6786-76-1

Usage

InChI:InChI=1/C7H14O4/c1-5(9)7(10)6(11-2)3-4-8/h4-7,9-10H,3H2,1-2H3/t5-,6-,7-/m1/s1

Upstream product

• 1173896-51-9 syriacoside T 
• 1159579-91-5 hoodigoside W 
• 1159579-93-7 calogenin 20-O-β-D-glucopyranosyl-3-O-β-D-thevetopyranosyl-(1->4)-β-D-oleandropyranoside 
• 1206547-23-0 (3β,12β,14β,17α)-3-{[2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-12-{[(2E)-3-phenylprop-2-enoyl]oxy}pregn-5-en-20-yl 3-methylbutanoate 
• 1206547-24-1 (3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl 4-hydroxybenzoate 
• 1206547-25-2 (3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl 4-hydroxybenzoate 
• 1206547-26-3 (3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl 4-hydroxybenzoate 

Downstream Products

• 105274-10-0 methyl α-D-cymarofuranoside 3,5-dinitrophenylcarbamate 
• 105274-07-5 methyl β-D-cymaropyranoside 3,5-dinitrophenylcarbamate 
• 105274-06-4 methyl α-D-cymaropyranoside 3,5-dinitrophenylcarbamate 
• 105274-08-6 methyl α-L-cymaropyranoside 3,5-dinitrophenylcarbamate 
• 105274-09-7 methyl β-L-cymaropyranoside 3,5-dinitrophenylcarbamate 
• 76234-95-2 methyl α-cymarofuranoside 
• 76234-95-2 methyl β-cymarofuranoside 
• 4166-79-4 methyl β-cymaropyranoside 
• 4166-79-4 methyl α-cymaropyranoside 

Relevant academic research and scientific papers

Pregnane glycosides from Gymnema inodorum and their α-glucosidase inhibitory activity

Two new pregnane glycosides, gyminosides A and B (1 and 2) and three known, tinctoroside B (3), tinctoroside C (4), and gymnepregoside F (5) were isolated from the leaves of Gymnema inodorum (Lour.) Decne. Their structures were elucidated by physical and chemical methods and comparing with those reported in the literature. All these compounds were evaluated for α-glucosidase assay. Compound 5 exhibited the most anti α-glucosidase activity with inhibitory percentage of 63.7 ± 3.9% at the concentration of 200 μM. Compounds 1–4 showed moderate anti α-glucosidase activity with inhibitory percentage ranging from 40.0 to 52.1%.

New C21 steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury

Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C21 steroidal glycosides (1–4) and one known compound stauntoside F (5). Their chemical structures were characterized by sophisticated analyses of IR, HR

Cytotoxic and apoptosis-inducing activity of C21 steroids from the roots of Cynanchum atratum

Two new (1–2) and two known C21 steroids (3–4) were isolated from the roots of Cynanchum atratum. Their structures were elucidated by detailed 1D and 2D spectroscopic. The MTT assay showed that compounds 1–4 displayed obvious cytotoxic activities against HepG2 cells with IC50 values ranging from 10.19?μM to 76.12?μM. Compounds 1–3 also exhibited cytotoxic effects in A549 cells with IC50 values of 30.87–95.39?μM. Compound 3 showed the antiproliferative activity via G0/G1 cell cycle arrest and proapoptosis in HepG2 cells by Flowcytometry analysis. Western blotting analysis revealed that compound 3 could induce HepG2 cell apoptosis via the mitochondrial pathway by downregulating Bcl-2 expression, upregulating Bax protein expression, and activating caspase-9 and caspase-3.

