The isolation of water-soluble natural products – challenges, strategies and perspectives

Berlinck, Roberto G. S.; Crnkovic, Camila M.; Gubiani, Juliana R.; Bernardi, Darlon I.; Ióca, Laura P.; Quintana-Bulla, Jairo I

doi:10.1039/d1np00037c

Cited by 24 publications

(12 citation statements)

References 965 publications

(1,381 reference statements)

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“…Adsorption and concentration of dissolved metabolites in aqueous media are generally performed using solid-phase extraction cartridges, disks, or polymeric resins ( e.g. , Amberlite XAD). ,,,− These techniques are widely used to concentrate organic environmental pollutants from water. , In situ continuous and passive adsorption of metabolites from aqueous media is generally performed using polymeric resins. ,,,, As such, the resins XAD-7 and XAD-16 were used to adsorb metabolites released in an aquarium by the sponges Aplysilla rosea and Crambe crambe, respectively. In line with these studies, we developed our aquarium experiments using XAD-7, filled in an external cartridge directly connected to the aquarium pump (Figure A).…”

Section: Resultsmentioning

confidence: 99%

“… 47 , 48 In situ continuous and passive adsorption of metabolites from aqueous media is generally performed using polymeric resins. 25 , 26 , 45 , 47 , 49 As such, the resins XAD-7 and XAD-16 were used to adsorb metabolites released in an aquarium by the sponges Aplysilla rosea ( 24 ) and Crambe crambe , 26 respectively. In line with these studies, we developed our aquarium experiments using XAD-7, filled in an external cartridge directly connected to the aquarium pump ( Figure 1 A).…”

Section: Resultsmentioning

confidence: 99%

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Diving into the Molecular Diversity of Aplysina cavernicola’s Exometabolites: Contribution of Bromo-Spiroisoxazoline Alkaloids

et al. 2022

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Sponges are prolific producers of specialized metabolites with unique structural scaffolds. Their chemical diversity has always inspired natural product chemists working in drug discovery. As part of their metabolic filter-feeding activities, sponges are known to release molecules, possibly including their specialized metabolites. These released “Exo-Metabolites” (EMs) may be considered as new chemical reservoirs that could be collected from the water column while preserving marine biodiversity. The present work aims to determine the proportion and diversity of specialized EMs released by the sponge Aplysina cavernicola (Vacelet 1959). This Mediterranean sponge produces bromo-spiroisoxazoline alkaloids that are widely distributed in the Aplysinidae family. Aquarium experiments were designed to facilitate a continuous concentration of dissolved and diluted metabolites from the seawater around the sponges. Mass Spectrometry (MS)-based metabolomics combined with a dereplication pipeline were performed to investigate the proportion and identity of brominated alkaloids released as EMs. Chemometric analysis revealed that brominated features represented 12% of the total sponge’s EM features. Consequently, a total of 13 bromotyrosine alkaloids were reproducibly detected as EMs. The most abundant ones were aerothionin, purealidin L, aerophobin 1, and a new structural congener, herein named aplysine 1. Their structural identity was confirmed by NMR analyses following their isolation. MS-based quantification indicated that these major brominated EMs represented up to 1.0 ± 0.3% w/w of the concentrated seawater extract. This analytical workflow and collected results will serve as a stepping stone to characterize the composition of A. cavernicola’s EMs and those released by other sponges through in situ experiments, leading to further evaluate the biological properties of such EMs.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Diving into the Molecular Diversity of Aplysina cavernicola’s Exometabolites: Contribution of Bromo-Spiroisoxazoline Alkaloids

et al. 2022

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“…The isolation of phosphate ester containing secondary metabolites has steadily increased during the time span of this review but considering the polar nature of some of them it well may be that they have been overlooked during natural product discovery campaigns. 300 These phosphate-containing natural products are usually isolated as their salts, thus increasing their hydrophilicity, and often require reversed phase chromatography for their purification. Instability problems during isolation and purification of some of them also need to be considered.…”

Section: Final Remarksmentioning

confidence: 99%

The phosphate ester group in secondary metabolites

2022

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“…DVB was chosen due to its demonstrated capacity to adsorb a wide range of nonpolar and semipolar DOM or specialized EMs. 40,41 In Situ Experiments. Three types of underwater experiments were performed.…”

Section: The Paucity Of Availablementioning

confidence: 99%

In Situ Capture and Real-Time Enrichment of Marine Chemical Diversity

Mauduit,

Derrien,

Grenier

et al. 2023

ACS Cent. Sci.

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Analyzing the chemical composition of seawater to understand its influence on ecosystem functions is a long-lasting challenge due to the inherent complexity and dynamic nature of marine environments. Describing the intricate chemistry of seawater requires optimal in situ sampling. Here is presented a novel underwater hand-held solid-phase extraction device, I-SMEL (In Situ Marine moleculE Logger), which aims to concentrate diluted molecules from large volumes of seawater in a delimited zone targeting keystone benthic species. Marine benthic holobionts, such as sponges, can impact the chemical composition of their surroundings possibly through the production and release of their specialized metabolites, hence termed exometabolites (EMs). I-SMEL was deployed in a sponge-dominated Mediterranean ecosystem at a 15 m depth. Untargeted MS-based metabolomics was performed on enriched EM extracts and showed (1) the chemical diversity of enriched seawater metabolites and (2) reproducible recovery and enrichment of specialized sponge EMs such as aerothionin, demethylfurospongin-4, and longamide B methyl ester. These EMs constitute the chemical identity of each targeted species: Aplysina cavernicola, Spongia off icinalis, and Agelas oroides, respectively. I-SMEL concentrated sponge EMs from 10 L of water in a 10 min sampling time. The present proof of concept with I-SMEL opens new research perspectives in marine chemical ecology and sets the stage for further sustainable efforts in natural product chemistry.

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The isolation of water-soluble natural products – challenges, strategies and perspectives

Abstract: The isolation of water-soluble metabolites significantly diminished during the last decades. A comprehensive analysis on the isolation of hydrophilic natural products is discussed with a perspective for the future of natural product sciences.

Cited by 24 publications

References 965 publications

Diving into the Molecular Diversity of Aplysina cavernicola’s Exometabolites: Contribution of Bromo-Spiroisoxazoline Alkaloids

Diving into the Molecular Diversity of Aplysina cavernicola’s Exometabolites: Contribution of Bromo-Spiroisoxazoline Alkaloids

The phosphate ester group in secondary metabolites

In Situ Capture and Real-Time Enrichment of Marine Chemical Diversity

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