874485-32-2

Usage

Uses

Used in Pharmaceutical Industry:
(25RS)-Ruscogenin is used as a therapeutic agent for its potent anti-inflammatory and anti-thrombotic effects. It can be employed in the development of medications targeting inflammatory conditions and promoting cardiovascular health.
Used in Cardiovascular Applications:
(25RS)-Ruscogenin is used as a cardioprotective agent for its ability to prevent blood clot formation and reduce inflammation in the cardiovascular system. This makes it a promising candidate for the treatment of conditions such as atherosclerosis, deep vein thrombosis, and other thrombotic disorders.
Used in Anti-inflammatory Applications:
(25RS)-Ruscogenin is used as an anti-inflammatory agent to alleviate symptoms associated with various inflammatory diseases, such as arthritis, asthma, and inflammatory bowel disease. Its ability to modulate inflammatory pathways and reduce the production of pro-inflammatory mediators makes it a valuable component in the development of anti-inflammatory drugs.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic efficacy of (25RS)-Ruscogenin, researchers are exploring the use of drug delivery systems, such as nanoparticles and liposomes, to encapsulate and protect the compound. This approach can improve its stability, solubility, and targeted delivery to specific tissues or cells, thereby maximizing its therapeutic potential.

Upstream product

• 17676-33-4 spirosta-5(6),25(27)-diene-1β,3β-diol 
• 14414-62-1 spirost-5-ene-1-oxo-3β-ol 
• 38971-41-4 ophiopogonin B 
• 90802-64-5 3β-acetoxyspirost-5-ene-1-one 
• 201858-23-3 3β-O-tert-butyldimethylsilyl-(25R)-ruscogenin 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 35882-30-5 25(S) ruscogenin 
• 144028-91-1 25(S) ruscogenin 1-O-β-D-glucopyranoside 
• 201858-25-5 (20S,22R,25R)-1α,2α-epoxyspirosta-4,6-dien-3-one 
• 512-04-9 diosgenin 
• 1072072-38-8 (25R)-1α-hydroxyspirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1->2)-[O-α-L-rhamnopyranosyl(1->4)]-β-D-glucopyranoside 
• 87436-70-2 ruscogenin 3-O-α-L-rhamnopyranoside 
• 87436-70-2 25(S)-ruscogenin 3-O-L-rhamnopyranoside 

Downstream Products

• 79037-13-1 1β,3β-dibenzoyloxycholest-5-ene-16β-ol 
• 79037-12-0 C₄₂H₅₆O₇S 
• 79037-04-0 1β,3β,16β-tribenzoyloxycholest-5-ene 
• 79037-07-3 1β,3β,16β,26-tetrabenzoyloxycholest-5-ene 
• 79037-17-5 (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene 

Relevant academic research and scientific papers

Steroidal glycosides from the underground parts of Dracaena thalioides and their cytotoxic activity

Six spirostanol glycosides (1-6) and 12 known compounds (7-18) were isolated from the underground parts of Dracaena thalioides (Agavaceae). Their structures were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and chemical transformations. The isolated compounds were evaluated for cytotoxic activity against HL-60 human leukemia cells. Compounds 1, 3-6, and 8-18 showed cytotoxicity against HL-60 cells, of which 10, a bisdesmosidic spirostanol derivative, showed potent cytotoxicity against HL-60 cells with an IC50 value of 0.38 μM and induced apoptosis in HL-60 cells.

Three new neuritogenic steroidal saponins from Ophiopogon japonicus (Thunb.) Ker-Gawl

Three new steroidal saponins (1-3) and a known saponin (4) were isolated from Ophiopogon japonicus (Thunb.) Ker-Gawl. Their structures were determined by spectroscopic analyses and chemical derivatization. The isolated compounds (1-4) were potent inducers of neuritogenesis on PC12 cells. Compound 1 showed the highest neuritogenic activity of 46% at 1 μM. The study of structure-activity relationships suggests that aglycone is important for the neuritogenic activity of the compounds. Specific inhibitor experiments and Western blot analysis suggest that 1-induced neuritogenic activity depends on the activation of mitogen-activated protein kinase kinase (MEK)/extracellular signal regulated kinase (ERK) signaling pathway on PC12 cells.

New neuritogenic steroidal saponin from Ophiopogon japonicus (Thunb.) Ker-Gawl

A new steroidal saponin was isolated from Ophiopogon japonicus. This saponin possesses a modification by 2-hydroxy-3-methylvalerylation of the hydroxyl group at C-4' of the sugar, linked to C-1 of the aglycone. It exhibited significant neuritogenic activity for PC12 cells. The structure-activity relationship revealed the aglycone, rather than the sugar moieties and acylation, to be important for the neuritogenic activity.

