In the figures below, observe the biosynthesis of scopolamine and its intermediates. THE scopolamine is formed by the fusion of two biosynthetic pathways. One derived from L-ornithine and the other from L-phenylalanine. In the bold rectangles are the respective key enzymes that catalyze each of the biosynthesis steps. Scopolamine is a competitive, non-selective muscarinic receptor antagonist drug acetylcholine receptor antagonist (mACHR) giving rise to important pharmacological effects, such as by example antispasmodic action in the gastrointestinal tract.Answer:1) Does scopolamine belong to which chemical class/subclass of natural products?2) This substance can be extracted from different plant species, such as: Atropa,Duboisia, Hyoscyamus, Mandragora and Datura. What is the botanical family of these species?3) What are the biogenetic origins (biosynthetic pathways) of ornithine and phenylalanine? МРО (N-Legenda: 1. ODC (Ornithine decarboxylase); 2. PMT (Putrescine methyltransferase);methylputrescine oxidase); 5. PYKS (Pyrrolidine ketide synthase); 6. CYP82M3 (Tropinone synthase); 7. TR-1(Tropinone reductase); 8. ArAT (Aromatic amino acid aminotransferase 4); 9. PPAR (Phenylpyruvatereductase); 10. UGT-1 (UDP – glucosyltransferase); 11. LS (Littorine synthase); 12. LM, CYP80F1 (Littorinemutase); 13. HDH (Hyoscyamine dehydrogenase); 14. H6H (Hyoscyamine 6B hydroxylase).Fonte: SCHLESINGER, D. et al. Phytochemistry Letters, 43: 219–225, 2021.CH3CYP82M3CH3PYKSTR-IINOHHON- Methylpyrrolinium cation4-(1-Methyl-2-pyrrolidinyl)-3-oxo-butanoic acidTropinonePseudotropineTR-ICH3ÇH3CH3LittorineLittorineонOHOHMutaseSynthaseTropine.6-Fe-Enzyme(*1)LittorineOHCH3SCOAноPhenylalaninePhenylpyruvate PhenyllactatPhenyllactyl- CoACH3но -Fe —EnzymeCH3HOноCOHHyoscyamine aldehydeCH3CH3CH3онOHH6HH6HHOScopolamine6-OH-HyoscyamineHyoscyamineFigura 2. Scopolamine biosynthesis, starting with the N-methylpyrrolinium cation.Legenda: PYKS = polyketide synthase; CYP82M3 = cytochrome P450 enzyme; TR-I/II = tropinone reductase1/1I; littorine synthase (sequence not known); littorine mutase/monooxygenase (CYP80F1); (* 1) = proposedmechanism of littorine rearrangement; H6H = hyoscyamine 6B-hydroxylase.Fonte: KOHNEN-JOHANNSEN, K. L. & KAYSER, O. Molecules, 24: 796, 2019. NH,H,N.OHL-ornithineC5H12N2O21. ODCNH,H,N°L-ScopolamineC1,H21NO4putrescineC4H12N22. PMTL-phenylalanineCH1NO214 .H6H`NH,OHно8. ArATN-MethylputrescineCSH14N2L- 6-Hydroxyhyoscyamine(Anisodamine)C17H23NO43. MPОphenylpyruvic acid14 .H6H4-MethylaminobutanalCSH11NO9. PPAR4. spontaneousL- HyoscyamineC,,H23NO3CH,13. HDH3-phenyllactic acidC9H10O3N-Methylpyrrolinium5. PYKS|10. UGT1GLUHyoscyamine aldehydeC1,H21NO34-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid12. LM, CYP80F1PhenyllactylglucoseC15H2008+6. CYР82M37. TR-111. LSlittorinetropinoneC3H13NOOHtropineC17H23NO3C3H15NOFigura 1. Main intermediates and genes involved in scopolamine biosynthesis in Solanaceae.

