Mass Spectrometry-Based Integration and Expansion of the Chemical Diversity Harbored Within a Marine Sponge

The marine sponge of the genus Geodia, Jaspis, Rhabdastrella, and Stelletta are characterized chemically by a variety of isomalabaricane triterpenes. This class of compounds drew spotlights in marine lead discovery due to their profound anti-proliferative properties. Further research on exploring its chemical diversity led to the identifications of two new isomalabaricane-type triterpenes rhabdastin H (1) and rhabdastin I (2). Their structures were unraveled using a series of spectroscopic approaches. These isolates were found to exhibit unique structural features with the only reported tetrahydrofuran functionality among all marine-derived isomalabaricanes. Both compounds 1 and 2 showed activities against K562 (IC50 11.7 and 9.8 μM) and Molt4 (IC50 16.5 and 11.0 μM) leukemic cells in MTT cell proliferative assay.

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A Review on Microbial Surfactants: Production, Classifications, Properties and Characterization

Journal of Advances in Microbiology ◽

10.9734/jamb/2019/v18i330170 ◽

2019 ◽

pp. 1-22 ◽

Cited By ~ 1

Author(s):

Emmanuel Oliver Fenibo ◽

Salome Ibietela Douglas ◽

Herbert Okechukwu Stanley

Keyword(s):

Mass Spectrometry ◽

Liquid Chromatography ◽

Current Knowledge ◽

Agar Plate ◽

Immiscible Fluids ◽

Chemical Diversity ◽

Ionization Mass ◽

Screening Techniques ◽

Properties And Characterization ◽

Industrial Sectors

Surfactants are a surface-active group of molecular compounds with hydrophobic and hydrophilic moieties in one single molecule that distributes themselves between two immiscible fluids, reduce surface/ interfacial tensions and cause the solubility of non-polar compounds in polar solvents. Besides surface and interfacial activities, they display properties such as solubilization, detergency, lubrication, emulsification, stabilization and foaming capacity. Microbiologically derived surfactants are called biosurfactants. They are produced as either metabolic products or as the surface chemistry of an actual cell. The employment of screening techniques such as surface tension measurements, drop collapse test, oil spreading assay, emulsification index (%EI24), cetyltrimethylammonium bromide (CTAB)/methylene blue agar plate test and strain characterization. Others are analytical techniques including liquid chromatography-mass spectroscopy, thin layer chromatography, high-performance liquid chromatography, Fourier transform infrared spectroscopy, nuclear magnetic resonance, fast atom bombardment-mass spectrometry and electrospray ionization-mass spectrometry. These have led to the identification of biosurfactant producing microorganisms, properties and characterization of biosurfactants. Therefore, this review tends to provide the current knowledge of the screening techniques and chromatography/spectroscopic tools employed to study biosurfactants. Results from a detailed study of these tools can unveil new surfactant producing microorganism, decipher chemical diversity and multifunctional properties of biosurfactants critical for applications in diverse industrial sectors.

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Ircinal E, a New Manzamine Derivative from the Indonesian Marine Sponge Acanthostrongylophora ingens

Natural Product Communications ◽

10.1177/1934578x1501001136 ◽

2015 ◽

Vol 10 (11) ◽

pp. 1934578X1501001 ◽

Cited By ~ 2

Author(s):

Mousa AlTarabeen ◽

Georgios Daletos ◽

Weaam Ebrahim ◽

Werner E. G. Müller ◽

Rudolf Hartmann ◽

...

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

High Resolution ◽

Cell Line ◽

Marine Sponge ◽

High Resolution Mass Spectrometry ◽

Two Dimensional ◽

Meoh Extract ◽

L5178y Cell ◽

Resolution Mass

Chemical investigation of the MeOH extract of the sponge Acanthostrongylophora ingens afforded the new manzamine derivative ircinal E (1), in addition to six known metabolites (2–7). The structure of the new compound was unequivocally elucidated using one- and two-dimensional NMR spectroscopy, as well as high-resolution mass spectrometry. Compounds 1–6 exhibited strong to moderate cytotoxicity against the murine lymphoma L5178Y cell line with IC50 values ranging from 2.8 to 21.7 μM.

