New Flavanol and Cycloartane Glucosides from Landoltia punctata

Chemical investigation on the constituents of Landoltia punctata led to the isolation and identification of 17 compounds, four of which were new and identified as (3β,24S)-9,19-cycloartane-3,22,24,25-tetraol 3-O-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→6)]-β-d-glucopyranoside (1), (3β,24S)-9,19-cycloartane-3,24,25-triol 3-O-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→6)]-β-d-glucopyranoside (2), 3,4'-dihydroxy-7,3'-dimethoxyflavan-5-O-β-d-glucopyranoside (3) and 3,4'-dihydroxy-4,7,3'-trimethoxyflavan-5-O-β-d-glucopyranoside (4). Their structures were elucidated by spectroscopic, chemical, and biochemical methods. Thus, cycloartane triterpenoids were discovered in the Lemnaceae family for the first time. Compound 3 showed antioxidant capacity in the positively charged 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid radical (ABTS(+•)) and superoxide anion radical scavenging assays.