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Metabolic engineering of natural products for plant, animal, and human health Richard Dixon Plant Biology Division Samuel Roberts Noble Foundation Ardmore, Oklahoma and Centre for Novel Agricultural Products, Department of Biology, University of York Molecular biology of plant natural products We study…… We do……. •Lignin • Phytochemistry – Forage digestibility • Enzymology • Isoflavonoids • Gene discovery through – Phytoalexins genomics – Phytoestrogens • Pathway engineering • Condensed tannins – Understanding pathways – Pasture bloat – Addressing function – Health benefits – Improving traits • Triterpene saponins – Palatability – Plant defense – Adjuvants Natural products from legumes 650 genera, >18,000 examined phytochemically • Lignins • Flavonoids • Isoflavonoids • Terpenoids (di-, sesqui- and tri-triterpenes) • Alkaloids (eg. quinolizidine, dipiperidine) • Coumarins • Anthraquinones • Non-protein amino acids • Cyanogenic glycosides IntegratedIntegrated functionalfunctional genomicsgenomics ofof thethe modelmodel legumelegume MedicagoMedicago truncatulatruncatula AAAA AAAA MDKLLV... OH HO CH2OH Agronomic traits in Medicago truncatula • Nitrogen fixation • Mineral nutrition • Forage quality – Protein content – Digestibility – Palatability –Bloat – Silage properties • Disease resistance • Drought tolerance • Grazing tolerance • Source of health-promoting natural products Re-designing alfalfa as the perfect forage Alfalfa has a high protein content and is an excellent quality forage, BUT….. Disease problems (cotton root rot) Digestibility decreases with increasing maturity Causes pasture bloat AA structuralstructural modelmodel ofof ligninlignin Lignin and forage digestibility USDFRC estimates that 15 a 10% increase in fiber digestibility would result in an annual $350 10 million increase in milk/beef production and = 2.8 million tons 5 decrease in manure Klason lignin (% of DM) solids produced each year. 0 1/2345678 Internode number COMT and CCOMT: targets for lignin engineering CCOMT COMT EffectsEffects ofof COMTCOMT andand CCOMTCCOMT downdown-- regulationregulation onon ligninlignin compositioncomposition Transgenic COMT CCOMT S G 5-OHG Lines pkat/mg pkat/mg Lignin Lignin Lignin Wild type 5.98 22.35 158.8 305.4 0.0 COMT downregulated 1.24 22.26 8.6 246.1 8.8 CCOMT 14.39 0.78 159.1 150.2 0.0 downregulated COMT & CCOMT 0.78 5.59 54.0 223.7 0.0 downregulated Guo et al. (2001) Plant Cell 13: 73-88 In-rumen digestibility of transgenic alfalfa forage in fistulated steers 0.9 0.88 0.86 ck 0.84 SC5 ACC305 Guo et al. Transgenic D ig estib0.82 ility Research 10, 457- 0.8 464, 2001 0.78 020406080 Time in Rumen (h) Summary of field data (3 States) 59 58 57 56 55 54 IVD53 % • 52 LSD .05 = 1.14 51 50 49 48 Null 10.5 10.0 WL342 9.5 COMT-4 ADL % 9.0 COMT-5 8.5 COMT-310 8.0 CCOMT-305 Null In vitro digestibility CCOMT-315 WL342 COMT-4 COMT-5 COMT-310 CCOMT-305 Acid detergent lignin CCOMT-315 (lower stem) Profiling of soluble phenolics by HPLC 16K M. truncatula oligo array vs alfalfa stem RNA Absorbence (mAU) Control (leaf) Control (stem) COMT (stem) CCOMT (stem) 5.0 7.5 10.0 12.5 15.0 17.5 20.0 