“…As it was confirmed by 1D and 2D NMR experiments for 20 and 21 compounds, trityl-group removal under mild acidic condition at room temperature resulted in additional spiroketal ring opening. Our results were consistent with those known from the literature [ 13 , 31 , 32 ], where diosgenyl and tigogenin analogs with opened F-ring exhibited high biological activity [ 13 , 31 , 32 ]. Therefore, we decided to include these two derivatives ( 20 and 21 ) into further investigation as well.…”
Section: Resultssupporting
confidence: 93%
“…In the present study, an efficient method of thiol-group introduction to the structure of common natural products and synthetic active compounds with recognized biological efficacy such as: genistein ( 1 ), 5,11-dimethyl-5 H -indolo[2,3-b]quinolin ( 2 ), capecitabine ( 3 ), diosgenin ( 4 ), tigogenin ( 5 ), flumethasone ( 6 ), fluticasone propionate ( 7 ), ursolic acid methyl ester ( 8 ), and β-sitosterol ( 9 ) was developed ( Figure 1 ). According to the literature, compounds 1 – 9 and their respective derivatives show anticancer [ 11 , 12 , 13 ], antibacterial [ 14 ], antifungal [ 15 ], and anti-inflammatory [ 13 , 15 , 16 ] activities. Some of them are widely used in therapy as the registered drugs: flumethasone [ 17 ], fluticasone propionate [ 18 ], and capecitabine [ 19 , 20 ].…”
An efficient method of thiol group introduction to the structure of common natural products and synthetic active compounds with recognized biological efficacy such genistein (1), 5,11-dimethyl-5H-indolo[2,3-b]quinolin (2), capecitabine (3), diosgenin (4), tigogenin (5), flumethasone (6), fluticasone propionate (7), ursolic acid methyl ester (8), and β-sitosterol (9) was developed. In most cases, the desired compounds were obtained easily via two-step processes involving esterification reaction employing S-trityl protected thioacetic acid and the corresponding hydoxy-derivative, followed by removal of the trityl-protecting group to obtain the final compounds. The results of our preliminary experiments forced us to change the strategy in the case of genistein (1), and the derivatization of diosgenin (4), tigogenin (5), and capecitabine (3) resulted in obtaining different compounds from those designed. Nevertheless, in all above cases we were able to obtain thiol-containing derivatives of selected biological active compounds. Moreover, a modelling study for the two-step thiolation of genistein and some of its derivatives was accomplished using the density functional theory (B3LP). A hypothesis on a possible reason for the unsuccessful deprotection of the thiolated genistein is also presented based on the semiempirical (PM7) calculations. The developed methodology gives access to new sulphur derivatives, which might find a potential therapeutic benefit.
“…As it was confirmed by 1D and 2D NMR experiments for 20 and 21 compounds, trityl-group removal under mild acidic condition at room temperature resulted in additional spiroketal ring opening. Our results were consistent with those known from the literature [ 13 , 31 , 32 ], where diosgenyl and tigogenin analogs with opened F-ring exhibited high biological activity [ 13 , 31 , 32 ]. Therefore, we decided to include these two derivatives ( 20 and 21 ) into further investigation as well.…”
Section: Resultssupporting
confidence: 93%
“…In the present study, an efficient method of thiol-group introduction to the structure of common natural products and synthetic active compounds with recognized biological efficacy such as: genistein ( 1 ), 5,11-dimethyl-5 H -indolo[2,3-b]quinolin ( 2 ), capecitabine ( 3 ), diosgenin ( 4 ), tigogenin ( 5 ), flumethasone ( 6 ), fluticasone propionate ( 7 ), ursolic acid methyl ester ( 8 ), and β-sitosterol ( 9 ) was developed ( Figure 1 ). According to the literature, compounds 1 – 9 and their respective derivatives show anticancer [ 11 , 12 , 13 ], antibacterial [ 14 ], antifungal [ 15 ], and anti-inflammatory [ 13 , 15 , 16 ] activities. Some of them are widely used in therapy as the registered drugs: flumethasone [ 17 ], fluticasone propionate [ 18 ], and capecitabine [ 19 , 20 ].…”
