Triterpene saponins from the roots of Medicago hybrida

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 7, 2006, Pages 2520-2526

  Bialy, Zbigniew ^a   Jurzysta, Marian ^a   Mella, Mariella ^b   Tava, Aldo ^c  

^a STATE RESEARCH INSTITUTE   (Poland)

^b UNIVERSITY OF PAVIA   (Italy)

^c ISTITUTO NAZIONALE DELLA NUTRIZIONE   (Italy)

Author keywords

Chemical structure; FAB MS; Medicago hybrida L.; NMR; Triterpene saponins

Indexed keywords

MEDICAGO; MEDICAGO HYBRIDA;

SAPONIN; TRITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; ISOLATION AND PURIFICATION; MEDICAGO; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT ROOT;

MAGNETIC RESONANCE SPECTROSCOPY; MEDICAGO; MOLECULAR STRUCTURE; PLANT ROOTS; SAPONINS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; TRITERPENES;

EID: 33645959465     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0581628     Document Type: Article

References (51)

1. Jurzysta, M.; Waller, G. R. Antifungal and haemolytic activity of aerial parts of alfalfa (Medicago) species in relation to saponin composition. In Saponins Used in Traditional and Modern Medicine; Waller, G. R., Yamasaki, K., Eds.; Plenum Press: New York, 1996; Vol. 104, pp 565-574.
2. Jurzysta, M.; Bialy, Z. Antifungal and hemolytic activity of roots of alfalfa (Medicago spp.) in relation to saponin composition. In Modern Fungicides and Antifungal Compounds II; Intercept: Andover, Hampshire, U.K., 1999; pp 445-451.
3. Martyniuk, S.; Jurzysta, M.; Wroblewska, B. Influence of powdered aerial parts of various Medicago species on the growth of Gaeumannomyces graminis and Cephalosporium gramineum. Bull. Pol.-Acad. Sci. Biol. Sci. 1999, 47, 163-165.
4. Spiewak, R.; Szostak, W.; Jurzysta, M.; Bialy, Z.; Maleszka, R.; Rzepecka, B.; Mazurek, M. The effect of Medicago spp. on the growth of Trichophyton mentagrophytes (in Polish). Wiad. Parazytol. 2001, 47, 839-844.
5. Martyniuk, S.; Bialy, Z.; Jurzysta, M. Antifungal activity of aerial parts and saponins of Medicago spp. against Cephalosporium gramineum. Allelopathy J. 2004, 13, 75-82.
6. Saniewska, A.; Jarecka, A.; Bialy, Z.; Jurzysta, M. Antifungal activity of saponins from Medicago arabica L. shoots against some pathogens. Allelopathy J. 2005, 16, 1005-1012.
7. Bialy, Z.; Jurzysta, M. The influence of alfalfa (Medicago sativa L.) root saponins on the growth of Trichoderma viride (in Polish). Prog. Plant Prot. 2000, 40, 706-708.
8. Saniewska, A.; Bialy, Z.; Jurzysta, M. The effect of alfalfa (Medicago sativa L.) saponins on Botrytis tulipae and Phoma narciss growth. Phytopathol. Pol. 2003, 27, 15-27.
9. Tava, A.; Odoardi, M. Saponins from Medicago spp.: chemical characterization and biological activity against insects. In Saponins Used in Traditional and Modern Medicine; Waller, G. R., Yamasaki, K., Eds.; Plenum Press: New York, 1996; Vol. 405, pp 97-109.
10. Szczepanik, M.; Bialy, Z.; Jurzysta, M. The insecticidal activity of saponins from various Medicago spp. against Colorado potato beetle, Leptinotarsa decemlineata Say. Allelopathy J. 2004, 14, 177-186.
11. Adal, M. M.; Sehnal, F.; Jurzysta, M. Effect of alfalfa saponins on the moth Spodoptera littoralis. J. Chem. Ecol. 2000, 26, 1065-1078.