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New Diterpenes with a Fused 6-5-6-6 Ring System Isolated from the Marine Sponge-Derived Fungus Trichoderma harzianum

Marine Drugs ◽

10.3390/md17080480 ◽

2019 ◽

Vol 17 (8) ◽

pp. 480 ◽

Cited By ~ 2

Author(s):

Takeshi Yamada ◽

Ayano Fujii ◽

Takashi Kikuchi

Keyword(s):

Mass Spectrometry ◽

Marine Sponge ◽

Trichoderma Harzianum ◽

Fast Atom Bombardment ◽

2D Nmr ◽

Cd Spectroscopy ◽

Ring System ◽

Chemical Structures ◽

Modified Mosher’S Method ◽

Halichondria Okadai

New diterpenes, namely, trichodermanins F–H, with a fused 6-5-6-6 ring system were isolated from the fungus Trichoderma harzianum OUPS-111D-4 separated from a marine sponge Halichondria okadai. These chemical structures were elucidated by 1D and 2D NMR as well as high-resolution fast atom bombardment mass spectrometry (HRFABMS) spectral analyses. We established their absolute stereostructures by application of the modified Mosher’s method or circular dichroism (CD) spectroscopy. In addition, their cytotoxicities were assessed using several cancer cell lines, with 1 and 2 exhibiting modest activities.

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Identification and dereplication of endophytic Colletotrichum strains by MALDI TOF mass spectrometry and molecular networking

Scientific Reports ◽

10.1038/s41598-020-74852-w ◽

2020 ◽

Vol 10 (1) ◽

Author(s):

Morgane Barthélemy ◽

Vincent Guérineau ◽

Grégory Genta-Jouve ◽

Mélanie Roy ◽

Jérôme Chave ◽

...

Keyword(s):

Mass Spectrometry ◽

Chemical Study ◽

Chemical Diversity ◽

Biologically Active ◽

Ionization Time ◽

Ion Clusters ◽

Maldi Tof ◽

Flight Mass Spectrometry ◽

Palm Species ◽

Ethyl Acetate Extracts

AbstractThe chemical diversity of biologically active fungal strains from 42 Colletotrichum, isolated from leaves of the tropical palm species Astrocaryum sciophilum collected in pristine forests of French Guiana, was investigated. The collection was first classified based on protein fingerprints acquired by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) correlated with cytotoxicity. Liquid chromatography coupled to high-resolution tandem mass spectrometry (LC-HRMS/MS) data from ethyl acetate extracts were acquired and processed to generate a massive molecular network (MN) using the MetGem software. From five Colletotrichum strains producing cytotoxic specialized metabolites, we predicted the occurrence of peptide and cytochalasin analogues in four of them by MN, including a similar ion clusters in the MN algorithm provided by MetGem software. Chemoinformatics predictions were fully confirmed after isolation of three pentacyclopeptides (cyclo(Phe-Leu-Leu-Leu-Val), cyclo(Phe-Leu-Leu-Leu-Leu) and cyclo(Phe-Leu-Leu-Leu-Ile)) and two cytochalasins (cytochalasin C and cytochalasin D) exhibiting cytotoxicity at the micromolar concentration. Finally, the chemical study of the last active cytotoxic strain BSNB-0583 led to the isolation of four colletamides bearing an identical decadienamide chain.

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Multi-Omic Profiling of Melophlus Sponges Reveals Diverse Metabolomic and Microbiome Architectures that Are Non-overlapping with Ecological Neighbors

Marine Drugs ◽

10.3390/md18020124 ◽

2020 ◽

Vol 18 (2) ◽

pp. 124 ◽

Cited By ~ 2

Author(s):

Ipsita Mohanty ◽

Sheila Podell ◽

Jason S. Biggs ◽

Neha Garg ◽

Eric E. Allen ◽

...

