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1

Article

The opium poppy genome and morphinan production

Guo, Li ; Winzer, Thilo ; Yang, Xiaofei ; [et al.]

2018

ISSN: 0036-8075

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Language: English

In: Science (American Association for the Advancement of Science), 2018-10-19, Vol.362 (6412), p.343-347

Description: Morphinan-based painkillers are derived from opium poppy ( L.). We report a draft of the opium poppy genome, with 2.72 gigabases assembled into 11 chromosomes with contig N50 and scaffold N50 of 1.77 and 204 megabases, respectively. Synteny analysis suggests a whole-genome duplication at ~7.8 million years ago and ancient segmental or whole-genome duplication(s) that occurred before the Papaveraceae-Ranunculaceae divergence 110 million years ago. Syntenic blocks representative of phthalideisoquinoline and morphinan components of a benzylisoquinoline alkaloid cluster of 15 genes provide insight into how this cluster evolved. Paralog analysis identified P450 and oxidoreductase genes that combined to form the gene fusion essential for morphinan biosynthesis in opium poppy. Thus, gene duplication, rearrangement, and fusion events have led to evolution of specialized metabolic products in opium poppy.

Subject(s): Addiction ; Analgesics ; Benzylisoquinolines - metabolism ; Biological evolution ; Biosynthesis ; Chemical properties ; Chromosomes ; Clusters ; Divergence ; Drug abuse ; Drug trafficking ; Evolution, Molecular ; Gene Duplication ; Gene Fusion ; Gene Order ; Gene rearrangement ; Genes ; Genetic aspects ; Genome, Plant ; Genomes ; Metabolism ; Morphinans - metabolism ; Multigene Family ; NADPH-Ferrihemoprotein Reductase - genetics ; Narcotics ; Opiates ; Opioids ; Opium poppy ; Oxidoreductase ; Papaver - genetics ; Papaver - metabolism ; Papaver somniferum ; Phthalideisoquinoline ; Plant Proteins - genetics ; Production processes ; Proteins ; Reproduction (copying) ; Synteny

ISSN: 0036-8075

E-ISSN: 1095-9203

DOI: 10.1126/science.aat4096

Source: Academic Search Ultimate

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URL: https://www.ncbi.nlm.nih.gov/pubmed/30166436$$D View this record in MEDLINE/PubMed

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2

Article

A Papaver somniferum 10-Gene Cluster for Synthesis of the Anticancer Alkaloid Noscapine

WINZER, Thilo ; GAZDA, Valeria ; WANKER, Carol ; [et al.]

2012

ISSN: 0036-8075

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Language: English

In: Science (American Association for the Advancement of Science), 2012-06-29, Vol.336 (6089), p.1704-1708

Description: Noscapine is an antitumor alkaloid from opium poppy that binds tubulin, arrests metaphase, and induces apoptosis in dividing human cells. Elucidation of the biosynthetic pathway will enable improvement in the commercial production of noscapine and related bioactive molecules. Transcriptomic analysis revealed the exclusive expression of 10 genes encoding five distinct enzyme classes in a high noscapine-producing poppy variety, HN1. Analysis of an F₂ mapping population indicated that these genes are tightly linked in HN1, and bacterial artificial chromosome sequencing confirmed that they exist as a complex gene cluster for plant alkaloids. Virus-induced gene silencing resulted in accumulation of pathway intermediates, allowing gene function to be linked to noscapine synthesis and a novel biosynthetic pathway to be proposed.

Subject(s): Alkaloids ; Anticancer properties ; Antineoplastic Agents, Phytogenic - biosynthesis ; Biological and medical sciences ; Biosynthesis ; Capsules ; Classical genetics, quantitative genetics, hybrids ; Clusters ; Cough ; Enzymes ; Flowers & plants ; Fundamental and applied biological sciences. Psychology ; Gene silencing ; Genes ; Genes, Plant ; Genetic aspects ; Genetics of eukaryotes. Biological and molecular evolution ; Genomes ; Latex ; Libraries ; Low level ; Molecular Sequence Data ; Morphinans ; Multigene Family ; Narcotics ; Noscapine - metabolism ; Open reading frames ; Papaver - enzymology ; Papaver - genetics ; Papaver - metabolism ; Papaver somniferum ; Pharmaceutical sciences ; Physiological aspects ; Plant biology ; Poppies ; Pteridophyta, spermatophyta ; REPORTS ; Research ; Synthesis ; Vegetals

