512-04-9Relevant articles and documents
Anti-allergic substances from the rhizomes of Dioscorea membranacea
Tewtrakul, Supinya,Itharat, Arunporn
, p. 8707 - 8711 (2006)
Extracts of five species of Thai medicinal plants, locally known as Hua-Khao-Yen, were screened for anti-allergic activities using RBL-2H3 cells. Of the five species studied, the ethanolic extract of Dioscorea membranacea exhibited potent inhibitory activity against β-hexosaminidase release as a marker of degranulation in RBL-2H3 cells, with an IC50 value of 37.5 μg/mL. Eight compounds were isolated from this crude ethanolic extract, [two naphthofuranoxepins (1, 2), one phenanthraquinone (3), three steroids (4-6), and two steroidal saponins (7, 8)], and tested for their anti-allergic activities. The results showed that dioscorealide B (2) possessed the highest activity with an IC50 value of 5.7 μM, followed by dioscoreanone (3, IC50 = 7.7 μM), dioscorealide A (1, IC50 = 27.9 μM), and diosgenin (9, IC50 = 29.9 μM). Structure-activity relationship studies of naphthofuranoxepins on anti-allergic activity revealed that the hydroxylation at position 8 conferred higher activity than methoxylation. For diosgenin derivatives, the aglycone was found to possess higher activity than the diglucosylated molecule; whereas substitution with rhamnoglucosides apparently results in loss of activity. Furthermore, effects of dioscorealide A, dioscorealide B, and dioscoreanone on antigen-induced release of TNF-α and IL-4 in the late phase reaction were also examined.
FUROSTANOL GLYCOSIDES FROM TRIGONELLA FOENUM-GRAECUM SEEDS
Gupta, Rajesh K.,Jain, Dharam C.,Thakur, Raghunath S.
, p. 2605 - 2608 (1984)
Two new furostanol glycosides, trigofoenosides F and G, have been isolated as their methyl esters from the methanolic extract of Trigonella foenum-graecum seeds (Leguminosae).The structures of the original glycosides have been determined as (25R)-furost-5-en-3β,22,26-triol, 3-O-α-L-rhamnopyranosyl(1->2)β-D-glucopyranosyl(1->6)β-D-glucopyranoside; 26-O-β-D-glucopyranoside and (25R)-furost-5-en-3β,22,26-triol, 3-O-α-L-rhamnopyranosyl(1->2)4)>β-D-glucopyranosyl(1->6)β-D-glucopyranoside; 26-O-β-D-glucopyranoside, respectively.Key Word Index - Trigonella foenum-graecum; Leguminosae (Fabaceae); fenugreek; furostanol glycosides.
Spirostanol glycosides from Asparagus plumosus
Sati,Pant
, p. 123 - 126 (1985)
Three spirostanol glycosides were isolated from a methanol extract of the leaves of Asparagus plumosus and characterized.
Bivalent furostene carbamates as antiproliferative and antiinflammatory agents
Pathak, Nandini,Fatima, Kaneez,Singh, Sneha,Mishra, Divya,Gupta, Amit Chand,Kumar, Yogesh,Chanda, Debabrata,Bawankule,Shanker, Karuna,Khan, Feroz,Gupta, Atul,Luqman, Suaib,Negi, Arvind S.
, (2019/09/03)
Breast cancer is the most prevalent cancer in women affecting about 12% of world's female population. It is a multifactorial disease, mostly invasive in nature. Diosgenin and related compounds are potent antiproliferative agents. Carbamate derivatives have been synthesized at C26 of furostene ring after opening spiroketal bond (F-ring) of diosgenin. Compound 10 possessed significant antiproliferative activity against human breast cancer cells by arresting the population at G1 phase of cell division cycle and induced apoptosis. Induction of apoptosis was observed through the caspase signalling cascade by activating caspase-3. Moreover, carbamate 10 exhibited moderate antiinflammatory activity by decreasing the expression of cytokines, TNF-α and IL-6 in LPS-induced inflammation in primary macrophage cells. Furthermore, compound 10 significantly reduced Ehrlich ascites carcinoma significantly in mice. It was well tolerated and safe in acute oral toxicity in Swiss albino mice. The concomitant anticancer and antiinflammatory properties of carbamate 10 are important and thus, can further be optimized for a better anti-breast cancer candidate.
