Journal of Natural Medicines

, Volume 71, Issue 1, pp 50–58 | Cite as

Structure and hemolytic activity relationships of triterpenoid saponins and sapogenins

  • Nhu Ngoc Quynh Vo
  • Ery Odette Fukushima
  • Toshiya Muranaka
Original Paper


We evaluated the hemolytic activity of 41 commercially available triterpenoid saponins and sapogenins derived from three types of structural skeletons. Structure–activity relationships were established by comparing the structural characteristics of both the aglycone and sugar moieties among the tested compounds. The majority of oleanane-type sapogenins had stronger hemolytic effects than those of the ursane and dammarane types. The presence of polar regions on sapogenins, such as a carboxyl (COOH) at position 28, an α-hydroxyl (α-OH) at position 16, and/or a β-hydroxyl (β-OH) at position 2, significantly enhanced hemolysis. Meanwhile, the introduction of an α-OH at position 2 or a methyl hydroxyl (CH2OH) at positions 23 or 24 was closely associated with reduced activity. Our findings suggest that not only the complexity of sugar moieties but also the types and stereochemical configurations of functional groups at different positions, as well as the skeleton types, are important structural features affecting hemolytic potential. Our results provide a baseline in terms of the toxicity of saponins and sapogenins to erythrocytes, which holds promise for drug development.


Hemolytic activity Structure–activity relationships Hemolytic time course Triterpene saponins and sapogenins 



This study was partially supported by a Frontier Research Base for Global Young Researchers, Osaka University, from the Ministry of Education, Culture, Sports, Science, and Technology of Japan (MEXT) to E.O.F.; and the Monbukagakusho Scholarship to N.N.Q.V.

Compliance with ethical standards

Conflict of interest

The authors have no financial or commercial conflicts of interest.

Supplementary material

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Supplementary material 1 (XLSX 12 kb)
11418_2016_1026_MOESM2_ESM.xlsx (14 kb)
Supplementary material 2 (XLSX 14 kb)


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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2016

Authors and Affiliations

  • Nhu Ngoc Quynh Vo
    • 1
  • Ery Odette Fukushima
    • 1
    • 2
  • Toshiya Muranaka
    • 1
  1. 1.Department of Biotechnology, Graduate School of EngineeringOsaka UniversitySuitaJapan
  2. 2.Center for Open Innovation Research and Education, Graduate School of EngineeringOsaka UniversitySuitaJapan

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