New Phenylpropanoid Glycosides from Illicium majus and Their Radical Scavenging Activities

Abstract

Chemical investigation of the ethanol extract of the branch and leaves of Illicium majus resulted in the isolation of four new phenylpropanoid glycosides (1–4) and one new phenolic glycoside (9), along with 13 known ones. Spectroscopic techniques were used to elucidate the structures of the new isolates such as 3‐[(2R,3S)‐7‐hydroxy‐2‐(4‐hydroxy‐3‐methoxyphenyl)‐3‐(hydroxymethyl)‐2,3‐dihydro‐1‐benzofuran‐5‐yl]propyl β‐D‐glucopyranoside (1), [(2R,3S)‐7‐hydroxy‐2‐(4‐hydroxy‐3‐methoxyphenyl)‐5‐(3‐hydroxypropyl)‐2,3‐dihydro‐1‐benzofuran‐3‐yl]methyl 2‐O‐α‐L‐rhamnopyranosyl‐β‐D‐glucopyranoside (2), [(2R,3S)‐7‐hydroxy‐2‐(4‐hydroxy‐3‐methoxyphenyl)‐5‐(3‐hydroxypropyl)‐2,3‐dihydro‐1‐benzofuran‐3‐yl]methyl 2‐O‐α‐L‐rhamnopyranosyl‐β‐D‐xylopyranoside (3), 3‐[(2R,3S)‐3‐({[2‐O‐(4‐O‐acetyl‐α‐L‐rhamnopyranosyl)‐β‐D‐xylopyranosyl]oxy}methyl)‐7‐hydroxy‐2‐(4‐hydroxy‐3‐methoxyphenyl)‐2,3‐dihydro‐1‐benzofuran‐5‐yl]propyl acetate (4), and 4‐(2‐hydroxyethyl)phenyl 3‐O‐β‐D‐glucopyranosyl‐β‐D‐glucopyranoside (9). Free radical scavenging activities of the isolates were elucidated through the DPPH assay method. The most active compounds, 1‐O‐caffeoyl‐β‐D‐glucopyranose (17) and soulieana acid 1 (18), exhibited moderate radical scavenging activities (IC50=37.7±4.4 μM and IC50=97.2±3.4 μM, respectively). The antibacterial activities of the isolates against Staphylococcus aureus and Escherichia coli were also assessed, and no activity was shown at the measured concentration (<32 μg/mL).

Lignans and Flavonoids from Cajanus cajan (L.) Millsp. and Their α‐Glucosidase Inhibitory Activities

“…In addition, the coupling constant between the anomeric and 2′′′ protons was calculated as 7.2, suggesting the glucose configuration was β . Further, compound 3 was hydrolyzed with 10 % HCl and its products were compared with an authentic D‐glucose using thin layer chromatography (TLC), [12] from which a spot shared the same R f value as that of D‐glucose, confirming that the sugar moiety was D‐glucosyl. Based on the above information, compound 3 indicated to be a β‐ D ‐ glucoside of a flavonoid.…”

Profiling of Secondary Metabolites of Optimized Ripe Ajwa Date Pulp (Phoenix dactylifera L.) Using Response Surface Methodology and Artificial Neural Network

“…Thus, compounds 2 – 7 were tentatively identified as hydroxybenzoylhexose, coumaroyl hexose, caffeoylshikimic acid, caffeic acid hexoside, caffeic acid derivatives, and dicaffeoyl shikimic acid, respectively [ 17 , 39 , 40 ]. Among these, coumaroyl hexose (IC 50 value: 37.7 μM), caffeoylshikimic acid (IC 50 value: 2.9 μM), caffeic acid hexoside (IC 50 value: 0.55 μM), and dicaffeoyl shikimic acid (IC 50 value: 0.38 μM) were found to have DPPH-scavenging activity [ 41 , 42 , 43 ]. Additionally, coumaroyl glucoside severely inhibits glycogen phosphorylase, a crucial target for producing antihyperglycemic medicines [ 44 ].…”

Research status of indole-modified natural products

“…Phenylpropanoids are a class of compounds consisting of a benzene ring linked to three straight-chain carbon atoms (C6–C3 groups), including phenylpropylenes and their derivatives with different degrees of oxidation, coumarins, and lignans, which have pharmacological activities such as anti-tumor, 67 anti-bacterial, 68 hypolipidaemic 69 and anti-oxidant. 70…”