22.5 25.0 27.5 30.0 32.5 35.0 37.5 40.0 42.5 45.0 47.5 50.0 Retention time (min) E Factor1 Leaf F Factor2 B A Factor3 Stem C D Principle component analysis Data of Fang Chen and Srinu Reddy 2-D NMR reveals novel structures in lignin from COMT down-regulated alfalfa Marita et al. Phytochemistry, 2003 Re-designing alfalfa as the perfect forage • Alfalfa has a high protein content and is an excellent quality forage, BUT….. – Disease problems (cotton root rot) – Digestibility decreases with increasing maturity – Causes pasture bloat Condensed tannins (proanthocyanidins) are oligomers or polymers of flavonoid (i.e.flavan-3-ol) linked R by carbon-carbon bonds. 2 OH 5' 4' may contain 2-50 or greater 1' HO O 2' flavonoid units. 3' 1 2 R1 3 differ in flavonoid units (R1, 4 R n OH 2 R2 =H or OH) and interflavan OH bond sites. OH 5'4' 1' B HO O 2' 8 1 3' R 7 2 1 produce anthocyanidin after A C 3 5 4 HCl-butanol hydrolysis OH produce blue coloration with OH dimethylaminocinnamaldehyde Activities of condensed tannins • Bind to proteins, and reduce their rate of degradation (eg. tanning of leather, reduction of rumen fermentation). Help prevent pasture bloat. •In Medicago and white clover, CTs accumulate in the seed coat but not in the leaves • Toxic to fungi, bacteria and insects. • Antioxidant-cardiovascular benefits (polymers and monomers) • Flavor and astringency (tea, wine, fruit juices) • Urinary tract health (cranberry) BiosynthesisBiosynthesis ofof condensedcondensed tanninstannins andand anthocyaninsanthocyanins.. ban WT M.truncatula homolog of Arabidopsis BAN gene was identified by EST database mining -developing seed library. 1 MASIKQIEIEKKKACVIGGTGFVASLLIKQLLEKGYAVNT 1 MDQT-LTHTGSKKACVIGGTGNLASILIKHLLQSGYKVNT 41 TVRDLDSANKTSHLIALQSLGELNLFKAELTIEEDFDAPI 40 TVRDPENEKKIAHLRQLQELGDLKIFKADLTDEDSFESSF 81 SGCELVFQLATPVNFASQDPENDMIKPAIKGVLNVLKACV 80 SGCEYIFHVATPINFKSEDPEKDMIKPAIQGVINVLKSCL 121 RAKEVKRVILTSSAAAVTINELEGTGHVMDETNWSDVEFL 120 KSKSVKRVIYTSSAAAVSINNLSGTGLVMNEENWTDIDFL 161 NTAKPPTWGYPVSKVLAEKAAWKFAEENNIDLITVIPTLT 160 TEEKPFNWGYPISKVLAEKKAWEFAEENKINLVTVIPALI 201 IGPSLTQDIPSSVAMGMSLLTGNDFLINALKGMQFLSGSI 200 AGNSLLSDPPSSLSLSMSFITGKEMHVTGLKEMQKLSGSI 241 SITHVEDICRAHIFVAEKESTSGRYICCAHNTSVPELAKF 240 SFVHVDDLARAHLFLAEKETASGRYICCAYNTSVPEIADF 281 LSKRYPQYKVPTEFDDFPSKAKLIISSGKLIKEGFSFKHS 280 LIQRYPKYNVLSEFEEGLSIPKLTLSSQKLINEGFRFEYG MtBAN 321 IAETFDQTVEYLKTQGI----K. Identity, 59% 320 INEMYDQMIEYFESKGLIKAKES AtABN R2 R2 OH OH 6' 5' 5' 4' 4' 1' 1' HO 7 O 2' LAR HO 7 O 2' 8 1 3' R 3' 2 1 8 1 2 R1 6 3 6 3 5 4 5 4 OH OH OH OH WT OH Flavan-3-ol Leucoanthocyanidin 35S-BAN R2 ANS R2 6' OH 5' OH 4' 6' 5' 1' 4' HO 7 O 2' 1' 8 + 3' R HO 7 O 2' 2 1 8 1 3' R 6 ANR 2 1 5 4 6 3 3 OH 5 4 OH OH Anthocyanidin ban OH R2 OH 5' 4' 1' HO O 2' 3' 1 2 R1 3 4 R n OH 2 OH OH 5'4' 1' HO O 2' 8 1 3' R 7 2 1 3 5 4 OH OH WT Anthocyanins Condensed tannins CT Xie et al. Science, 299, 396-399, 2003 Ectopic expression of MtBAN in tobacco flowers reduces anthocyanin content and results in accumulation of tannins 7 6 5 4 528nm)3 2 Anthocyanidin1 (absorbance at 0 B-13-B 70 B-19-A 60 50 B-19-C 40 B-21-B FW)30 Plant lines 20 C-4 10 CT (µg cyanidin equivalents/g 0 C-5 121-1-B B-13-B