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Marine Drugs
Special Issues
Bioactive Compounds from Marine Sponges 2020
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Bioactive Compounds from Marine Sponges 2020

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

Deadline for manuscript submissions: closed (18 December 2020) | Viewed by 23536

Special Issue Editors

Dr. RuAngelie Edrada-Ebel

E-Mail Website
Guest Editor
Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow, UK
Interests: marine natural products chemistry; secondary metabolomics; NMR- and MS-based metabolomics; marine biotechnology
Special Issues, Collections and Topics in MDPI journals
Dr. Roberta Teta

E-Mail Website
Guest Editor
The Blue Chemistry Lab, Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy
Interests: bioactive natural products; marine organisms; microorganisms; structure elucidation; biosynthesis; spectroscopic analysis; metabolomics; molecular networking
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In recent decades, the holobiome of porifera has been revealed as an outstanding source of bioactive compounds that can lead to new drug candidates and/or inspire the development of new scaffolds. The term holobiome is used here to highlight the fact that natural products from porifera often result from the biosynthetic machinery of their symbiotic system. The extraordinary chemical diversity of metabolites produced by sponges and their symbionts translates in an enormous variety of biological activities.

This Special Issue "Bioactive Compounds from Marine Sponges 2019" welcomes contributions focused on the discovery of new sponge-derived bioactive natural products, the elucidation of their structures and synthetic/biosynthetic routes as well as their potential pharmacological applications.

We aim to highlight progress and advance understanding in this field and to gain deeper comprehension of the symbiotic relationships between sponges and symbiotic microorganisms.

As Guest Editors, we invite you to submit relevant contributions to this Special Issue of Marine Drugs.

Prof. RuAngelie Edrada-Ebel
Dr. Roberta Teta
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • bioactive natural products
  • marine sponge symbionts
  • synthesis and biosynthesis
  • structure elucidation

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Published Papers (6 papers)

