Molecular Networking-Guided Isolation of New Etzionin-Type Diketopiperazine Hydroxamates from the Persian Gulf Sponge Cliona celata.

Mohsenian-Kouchaksaraee, Reza , Li, Fengjie , Nazemi, Melika, Farimani, Mahdi Moridi and Tasdemir, Deniz (2021) Molecular Networking-Guided Isolation of New Etzionin-Type Diketopiperazine Hydroxamates from the Persian Gulf Sponge Cliona celata. Open Access Marine Drugs, 19 (8). Art.Nr. 439. DOI 10.3390/md19080439.

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Abstract

The Persian Gulf is a unique and biologically diverse marine environment dominated by invertebrates. In continuation of our research interest in the chemistry and biological activity of marine sponges from the Persian Gulf, we selected the excavating sponge Cliona celata for detailed metabolome analyses, in vitro bioactivity screening, and chemical isolation studies. A UPLC-MS/MS (MS2) molecular-networking-based dereplication strategy allowed annotation and structural prediction of various diketopiperazines (DKPs) and etzionin-type diketopiperazine hydroxamates (DKPHs) in the crude sponge extract. The molecular-networking-guided isolation approach applied to the crude extract afforded the DKPH etzionin (1) and its two new derivatives, clioetzionin A (2) and clioetzionin B (3). Another new modified DKP (4) was identified by MS/MS analyses but could not be isolated in sufficient quantities to confirm its structure. The chemical characterization of the purified DKPHs 1–3 was performed by a combination of 1D and 2D NMR spectroscopy, HRMS, HRMS/MS, and [α]D analyses. Compounds 1 and 2 exhibited broad antibacterial, antifungal, and anticancer activities, with IC50 values ranging from 19.6 to 159.1 µM. This is the first study investigating the chemical constituents of a C. celata specimen from the Persian Gulf. It is also the first report of full spectroscopic data of etzionin based on extensive spectroscopic analyses

Document Type: Article
Keywords: Persian Gulf; marine sponge; Cliona celata; molecular networking; diketopiperazine; etzionin; clioetzionin A; clioetzionin B
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MN Marine natural products chemistry
Main POF Topic: PT6: Marine Life
Refereed: Yes
Open Access Journal?: Yes
Publisher: MDPI
Date Deposited: 02 Aug 2021 05:54
Last Modified: 07 Feb 2024 15:37
URI: https://oceanrep.geomar.de/id/eprint/53654

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