Amburosides C-H and 6-O-protocatechuoyl coumarin from Amburana cearensis

Abstract

Seis novos amburosídeos (1-6) e o novo protocatecuato de 6-cumarila (7) foram isolados das sementes e cascas do caule de Amburana cearensis, juntamente com cumarina, 6-hidroxicumarina, isocampferídeo, formononetina, ácido vanílico, amburosídeo A e ácido (E)-o-cumárico. As estruturas químicas dos novos compostos foram elucidadas com base na análise espectral de RMN (COSY, HSQC, HMBC e NOESY) e EM.Six new amburosides (1-6) and a novel 6-coumaryl protocatechuate (7) were isolated from the seeds and trunk bark of Amburana cearensis, together with coumarin, 6-hydroxycoumarin, isokaempferide, formononetin, vanillic acid, amburoside A and (E)-o-coumaric acid. The chemical structures of the new compounds were elucidated by means of NMR (COSY, HSQC, HMBC and NOESY) and HRMS spectral analyses.

Componential Profile and Amylase Inhibiting Activity of Phenolic Compounds fromCalendula officinalisL. Leaves

“…The moiety of 6 has been detected previously in different compounds like glehlinosides from Glehnia littoralis (Euphorbiaceae) [ 27 ], 6′- O -vanilloylsucrose from Saccharum officinarum (Poaceae) [ 28 ], 6′- O -vanilloyicariside B 5 from Baccaurea ramiflora (Euphorbiaceae) [ 29 ], amburoside G from Amburana cearensis (Fabaceae) [ 30 ], saccharumosides from Acer saccharum (Aceraceae) [ 31 ], and 1′- O -galloyl-6′- O -vanilloyl- β - d -glucopyranose from Alchornea trewioides (Euphorbiaceae) [ 32 ]. This is the first case where 6 has been isolated as a separate compound.…”

O-coumaric acid ester, a potential early signaling molecule in Pinus pinea and Pisolithus arhizus symbiosis established in vitro

“…LCÁDADÁMS analysis identified the substance as an ester of o-coumaric acid, a phenolic acid produced by plants and other organisms as secondary metabolite and a common chemical constituent in the plant kingdom (Abdul-Raman & Habib 1989;Vega et al 2008;Ngoc et al 2009;Sellami et al 2009;Canuto et al 2010). Among many effects, phenolic acids exert allelopathy and are implicated in the development of ecological interactions with the adjoining plant and with some rhizospheric organisms (Kefeli et al 2003).…”

o-Coumaric acid from invasive Eupatorium adenophorum is a potent phytotoxin

“…The isolation of o-coumaric acid from E. adenophorum and discovery of its potent phytotoxicity in the present study corroborated our previous speculation. o-Coumaric acid is a common chemical constituent in the plant kingdom (Habib and Abdul Rahman 1988;Vega et al 2008;Ngoc et al 2009;Sellami et al 2009;Canuto et al 2010). Its phytotoxic effects have also been previous described (Chou and Patrick 1976;Aliotta et al 1993;Li et al 1993;.…”