Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron.

MARÍA DEL MILAGRO BRAVETTI; RAQUEL V. VICO; MARIA C. CARPINELLA; CARLOS G. FERRAYOLI; SARA M. PALACIOS; MARÍA DEL MILAGRO BRAVETTI; RAQUEL V. VICO; MARIA C. CARPINELLA; CARLOS G. FERRAYOLI; SARA M. PALACIOS

PHYTOCHEMISTRY

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2017 vol. 138 p. 145 - 151

0031-9422

Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanussativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate],charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B[(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configurationwere established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination(ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum(monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum(ECg50 = 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulatingthe root growth of P. miliaceum seedlings, with an ECr50 of 1.0 mM. Charuol A inhibited the germination of R. sativus,while its seedling development was also affected by all three compounds with different effectiveness. Charuol A wasalso highly effective in the 0.09?0.30 mM range against other test species such as Lactuca sativa, Eruca sativa, Alliumampeloprasum and Secale cereale