Phenylpropanoids from Liparis nervosa and their in vitro antioxidant and α-glucosidase inhibitory activities

Abstract

Eleven phenylpropanoids were isolated from the whole grass of Liparis nervosa, an orchidaceous medicinal plant. Their structures were elucidated as (+)-Syringaresinol (1), (-)-Syringaresinol-4-O-β-Dglucopyranoside (2), Sinapaldehyde (3), Coniferyl aldehyde (4), Syringin (5), Sinapaldehye glucoside (6), 2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone ( 7), C-Veratroylglycol (8), 7S, 7′S, 8R, 8′Ricariol A 2 (9), Erigeside 2 (10), and Methylsyringin (11) by comparing the spectroscopic data and physicochemical constants from the isolated compounds with the data reported in the literature. Compounds 1 and 9 were found to have potent in vitro antioxidant activities in the DPPH and ABTS assays, and their IC 50 values were lower than those of vitamin C. More importantly, compound 9 had a strong α-glucosidase inhibitory activity with an IC 50 value of 43.76 ± 2.03 µM, which was much lower than that of acarbose (IC 50 = 273.12 ± 11.84 µM), indicating that compound 9 has the potential for the development of hypoglycemic drugs. In conclusion, the present study suggests that phenylpropanoids may be the additional representative type of active constituents in L. nervosa, which provides a new line of evidence to understand this medicinal plant.

Chemical Constituents of Thesium chinense Turcz and Their In Vitro Antioxidant, Anti-Inflammatory and Cytotoxic Activities

“…Beside the three novel compounds ( 1–3 ), twenty-six known compounds ( 4–29 ), including two steroids ( 4–5 ) and twenty-four phenylpropanoids ( 6–29 ), were also identified from the whole plants of T. chinense . Their strctures were determined as: perlplogemn [ 15 ] ( 4 ), periplocin [ 16 ] ( 5 ), 2-hydroxy-5-(2-hydroxy-ethyl) phenyl- β -D-glucopyranoside ( 6 ) [ 11 ], 3, 5-dihydroxyphenethyl alcohol 3- O - β -D-glucopyranoside ( 7 ) [ 17 ], phenethyl alcohol β -sophoroside ( 8 ) [ 18 ], samsesquinoside ( 9 ) [ 19 ], pinoresinol-4- O -D- glucoside ( 10 ) [ 20 ], syringaresinol-4′- O - β -D-glucopyranoside ( 11 ) [ 21 ], dihydrodehydro diconiferyl alcohol 4- O - β -D-glucoside ( 12 ) [ 22 ], (7S, 8R) 9′- methoxy- dehydrodiconiferyl alcohol 4- O -β-D-glucopyranoside ( 13 ) [ 23 ], picraquassioside C ( 14 ) [ 24 ], citrusin A ( 15 ) [ 25 ], citrusin B ( 16 ) [ 25 ], (erythro, erythro)-1-[4-[2-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-1-(hydroxy methyl) ethoxy]-3, 5-dimethoxy phenyl]-1, 2, 3-propanetriol ( 17 ) [ 26 ], 1-(4-hydroxy-3-methoxy)-phenyl -2-[4-(1, 2, 3-trihydroxy propyl)-2-methoxy]-phenoxy-1, 3-propan-diol ( 18 ) [ 27 ], lariciresinol-4- O - β -D-glucoside ( 19 ) [ 28 ], ficusal ( 20 ) [ 29 ], 3- O -ethyl ferulate ( 21 ) [ 30 ], p -coumaric acid ( 22 ) [ 31 ], feruloylquinic acid ( 23 ) [ 32 ], syringin ( 24 ) [ 33 ], coniferin ( 25 ) [ 34 ], alatusol D ( 26 ) [ 35 ], scopolin ( 27 ) [ 36 ], scopoletin ( 28 ) [ 36 ] and sinapaldehyde glucoside ( 29 ) [ 37 ]. All the known compounds ( 4–29 ) were isolated from Thesium chinense Turcz for the first time.…”

Anti-Inflammatory Activity of Cajanin, an Isoflavonoid Derivative Isolated from Canavalia lineata Pods

“…The methanol extract (152.1 g) of C. lineata pods suspended in H 2 O was successively partitioned into EtOAc- (15.2 g) and BuOH-soluble (9.6 g) fractions, which were subjected to C 18 column chromatography, MPLC, and preparative HPLC to obtain 1 new flavonoid ( 2 ) and 12 known compounds ( Figure 1 and Figure S1 ), including rutin ( 1 ) [ 15 ], (2 R ,3 R )-3,7-dihydroxy- 6-methoxyflavanone ( 3 ) [ 16 ], prunetin ( 4 ) [ 17 ], 7,4′-dimethoxyisoflavone ( 5 ) [ 18 ], ononin ( 6 ) [ 19 ], cajanin ( 7 ) [ 20 ], 7,4′-dimethyl-3′-hydroxygenistein ( 8 ) [ 21 ], medicarpin ( 9 ) [ 19 ], homopterocarpin ( 10 ) [ 22 ], pterocarpin ( 11 ) [ 23 ], (+)-syringaresinol ( 12 ) [ 24 ], and (−)-syringaresinol-4- O - β - d -glucopyranoside ( 13 ) [ 24 ]. This is the first report of compounds 1 – 13 from C. lineata , and all the isolates were evaluated for their inhibitory activity on the LPS-stimulated production of the proinflammatory mediators NO, IL-6, and TNF-α in RAW264.7 cells.…”

Chemical Composition, In Vitro Antioxidant Activities, and Inhibitory Effects of the Acetylcholinesterase of Liparis nervosa (Thunb.) Lindl. Essential Oil

“…Although various studies focus on chemical-compound isolation-including lectin, nervonic acid derivatives, phenylpropanoids, pyrrolizidine alkaloids derivatives, and pyrrolizidine alkaloids, which have anti-fungal, anti-tumor, antioxidant, and α-glucosidase inhibitory properties [16][17][18][19][20], however the chemical composition, antioxidant activities, and acetylcholinesterase inhibitory effects of the EOs of this species remain unexplored. Thus, the present study was carried out to assess the phytochemical composition and biological activities of EO from L. nervosa.…”