Saponins with highly hydroxylated oleanane-type aglycones from Silphium asteriscus L.

Phytochemistry

Volumn 97, Issue , 2014, Pages 70-80

  Masullo, Milena ^a   Calabria, Lalita ^b   Gallotta, Dario ^a   Pizza, Cosimo ^a   Piacente, Sonia ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b EVERGREEN STATE COLLEGE   (United States)

Author keywords

Highly hydroxylated aglycones; Oleanane type saponins; Silphium asteriscus

Indexed keywords

SILPHIUM ASTERISCUS;

ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; OLEANANE; OLEANOLIC ACID; SAPONIN;

ARTICLE; ASTERACEAE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; FEMALE; HELA CELL LINE; HIGHLY HYDROXYLATED AGLYCONES; HUMAN; ISOLATION AND PURIFICATION; JURKAT CELL LINE; NUCLEAR MAGNETIC RESONANCE; OLEANANE-TYPE SAPONINS; SILPHIUM ASTERISCUS;

HIGHLY HYDROXYLATED AGLYCONES; OLEANANE-TYPE SAPONINS; SILPHIUM ASTERISCUS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; ASTERACEAE; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HELA CELLS; HUMANS; JURKAT CELLS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLEANOLIC ACID; SAPONINS;

EID: 84890433946     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.10.013     Document Type: Article

References (29)

1. F. Bohlmann, and J. Jakupovic Natural terpene derivatives 238. New sesquiterpene hydrocarbons with anomalous carbon skeletons from Silphium species Phytochemistry 19 1980 259 265
2. L.M. Calabria, S. Piacente, I. Kapusta, S.F. Dharmawardhane, F.M. Segarra, P.J. Pessiki, and T.J. Mabry Triterpene saponins from Silphium radula Phytochemistry 69 2008 961 972
3. J.A. Clevinger New Combinations in Silphium (Asteracaceae: Heliantheae) Novon 14 2004 275 277
4. J.A. Clevinger, and J.L. Panero Phylogenetic analysis of Silphium and subtribe Engelmanniinae (Asteraceae: Heliantheae) based on ITS and ETS sequence data Am. J. Bot. 87 2000 565 572
5. E.S. Davidyants, I.A. Kartasheva, and I.V. Neshin The effect of triterpene glycosides of Silphium perfoliatum L. on phytopathogenic fungi Rastit. Resour. 33 1997 93 98
6. E.S. Davidyants, Zh.M. Putieva, V.A. Bandyukova, and N.K. Abubakirov Triterpene glycosides of Silphium perfoliatum Chem. Nat. Compd. 1 1984 120 121
7. E.S. Davidyants, Zh.M. Putieva, V.A. Bandyukova, and N.K. Abubakirov Triterpene glycosides of Silphium perfoliatum II Chem. Nat. Compd. 20 1984 636
8. E.S. Davidyants, Zh.M. Putieva, V.A. Bandyukova, and N.K. Abubakirov Triterpene glycosides of Silphium perfoliatum III. Structure of Silphioside E Chem. Nat. Compd. 20 1984 708 710
9. E.S. Davidyants, Zh.M. Putieva, V.A. Bandyukova, and N.K. Abubakirov Triterpene glycosides of Silphium perfoliatum V. Structure of Silphioside A Chem. Nat. Compd. 22 1986 58 60
10. E.S. Davidyants, Zh.M. Putieva, A.S. Shashkov, V.A. Bandyukova, and N.K. Abubakirov Triterpene glycosides of Silphium perfoliatum IV. Structure of Silphioside C Chem. Nat. Compd. 21 1985 486 489
11. 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
12. N. De Tommasi, S. Piacente, E. Gacs-Baitz, F. De Simone, C. Pizza, and R. Aquino Triterpenoid saponins from Spergularia ramosa J. Nat. Prod. 61 1998 323 327
13. N.H. El-Sayed, M. Wojcinska, K. Drost-Karbowska, J. Williams, and T.J. Mabry Kaempferol triosides from Silphium perfoliatum Phytochemistry 60 2002 835 838
14. D. Gulcemal, M. Masullo, E. Bedir, M. Festa, T. Karayildirim, O. Alankus-Caliskan, and S. Piacente Triterpene glycosides from Astragalus angustifolius Planta Med. 78 2012 720 729
15. D. Gulcemal, M. Masullo, A. Napolitano, T. Karayildirim, E. Bedir, O. Alankus-Caliskan, and S. Piacente Oleanane glycosides from Astragalus tauricolus: isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling Phytochemistry 86 2013 184 194
16. P.H. Hamel, and M.U. Chiltoskey Cherokee Plants and their Uses: A Four Hundred Year History 1975 Herald Publishing Co. North Carolina
17. R. Kowalski Studies of selected plant raw materials as alternative sources of triterpenes of oleanolic and ursolic acid types J. Agric. Food Chem. 55 2007 656 662
18. R. Kowalski, and T. Wolski TLC and HPLC analysis of the phenolic acids in Silphium perfoliatum L. leaves, inflorescences and rhizomes J. Planar Chromatogr. Mod. TLC 16 2003 230 236
19. 13C NMR Spectra of pentacyclic triterpenoids - a complication and some salient features Phytochemistry 37 1994 1517 1575
20. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
21. L. Quijano, T. Rios, F.R. Fronczek, and N.H. Fischer The molecular structure of maniladiol from Baccharis salicina Phytochemistry 49 1998 2065 2068
22. L.T.K. Van, T.M. Hung, P.T. Thuong, T.M. Ngoc, J.C. Kim, H. Jang, X.F. Cai, Sei.R. Oh, B. Min, and M.H. Woo Oleanane-type triterpenoids from Aceriphyllum rossii and their cytotoxic activity J. Nat. Prod. 72 2009 1419 1423
23. J. Wandji, F. Tillequin, D.A. Mulholland, J.C. Shirri, N. Tsabang, E. Seguin, P. Verite, F. Libot, and Z.T. Fomuma Pentacyclic triterpenoid and saponins from Gambeya boukokoensis Phytochemistry 64 2003 845 849
24. R. Kowalski, and T. Wolski The chemical composition of essential oils of Silphium perfoliatum L Flavour Frag. J. 20 2005 306 310
25. M.J. Pcolinski, R.W. Doskotch, A.Y. Lee, and J. Clardy Chlorosilphanol and silphanepoxol, labdane diterpenes from Silphium perfoliatum J. Nat. Prod. 57 1994 776 783
26. V.N. Syrov, Z.A. Khushbaktova, and E.S. Davidyants Triterpenic glycosides from Silphium perfoliatum L. Hypolipidemic activity of silphioside Khim. Farm. Zhurnal 26 1992 66 69
27. K.-W. Wang, H.-X. Sun, B. Wu, and Y.-J. Pan Two novel olean triterpenoids from Celastrus hypoleucus Helv. Chim. Acta 88 2005 990 995
28. J.D. Williams, M. Wojcińska, L.M. Calabria, K. Linse, J.A. Clevinger, and T.J. Mabry The flavonoids and phenolic acids of the genus Silphium and their chemosystematic value Nat. Prod. Commun. 4 2009 435 446
29. M. Wojcińska, J.D. Williams, T.J. Mabry, A. Ahmed, B.D. Davis, G. Toth, N. El-Sayed, I. Matlawska, and J. Clevinger Flavonol triglycosides from the leaves of Silphium albiflorum Nat. Prod. Commun. 1 2006 941 948