Besides a series of normal C_(21) steroids from Marsdenia incisa incisa P.T.Li et Y.P.Li, it small amount of novel C_(21) steroidal glycoside (Ⅱ) had been isolated. The mild acidic hydrolysis of (Ⅱ) afforded genin-(...Besides a series of normal C_(21) steroids from Marsdenia incisa incisa P.T.Li et Y.P.Li, it small amount of novel C_(21) steroidal glycoside (Ⅱ) had been isolated. The mild acidic hydrolysis of (Ⅱ) afforded genin-(Ⅰ). By spectroscopic analyses of IR, ELMS, FDMS, ~1H NMR, ^(13)C NMR (DEPT, PRFT), ~1H-~1H COSY, ~1H-^(13)C COSY for (Ⅰ) and (Ⅱ), (Ⅰ) had been deduced as B-nor (7) -6β-formyl-pregnane-3β, 5β, 8β, 12β, 14β, 17β, 20-heptatol, named neomarinogenin; (Ⅱ) had been deduced as neomarinogenin 3-O-β-D-thevetopyranosyl-(1→-4)-β-Dcymaropyranosyl-(1→4)-β-D-cymaropyranoside, named neomarinoside. Their physical and spectral data were as follows. Neomarinogenin (Ⅰ). A colorless prism from Me_2 CO, mp 202—205℃, 〔α〕_D^(17)+28.81°(MeOH, c0.05), C_(21)H_(34)O_8 (Found: C, 60.76; H, 8.19, C_(21)H_(34)O_8, requires C, 60.87. H, 8.21％); IRv_(max)^(KBr)cm^(-1): 3450 (OH), 1700 (C=O), 1050(C-O-C); EIMS m/z: 397 (M-OH), 380 (397-OH), 379, 378 (M-2H_2O), 36; (M-3H_2O), 342 (M-4H_2O), 333,展开更多
Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C_（21） steroidal glycosides（1–4） and one known compound stauntoside F（5）. Their chemical structures were characterized ...Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C_（21） steroidal glycosides（1–4） and one known compound stauntoside F（5）. Their chemical structures were characterized by sophisticated analyses of IR, HRESI-TOF-MS, 1D, and 2D-NMR data, together with chemical methods, which showed interesting 13,14：14,15-disecopregnane-type skeleton or 14,15-secopregnane-type skeleton C_（21） steroidal glycosides. Among them, compound 1 was determined to be glaucogenin C 3-O-b-D-glucopyranosyl-（1 → 4）-b-D-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-D-thevetopyranoside. Compound 2 was characterized to be hirundigenin 3-O-a-L-diginopyranosyl-（1 → 4）-b-D-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-D-30-demethyl-thevetopyranoside. Compound 3 was identified to be（14S,16 S,20R）-14,16-14,20-15,20-triepoxy-14,15-secopregn-5-en-3-ol-3-O-a-L-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-D-oleandropyranoside.Compound 4 was identified to be（14S,16 S,20R）-14,16-14,20-15,20-triepoxy-14,15-secopregn-5-en-3-ol-3-O-a-L-cymaropyranosyl-（1 → 4）-b-D-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-Dthevetopyranoside. Among them, compound 2 was hirundigenin type C21 steroidal glycoside that existed in nature as epimers due to the presence of 14-hemiketal hydroxyl group in its structure. In addition, the anti-inflammatory and cardiomyocyte protective effects of compounds 1–4 were evaluated. We found that they exhibited significant protective effects on hypoxia/reoxygenation induced cardiomyocyte injury, but did not showed obvious anti-inflammatory function.展开更多
基金This work was supported by grants from International Foundation for Science in Sweden and National Science Foundation of China.
文摘Besides a series of normal C_(21) steroids from Marsdenia incisa incisa P.T.Li et Y.P.Li, it small amount of novel C_(21) steroidal glycoside (Ⅱ) had been isolated. The mild acidic hydrolysis of (Ⅱ) afforded genin-(Ⅰ). By spectroscopic analyses of IR, ELMS, FDMS, ~1H NMR, ^(13)C NMR (DEPT, PRFT), ~1H-~1H COSY, ~1H-^(13)C COSY for (Ⅰ) and (Ⅱ), (Ⅰ) had been deduced as B-nor (7) -6β-formyl-pregnane-3β, 5β, 8β, 12β, 14β, 17β, 20-heptatol, named neomarinogenin; (Ⅱ) had been deduced as neomarinogenin 3-O-β-D-thevetopyranosyl-(1→-4)-β-Dcymaropyranosyl-(1→4)-β-D-cymaropyranoside, named neomarinoside. Their physical and spectral data were as follows. Neomarinogenin (Ⅰ). A colorless prism from Me_2 CO, mp 202—205℃, 〔α〕_D^(17)+28.81°(MeOH, c0.05), C_(21)H_(34)O_8 (Found: C, 60.76; H, 8.19, C_(21)H_(34)O_8, requires C, 60.87. H, 8.21％); IRv_(max)^(KBr)cm^(-1): 3450 (OH), 1700 (C=O), 1050(C-O-C); EIMS m/z: 397 (M-OH), 380 (397-OH), 379, 378 (M-2H_2O), 36; (M-3H_2O), 342 (M-4H_2O), 333,
基金supported by grants from Science and Technology Planning Project of Guangdong Province,China(No.2015B030301005)
文摘Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C_（21） steroidal glycosides（1–4） and one known compound stauntoside F（5）. Their chemical structures were characterized by sophisticated analyses of IR, HRESI-TOF-MS, 1D, and 2D-NMR data, together with chemical methods, which showed interesting 13,14：14,15-disecopregnane-type skeleton or 14,15-secopregnane-type skeleton C_（21） steroidal glycosides. Among them, compound 1 was determined to be glaucogenin C 3-O-b-D-glucopyranosyl-（1 → 4）-b-D-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-D-thevetopyranoside. Compound 2 was characterized to be hirundigenin 3-O-a-L-diginopyranosyl-（1 → 4）-b-D-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-D-30-demethyl-thevetopyranoside. Compound 3 was identified to be（14S,16 S,20R）-14,16-14,20-15,20-triepoxy-14,15-secopregn-5-en-3-ol-3-O-a-L-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-D-oleandropyranoside.Compound 4 was identified to be（14S,16 S,20R）-14,16-14,20-15,20-triepoxy-14,15-secopregn-5-en-3-ol-3-O-a-L-cymaropyranosyl-（1 → 4）-b-D-cymaropyranosyl-（1 → 4）-b-D-digitoxopyranosyl-（1 → 4）-b-Dthevetopyranoside. Among them, compound 2 was hirundigenin type C21 steroidal glycoside that existed in nature as epimers due to the presence of 14-hemiketal hydroxyl group in its structure. In addition, the anti-inflammatory and cardiomyocyte protective effects of compounds 1–4 were evaluated. We found that they exhibited significant protective effects on hypoxia/reoxygenation induced cardiomyocyte injury, but did not showed obvious anti-inflammatory function.
