Abstract
A new triterpenoidal saponin identified as 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-xylopyranosyl]-2β,3β,16α-trihydroxyolean-12-en-23,28-dioic acid-28-O-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside 1 together with a new oleanane triterpene identified as 2β,3β,13α,22α-tetrahydroxy olean-23,28-dioic acid 2 and 6 known compounds (3–8) have been isolated from Gladiolus segetum Ker-Gawl corms. The structural elucidation of the isolated compounds was confirmed using different chemical and spectroscopic methods, including 1D and 2D NMR experiments as well as HR-ESI-MS. Moreover, the in vitro cytotoxic activity of the fractions and that of the isolated compounds 1–8 were investigated against five human cancer cell lines (PC-3, A-549, HePG-2, MCF-7 and HCT-116) using doxorubicin as a reference drug. The results showed that the saponin fraction exhibited potent in vitro cytotoxic activity against the five human cancer cell lines, whereas the maximum activity was exhibited against the PC-3 and A-549 cell lines with the IC50 values of 1.13 and 1.98 μg mL−1, respectively. In addition, compound 1 exhibited potent activity against A-549 and PC-3 with the IC50 values of 2.41 μg mL−1 and 3.45 μg mL−1, respectively. Interestingly, compound 2 showed the maximum activity against PC-3 with an IC50 of 2.01 μg mL−1. These biological results were in harmony with that of the molecular modeling study, which showed that the cytotoxic activity of compound 2 might occur through the inhibition of the HER-2 enzyme.
Highlights
IntroductionMedicinal applications as drug entities and there are many others that can serve as chemical models or templates for synthesis, semi-synthesis and the design of novel drug candidates for the treatment of human diseases.[2]
Natural products and their derivatives are of great importance and have been recognized for many years as an important source of therapeutic agents for the treatment of several diseases.[1]
Its molecular formula was established as C70H112O38 based on the positive ion mode HR-Electronic supplementary information (ESI)-MS
Summary
Medicinal applications as drug entities and there are many others that can serve as chemical models or templates for synthesis, semi-synthesis and the design of novel drug candidates for the treatment of human diseases.[2]. The hot water extracts of dried corms are used for the treatment of ulcers.[6] the phytochemical survey of the genus Gladiolus showed an interesting wide diversity of chemical constituents, such as anthraquinones,[4,5,7] avonoids,[8] triterpenes,[4] saponins,[9] and lignans.[10] There are several approaches to drug discovery, such as combinatorial chemistry and computer-based molecular modeling design based on natural products,[2] in addition to drug discovery using natural products, which. The docking study of the isolated compounds was carried out against human epidermal receptor 2 (HER-2) at the catalytic ligand binding site (PDBID: 5jeb) to help better understand the binding mode and their possible mechanism of action as potential new anticancer agents
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