Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia.
Two new oleanane-type triterpene saponins, adianthifoliosides A (1) and B (2), were isolated from a 95% ethanolic extract of roots of Albizia adianthifolia. Their structures were elucidated mainly by using a combination of 600 MHz 1D and 2D NMR techniques (COSY, NOESY, TOCSY, HSQC, and HMBC) and by FABMS and HRESIMS. Compounds 1 and 2 were characterized as glycosides of acacic acid acylated by an o-hydroxybenzoyl unit. The crude saponin mixture (CSM), compounds 1 and 2 together with 3 and 4 (prosapogenins obtained from the mild alkaline hydrolysate of the CSM), were evaluated for immunomodulatory activity on the Jurkat T cell line and for hemolytic property against sheep erythrocytes. Compound 2 and, to a lesser extent, 1 and 3 were found to exhibit a dose-dependent immunomodulatory effect in the concentration range 10(-2)-10 microM, whereas 4 showed a lymphoproliferative activity in the same concentration range. Among the compounds tested, only 1 and 2 were found to be hemolytic.
Haddad
Mohamed
M
Laboratoire de Pharmacognosie, Unité MIB JE 2244, Faculté de Pharmacie, Université de Bourgogne, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
Miyamoto
Tomofumi
T
Laurens
Véronique
V
Lacaille-Dubois
Marie-Aleth
MA
D000107:Acetylation; D000276:Adjuvants, Immunologic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031289:Albizzia / Q000737:chemistry*; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007560:Cote d'Ivoire; D004305:Dose-Response Relationship, Drug; D004912:Erythrocytes / Q000187:drug effects; D006461:Hemolysis; D006801:Humans; D019169:Jurkat Cells / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D020156:Salicylic Acid; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012756:Sheep; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000276:Adjuvants, Immunologic; D000972:Antineoplastic Agents, Phytogenic; D012503:Saponins; D014315:Triterpenes; C476666:adianthifolioside A; C476667:adianthifolioside B; D009828:Oleanolic Acid; D020156:Salicylic Acid