Phenylpropanoids from the Immature Fruits of Black Nightshade (Solanum nigrum L.)

Black nightshade (Solanum nigrum L.) has been traditionally used as indigenous Chinese medicine. Phytochemical investigations of the immature fruits of S. nigrum have been carried out and nine phenylpropanoids (1-9) were obtained. Their structures were elucidated on the basis of spectroscopic and chemical methods, including MS, 1H and 13C-NMR. They were identified as (7S, 8R)-4-[3-hydroxymethyl-5-(3- hydroxypropyl)-2,3-dihydrobenzofuran-2-yl]-2-methoxyphenol (1), (7S, 8R)- dihydrodehydroconifery alcohol (2), massonianoside A (3), butane-2,3-diol 2-O- (6-O-caffeoyl)-β-D-glucopyraniside (4), 4-[(6-O-(E)-caffeoyl)-β-D-glucopyranosyl] vanillic acid (5), (+)-isolariciresinol (6), trans-cinnamic acid (7), ferulic acid (8), and 4-hydroxy cinnamic acid (9). This study enriched the chemical constituents of black nightshade.