Comparison of 121-4-B anthocyanin content B-19-A B-19-C B-21-B Plant linesC-4 C-5 121-1-B Comparison of 121-4-B CT content R 1 OH Leucoanthocyanidin HO O Genetic support for R 1=R2=H, leucopelargonidin R 2 R 1=OH, R2=H, leucocyanidin OH R 1=R2=OH, leucodelphinidin new pathway to OH OH ANS LAR R condensed R 1 1 OH OH HO O HO O tannins via BAN + R R 2 2 OH OH BAN OH OH Anthocyanidin: (ANR) 2,3-trans-2R,3S-flavan-3-ol R =R =H, pelargonidin 1 2 R R =OH, R =H, cyanidin 1 1 2 OH R 1=R2=OH, delphinidin HO O 2 R 2 4 3 OH 3GT OH 2,3-cis-2R,3R-flavan-3-ol R 1=R2=H, (-)-epiafzelechin R 1=OH, R2=H, (-)-epicatechin R 1=R2=OH, (-)epigallocatechin Anthocyanins R1 Col tt18 ban OH HO O R 2 R n OH 1 OH OH HO O R 2 OH OH Condensed tannins Species and tissue ANR enzyme activity (pmol/min/mg protein) Lotus corniculatus Leaf 721 Desmodium uncinatum Leaf 563 Flower 342 Pod 122 Grape Skin 143 Barley Grain 33* Alfalfa Leaf No reaction Data of Deyu Xie Moving tannins into alfalfa Provision of anthocyanin substrate? Need for LAR? Need for transporters, etc? Anthocyanin flower pigments- natural or engineered? WT BAN PAPIxBAN PAP1 Anthocyanin Epicatechin Production of WT --epicatechin BAN --in transgenic tobacco PAP1 ++++++ - leaves PAP1xBAN ++ ++ Redesigning alfalfa – triterpene saponins • Growth inhibitory to poultry • Anti-palatability and possibly toxic to monogastric animals • Anti-insect • Antifungal (avenacins in oats) • Hypocholesterolemic • Anticancer (desert Acacia spp.) Profiling saponins in Medicago spp Intens. x10 6 (a) 22 [Sumner and Huhman, Alfalfa 1.5 21 (cv. Radius) Phytochemistry, 2002] 16 23 1.0 56 8 0.5 4 10 25 LC/MS profiling reveals 35 0.0 0 1020304050Time [min] Intens. more than 30 triterpene x10 6 22 1.50 (b) 21 Alfalfa saponins in M. truncatula 1.25 16 (cv. Kleszczewska) 1.00 6 23 (more complex pattern 5 0.75 8 0.50 10 than alfalfa) 4 25 0.25 35 0.00 0 10 20 30 40 50 Time [min] Intens. x10 6 21 (c) 22 Medicago truncatula CO2H 1.25 16 HO 27 (Jemalong a17) 1.00 15 23 25 26 0.75 30 4 10 24 31 HO 29 0.50 9 CO2H 1 5 0.25 MedicagenicAcid 0.00 0 1020304050Time [min] Saponin aglycones from Medicago truncatula 30 29 Medicagenic Acid Soyasapogenol B 20 mw = 502 19 21 mw = 458 12 18 22 11 13 17 OH 25 26 CO H 14 16 28 2 15 HO 1 9 2 10 8 E 3 7 27 4 5 6 C HO D COOR HO 24 CO H HO 2 CH OH 23 2 2 A B R1O HOH2C Bayogenin mw = 488 O COOR2 R1O HO HOH2C CH2OH Hederagenin Soyasapogenol E mw = 472 mw = 456 Early steps in the biosynthesis of triterpenes and sterols in plants PPO Sesquiterpenes Mevalonic acid FPP Squalene synthase (SS) Squalene Squalene epoxidase (SE) O 2,3-Oxidosqualene β-Amyrin synthase (AS) 30 29 19 20 21 12 13 18 22 11 25 26 17 O 1 9 14 28 2 16 10 8 15 3 5 4 27 HO 7 HO Cycloartenol 6 β-Amyrin 24 23 Time post-elicitation (hr) 700 600 500 SS 01 2 4 8 12 24 48 400 300 SS 200 100 0 SS 0 1020304050 700 600 500 400 SE2 300 SE2 SE2 200 ) 100 0 % ( 0 1020304050 l e 3000 v 2500 e l βAS βAS 2000 A 1500 βAS N 1000 R 500 m 0 0 1020304050 e v i PAL t 180 a l 150 PAL e 120 R 90 PAL 60 30 CHS 0 0 1020304050 120 90 rRNA 60 CHS CHS 30 0 Differential responsivenes of 0 1020304050 triterpene and phenylpropanoid Time post-elicitation (hr) biosynthesis to MeJA in M.
