New isoflavone derivative and other flavonoids from the resin of Amburana cearensis

Abstract

A investigação fitoquímica da resina de Amburana cearensis A. C. Smith permitiu o isolamento de um novo composto: 3',4'-dimetóxi-1'-(7-metóxi-4-oxo-4H-cromen-3-il) benzo-2',5'-quinona (1), juntamente com seis compostos conhecidos e identificados como: 4,2',4'-triidroxichalcona (2), 7,8,3',4'-tetrametoxiisoflavona (3), 4,2',4'-triidroxi-3metoxichalcona (4), 3,4,5-trimetoxicinamaldeido (5), 3',4'-dimetoxi-7-hidroxiisoflavona (6) e 6,7,4'-trimetoxi-3'-hidroxiisoflavona (7). As estruturas foram estabelecidas com base na análise dos dados espectrométricos de: IV, EI-EM, HR-ESI-EM e RMN incluindo experimentos 2D. Phytochemical investigation of the resin of Amburana cearensis A. C. Smith allowed the isolation of a new compound: 3',4'-dimethoxy-1'-(7-methoxy-4-oxo-4Hcromen-3-yl)benzo-2',5'-quinone (1), together with six known compounds identified as: 4,2',4'-trihydroxychalcone (2), 7,8,3',4'-tetramethoxyisoflavone (3), 4,2',4'-trihydroxy-3methoxychalcone (4), 3,4,5-trimethoxycinnamaldehyde (5), 3',4'-dimethoxy-7-hydroxyisoflavone (6) and 6,7,4'-trimethoxy-3'-hydroxyisoflavone (7). The structures were established from the IR, HR-ESI-MS and NMR spectral data, including 2D-NMR experiments.

Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes

“…Isoflavonoids are compounds accumulated both constitutively and/or in response to a range of environmental stress conditions and their composition may vary due to agri-environmental factors. Although the presence of isoflavonoids has already been known in some of our samples (such as in bark 32 and resin 33 of A. cearensis, seeds of C. mucunoides 34 and C. pubescens 35 and bark of C. argentea 36 ), the parts investigated or compound found were different from those presented here. This article brings the first evidence of the wileyonlinelibrary.com/jsfa presence of selected isoflavones and coumestrol in several species such as Aeschynomene americana, Andira macrothyrsa, Desmodium ovalifolium and Leucaena leucocephala.…”

Antioxidant, Anti-inflammatory and Cytotoxic Activity of Schinus terebinthifolia Fruit and Isolation of a New Immunomodulatory Polyphenolic Compound

“…Their structures were confirmed by comparing our findings with that of previously published research. 15, 21-26 In addition, our research has resulted in a new compound being isolated for the first time from this plant. It is here termed Compound 8.…”

Enantioselective Synthesis of Isoflavanones and Pterocarpans through a RuII‐Catalyzed ATH‐DKR of Isoflavones

“…Selective demethylation [18] of 6 e with AlCl 3 led to the corresponding 2’‐hydroxy‐isoflavone 6 j in 68 % yield, while a bromination of 6 c with NBS resulted in the 2’‐bromo‐isoflavone 6 k in 89 % yield. It is worth mentioning that six of the synthesized isoflavones are natural products ( 6 a , [19] 6 c , [20] 6 e , [21] 6 f , [22] 6 h , [23] 6 j [24] ).…”