TY - JOUR
T1 - Triterpenoidal saponins from the fruits of Gleditsia caspica with proapoptotic properties
AU - Shaheen, Usama
AU - Ragab, Ehab A.
AU - Abdalla, Ashraf N.
AU - Bader, Ammar
N1 - Funding Information:
This project was funded by the National Plan for Science, Technology and Innovation (MAARIFAH) King Abdulaziz City for Science and Technology , Kingdom of Saudi Arabia, award number ( 12-MED2310-10 ) through Science and Technology Unit (STU) at Umm Al-Qura University .
Publisher Copyright:
© 2017 Elsevier Ltd
PY - 2018/1
Y1 - 2018/1
N2 - Three previously undescribed oleanane-type triterpenoidal saponins named caspicaosides L-N were isolated from the fruits of Gleditsia caspica Desf. The aglycons of these saponins were echinocystic acid, erythrodiol and 12-oleanene-3,28,30-triol. Caspicaoside L is a bisdesmosidic saponin acylated with two monoterpenic acids. It has a disaccharide moiety made up of glucose and arabinose attached to C-3 and pentasaccharide moiety linked to C-28 made up of one glucose, 2 xyloses, one inner rhamnose and one terminal rhamnose which was acylated with two identical monoterpenic acids. Caspicaoside M is a monodesmosidic saponin with a trisaccharide moiety at C-3 made up of glucose, xylose and arabinose, while caspicaoside N has a disaccharide moiety at C-3 made up of glucose and arabinose. Their structures were determined by extensive 1D and 2D (DQF-COSY, HSQC, TOCSY, 1H-13C-HSQC-TOCSY, HMBC, ROESY, NOESY) NMR, HRESIMS analyses and chemical degradation. The cytotoxicity MTT-based assay showed that caspicaosides M, N and L, respectively, exhibited high cytotoxic activity with IC50 ≤ 10 μM (72 h) at least against one of the three used cancer cell lines, MCF 7, A2780 and HT 29; and were 2–34 folds selective against the normal fibroblasts (MRC 5). All compounds also induced apoptosis and caused G2/M arrest in MCF 7 cells (24 h); thus showing pro-apoptotic properties.
AB - Three previously undescribed oleanane-type triterpenoidal saponins named caspicaosides L-N were isolated from the fruits of Gleditsia caspica Desf. The aglycons of these saponins were echinocystic acid, erythrodiol and 12-oleanene-3,28,30-triol. Caspicaoside L is a bisdesmosidic saponin acylated with two monoterpenic acids. It has a disaccharide moiety made up of glucose and arabinose attached to C-3 and pentasaccharide moiety linked to C-28 made up of one glucose, 2 xyloses, one inner rhamnose and one terminal rhamnose which was acylated with two identical monoterpenic acids. Caspicaoside M is a monodesmosidic saponin with a trisaccharide moiety at C-3 made up of glucose, xylose and arabinose, while caspicaoside N has a disaccharide moiety at C-3 made up of glucose and arabinose. Their structures were determined by extensive 1D and 2D (DQF-COSY, HSQC, TOCSY, 1H-13C-HSQC-TOCSY, HMBC, ROESY, NOESY) NMR, HRESIMS analyses and chemical degradation. The cytotoxicity MTT-based assay showed that caspicaosides M, N and L, respectively, exhibited high cytotoxic activity with IC50 ≤ 10 μM (72 h) at least against one of the three used cancer cell lines, MCF 7, A2780 and HT 29; and were 2–34 folds selective against the normal fibroblasts (MRC 5). All compounds also induced apoptosis and caused G2/M arrest in MCF 7 cells (24 h); thus showing pro-apoptotic properties.
KW - Apoptosis
KW - Cytotoxicity
KW - Fabaceae
KW - Gleditsia caspica
KW - Triterpenoidal saponins
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U2 - 10.1016/j.phytochem.2017.11.007
DO - 10.1016/j.phytochem.2017.11.007
M3 - Article
C2 - 29156366
AN - SCOPUS:85034101643
SN - 0031-9422
VL - 145
SP - 168
EP - 178
JO - Phytochemistry
JF - Phytochemistry
ER -