13089-76-4

Basic information

• Product Name: D-symarose
• Synonyms: D-symarose
• CAS NO: 13089-76-4
• Molecular Weight: 162.186
• Mol File: 13089-76-4.mol
• Article Data: 33

Chemical Properties

• CAS DataBase Reference: D-symarose(CAS DataBase Reference)
• NIST Chemistry Reference: D-symarose(13089-76-4)
• EPA Substance Registry System: D-symarose(13089-76-4)

Safety Data

• Hazardous Substances Data: 13089-76-4(Hazardous Substances Data)

Upstream product

• 1395707-76-2 C₃₅H₆₀O₁₇ 
• 97399-97-8 cynantratoside-B 
• 1186628-87-4 qingyangshengenin 3-O-β-D-oleandropyanosyl-(1→4)-β-D-digitoxopyranoside 
• 1417887-96-7 stauntogenin B 3-O-α-L-cymaropyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-thevetopyranoside 
• 1417887-93-4 stauntogenin 3-O-α-L-diginopyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-thevetopyranoside 
• 1417887-95-6 stauntogenin A 3-O-α-L-diginopyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-cymaropyranosoyl-(1→4)-β-D-thevetopyranoside 
• 1417887-94-5 stauntogenin 3-O-α-L-cymaropyranosoyl-(1→4)-β-D-digitoxopyranosoyl-(1→4)-β-D-cymaropyranoside 

Downstream Products

• 75-07-0 acetaldehyde 
• 142-73-4 iminodiacetic acid 
• 76234-95-2 methyl α-cymarofuranoside 
• 76234-95-2 methyl β-cymarofuranoside 
• 4166-79-4 methyl β-cymaropyranoside 
• 4166-79-4 methyl α-cymaropyranoside 
• 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 
• 105274-10-0 methyl α-D-cymarofuranoside 3,5-dinitrophenylcarbamate 
• 67968-33-6 methyl β-D-cymaropyranoside 
• 76234-95-2 methyl α-D-cymarofuranoside 
• 76234-96-3 methyl β-D-cymarofuranoside 

Relevant articles and documents

Steroidal glycosides from the roots of Cynanchum stauntonii and their effects on the expression of iNOS and COX-2

Six new steroidal glycosides, named stauntosides O-T (1-6), along with eight known compounds (7-14), were obtained from the 95% aqueous ethanol extract of the roots of Cynanchum stauntonii. Their chemical structures were elucidated by IR, HR ESI-MS/MS, 1H- and 13C NMR, 1H-1H COSY, HSQC, HSQC-TOCSY, and HMBC spectroscopic analyses, which showed interesting 13,14:14,15-disecopregnane-type or 14,15-secopregnane-type C21 steroidal glycosides. The glycosides' anti-inflammatory effects were investigated by detecting the inhibitory effects of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) on RAW246.7 murine macrophage cells stimulated by lipopolysaccharide (LPS). Our results showed that compounds 1, 5, 8, 9, 11, and 13 could significantly inhibit iNOS expression, and compounds 5 and 7 could clearly reduce COX-2 expression in RAW246.7 cells stimulated by LPS compared to cells stimulated with LPS and not treated with other compounds. Thus, compounds 1, 5, 7-9, 11, and 13 have the potential to mediate anti-inflammatory effects, with compound 5 having a greater anti-inflammatory effect than the other compounds.

Cytotoxic Pregnane Steroidal Glycosides from Chonemorpha megacalyx

Three new C21 pregnane steroids, chonemorphols A-C (1, 3, and 4), 11 new C21 steroidal glycosides, chonemorphosides A-K (2 and 5-14), and 11 known compounds (15-25) were obtained from the vines and leaves of Chonemorpha megacalyx Pierre. Their structures were established using extensive spectroscopic data. The X-ray crystallographic data of 1 and 3 permitted definition of their absolute configurations. Notably, 1 and 2 possessed an uncommon 6/5/6/5/5-fused steroidal ring system. Compound 7 displayed significant cytotoxicity against several cancer cell lines with IC50 values of 2.0-3.6 μM.

