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30 pages, 10822 KiB

Open AccessEditor’s ChoiceArticle

Cytotoxic Alkylynols of the Sponge Cribrochalina vasculum: Structure, Synthetic Analogs and SAR Studies

by Dimitry Kovalerchik, Ana Zovko, Petra Hååg, Adam Sierakowiak, Kristina Viktorsson, Rolf Lewensohn, Micha Ilan and Shmuel Carmeli

Mar. Drugs 2022, 20(4), 265; https://doi.org/10.3390/md20040265 - 13 Apr 2022

Cited by 2 | Viewed by 2634

Abstract

A series of twenty-three linear and branched chain mono acetylene lipids were isolated from the Caribbean Sea sponge Cribrochalina vasculum. Seventeen of the compounds, 1–17, are new, while six, 18–23, were previously characterized from the same sponge. Some of the [...] Read more.

A series of twenty-three linear and branched chain mono acetylene lipids were isolated from the Caribbean Sea sponge Cribrochalina vasculum. Seventeen of the compounds, 1–17, are new, while six, 18–23, were previously characterized from the same sponge. Some of the new acetylene-3-hydroxy alkanes 1, 6, 7, 8, 10 were tested for selective cytotoxicity in non-small cell lung carcinoma (NSCLC) cells over WI-38 normal diploid lung fibroblasts. Compound 7, presented clear tumor selective activity while, 1 and 8, showed selectivity at lower doses and 6 and 10, were not active towards NSCLC cells at all. The earlier reported selective cytotoxicity of some acetylene-3-hydroxy alkanes (scal-18 and 23), in NSCLC cells and/or other tumor cell types were also confirmed for 19, 20 and 22. To further study the structure activity relationships (SAR) of this group of compounds, we synthesized several derivatives of acetylene-3-hydroxy alkanes, rac-18, scal-S-18, R-18, rac-27, rac-32, R-32, S-32, rac-33, rac-41, rac-42, rac-43, rac-45, rac-48 and rac-49, along with other 3-substituted derivatives, rac-35, rac-36, rac-37, rac-38, rac-39 and rac-40, and assessed their cytotoxic activity against NSCLC cells and diploid fibroblasts. SAR studies revealed that the alcohol moiety at position 3 and its absolute R configuration both were essential for the tumor cell line selective activity while for its cytotoxic magnitude the alkyl chain length and branching were of less significance. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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20 pages, 1675 KiB

Open AccessArticle

Good Practices in Sponge Natural Product Studies: Revising Vouchers with Isomalabaricane Triterpenes

by Paco Cárdenas, Jayani Gamage, Chamari M. Hettiarachchi and Sunithi Gunasekera

Mar. Drugs 2022, 20(3), 190; https://doi.org/10.3390/md20030190 - 4 Mar 2022

Cited by 7 | Viewed by 4331

Abstract

Species misidentification in the field of natural products is an acknowledged problem. These errors are especially widespread in sponge studies, albeit rarely assessed and documented. As a case study, we aim to revisit reports of isomalabaricane triterpenes, isolated from four demosponge genera: Jaspis [...] Read more.

Species misidentification in the field of natural products is an acknowledged problem. These errors are especially widespread in sponge studies, albeit rarely assessed and documented. As a case study, we aim to revisit reports of isomalabaricane triterpenes, isolated from four demosponge genera: Jaspis, Geodia, Stelletta and Rhabdastrella. From a total of 44 articles (1981–2022), 27 unique vouchers were listed, 21 of which were accessed and re-examined here: 11 (52.4%) of these were misidentified. Overall, 65.9% of the studies published an incorrect species name: previously identified Jaspis and Stelletta species were all in fact Rhabdastrella globostellata. We conclude that isomalabaricane triterpenes were isolated from only two Rhabdastrella species and possibly one Geodia species. In addition to shedding a new light on the distribution of isomalabaricane triterpenes, this study is an opportunity to highlight the crucial importance of vouchers in natural product studies. Doing so, we discuss the impact of species misidentification and poor accessibility of vouchers in the field of sponge natural products. We advocate for stricter voucher guidelines in natural product journals and propose a common protocol of good practice, in the hope of reducing misidentifications in sponge studies, ensure reproducibility of studies, and facilitate follow-up work on the original material. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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20 pages, 5174 KiB