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Research

23 pages, 11035 KiB  
Article
Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species
by Jarmo-Charles J. Kalinski, Rui W. M. Krause, Shirley Parker-Nance, Samantha C. Waterworth and Rosemary A. Dorrington
Mar. Drugs 2021, 19(2), 68; https://doi.org/10.3390/md19020068 - 28 Jan 2021
Cited by 6 | Viewed by 2800
Abstract
Sponges of the Latrunculiidae family produce bioactive pyrroloiminoquinone alkaloids including makaluvamines, discorhabdins, and tsitsikammamines. The aim of this study was to use LC-ESI-MS/MS-driven molecular networking to characterize the pyrroloiminoquinone secondary metabolites produced by six latrunculid species. These are Tsitsikamma favus, Tsitsikamma pedunculata [...] Read more.
Sponges of the Latrunculiidae family produce bioactive pyrroloiminoquinone alkaloids including makaluvamines, discorhabdins, and tsitsikammamines. The aim of this study was to use LC-ESI-MS/MS-driven molecular networking to characterize the pyrroloiminoquinone secondary metabolites produced by six latrunculid species. These are Tsitsikamma favus, Tsitsikamma pedunculata, Cyclacanthia bellae, and Latrunculia apicalis as well as the recently discovered species, Tsitsikamma nguni and Tsitsikamma michaeli. Organic extracts of 43 sponges were analyzed, revealing distinct species-specific chemical profiles. More than 200 known and unknown putative pyrroloiminoquinones and related compounds were detected, including unprecedented makaluvamine-discorhabdin adducts and hydroxylated discorhabdin I derivatives. The chemical profiles of the new species T. nguni closely resembled those of the known T. favus (chemotype I), but with a higher abundance of tsitsikammamines vs. discorhabdins. T. michaeli sponges displayed two distinct chemical profiles, either producing mostly the same discorhabdins as T. favus (chemotype I) or non- or monobrominated, hydroxylated discorhabdins. C. bellae and L. apicalis produced similar pyrroloiminoquinone chemistry to one another, characterized by sulfur-containing discorhabdins and related adducts and oligomers. This study highlights the variability of pyrroloiminoquinone production by latrunculid species, identifies novel isolation targets, and offers fundamental insights into the collision-induced dissociation of pyrroloiminoquinones. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges 2020)
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13 pages, 2127 KiB  
Article
An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge Spongia sp. from the Red Sea
by Chi-Jen Tai, Chiung-Yao Huang, Atallah F. Ahmed, Raha S. Orfali, Walied M. Alarif, Yusheng M. Huang, Yi-Hsuan Wang, Tsong-Long Hwang and Jyh-Horng Sheu
Mar. Drugs 2021, 19(1), 38; https://doi.org/10.3390/md19010038 - 16 Jan 2021
Cited by 10 | Viewed by 3547
Abstract
Chemical investigation of a Red Sea Spongia sp. led to the isolation of four new compounds, i.e., 17-dehydroxysponalactone (1), a carboxylic acid, spongiafuranic acid A (2), one hydroxamic acid, spongiafuranohydroxamic acid A (3), and a furanyl trinorsesterpenoid [...] Read more.
Chemical investigation of a Red Sea Spongia sp. led to the isolation of four new compounds, i.e., 17-dehydroxysponalactone (1), a carboxylic acid, spongiafuranic acid A (2), one hydroxamic acid, spongiafuranohydroxamic acid A (3), and a furanyl trinorsesterpenoid 16-epi-irciformonin G (4), along with three known metabolites (−)-sponalisolide B (5), 18-nor- 3,17-dihydroxy-spongia-3,13(16),14-trien-2-one (6), and cholesta-7-ene-3β,5α-diol-6-one (7). The biosynthetic pathway for the molecular skeleton of 1 and related compounds was postulated for the first time. Anti-inflammatory activity of these metabolites to inhibit superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophil cells and cytotoxicity of these compounds toward three cancer cell lines and one human dermal fibroblast cell line were assayed. Compound 1 was found to significantly reduce the superoxide anion generation and elastase release at a concentration of 10 μM, and compound 5 was also found to display strong inhibitory activity against superoxide anion generation at the same concentration. Due to the noncytotoxic activity and the potent inhibitory effect toward the superoxide anion generation and elastase release, 1 and 5 can be considered to be promising anti-inflammatory agents. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges 2020)
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14 pages, 1093 KiB  
Article
Bioactive Bis(indole) Alkaloids from a Spongosorites sp. Sponge
by Jae Sung Park, Eunji Cho, Ji-Yeon Hwang, Sung Chul Park, Beomkoo Chung, Oh-Seok Kwon, Chung J. Sim, Dong-Chan Oh, Ki-Bong Oh and Jongheon Shin
Mar. Drugs 2021, 19(1), 3; https://doi.org/10.3390/md19010003 - 23 Dec 2020
Cited by 15 | Viewed by 3938
Abstract
Six new bis(indole) alkaloids (1–6) along with eight known ones of the topsentin class were isolated from a Spongosorites sp. sponge of Korea. Based on the results of combined spectroscopic analyses, the structures of spongosoritins A–D (1– [...] Read more.
Six new bis(indole) alkaloids (1–6) along with eight known ones of the topsentin class were isolated from a Spongosorites sp. sponge of Korea. Based on the results of combined spectroscopic analyses, the structures of spongosoritins A–D (1–4) were determined to possess a 2-methoxy-1-imidazole-5-one core connecting the indole moieties, and these were linked by a linear urea bridge for spongocarbamides A (5) and B (6). The absolute configurations of spongosoritins were assigned by electronic circular dichroism (ECD) computation. The new compounds exhibited moderate inhibition against transpeptidase sortase A and weak inhibition against human pathogenic bacteria and A549 and K562 cancer cell lines. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges 2020)
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16 pages, 2487 KiB  
Article
Therapeutic Potential of (−)-Agelamide D, a Diterpene Alkaloid from the Marine Sponge Agelas sp., as a Natural Radiosensitizer in Hepatocellular Carcinoma Models
by Changhoon Choi, Yeonwoo Cho, Arang Son, Sung-Won Shin, Yeon-Ju Lee and Hee Chul Park
Mar. Drugs 2020, 18(10), 500; https://doi.org/10.3390/md18100500 - 29 Sep 2020
Cited by 8 | Viewed by 3123
Abstract
