53846-52-9Relevant academic research and scientific papers
Steroidal Glycosides from the Aerial Parts of Avena sativa L. And Their Cytotoxic Activity
Iguchi, Tomoki,Ishihara, Keita,Mimaki, Yoshihiro,Yamada, Tsuyoshi,Yokosuka, Akihito
, p. 14568 - 14579 (2021/12/13)
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.
Pathways of biotransformation of zingiberen newsaponin from Dioscorea zingiberensis C. H. Wright to diosgenin
Huang, Hongzhi,Zhao, Min,Lu, Li,Tan, Dawei,Zhou, Wenbin,Xiong, Chengqi,Zhao, Yang,Song, Xinbo,Yu, Liyan,Ma, Baiping
, p. 1 - 7 (2013/10/22)
A new steroidal saponin-β-glucosidase from Aspergillus flavus that specifically hydrolyzed the terminal β-d-glucosyl group at the C-3 position of zingiberen newsaponin, deltonin and trillin from Dioscorea zingiberensis C. H. Wright (DZW) was purified, and characterized. The optimal temperature and pH for the new steroidal saponin-β-glucosidase was 50 C and pH 5.0. The steroidal saponin-β-glucosidase was stable at 30-60 C, and retained more than 80% activity. Further, the purified protein was analyzed by ESI-Q-TOF proteomic analyzer. The results indicated that this enzyme is a β-glucosidase of the type glycosidase hydrolase 3 (GH3). Using a combination of the steroidal saponin-β-glucosidase and steroidal saponin-α-1,2-rhamnosidase from Curvularia lunata obtained previously in our lab, the saponins zingieren newsaponin and deltonin could be converted to diosgenin. The pathways of converting zingiberen newsaponin and deltonin into diosgenin by the two key enzymes were elucidated in this study.
Studies on the Constituents of Palmae Plants. II. The Constituents of Rhapis exelsa Henry and R. humilis Bl.
Hirai, Yasuaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo
, p. 4003 - 4011 (2007/10/02)
Further studies have been done on the constituents of the stems, underground parts and leaves of two Palmae plants, Rhapis exelsa Henry and R. humilis Bl.We isolated and identified dioscin, Pb, deltonin, methyl proto-dioscin, methyl proto-Pb and methyl proto-deltonin from the stems, dioscin, methyl proto-dioscin and methyl proto-Pb from the underground parts, and saponaretin (= isovitexin), methyl proto-dioscin, methyl proto-Pb and methyl proto-rhapissaponin from the leaves of R. exelsa.On the other hand we isolated and identified prosapogenin A of dioscin, dioscin, deltonin, methyl proto-prosapogenin A of dioscin, methyl proto-dioscin and methyl proto-deltonin from the stems, dioscin, methyl proto-prosapogenin A of dioscin, methyl proto-dioscin and methyl proto-Pb from the underground parts, and saponaretin, vitexin, isoorientin, methyl proto-prosapogenin A of dioscin, methyl proto-dioscin and methyl proto-Pb from the leaves of R. humilis.Methyl proto-rhapissaponin is a new furostanol saponin and its structure has been established to be 26-O-β-D-glucopyranosyl 22-O-methyl-25(R)-furost-5-en-3β,22,26-triol 3-O-4)-α-L-rhamnopyranosyl(1->4)-α-L-rhamnopyranosyl(1->4)>-2)>-β-D-glucopyranoside.This is the second report of the isolation of steroidal saponins from Palmae plants, and the results are interesting from the standpoint of chemotaxonomy. Keywords - Rhapis exelsa; Rhapis humilis; Palmae; steroidal saponin; furostanol oligoside; diosgenin; flavone glycoside; flavone C-glycoside; methyl proto-rhapissaponin