Open AccessArticle

Actinoporin-like Proteins Are Widely Distributed in the Phylum Porifera

by Kenneth Sandoval and Grace P. McCormack

Mar. Drugs 2022, 20(1), 74; https://doi.org/10.3390/md20010074 - 15 Jan 2022

Cited by 3 | Viewed by 3721

Abstract

Actinoporins are proteinaceous toxins known for their ability to bind to and create pores in cellular membranes. This quality has generated interest in their potential use as new tools, such as therapeutic immunotoxins. Isolated historically from sea anemones, genes encoding for similar actinoporin-like [...] Read more.

Actinoporins are proteinaceous toxins known for their ability to bind to and create pores in cellular membranes. This quality has generated interest in their potential use as new tools, such as therapeutic immunotoxins. Isolated historically from sea anemones, genes encoding for similar actinoporin-like proteins have since been found in a small number of other animal phyla. Sequencing and de novo assembly of Irish Haliclona transcriptomes indicated that sponges also possess similar genes. An exhaustive analysis of publicly available sequencing data from other sponges showed that this is a potentially widespread feature of the Porifera. While many sponge proteins possess a sequence similarity of 27.70–59.06% to actinoporins, they show consistency in predicted structure. One gene copy from H. indistincta has significant sequence similarity to sea anemone actinoporins and possesses conserved residues associated with the fundamental roles of sphingomyelin recognition, membrane attachment, oligomerization, and pore formation, indicating that it may be an actinoporin. Phylogenetic analyses indicate frequent gene duplication, no distinct clade for sponge-derived proteins, and a stronger signal towards actinoporins than similar proteins from other phyla. Overall, this study provides evidence that a diverse array of Porifera represents a novel source of actinoporin-like proteins which may have biotechnological and pharmaceutical applications. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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21 pages, 1844 KiB

Open AccessArticle

A Multi-Species Investigation of Sponges’ Filtering Activity towards Marine Microalgae

by Despoina Varamogianni-Mamatsi, Thekla I. Anastasiou, Emmanouela Vernadou, Nikos Papandroulakis, Nicolas Kalogerakis, Thanos Dailianis and Manolis Mandalakis

Mar. Drugs 2022, 20(1), 24; https://doi.org/10.3390/md20010024 - 24 Dec 2021

Cited by 8 | Viewed by 4244

Abstract

Chronic discharge of surplus organic matter is a typical side effect of fish aquaculture, occasionally leading to coastal eutrophication and excessive phytoplankton growth. Owing to their innate filter-feeding capacity, marine sponges could mitigate environmental impact under integrated multitrophic aquaculture (IMTA) scenarios. Herein, we [...] Read more.

Chronic discharge of surplus organic matter is a typical side effect of fish aquaculture, occasionally leading to coastal eutrophication and excessive phytoplankton growth. Owing to their innate filter-feeding capacity, marine sponges could mitigate environmental impact under integrated multitrophic aquaculture (IMTA) scenarios. Herein, we investigated the clearance capacity of four ubiquitous Mediterranean sponges (Agelas oroides, Axinella cannabina, Chondrosia reniformis and Sarcotragus foetidus) against three microalgal substrates with different size/motility characteristics: the nanophytoplankton Nannochloropsis sp. (~3.2 μm, nonmotile) and Isochrysis sp. (~3.8 μm, motile), as well as the diatom Phaeodactylum tricornutum (~21.7 μm, nonmotile). In vitro cleaning experiments were conducted using sponge explants in 1 L of natural seawater and applying different microalgal cell concentrations under light/dark conditions. The investigated sponges exhibited a wide range of retention efficiencies for the different phytoplankton cells, with the lowest average values found for A. cannabina (37%) and the highest for A. oroides (70%). The latter could filter up to 14.1 mL seawater per hour and gram of sponge wet weight, by retaining 100% of Isochrysis at a density of 10⁵ cells mL⁻¹, under darkness. Our results highlight differences in filtering capacity among sponge species and preferences for microalgal substrates with distinct size and motility traits. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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14 pages, 2941 KiB

