A new complex triterpenoid saponin from Samanea saman with haemolytic activity and adjuvant effect

Phytochemistry Letters

Volumn 5, Issue 3, 2012, Pages 626-631

  Barbosa, Antony De Paula ^a   Da Silva, Bernadete Pereira ^a   Parente, José Paz ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Adjuvant effect; Complex triterpenoid saponin; Haemolytic activity; Leguminosae; Samanea saman

Indexed keywords

HEMOLYTIC AGENT; OVALBUMIN; QS 21; TRITERPENOID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BARK; CARBON NUCLEAR MAGNETIC RESONANCE; CELLULAR IMMUNITY; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; IN VITRO STUDY; LEGUME; MALE; MOUSE; NONHUMAN; PLANT STEM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUILLAJA; QUILLAJA SAPONARIA; SAMANEA SAMAN; SOLVENT EXTRACTION;

FABACEAE; SAMANEA SAMAN;

EID: 84864965661     PISSN: 18743900     EISSN: 18767486     Source Type: Journal    
DOI: 10.1016/j.phytol.2012.06.009     Document Type: Article

References (27)

1. V.H. Castro, E. Ramirez, G.A. Mora, Y. Iwase, T. Nagao, H. Okabe, H. Matsunaga, M. Katano, and M. Mori Structures and antiproliferative activity of saponins from Sechium pittieri and S. talamancense Chem. Pharm. Bull. 45 1997 349 358 (Pubitemid 27131862)
2. P.A. Durr The biology, ecology and agroforestry potential of the raintree, Samanea saman (Jacq.) Merr Agroforest. Syst. 51 2001 223 237 (Pubitemid 32328996)
3. 5, from Castanospermum australe Cunn. et Fras Aust. J. Chem. 16 1963 900 905
4. T. Fujioka, M. Iwamoto, Y. Iwase, S. Hachiyama, H. Okabe, T. Yamauchi, and K. Mihashi Studies on the constituents of Actinostema lobatum Maxim. V. Structures of lobatosides B, E, F and G, the dicrotalic acid esters of bayogenin bisdesmosides isolated from the herb Chem. Pharm. Bull. 37 1989 2355 2360
5. G.J. Gerwig, J.P. Kamerling, and J.F.G. Vliegenthart Determination of the D and L configuration of neutral monosaccharides by high-resolution capillary G.L.C Carbohydr. Res. 62 1978 349 357
6. ILDIS International Legume Database & Information Service, 2005. http://www.ildis.org/LegumeWeb?version∼10.01&LegumeWeb&tno∼ 158&genus∼Albizia&species∼saman#151.
7. J.P. Kamerling, G.J. Gerwig, J.F.G. Vliegenthart, and J.R. Clamp Characterization by gas-liquid chromatography-mass spectrometry and proton-magnetic-resonance spectroscopy of pertrimethylsilyl methyl glycosides obtained in the methanolysis of glycoproteins and glycopeptides Biochem. J. 151 1975 491 495
8. Y.-J. Kim, P. Wang, M. Navarro-Villalobos, B.D. Rohde, J.M. Derryberry, and D.Y. Gin Synthetic Studies of Complex Immunostimulants from Quillaja saponaria: Synthesis of the Potent Clinical Immunoadjuvant QS-21Aapi J. Am. Chem. Soc. 128 2006 11906 11915 (Pubitemid 44360227)
9. M.A. Lacaille-Dubois, and H. Wagner A review of the biological and pharmacological activities of saponins Phytomedicine 2 1996 363 383
10. S.B. Mahato, and A.P. Kundu NMR spectra of pentacyclic triterpenoids - a compilation and some salient features Phytochemistry 35 1994 1515 1575
11. D.J. Marciani Vaccine adjuvants: role and mechanisms of action in vaccine immunogenicity Drug Discov. Today 8 2003 934 943 (Pubitemid 37230013)
