TY - JOUR
T1 - Chemical fingerprinting and phylogenetic mapping of saponin congeners from three tropical holothurian sea cucumbers
AU - Bondoc, Karen Grace V
AU - Lee, Hyeyoung
AU - Cruz, Lourdes J.
AU - Lebrilla, Carlito B
AU - Juinio-Meñez, Marie Antonette
PY - 2013/11
Y1 - 2013/11
N2 - Holothurians are sedentary marine organisms known to produce saponins (triterpene glycosides), secondary metabolites exhibiting a wide range of biological activities. In this paper, we investigated the saponin contents of semi-purified and membranolytic HPLC fractionated extracts from the body wall of three species of Holothuriidae as an attempt to examine its chemical diversity in relation to phylogenetic data. MALDI-FTICR MS and nano-HPLC-chip Q-TOF MS were used for mass profiling and isomer separation, respectively giving a unique chemical saponin fingerprint. Moreover, the methods used yield the highest number of congeners. However, saponin concentration, bioactivity and chemical diversity had no apparent relationship. MS fingerprint showed the presence of holothurinosides, which was observed for the first time in other Holothuria genera besides the basally positioned Holothuria forskali. This congener is proposed to be a primitive character that could be used for taxonomic purposes. The phylogenetic mapping also showed that the glycone part of the compound evolved from non-sulfated hexaosides to sulfated tetraosides, which have higher membranolytic activity and hydrophilicity, the two factors affecting the total ecological activity (i.e. chemical defense) of these compounds. This might be an adaptation to increase the fitness of the organism.
AB - Holothurians are sedentary marine organisms known to produce saponins (triterpene glycosides), secondary metabolites exhibiting a wide range of biological activities. In this paper, we investigated the saponin contents of semi-purified and membranolytic HPLC fractionated extracts from the body wall of three species of Holothuriidae as an attempt to examine its chemical diversity in relation to phylogenetic data. MALDI-FTICR MS and nano-HPLC-chip Q-TOF MS were used for mass profiling and isomer separation, respectively giving a unique chemical saponin fingerprint. Moreover, the methods used yield the highest number of congeners. However, saponin concentration, bioactivity and chemical diversity had no apparent relationship. MS fingerprint showed the presence of holothurinosides, which was observed for the first time in other Holothuria genera besides the basally positioned Holothuria forskali. This congener is proposed to be a primitive character that could be used for taxonomic purposes. The phylogenetic mapping also showed that the glycone part of the compound evolved from non-sulfated hexaosides to sulfated tetraosides, which have higher membranolytic activity and hydrophilicity, the two factors affecting the total ecological activity (i.e. chemical defense) of these compounds. This might be an adaptation to increase the fitness of the organism.
KW - Chemical taxonomy
KW - Holothuriidae
KW - Mass spectrometry
KW - Phylogenetics
KW - Saponin
UR - http://www.scopus.com/inward/record.url?scp=84884970221&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84884970221&partnerID=8YFLogxK
U2 - 10.1016/j.cbpb.2013.09.002
DO - 10.1016/j.cbpb.2013.09.002
M3 - Article
C2 - 24036426
AN - SCOPUS:84884970221
VL - 166
SP - 182
EP - 193
JO - Comparative biochemistry and physiology. B, Comparative biochemistry
JF - Comparative biochemistry and physiology. B, Comparative biochemistry
SN - 1096-4959
IS - 3-4
ER -