Three new lignanamides from the root of Lycium chinense with anti-inflammatory activity

Abstract

Three new lignanamides, that is, a new lignanamide (1), and a pair of enantiomers (2a and 2b) were isolated from the EtOAc-soluble fraction of an EtOH extract of the root of Lycium chinense. The structures of these new compounds, including their absolute configuration, were established on the basis of HR-ESI-MS, NMR spectroscopic data and quantum chemical ECD calculations. Compound 2a showed significant anti-inflammatory activity in LPS-induced RAW 264.7 macrophages with the IC value of 10.77 ± 2.14 μM, comparing to that of positive control quercetin (17.21 ± 0.50 μM).

Phytochemical Analysis, Anti-inflammatory, and Anticancer Activities of the Halophyte Herb Bassia indica

“…Notably, the isolated chemicals were categorized into various chemical classes including lignans, steroids, amide alkaloids, coumarins, nucleic acid derivatives, phenolic glycosides, flavonoids, and triterpene oleanane saponins (Figure 2). The isolated compounds were identified based on comparison of their spectral data with those reported in the literature, and they were identified as β -sitosterol ( 1 ), 23 syringaresinol ( 2 ), 24 N - trans -feruloyl-3-methoxy tyramine ( 3 ), 25 vanillic acid ( 4 ), 26 o -hydroxybenzoic acid ( 5 ), 27 p -hydroxybenzoic acid ( 6 ), 28 6,7-dihydroxy coumarin ( 7 ), 29 methyl caffeate ( 8 ), 30 caffeic acid ( 9 ), 31 quercetin ( 10 ), 32 N - trans -feruloyl tyramine ( 11 ), 33 uracil ( 12 ), 34 thymidine ( 13 ), 35 tachioside ( 14 ), 36 S -(-)- N - trans -feruloyl normetanephrine ( 15 ), 37 S -(-)- N - trans -feruloyl octopamine ( 16 ), 38 R -( + )- N - trans -feruloyl octopamine ( 17 ), 39 isorhamnetin-3- O - β -D-glucoside ( 18 ), 40 kaempferol-3- O -rutinoside ( 19 ), 41 kaempferol-3- O - β -D-glucopyranosyl-(1→6)- O -[ β -D-galactopyranosyl-(1→3)-2- O - trans -feruloyl- α -L-rhamnopyranosyl-(1→2)]- β -D-glucopyranoside ( 20 ), 21 isorhamnetin-3- O - β -D-glucopyranosyl-(1→6)- O -[ α -L-rhamnopyranosyl-(1→2)]- β -D-glucopyranoside ( 21 ), 21 N -[(3-(3-methyl-1-oxo-butyl)amino)propyl]-3-(3,4-dihydroxyphenyl)prop-2-enamide ( 22 ), 22 3- O -[2′-(2″- O -glycolyl)-glyoxylyl- β -D-glucuronopyranosyl]-28- O - β -D-glucopyranosyl-olean-12-en-3 β -ol-28-oic acid ( 23 ), 21 (2′ R ,3′ S )-3- O -[2′-hydroxy-3′-(2″- O -glycolyl)-oxo-propionic acid- β -D-glucuronopyranosyl]-28- O - β -D-glucopyranosyl-olean-12-en-3 β -ol-28-oic acid ( 24 ), 21 and chikusetsusaponin V ( 25 ) , 42,43 as shown in Supplemental Tables S1 to S5.…”

“…Notably, the isolated chemicals were categorized into various chemical classes including lignans, steroids, amide alkaloids, coumarins, nucleic acid derivatives, phenolic glycosides, flavonoids, and triterpene oleanane saponins (Figure 2). The isolated compounds were identified based on comparison of their spectral data with those reported in the literature, and they were identified as β-sitosterol (1), 23 syringaresinol (2), 24 N-trans-feruloyl-3-methoxy tyramine (3), 25 vanillic acid (4), 26 o-hydroxybenzoic acid (5), 27 p-hydroxybenzoic acid (6), 28 6,7-dihydroxy coumarin (7), 29 methyl caffeate (8), 30 caffeic acid (9), 31 quercetin (10), 32 N-trans-feruloyl tyramine (11), 33 uracil (12), 34 thymidine (13), 35 tachioside ( 14), 36 S-(-)-N-trans-feruloyl normetanephrine (15), 37 S-(-)-N-trans-feruloyl octopamine ( 16), 38 R-( + )-N-trans-feruloyl octopamine (17), 39 isorhamnetin-3-O-β-D-glucoside (18), 40 kaempferol-3-O-rutinoside ( 19), 41…”

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

“…The enantiomer pairs 244a/244b and 245a/245b featuring a spiro[benzofuranone-benzazepine] skeleton from Juglans mandshurica [131], as well as 246a/246b incorporating a benzo[f ] [1,3,5]triazocine backbone from Isatis tinctoria [81], were all reported by the research team of Song and Huang. Compounds 247a/247b are a pair of enantiomers formed by an oxyneolignan and a phenethylamine units from Lycium chinense [132], while 248a/248b and 249a/249b are rearranged nor-lignan amide enantiomers featuring a unique benzo-angular triquinane skeleton from Cannabis sativa [133]. Alkaloids 250−252 were obtained as racemic mixtures from Endiandra kingiana without further chiral separation, and their racemic nature was claimed on the basis of their zero [α] D values [134].…”

“…In contrast, the levorotary enantiomer 407b was much more active (ca. 5 fold) than its antipodal enantiomer 407a in the LPS-induced NO release assay in BV-2 cells [130,132,226,265]. a positive controls.…”

Characterization of Ethyl Acetate and Trichloromethane Extracts from Phoebe zhennan Wood Residues and Application on the Preparation of UV Shielding Films

“…Extracts from Tossa jute leaves, Perilla leaves, and Fenugreek seeds exhibited strong antioxidant activity [4][5][6][7][8]. Extracts were also reported to have biological activities such as anti-inflammatory activity [9][10][11][12], glycosidase inhibition activity [13], protective ability of the liver [14], and antiplatelet activity [15]. Because of the high values of plant extracts, techniques such as supercritical fluid have been explored in order to improve the extract yield and quality [16,17].…”