ISSN: 0036-8075

E-ISSN: 1095-9203

DOI: 10.1126/science.1220757

Source: JSTOR Life Sciences

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URL: http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26074305$$DView record in Pascal Francis

URL: https://www.ncbi.nlm.nih.gov/pubmed/22653730$$D View this record in MEDLINE/PubMed

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3

Article

Over 100 Million Years of Enzyme Evolution Underpinning the Production of Morphine in the Papaveraceae Family of Flowering Plants

Li, Yi ; Winzer, Thilo ; He, Zhesi ; [et al.]

2020

ISSN: 2590-3462

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Language: English

In: Plant communications, 2020-03-09, Vol.1 (2), p.100029-100029

Description: Phylogenomic analysis of whole genome sequences of five benzylisoquinoline alkaloid (BIA)-producing species from the Ranunculales and Proteales orders of flowering plants revealed the sequence and timing of evolutionary events leading to the diversification of these compounds. (S)-Reticuline is a pivotal intermediate in the synthesis of many BIAs and our analyses revealed parallel evolution between the two orders, which diverged ∼122 million years ago (MYA). Berberine is present in species across the entire Ranunculales, and we found co-evolution of genes essential for production of the protoberberine class. The benzophenanthridine class, which includes the antimicrobial compound sanguinarine, is specific to the Papaveraceae family of Ranunculales, and biosynthetic genes emerged after the split with the Ranunculaceae family ∼110 MYA but before the split of the three Papaveraceae species used in this study at ∼77 MYA. The phthalideisoquinoline noscapine and morphinan class of BIAs are exclusive to the opium poppy lineage. Ks estimation of paralogous pairs indicates that morphine biosynthesis evolved more recently than 18 MYA in the Papaver genus. In the preceding 100 million years gene duplication, neofunctionalization and recruitment of additional enzyme classes, combined with gene clustering, gene fusion, and gene amplification, resulted in emergence of medicinally valuable BIAs including morphine and noscapine. Annotated genomes of five benzylisoquinoline alkaloid (BIA)-producing species are used to conduct gene tree analysis and uncover the events leading to emergence of major BIA biosynthetic pathways in Ranunculales. Ks estimation of key paralogous pairs revealed that morphine biosynthesis evolved more recently than 18 million years ago in the Papaver genus. Contrary to previous reports, this study indicates that BIA biosynthesis evolved independently in the Ranunculales and Proteales orders.

Subject(s): benzylisoquinoline alkaloids ; gene clusters ; gene fusion ; gene tree analysis ; metabolic pathway evolution ; plant genomes

ISSN: 2590-3462

E-ISSN: 2590-3462

DOI: 10.1016/j.xplc.2020.100029

Source: PubMed Central

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4

Article

Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein

Winzer, Thilo ; Kern, Marcelo ; King, Andrew J. ; [et al.]

2015

ISSN: 0036-8075

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Language: English

In: Science (American Association for the Advancement of Science), 2015-07-17, Vol.349 (6245), p.309-312

Description: Morphinan alkaloids from the opium poppy are used for pain relief. The direction of metabolites to morphinan biosynthesis requires isomerization of (S)- to (R)-reticuline. Characterization of high-reticuline poppy mutants revealed a genetic locus, designated STORR [(S)- to (R)-reticuline] that encodes both cytochrome P450 and oxidoreductase modules, the latter belonging to the aldo-keto reductase family. Metabolite analysis of mutant alleles and heterologous expression demonstrate that the P450 module is responsible for the conversion of (S)-reticuline to 1,2-dehydroreticuline, whereas the oxidoreductase module converts 1,2-dehydroreticuline to (R)-reticuline rather than functioning as a P450 redox partner. Proteomic analysis confirmed that these two modules are contained on a single polypeptide in vivo. This modular assembly implies a selection pressure favoring substrate channeling. The fusion protein STORR may enable microbial-based morphinan production.

