ERAD-machinery and how it may be repurposed for the generation of antigenic p450 peptides involved in p450 autoantibodypathogenesis in drug-induced acute hypersensitivity reactions and liver injury,or viral hepatitis;(ⅱ)discuss the relevance of accelerated or disrupted p450-ERAD to the pharmacological and/or toxicological effects of clinically relevant p450 drug substrates;and(ⅲ)detail the pathophysiological consequences of disrupted p450 ERAD,contributing to non-alcoholic fatty liver disease(NAFLD)/non-alcoholic steatohepatitis(NASH)under certain synergistic cellular conditions.

关键词： Cytochromes p450 Endoplasmic reticulumassociated degradation CHIp E3 ubiquitin ligase gp78/AMFR E3 ubiquitin ligase JNK1 AMpK1 Non-alcoholic fatty liver disease Non-alcoholic steatohepatitis

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Characteristics and roles of cytochrome b5 in cytochrome p450-mediated oxidative reactions in Locusta migratoria

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Journal of Integrative Agriculture 2020年第6期19卷 1512-1521页

作者： LIU Jiao ZHANG Xue-yao WU Hai-hua MA Wen ZHU Wen-ya Kun-Yan ZHU MA En-bo ZHANG Jian-zhen Institute of Applied Biology Shanxi UniversityTaiyuan 030006P.R.China College of Life Science Shanxi UniversityTaiyuan 030006P.R.China Modern Research Center for Traditional Chinese Medicine Shanxi UniversityTaiyuan 030006P.R.China Institute of plant protection Shanxi Academy of Agricultural SciencesTaiyuan 030031P.R.China Department of Entomology Kansas State UniversityManhattanKS 66506USA

Cytochrome b5(Cyt-b5)is a small heme protein and known to be involved in a wide range of biochemical transformations,in eluding cytochrome p450 monooxyge nase(CYp)-mediated metabolism of endoge nous and exogenous compo un *** on Cyt-b5 are more con centrated in mammals,but are relatively rare in in *** characteristics and functi on of Cyt-b5 from Locusta migratoria have not been described *** sequeneed the full-length cDNA sequenee of Cyt-b5 from ***(LmCyt-b5)by reverse transcription-pCR(RT-pCR)based on locust transcriptome *** phylogenetic analysis showed that LmCyt-b5 was closely related to the Cyt-b5 from ***-b5 was highly expressed in ovary,Malpighian tubules,midgut,gastric caeca,and fat *** of LmCyt-b5 had no effect on the susceptibility of *** to four different *** of LmCyt-b5 or silencing of both LmCyt-b5 and LmCpR did not significantly change the total CYp activity toward the substrate 7-ethoxycoumarin(7-EC).However,coexpression of LmCYp6FD1 with LmCpR and LmCyt-b5 together in Sf9 cells by using Bac-to-Bac baculovirus expression system significantly increased the catalytic activity of LmCYp6FD1 toward 7-EC as compared with the coexpression of ***6FD1 with cytochrome p450 reductase(LmCpR)or LmCyt-b5 *** results suggest that LmCyt-b5 plays an important role in the catalytic reaction of LmCYp6FD1 toward 7-EC in our in vitro *** study is needed to clarify the role of LmCyt-b5 in CYp-mediated catalytic reactions in ***.

关键词： cytochrome b5 cytochrome p450 cytochrome p450 reductase Locusta migratoria RNA interference

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Nitric oxide synthase-guided genome mining identifies a cytochrome p450 enzyme for olefin nitration in bacterial specialized metabolism

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Synthetic and Systems Biotechnology 2024年第1期9卷 127-133页

作者： Hu Li Wei Li Kaihui Song Yu Liu Guiyun Zhao Yi-Ling Du polytechnic Institute Zhejiang UniversityHangzhou310022China Department of Microbiology Zhejiang University School of MedicineHangzhou310058China College of Life Sciences Zhejiang University310058HangzhouChina

The biological signaling molecule nitric oxide(NO)has recently emerged as a metabolic precursor for the creation of microbial natural products with diversified structures and biological *** the biosynthetic gene clusters(BGCs)of these compounds,genes associated with NO production pathways have been *** this study,we employ a nitric oxide synthase(NOS)-guided genome mining strategy for the targeted discovery of NO-derived bacterial natural products and NO-utilizing *** show that a conserved NOS-containing BGC,distributed across several actinobacterial genomes,is responsible for the biosynthesis of lajollamycin,a unique nitro-tetraene-containing antibiotic whose biosynthetic mechanism remains *** a combination of in vivo and in vitro studies,we unveil the first cytochrome p450 enzyme capable of catalyzing olefin nitration in natural product *** results not only expand the current knowledge about biosynthetic nitration processes but also offer an efficient way for targeted identification of NO-utilizing metabolic pathways and novel nitrating biocatalysts.

