Steroidal Glycosides from the Aerial Parts of Avena sativa L. and Their Cytotoxic Activity

Abstract

Twelve steroidal glycosides (1–12) were isolated from the aerial parts of Avena sativa L. (Poaceae). Among the isolated compounds, 1 was directly isolated from the plant for the first time, and 2–6 were new steroidal glycosides. The structures of 1–6 were determined by analysis of their spectroscopic data, chemical transformations, and chromatographic and spectroscopic analyses of the hydrolyzed products. Compounds 5 and 6 were novel steroidal glycosides with a B-ring contracted skeleton (B-nor steroid). Compounds 1, 9, 11, and 12 were cytotoxic to HL-60 human promyelocytic leukemia cells, MIA PaCa-2 human pancreatic carcinoma cells, and A549 human lung adenocarcinoma cells with IC50 values ranging from 0.79 to 13.5 μM. HL-60 cells treated with 1 exhibited apoptotic characteristics, namely, condensed nuclear chromatin, accumulation of sub-G1 cells, and activation of caspase-3. Additionally, the loss of the mitochondrial membrane potential and the release of cytochrome c into the cytoplasm in 1-treated HL-60 cells suggested that 1 induced apoptosis through a mitochondrial-dependent apoptotic pathway.

Characterization of Seven New Steroidal Saponins from Korean Oat Cultivars by UPLC-QTOF-MS and UPLC-MS/MS

“…Compounds 21 and 22 exhibited avenestergenin A 1 and B 1 ions at m / z 638[aglycone+H] + and 622[aglycone+H] + , respectively ( Figures 3 , 4 , and S2 ). Based on their MS spectroscopic data and the elution order reported in the literature, 14 , 18 , 21 , 22 , 24 , 28 and standard (avenacoside A), peaks 4 , 7 , 10 , 12 - 15 , and 18 - 22 were identified as sativacosides B, A, and C, avenacosides D, B, A, and C, 26-desglucoavenacosides A and C, 3- O -glucosyl-nuatigenin, and avenacins A 1 and B 1 , respectively, and are detailed in Table 1 .…”

“…Peaks 1, 2, and 12-20 were determined to be furospirostane, peaks 3-11 were determined to be furostane, and peaks 21 and 22 were determined to be oleanane saponins esterified with phenolic acid (Figures 1, 2 3, 4, and S2). Based on their MS spectroscopic data and the elution order reported in the literature, 14,18,21,22,24,28 and standard (avenacoside A), peaks 4, 7, 10, 12-15, and 18-22 were identified as sativacosides B, A, and C, avenacosides D, B, A, and C, 26-desglucoavenacosides A and C, 3-O-glucosyl-nuatigenin, and avenacins A 1 and B 1 , respectively, and are detailed in Table 1. 1 and 2).…”

“…Oats contain two types of saponins: Triterpenoid saponins, including avenacins A 1 , A 2 , B 1 , B 2 , and C–K, have been reported in oat bran and roots, , whereas steroidal saponins, avenacosides A–C, and their derivatives have been reported in oat shoots, , grains, − husks, brans, ,, and aerial parts , and they have bioactivities, such as antibacterial, antifungicidal, , osteogenic, and anticancer. , Analytical methods for these compounds have mainly focused on NMR and MS analysis, but recently, high-resolution mass spectrometric methods, such as QToF-MS, have the efficiency to isolate and identify numerous components . Furthermore, previous studies on the quantification of oat saponins were mainly limited to evaluating the content of crude saponin or major components, such as avenacosides A and B. ,,,,, Thus, the objective of this study is to rapidly and accurately characterize saponin derivatives based on internal and external standards.…”

Structure Elucidation of 16 Undescribed Steroidal Glycosides from the Underground Parts of Agapanthus africanus and Apoptosis-Inducing Activity in Small-Cell Lung Cancer Cell

“…Compounds 1 and 10 exhibited dose-dependent cytotoxic activities against all three cell lines (Figure 4). The cytotoxic activities of 1 were attenuated by the dehydrogenation of C-7/8 and C-9/11 (2), degalactosylation (3), and dehydrogenation of C-20/22 (14). On the other hand, although 9 did not show any cytotoxicity against the three cell lines at a sample concentration of 50 μM, the C-7/8 dehydro derivative of 9 (10) was considerably cytotoxic to all three cell lines.…”

“…Approximately 25% of all new anticancer agents approved by the Food and Drug Administration (FDA) between January 01, 1981, and September 30, 2019, were developed from natural products and natural product derivatives . In our continuous quest for the search for new candidates for anticancer agents from higher plants, we have discovered various cytotoxic steroidal glycosides from Cestrum nocturnum, Ornithogalum thyrsoides, Allium karataviense, Yucca glauca, Dracaena thalioides, Ornithogalum saundersiae, Convallaria majalis, Helleborus foetidus, Withania somnifera, Thevetia neriifolia, Avena sativa, and Digitalis purpurea . Currently, we have focused on the constituents of Agapanthus africanus (L.) Hoffmanns.…”