Steroidal glycosides from Ruscus ponticus

A comparative metabolite profiling of the underground parts and leaves of Ruscus ponticus was obtained by an HPLC-ESIMSn method, based on high-performance liquid chromatography coupled to electrospray positive ionization multistage ion trap mass spectrometry. The careful study of HPLC-ESIMSn fragmentation pattern of each chromatographic peak, in particular the identification of diagnostic product ions, allowed us to get a rapid screening of saponins belonging to different classes, such as dehydrated/or not furostanol, spirostanol and pregnane glycosides, and to promptly highlight similarities and differences between the two plant parts. This approach, followed by isolation and structure elucidation by 1D- and 2D-NMR experiments, led to the identification of eleven saponins from the underground parts, of which two dehydrated furostanol glycosides and one new vespertilin derivative, and nine saponins from R. ponticus leaves, never reported previously. The achieved results highlighted a clean prevalence of furostanol glycoside derivatives in R. ponticus leaves rather in the underground parts of the plant, which showed a wider structure variety. In particular, the occurrence of dehydrated furostanol derivatives, for the first time isolated from a Ruscus species, is an unusual finding which makes unique the saponins profile of R. ponticus.

Highly efficient and regio-selective glucosylation of 25(S) ruscogenin by Gliocladium deliquescens NRRL1086

A new steroidal glycoside, 25(S) ruscogenin 1-O-β-D-glucopyranoside (2) was obtained through the microbial transformation of 25(S) ruscogenin (1) by G. deliquescens NRRL1086 in 54% isolated yield. The structure of the product was elucidated by IR, MS and NMR spectra. This is the first report on the preparation of steroidal saponins by microbial transformation.

New steroidal glycosides from rhizomes of Clintonia udensis

A total of 10 steroidal glycosides, together with three new spirostanol glycosides (6-8), a new furostanol glycoside (9), and a new cholestane glycoside (10), were isolated from the rhizomes of Clintonia udensis (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including 2-D nuclear magnetic resonance (NMR) data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. The isolated glycosides were evaluated for their cytotoxic activity against HL-60 leukemia cells. Spirostanol glycosides 1 and 2, and furostanol glycoside 4 showed cytotoxic activity with IC50 values of 3:2 ± 0:02, 2:2 ± 0:12, and 2:2 ± 0:06 μg/ml, respectively. Neither the spirostanol and furostanol saponins with a hydroxy group at C-1 (6 and 9) and C-12 (7 and 8) nor cholestane glycosides (5 and 10) exhibited apparent cytotoxic activity at a sample concentration of 10μg/ml.

Preparations of vitamin D analogs, spirostanols and furostanols from diosgenin and their cytotoxic activities

Vitamin D analogs 12 and 13 having a spiro ring in the side chain, various spirostanols 18-21, 26, 27, 29 and 37, and furostanols 34-36 having SCN and SeCN groups at the 26 position were prepared from diosgenin 1 via (20S,22R,25R)-spirost-1α,2α-epoxy-4,6-

Polyhydroxylated steroidal constituents from the fresh rhizomes of Tupistra yunnanensis

Six new polyhydroxylated steroidal saponins, tupistrosides A-F (1-6), together with nine known steroids, were isolated from the fresh rhizomes of Tupistra yunnanensis. Their structures were elucidated to be (25S)-1β,4β,5β-trihydroxy-spirostane-3β-yl O-α-l-arabinopyranoside (1), 1β,24β-dihydroxy-spirost-5,25(27)- dien-3α-yl O-β-d-glucopyranoside (2), (22S,25S)-1α,2β, 3α,5α-tetrahydroxy-furo-spirostane-26-yl O-β-d-glucopyranoside (3), 1β,3α,22 ξ-trihydroxy-furost-5,25(27)-dien-26-yl O-β-d-glucopyranoside (4), 26-O-β-d-glucopyranosyl-1β,22- dihydroxy-furost-5-en-3α-yl O-β-d-glucopyranoside (5) and 22-methoxy-1β,2β,3β,4β,5β,7α-hexahydroxy-furost- 25(27)-en-6-one-26-yl O-β-d-glucopyranoside (6), respectively, by means of spectroscopic analysis and the results of acid hydrolysis.

Steroidal glycosides from the bulbs of Ornithogalum thyrsoides

Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.

Synthesis of (25R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)- [β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside

The synthesis of (25R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)- [β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, a saponin from the tuber of Liriope muscari (Decne.) Bailey, is described.