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. 2022 Mar 2;20(3):186.
doi: 10.3390/md20030186.

New Metabolites from the Marine Sponge Scopalina hapalia Collected in Mayotte Lagoon

Charifat Saïd Hassane  1 , Gaëtan Herbette  2 , Elnur Garayev  3 , Fathi Mabrouki  3 , Patricia Clerc  1 , Nicole J de Voogd  4   5 , Stephane Greff  3 , Ioannis P Trougakos  6 , Jamal Ouazzani  7 , Mireille Fouillaud  1 , Laurent Dufossé  1 , Béatrice Baghdikian  3 , Evelyne Ollivier  3 , Anne Gauvin-Bialecki  1
Affiliations

New Metabolites from the Marine Sponge Scopalina hapalia Collected in Mayotte Lagoon

Charifat Saïd Hassane et al. Mar Drugs. .

Abstract

The biological screening of 44 marine sponge extracts for the research of bioactive molecules, with potential application in the treatment of age-related diseases (cancer and Alzheimer's disease) and skin aging, resulted in the selection of Scopalina hapalia extract for chemical study. As no reports of secondary metabolites of S. hapalia were found in the literature, we undertook this research to further extend current knowledge of Scopalina chemistry. The investigation of this species led to the discovery of four new compounds: two butenolides sinularone J (1) and sinularone K (2), one phospholipid 1-O-octadecyl-2-pentanoyl-sn-glycero-3-phosphocholine (3) and one lysophospholipid 1-O-(3-methoxy-tetradecanoyl)-sn-glycero-3-phosphocholine (4) alongside with known lysophospholipids (5 and 6), alkylglycerols (7-10), epidioxysterols (11 and 12) and diketopiperazines (13 and 14). The structure elucidation of the new metabolites (1-4) was determined by detailed spectroscopic analysis, including 1D and 2D NMR as well as mass spectrometry. Molecular networking was also explored to complement classical investigation and unravel the chemical classes within this species. GNPS analysis provided further information on potential metabolites with additional bioactive natural compounds predicted.

Keywords: Scopalina hapalia; bromotyrosine; butenolides; diketopiperazines; lipids; molecular networking.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of new (1–4) and known (5–14) metabolites isolated from Scopalina hapalia.
Figure 2
Figure 2
Key COSY (bold bonds) and HMBC (blue arrows) correlations for compound 1.
Figure 3
Figure 3
HMBC (blue arrows) correlations for compound 2.
Figure 4
Figure 4
Key COSY (bold bonds) and HMBC (blue arrows) correlations for compound 3.
Figure 5
Figure 5
Key COSY (bold bonds) correlation for compound 4.
Figure 6
Figure 6
(A) Molecular Network constructed using MS/MS data from fractions of Scopalina hapalia, obtained after the removal of non-polar lipids of organic crude extract, with a cosine similarity cutoff of 0.7. Edge thickness corresponds to relative cosine score similarity between nodes. Annotated clusters are enlarged. (B) Cluster MN1 based on compounds 1 and 2 (octagonal nodes) related to butenolide derivatives. (C) Cluster MN2 and MN3 related to bromotyrosine metabolites.
See this image and copyright information in PMC

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