Subject(s): Biosynthesis ; Enzymes ; Metabolites ; Modules ; Morphine ; Narcotics ; Pathways ; Poppies ; Proteins ; REPORTS

ISSN: 0036-8075

E-ISSN: 1095-9203

DOI: 10.1126/science.aab1852

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5

Article

Flavonoid Versus Artemisinin Anti-malarial Activity in Artemisia annua Whole-Leaf Extracts

Czechowski, Tomasz ; Rinaldi, Mauro A ; Famodimu, Mufuliat Toyin ; [et al.]

2019

ISSN: 1664-462X

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Language: English

In: Frontiers in plant science, 2019-07-30, Vol.10, p.984-984

Description: Artemisinin, a sesquiterpene lactone produced by Artemisia annua glandular secretory trichomes, is the active ingredient in the most effective treatment for uncomplicated malaria caused by Plasmodium falciparum parasites. Other metabolites in A. annua or related species, particularly flavonoids, have been proposed to either act as antimalarials on their own or act synergistically with artemisinin to enhance antimalarial activity. We identified a mutation that disrupts the CHALCONE ISOMERASE 1 (CHI1) enzyme that is responsible for the second committed step of flavonoid biosynthesis. Detailed metabolite profiling revealed that chi1-1 lacks all major flavonoids but produces wildtype artemisinin levels, making this mutant a useful tool to test the antiplasmodial effects of flavonoids. We used whole-leaf extracts from chi1-1 and mutant lines impaired in artemisinin production in bioactivity in vitro assays against intraerythrocytic P. falciparum Dd2. We found that chi1-1 extracts did not differ from wild-type extracts in antiplasmodial efficacy nor initial rate of cytocidal action. Furthermore, extracts from the A. annua cyp71av1-1 mutant and RNAi lines impaired in amorpha-4,11-diene synthase gene expression, which are both severely compromised in artemisinin biosynthesis but unaffected in flavonoid metabolism, showed very low or no antiplasmodial activity. These results demonstrate that in vitro bioactivity against P. falciparum of flavonoids is negligible when compared to that of artemisinin.

Subject(s): Artemisia annua ; artemisinin ; Bioflavonoids ; Care and treatment ; chalcone isomerase ; Comparative analysis ; Flavones ; Flavonoids ; Genetic aspects ; Life Sciences & Biomedicine ; Malaria ; Plant Science ; Plant Sciences ; Plasmodium falciparum ; Research ; Science & Technology ; Wormwood

ISSN: 1664-462X

E-ISSN: 1664-462X

DOI: 10.3389/fpls.2019.00984

Source: Web of Science - Science Citation Index Expanded - 2019〈img src="http://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" /〉

Source: PubMed Central

Source: DOAJ Directory of Open Access Journals - Not for CDI Discovery

URL: https://www.ncbi.nlm.nih.gov/pubmed/31417596$$D View this record in MEDLINE/PubMed

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6

Article

The Genetic Map of Artemisia annua L. Identifies Loci Affecting Yield of the Antimalarial Drug Artemisinin

GRAHAM, Ian A ; BESSER, Katrin ; LARSON, Tony R ; [et al.]

2010

ISSN: 0036-8075

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Language: English

In: Science (American Association for the Advancement of Science), 2010-01-15, Vol.327 (5963), p.328-331

Description: Artemisinin is a plant natural product produced by Artemisia annua and the active ingredient in the most effective treatment for malaria. Efforts to eradicate malaria are increasing demand for an affordable, high-quality, robust supply of artemisinin. We performed deep sequencing on the transcriptome of A annua to identify genes and markers for fast-track breeding. Extensive genetic variation enabled us to build a detailed genetic map with nine linkage groups. Replicated field trials resulted in a quantitative trait loci (QTL) map that accounts for a significant amount of the variation in key traits controlling artemisinin yield. Enrichment for positive QTLs in parents of new high-yielding hybrids confirms that the knowledge and tools to convert A annua into a robust crop are now available.

