Abstract
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.
MeSH terms
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Acetylation
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Adjuvants, Immunologic / chemistry
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Adjuvants, Immunologic / isolation & purification*
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Adjuvants, Immunologic / pharmacology
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Albizzia / chemistry*
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Animals
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology
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Cote d'Ivoire
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Dose-Response Relationship, Drug
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Erythrocytes / drug effects
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Hemolysis
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Humans
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Jurkat Cells / drug effects
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oleanolic Acid / analogs & derivatives
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Oleanolic Acid / chemistry
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Oleanolic Acid / isolation & purification*
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Oleanolic Acid / pharmacology
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Plant Roots / chemistry
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Plants, Medicinal / chemistry*
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Salicylic Acid
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Saponins / chemistry
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Saponins / isolation & purification*
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Saponins / pharmacology
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Sheep
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Triterpenes / chemistry
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Triterpenes / isolation & purification*
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Triterpenes / pharmacology
Substances
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Adjuvants, Immunologic
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Antineoplastic Agents, Phytogenic
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Saponins
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Triterpenes
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adianthifolioside A
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adianthifolioside B
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Oleanolic Acid
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Salicylic Acid