Bahrami Y et al. (2018), Distribution of Saponins in the Sea Cucumber Ho...

ECB-ART-46728

Mar Drugs 2018 Nov 01;1611:. doi: 10.3390/md16110423.

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Distribution of Saponins in the Sea Cucumber Holothuria lessoni; the Body Wall Versus the Viscera, and Their Biological Activities.

Bahrami Y , Zhang W , M M Franco C .

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Sea cucumbers are an important ingredient of traditional folk medicine in many Asian countries, which are well-known for their medicinal, nutraceutical, and food values due to producing an impressive range of distinctive natural bioactive compounds. Triterpene glycosides are the most abundant and prime secondary metabolites reported in this species. They possess numerous biological activities ranging from anti-tumour, wound healing, hypolipidemia, pain relieving, the improvement of nonalcoholic fatty livers, anti-hyperuricemia, the induction of bone marrow hematopoiesis, anti-hypertension, and cosmetics and anti-ageing properties. This study was designed to purify and elucidate the structure of saponin contents of the body wall of sea cucumber Holothurialessoni and to compare the distribution of saponins of the body wall with that of the viscera. The body wall was extracted with 70% ethanol, and purified by a liquid-liquid partition chromatography, followed by isobutanol extraction. A high-performance centrifugal partition chromatography (HPCPC) was conducted on the saponin-enriched mixture to obtain saponins with a high purity. The resultant purified saponins were analyzed using MALDI-MS/MS and ESI-MS/MS. The integrated and hyphenated MS and HPCPC analyses revealed the presence of 89 saponin congeners, including 35 new and 54 known saponins, in the body wall in which the majority of glycosides are of the holostane type. As a result, and in conjunction with existing literature, the structure of four novel acetylated saponins, namely lessoniosides H, I, J, and K were characterized. The identified triterpene glycosides showed potent antifungal activities against tested fungi, but had no antibacterial effects on the bacterium Staphylococcus aureus. The presence of a wide range of saponins with potential applications is promising for cosmeceutical, medicinal, and pharmaceutical products to improve human health.

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Genes referenced: agl LOC100887844

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References [+] :

Almuzara, In vitro susceptibility of Achromobacter spp. isolates: comparison of disk diffusion, Etest and agar dilution methods. 2010, Pubmed

	Figure 1. The thin-layer chromatography (TLC) pattern of the high-performance centrifugal partition chromatography (HPCPC) fractions from the purified extracts of the body wall of the H. lessoni sea cucumber using the lower phase of the CHCl3â€“MeOHâ€“H2O (7:13:8) system. The numbers under each lane indicate the fraction number in the fraction collector. The Fractions 89 to 102 of one analysis (of 130 fractions) are shown. Lane 1 is the saponin enriched iso-butanol extract.
	Figure 2. The matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) fingerprint of saponin enriched iso-butanol extract over the mass range of 950â€“1550 m/z from the body wall of H. lessoni.
	Figure 3. The MALDI-MS fingerprint of Fraction 110. The major peak at m/z 1141.7 corresponded to Desholothurin A.
	Figure 4. The electrospray ionization mass spectrometry (ESI-MS) spectrum of Fraction 110. The major peaks corresponded to Desholothurin A.
	Figure 5. The structures of some of the newly identified saponins from the body wall of H. lessoni, as representative.
	Figure 6. The saponin profile of Fraction 110 by ESI-MS in both the positive (a,b) and negative (c) ion modes. The 24 u or Da mass discrepancy between the positive and negative ion modes for an individual ion indicates the compound is non-sulphated saponin.
	Figure 7. The MALDI-MS/MS profile of the ions at m/z 1141 from Fraction 55 corresponding to desholothurin A1. The sequential losses of aglycone (Agl), Xyl, MeGlc, Glc, and Glc residues yielded the product ions at m/z 673, 523, 347, and 185, respectively. However, the ion peaks at m/z 507 and 657 corresponded to the sodiated key diagnostic peak [MeGlc-Glc-Qui + Na]+, and the entire sodiated hydrated sugar residues [MeGlc-Glc-Qui-Xyl + H2O + Na]+ of desholothurin A, respectively.
	Figure 8. (+) The ESI-MS/MS spectra of the ions at m/z 1141.7 in Fractions 55 (top) and 110 (bottom). The figure indicates the presence of isomeric compounds. The key diagnostic peak at m/z 523 corresponding to [MeGlc-Glc-Glc + Na]+ revealed the structure of desholothurin A1, while the key diagnostic peak at m/z 507 corresponding to [MeGlc-Glc-Qui + Na]+ indicted the structure of esholothurin A. The peak at m/z 481.2 corresponds to [Glc-Qui-Xyl + Na + H2O].
	Figure 9. The positive ion mode ESI-MS/MS spectrum of ions detected at m/z 1461.7 from Fraction 95. The spectrum reveals the presence of different aglycones and sugar residues in the isomeric saponins. The full and dotted arrows demonstrate the three main feasible fragmentation pathways. The fragmentation pattern of ions at m/z 1461.7 reveals the structure of acetylated saponins lessoniosides H and K as a representative. The blue arrows show the decomposition of the isomeric congeners Lessonioside H, whereas the green arrows indicate the fragmentation patterns of lessonioside K. The loss of the acetoxy group from the ions at m/z 511.2 generates ions at m/z 451.2, which corresponds to hydrated three sugar units [Xyl-Xyl-MeXyl + H2O + Na].
	Figure 10. The ESI-MS/MS spectrum of desholothurin A in the negative ion mode.
	Figure 11. (+) MALDI spectra of butanolic saponin-enriched extract from viscera (a) and body wall (b) of H. lessoni.