1 / 20

prof. dr. Samo Kreft

prof. dr. Samo Kreft. Rastlinska biokemija TERPENI. terpeni = terpenoidi = izoprenoidi. C 5 hemiterpen i C 10 monoterpen i C 15 ses kv iterpen i C 20 diterpen i C 25 sesterterpen i C 30 triterpen i C 40 k arotenoid i C n (n>40) pol i i z oprenoid i. terpeni. C 5 hemiterpen i

filia
Download Presentation

prof. dr. Samo Kreft

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. prof. dr. Samo Kreft Rastlinska biokemija TERPENI

  2. terpeni = terpenoidi = izoprenoidi • C5 hemiterpeni • C10 monoterpeni • C15 seskviterpeni • C20 diterpeni • C25 sesterterpeni • C30 triterpeni • C40karotenoidi • Cn (n>40)poliizoprenoidi

  3. terpeni • C5 hemiterpeni • C10 monoterpeni • C15 seskviterpeni • C20 diterpeni • C25 sesterterpeni • C30 triterpeni • C40karotenoidi • Cn (n>40)poliizoprenoidi • lipofilne snovi • sinteza tudi pri živalih • nekaj neobhodnih za življenje • membranski steroli • karoteni • stranske verige na nekaterih spojinah • ubikinonu • klorofilu • sekundarni metaboliti • eterična olja • smole • gume

  4. terpeni: gradnja osnovnega skeleta • nastanejo s polimerizacijo izopentenilpirofosfata (IPP), sledi ciklizacija. • IPP se sintetizira po dveh različnih poteh DXP pot DOXP (1-deoksi-ksiluloze 5P), MEP (2-methyl-erythritol 4P) odkrita leta 1993 (plastidi) Cytokinins Abscisic acid Carotenoids Phytol Plastoquinone Tocopherols Mevalonatnapot znana že 40 let (cytosol and ER) Brassinosteroids Phytosterols Phytoalexins Prenyl groups Ubiquinone (mitos)

  5. CH2COOH | CH3-COH | CH2 | C=O | S-CoA CH2COOH | CH3-COH | CH2 | CH2OH HMG-CoA synthase HMG-CoA reductase CH3 | C=O | S-CoA 3 x mevalonate NADPH simvastatin (mevinolin) acetyl CoA CO2 ATP hydroxymethyl glutaryl CoA mevalonate kinase/ decarboxylase CH2 || CH3-C | CH2 | CH2OPP IPP Mevalonatna pot 5 Enzymes in cytosol and ER

  6. HMG CoA sintaza • večgenska družina • 2 gena pri Arabidopsis • Izraža se v vseh rastlinskih organih • največ v zgodnji stopnji razvoja • Down-regulacija pri stresu • ABA, osmotski stres, dehidratacija • Up-regulacijapri ranah, MeJA in SA • sterolizapopravila in fitoaleksini

  7. HMG CoA reduktaza (HMGR) • več izovorm HMG CoA reduktaze • HMGRkontrolni encim pri živalih in kvasovkah • HMGR aktivnost korelira s producijo lateksa: produkcija lateksa HMGR drugi encimi Jan-Mar VisokaVisoka Visoka June-July Nizka Nizka Visoka

  8. Regulacija • HMGR required in early fruit development in tomato but not during ripening • Membrane sterols and not carotenoids • HMGR induced by wounding and pathogens • Potato HMGR 1 induced by wounding - sterols • HMGR 2 & 3 induced by elicitors - sesquiterpene phytoalexins • Co-ordinated regulation of HMGS and HMGR • wounding • pathogens • germination

  9. CH3 | C=O | CHOH | HCOH | CH2OP CH3 | C=O | COOH CHO | CHOH | CH2OP DXP sintaza 1-deoksi- ksilulose 5P + Piruvat Gliceraldehid 3P DXP izomero- reduktaza CH2OH | CH2-C-OH | HCOH | CH2OP NADPH 2-metil-eritritol 4P DXP/MEP pot encimi v plastidih CH3 || C-CH3 | CH2 | CH2OPP izopentenil pp MEP citidilil transferaza CDP-ME kinaza MECDP sintaza

  10. 13C-Labeling patterns of isopentenyl diphosphate (IPP) from [1-13C]glucose formed via a), the acetate/MVA pathway (white circles); b), the DOXP/MEP pathway (black circles).

  11. terpeni: gradnja osnovnega skeleta OPP OPP OPP dimetilalil PP OPP OPP IPP PPi izopentenil PP DMAPP GeranilPP + • izopentenil PP izomeraza • vsi drugi izoprenoidi • nastanejo s kondenzacijo IPP in DMAPP • preniltransferaza

  12. terpeni: gradnja osnovnega skeleta Prenyln Cytokinins Substituted tRNA bases Isopentenyl pyrophosphate (IPP) Cyclase Geranyl PP (C10; GPP) Monoterpenes Coupling Cyclase Squalene C30 Sterols Triterpenes Farnesyl PP (C15; FPP) Sesquiterpenes Cyclase Geranylgeranyl PP (C20; GGPP) Phytol Gibberellins Diterpenes Coupl- ing PT Phytoene C40 Carotenoids C45-50 Polyterpenes (C30,000) Rubber, Gutta percha PT PT Abscisic acid Sidechains of PQ & UQ

  13. terpeni: gradnja osnovnega skeleta OPP OPP phytoene • Head-to-head condensation • Squalene synthase for sterols (C30), phytoene synthase for carotenoids (C40)

  14. terpeni: ciklizacija

  15. povečanje aktivnosti fitoensintaze (transgena rastlina: konstitutivna ekspresija fitoensintaze s 35S promotorem) Pyruvate + G3P DXP IPP + DMAPP GGPP Phytoene -carotene Lycopene DXPS (CLA1) DXR GAs Phytol chlorophylls PSY PDS Carotenoids

  16. Golden rice • SE Asia - vitamin A deficiency in 70% of under 5s • Rice endosperm cannot synthesis -carotene • Only enzymes up to GGPP • Introduction of PYS • Carotene desaturase (PDS and -carotene desaturase activity) • Lycopene -cyclase • Golden rice producing -carotene • Ye at al 2000 WT Golden rice

  17. eterično olje poprove mete mentofuran menton limonen

  18. eterično olje poprove mete • Monoterpene synthesis in mint in glandular trichomes • Major component menthol, but also menthofuran • Introduction of sense DXR • Increase of up to 50% essential oil • Antisense menthofuran synthase • Decrease of 50% menthanofuran Plant Oil weight Menthol (%) Menthofuran (mg/g FW) WT 1.8 6.9 16.8 DXR6 2.6 12.7 15.7 MSF1 1.7 23.2 2.5 Mahmoud and Croteau 2001

  19. - eterična olja • stomahiki, karminativ - posp. prebavo, proti napenjanju (KAMILICA, KUMINA, PELIN, KOLMEŽ) • antiseptiki - razkužuje kožo in sluznice (ŽAJBELJ, TIMIJAN, EUKALIPTUS, KLINČKI) • rubefaciensi - dražijo kožo (BOR, ROŽMARIN, TIMIJAN) • ekspektoransi - olajšujejo kašelj (JANEŽ, KOROMAČ, EUKALIPTUS,TIMIJAN) • diuretik - posp. izl. seča (BRIN, PETERŠILJ) • sedativi - pomirjevalo (BALDRIAN, HMELJ, MELISA, SIVKA)

  20. pravi pelin Artemisia absinthium

More Related