Question

In the figures below, observe the biosynthesis of scopolamine and its intermediates. THE scopolamine is formed by the fusion of two biosynthetic pathways. One derived from L-ornithine and the other from L-phenylalanine. In the bold rectangles are the respective key enzymes that catalyze each of the biosynthesis steps. Scopolamine is a competitive, non-selective muscarinic receptor antagonist drug acetylcholine receptor antagonist (mACHR) giving rise to important pharmacological effects, such as by example antispasmodic action in the gastrointestinal tract.Answer:1) Does scopolamine belong to which chemical class/subclass of natural products?2) This substance can be extracted from different plant species, such as: Atropa,Duboisia, Hyoscyamus, Mandragora and Datura. What is the botanical family of these species?3) What are the biogenetic origins (biosynthetic pathways) of ornithine and phenylalanine? МРО (N-Legenda: 1. ODC (Ornithine decarboxylase); 2. PMT (Putrescine methyltransferase);methylputrescine oxidase); 5. PYKS (Pyrrolidine ketide synthase); 6. CYP82M3 (Tropinone synthase); 7. TR-1(Tropinone reductase); 8. ArAT (Aromatic amino acid aminotransferase 4); 9. PPAR (Phenylpyruvatereductase); 10. UGT-1 (UDP – glucosyltransferase); 11. LS (Littorine synthase); 12. LM, CYP80F1 (Littorinemutase); 13. HDH (Hyoscyamine dehydrogenase); 14. H6H (Hyoscyamine 6B hydroxylase).Fonte: SCHLESINGER, D. et al. Phytochemistry Letters, 43: 219–225, 2021.CH3CYP82M3CH3PYKSTR-IINOHHON- Methylpyrrolinium cation4-(1-Methyl-2-pyrrolidinyl)-3-oxo-butanoic acidTropinonePseudotropineTR-ICH3ÇH3CH3LittorineLittorineонOHOHMutaseSynthaseTropine.6-Fe-Enzyme(*1)LittorineOHCH3SCOAноPhenylalaninePhenylpyruvate > PhenyllactatPhenyllactyl- CoACH3но -Fe —EnzymeCH3HOноCOHHyoscyamine aldehydeCH3CH3CH3онOHH6HH6HHOScopolamine6-OH-HyoscyamineHyoscyamineFigura 2. Scopolamine biosynthesis, starting with the N-methylpyrrolinium cation.Legenda: PYKS = polyketide synthase; CYP82M3 = cytochrome P450 enzyme; TR-I/II = tropinone reductase1/1I; littorine synthase (sequence not known); littorine mutase/monooxygenase (CYP80F1); (* 1) = proposedmechanism of littorine rearrangement; H6H = hyoscyamine 6B-hydroxylase.Fonte: KOHNEN-JOHANNSEN, K. L. & KAYSER, O. Molecules, 24: 796, 2019. NH,H,N.OHL-ornithineC5H12N2O21. ODCNH,H,N°L-ScopolamineC1,H21NO4putrescineC4H12N22. PMTL-phenylalanineCH1NO214 .H6H`NH,OHно8. ArATN-MethylputrescineCSH14N2L- 6-Hydroxyhyoscyamine(Anisodamine)C17H23NO43. MPОphenylpyruvic acid14 .H6H4-MethylaminobutanalCSH11NO9. PPAR4. spontaneousL- HyoscyamineC,,H23NO3CH,13. HDH3-phenyllactic acidC9H10O3N-Methylpyrrolinium5. PYKS|10. UGT1GLUHyoscyamine aldehydeC1,H21NO34-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid12. LM, CYP80F1PhenyllactylglucoseC15H2008+6. CYР82M37. TR-111. LSlittorinetropinoneC3H13NOOHtropineC17H23NO3C3H15NOFigura 1. Main intermediates and genes involved in scopolamine biosynthesis in Solanaceae.

Accepted Answer

Answered: Image /qna-images/answer/0e055ae1-cd49-42d2-be52-bd51dfd1af8a.jpg