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. 2020 Jan 23:7:908.
doi: 10.3389/fchem.2019.00908. eCollection 2019.

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

Nan Zhang  1   2 , Shuxiang Wei  1   2 , Shijie Cao  1   2 , Qiang Zhang  1   2 , Ning Kang  1   2 , Liqin Ding  2 , Feng Qiu  1   2
Affiliations

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

Nan Zhang et al. Front Chem. .

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 Mo2(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 IC50 of 2-21 μM, while compounds 3, 6, 7, 17-19, 20, 24, and 28 depicted moderate activity (IC50 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 COCl2-induced PC12 cell injury.

Keywords: Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang; cytotoxic activities; neuroprotective activities; phytochemistry; triterpenoid saponins.

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Figures

Figure 1
Figure 1
The structures of compounds 1–14.
Figure 2
Figure 2
The selected HMBC (H → C), 1H-1H COSY (H — H) and NOESY (H ↔ H) correlations of compound 1.
Figure 3
Figure 3
The selected HMBC (H → C) and 1H-1H COSY (H — H) correlations of compounds 1–14.
Figure 4
Figure 4
Mo2(OAc)4-induced CD (ICD) spectra of 14a.
Figure 5
Figure 5
ORTEP drawing of 14a.
Figure 6
Figure 6
Neuroprotective activity of compounds 1–33. PC12 cells were exposed to 1 mM CoCl2 for 24 h with or without the indicated concentrations of compounds 1–33, and the cell viability was recorded: (A) compounds 1–5, 10–12; (B) compounds 13, 17, 19–21, 23–25; (C) compounds 26–33; (D) compounds 6–9, 14–16, 18, 22. The data are expressed as means ± SEM. Three independent experiments were performed. *P < 0.05, **P < 0.01.
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