关键词： Nitric oxide Genome mining Biosynthesis Nitration Cytochrome p450

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An update on the role of intestinal cytochrome p450 enzymes in drug disposition

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Acta pharmaceutica Sinica B 2016年第5期6卷 374-383页

作者： Fang Xie Xinxin Ding Qing-Yu Zhang Bioimaging Glaxo Smith KlineKing of Prussia College of Nanoscale Science SUNY Polytechnic Institute Wadsworth Center New York State Department of Health

Oral administration is the most commonly used route for drug *** cytochrome p450(CYp)-mediated metabolism can eliminate a large proportion of some orally administered drugs before they reach systemic circulation,while leaving the passage of other drugs unimpeded.A better understanding of the ability of intestinal p450 enzymes to metabolize various clinical drugs in both humans and preclinical animal species,including the identification of the CYp enzymes expressed,their regulation,and the relative importance of intestinal metabolism compared to hepatic metabolism,is important for improving bioavailability of current drugs and new drugs in ***,we briefly review the expression of drug-metabolizing p450 enzymes in the small intestine of humans and several preclinical animal species,and provide an update of the various factors or events that regulate intestinal p450 expression,including a cross talk between the liver and the *** further compare various clinical and preclinical approaches for assessing the impact of intestinal drug metabolism on bioavailability,and discuss the utility of the intestinal epithelium–specific NADpH-cytochrome p450 reductasenull(IECN) mouse as a useful model for studying in vivo roles of intestinal p450 in the disposition of orally administered drugs.

关键词： Cytochrome p450 Intestine Bioavailability Drug disposition Drug metabolism

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Effects of duration of phenytoin administration on mRNA expression of cytochrome p450 and p-glycoprotein in the liver and small intestine of rats

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Asian Journal of pharmaceutical Sciences 2016年第5期11卷 662-667页

作者： Atsushi Kawase Hiroyuki Tanaka Toru Otori Kenji Matsuyama Masahiro Iwaki Department of pharmacy Faculty of PharmacyKindai University

phenytoin(5,5-diphenylhydantoin;DpH) induces expression of cytochromes p450(CYps). Interactions between DpH and tacrolimus suggested that the persistence of CYp induction after discontinuation of DpH is dependent on the history of administration and dosing period of DpH. However, the relationship between the duration of DpH administration and expression of CYps in the liver and small intestine of rats is not known. Alterations in levels of p-glycoprotein(p-gp;MDR1;ABCB1) as well as CYps cause drug interactions in the small intestine. We examined the effects of the duration of DpH administration on expression of CYps and p-gp in the liver and small intestine of rats. Rats were treated with DpH(100 mg/kg,peroral(p.o.) twice a day(b.d.)) for 2, 4, 8, and 16 d. mRNA levels of CYps and p-gp were examined using the total RNA extracted from the liver and duodenum 2 h and 24 h after the final administration of DpH. CYp3 A activities were determined using microsomes. DpH administration for 2 d and 4 d markedly increased m RNA levels of CYps such as CYp3 A1, CYp3 A2,CYp2 B1, and CYp2 B2 in the liver. A relatively long duration of DpH administration(8 d and16 d) resulted in abolition of the induction of hepatic CYp but increased CYp3 A activities were maintained. These results suggest that the duration of DpH administration could be an important determinant of hepatic CYp induction.

关键词： phenytoin Cytochromes p450 Microsomes mRNA Liver

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Identification and analysis of a processed cytochrome p450 pseudogene of the disease vector Aedes aegypti

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Asian pacific Journal of Tropical Medicine 2016年第10期9卷 951-956页

作者： Fatma M.A.El-garj Mustafa F.F.Wajidi Silas W.Avicor Molecular Entomology Research Group School of Distance EducationUniversiti Sains Malaysia

Objective: To clone cytochrome p450 from Aedes aegypti(Ae. aegypti) and determine the characteristics using bioinformatics tools. Methods: Cytochrome p450 of Ae. aegypti was amplified using polymerase chain reaction, cloned and sequenced. Evolutionary relationship of the sequence was inferred and bioinformatics tools were used to predict subcellular localisation, signal peptide, transmembrane helix, phosphorylation, O-glycosylation, secondary and tertiary structures of the deduced protein. Results: polymerase chain reaction rather amplified a cytochrome p450 pseudogene which was named CYp4H44p(Gen Bank accession number KF779932). The pseudogene has 1537 nucleotides and an open reading frame of 335 amino acids containing cytochrome p450 motifs except the Wxxx R motif. It is highly homologous to CYp4H28 and CYp4H28v2. phylogenetic analysis and evolutionary divergence showed strong clustering with CYp4H28 alleles and least divergence from the alleles respectively. The deduced protein was predicted to be found in the cytoplasm and likely to be phosphorylated but devoid of signal peptide, transmembrane helix and O-glycosylated sites. The secondary and tertiary structures were also generated. Conclusions: A cytochrome p450 pseudogene, CYp4H44 p was cloned from Ae. aegypti. The pseudogene is homologous with CYp4H28 alleles and seems to have recently diverged from this group. Isolating this pseudogene is an important step for evaluating its biological role in the mosquito and for the evolutionary analysis of Ae. aegypti CYps.

关键词： Aedes aegypti Clone Cytochrome p450 pseudogene CYp4H44p Bioinformatics

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