Analysis of Marine Natural Products Using Hyphenated Techniques

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (30 September 2021) | Viewed by 6119

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Fundación MEDINA, Avda del Conocimiento 34, Parque Tecnológico Ciencias Salud, E-18016 Granada, Spain
Interests: chromatography; mass spectrometry; liquid chromatography; natural product chemistry; nuclear magnetic resonance; bioactivity; medicinal chemistry; NMR structure elucidation; LC-MS/MS; MIC; compound isolation; structure elucidation; natural products; metabolite identification; alkaloids; pharmacognosy; bioassays; HPLC-UV; bioactive secondary metabolites; marine natural products
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Special Issue Information

Dear Colleagues,

Hyphenated techniques in the context of natural product chemistry refer to the coupling of a chromatographic and a spectral/spectroscopic technique for the analysis of extracts or complex mixtures of natural compounds. Recent advances in this field, mainly associated with the development of ultra-fast HPLC separation equipment and last generation mass spectrometry and NMR instruments have remarkably widened the use of these techniques in the marine natural products field. The development of algorithms and platforms for the analysis of data originated from these sources, such as the Global Natural Products Social molecular networking (GNPS) or the Small Molecular Accurate Recognition Technology (SMART) has notably enhanced the efficient exchange of data, establishing a community of users, and allowing the propagation of information that eventually can lead to the discovery of new bioactive molecules. Chemical dereplication, chemotaxonomic studies, chemical finger-printing, metabolomic studies, molecular networking, microbial community interactions, biosynthetic pathways, partial identification of compounds, and isolation of bioactive natural products constitute specific examples of tasks that can be successfully accomplished using these techniques and platforms. This Special Issue is intended as a comprehensive recompilation of articles that cover the application of hyphenated techniques and their associated platforms in all the aspects referred to above, in the context of marine research, with a special focus on applications related to the discovery of new marine bioactive compounds.


Dr. Fernando Reyes
Guest Editor

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Keywords

  • Hyphenated techniques
  • LC/MS
  • LC/NMR
  • Marine natural products
  • Bioactive compounds

Published Papers (2 papers)

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17 pages, 4653 KiB  
Article
Molecular Networking-Guided Isolation of New Etzionin-Type Diketopiperazine Hydroxamates from the Persian Gulf Sponge Cliona celata
by Reza Mohsenian Kouchaksaraee, Fengjie Li, Melika Nazemi, Mahdi Moridi Farimani and Deniz Tasdemir
Mar. Drugs 2021, 19(8), 439; https://doi.org/10.3390/md19080439 - 31 Jul 2021
Cited by 7 | Viewed by 3129
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 [...] Read more.
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 13 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. Full article
(This article belongs to the Special Issue Analysis of Marine Natural Products Using Hyphenated Techniques)
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10 pages, 793 KiB  
Article
Analysis of the Mycosporine-Like Amino Acid (MAA) Pattern of the Salt Marsh Red Alga Bostrychia scorpioides
by Maria Orfanoudaki, Anja Hartmann, Julia Mayr, Félix L. Figueroa, Julia Vega, John West, Ricardo Bermejo, Christine Maggs and Markus Ganzera
Mar. Drugs 2021, 19(6), 321; https://doi.org/10.3390/md19060321 - 31 May 2021
Cited by 5 | Viewed by 2347
Abstract
This study presents the validation of a high-performance liquid chromatography diode array detector (HPLC-DAD) method for the determination of different mycosporine-like amino acids (MAAs) in the red alga Bostrychia scorpioides. The investigated MAAs, named bostrychines, have only been found in this specific [...] Read more.
This study presents the validation of a high-performance liquid chromatography diode array detector (HPLC-DAD) method for the determination of different mycosporine-like amino acids (MAAs) in the red alga Bostrychia scorpioides. The investigated MAAs, named bostrychines, have only been found in this specific species so far. The developed HPLC-DAD method was successfully applied for the quantification of the major MAAs in Bostrychia scorpioides extracts, collected from four different countries in Europe showing only minor differences between the investigated samples. In the past, several Bostrychia spp. have been reported to include cryptic species, and in some cases such as B. calliptera, B. simpliciuscula, and B. moritziana, the polyphyly was supported by differences in their MAA composition. The uniformity in the MAA composition of the investigated B. scorpioides samples is in agreement with the reported monophyly of this Bostrychia sp. Full article
(This article belongs to the Special Issue Analysis of Marine Natural Products Using Hyphenated Techniques)
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