12. A.M. Mowat, A.M. Donachie, G. Reid, and O. Jarrett Immune-stimulating complexes containing Quil A and protein antigen prime class I MHC-restricted T lymphocytes in vivo and are immunogenic by the oral route Immunology 72 1991 317 322
13. K. Oda, H. Matsuda, T. Murakami, S. Katayama, T. Ohgitani, and M. Yoshikawa Adjuvant and haemolytic activities of saponins derived from medicinal and food plants Biol. Chem. 381 2000 67 74 (Pubitemid 30102877)
14. Y. Okada, K. Koyama, K. Takahashi, T. Okuyama, and S. Shibata Gleditsia saponins I. Structures of monoterpene moieties of Gleditsia saponin C Planta Med. 40 1980 185 192 (Pubitemid 11160226)
15. J.P. Parente, P. Cardon, Y. Leroy, J. Montreuil, B. Fournet, and G. Ricart A convenient method for methylation of glycoprotein glycans in small amounts by using lithium methylsulfinyl carbanion Carbohydr. Res. 141 1985 41 47
16. R.N. Prasad, S. Viswanathan, J.R. Devi, V. Nayak, V.C. Swetha, B.R. Archana, N. Parathasarathy, and J. Rajkumar Preliminary phytochemical screening and antimicrobial activity of Samanea saman J. Med. Plant. Res. 2 2008 268 270
17. W.R. Santos, R.R. Bernardo, L.M.T. Peçanha, M. Palatnik, J.P. Parente, and C.B.P. de Sousa Haemolytic activities of plant saponins and adjuvants. Effect of Periandra mediterranea saponin on the humoral response to the FML antigen of Leishmania donovani Vaccine 15 1997 1024 1029 (Pubitemid 27308581)
18. J.S. Sawardeker, J.H. Sloneker, and A. Jeanes Quantitative determination of monosaccharides as their alditol acetates by gas liquid chromatography Anal. Chem. 37 1965 1602 1604
19. H.-X. Sun, Y. Xie, and Y.-P. Ye Advances in saponin-based adjuvants Vaccine 27 2009 1787 1796
20. N. Tan, J. Zhou, and S. Zhao Advances in structural elucidation of glucuronide oleanane-type triterpene carboxylic acid 3, 28-O-bidesmosides (1962-1997) Phytochemistry 52 1999 153 192 (Pubitemid 29426483)
21. A. Tava, M. Mella, P. Avato, M.P. Argentieri, Z. Bialy, and M. Jurzysta Triterpenoid glycosides from leaves of Medicago arborea L J. Agric. Food Chem. 53 2005 9954 9965 (Pubitemid 43081203)
22. D.C. Waite, E.W. Jacobson, F.A. Ennis, R. Edelman, B. White, R. Kammer, C. Anderson, and C.R. Kensil Three double-blind, randomized trials evaluating the safety and tolerance of different formulations of the saponin adjuvant QS-21 Vaccine 19 2001 3957 3967 (Pubitemid 32566320)
23. D. Zhang, T. Miyase, M. Kuroyanagi, K. Umehara, and A. Ueno Studies on the constituents of Polygala japonica Hout. I. Structures of polygalasaponins I-X Chem. Pharm. Bull. 43 1995 115 120
24. D. Zhang, T. Miyase, M. Kuroyanagi, K. Umehara, and A. Ueno Studies on the constituents of Polygala japonica Hout. II. Structures of polygalasaponins XI-XIV Chem. Pharm. Bull. 43 1995 966 970
25. Z. Zhang, K. Koike, Z. Jia, T. Nikaido, D. Guo, and J. Zheng Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis J. Nat. Prod. 62 1999 740 745 (Pubitemid 29259093)
26. Z. Zhang, K. Koike, Z. Jia, T. Nikaido, D. Guo, and J. Zheng Gleditsiosides N-Q, new triterpenoid saponins from Gleditsia sinensis J. Nat. Prod. 62 1999 877 881 (Pubitemid 29296327)
27. Z. Zhang, K. Koike, Z. Jia, T. Nikaido, D. Guo, and J. Zheng Triterpenoidal saponins acylated with two monoterpenic acids from Gleditsia sinensis Chem. Pharm. Bull. 47 1999 388 393 (Pubitemid 29166280)