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    Supplementary Materials: Natural Products as Chemopreventive Agents by Potential Inhibition of the Kinase Domain in ErBb Receptors Maria Olivero-Acosta, Wilson Maldonado-Rojas and Jesus Olivero-Verbel Table S1. Protein characterization of human HER Receptor structures downloaded from PDB database. Recept PDB resid Resolut Name Chain Ligand Method or Type Code ues ion Epidermal 1,2,3,4-tetrahydrogen X-ray HER 1 2ITW growth factor A 327 2.88 staurosporine diffraction receptor 2-{2-[4-({5-chloro-6-[3-(trifl Receptor uoromethyl)phenoxy]pyri tyrosine-prot X-ray HER 2 3PP0 A, B 338 din-3-yl}amino)-5h-pyrrolo 2.25 ein kinase diffraction [3,2-d]pyrimidin-5-yl]etho erbb-2 xy}ethanol Receptor tyrosine-prot Phosphoaminophosphonic X-ray HER 3 3LMG A, B 344 2.8 ein kinase acid-adenylate ester diffraction erbb-3 Receptor N-{3-chloro-4-[(3-fluoroben tyrosine-prot zyl)oxy]phenyl}-6-ethylthi X-ray HER 4 2R4B A, B 321 2.4 ein kinase eno[3,2-d]pyrimidin-4-ami diffraction erbb-4 ne Table S2. Results of Multiple Alignment of Sequence Identity (%ID) Performed by SYBYL X-2.0 for Four HER Receptors. Human Her PDB CODE 2ITW 2R4B 3LMG 3PP0 2ITW (HER1) 100.0 80.3 65.9 82.7 2R4B (HER4) 80.3 100 71.7 80.9 3LMG (HER3) 65.9 71.7 100 67.4 3PP0 (HER2) 82.7 80.9 67.4 100 Table S3. Multiple alignment of spatial coordinates for HER receptor pairs (by RMSD) using SYBYL X-2.0. Human Her PDB CODE 2ITW 2R4B 3LMG 3PP0 2ITW (HER1) 0 4.378 4.162 5.682 2R4B (HER4) 4.378 0 2.958 3.31 3LMG (HER3) 4.162 2.958 0 3.656 3PP0 (HER2) 5.682 3.31 3.656 0 Figure S1.
  • Glyceollin) in Soybeans and Pullulan from Sucrose

    Glyceollin) in Soybeans and Pullulan from Sucrose

    South Dakota State University Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange Electronic Theses and Dissertations 2020 Developing Microbial Based Process to Produce High Value Natural Antimicrobial (Glyceollin) in Soybeans and Pullulan from Sucrose Andrea Zavadil South Dakota State University Follow this and additional works at: https://openprairie.sdstate.edu/etd Part of the Agronomy and Crop Sciences Commons, Environmental Microbiology and Microbial Ecology Commons, and the Plant Biology Commons Recommended Citation Zavadil, Andrea, "Developing Microbial Based Process to Produce High Value Natural Antimicrobial (Glyceollin) in Soybeans and Pullulan from Sucrose" (2020). Electronic Theses and Dissertations. 5002. https://openprairie.sdstate.edu/etd/5002 This Thesis - Open Access is brought to you for free and open access by Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange. For more information, please contact [email protected]. DEVELOPING MICROBIAL BASED PROCESS TO PRODUCE HIGH VALUE NATURAL ANTIMICROBIAL (GLYCEOLLIN) IN SOYBEANS AND PULLULAN FROM SUCROSE BY ANDREA ZAVADIL A thesis submitted in partial fulfillment of the requirements for the Master of Science Major in Biological Sciences Specialization in Microbiology South Dakota State University 2020 ii THESIS ACCEPTANCE PAGE Andrea Zavadil This thesis is approved as a creditable and independent investigation by a candidate for the master’s degree and is acceptable for meeting the thesis requirements for this degree. Acceptance of this does not imply that the conclusions reached by the candidate are necessarily the conclusions of the major department.
