25R/25S stereochemistry of spirostane-type steroidal sapogenins and steroidal saponins via chemical shift of geminal protons of ring-F

Magnetic Resonance in Chemistry

Volumn 41, Issue 11, 2003, Pages 965-968

  Agrawal, Pawan K ^a,b  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

^b NONE   (United States)

Author keywords

1H NMR; NMR; Ring F; Stereochemistry; Steroidal sapogenins; Steroidal saponins

Indexed keywords

CHEMICAL SHIFT; METABOLITES;

1H NMR; NMR CHEMICAL SHIFTS; RING-F; SPIROSTANES; STEROIDAL SAPOGENIN; STEROIDAL SAPONINS;

STEREOSELECTIVITY;

CARBENE; FLUORINE; PROTON; SAPOGENIN; SAPONIN; STEROID;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0242522145     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1278     Document Type: Article

References (35)

1. Waller GR, Yamasaki K (eds). Advances in Experimental Medicine and Biology. Vol. 404: Saponins Used in Traditional and Modern Medicine. Plenum Press: New York, 1996.
2. Hostettmann K, Marston A. Saponins. Cambridge University Press: Cambridge, 1995.
3. Oleszek W, Marston A (eds). Proceedings of the Phytochemical Society Europe, 45: Saponins in Food, Feedstuffs and Medicinal Plants. Kluwer: Dordrecht, 2000.
4. (a) Agrawal PK, Jain DC, Gupta RK, Thakur RS. Phytochemistry 1985; 24: 2479;
5. (b) Agrawal PK, Jain DC, Pathak AK. Magn Reson. Chem. 1995; 33: 923.
6. Agrawal PK. In Advances in Experimental Medicine and Biology. Vol. 404: Saponins Used in Traditional and Modern Medicine, Waller GR, Yamasaki K (eds). Plenum Press: New York, 1996; 299.
7. Patel AV, Blunden G, Crabb T, Sauvaire Y, Baccou Y. Fitoterapia 1987; 58: 56.
8. Agrawal PK, Morris GA, Bunsawansong D. Magn. Reson. Chem. 1997; 35: 441.
9. Agrawal PK, Morris GA, Bunsawansong D. Phytochemistry 1997; 47: 255.
10. (a) Kirk DN, Toms HC, Douglas C, White KA, Smith KE, Latif S, Hubbard RWP. J. Chem. Soc., Perkin Trans 2: 1990; 1567;
11. (b) Puri R, Wong TC, Puri RK. Magn. Reson. Chem. 1993; 31: 278;
12. (c) Iglesias Arteaga MA, Martinez CSP, Gil RP, Manchado FC. J. Chem. Res. (S) 1999; 48;
13. (d) Huang JW, Jiang SH, Tan CH, Zhu DY. Chin. J. Org. Chem. 2002; 11: 917;
14. (e) Carotenuto A, Fattorusso E, Lanzotti V, Magno S, Feo WD, Carnuccio R, D'Acquisto F. J. Nat. Prod. 1997; 60: 1003;
15. (f) Pan WB, Chang FR, Wei LM, Wu YC. J. Nat. Prod. 2003; 66: 161;
16. (g) Mimaki Y, Kanmoto T, Kuroda M, Sashida Y, Nishino A, Satomi Y, Nishino H. Chem. Pharm. Bull. 1995; 43: 1190;
17. (h) Plock A, Beyer G, Hiller K, Grundemann E, Krause E, Nimtz M, Wray V. Phytochemistry 2001; 57: 489;
18. (i) Itabashi M, Segawa K, Ikeda Y, Kondo S, Naganawa H, Koyano T, Umezawa K. Carbohydr. Res. 2000; 323: 57;
19. (j) Ikeda T, Tsumagari H, Nohara T. Chem. Pharm. Bull. 2000; 48: 1062;
20. (k) Wu G, Jiang S, Jiang F, Zhu D, Wu H, Jiang S. Phytochemistry 1997; 42: 1677;
21. (l) Debella A, Haslinger E, Kunert O, Michl G, Adebe D. Phytochemistry 1999; 51: 1069;
22. (m) Carotenuto A, Fattorusso E, Lanzotti V, Magno S. Phytochemistry 1999; 51: 1077;
23. (n) Zaamilpa A, Tortoriello J, Navarro V, Delgado G, Alvarez L. J. Nat. Prod. 2002; 65: 1815;
24. (o) Konishi T, Fujiwara Y, Konoshima T, Kiyosawa S, Nishi M, Miyahara K. Chem. Pharm. Bull. 2001; 49: 318;
25. (p) Han XW, Yu H, Liu XM, Bao X, Yu B, Li C, Hui YZ. Magn. Reson. Chem. 1999; 37: 140;
26. (q) Ahmad VQ, Baqai FT, Ahmad R. Phytochemistry 1993; 34: 511.
27. (a) Tran QL, Tezuka Y, Banskota AH, Tran QK, Saiki I, Kadota S. J. Nat. Prod. 2001; 64: 1127;
28. (b) Soule S, Guntner C, Vazquez A, Argandona V, Moyna P, Ferreira F. Phytochemistry 2000; 55: 217;
29. (c) Pires VS, Taketa ATC, Gosmann G, Schenkel EP. J. Braz. Chem. Soc. 2002; 13: 135;
30. (d) Branke JT, Haslinger E. Liebigs Ann. Chem. 1995; 587;
31. (e) Mimaki Y, Takashi Y, Kuroda M, Sashida Y. Phytochemistry 1997; 45: 1229;
32. (f) Tobari A, Teshima M, Koyanagi J, Kawase M, Miyamae H, Yoza K, Takasaki A, Nagamura Y, Saito S. Eur. J. Med. Chem. 2000; 32: 511;
33. (g) Sang S, Lao A, Wang H, Chen Z. J. Nat. Prod. 1999; 62: 1028;
34. (h) Kim GS, Seong JD, Park SY, Oh SR, Kwack YH. J. Korean Soc. Agric. Chem. 2000; 43: 136;
35. (i) Qiu SX, Li XC, Xiong Y, Dong Y, Chai H, Farnsworth NR, Pezzuto JM, Fong HHS. Planta Med. 2000; 66: 587.