New Sweet-Tasting C21-Pregnane Glycosides from Pericarps of Myriopteron extensum

Ten novel C21 pregnane glycosides, extensumside C-L (1-10), were isolated as highly sweet-tasting substances from the edible pericarps of Myriopteron extensum (Wight) K. Schum by sensory-guided fractionation and purification. Their structures were determined through 1D and 2D NMR, such as HSQC, HMBC, 1H-1H COSY, HSQC-TOCSY, and ROESY, as well as other spectroscopic analysis combined with chemical evidence. These compounds shared the same aglycone, 3β,16α-dihydroxy-pregn-5-en-20-one, and contained the deoxysugar chain and the glucose chain which were linked to C-3 and C-16 of the aglycone, respectively. The sweetness potency was evaluated by a human sensory panel test and preliminary structure-taste relationship was discussed. The sweetness intensities of these compounds are between 50 and 400 times greater than that of sucrose. Furthermore, quantitation analyses of compounds 1, 3, 4, and 6 in different parts of M. extensum indicated that the concentrations of these sweet components in the pericarps are obviously higher than those in stems and roots.

Identification and Evaluation of Antiepileptic Activity of C21 Steroidal Glycosides from the Roots of Cynanchum wilfordii

Nine new C21 steroidal glycosides, named cynawilfosides A-I (1-9), along with 12 known compounds were isolated from the roots of Cynanchum wilfordii. The structures of the new compounds were elucidated by spectroscopic analysis and chemical methods. The five major components, cynawilfoside A (1), cynauricoside A (11), wilfoside C1N (16), wilfoside K1N (17), and cyanoauriculoside G (18), exhibited significant protection activity in a maximal electroshock (MES)-induced mouse seizure model with ED50 values of 48.5, 95.3, 124.1, 72.3, and 88.1 mg/kg, respectively.

C21 steroidal glycosides from the roots of Cynanchum paniculatum

As a part of our continuing research for bioactive constituents from Cynanchum plants, four new C21 steroidal glycosides, cynapanoside D-G (1–4), together with six known compounds (5–10) were isolated from the roots of Cynanchum paniculatum (Bge.) Kitag. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. Compound 8 exhibited potent inhibitory activities against HL-60, HT-29, PC-3 and MCF-7 cell lines with IC50 values of 8.3, 7.5, 34.3 and 19.4?μM, respectively and compounds 1–4 and 9 displayed moderate cytotoxicity against the four cell lines. The in vitro antioxidant activities of compounds 1–4, 8 and 9 were assayed by DPPH radical scavenging activity. Antibacterial and antifungal activities of compounds 1–4, 8 and 9 were also tested.

Two new steroidal glycosides from Cynanchum wallichii

Two new C21 steroidal glycosides were isolated from Cynanchum wallichii Wight. Their structures were elucidated as caudatin-3-O-β-d-glucopyranosyl- (1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (1) and caudatin-3

Nine new steroidal glycosides from the roots of Cynanchum stauntonii

Nine new steroidal glycosides, named as stauntosides C-K (2, 5, 7-10, 13, 14, and 16), along with seven known compounds (1, 3, 4, 6, 11, 12, and 15) were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR, and HRESI-MS, and qualitative chemical methods. Their significance in terms of the chemotaxonomy of C. stauntonii is discussed.

Five new pregnane glycosides from the stems of Marsdenia tenacissima

Activity-guided fractionation of the stems of Marsdenia tenacissima led to the isolation of five new pregnane glycosides, namely marstenacissides E (1), F (2), G (3), H (4), and I (5). Their structures were determined on the basis of 1H and 13C NMR, COSY, TOCSY, ROESY, and FABMS experiments.

A new pregnane glycoside and oligosaccharide from Parabarium huaitingii

Two new compounds, along with two known compounds, were isolated from the barks of Parabarium huaitingii, and their structures were determined as 5α-pregn-6-ene-3β,17α,20(S)-triol-20-O-β-D- digitoxopyranoside (1), cymaropyranurolactone 4-O-β-D-digitalopyranosyl-(1 → 4)-O-β-D-cymaropyranosyl-(1 → 4)-O-β-D-oleandropyranosyl-( 1 → 4)-O-β-D-cymaropyranoside (2), 3β,17α,20(S)- trihydroxy-5α-pregn-6-ene (3), and 5a-pregn-6-ene-3β,17α,20(S)- triol-3-O-β-D-digitalopyranoside (4) by spectroscopic methods.