  • Genetic Regulation of the Elicitation of Glyceollin Biosynthesis in Soybean

    Genetic Regulation of the Elicitation of Glyceollin Biosynthesis in Soybean

    Graduate Theses, Dissertations, and Problem Reports 2019 GENETIC REGULATION OF THE ELICITATION OF GLYCEOLLIN BIOSYNTHESIS IN SOYBEAN Md. Asraful Jahan West Virginia University, [email protected] Follow this and additional works at: https://researchrepository.wvu.edu/etd Part of the Agricultural Science Commons, Genetics Commons, Molecular Genetics Commons, Plant Breeding and Genetics Commons, and the Plant Pathology Commons Recommended Citation Jahan, Md. Asraful, "GENETIC REGULATION OF THE ELICITATION OF GLYCEOLLIN BIOSYNTHESIS IN SOYBEAN" (2019). Graduate Theses, Dissertations, and Problem Reports. 3782. https://researchrepository.wvu.edu/etd/3782 This Dissertation is protected by copyright and/or related rights. It has been brought to you by the The Research Repository @ WVU with permission from the rights-holder(s). You are free to use this Dissertation in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you must obtain permission from the rights-holder(s) directly, unless additional rights are indicated by a Creative Commons license in the record and/ or on the work itself. This Dissertation has been accepted for inclusion in WVU Graduate Theses, Dissertations, and Problem Reports collection by an authorized administrator of The Research Repository @ WVU. For more information, please contact [email protected]. Genetic Regulation of the Elicitation of Glyceollin Biosynthesis in Soybean Md. Asraful Jahan Dissertation submitted to the Davis College of Agriculture, Natural Resources and Design at West Virginia University in partial fulfillment of requirements for the degree of Doctor of Philosophy in Genetics and Developmental Biology Nikola Kovinich, Ph.D., Committee Chair Daniel G.
  • Introduction (Pdf)

    Introduction (Pdf)

    Dictionary of Natural Products on CD-ROM This introduction screen gives access to (a) a general introduction to the scope and content of DNP on CD-ROM, followed by (b) an extensive review of the different types of natural product and the way in which they are organised and categorised in DNP. You may access the section of your choice by clicking on the appropriate line below, or you may scroll through the text forwards or backwards from any point. Introduction to the DNP database page 3 Data presentation and organisation 3 Derivatives and variants 3 Chemical names and synonyms 4 CAS Registry Numbers 6 Diagrams 7 Stereochemical conventions 7 Molecular formula and molecular weight 8 Source 9 Importance/use 9 Type of Compound 9 Physical Data 9 Hazard and toxicity information 10 Bibliographic References 11 Journal abbreviations 12 Entry under review 12 Description of Natural Product Structures 13 Aliphatic natural products 15 Semiochemicals 15 Lipids 22 Polyketides 29 Carbohydrates 35 Oxygen heterocycles 44 Simple aromatic natural products 45 Benzofuranoids 48 Benzopyranoids 49 1 Flavonoids page 51 Tannins 60 Lignans 64 Polycyclic aromatic natural products 68 Terpenoids 72 Monoterpenoids 73 Sesquiterpenoids 77 Diterpenoids 101 Sesterterpenoids 118 Triterpenoids 121 Tetraterpenoids 131 Miscellaneous terpenoids 133 Meroterpenoids 133 Steroids 135 The sterols 140 Aminoacids and peptides 148 Aminoacids 148 Peptides 150 β-Lactams 151 Glycopeptides 153 Alkaloids 154 Alkaloids derived from ornithine 154 Alkaloids derived from lysine 156 Alkaloids