Open AccessArticle

On the Path to Thermo-Stable Collagen: Culturing the Versatile Sponge Chondrosia reniformis

by Boaz Orel, Marco Giovine and Micha Ilan

Mar. Drugs 2021, 19(12), 669; https://doi.org/10.3390/md19120669 - 26 Nov 2021

Cited by 5 | Viewed by 2596

Abstract

The collagen proteins family is sought-after in the pharmaceuticals, cosmetics, and food industries for various biotechnological applications. The most abundant sources of collagen are pigs and cows, but due to religious restrictions and possible disease transmission, they became less attractive. An alternative source [...] Read more.

The collagen proteins family is sought-after in the pharmaceuticals, cosmetics, and food industries for various biotechnological applications. The most abundant sources of collagen are pigs and cows, but due to religious restrictions and possible disease transmission, they became less attractive. An alternative source can be found in marine invertebrates, specifically in sponges. Alas, two problems arise: (1). Growing sponges is complicated. (2). Sponge collagen has low heat tolerance, which can impose a problem for human biotechnological usage. To fill these gaps, we studied the collagen-abundant sponge Chondrosia reniformis. Two culture experiments were conducted: (1). A sea-based system examined the difference in growth rates of C. reniformis from different habitats, growing under natural seasonal conditions; (2). A land-based controlled system, which assessed the growth-rate of C. reniformis at different temperatures. The results reveal that C. reniformis from shallow habitats are growing larger and faster than individuals from colder, deeper habitats, and that the optimal temperature for C. reniformis growth is 25 °C. The results demonstrate that C. reniformis is highly fit for culture and can produce thermally stable collagen. Further research is needed to determine the best conditions for C. reniformis culture for collagen extract and other exciting materials for bioprospecting. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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15 pages, 2666 KiB

Open AccessArticle

3-D Culture of Marine Sponge Cells for Production of Bioactive Compounds

by Elizabeth Urban-Gedamke, Megan Conkling, Peter J. McCarthy, Paul S. Wills and Shirley A. Pomponi

Mar. Drugs 2021, 19(10), 569; https://doi.org/10.3390/md19100569 - 14 Oct 2021

Cited by 6 | Viewed by 4615

Abstract

Production of sponge-derived bioactive compounds in vitro has been proposed as an alternative to wild harvest, aquaculture, and chemical synthesis to meet the demands of clinical drug development and manufacture. Until recently, this was not possible because there were no marine invertebrate cell [...] Read more.

Production of sponge-derived bioactive compounds in vitro has been proposed as an alternative to wild harvest, aquaculture, and chemical synthesis to meet the demands of clinical drug development and manufacture. Until recently, this was not possible because there were no marine invertebrate cell lines. Recent breakthroughs in the development of sponge cell lines and rapid cell division in improved nutrient media now make this approach a viable option. We hypothesized that three-dimensional (3-D) cell cultures would better represent how sponges function in nature, including the production of bioactive compounds. We successfully cultured sponge cells in 3-D matrices using FibraCel^® disks, thin hydrogel layers, and gel microdroplets (GMDs). For in vitro production of bioactive compounds, the use of GMDs is recommended. Nutrients and sponge products rapidly diffuse into and out of the 3-D matrix, the GMDs may be scaled up in spinner flasks, and cells and/or secreted products can be easily recovered. Research on scale-up and production is in progress in our laboratory. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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14 pages, 1247 KiB

