Sarsasapogenin, an active ingredient in Rhizoma anemarrhenae, is a promising bioactive lead compound in the treatment of Alzheimer's disease. To search for more efficient anti-Alzheimer agents, a series of novel sarsasapogenin-triazolyl hybrids were designed, synthesized, and evaluated for ...
Cholinergic signalling in the hippocampus may contribute to the aetiology of mood regulation. Antidepressants can reverse the increase in acetylcholinesterase (AChE) activity induced by olfactory bulbectomy. The activation of nicotinic acetylcholine receptors (nAChRs) also alleviates the symptom...
Sarsasapogenin, isolated from rhizomes of Anemarrhena asphodeloides, was found to be able to enhance memory. On the basis of the structure of Sarsasapogenin, a series of derivatives were synthesized and evaluated for their neuroprotective activity in PC12 cells and NO production inhibitory activ...
Based on the fact that Timosaponin A-III, a saponin isolated from the rhizome of Anemarrhena asphodeloides, is a promising bioactive lead compound in the treatment of cancer, structural modification at the C3 and C26 positions of sarsasapogenin has always been the focus of our structure-activity...
Treatment of (25R)-3α-acetoxy-5β-spirostan-23-one with diacetoxyiodobenzene in KOH/MeOH led to F-ring contraction via Favorskii rearrangement.
The development of drugs that attenuate neurodegeneration is important for the treatment of Alzheimer's disease (AD). We previously found that smilagenin (SMI), a steroidal sapogenin from traditional Chinese medicinal herbs improves memory in animal models, is neither a cholinesterase inhib...
Spectroscopic examinatio of purified extracts of the rumen content of sheep intoxicated by Brachiaria decumbens revealed the presence of two spirostanes, identified as epi-sarsasapogenin and epi-smilagenin. Sarsasapogenone was obtained by the oxidation of sarsasapogenin. The reduction of sarsasa...
Tyrosine hydroxylase immunohistochemical analysis revealed that in cultured mesencephalic dopaminergic neurons smilagenin (SMI), added prior to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPP+), protected against the drop of neuron number and neurite outgrowth length caused by MPP+. Addition o...
The purpose of this work is to study the effect of smilagenin on the mRNA stability of muscarinic receptor subtype 1 (M1; m1 mRNA) in aged rat brains and its significance in improving memory. The Y-maze avoidance task showed that oral administration of smilagenin significantly improved spatial m...
The purpose of this paper is to study the effect of smilagenin (SMI) (PYM50028), a sapogenin compound originally identified from Chinese medicinal herb, on dopamine neurons and locomotor ability in aged rats. Experiments were carried out on young and aged Sprague–Dawley rats, which were daily a...
Studies indicated that smilagenin, isolated from Anemarrhena asphodeloides Bunge, could improve cognitive impairment and exhibit neuroprotective activity. On the basis of the structure of smilagenin, a series of derivatives were synthesized and evaluated for their neuroprotective effects of H2O2...
Herein we report a halogenation-ring opening reaction of spiroketals in steroidal sapogenins at room temperature to gain highly valuable ω-halo enol ethers in excellent yields. Boosted by this method, we have prepared solasodine, an antitumor steroidal alkaloid, from diosgenin acetate in three ...
Hairy root cultures of Solanum trilobatum L. were established from leaf explants infected with Agrobacterium rhizogenes strains viz., MTCC 532, MTCC 2364 and ATCC A4. Initially 27 independent root clones were obtained and 5 clones (ST-02, ST-09, ST-11, ST-13 and ST-17) were scrutinized based on ...
In this study, we explored the capacity of the naturally occurring compound solasodine to promote neurogenesis in vitro and in vivo. Mouse embryonic teratocarcinoma P19 cells exposed to solasodine for 2 days followed by a 5-day washout differentiated into cholinergic neurons that expressed speci...
Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the Solanaceae family. A simple and selective liquid chromatography mass spectrometry method for determination of solasodine in rat plasma was developed and validated over the range of 3–1000 ng/mL. Chromatographic se...
Ischemic stroke is the second leading cause of death worldwide. The major limitation of stroke management is the lack of clinically effective therapy. Antioxidants have been demonstrated as potent neuroprotective agents by enhancing the defense mechanism(s), whereas reducing the oxidative stress...
A facile and high-yielding route for the synthesis of solasodine from diosgenin is devised. Ring opening of steroidal spiroketal under mild conditions with trifluoroacetyl trifluoromethanesulfonate (TFAT) provides an applicable protocol to prepare key intermediates 4 or 3-Ac-solasodine, which ca...
Solasodine, a naturally occurring aglycone of glycoalkaloid in eggplant (Solanum melongena), was found to inhibit proliferation in various tumor cells. However, the effect of solasodine on cancer cell metastasis remains unclear. This study investigates the suppression mechanism of solasodine on ...
This article presents new transformations of solasodine – a representative steroid alkaloid sapogenin from the Solanum family. Oxidation of N,O-diacetylated solasodine with either NaNO2/BF3·Et2O or t-BuONO/BF3·Et2O resulted in partial degradation of the side chain to (20S)-3β-acetoxypregn-5-...
Antifungal activity of some natural molecules can be abated or blocked by efflux pumps in Candida albicans, which restricts the discovery of potential antifungal agents. Here we found that the steroidal alkaloid solasodine is active against C. albicans efflux pump-deficient strains but inert tow...
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