Oleanane glycosides from Astragalus tauricolus: Isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling

Phytochemistry

Volumn 86, Issue , 2013, Pages 184-194

  Gülcemal, Derya ^a   Masullo, Milena ^b   Napolitano, Assunta ^b   Karayildirim, Tamer ^a   Bedir, Erdal ^c   Alankuş Çaliskan, Özgen ^a   Piacente, Sonia ^b  

^a EGE UNIVERSITY   (Turkey)

^b UNIVERSITY OF SALERNO   (Italy)

^c EGE UNIVERSITY   (Turkey)

Author keywords

Astragalus tauricolus; HPLC ESIMSn profiling; Oleanane saponins

Indexed keywords

DRUG DERIVATIVE; GLYCOSIDE; OLEANANE; OLEANOLIC ACID;

ARTICLE; ASTRAGALUS PLANT; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TANDEM MASS SPECTROMETRY;

ASTRAGALUS PLANT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOSIDES; MOLECULAR STRUCTURE; OLEANOLIC ACID; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

ASTRAGALUS (ANGIOSPERM);

EID: 84872031839     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.10.001     Document Type: Article

References (56)

1. Z. Aytac Astragalus L A. Guner, N. Ozhatay, T. Ekim, K.H.C. Basar, Flora of Turkey and the East Aegean Islands vol. 11 2000 Edinburgh University Press Edinburgh 79 88
2. E. Bedir, İ. Çaliş, R. Aquino, S. Piacente, and C. Pizza Cycloartane triterpene glycosides from the roots of Astragalus brachypterus and Astragalus microcephalus J. Nat. Prod. 61 1998 1469 1472
3. E. Bedir, İ. Çaliş, R. Aquino, S. Piacente, and C. Pizza Secondary metabolites from the roots of Astragalus trojanus J. Nat. Prod. 62 1999 563 568
4. E. Bedir, İ. Çaliş, R. Aquino, S. Piacente, and C. Pizza Trojanoside H: A cycloartane-type glycoside from the aerial parts of Astragalus trojanus Phytochemistry 51 1999 1017 1020
5. E. Bedir, N. Pugh, İ. Çaliş, D.S. Pasco, and I.A. Khan Immunostimulatory effects of cycloartane-type triterpene glycosides from Astragalus species Biol. Pharm. Bull. 23 2000 834 837
6. E. Bedir, I. Çaliş, C. Dunbar, R. Sharan, J.K. Buolamwini, and I.A. Khan Two novel cycloartane-type triterpene glycosides from the roots of Astragalus prusianus Tetrahedron 57 2001 5961 5966
7. U. Çakilcioǧlu, and I. Türkoǧlu An ethnobotanical survey of medicinal plants in Sivrice (Elaziǧ-Turkey) J. Ethnopharmacol. 132 2010 165 175
8. İ. Çaliş, A. Yürüker, D. Taşdemir, A.D. Wright, O. Sticher, Y.D. Luo, and J.M. Pezzuto Cycloartane triterpene glycosides from the roots of Astragalus melanophrurius Planta Med. 63 1997 183 186
9. İ. Çaliş, A.A. Dönmez, A. Perrone, C. Pizza, and S. Piacente Cycloartane glycosides from Astragalus campylosema Boiss ssp. campylosema Phytochemistry 69 2008 2634 2638
10. C. Chu, H.X. Cai, M.T. Ren, E.H. Liu, B. Li, L.W. Qi, and P. Li Characterization of novel astragaloside malonates from Radix Astragali by HPLC with ESI quadrupole TOF MS J. Sep. Sci. 33 2010 570 581
11. B. Cui, Y. Sakai, T. Takeshita, J. Kinjo, and T. Nohara Four new oleanene derivatives from the seeds of Astragalus complanatus Chem. Pharm. Bull. 40 1992 136 138
12. B. Cui, Y. Sakai, T. Takeshita, J. Kinjo, and T. Nohara Glycosides from the Seeds of Astragalus sinicus L Chem. Pharm. Bull. 40 1992 3330 3333
13. B. Cui, J. Kinjo, and T. Nohara Triterpene glycosides from the bark of Robinia pseudo-acacia L Chem. Pharm. Bull. 40 1992 2995 2999
14. P.H. Davis Flora of Turkey and the East Aegean Islands vol. 3 1970 Edinburgh University Press Edinburgh pp. 49-254
15. S. De Marino, N. Borbone, M. Iorizzi, G. Esposito, J.B. McClintock, and F. Zollo Bioactive asterosaponins from the starfish Luidia quinaria and Psilaster cassiope. Isolation and structure characterization by two-dimensional NMR spectroscopy J. Nat. Prod. 66 2003 515 519
16. B. Dinda, S. Debnath, B.C. Mohanta, and Y. Harigaya Naturally occurring triterpenoid saponins Chem. Biodivers. 7 2010 2327 2580
