77-60-1Relevant academic research and scientific papers
BESHORNIN AND BESHORNOSIDE, STEROIDAL SAPONINS OF BESHORNERIA YUCCOIDES
Kintia, Pavel K.,Bobeyko, Valentin A.,Dragalin, Ivan P.,Shvets, Stepan A.
, p. 1447 - 1449 (1982)
Two new saponins beshornin and beshornoside have been isolated from the methanolic extract of Beshorneria yuccoides leaves and their structures elucidated.Beshornin is 3-O-4)-β-D-glucopyranosyl-(1->2)->-4)-β-D-glucopyranosyl-(1->3)>-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl>-(25R)-5α-spirostan-3β-ol, hereas beshornoside is 3-O-4)-β-D-glycopyranosyl-(1->2)>-4)-β-D-glucopyranosyl-(1->3)>-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl>-26-O--(25R)-5α-furostan-3β,22α,26-triol. - Key Word Index:Beshorneria yuccoides; spirostanol glycosides; furastanol glycosides; beshornin; beshornoside.
BIOLOGICAL ACTIVITIES OF FUROSTANOL SAPONINS FROM NICOTIANA TABACUM
Gruenweller, Sabine,Schroeder, Ernst,Kesselmeier, Juergen
, p. 2485 - 2490 (1990)
Two new furostanol saponins, tobacco saponin A and B were isolated from Nicotiana tabacum seeds.The 26-desgluco derivative of saponin B showed hemolytic and fungicidal activity, whereas the monodesmolide derivative of the minor saponin A had no such effects.Both saponins accumulate during ripening and are degraded during germination of the seeds.They were not found in any other part of the plant.Several Nicotiana species possess the same saponin pattern as recorded for N. tabacum.
Structure of a steroid saponin from Digitalis ciliata
Gvazava,Kikoladze
, p. 162 - 165 (2007)
A new steroid glycoside was isolated from leaves of Digitalis ciliata (Scrophulariaceae) by fractionation of the total extracted substances. Its structure was determined as (25R)-5α-spirostan-3β-ol 3-O-β-D-glucopyranosyl-(1→3)[β-D-fucopyranosyl-(1→2)] -β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside based on chemical transformations, physical constants, and spectral data.
α-Hydroxylation at C-15 and C-16 in Cholesterol: Synthesis of (25R)-5α-Cholesta-3β,15α,26-triol and (25R)-5α-Cholesta- 3β,16α,26-triol from Diosgenin
Williams, John R.,Gong, Hua,Hoff, Nathan,Olubodun, Olaoluwa I.,Carroll, Patrick J.
, p. 269 - 271 (2004)
(Matrix presented) (25R)-5α-Cholesta-3β,16α,26-triol 7b and (25R)-5α-cholesta-3β,15α,26-triol 10b were synthesized, via (25R)-5α-cholesta-3β,16β26-triol 5a, from diosgenin 3 in 52% yield over six steps and 47% yield over eight steps, respectively. An efficient method for inversion of a C-16β hydroxyl to the C-16α position and a short method for transposition of a C-16β hydroxyl to the C-15α position via the unexpected β-reduction of a C-15 ketone in a steroid are reported.
Synthesis and antifungal activity of functionalized 2,3-spirostane isomers
Upadhyay, Sunil Kumar,Creech, Clinton C.,Bowdy, Katharine L.,Stevens, Edwin D.,Jursic, Branko S.,Neumann, Donna M.
, p. 2826 - 2831 (2011)
Invasive fungal infections are a major complication for individuals with compromised immune systems. One of the most significant challenges in the treatment of invasive fungal infections is the increased resistance of many organisms to widely used antifungals, making the development of novel antifungal agents essential. Many naturally occurring products have been found to be effective antimicrobial agents. In particular, saponins with spirostane glycosidic moieties - isolated from plant or marine species - have been shown to possess a range of antimicrobial properties. In this report, we outline a novel approach to the synthesis of a number of functionalized spirostane molecules that can be further used as building blocks for novel spirostane-linked glycosides and present results from the in vitro screenings of the antifungal potential of each derivative against four fungal species, including Candida albicans, Cryptococcus neoformans, Candida glabrata, and the filamentous fungus Aspergillus fumigatus.
Steroidal saponins from Hosta longipes and their inhibitory activity on tumour promoter-induced phospholipid metabolism of HeLa cells
Mimaki, Yoshihiro,Kanmoto, Toshihiro,Kuroda, Minpei,Sashida, Yutaka,Satomi, Yoshiko,Nishino, Atsuko,Nishino, Hoyoku
, p. 1065 - 1070 (1996)
Three new spirostanol saponins and two new furostanol saponins were isolated from the underground parts of Hosta longipes. Their structures were determined to be (25R)-5α-spirostane-2α,3β-diol (gitogenin) 3-O-{O-α-L- rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside}, gitogenin 3-O-{O-α-L- rhamnopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 4)]-β-D- galactopyranoside}, (25R)-5α-spirostan-3β-ol (tigogenin) 3-O-{O-α-L- rhamnopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 4)]-β-D- galactopyranoside}, 26-O-β-D-glucopyranosyl-22-O-methyl-(25R)-5α- furostane-2α,3β,22ξ,26-tetrol 3-O-{O-α-L-rhamnopyranosyl-(1 → 2)-β-D- galactopyranoside} and 26-O-β-D-glucopyranosyl-22-O-methyl-(25R)-5α- furostane-2α,3β,22ε,26-tetrol 3-O-{O-α-L-rhamnopyranosyl-(1 → 2)-O- [β-D-glucopyranosyl-(1 → 4)]-β-D-galactopyranoside}, respectively. The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.
Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells
Fukaya, Haruhiko,Kuroda, Minpei,Matsuo, Yukiko,Mimaki, Yoshihiro,Takatori, Kazuhiro,Tsuchihashi, Hiroko
, (2022/03/27)
The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of s
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.
Steroidal constituents isolated from the seeds of Withania somnifera
Iguchi, Tomoki,Kuroda, Minpei,Ishihara, Mai,Sakagami, Hiroshi,Mimaki, Yoshihiro
supporting information, p. 2205 - 2210 (2019/11/03)
A new withanolide glycoside (1), two new ergostanol glycosides (2 and 3), and a new furostanol glycoside (4), along with nine known steroidal derivatives (5–12) were isolated from the seeds of Withania somnifera. The structures of the new compounds were determined using spectroscopic analysis and hydrolysis. The cytotoxic activities of the isolated compounds were evaluated against Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, and HL-60 human promyelocytic leukemia cells. Only 12 exhibited cytotoxic activity against these cell lines with IC50 values of 0.38, 0.54, and 1.5 μM, respectively.
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.
