126-18-1Relevant articles and documents
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Wall et al.
, p. 3086,3088 (1955)
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Steroid compounds from stems of yucca gloriosa
Benidze,Skhirtladze,Kemertelidze
, p. 518 - 519 (2012)
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THE STEROIDAL GLYCOSIDES FROM THE CAUDEX OF YUCCA GLORIOSA
Nakano, Kimiko,Yamasaki, Tokushi,Imamura, Yukiko,Murakami, Kotaro,Takaishi, Yoshihisa,Tomimatsu, Toshiaki
, p. 1215 - 1218 (1989)
Five steroidal glycosides were isolated from the fresh caudex of Yucca gloriosa together with YG-1 and Ps-1 previously obtained from flowers and the structures of these glycosides were established to be smilagenin 3-O-β-D-glycopyranosyl-(1->2)-β-D-glucopyranoside (Ys-I), 3-O-β-D-glucopyranosyl-(1->2)-β-D-galactopyranoside (YS-II), 3-O-β-D-glucopyranosyl-(1->2)-3)>-β-D-glucopyranoside (YS-III), 3-O-β-D-glucopyranosyl-(1->2)-3)>-β-D-galactopyranoside (YS-IV) and samogenin 3-O-β-D-glucopyranosyl-(1->2)-β-D-galactopyranoside (YS-V), respectively.Key Word Index - Yucca gloriosa; Agavaceae; steroidal saponins; smilagenin glycosides; samogenin glycoside.
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.
Steroidal Saponins from Furcraea hexapetala Leaves and Their Phytotoxic Activity
Calle, Juan M.,Pérez, Andy J.,Simonet, Ana M.,Guerra, José O.,Macías, Francisco A.
, p. 2903 - 2911 (2016/12/07)
Four new steroidal saponins (1-4) along with 13 known saponins were isolated from the leaves of Furcraea hexapetala. The new compounds were identified as (20R,22R,25R)-3β-hydroxy-5α-spirostan-12-one 3-O-{α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (1), (25R)-3β-hydroxy-5α-spirost-20(21)-en-12-one 3-O-{α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (2), (25R)-5α-spirostan-3β-ol 3-O-{β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (3), and (25R)-5β-spirostan-3β-ol 3-O-{β-d-glucopyranosyl-(1→6)-O-β-d-galactopyranoside} (4) by spectroscopic analysis, including one- and two-dimensional NMR techniques, mass spectrometry, and chemical methods. The phytotoxicity of the isolated compounds against the standard target species Lactuca sativa was evaluated. Structure-activity relationships for these compounds with respect to phytotoxic effects are discussed.
