Study on the chemical composition of Caesalpinia sinensis

Abstract

Five compounds were isolated from the methanolic extract of Caesalpinia sinensis branches and leaves including a new cassane-type butenolide norditerpenoids compound (1) and a new type of biphenyls compound (2); the compounds were identified as Norcaesalpin-one (1), 4'-hexyl 3-methyl 6methoxy-[1,1'-biphenyl]-3,4'-dicarboxylate (2), rhapontigenin (3), 3-deoxysappanchalcone (4), isoliquiritigenin (5). Compounds 1-5 were first isolated from C. sinensis. Their structures were elucidaded on the basis of MS, IR, NMR spectroscopic, X-ray diffraction data analyses. The NGFinduced PC12 differentiation assay was performed on compound 1, and the results showed that compound 1 had a promotive effect on PC12 cell differentiation, with a differentiation rate of 12.32%. In addition, In addition, compounds 1-5 were evaluated for their cytotoxic activities against five human cancer cell lines (including A-549, BGC-823, MDA-MB-231, HepG2), and the results showed that compounds 3-5 showed inhibitory activity against to these cancer cell lines, with IC 50 values ranging from 22.96 to 74.92 μmol/L, with compound 4 showing the best activity against human malignant melanoma cells A375 with an IC 50 value of 22.96 μmol/L.

3-Deoxysappanchalcone isolated from Caesalpinia sinensis shows anticancer effects on HeLa and PC3 cell lines: invasion, migration, cell cycle arrest, and signaling pathway

“…C. sinensis infusion was mixed in 5 L water and extracted with n-butanol to obtain a 50.12 g extract. The extract was first subjected to column chromatography on silica gel (dichloromethane; methanol, 250:1) and then purified by high-performance thin-layer chromatography (HPTLC) to get a pale yellow solid of 8.2 mg (3-DSC) [ 13 ]. NMR data (BrukerAV, Germ): ESI-MS m / z : 269.2 [M−H] − , 1 HNMR (400 MHz, CD 3 OD) δ : 7.65 (1H, d, J = 15.7 Hz, H- β ), 7.40 (1H, d, J = 15.7 Hz, H- α ), 7.57 (1H, d, J = 8.5 Hz, H-6′), 6.45 (1H, dd, J = 8.5, 2.0 Hz, H-5′), 6.50(1H, d, J = 2.0 Hz, H-3′), 7.49 (2H, d, J = 8.7 Hz, H-2, 6), 6.82 (2H, d, J = 8.7 Hz, H-3, 5), 3.83 (3H, s, –OCH 3 ).…”

“…13 C-NMR δ : 188.95 (C=O), 162.68 (C-2′), 160.49 (C-4′), 159.72 (C-4), 141.46 (C- β ), 132.33 (C-6′), 130.35 (C-2, 6), 126.09 (C-1), 124.00 (C- α ), 120.32 (C-1′), 115.96 (C-3, 5), 107.94 (C-5′), 99.33 (C-3′), 55.74 (-OCH 3 ). The 13 C-NMR data were identified as 3-deoxysappanchalcone [ 13 ].…”

“…Caesalpinia sinensis contains flavonoids, terpenoids, alkaloids, and steroids with anti-inflammatory, antioxidant, antiviral, antibacterial, and neuroprotective activities [ 11 , 12 ]. 3-deoxysulforaphane (3-DSC) is the active ingredient in C. sinensis [ 13 ]. Meanwhile, 3-DSC activates AKT (serine/threonine-specific protein kinase)/mTOR to induce HO-1 for anti-inflammation and also inhibits intracellular CCL5 and CXCL10 secretion to protect host cells from influenza virus-induced inflammatory, with anti-influenza effects [ 14 , 15 ].…”