An efficient method of thiol group introduction to the structure of common natural products and synthetic active compounds with recognized biological efficacy such genistein (1), 5,11-dimethyl-5H-indolo[2,3-b]quinolin (2), capecitabine (3), diosgenin (4), tigogenin (5), flumethasone (6), fluticasone propionate (7), ursolic acid methyl ester (8), and β-sitosterol (9) was developed. In most cases, the desired compounds were obtained easily via two-step processes involving esterification reaction employing S-trityl protected thioacetic acid and the corresponding hydoxy-derivative, followed by removal of the trityl-protecting group to obtain the final compounds. The results of our preliminary experiments forced us to change the strategy in the case of genistein (1), and the derivatization of diosgenin (4), tigogenin (5), and capecitabine (3) resulted in obtaining different compounds from those designed. Nevertheless, in all above cases we were able to obtain thiol-containing derivatives of selected biological active compounds. Moreover, a modelling study for the two-step thiolation of genistein and some of its derivatives was accomplished using the density functional theory (B3LP). A hypothesis on a possible reason for the unsuccessful deprotection of the thiolated genistein is also presented based on the semiempirical (PM7) calculations. The developed methodology gives access to new sulphur derivatives, which might find a potential therapeutic benefit.
“…A set of diosgenin compounds should be considered as a promising scaffold for their abilities as anticancer and immunomodulatory agents. [87,88] Hepatoprotective effects a. Administration of diosgenin may lead to reduction of liver injury indices and oxidative stress and inflammatory events.…”
Section: Health Benefits Key Points Referencementioning
Background
Diosgenin is an isospirostane derivative, which is a steroidal sapogenin and the product of acids or enzymes hydrolysis process of dioscin and protodioscin. Galactomannans are heteropolysaccharides composed of D-mannose and D-galactose, which are major sources of locust bean, guar, tara and fenugreek.
Methods
Literature survey was accomplished using multiple databases including PubMed, Science Direct, ISI web of knowledge and Google Scholar.
Results
Four major sources of seed galactomannans are locust bean (Ceratonia siliqua), guar (Cyamopsis tetragonoloba), tara (Caesalpinia spinosa Kuntze), and fenugreek (T.foenum-graecum). Diosgenin has effect on immune system, lipid system, inflammatory and reproductive systems, caner, metabolic process, blood system, blood glucose and calcium regulation. The most important pharmacological benefits of galactomannan are antidiabetic, antioxidant, anticancer, anticholinesterase, antiviral activities, and appropriate for dengue virus and gastric diseases.
Conclusions
Considering the importance of diosgenin and galactomannans, the obtained findings suggest potential of diosgenin and galactomannans as natural products in pharmaceutical industries.
“…Diosgenin can be used as the natural precursor to commercially synthesize most of the therapeutically useful steroidal drugs, including estrogen, progesterone, testosterone, and other sex hormones or corticosteroids [ 12 ]. However, in addition to this high synthetic relevance, diosgenin itself has the benefits of antiproliferative activity [ 13 ], ameliorates testicular damage [ 14 ], anticancer activity [ 15 , 16 ], anti-apoptotic effect [ 17 ], cardiovascular protective effect [ 18 , 19 ], immunomodulating activity [ 20 ], among others. Scheme 1 Chemical structures of diosgenin (DSG) and piperazine (PIP) …”
A cocrystal of diosgenin with piperazine in 2:1 stoichiometry was successfully synthesized. The solid form was prepared by liquid assisted grinding, slurry and crystallization methods. The cocrystal was characterized by powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared spectroscopy, and structure determined by single crystal X-ray diffraction, the hydrogen bonds formed into fish bone structure along the [010] direction and all the molecules packed into 3D layer structure along a axis. After formation of cocrystal, the solubility of diosgenin was improved, and the solubility value in 0.2% SDS solution was approximately 1.5 times as large as that of the parent material.
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