Glycosides of marine invertebrates. XXVI. Holothurin A from the Pacific Ocean holothurianHolothvria squamifera. Isolation of the native aglycone

Ivanova, N. S.; Smetanina, O. F.; Кузнецова, Т. А.

doi:10.1007/bf00574327

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“…Griseaside A A 8 m I C60H98O28 1266 grisea, lessoni W, V, BW (Sun et al 2008a;Bahrami et al 2014bBahrami et al , 2018 grisea, hilla, impatiens, lessoni, leucospilota, martensii, mexicana, moebii, nobilis, pervicax, polii, pulla, scabra, surinamensis, squamifera, tubulosa W, V, BW, CT (Elyakov et al 1973(Elyakov et al , 1975Kitagawa et al 1981;Kuznetsova et al 1982a;Ivanova et al 1984;Stonik 1986;Kobayashi et al 1991;Minh et al 2005;Thanh et al 2006;Weng et al 2007;Sun et al 2008b;Han et al 2009b;Van Dyck et al 2010b;Bondoc et al 2013;Bahrami et al 2014bBahrami et al , 2018Wang et al 2014;Yu et al 2015;Sangpairoj et al 2016 W, V, BW (Friess et al 1968;Kuznetsova et al 1982a;Kobayashi et al 1991;Radhika et al 2002;Minh et al 2005;Kalinin et al 2005;Han et al 2007Han et al , 2009bHan et al , 2010Bahrami et al 2014bBahrami et al , 2018Wang et al 2014;Yu et al 2015;...…”

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confidence: 99%

Holothuria triterpene glycosides: a comprehensive guide for their structure elucidation and critical appraisal of reported compounds

et al. 2021

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Sea cucumbers or holothurians are marine invertebrates, belonging to the phylum Echinodermata (kingdom Animalia). In Asia, they are commonly used as food, while they are applied in traditional medicine as well. A wide range of secondary metabolites from these animals has been reported, but triterpene glycosides are the most predominant and most studied and are considered as valuable chemotaxonomic markers. With respect to this, the genus Holothuria is an important genus of sea cucumbers, given the high number and variety of triterpene glycosides previously reported. Holothuria triterpene glycosides are typically composed of a 3β-hydroxyholost-9(11)-ene aglycon and a glycosidic moiety comprised of one up to six sugar units, connected to position 3 of the sapogenin. In the past decade (2010-2020) as much as 63 saponins were identified for the first time in the Holothuria genus, of which 36 had not been reported before. Identification was mainly carried out by LC-MS (liquid chromatographymass spectrometry) analysis, while also NMR (nuclear magnetic resonance) spectroscopy is often applied for structure elucidation. However, while carrying out a literature search on these compounds, various inconsistencies were observed. Therefore, this review intends to provide an overview of typical signals that can occur in NMR and MS data, accompanied with an extensive explanation of their interpretation, in order to facilitate any future research on identification/structure elucidation of Holothuria saponins. Moreover, the data published in the past decade were critically reviewed and various questionable results are discussed.

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