Subject(s): Agronomy. Soil science and plant productions ; Antimalarials ; Antimalarials - metabolism ; Artemisia ; Artemisia - genetics ; Artemisia - metabolism ; Artemisinins ; Artemisinins - metabolism ; Biological and medical sciences ; Cellular Biology ; Chromosome Mapping ; Construction ; Crosses, Genetic ; DNA, Complementary ; Flowers & plants ; Fundamental and applied biological sciences. Psychology ; Gene Expression Profiling ; Genes ; Genes, Plant ; Genetic aspects ; Genetic Association Studies ; Genetic diversity ; Genetic mapping ; Genetic variation ; Genetics ; Genetics and breeding of economic plants ; Genotype & phenotype ; Genotypes ; Humans ; Hybridity ; Life Sciences ; Linkage groups ; Loci ; Malaria ; Malaria - drug therapy ; Markers ; Medical genetics ; Methods ; Mutation ; Parents ; Phenotype ; Phenotypic traits ; Plant biology ; Plants ; Polymorphism, Single Nucleotide ; Population growth ; Prescription drugs ; Quantitative genetics ; Quantitative Trait Loci ; Reports ; Research ; Sequence Analysis, DNA ; Sequencing

ISSN: 0036-8075

E-ISSN: 1095-9203

DOI: 10.1126/science.1182612

Source: JSTOR Life Sciences

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URL: https://www.ncbi.nlm.nih.gov/pubmed/20075252$$D View this record in MEDLINE/PubMed

URL: https://hal.inrae.fr/hal-02661956$$DView record in HAL

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7

Article

Seven Lotus japonicus Genes Required for Transcriptional Reprogramming of the Root during Fungal and Bacterial Symbiosis

Kistner, Catherine ; Winzer, Thilo ; Pitzschke, Andrea ; [et al.]

2005

ISSN: 1040-4651

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Language: English

In: The Plant cell, 2005-08-01, Vol.17 (8), p.2217-2229

Description: A combined genetic and transcriptome analysis was performed to study the molecular basis of the arbuscular mycorrhiza (AM) symbiosis. By testing the AM phenotype of nodulation-impaired mutants and complementation analysis, we defined seven Lotus japonicus common symbiosis genes (SYMRK, CASTOR, POLLUX, SYM3, SYM6, SYM15, and SYM24) that are required for both fungal and bacterial entry into root epidermal or cortical cells. To describe the phenotype of these mutants at the molecular level, we screened for differentiating transcriptional responses of mutant and wild-type roots by large-scale gene expression profiling using cDNA-amplified fragment length polymorphism. Two percent of root transcripts was found to increase in abundance during AM development, from which a set of AM-regulated marker genes was established. A Ser-protease (SbtS) and a Cys-protease (CysS) were also activated during root nodule development. AM-induced transcriptional activation was abolished in roots carrying mutations in common symbiosis genes, suggesting a central position of these genes in a pathway leading to the transcriptional activation of downstream genes. By contrast, AM fungus-induced gene repression appeared to be unaffected in mutant backgrounds, which indicates the presence of additional independent signaling pathways.

Subject(s): Arabidopsis ; Bacteria ; Bacterial Physiological Phenomena ; Castor ; Complementary DNA ; Epidermal cells ; Fungi ; Fungi - physiology ; Genes ; Genes, Plant ; Genetic aspects ; Host-bacteria relationships ; Infections ; Inoculation ; Lotus (Legumes) ; Lotus - genetics ; Lotus - growth & development ; Lotus - microbiology ; Lotus japonicus ; Molecular Sequence Data ; Mutation ; Mycorrhizas ; Phanerogams ; Plant cells ; Plant roots ; Plants ; Roots (Botany) ; Symbiosis ; Transcription, Genetic

ISSN: 1040-4651

E-ISSN: 1532-298X

DOI: 10.1105/tpc.105.032714

Source: JSTOR Life Sciences

Source: JSTOR Ecology & Botany II

Source: Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals

URL: https://www.ncbi.nlm.nih.gov/pubmed/15980262$$D View this record in MEDLINE/PubMed

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8

Article

Distinct Roles of Lotus japonicus SYMRK and SYM15 in Root Colonization and Arbuscule Formation

Demchenko, Kirill ; Winzer, Thilo ; Stougaard, Jens ; [et al.]

