Unnatural spirocyclic oxindole alkaloids biosynthesis in Uncaria guianensis
摘要:
Spiro-oxindole scaffolds have been studied due to their promising therapeutic potential. In the Amazon rainforest there are two importantspecies known as "cat's claw", which biosynthesize spirocyclic oxindole alkaloids;(Willd. ex Schult.) DC. and(Aublet) Gmell. We carried out a precursor-directed biosynthesis approach withand successfully obtained oxindole alkaloid analogues with molecular mass corresponding to the addition of a methyl or fluorine group on the oxindole ring using tryptamine analogue precursors. Two of these novel oxindole alkaloid analogues (-7-methyl-isomitraphylline and-6-fluoro-isomitraphylline) were isolated and characterized by NMR spectroscopy and ESI-QTOF-MS/MS. Having established a substrate feeding protocol for these plantlets, the biosynthetic route for mitraphylline (), rhynchophylline (), isomitraphylline () and isorhynchophylline () was also investigated usingC-precursors (1-C-D-glucose, 2-C-tryptophan, 1-C-DL-glyceraldehyde, and methyl-C-D-methionine).
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关键词:
OXINDOLES ALKALOIDS UNCARIA RAIN forests MOLECULAR weights NUCLEAR magnetic resonance spectroscopy
DOI:
10.1038/s41598-019-47706-3
年份:
2019
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