NMR spectral assignments of a new [COC] isoflavone dimer from Andira surinamensis

Abstract

The phytochemical investigation of extracts from the branch wood and branch barks of Andira surinamensis yielded a novel isoflavone dimer, 4'-methoxyisoflavone-(7-O-7'')-3''',4'''-methylenedioxyisoflavone (surinamensin), along with the triterpene lupeol and the known isoflavones 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A), 5,4'-dihydroxy-7-methoxyisoflavone (prunetin), 7,3'-dihydroxy-4'-methoxyisoflavone (calycosin), and 5,7,3'-trihydroxy-4'-methoxyisoflavone (pratensein). The structure of the new isoflavone was elucidated by 1D and 2D homonuclear and heteronuclear NMR spectroscopy and by comparison with published data for closely related compounds.

Isoflavonoids of the Leguminosae

“…Surinamensin (262) is only the second example of an isoavone dimer, and a constituent of branch extracts (wood and bark) of the tropical forest tree, Andira surinamensis. 216 The isoavone subunits, which are O-linked at C-7 of each A-ring, comprise formononetin (7-hydroxy-4 0 -methoxyisoavone) and pseudobaptigenin (7-hydroxy-3 0 ,4 0 -methylenedioxyisoavone). A similarly linked dimer of afrormosin (7-hydroxy-6,4 0 -dimethoxyisoavone) and 7,2 0 -dihydroxy-6,4 0 -dimethoxyiso-avone was reported previously as a constituent of the heartwood of Platymiscium oribundum.…”

Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains

“…The HMBC spectrum revealed a methoxyl proton signal at δ 3.79(s) correlated to the carbon resonance at δ 157.4 (C-4′), and the NOESY spectrum revealed the distance proximity between protons at δ 3.79(s) and at δ 7.02 (d, H-5′). Based on these spectral data and a comparison of the 1 H-NMR and 13 C-NMR data with literature values [ 10 ], compound 2 was characterized as 5,7,3′-trihydroxy-4′-methoxyisoflavone. These results—together with our previous study [ 7 , 8 ] and the study performed by Lee et al [ 6 ]—reveal that genistein was first converted into 3′-hydroxygenistein by the recombinant E. coli expressing B. megaterium tyrosinase, and then the resulting 3′-hydroxygenistein was further transformed by recombinant E. coli expressing S. peucetius O -methyltransferase into 5,7,4′-trihydroxy-3′-methoxyisoflavone or 5,7,3′-trihydroxy-4′-methoxyisoflavone.…”

“…To our knowledge, this is the first report of the bio-production of the two methoxyisoflavones. Although 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone have been isolated from several plant parts, such as the stems of Erycibe expansa [ 14 ] and the branch wood of Andira surinamensis [ 10 ], they are rare in Nature. Development of an easy method for producing the two methoxyisoflavones would open the research field to exploring the bioactivity of these two compounds in the future.…”

Prunetin Relaxed Isolated Rat Aortic Rings by Blocking Calcium Channels

“…Prunetin is found in many plants used for medicines and foods, including pea [ 14 ], peach [ 15 ], oregon cherry [ 16 ], skimmed cheese, whole cheese, cow kefir, goat kefir [ 17 ], Prunus avium [ 10 ], Andira surinamensis [ 18 ], Butea superba [ 19 ], Dalbergia sympathetica [ 20 ], Ficus nervosa [ 21 ], Pterospartum tridentatum [ 22 ], and Pycnanthus angolensis [ 23 ].…”