2004

ISSN: 0028-646X

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Language: English

In: The New phytologist, 2004-08-01, Vol.163 (2), p.381-392

Description: • The colonization of Lotus japonicus roots by the arbuscular mycorrhizal fungus Glomus intraradices was analysed in plant mutants affected in the symbiosis genes, SYM15 or SYMRK. SYMRK encodes an LRR receptor-like kinase that is, like the SYM15 gene, essential for both mycorrhizal and rhizobial symbioses. • Different colonization patterns were observed in growing vs meristematically arrested roots. • Three steps in the interaction were differentially impaired in the mutants: surface opening, where the anticlinal cell walls of two adjacent epidermal cells separate from each other in the vicinity of fungal hyphae; intracellular passage of hyphae through an exodermal cell and an adjacent cell of the outermost cortical layer; and arbuscule formation in cells of the two innermost cortical layers. • The combined results indicate that LjSYMRK is required for the intracellular passage through exodermis and outermost cortical cell layer whereas LjSYM15 is required for surface opening and arbuscule formation.

Subject(s): Alleles ; arbuscular mycorrhiza ; arbuscule ; Cell walls ; Epidermal cells ; Fungi ; Glomus intraradices ; Hyphae ; Lotus japonicus ; Microbial colonization ; Plant cells ; Plant roots ; Plants ; root meristem ; saprophytic growth ; signal transduction ; Symbiosis

ISSN: 0028-646X

E-ISSN: 1469-8137

DOI: 10.1111/j.1469-8137.2004.01123.x

Source: JSTOR Life Sciences

Source: Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals

URL: https://www.ncbi.nlm.nih.gov/pubmed/33873620$$D View this record in MEDLINE/PubMed

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9

Article

High-density genetic mapping identifies new susceptibility loci for rheumatoid arthritis

Eyre, Steve ; Bowes, John ; Diogo, Dorothee ; [et al.]

2012

ISSN: 1061-4036 ISSN: 1546-1718

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Language: English

In: Nature genetics, 2012-12, Vol.44 (12), p.1336-1340

Description: Using the Immunochip custom SNP array, which was designed for dense genotyping of 186 loci identified through genome-wide association studies (GWAS), we analyzed 11,475 individuals with rheumatoid arthritis (cases) of European ancestry and 15,870 controls for 129,464 markers. We combined these data in a meta-analysis with GWAS data from additional independent cases (n = 2,363) and controls (n = 17,872). We identified 14 new susceptibility loci, 9 of which were associated with rheumatoid arthritis overall and five of which were specifically associated with disease that was positive for anticitrullinated peptide antibodies, bringing the number of confirmed rheumatoid arthritis risk loci in individuals of European ancestry to 46. We refined the peak of association to a single gene for 19 loci, identified secondary independent effects at 6 loci and identified association to low-frequency variants at 4 loci. Bioinformatic analyses generated strong hypotheses for the causal SNP at seven loci. This study illustrates the advantages of dense SNP mapping analysis to inform subsequent functional investigations.

Subject(s): Arthritis, Rheumatoid - genetics ; ASSOCIATION ; Autoantibodies - blood ; Autoantibodies - genetics ; Autoimmune diseases ; Biological and medical sciences ; Chromosome Mapping - instrumentation ; Chromosome Mapping - methods ; Chromosomes ; Classical genetics, quantitative genetics, hybrids ; Clinical Medicine ; CORONARY-HEART-DISEASE ; Disease susceptibility ; Diseases of the osteoarticular system ; EXPRESSION ; Female ; Fundamental and applied biological sciences. Psychology ; Genetic aspects ; Genetic Loci ; Genetic Predisposition to Disease ; Genetics of eukaryotes. Biological and molecular evolution ; Genome-Wide Association Study ; Humans ; Inflammatory joint diseases ; INTERLEUKIN-6 RECEPTOR ; Klinisk medicin ; Male ; Medical and Health Sciences ; Medical research ; Medical sciences ; Medicin och hälsovetenskap ; METAANALYSIS ; Methods, theories and miscellaneous ; Oligonucleotide Array Sequence Analysis ; Physiological aspects ; Polymorphism, Single Nucleotide ; Research ; Reumatologi och inflammation ; Rheumatoid arthritis ; Rheumatology and Autoimmunity ; RISK LOCI ; Single nucleotide polymorphisms ; Studies ; Whites - genetics