Radiation therapy (RT) is an effective local treatment for unresectable hepatocellular carcinoma (HCC), but there are currently no predictive biomarkers to guide treatment decision for RT or adjuvant systemic drugs to be combined with RT for HCC patients. Previously, we reported that extracts [...] Read more.
Radiation therapy (RT) is an effective local treatment for unresectable hepatocellular carcinoma (HCC), but there are currently no predictive biomarkers to guide treatment decision for RT or adjuvant systemic drugs to be combined with RT for HCC patients. Previously, we reported that extracts of the marine sponge Agelas sp. may contain a natural radiosensitizer for HCC treatment. In this study, we isolated (−)-agelamide D from Agelas extract and investigated the mechanism underlying its radiosensitization. (−)-Agelamide D enhanced radiation sensitivity of Hep3B cells with decreased clonogenic survival and increased apoptotic cell death. Furthermore, (−)-agelamide D increased the expression of protein kinase RNA-like endoplasmic reticulum kinase/inositol-requiring enzyme 1α/activating transcription factor 4 (PERK/eIF2α/ATF4), a key pathway of the unfolded protein response (UPR) in multiple HCC cell lines, and augmented radiation-induced UPR signaling. In vivo xenograft experiments confirmed that (−)-agelamide D enhanced tumor growth inhibition by radiation without systemic toxicity. Immunohistochemistry results showed that (−)-agelamide D further increased radiation-induced ATF4 expression and apoptotic cell death, which was consistent with our in vitro finding. Collectively, our results provide preclinical evidence that the use of UPR inducers such as (−)-agelamide D may enhance the efficacy of RT in HCC management. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges 2020)
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11 pages, 1124 KiB  
Article
New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from Stylissa caribica
by Silvia Scarpato, Roberta Teta, Gerardo Della Sala, Joseph R. Pawlik, Valeria Costantino and Alfonso Mangoni
Mar. Drugs 2020, 18(9), 443; https://doi.org/10.3390/md18090443 - 27 Aug 2020
Cited by 16 | Viewed by 3852
Abstract
Feature-based molecular networking was used to re-examine the secondary metabolites in extracts of a very well studied marine sponge, Stylissa caribica, known to contain a large array of cyclic peptides and brominated alkaloids. The analysis revealed the presence of 13 cyclic peptides [...] Read more.
Feature-based molecular networking was used to re-examine the secondary metabolites in extracts of a very well studied marine sponge, Stylissa caribica, known to contain a large array of cyclic peptides and brominated alkaloids. The analysis revealed the presence of 13 cyclic peptides in the sponge that had never been detected in previous work and appeared to be new compounds. The most abundant one was isolated and shown to be a new proline-rich cyclic heptapetide that was called stylissamide L (1). Structure of compound 1, including the cis/trans geometry of the three proline residues, was determined by extensive NMR studies; the l configuration of the seven amino acid residues was determined using Marfey’s method. Stylissamide L was tested for activity as a cell growth inhibitor and cell migration inhibitor on two cancer cell lines but, unlike other members of the stylissamide family, it showed no significant activity. This approach showed that even a thoroughly studied species such as S. caribica may contain new chemistry that can be revealed if studied with the right tools. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges 2020)
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15 pages, 2442 KiB  
Article
Renieramycin T Induces Lung Cancer Cell Apoptosis by Targeting Mcl-1 Degradation: A New Insight in the Mechanism of Action
by Korrakod Petsri, Supakarn Chamni, Khanit Suwanborirux, Naoki Saito and Pithi Chanvorachote
Mar. Drugs 2019, 17(5), 301; https://doi.org/10.3390/md17050301 - 21 May 2019
Cited by 21 | Viewed by 5013
Abstract
Among malignancies, lung cancer is the major cause of cancer death. Despite the advance in lung cancer therapy, the five-year survival rate is extremely restricted due to therapeutic failure and disease relapse. Targeted therapies selectively inhibiting certain molecules in cancer cells have been [...] Read more.
Among malignancies, lung cancer is the major cause of cancer death. Despite the advance in lung cancer therapy, the five-year survival rate is extremely restricted due to therapeutic failure and disease relapse. Targeted therapies selectively inhibiting certain molecules in cancer cells have been accepted as promising ways to control cancer. In lung cancer, evidence has suggested that the myeloid cell leukemia 1 (Mcl-1) protein, an anti-apoptotic member of the Bcl-2 family, is a target for drug action. Herein, we report the Mcl-1 targeting activity of renieramycin T (RT), a marine-derived tetrahydroisoquinoline alkaloid that was isolated from the Thai blue sponge Xestospongia sp. RT was shown to be dominantly toxic to lung cancer cells compared to the normal cells in the lung. The cytotoxicity of this compound toward lung cancer cells was mainly exerted through apoptosis induction. For the mechanism of action, we found that RT mediated activation of p53 protein and caspase-9 and -3 activations. While others Bcl-2 family proteins (Bcl-2, Bak, and Bax) were minimally changed in response to RT, Mcl-1 protein was dramatically diminished. We further performed the cycloheximide experiment and found that the half-life of Mcl-1 was significantly shortened by RT treatment. When MG132, a potent selective proteasome inhibitor, was utilized, it could restore the Mcl-1 level. Furthermore, immunoprecipitation analysis revealed that RT significantly increased the formation of Mcl-1-ubiquitin complex compared to the non-treated control. In conclusion, we report the potential apoptosis induction of RT with a mechanism of action involving the targeting of Mcl-1 for ubiquitin-proteasomal degradation. As Mcl-1 is critical for cancer cell survival and chemotherapeutic failure, this novel information regarding the Mcl-1-targeted compound would be beneficial for the development of efficient anti-cancer strategies or targeted therapies. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges 2020)
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