Syringin: A Phenylpropanoid Glycoside Compound in Cirsium brevicaule A. GRAY Root Modulates Adipogenesis

Abstract

Cirsium brevicaule A. GRAY is a wild perennial herb, and its roots (CbR) have traditionally been used as both food and medicine on the Japanese islands of Okinawa and Amami. The present study evaluated the antiadipogenic effect of CbR using mouse embryonic fibroblast cell line 3T3-L1 from JCRB cell bank. Dried CbR powder was serially extracted with solvents of various polarities, and these crude extracts were tested for antiadipogenic activity. Treatment with the methanol extract of CbR showed a significant suppression of lipid accumulation in 3T3-L1 cells. Methanol extract of CbR was then fractionated and subjected to further activity analyses. The phenylpropanoid glycosidic molecule syringin was identified as an active compound. Syringin dose dependently suppressed lipid accumulation of 3T3-L1 cells without cytotoxicity, and significantly reduced the expressions of peroxisome proliferator-activated receptor gamma, the master regulator of adipogenesis, and other differentiation markers. It was demonstrated that syringin effectively enhanced the phosphorylation of the AMP-activated protein kinase and acetyl-CoA carboxylase. These results indicate that syringin attenuates adipocyte differentiation, adipogenesis, and promotes lipid metabolism; thus, syringin may potentially serve as a therapeutic candidate for treatment of obesity.

Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik

“…The 1 H- and 13 C-NMR data based on 1D and 2D-NMR measurements as well as HRMS supported the proposed structures of 4 and 6 . The corresponding spectroscopic data presented in the experimental as well as in Table 1 and Table 2 were in good accordance with those reported [ 47 , 51 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 ].…”

“…In total, nine compounds were isolated, including six sucrose esters, namely 6,3′-disinapoyl-sucrose ( 1 ) [ 74 ], 6- O -sinapoyl,3′- O -trimethoxy-cinnamoyl-sucrose (tenuifoliside C) ( 2 ) [ 51 , 75 ], 3′- O -( O -methyl-feruloyl)-sucrose ( 3 ) [ 76 ], 3′- O -sinapoyl-sucrose ( 4 ) [ 77 ], 3′- O -trimethoxy-cinnamoyl-sucrose (glomeratose) ( 5 ) [ 78 ], and 3′- O -feruloyl-sucrose (sibiricose A5) ( 6 ) [ 79 ]. Additionally, a monomeric phenylpropane glycoside, sinapyl alcohol 4- O -glucoside (syringin or eleutheroside B) ( 7 ) [ 80 , 81 ], a tetrahydrofurofuran-type lignan diglycoside, liriodendrin ( 8 ) [ 82 , 83 , 84 ], and a flavonol glycoside, and 7,4-di- O -methylquercetin-3- O -β-rutinoside (ombuin 3- O -rutinoside or ombuoside) ( 9 ) [ 47 , 85 ] were isolated ( Figure 1 ). The structure elucidation of the compounds 1 – 9 was based on the 1D- and 2D-NMR experiments ( 1 H-, 13 C-NMR, COSY, HSQC, HMBC, and NOESY) and were confirmed by the HRMS analysis (see Supplementary Materials ).…”

Lignans and some other non-alkaloid compounds from the stem bark of Zanthoxylum rhetsa and their biological activities

“…The presence of β-D-glucopyranose was confirmed by signals of one anomeric carbon at δ C 105.4 (C-1') and one oxymethylene carbon at δ C 62.6 (C-6'). Comparison of the above data with those reported in the work of Hossin et al, 20 compound 7 was identified as syringin (Figure 1). Syringin was found in Zanthoxylum ailanthoides , 21 but this is the first time this compound was isolated from Z. rhetsa .…”

Origanum majorana L.: A Nutritional Supplement With Immunomodulatory Effects

“…Procumboside B belongs to the type phenylpropanoid, which has a variety of pharmacological effects, including antitumor, anti-oxidation, antibacterial, antiviral, anti-inflammatory, analgesic, hypotensive, enzyme inhibitory, and immunosuppressive activities ( 50 ). The phenylpropanoids in lilacs regulated adipogenesis ( 51 ). The anti-inflammatory effect of phenylpropanoids from Dendropanax dentigerous was exerted by inhibiting NF-κB, AKT, and JNK signaling pathways in TNF-α-induced MH7A cells ( 52 ).…”