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Unnatural Spirocyclic Oxindole Alkaloids Biosynthesis in Uncaria Guianensis

Unnatural Spirocyclic Oxindole Alkaloids Biosynthesis in Uncaria Guianensis

Adriana A Lopes, Bianca Chioca, Bruno Musquiari, Eduardo J Crevelin, Suzelei de C França, Maria Fatima das G Fernandes da Silva, Ana Maria S Pereira

Sci Rep. 2019 Aug 5;9(1):11349.

PMID: 31383908

Abstract:

Spiro-oxindole scaffolds have been studied due to their promising therapeutic potential. In the Amazon rainforest there are two important Uncaria species known as "cat's claw", which biosynthesize spirocyclic oxindole alkaloids; Uncaria tomentosa (Willd. ex Schult.) DC. and Uncaria guianensis (Aublet) Gmell. We carried out a precursor-directed biosynthesis approach with U. guianensis and 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 (3b-7-methyl-isomitraphylline and 3c-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 (1), rhynchophylline (2), isomitraphylline (3) and isorhynchophylline (4) was also investigated using 13C-precursors (1-13C-D-glucose, 2-13C-tryptophan, 1-13C-DL-glyceraldehyde, and methyl-13C-D-methionine).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4963013	Isomitraphylline		4963-01-3	Price

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