Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis

Abstract

Phytochemical investigation of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang obtained 33 triterpenoid saponins, including 14 new ones, aesculiside C-P (1-14). The structure elucidations were performed through comprehensive MS, 1D and 2D-NMR analysis, and their absolute configuration was unambiguously determined by X-ray diffraction analysis as well as Mo 2 (OAc) 4-induced ECD method for the first time. All the substances were examined for their cytotoxic activities against three tumor cell lines, Hep G2, HCT-116, and MGC-803. Of these, compounds 8, 9, 14-16, 18, and 22 exhibited potent cytotoxicities against all cell lines with IC 50 of 2-21 µM, while compounds 3, 6, 7, 17-19, 20, 24, and 28 depicted moderate activity (IC 50 13 to >40 µM). On these bases, the preliminary structure-activity correlations were also discussed. Meanwhile the neuroprotective properties of triterpenoid saponins from Aesculus genus were evaluated for the first time. Among them, compounds 1, 4, 12, 20, 22, 25, 29, and 31 exhibited moderate activities against C O Cl 2-induced PC12 cell injury.

Phenylethanol glycosides from the seeds of Aesculus chinensis var. chekiangensis

“…Compounds 1-3 (1.0 mg, respectively) was hydrolyzed with 2 M HCl (4.0 mL) at 90 °C for 2 h. Then the hydrolysed materials were disposed and tested by means of the procedure described in our previous work [16,17].…”

“…Compounds 1-4 were assayed for their neuroprotective effects against CoCl 2 -induced PC12 cell injury [18] by 3-(4,5-dimethylthiazol)-2,5-diphenyltetrazolium bromide (MTT) method with trolox as the positive control according to our previously reported procedure [16,17]. PC12 cells were cultured in RPMI-1640 medium containing 10% fetal bovine serum as well as 100 U/mL penicillin/ streptomycin and were incubated at 37 °C with 5% CO 2 .…”

“…var. chekiangensis (Hu et Fang) Fang have led to the isolation of numerous new ones [16,17]. As a continuous search for structurally novel compounds with diverse bioactivities, three new phenylethanol glycosides (1-3) and one known analog (4) were obtained ( Fig.…”

Chemical Constituents with Inhibitory Activities on Proprotein Convertase Subtilisin/kexin Type 9 Expression from the Aerial Parts of Penthorum chinense

“…S23 (A) and 23 (B), Supporting Information). The ECD spectra were plotted using SpecDis v. 1.71 software and applying a Gaussian band shape with a sigma/gamma value of 0.20 eV to simulate the experimental curve ( [17,18] (Fig. S30).…”

Sacraoxides A–G, Bioactive Cembranoids from Gum Resin of Boswellia sacra

“…As part of a continuing research for the discovery of bioactive natural products from medicinal plants ( Xia et al, 2017 ; Zhang et al, 2020 ), a chemical investigation was carried out on the gum resin of B. sacra . Herein, we report the isolation and structural elucidation of nine cembranoids ( 1 – 9 ) as well as their inhibitory activities against lipopolysaccharide (LPS)-induced NO production in RAW 264.7 mouse monocyte-macrophages.…”