Structural organization of cycloartane-based saponins in the genus Astragalus (Fabaceae)

  • Abir Sarraj-Laabidi
  • Marie-Aleth Lacaille-Dubois
  • Nabil Semmar
Article
  • 69 Downloads

Abstract

Cycloartane represents the most common aglycone in saponins of Astragalus genus. These saponins revealed high structural diversity through continuous elucidation of new molecules. Traditionally, saponins’ diversity was updated through reviews listing molecules with respect to their pharmacological activities and/or producing plant species. Beyond the long lists of reviewed molecules, this work provides statistical classification of 178 Astragalus saponins published between 1983 and 2014, leading to different molecular clusters grouping structurally close saponins and separating dissimilar ones. Clustering highlighted hierarchical factors governing structural diversification of cycloartane-based saponins in Astragalus, including rare aglycone forms, rare substitution positions and relative substitution levels of the carbon C3. Rare cycloartane forms were due to different epoxydations occurring at different degrees and positions in the lateral part of cycloartane. In common cycloartane forms, rare saponins were due to rare substituted positions consisting of atypical hydroxylations. Within the most common saponins, several classes were highlighted by the variations of C3-substitution levels in both epoxydated and not epoxydated cycloartane. Structural variations within and between saponin classes provided a strong basis for highlighting significant effects of cycloartane forms and C3-substitution levels on molecular ramification, elongation levels and substitution types (glycosylation and acetylation). Finally, these two key structural factors seemed to influence compartmental distribution of saponins in Astragalus genus.

Keywords

Desmosylation Diversification ways Glycosylation Molecular distribution Structural classification 

List of abbreviations

Ac

Acetic acid

Api

Apiose

Ara

Arabinose

CA

Correspondence analysis

D

Desmosylation

Ep

20,24-Epoxycycloartane

G

Glycosylation

Glc

Glucose

GlcA

Glucuronic acid

HCA

Hierarchical cluster analysis

LCh

Aliphatic lateral chain

MW

Mann–Whitney

PCs

Principal components

pi

Electronic double bond

Rha

Rhamnose

SG

Saponin group

Xyl

Xylose

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© Springer Science+Business Media B.V. 2017

Authors and Affiliations

  • Abir Sarraj-Laabidi
    • 1
    • 3
  • Marie-Aleth Lacaille-Dubois
    • 2
  • Nabil Semmar
    • 1
  1. 1.Laboratory of BioInformatics, BioMathematics and BioStatistics (BIMS), Pasteur Institute of TunisUniversity of Tunis El ManarTunisTunisia
  2. 2.Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR Sciences de SantéUniversité de Bourgogne Franche-ComtéDijon CedexFrance
  3. 3.Faculté des Sciences de TunisUniversité de Tunis El ManarTunisTunisia

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