ISSN: 1061-4036

ISSN: 1546-1718

E-ISSN: 1546-1718

DOI: 10.1038/ng.2462

Source: Academic Search Ultimate

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URL: https://www.ncbi.nlm.nih.gov/pubmed/23143596$$D View this record in MEDLINE/PubMed

URL: http://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-63019$$DView record from Swedish Publication Index

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10

Article

Genome-wide association study identifies eight loci associated with blood pressure

Newton-Cheh, Christopher ; Johnson, Toby ; Gateva, Vesela ; [et al.]

2009

ISSN: 1061-4036 ISSN: 1546-1718

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Language: English

In: Nature genetics, 2009-06, Vol.41 (6), p.666-676

Description: Elevated blood pressure is a common, heritable cause of cardiovascular disease worldwide. To date, identification of common genetic variants influencing blood pressure has proven challenging. We tested 2.5 million genotyped and imputed SNPs for association with systolic and diastolic blood pressure in 34,433 subjects of European ancestry from the Global BPgen consortium and followed up findings with direct genotyping (N

Subject(s): Adaptor Proteins, Signal Transducing ; Annan klinisk medicin ; BARTTERS-SYNDROME ; Biological and medical sciences ; Blood pressure ; Blood Pressure - genetics ; Cardiac and Cardiovascular Systems ; Cardiovascular disease ; Cardiovascular diseases ; Cardiovascular Diseases - genetics ; Cardiovascular Diseases - physiopathology ; CELL-DIFFERENTIATION ; Chromosome Mapping ; Clinical Medicine ; COMMON VARIANTS ; Cytochrome P-450 CYP1A2 - genetics ; Data analysis ; Diastole - genetics ; DNA-Binding Proteins - genetics ; Endocrinology and Diabetes ; Endokrinologi och diabetes ; Europe ; Fibroblast Growth Factor 5 - genetics ; Fundamental and applied biological sciences. Psychology ; Gene loci ; Genetic aspects ; Genetic Variation ; Genetics of eukaryotes. Biological and molecular evolution ; Genome-Wide Association Study ; Genomics ; Humans ; Hypertension ; India ; Intracellular Signaling Peptides and Proteins ; Kardiologi ; Klinisk medicin ; LOW-RENIN HYPERTENSION ; Medical and Health Sciences ; MEDICIN ; Medicin och hälsovetenskap ; MEDICINE ; Meta-analysis ; Methylenetetrahydrofolate Reductase (NADPH2) - genetics ; METHYLENETETRAHYDROFOLATE REDUCTASE GENE ; MUTATIONS ; Open Reading Frames - genetics ; Other Clinical Medicine ; Phospholipase C delta - genetics ; Physiological aspects ; POLYMORPHISM ; Polymorphism, Single Nucleotide ; POPULATION ; Proteins - genetics ; PUBLIC-HEALTH ; Research ; RISK ; Risk factors ; Single nucleotide polymorphisms ; Statistics ; Steroid 17-alpha-Hydroxylase - genetics ; Studies ; Systole - genetics ; Whites - genetics

ISSN: 1061-4036

ISSN: 1546-1718

E-ISSN: 1546-1718

DOI: 10.1038/ng.361

Source: Academic Search Ultimate

Source: Nature Journals Online

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URL: https://www.ncbi.nlm.nih.gov/pubmed/19430483$$D View this record in MEDLINE/PubMed

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URL: http://kipublications.ki.se/Default.aspx?queryparsed=id:118831963$$DView record from Swedish Publication Index

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