12. Morris, R. J.; Dye, W. B.; Gisler, P. S. Isolation, purification and structural identity of an alfalfa root saponin. J. Org. Chem. 1961, 26, 1241-1243.
13. Morris, R. J.; Hussey, E. W. A natural glycoside of medicagenic acid. An alfalfa blossom saponin. J. Org. Chem. 1965, 30, 166-168.
14. Gestetner, B. Structure of a saponin from lucerne (Medicago sativa). Phytochemistry 1971, 10, 2221-2223.
15. Timbekova, A. E.; Abubakirov, N. K. Triterpene glycosides of alfalfa. I. Medicoside G - a novel bisdesmoside from Medicago sativa. Khim. Prir. Soedin. 1984, 451-458.
16. Timbekova, A. E.; Abubakirov, N. K. Triterpene glycosides of alfalfa. II. Medicoside C. Khim. Prir. Soedin. 1985, 805-808.
17. Timbekova, A. E.; Abubakirov, N. K. Triterpene glycosides of alfalfa. III. Medicoside I. Khim. Prir. Soedin. 1986, 607-610.
18. Timbekova, A. E.; Abubakirov, N. K. Triterpene glycosides of alfalfa. IV. Medicoside J. Khim. Prir. Soedin. 1986, 610-613.
19. Massiot, G.; Lavaud, C.; Guillaumem, D.; Le Men-Olivier, L. Reinvestigation of sapogenins and prosapogenins from alfalfa (Medicago sativa). J. Agric. Food Chem. 1988, 36, 902-909.
20. Massiot, G.; Lavaud, C.; Le Men-Olivier, L.; Binst, G.; Miller, S. F.; Fales, H. M. Structural elucidation of alfalfa root saponins by MS and NMR analysis. J. Chem. Soc., Perkin Trans. 1988, 3071-3079.
21. Levy, M.; Zehavi, U.; Naim, M.; Polacheck, J. Isolation, structure determination and antifungal activity of a new native alfalfa root saponin. Carbohydr. Res. 1989, 193, 115-123.
22. Timbekova, A. E.; Larin, M. F.; Yagudaev, M. R.; Abubakirov, N. K. Triterpene glycosides of alfalfa. V. Medicoside H. Khim. Prir. Soedin. 1989, 673-677.
23. Oleszek, W.; Price, K. R.; Colquhoun, I. J.; Jurzysta, M.; Ploszynski, M.; Fenwick, G. R. Isolation and identification of alfalfa (Medicago sativa L.) root saponins: their activity in relation to a fungal bioassay. J. Agric. Food Chem. 1990, 38, 1810-1817.
24. Timbekova, A. E.; Verechagin, A. L.; Semenov, A. A.; Abubakirov, N. K. Triterpene glycosides of alfalfa. VI. Medicoside L. Khim. Prir. Soedin. 1990, 221-227.
25. Massiot, G.; Lavaud, C.; Besson, V.; Le Men-Olivier, L.; Van Binst, G. Saponins from aerial parts of alfalfa (Medicago sativa). J. Agric. Food Chem. 1991, 39, 78-82.
26. Massiot, G.; Lavaud, C.; Benkhaled, M.; Le Men-Olivier, L. Soyasaponin VI, a new maltol conjugate from alfalfa and soybean. J. Nat. Prod. 1992, 55, 1339-1342.
27. Oleszek, W.; Jurzysta, M.; Ploszynski, M.; Coloquhoun, I. J.; Price, K. R.; Fenwick, G. R. Zahnic acid tridesmoside and other dominant saponins from alfalfa (Medicago sativa L.) aerial parts. J. Agric. Food Chem. 1992, 40, 191-196.
28. Timbekova, A. E.; Shashkov, A. S.; Abubakirov, N. K. Triterpene glycosides from alfalfa. VII. Medicosides E and F. Khim. Prir. Soedin. 1993, 5, 701-705.
29. Timbekova, A. E.; Shashkov, A. S.; Abubakirov, N. K. Triterpene glycosides from alfalfa. VIII. Medicoside E from the leaves. Khim. Prir. Soedin. 1993, 5, 705-710.
30. Bialy, Z.; Jurzysta, M.; Oleszek, W.; Piacente, S.; Pizza, C. Saponins in alfalfa (Medicago sativa L.) root and their structural elucidation. J. Agric. Food Chem. 1999, 47, 3185-3192.
31. Oleszek, W.; Price, K. R.; Fenwick, G. R. Triterpene saponins from the roots of Medicago lupulina L. (black medic trefoil). J. Sci. Food Agric. 1988, 43, 289-297.