New furostanol glycosides from Polygonatum multiflorum (L.) All
Gvazava, Lili,Nebieridze, Vazha,Ganzera, Markus,Skhirtladze, Alexander
, p. 9 - 16 (2018/02/09)
The phytochemical investigation of the whole plant of Polygonatum multiflorum resulted in the isolation of two new steroidal glycosides, polmultoside A (4) and polmultoside B (5), along with three known glycosides protobioside (1), protodeltonin (2) and huangjiangsu A (3). The structures of the isolated compounds have been elucidated by extensive 1D (1H, 13C) and 2D (COSY, HSQC, HMBC) NMR spectral data analysis, as well as high-resolution mass determinations.
From organocatalysed desilylations to high-yielding benzylidenations of electron-deficient benzaldehydes
Niu, Qun,Xing, Linlin,Li, Chunbao
, p. 358 - 364 (2017/06/19)
A new type of organoprecatalyst (MeSCH2Cl/KI) for desilylation and benzylidenation reactions has been designed. Both reactions are user friendly and high yielding (71->99%) and have fast reaction rates. The desilylation of iodo silyl ethers was achieved with no sequential etherification side reactions like those seen for reactions when using TBAF. In the application of the catalytic system to a 6-TBDMS ether of a glucoside, glucoside benzylidenations using electron-deficient benzaldehydes were achieved in 87% yield compared with the previously reported yields of 69-77%. Altogether, 14 benzylidenation reactions were realised using silyloxy alcohols and electrondeficient benzaldehydes instead of their activated acetal forms. In terms of reaction rates and yields, the order of the benzylidenations is p-fluorobenzaldehyde > benzaldehyde > p-anisaldehyde, and a possible mechanism is discussed. These experiments have preliminarily differentiated this cost-effective catalytic system from the classic Lewis acids.
Novel steroidal glycosides from the bulbs of lilium pumilum
Matsuo, Yukiko,Takaku, Reina,Mimaki, Yoshihiro
, p. 16255 - 16265 (2015/12/01)
Examination of the bulbs of Lilium pumilum (Liliaceae) led to the isolation of four novel steroidal glycosides (1-4) with a 2,3,4-trisubstituted β-D-glucopyranosyl unit. In 1 and 3, the α-L-arabinopyranosyl moiety is linked to C-3 of the inner trisubstituted β-D-glucopyranosyl group and is present as an usual 4C1 conformation. In contrast, in 2 and 4, the α-L-arabinopyranosyl moiety, which is attached to C-4 of the inner trisubstituted β-D-glucopyranosyl group, is present as a 1C4 conformation. The structures of the new steroidal glycosides were determined based on the results of spectroscopic analyses, including two-dimensional (2D) NMR data and hydrolysis.
Electrochemical synthesis of glycoconjugates from activated sterol derivatives
Tomkiel, Aneta M.,Kowalski, Jan,P?oszyńska, Jolanta,Siergiejczyk, Leszek,?otowski, Zenon,Sobkowiak, Andrzej,Morzycki, Jacek W.
, p. 60 - 67 (2014/03/21)
Several derivatives of cholesterol and other 3β-hydroxy- Δ5-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors.
Unexpected fragmentation of 16β-acetoxy-22-oxocholestanes on the action of methylenetriphenylphosphorane
Valiullina, Zuleykha R.,Khasanova, Lidiya S.,Selezneva, Natalya K.,Gimalova, Fanuza A.,Pivnitsky, Kasimir K.,Miftakhov, Mansur S.
, p. 272 - 273 (2015/02/05)
Treatment of 16β-acetoxy-22-oxocholestanes with methylenetriphenylphosphorane results in the cleavage of C22-C23 bond and formation of bisnorcholanic (22→16)-lactones. The analogous fragmentation also partially proceeds on ButOK action.
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.
