Acid epimerization of 20-keto pregnane glycosides is determined by 2D-NMR spectroscopy

Journal of Biomolecular NMR

Volumn 50, Issue 1, 2011, Pages 91-97

  García, Víctor P ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

Epimerization; Glycosides; NMR; Oligosaccharides

Indexed keywords

CARBOHYDRATE; GLYCOSIDE; PREGNANE DERIVATIVE;

APOPTOSIS; ARTICLE; ASCLEPIADACEAE; CELL DIFFERENTIATION; CYTOSTASIS; DRUG ISOLATION; EPIMERIZATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PULSED FIELD GEL ELECTROPHORESIS;

ACIDS; ASCLEPIADACEAE; CARBOHYDRATE SEQUENCE; GLYCOSIDES; HYDROLYSIS; MOLECULAR SEQUENCE DATA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PREGNANES; PROTONS;

ANIMALIA; APOCYNACEAE; CEROPEGIA;

EID: 80051604300     PISSN: 09252738     EISSN: 15735001     Source Type: Journal    
DOI: 10.1007/s10858-011-9499-z     Document Type: Article

References (25)

1. Agrawal PK (1992) NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 31:3307-3330
2. Bai L, Wang L, Zhao M, Toki A, Hasegawa T, Ogura H, Kataoka T, Hirose K, Sakai J, Bai J, Ando M (2007) Bioactive pregnanes from Nerium oleander. J Nat Prod 70:14-18
3. Chabanel M (1990) Ionic aggregates of 1-1 salts in non-aqueous solutions: structure, thermodynamics and solvation. Pure Appl Chem 62:35-46
4. Coxon B (2009) Development in the Karplus equation as they relate to the NMR coupling constants of carbohydrates. In: Hoston B (ed) Advances in carbohydrate chemistry and biochemistry. Academic Press, Washington
5. Deng J, Liao Z, Chen D (2005) Three new polyoxypregnane glycosides from Marsdenia tenacissima. Helv Chim Acta 88:2675-2682 (Pubitemid 41578550)
6. Ingrassia L, Nshimyumukiza P, Dewelle J, Lefranc F, Wlodarczak L, Thomas S, Dielle G, Chiron C, Zedde C, Tisnes P, van Soest R, Braekman J-C, Darro F, Kiss R (2006) A lactosylated steroid contributes in vivo therapeutics benefits in experimental models of mouse lymphoma and human glioblastoma. J Med Chem 49:1800-1807 (Pubitemid 43376523)
7. Junquera E, Olmos D, Aicart E (2002) Carbohydrate-water interactions of p-nitrophenylglycosides in aqueous solution. Ultrasonic and densitometric studies. Phys Chem Chem Phys 4:352-357
8. Kanchanapoom T, Kasai R, Ohtani K, Andriantsiferana M, Yamasaki K (2002) Pregnane and pregnane glycosides from the malagasky plant, Cynanchum aphyllum. Chem Pharm Bull 50:1031-1034
9. Khare NK, Khare MP, Khare A (1984) Two pregnane ester glycosides from Pergularia pallida. Phytochemistry 23:2931-2935
10. Mitsuhashi H, Nomura T (1965) On the structure of ramanone. Chem Pharm Bull 3:1332-1340
11. Nohara T, Ikeda T, Fujiwara Y, Matsushita S, Noguchi E, Yoshimitsu H, Ono M (2007) Physiological functions of solanaceous and tomato steroidal glycosides. J Nat Med 61:1-13 (Pubitemid 46065441)
12. Peng Y, Li Y, Liu X, Zhang J, Duan J (2008) Antitumor activity of C-21 steroidal glycosides from Cynanchum auriculatum Royle ex Wight. Phytomedicine 15:1016-1020
13. Perrone A, Plaza A, Hamed A, Pizza C, Piacente S (2008) Solenostemma argel: a rich source of very unusual pregnane and 14, 15-secopregnane glycosides with antiproliferative activity. Curr Org Chem 12:1648-1660
14. Russell SJ, Kahn CR (2007) Possible regulation of lifespan by steroid hormones in mice. Nat Rev Mol Cell Biol 8:681-691
15. Shibuya H, Zhang R, Park JD, Takeda Y, Yoshikawa M, Kitagawa I (1992) Indonesian medicinal plants. V. Chemical structures of calotroposides C, D, E, F, and G, five additional new oxypregnane-oligoglycosides from the root of Calotropis gigantean (Asclepiadaceae). Chem Pharm Bull 40:2647-2653
16. Skvortsov D, Lee SJ, Choi MY, Vilesov AF (2009) Hydrated HCl clusters, HCl(H2O) 1-3, in helium nanodroplets: studies of free OH vibrational stretching modes. J Phys Chem 113:7360-7365
17. Smith A, Vincent MA, Hillier IH (1999) Mechanism of acid dissociation in water clusters: electronic structure studies of (H2O) n HX (n = 4, 7; X = OH, F, HS, HSO3, OOSO2H, OOH SO2). J Phys Chem A 103:1132-1139 (Pubitemid 129590623)
18. Tsukamoto S, Hayshi K, Mitsuashi H (1985) The structures of six glycosides, wilfoside C1N, C2N, C3N, C1G, C2G and C3G, with novel sugar chain containing a pair of optically isomeric sugars. Tetrahedron 41:927-934
19. Wang S, Bianco R, Hynes JT (2009) Depth-dependent dissociation of nitric acid at an aqueous surface: Car-Parrinello molecular dynamics. J Phys Chem A 113:1295-1307
20. Warashina T, Noro N (1995) Steroidal glycosides from the root of Cynanchum caudatum M. Chem Pharm Bull 43:977-982
21. Warashina T, Noro N (2000) Steroidal glycosides from the aerial part of Asclepias incarnata. Phytochemistry 53:485-498 (Pubitemid 30141043)
22. Warashina T, Noro N (2008) Steroidal glycosides from the roots of Asclepias curassavica. Chem Pharm Bull 56:315-322 (Pubitemid 351463243)
23. Warashina T, Noro N (2009) Acylated-oxypregnane glycosides from the roots of Asclepias syriaca. Chem Pharm Bull 57:177-184
24. Xhang R, Ye Y-P, Shen Y-M, Liang H-L (2000) Two new cytotoxic C-21 steroidal glycosides from the root of Cynanchum auriculatum. Tetrahedron 56:3875-3879 (Pubitemid 30422388)
25. Yokosuka A, Mimaki Y (2008) Steroidal glycosides from the underground parts of Trillium erectum and their cytotoxic activity. Phytochemistry 69:2724-2730