Structure Elucidation of New Acetylated Saponins, Lessoniosides A, B, C, D, and E, and Non-Acetylated Saponins, Lessoniosides F and G, from the Viscera of the Sea Cucumber Holothuria lessoni
by
Yadollah Bahrami 1,2,3,4,* and Christopher M. M. Franco 1,2,3,*
Yadollah Bahrami 1,2,3,4,* and Christopher M. M. Franco 1,2,3,*
1
Medical Biotechnology, Flinders Medical Science and Technology, School of Medicine, Flinders University, Adelaide SA 5042, Australia
2
Centre for Marine Bioproducts Development, Flinders University, Adelaide SA 5042, Australia
3
Australian Seafood Cooperative Research Centre, Mark Oliphant Building, Science Park, Adelaide SA 5042, Australia
4
Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah 6714415185, Iran
*
Authors to whom correspondence should be addressed.
Academic Editor: Alejandro M. Mayer
Mar. Drugs 2015, 13(1), 597-617; https://doi.org/10.3390/md13010597
Received: 8 August 2014 / Accepted: 1 January 2015 / Published: 16 January 2015
(This article belongs to the Special Issue Marine Bioactive Natural Product Studies—A Southern Hemisphere Perspective)
Sea cucumbers produce numerous compounds with a wide range of chemical structural diversity. Among these, saponins are the most diverse and include sulfated, non-sulfated, acetylated and methylated congeners with different aglycone and sugar moieties. In this study, MALDI and ESI tandem mass spectrometry, in the positive ion mode, were used to elucidate the structure of new saponins extracted from the viscera of H. lessoni. Fragmentation of the aglycone provided structural information on the presence of the acetyl group. The presence of the O-acetyl group was confirmed by observing the mass transition of 60 u corresponding to the loss of a molecule of acetic acid. Ion fingerprints from the glycosidic cleavage provided information on the mass of the aglycone (core), and the sequence and type of monosaccharides that constitute the sugar moiety. The tandem mass spectra of the saponin precursor ions [M + Na]+ provided a wealth of detailed structural information on the glycosidic bond cleavages. As a result, and in conjunction with existing literature, we characterized the structure of five new acetylated saponins, Lessoniosides A–E, along with two non-acetylated saponins Lessoniosides F and G at m/z 1477.7, which are promising candidates for future drug development. The presented strategy allows a rapid, reliable and complete analysis of native saponins.
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Keywords:
sea cucumber; viscera; saponins; mass spectrometry; MALDI; ESI; HPCPC; triterpene glycosides; structure elucidation; bioactive compounds; marine invertebrate; Echinodermata; holothurian
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MDPI and ACS Style
Bahrami, Y.; Franco, C.M.M. Structure Elucidation of New Acetylated Saponins, Lessoniosides A, B, C, D, and E, and Non-Acetylated Saponins, Lessoniosides F and G, from the Viscera of the Sea Cucumber Holothuria lessoni. Mar. Drugs 2015, 13, 597-617.
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