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Mar Drugs
2020 Mar 31;184:. doi: 10.3390/md18040181.
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Anti-Fouling Effects of Saponin-Containing Crude Extracts from Tropical Indo-Pacific Sea Cucumbers.
Kamyab E
,
Goebeler N
,
Kellermann MY
,
Rohde S
,
Reverter M
,
Striebel M
,
Schupp PJ
.
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Sea cucumbers are bottom dwelling invertebrates, which are mostly found on subtropical and tropical sea grass beds, sandy reef flats, or reef slopes. Although constantly exposed to fouling communities in these habitats, many species are surprisingly free of invertebrate epibionts and microfouling algae such as diatoms. In our study, we investigated the anti-fouling (AF) activities of different crude extracts of tropical Indo-Pacific sea cucumber species against the fouling diatom Cylindrotheca closterium. Nine sea cucumber species from three genera (i.e., Holothuria, Bohadschia, Actinopyga) were selected and extracted to assess their AF activities. To verify whether the sea cucumber characteristic triterpene glycosides were responsible for the observed potent AF activities, we tested purified fractions enriched in saponins isolated from Bohadschia argus, representing one of the most active anti-fouling extracts. Saponins were quantified by vanillin-sulfuric acid colorimetric assays and identified by LC-MS and LC-MS/MS analyses. We were able to demonstrate that AF activities in sea cucumber extracts were species-specific, and growth inhibition as well as attachment of the diatom to surfaces is dependent on the saponin concentration (i.e., Actinopyga contained the highest quantities), as well as on the molecular composition and structure of the present saponins (i.e., Bivittoside D derivative was the most bioactive compound). In conclusion, the here performed AF assay represents a promising and fast method for selecting the most promising bioactive organism as well as for identifying novel compounds with potent AF activities for the discovery of potentially novel pharmacologically active natural products.
Figure 1. Structure of the saponin molecule âbivittoside Dâ, m/z 1449.687 [M + Na]+ [56], consisting of the glycone and aglycone moieties (produced with ChemDraw, version 16.0.1.4 (77)).
Figure 2. Phylogeny tree of the here studied sea cucumbers (CT = cuvierian tubule; adapted from [57,58,59,60].
Figure 3. Logarithmic response ratio (LRR) of C. closterium after exposure to three different concentrations (150, 15 and 1.5 µg mLâ1) of nine sea cucumber extracts in total (genera Holothuria, Bohadschia and Actinopyga) for (A) suspended cells in the water and (B) attached to the surface of the incubation flask. Significant differences compared to the control (CT = control) are shown in Table S1.
Figure 4. Cluster dendrogram of sea cucumber species based on their studied saponin and sapogenin compositions (âaverageâ distance type, log-transformed data, R version 1.2.5019).
Figure 5. Major saponin compounds detected in the studied sea cucumbers (peak area ⥠104). (A) saponin diversity and relative intensity and (B) sapogenin (aglycon) diversity and relative intensity. Sample codes represent exact mass (M in Da), and retention time (T in min). Different colors represent the presence of sulphate groups (in blue), non-sulphate groups (in black) and pure compounds (in purple and red). Bubble size correlates with differences in relative peak areas of the respective molecules.
Figure 6. Absolute saponin concentration of the tested crude extracts. (aâc) indicate significant differences between different sea cucumber crude extracts. KruskalâWallis, Dunnâs method as a multiple comparison test. Significance level at p < 0.05 was applied.
Figure 7. Logarithmic response ratio (LRR) of C. closterium following exposure to B. argus extract fractions in suspended cells in the water (A) and attached to the substrate (B). Fr.1 and Fr.2: impure, Fr. 3: semi-pure, Fr. 4: pure singular saponin species (bivittoside D-like). aâd represent result of Kruskal-Wallis test; p < 0.05.
Figure 8. (AâC). The test organism C. closterium under the microscope (A), culture flasks demonstrating high growth rates (left, not-inhibited), medium growth rates (middle) and low growth rates (inhibited) of C. closterium (B), growth curve of C. closterium in 7 days in the stock solution (C).
Figure 9. Flow chart showing the applied procedure for isolating the bioactive saponin compounds (Cutignano et al., 2015; Ebada et al., 2008 [99,100]). Sample set 1 and 2 refers to the samples that were tested for anti-fouling (AF) activity in this study.
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