Amino Acids:OrnithineLysineTyrosineTryptophanPurineStarting materials:Amino acids and nucleic acidsNMeHNOHOHHNNNNOOCH3CH3H3CNMeOCO2MeOpseudopelletierinenicotineNNMeHcaffeineergotONCH3HOHOHHmorphineCO2NH3OHNHNH3CO2NNNNNH2OOHOHOP-OO-ONH3CO2H3NCO2H3NNH3NMeOcocaineornithinepurinetyrosinelysinetryptophan5.451 F2005Alkaloid Biosynthesis:Nitrogen containing compounds(fungus)rebeccamycinstaurosporine5.451 F2005Alkaloid Biosynthesis:Purine Derived Products: CaffeineTFigure removed due to copyright reasons. Please see Figure 4 in Trends Plant Sci 6 (2001): 407.5.451 F2005Alkaloid Biosynthesis:Purine Derived Products: CaffeineGenetically engineered decaf coffee70% reduction in caffeine content by using RNAi of theobromine synthaseotherwise normal phenotypeNature (2003) 423, 823Recently discovered natural variant deficient in caffeine synthase Nature (2004) 429, 826.Promoter of the 3 methyl transferases recently discoveredJ. Biotech. (2005) 119, 20-25.pyrrolizidine5.451 F2005Alkaloid Biosynthesis:Ornithine and Lysine Derived ProductsNHhomospermidine(via 2 putrescines)tropanesNMenicotineNNMeHquinolizidinesNindolizidinesNNH2H2Nputrescine (via ornithine)2 acetatesNH2H2Nputrescine (via ornithine)nicotinic acidNMepseudopelletierinecadaverine (via lysine)2 acetates2 cadaverines pipecolic acid (via lysine)1 acetatepyrrolidines nicotineNNMeHNH5.451 F2005 Alkaloid Biosynthesis:Ornithine Derived ProductsNCO2HNOHONHNHHNMeHNMeHNMeH-H+H+NADP+CO2nicotinic acidB3 (niacin)pyrrolizidine5.451 F2005 Alkaloid Biosynthesis:Ornithine Derived ProductsNHpyrrolizidine5.451 F2005 Alkaloid Biosynthesis:Ornithine Derived ProductsNHPNAS (1999) 96, p. 14779Origin of a secondary metabolic pathway?Found only in angiospermsNHH2NNH2H2NNH2NHH2NNH2+NH2ENHH2NNH2+HNENH2E=elF5AHNENH2OHhypusinedeoxyhypusinespermidinelysine of transcription factorputrescinehomosperrmidineHS synthaseDH synthasedeoxyhypusinesynthasepiperidines ornithine5.451 F2005 Alkaloid Biosynthesis:Lysine Derived ProductsNHH3N CO2NH2H3N CO2NH2lysinequinolizidines5.451 F2005 Alkaloid Biosynthesis:Lysine Derived ProductsNNH2N NH2H2N CHONHNHNHNHHNHCHOHNH2NHCHOHCHOCHOHNH2H2NNHH2NNNH2H2NNH2NHOHC NH2OHCNHCHONH2Nindolizidines5.451 F2005 Alkaloid Biosynthesis:Lysine Derived ProductsNH3N NH2NHNCO2H2N HCO2OCO2HNHOOSCoAHHOOOOH OMeOOONHOMeOOOOH HOMepipecolic acidacetatepolyketide/peptiderapamycincyclohexylCoAshikimicacid5.451 F2005 Alkaloid Biosynthesis:Ornithine Derived ProductsSource of alkaloidsarthropod eats plant;or ant or symbiontof ant makes alkaloidvertebrate (frog) eats antafter injestion, can be derivatized by frog to make more poisonousSee Figure 1 in PNAS 100 (2003): 11092.alkaloids found in ants and frogsSee Figure 1 in PNAS 101 (2004): 8045.Figure removed due to copyright reasons.Figure removed due to copyright reasons.5.451 F2005 Alkaloid Biosynthesis:Ornithine Derived ProductsChemical DefenseFigures removed due to copyright reasons.5.451 F2005 Alkaloid Biosynthesis:Ornithine Derived ProductsRemoved due to copyright reasons.pyrrolizidine5.451 F2005 Alkaloid Biosynthesis:Ornithine Derived ProductsOutwitting the Chemical Defense- Detoxification by oxidationNHNHCHOOdetoxificationFigure removed due to copyright reasons. Please see Figure 1 in PNAS 99 (2002):