Triterpenoid glycosides from leaves of Medicago arborea L.

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 26, 2005, Pages 9954-9965

  Tava, Aldo ^a   Mella, Mariella ^b   Avato, Pinarosa ^c   Argentieri, Maria Pia ^c   Bialy, Zbigniew ^d   Jurzysta, Marian ^d  

^a ISTITUTO NAZIONALE DELLA NUTRIZIONE   (Italy)

^b UNIVERSITY OF PAVIA   (Italy)

^c UNIVERSITY OF BARI   (Italy)

^d STATE RESEARCH INSTITUTE   (Poland)

Author keywords

Chemical structure; ESI MS MS; FAB MS; Medicago arborea L.; NMR; Saponins; Triterpene glycosides

Indexed keywords

CARBOHYDRATE; GLYCOSIDE; PLANT EXTRACT; SAPONIN; TRITERPENE;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MEDICAGO; PLANT LEAF; THIN LAYER CHROMATOGRAPHY;

CARBOHYDRATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; GLYCOSIDES; HYDROLYSIS; MEDICAGO; PLANT EXTRACTS; PLANT LEAVES; SAPONINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; TRITERPENES;

MEDICAGO; MEDICAGO ARBOREA;

EID: 30544451205     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf052468x     Document Type: Article

References (42)

1. Martiniello, P.; Baviello, G. Preliminary evaluation for agronomic traits in accessions of Atriplex and Medicago shrubs. REUR Tech. Ser. FAO 1993, 28, 95-99.
2. Stringi, L.; Sarno, R.; Amato, G.; Leto, G.; Pristina, L.; Corrao, A. Shrubs utilization in semi-arid environment: bio-agronomic aspects and their use in sheep husbandry. World Rev. Anim. Prod. 1987, 23, 79-90.
3. Jaretzy, R. The occurrence of saponins in species of genus Medicago. Angew. Bot. 1940, 22, 147-156.
4. Torck et al. Some polyphenols of Medicago arborea. Plantes Med. Phytoter. 1980, 14, 20-25.
5. Torck et al. Flavonoid heterosides of Medicago arborea. Pharmazie 1983, 38, 783.
6. 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.
7. Morris, R. J.; Hussey, E. W. A natural glycoside of medicagenic acid. An alfalfa blossom saponin. J. Org. Chem. 1965, 30, 166-168.
8. Gestetner, B. Structure of a saponin from lucerne (Medicago sativa). Phytochemistry 1971, 10, 2221-2223.
9. 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.
10. Timbekova, A. E.; Abubakirov, N. K. Triterpene glycosides of alfalfa. II. Medicoside C. Khim. Prir. Soedin. 1985, 805-808.
11. Timbekova, A. E.; Abubakirov, N. K. Triterpene glycosides of alfalfa. III. Medicoside I. Khim. Prir. Soedin. 1986, 607-610.
12. Timbekova, A. E.; Abubakirov, N. K. Triterpene glycosides of alfalfa. IV. Medicoside J. Khim. Prir. Soedin. 1986, 610-613.
13. Massiot, G.; Lavaud, C.; Guillaumen, D.; Le Men-Olivier, L. Reinvestigation of saponins and prosapogenins from alfalfa (Medicago sativa). J. Agric. Food Chem. 1988, 36, 902-909.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. Mahato, S. B. Triterpenoid saponins from Medicago hispida. Phytochemistry 1991, 30, 3389-3393.
28. Konjo, J.; Uemara, H.; Nakamura, M.; Nohara, T. Two novel triterpenoidal glycosides from Medicago polymorpha L. Chem. Pharm. Bull. 1994, 42, 1339-1341.
29. 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.
30. 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.
31. 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.
32. Oleszek, W. Alfalfa saponins: structure, biological activity and chemotaxonomy. In Saponins Used in Food and Agriculture; Waller, G. R., Yamasaki, K., Eds.; Plenum Press: New York, 1996; pp 155-170.
33. 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 Publishing: New York, 1996; pp 565-574.
34. Tava, A.; Odoardi, M. Saponins from Medicago spp.: chemical characterization and biological activity against insects. In Saponins Used in Food and Agriculture; Waller, G. R., Yamasaki, K., Eds.; Plenum Publishing: New York, 1996; pp 97-109.
35. Avato, P.; Bucci, R.; Tava, A.; Vitali, C.; Rosato, A.; Bialy, Z.; Jurzysta, M. Antimicrobial activity of saponins from Medicago sp. Abstract Book, 3rd International Symposium on Natural Drugs, Napoli, Italy, 2003; p 73.
36. 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.
37. 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.
38. Jia, Z.; Koike, K.; Nikaido, T. Major triterpenoid saponins from Saponaria officinalis. J. Nat. Prod. 1998, 61, 1368-1373.
39. Jurzysta, M. Transformation of soyasapogenol B into soyasapogenols C, D and F under acidic conditions. Proceedings of the 14th International Symposium on Natural Products; 1984; pp 127.
40. Budzikiewicz, H.; Wilson, J. M.; Djerassi, C. Mass spectrometry in structural and stereochemical problems. XXXII. Pentacyclic triterpenes. J. Am. Chem. Soc. 1963, 85, 3688-3699.
41. Dewick, P. M. In Medicinal Natural Products - A Biosynthetic Approach, 2nd ed.; Wiley: Chichester, U.K., 2001.
42. Torsell, K. B. G. In Natural Product Chemistry - A Mechanistic, Biosynthetic and Ecological Approach; Swedish Pharmaceutical Society: Stockholm, Sweden, 1997.