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Title: Biosynthesis of mangostin. Part 1: The origin of the xanthone skeleton
Authors: Bennett, G.J. 
Lee, H.-H. 
Das, N.P.
Issue Date: 1990
Citation: Bennett, G.J.,Lee, H.-H.,Das, N.P. (1990). Biosynthesis of mangostin. Part 1: The origin of the xanthone skeleton. Journal of the Chemical Society, Perkin Transactions 1 (10) : 2671-2676. ScholarBank@NUS Repository.
Abstract: The biosynthesis of mangostin (3) has been studied by wick-feeding of 14C- and 13C-labelled precursors to young Garcinia mangostana plants. Radioactive mangostin was isolated as 3,6-di-O- methylmangostin (4), which was subsequently degraded to phloroglucinol and isovaleric acid to aid location of the label. Although results from feeding of 14C-labelled precursors suggested two alternative malonate-shikimate routes to compound (3), experiments with 13C-labelled compounds clearly demonstrated that mangostin (3) originates from a C6C 1 unit (benzoate) and three C2 units (malonates). [1,2,3-13C3]malonic acid was incorporated solely into ring A of compound (4) and two different arrangements of C2 units in compounds (17a and b) were evident, indicating that mangostin (3) derives via ring closure of a symmetrical intermediate (18).
Source Title: Journal of the Chemical Society, Perkin Transactions 1
ISSN: 14727781
Appears in Collections:Staff Publications

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