32. Walter, E. D. Isolation of a saponin, hederin and its sapogenin hederagenin from bur clover (Medicago hispida). J. Am. Pharm. Assoc. 1957, 47, 466-467.
33. Mahato, S. B. Triterpenoid saponins from Medicago hispida. Phytochemistry 1991, 30, 3389-3393.
34. Konjo, J.; Uemara, H.; Nakamura, M.; Nohara, T. Two novel triterpenoidal glycosides from Medicago polymorpha L. Chem. Pharm. Bull. 1994, 42, 1339-1341.
35. Bialy, Z.; Jurzysta, M..; Mella, M.; Tava, A. Triterpene saponins from aerial parts of Medicago arabica L. J. Agric. Food Chem. 2004, 52, 1095-1099.
36. Huhman, D. V.; Sumner, L. W. Metabolic profiling of saponins in Medicago sativa and Medicago truncatula using HPLC coupled to an electrospray ion-trap mass spectrometer. Phytochemistry 2002, 59, 347-360.
37. Kapusta, I.; Stochmal, A.; Perrone, A.; Piacente, S.; Pizza, C.; Oleszek, W. Triterpene saponins from barrel medic (Medicago truncatula) aerial parts. J. Agric. Food Chem. 2005, 53, 2164-2170.
38. Tava, A.; Mella, M.; Avato, P.; Argentieri, M. P.; Bialy, Z.; Jurzysta, M. Triterpenoid glycosides from leaves of M. arborea L. J. Agric. Food Chem. 2005, 53, 9954-9965.
39. Lesins, K. A.; Lesins, I. Genus Medicago (Leguminosae). A Taxogenetic Study; W. Junk: Dordrecht, The Netherlands, 1979; pp 139-140.
40. Tava, A.; Oleszek, W.; Jurzysta, M.; Berardo, N.; Odoardi, M. Alfalfa saponins and sapogenins: isolation and quantification in two different cultivars. Phytochem. Anal. 1993, 4, 269-274.
41. Nagao, T.; Tanaka, R.; Shimokawa, H.; Okabe, H. Studies on the constituents of Aster scaber Thunb. II. Structures of echinocystic acid glycosides isolated from the roots. Chem. Pharm. Bull. 1991, 39, 1719-1725.
42. Jia, Z.; Koike, K.; Nikaido, T. Major triterpenoid saponins from Saponaria officinalis. J. Nat. Prod. 1998, 61, 1368-1373.
43. Kizu, H.; Kitayama, S.; Nakatani, F.; Tomimori, T.; Namba, T. Studies on Nepalese crude drugs. III. On the saponins of Hedera nepalensis K. Koch. Chem. Pharm. Bull. 1985, 33, 3324-3329.
44. Shao, Y.; Li, Y. L.; Zhou, B. N. Phenolic and triterpenoid glycosides from Aster batangensis. Phytochemistry 1996, 41, 1593-1598.
45. Tava, A.; Mella, M.; Bialy, Z.; Jurzysta, M. Stability of saponins in alcoholic solutions: ester formation as artifacts. J. Agric. Food Chem. 2003, 51, 1797-1800.
46. Hu, M.; Ogawa, K.; Sashida, Y.; Xiao, P. G. Triterpenoid glucuronide saponins from root bark of Aralia armata. Phytochemistry 1995, 39, 179-184.
47. Mizui, F.; Kasai, R.; Ohtani, K.; Tanaka, O. Saponins from brans of quinoa, Chenopodium quinoa Willd. II. Chem. Pharm. Bull. 1990, 38, 375-377.
48. Mithöfer, A.; Jakupovic, J.; Weiler, E. W. A triterpenoid glycoside from Spinacia oleracea. Nat. Prod. Lett. 1999, 14, 5-10.
49. Takabe, S.; Takeda, T.; Chen, Y.; Ogihara, Y. Triterpenoid glycosides from the roots of Tetrapanax papyriferum K. Koch. III. Structures of four new saponins. Chem. Pharm. Bull. 1985, 33, 4701-4706.
50. Dewick, P. M. In Medicinal Natural Products - A Biosynthetic Approach, 2nd ed.; Wiley: Chichester, U.K., 2001.
51. Torsell, K. B. G. In Natural Product Chemistry - A Mechanistic, Biosynthetic and Ecological Approach; Swedish Pharmaceutica Society: Sweden, 1997.