Hypoglycemic and Anti-Inflammatory Effects of Triterpene Glycoside Fractions from Aeculus hippocastanum Seeds

Horse chestnut (Aesculus hippocastanum L.)-derived drugs have shown their potential in biomedical applications. The seed of A. hippocastanum contains various kinds of chemical compounds including phenolics, flavonoids, coumarins, and triterpene saponins. Here, we investigated the chemical components in A. hippocastanum L. grown in Uzbekistan, which has not yet been studied in detail. We identified 30 kinds of triterpene saponins in an extract of A. hippocastanum L. Classifying extracted saponins into eight fractions, we next studied the hypoglycemic and the anti-inflammatory activities of escin and its derivatives through in vivo experiments. We came by data indicating the highest (SF-1 and SF-2) and the lowest (SF-5 and SF-8) antidiabetic and anti-inflammatory effects of those eight fractions. These results imply the prospective use of A. hippocastanum L. grown in Uzbekistan in the production of pharmaceutical drugs to treat diabetes and inflammation.

Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages

A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ20(21) in ring E. The structure of isomadecassoside was established by means of HR-ESIMS and detailed analysis of 1D and 2D NMR spectra, which allowed a complete NMR assignment. Studies on isolated J774A.1 macrophages stimulated by LPS revealed that isomadecassoside (4) inhibited nitrite production at non-cytotoxic concentrations, thus indicating an anti-inflammatory effect similar to that of madecassoside.

ANTIOXIDANT ACTIVITY OF TRITERPENE GLYCOSIDE (CORTUSOSIDE A) FROM CORTUSA MATTHIOLI L. PLANT

The antioxidant activity of triterpene glycoside, first isolated from the aboveground part of the plant Cortusa matthioli L. and identified as β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside-(1→3)-13β,28-epoxyolean-30-al-3β,16α-diol (cortusoside A), is studied. Tests for the ability of cortusoside A to bind 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals did not reveal any activity of this compound. However, in experiments to study the ability to chelate Fe2+ ions, its sufficiently high iron chelating activity was found, which was only 2.24 times lower compared to the powerful Fe2+ chelator dipyridyl. The EC50 values for cortusoside A and dipyridyl were 0.417±0.057 and 0.186±0.018 mM, respectively. Literature analysis has shown that the structural analogue of cortusoside A, saxifragifolin B, has a much weaker iron chelating ability (13,4 times) compared to the standard Fe2+ EDTA-Na2 ion chelator, as well as a weak ability to bind free radicals of DPPH compared to the reference antioxidants – catechin and ascorbic acid (50 and 32 times, respectively). Despite the structural identity of the molecules cortusoside A and saxifragifolin B, low radiculopathy activity cortusosoide A may be due to differences in the structure of these substances (optical or geometric isomerism), as well as different methods were used in its definition.

Araliaarmoside: A New Triterpene Glycoside Isolated From the Leaves of Aralia armata

One new oleanane-type triterpene glycoside, oleanolic acid-[28 -O-β-d-glucopyranosyl]-3 -O-[ β-d-glucopyranosyl(1→6)- β-d-glucopyranosyl](1→3)[ α-l-arabinofuranosyl(1→4)]- β-d-glucuronopyranoside (1), and 3 known ones {oleanolic acid-[28 -O-β-d-glucopyranosyl]-3 -O-[ β-d-galactopyranosyl(1→3)]-[ β-d-glucopyranosyl(1→2)]- β-d-glucuronopyranoside (2) chikusetsusaponin IVa methyl ester (3), and chikusetsusaponin IV (4)} were isolated from the leaves of Aralia armata. Their chemical structures were elucidated using a combination of high-resolution electrospray ionization mass spectrometry, 1-dimensional and 2-dimensional nuclear magnetic resonance (NMR) spectral data, as well as comparison with data in the previous literature. This is the first report of full NMR spectroscopic data of 2. Compounds 1-4 displayed weak cytotoxic activity toward KB and HepG2 cell lines, with half-maximal inhibitory concentration50 values ranging from 24.2 ± 0.3 to 32.6 ± 0.8 µM in in vitro assay.