Sesquiterpenoids and Phenylpropane Derivatives from Sonchus uliginosus

Abstract

Six new compounds were isolated from the whole plant of Sonchus uliginosus, including three eudesmane-type sesquiterpenoids (1b,6a)-1,6,14-trihydroxyeudesm-3-en-12-oic acid g-lactone (1), (1b,6a)-1,6,14-trihydroxyeudesma-3,11(13)-dien-12-oic acid g-lactone (2), and (1b,6a)-1,6-dihydroxy-14-O-[(4-hydroxyphenyl)acetyl]eudesma-3,11(13)-dien-12-oic acid g-lactone (3), and three phenylpropane derivatives, 4-hydroxy-g,3,5-trimethoxybenzenepropanol (6), g,3,4,5-tetramethoxybenzenepropanol (7), and g,3,4,5-tetramethoxybenzenepropanol acetate (8), together with the two known compounds 4 and 5. The new structures were elucidated by means of spectroscopic methods, such as IR, EI-MS, HR-ESI-MS, 1D-and 2D-NMR, and by comparison of the spectroscopic data with those reported for structurally related compounds.Introduction. -The genus Sonchus, representing 8 species in China, has long been used as folk medicine for the treatment of fever, stasis, and inflammation, as well as for detoxication and mobilization of blood circulation [1]. In some species, eudesmanolides

Natural sesquiterpenoids

“…Six new lactones have been obtained from Sonchus uliginosus. 298 Two are given in Table 2, but the other four had previously been isolated from Sonchus transcarpicus. Their structures were reported in our last review.…”

Sesquiterpene Lactones with Anti-Inflammatory Activity from the Halophyte Sonchus brachyotus DC

“…Compounds 1 and 3 were identified as (1 R , 5 R , 6 R , 7 S , 10 S )-5α,6βH-eudesma-3, 11(13)-dien-12,6α-olide and 1β- O -β- D -glucopyranosyl-(1 R , 5 R , 6 R , 7 S , 10 S )-5α,6βH-eudesma-3, 11(13)-dien-12,6α-olide, respectively, by interpretation of 1D and 2D NMR spectra and comparison with optical rotation values reported in the literature [ 13 , 14 ].…”

Chemical and Biological Investigations of the Roots of Sonchus Oleraceus L. Growing in Egypt

“…Sonchus plants are well-known with their content of sesqueterpene lactones of the eudismanolide 4&5 and guaianolide structures 6 . Other constituents include ionone glycosides 7 , phenyl propanoids 8 , phenolics [flavonoids and coumarins] 9 , in addition to sterols and lignans 10 .…”