17. Y. Ding, R. Tian, J. Kinjo, T. Nohara, and I. Kitagawa Three new oleanene glycosides from Sophora flavescens Chem. Pharm. Bull. 40 1992 2990 2994
18. P. Gariboldi, F. Pelizzoni, M. Tatò, L. Verotta, N.A. El-Sebakhy, A.M. Asaad, R.M. Abdallah, and S.M. Toaima Cycloartane triterpene glycosides from Astragalus trigonus Phytochemistry 40 1995 1755 1760
19. D. Gülcemal, Ö. Alankuş-Çalişkan, A. Perrone, F. Özgökçe, S. Piacente, and E. Bedir Cycloartane glycosides from Astragalus aureus Phytochemistry 72 2011 761 768
20. D. Gülcemal, M. Masullo, E. Bedir, M. Festa, T. Karayildirim, Ö. Alankuş-Çalişkan, and S. Piacente Triterpene Glycosides from Astragalus angustifolius Planta Med. 78 2012 720 729
21. T. Hirakawa, M. Okawa, J. Kinjo, and T. Nohara Studies on legominous plants. Part 63. A new oleanane glucuronide obtained from the aerial parts of Melilotus officinalis Chem. Pharm. Bull. 48 2000 286 287
22. İ. Horo, E. Bedir, A. Perrone, F. Özgökçe, S. Piacente, and Ö. Alankuş-Çalişkan Triterpene glycosides from Astragalus icmadophilus Phytochemistry 71 2010 956 973
23. I. Ionkova Producing triterpene saponins by conventional and genetically-transformed cultures of Astragalus hamosus L. (Fabaceae) Probl. Farmakol. Farmat. 5 1991 32 38
24. I. Kapusta, A. Stochmal, A. Perrone, S. Piacente, C. Pizza, and W. Oleszek Triterpene saponins from barrel medic (Medicago truncatula) aerial parts J. Agric. Food Chem. 53 2005 2164 2170
25. 13C NMR Study of α- and β-anomeric pairs of d-mannopyranosides and l-rhamnopyranosides Tetrahedron 35 1979 1427 1432
26. Z.A. Khushbaktova, M.A. Agzamova, V.N. Syrov, N.V. Radchenko, N.M. Mirsalikhova, and F.T. Umarova Influence of cycloartanes from plants of the genus Astragalus and their synthetic analogs on the contractive function of the myocardium and the activity of Na, K-ATPase Khim. Prir. Soedin. 4 1994 510 514
27. T. Kikuchi, T. Akihisa, H. Tokuda, M. Ukiya, K. Watanabe, and H. Nishino Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models J. Nat. Prod. 70 2007 918 922
28. I. Kitawaga, M. Yoshikawa, H.K. Wang, M. Saito, V. Tosirisuk, T. Fujiwara, and K. Tomita Revised structures of soyasapogenols A, B and E, oleanane-sapogenols from soybean. Structures of soyasaponins I, II and III Chem. Pharm. Bull. 30 1982 2294 2297
29. I. Kitawaga, H.K. Wang, M. Saito, and M. Yoshikawa Saponin and sapogenol. XXXIII. Chemical constituents of the seeds of Vigna angularis (Willd) Ohwi et Ohashi. (3). Azukisaponins V and VI Chem. Pharm. Bull. 31 1983 683 688
30. I. Kitawaga, H.K. Wang, M. Saito, and M. Yoshikawa Saponin and sapogenol. XXXVII. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (4). Astragaloside VII and VIII Chem. Pharm. Bull. 31 1983 716 722
31. I. Kitawaga, H.K. Wang, M. Saito, and M. Yoshikawa Saponin and sapogenol. XXXII. Chemical constituents of the seeds of Vigna angularis (Willd) Ohwi et Ohashi. (2). Azukisaponins I, II, III and VI Chem. Pharm. Bull. 31 1983 674 682
32. T. Konoshima, M. Kozuka, M. Haruna, K. Ito, T. Kimura, and H. Tokuda Studies on the constituents of leguminous plants XII. The structures of new triterpenoid saponins from Wistaria branchybotrys Sieb. et Zucc Chem. Pharm. Bull. 37 1989 2731 2735
33. T. Konoshima, M. Kozuka, M. Haruna, and K. Ito Constituents of leguminous plants, XIII. New triterpenoid saponins from Wistaria brachybotrys J. Nat. Prod. 54 1991 830 836
34. I. Krasteva, S. Nikolov, M. Kaloga, and G. Mayer Triterpenoid saponins from Astragalus corniculatus Z. Naturforsch. B. 61 2006 1166 1169
35. I. Krasteva, S. Nikolov, M. Kaloga, and G. Mayer A new saponin lactone from Astragalus corniculatus Nat. Prod. Res. 21 2007 941 945