Open AccessArticle

Cyclopeptide Derivatives from the Sponge-Derived Fungus Acremonium persicinum F10

by Yingxin Li and Zhiyong Li

Mar. Drugs 2021, 19(10), 537; https://doi.org/10.3390/md19100537 - 24 Sep 2021

Cited by 7 | Viewed by 2509

Abstract

Cyclopeptides usually play a pivotal role, either in the viability or virulence of fungi. Two types of cyclopeptides, six new hydroxamate siderophore cyclohexapeptides (1–6), including acremonpeptides E and F, and their complexes with aluminum and ferric ions; one new [...] Read more.

Cyclopeptides usually play a pivotal role, either in the viability or virulence of fungi. Two types of cyclopeptides, six new hydroxamate siderophore cyclohexapeptides (1–6), including acremonpeptides E and F, and their complexes with aluminum and ferric ions; one new cyclic pentapeptolide, aselacin D (9); together with a known compound, aselacin C (10), were isolated and characterized from the sponge-derived fungus Acremonium persicinum F10. In addition, two new siderophore analogues chelating gallium ions (Ga³⁺), Ga (III)-acremonpeptide E (7) and Ga (III)-acremonpeptide F (8), using isolated acremonpeptides E and F, were prepared. The planar structures of 1–10 were elucidated by HRESIMS and (1D and 2D) NMR. The absolute configurations of amino acids were determined by means of the advanced Marfey’s method and X-ray single-crystal diffraction analysis. X-ray fluorescence (XRF) spectrometer was performed to disclose the elements of compound 1, indicating the existence of aluminum (Al). Al (III)-acremonpeptides E (1), Ga (III)-acremonpeptides E (5), Al (III)-acremonpeptide F (7), and Ga (III)-acremonpeptide F (8) displayed high in vitro anti-fungal activities, which are comparable to amphotericin B, against Aspergillus fumigatus and Aspergillus niger. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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Review

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25 pages, 14025 KiB

Open AccessFeature PaperEditor’s ChoiceReview

A Soft Spot for Chemistry–Current Taxonomic and Evolutionary Implications of Sponge Secondary Metabolite Distribution

by Adrian Galitz, Yoichi Nakao, Peter J. Schupp, Gert Wörheide and Dirk Erpenbeck

Mar. Drugs 2021, 19(8), 448; https://doi.org/10.3390/md19080448 - 4 Aug 2021

Cited by 20 | Viewed by 5025

Abstract

Marine sponges are the most prolific marine sources for discovery of novel bioactive compounds. Sponge secondary metabolites are sought-after for their potential in pharmaceutical applications, and in the past, they were also used as taxonomic markers alongside the difficult and homoplasy-prone sponge morphology [...] Read more.

Marine sponges are the most prolific marine sources for discovery of novel bioactive compounds. Sponge secondary metabolites are sought-after for their potential in pharmaceutical applications, and in the past, they were also used as taxonomic markers alongside the difficult and homoplasy-prone sponge morphology for species delineation (chemotaxonomy). The understanding of phylogenetic distribution and distinctiveness of metabolites to sponge lineages is pivotal to reveal pathways and evolution of compound production in sponges. This benefits the discovery rate and yield of bioprospecting for novel marine natural products by identifying lineages with high potential of being new sources of valuable sponge compounds. In this review, we summarize the current biochemical data on sponges and compare the metabolite distribution against a sponge phylogeny. We assess compound specificity to lineages, potential convergences, and suitability as diagnostic phylogenetic markers. Our study finds compound distribution corroborating current (molecular) phylogenetic hypotheses, which include yet unaccepted polyphyly of several demosponge orders and families. Likewise, several compounds and compound groups display a high degree of lineage specificity, which suggests homologous biosynthetic pathways among their taxa, which identifies yet unstudied species of this lineage as promising bioprospecting targets. Full article

(This article belongs to the Special Issue Marine Sponge Biotechnology)

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