126-18-1Relevant articles and documents
Structures of toxic steroidal saponins from Narthecium asiaticum MAXIM.
Inoue,Mimaki,Sashida,Kobayashi
, p. 1162 - 1166 (1995)
The full structures of the two steroidal saponins from Narthecium asiaticum MAXIM, we previously identified as toxic substances by monitoring the toxicity in guinea pigs were phytochemically reinvestigation on the aerial parts of the plant. The desired toxic saponins (6, 7) were isolated together with two known lignan glucosides (1, 2), a known flavonoid glucoside (3), a new furanone glucoside (4), a known steroidal saponin (5) and a new steroidal saponin (8). The structures of the new furanone glucoside, toxic saponins and new saponin were determined on the basis of spectroscopic data and acid- or enzymatic-catalyzed hydrolysis to be (S)-5-β-D- glucopyranosyloxy-4-methoxyfuran-2(5H)-one (4), (25R,S)-5β-spirostan-3β-ol 3-O-{O-β-D-glucopyranosyl-(1→2)-O-[α-L-arabinopyranosyl-(1→3)]-β-D- galactopyranoside} (6), (25R,S)-5β-spirostan-3β-ol 3-O-{O-β-D- glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranoside} (7) and (24S,25R)-5β-spirostane-3β,24-diol 3-O-{O-β-D-glucopyranosyl- (1→2)-O-[α-1-arabinopyranosyl-(1→3)]-β-D-galactopyranoside} (8), respectively.
Steroidal glycosides from Agave utahensis and their cytotoxic activity
Yokosuka, Akihito,Jitsuno, Maki,Yui, Satoru,Yamazaki, Masatoshi,Mimaki, Yoshihiro
, p. 1399 - 1404 (2009)
Eight new spirostanol saponins (1-8) and three new furostanol saponins (9-11) were isolated from the whole plants of Agave utahensis. The structures of 1-11 were determined by analysis of extensive spectroscopic data. The saponins were evaluated for their
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.
Steroidal saponins from the stem of Yucca elephantipes
Zhang, Ying,Zhang, Ying-Jun,Jacob, Melissa R.,Li, Xing-Cong,Yang, Chong-Ren
, p. 264 - 270 (2008)
Ten steroidal saponins with cis-fused A/B ring, including a smilagenin glycoside, elephanoside A (4), and the five furostanol bisdesmosides, elephanosides B-F (6-10), were isolated from the stems of Yucca elephantipes Regel. (Agavaceae). Their structures were determined by detailed chemical and spectroscopic analysis. All the isolated compounds were tested for their in vitro antifungal and antibacterial activities. Only the two known spirostanol glycosides Ys-II (1) and Ys-IV (2) showed moderate inhibitory activity against the growth of Candida albicans and Cryptococcus neoformans.
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.
Diosgenin derivatives, and pharmaceutical compositions thereof and application thereof
-
Paragraph 0108-0110; 0113, (2019/01/24)
The invention relates to diosgenin derivatives. The structural formula of the diosgenin derivatives is as shown in a general formula (1) which is described in the specification. The invention also provides pharmaceutical compositions of the diosgenin derivatives and application thereof. According to the invention, systematic structural modification directed at double bonds at position 3 and position 5/6 of a lead compound is performed for the first time so as to synthesize a series of novel compounds; and the results of activity tests of the novel compounds at related targets show that most ofthe novel compounds have better activity than the activity of the lead compound and are very valuable for the treatment of neurodegenerative diseases. Thus, the diosgenin derivatives overcome defectsof conventional diosgenin derivatives and have important significance.
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.
TIMOSAPONIN COMPOUNDS
-
Paragraph 00250, (2013/10/22)
Provided herein are timosaponin compounds of Frmula I, II, IIΙ, I', II' and IIΙ', pharmaceutical compositions comprising the coumpounds, and processes of preparation thereof. Also provided are uses of said timosaponin compounds for preparing medicament for the treatment of diseases associated with beta-amyloid in hosts or subjects in need thereof.
