2018
DOI: 10.1111/tpj.14111
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Abstract: The important anticancer drugs, vinblastine, vincristine and analogs, are composed of the monoterpenoid indole alkaloids (MIAs), catharanthine and vindoline, found uniquely in the medicinal plant, Catharanthus roseus. While 26 genes involved in the assembly of these two MIAs are known, two key reactions have eluded characterization to complete the documentation of the vinblastine pathway in this plant species. The assembly of these dimeric MIAs requires O-acetylstemmadenine oxidase (ASO) and a dual function ge… Show more

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Cited by 95 publications
(89 citation statements)
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“…The substrate specificity of T19H for (−)‐vincadifformine and of V19H for (+)‐vincadifformine was used to determine which enantiomer of vincadifformine was produced by hydrolases HL3 and HL4. As shown previously (Qu et al ., ), vincadifformine was formed when O ‐acetylstemmadenine was incubated with ASO, GS and HL3 in the presence of NADPH (Figure a). Incubation of this reaction product with T19H‐enriched yeast microsomes and NADPH did not result in the formation of minovincinine (Figure c), while the same assay with V19H yeast microsomes generated minovincinine (Figure b).…”
Section: Resultsmentioning
confidence: 96%
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“…The substrate specificity of T19H for (−)‐vincadifformine and of V19H for (+)‐vincadifformine was used to determine which enantiomer of vincadifformine was produced by hydrolases HL3 and HL4. As shown previously (Qu et al ., ), vincadifformine was formed when O ‐acetylstemmadenine was incubated with ASO, GS and HL3 in the presence of NADPH (Figure a). Incubation of this reaction product with T19H‐enriched yeast microsomes and NADPH did not result in the formation of minovincinine (Figure c), while the same assay with V19H yeast microsomes generated minovincinine (Figure b).…”
Section: Resultsmentioning
confidence: 96%
“…The formation of tabersonine, catharanthine and vincadifformine involves separate conversions of a common reactive intermediate derived from O-acetylstemmadenine by the action of O-acetylstemmadenine oxidase (ASO) and GS ( Figure 2) (Qu et al, 2019). Four separate hydrolases (HL1-4) that convert the reactive intermediate to catharanthine (HL1), to tabersonine (HL2) or to vincadifformine (HL3 or HL4) have been identified (Qu et al, 2018b;Qu et al, 2019). The involvement of separate hydrolases in the biosynthesis of tabersonine and vincadifformine clearly indicates that vincadifformine formation branches off prior to the formation of tabersonine.…”
Section: Recombinant Mat and Tat Catalyze Enantiomer-specific O-acetymentioning
confidence: 99%
“…We hypothesized how the (-)-coronardine enantiomer might form in this system. (-)-Catharanthine could be formed from dehydrosecodine (9), analogous to (+)-catharanthine (4) biosynthesis in C. roseus (e.g. Fig.…”
Section: Figmentioning
confidence: 99%
“…Alternatively, binding of secodine (10) to TiDPAS1/2 may 30 provide an enantiomerically enriched cyclization product. However, formation of (-)vincadifformine (11) is not dependent on the presence of a dedicated cyclase enzyme (9).…”
mentioning
confidence: 97%
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