Minor cytotoxic cardenolide glycosides from the root of Streptocaulon juventas

In order to determine new minor natural cardenolide glycosides as cytotoxic candidates, we isolated six new cardenolide glycosides together with four known ones, which had never previously been reported in the genus, by bioassay-guided separation from the 75% ethanol extract of Streptocaulon juventas (Asclepiadaceae). Their structures were elucidated on the basis of spectroscopic analysis, including homo- and heteronuclear correlation NMR experiments (COSY, HSQC and HMBC). The cytotoxic activities of these compounds were evaluated against A549 and NCI-H460 cell lines by MTT assay and compound 7 exhibited inhibitory activity against the two cell lines, while other compounds displayed a range of inhibitory activity against NCI-H460 and A549 cells. Their structure-activity relationships were also discussed.

Pregnane glycosides from Dregea volubilis and their α-glucosidase inhibitory activity

Three new pregnane glycosides namely volubilosides D-F (1–3) along with three known, dregeoside Da1 (4), volubiloside A (5), and drevoluoside N (6) were isolated from the methanol extract of the leaves of Dregea volubilis using combined chromatographic methods. Their structures were elucidated by 1D-, 2D-NMR, and HR-ESI-MS spectra and comparing with those reported in the literature. Compounds 5 and 6 showed the most significant α-glucosidase inhibitory activity at the concentration of 40 μM with inhibition of 51.3 ± 3.2% and 50.4 ± 3.1%, respectively, compared to acarbose (59.8 ± 1.6%).

Appetite suppressing pregnane glycosides from the roots of Cynanchum auriculatum

In the search for plant alternatives to Hoodia gordonii containing P57, a pregnane glycoside with potential appetite suppressant effect, the roots of Cynanchum auriculatum were investigated. As a result, 15 pregnane glycosides including nine never previously reported were isolated. Their structures were elucidated on the basis of extensive spectroscopic analyses and chemical methods. Appetite suppressant effect and body weight loss were observed when tested with the most abundant pregnane glycoside, wilfoside K1N, in an in vivo test with rats.

Four new pregnane glycosides from Gymnema latifolium and their α-glucosidase and α-amylase inhibitory activities

Four new pregnane glycosides, gymlatifosides A - D (1 ? 4) and one known pregnane glycoside, verticilloside J (5) were isolated from the leaves of Gymnema latifolium Wall. ex Wight. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR, HR-ESI-MS, and in comparison with the reported data. All these compounds were tested for α-glucosidase and α-amylase inhibitory activities. Compound 5 exhibited the most anti α-glucosidase activity with inhibitory percentage of 37.8 ± 1.5% at the concentration of 200 μM. Compounds 1–4 showed moderate anti α-glucosidase activity with inhibitory percentage ranging from 7.0 to 30.1%. In addition, all compounds 1–5 showed moderate/weak anti α-amylase activity in the investigated test.

New calogenin pregnane glycoside derivative from Huernia saudi- arabica and its Lipase and α-Glucosidase Inhibitory Activities

As ongoing investigation of Huernia saudi-arabica D.V.Field (Asclepiadaceae), a new steroidal pregnane glycoside (Huernioside A) was isolated from dichloromethane fraction (DCM); it was identified as 3β, 11, 14β, 20(R)-tetrahydroxy-pregna-5,9(11)-diene-3-O-β-D-thevetopyranosyl-(1-4)-β-D-cymaropyranoside(HCP) through analysis of 1D, 2D NMR besides ESI-MS data. The alcoholic extract of the aerial part (ALE), DCM and HCP showed inhibitory potential against pancreatic lipase compared to orilstat. Among the tested samples, the ALE and HCP exhibited a promising pancreatic lipase inhibitory commotion through IC50 values of 0.61 ± 0.15, 1.23 ± 0.07 mg/ml (equivalent to 88.8 μM), respectively. HCP was prevailed to have a mixed mode of inhibition as exposed by enzyme kinetic studies. Hydrophobic interactions were the major forces involved in ligand enzyme interactions. In contrast, moderate α-glucosidase inhibitory activities were evidenced for ALE and HCP (% inhibition: 24.8 ± 1.8 and 26.6 ± 2.5, respectively) compared to acarbose. This investigation is the first to report on the possible in vitro anti-obesity and anti-diabetic impact of H. saudi-arabica.