126-19-2Relevant articles and documents
Steroidal saponins from Asparagus racemosus
Sharma, Upendra,Saini, Rikki,Bobita,Kumar, Neeraj,Singh, Bikram
, p. 890 - 893 (2009)
Two new steroidal saponins, shatavaroside A (1) and shatavaroside B (2) together with a known saponin, filiasparoside C, were isolated from the roots of Asparagus racemosus. Filiasparoside C was first time isolated from this plant. Their structures were e
SPIROSTANOL GLYCOSIDE FROM FRUITS OF ASPARAGUS OFFICINALIS
Pant, G.,Panwar, M. S.,Negi, D. S.,Rawat, M. S. M.,Morris, G. A.
, p. 3324 - 3325 (1988)
A spirostanol glycoside was isolated, together with some known compounds, from the methanolic extract of the fruits of Asparagus officinalis and characterized by chemical and spectral methods including 13C NMR-DEPT and 2D-hetcor NMR spectra.The spirostanol glycoside caused 100percent immobilization of human spermatozoa at 1.5percent level.Key Word Index - Asparagus officinalis; Liliaceae; spirostanol glycoside; 13C NMR-DEPT mode; 2D-heteronuclear shift correlation NMR spectrum; spermicidal potential.
Filiasparosides A-D, cytotoxic steroidal saponins from the roots of Asparagus filicinus
Zhou, Li-Bo,Chen, Tzu-Hsuan,Bastow, Kenneth F.,Shibano, Makio,Lee, Kuo-Hsiung,Chen, Dao-Feng
, p. 1263 - 1267 (2007)
Four new steroidal saponins, filiasparosides A-D (1-4), together with known aspafiliosides A (5) and B (6) were isolated from the roots of Asparagus filicinus. The structures of these new compounds were elucidated by detailed spectroscopic study and chemical analysis. Compounds 1-6 were cytotoxic against human lung carcinoma (A549) and breast adenocarcinoma (MCF-7) tumor cell lines with EC50 values of 2.3-16.8 μg/mL. Compound 3 showed the most potent cytotoxicity, with EC50 values of 2.3 and 3.0 μg/mL toward A549 and MCF-7 cell lines, respectively.
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Kenney,Wall
, p. 468 (1957)
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Marker,Rohrmann
, p. 900 (1940)
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Concise large-scale synthesis of tomatidine, a potent antibiotic natural product
Boudreault, Pierre-Luc,Normandin, Chad
, (2021/10/12)
Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high cost, an efficient and scalable multi-gram synthesis of tomatidine has been developed. This synthesis uses a Suzuki–Miyaura-type coupling reaction as a key step to graft an enantiopure F-ring side chain to the steroidal scaffold of the natural product, which was accessible from low-cost and commercially available diosgenin. A Lewis acid-mediated spiroketal opening followed by an azide substitution and reduction sequence is employed to generate the spiroaminoketal motif of the natural product. Overall, this synthesis produced 5.2 g in a single pass in 15 total steps and 15.2% yield using a methodology that is atom economical, scalable, and requires no flash chromatography purifications.
Gram-Scale Synthesis of Tomatidine, a Steroid Alkaloid with Antibiotic Properties Against Persistent Forms of Staphylococcus aureus
Normandin, Chad,Malouin, Fran?ois,Marsault, Eric
, p. 2693 - 2698 (2020/05/04)
We herein describe the first diastereoselective synthesis of the Solanum alkaloid tomatidine 1. The synthesis has been accomplished in 11 steps and 24.9 % overall yield (longest linear sequence). This methodology, which involves a convergent synthon insertion followed by a sequence of ring opening/nitrogen substitution/ring closing, allowed the generation of 1 on > 2 g scale. The synthetic challenge with the diastereoselective generation of the unusual spiroaminoketal moiety was solved through a combined azide reduction/addition sequence. The first diastereoselective synthesis of the phytosteroid yamogenin is also reported. Tomatidine has shown promising antibiotic properties against persistent forms of Staphylococcus aureus (S. aureus) and methicillin-resistant S. aureus (MRSA). In particular, it possesses the unique ability to kill persistent forms of S. aureus and MRSA while simultaneously potentiating the antibiotic efficacy of aminoglycoside antibiotics against wild type strains of the bacteria.
New transformation pathway and cytotoxic derivatives from the acid hydrolysis of timosaponin B III
Zhao, Yun-Fang,Zhang, Yu-Wei,Wang, Yinru,Morris-Natschke, Susan L.,Liu, Wei,Shang, Ting-Ting,Yin, Hong,Lee, Kuo-Hsiung,Huang, Xue-Feng
, p. 2755 - 2761 (2018/11/30)
Timosaponin B III is a major bioactive steroidal saponin isolated from Anemarrhena asphodeloides Bge. To potentially discover derivatives with better biological activity, timosaponin B III was structurally modified via acid hydrolysis to yield one new (2, timopregnane A I) C21 steroidal glycoside and seven known compounds. Their structures were elucidated on the basis of NMR spectroscopy and mass spectrometry. All eight compounds were evaluated for cytotoxic activity against MCF7, SW480, HepG2, and SGC7901 cell lines in vitro. As a result, compounds 6 and 7 showed significant activity (IC50 2.94–12.2 μM) against all tested cell lines. Structure–activity relationships of these compounds were investigated and the preliminary conclusions were provided. Moreover, a new transformation pathway was discovered in the acid hydrolysis of timosaponin B III for the first time.
