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Literature summary for 1.14.14.131 extracted from

  • Lau, W.; Sattely, E.
    Six enzymes from mayapple that complete the biosynthetic pathway to the etoposide aglycone (2015), Science, 349, 1224-1228.
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
synthesis recombinant coexpression of the genes involved in the podophyllotoxin pathway permits to reconstitute the pathway to (-)-4'-demethylepipodophyllotoxin (the etoposide aglycone), a naturally occurring lignan that is the immediate precursor of etoposide and, unlike podophyllotoxin, a potent topoisomerase inhibitor, for production of the etoposide aglycone in tobacco and circumvent the need for cultivation of mayapple and semisynthetic epimerization and demethylation of podophyllotoxin Sinopodophyllum hexandrum

Cloned(Commentary)

Cloned (Comment) Organism
gene Phex524 or CYP71CU1, expression analysis by qRT-PCR analysis, transcriptome mining to identify biosynthetic genes in the podophyllotoxin pathway, Agrobacterium-mediated functional transient expression in Nicotiana benthamiana Sinopodophyllum hexandrum

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(-)-5'-demethoxyyatein + [reduced NADPH-hemoprotein reductase] + O2 Sinopodophyllum hexandrum
-
(-)-5'-demethylyatein + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Organism

Organism UniProt Comment Textmining
Sinopodophyllum hexandrum A0A0N9HTU1 or Sinopodophyllum hexandrum, gene Phex524 or CYP71CU1
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(-)-5'-demethoxyyatein + [reduced NADPH-hemoprotein reductase] + O2
-
Sinopodophyllum hexandrum (-)-5'-demethylyatein + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

General Information

General Information Comment Organism
metabolism the enzyme is involved in the biosynthesis of (-)-4'-demethylepipodophyllotoxin (the etoposide aglycone), a naturally occurring lignan that is the immediate precursor of etoposide and, unlike podophyllotoxin, a potent topoisomerase inhibitor. Biosynthetic pathway of (-)-podophyllotoxin, overview Sinopodophyllum hexandrum