Keyword(s):

Mass Spectrometry ◽

Natural Products ◽

Candidate Gene ◽

Marine Sponge ◽

Gene Clusters ◽

Marine Sponges ◽

Quantitative Comparison ◽

Filter Feeding ◽

Chemical Structures ◽

Ecological Relevance

Marine sponge holobionts, defined as filter-feeding sponge hosts together with their associated microbiomes, are prolific sources of natural products. The inventory of natural products that have been isolated from marine sponges is extensive. Here, using untargeted mass spectrometry, we demonstrate that sponges harbor a far greater diversity of low-abundance natural products that have evaded discovery. While these low-abundance natural products may not be feasible to isolate, insights into their chemical structures can be gleaned by careful curation of mass fragmentation spectra. Sponges are also some of the most complex, multi-organismal holobiont communities in the oceans. We overlay sponge metabolomes with their microbiome structures and detailed metagenomic characterization to discover candidate gene clusters that encode production of sponge-derived natural products. The multi-omic profiling strategy for sponges that we describe here enables quantitative comparison of sponge metabolomes and microbiomes to address, among other questions, the ecological relevance of sponge natural products and for the phylochemical assignment of previously undescribed sponge identities.

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Biological and Chemical Diversity of Marine Sponge-Derived Microorganisms over the Last Two Decades from 1998 to 2017

Molecules ◽

10.3390/molecules25040853 ◽

2020 ◽

Vol 25 (4) ◽

pp. 853 ◽

Cited By ~ 2

Author(s):

Mei-Mei Cheng ◽

Xu-Li Tang ◽

Yan-Ting Sun ◽

Dong-Yang Song ◽

Yu-Jing Cheng ◽

...

Keyword(s):

Natural Products ◽

Secondary Metabolites ◽

Natural Product ◽

Marine Sponge ◽

Marine Sponges ◽

Chemical Diversity ◽

Comprehensive Overview ◽

Bioactive Secondary Metabolites ◽

The Relationship ◽

Product Chemistry

Marine sponges are well known as rich sources of biologically natural products. Growing evidence indicates that sponges harbor a wealth of microorganisms in their bodies, which are likely to be the true producers of bioactive secondary metabolites. In order to promote the study of natural product chemistry and explore the relationship between microorganisms and their sponge hosts, in this review, we give a comprehensive overview of the structures, sources, and activities of the 774 new marine natural products from sponge-derived microorganisms described over the last two decades from 1998 to 2017.

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Feature-Based Molecular Networking to Target the Isolation of New Caffeic Acid Esters from Yacon (Smallanthus sonchifolius, Asteraceae)

Metabolites ◽

10.3390/metabo10100407 ◽

2020 ◽

Vol 10 (10) ◽

pp. 407

Author(s):

Guillermo F. Padilla-González ◽

Nicholas J. Sadgrove ◽

Gari V. Ccana-Ccapatinta ◽

Olga Leuner ◽

Eloy Fernandez-Cusimamani

Keyword(s):

Mass Spectrometry ◽

Caffeic Acid ◽

High Resolution Mass Spectrometry ◽

Chemical Diversity ◽

Bioactive Metabolites ◽

Molecular Networking ◽

Smallanthus Sonchifolius ◽

Feature Based ◽

Caffeic Acid Esters ◽

Acid Esters

Smallanthus sonchifolius (yacon) is an edible tuberous Andean shrub that has been included in the diet of indigenous people since before recorded history. The nutraceutical and medicinal properties of yacon are widely recognized, especially for the improvement of hyperglycemic disorders. However, the chemical diversity of the main bioactive series of caffeic acid esters has not been explored in detail. In this metabolomics study, we applied the latest tools to facilitate the targeted isolation of new caffeic acid esters. Using liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS), we analyzed extracts from different organs (roots, vascular tissues of the stems, stem epidermis, leaves, bracts, and ray flowers) and followed a feature-based molecular networking approach to characterize the structural diversity of caffeic acid esters and recognize new compounds. The analysis identified three potentially new metabolites, one of them confirmed by isolation and full spectroscopic/spectrometric assignment using nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), and MS/MS. This metabolite (5-O-caffeoyl-2,7-anhydro-d-glycero-β-d-galacto-oct-2-ulopyranosonic acid), along with eight known caffeic acid esters, was isolated from the roots and stems. Furthermore, based on detailed tandem MS analyses, we suggest that the two isomeric monocaffeoyl-2,7-anhydro-2-octulopyranosonic acids found in yacon can be reliably distinguished based on their characteristic MS2 and MS3 spectra. The outcome of the current study confirms the utility of feature-based molecular networking as a tool for targeted isolation of previously undescribed metabolites and reveals the full diversity of potentially bioactive metabolites from S. sonchifolius.

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