36. E. Lev Reconstructed materia medica of the Medieval and Ottoman al-Sham J. Ethnopharmacol. 80 2002 167 179
37. A. Mari, A. Napolitano, A. Perrone, C. Pizza, and S. Piacente An analytical approach to profile steroidal saponins in food supplements: The case of Ruscus aculeatus Food Chem. 134 2012 461 468
38. K.M. Mohamed, K. Ohtani, R. Kasai, and K. Yamasaki Oleanene glycosides from seeds of Trifolium alexandrinum Phytochemistry 40 1995 1237 1242
39. A. Nalbantsoy, T. Nesil, S. Erden, İ. Çaliş, and E. Bedir Adjuvant effects of Astragalus saponins macrophyllosaponin B and astragaloside VII J. Ethnopharmacol. 134 2011 897 903
40. A. Napolitano, T. Muzashvili, A. Perrone, C. Pizza, E. Kemertelidze, and S. Piacente Steroidal glycosides from Ruscus ponticus Phytochemistry 72 2011 651 661
41. M. Özipek, A.A. Dönmez, İ. Çaliş, R. Brun, P. Rüedi, and D. Taşdemir Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius Phytochemistry 66 2005 1168 1173
42. A. Perrone, T. Muzashvili, A. Napolitano, A. Skhirtladze, E. Kemertelidze, C. Pizza, and S. Piacente Steroidal glycosides from the leaves of Ruscus colchicus: Isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling Phytochemistry 70 2009 2078 2088
43. E. Polat, Ö. Alankuş-Calişkan, A. Perrone, S. Piacente, and E. Bedir Cycloartane-type glycosides from Astragalus amblolepis Phytochemistry 71 2009 628 634
44. E. Polat, E. Bedir, A. Perrone, S. Piacente, and Ö. Alankuş-Calişkan Triterpenoid saponins from Astragalus wiedemannianus Fischer Phytochemistry 71 2010 658 662
45. M.M. Radwan, N.A. El-Sebakhy, A.M. Asaad, S.M. Toaima, and D.G.I. Kingston Kahiricosides II-V cycloartane glycosides from an Egyptian collection of Astragalus kahiricus Phytochemistry 65 2004 2909 2913
46. S. Sakamato, S. Kofuji, M. Kuroyanagi, A. Ueno, and S. Sekita Saponins from Trifolium repens Phytochemistry 31 1992 1773 1777
47. T. Savran, D. Gülcemal, M. Masullo, T. Karayildirim, E. Polat, S. Piacente, and Ö. Alankuş-Çalişkan Cycloartane glycosides from Astragalus erinaceus Rec. Nat. Prod. 6 2012 230 236
48. C. Sevimli-Gür, İ. Onbaşilar, P. Atilla, R. Genç, N. Çakar, İ. Deliloǧlu-Gürhan, and E. Bedir In vitro growth stimulatory and in vivo wound healing studies on cycloartane-type saponins of Astragalus genus J. Ethnopharmacol. 134 2011 844 850
49. T. Takeshita, S. Hamada, and T. Nohara New triterpenoid sapogenols from Abrus cantoniensis (I) Chem. Pharm. Bull. 37 1989 846 848
50. W. Tang, and G. Eisenbrand Chinese Drugs of Plant Origin 1992 Springer-Verlag Ed. Berlin pp. 191-197
51. M. Udayama, M. Ohkawa, N. Yoshida, J. Kinjo, and T. Nohara Structures of three new oleanene glucuronides isolated from Lathyrus palustris var. Pilosus and hepatoprotective activity Chem. Pharm. Bull. 46 1998 1412 1415
52. Q. Xu, X. Ma, and X. Liang Determination of Astragalosides in the roots of Astragalus spp. using liquid chromatography tandem atmospheric pressure chemical ionization mass spectrometry Phytochem. Anal. 18 2007 419 427
53. E. Yeşilada, E. Bedir, İ. Çaliş, Y. Takaishi, and Y. Ohmoto Effects of triterpene saponins from Astragalus species on in vitro cytokine release J. Ethnopharmacol. 96 2005 71 77
54. K. Yoshikawa, A. Mizutani, Y. Kan, and S. Arihara Antisweet natural products. XII. Structures of Sitakisosides XI-XX from Stephanotis lutchuensis Koidz. Var. japonica Chem. Pharm. Bull. 45 1997 62 67
55. K. Yoshikawa, H. Ogata, S. Arihara, H.C. Chang, and J.-D. Wang Antisweet natural products. XIII. Structures of Alternosides I-X from Gymnema alternifolium Chem. Pharm. Bull. 46 1998 1102 1107
56. Y. Zu, M. Yan, Y. Fu, W. Liu, L. Zhang, C. Gu, and T. Efferth Determination and quantification of astragalosides in Radix Astragali and its medicinal products using LC-MS J. Sep. Sci. 32 2009 517 525