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

Deadline for manuscript submissions: closed (31 December 2017) | Viewed by 70304

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Prof. Dr. Jyh-Horng Sheu

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Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804201, Taiwan
Interests: synthesis of bioactive natural products; structure modification of natural products; chemistry of marine natural products
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Special Issue Information

Dear Colleagues,

Coral reefs are the major habitat of numerous marine organisms. Ecologically, they are referred to as the rainforests of ocean, and are home to many species of algae, cyanobacteria, and marine animals, such as fish, crustaceans, corals, sponges, bryozoans, tunicates, mollusks, and echinoderms. Many reef organisms, and the associated microorganisms, can, not only produce nutritional substances, but also bioactive metabolites to defend themselves against predators, fight diseases, and prevent the fouling and overgrowth of other organisms. These natural products may also be useful for the discovery of new drugs. Dozens of promising compounds, originating from coral reef organisms, have been approved or are under clinical trials for use as painkillers, anticancer purposes, and antiviral drugs, or for the treatment of other diseases. Thus, coral reef organisms are well recognized as a rich source of bioactive natural products, which might become useful medicines in future drug development.

The goal of this Special Issue is to provide a platform for scientists of related fields to share and report the discovery and development of natural products from coral reef organisms. We invite researchers from all over the world to publish original research and review articles in this Special Issue. Potential topics include, but are not limited to:

Natural products from marine algae and microalgae
Natural products from marine invertebrates
Natural products from marine microorganisms
Marine natural products as antifouling agents
Marine natural products for fighting diseases

Prof. Dr. Jyh-Horng Sheu
Guest Editor

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

Coral reef organism
Natural product
Structure elucidation
Drug development

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Related Special Issue

Bioactive Natural Products from Soft Corals in Marine Drugs (2 articles)

Published Papers (14 papers)

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Research

10 pages, 2001 KiB

Open AccessArticle

Further New Diterpenoids as PTP1B Inhibitors from the Xisha Soft Coral Sinularia polydactyla

by Fei Ye, Zheng-Dan Zhu, Yu-Cheng Gu, Jia Li, Wei-Liang Zhu and Yue-Wei Guo

Mar. Drugs 2018, 16(4), 103; https://doi.org/10.3390/md16040103 - 25 Mar 2018

Cited by 25 | Viewed by 4283

Abstract

A new prenyleudesmane type diterpene, sinupol (8), and a new capnosane type diterpenoid, sinulacetate (9), were isolated from the Xisha soft coral Sinularia polydactyla along with five known related diterpenes (4–7 and 10). Their structures, including absolute configurations, were determined by extensive spectroscopic analysis, the comparison of their NMR data with those of related compounds, and time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations. Both new compounds (8 and 9) exhibited promising inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a potential drug target for the treatment of type II diabetes and obesity. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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10 pages, 2045 KiB

Open AccessArticle

Anti-Inflammatory Polyoxygenated Steroids from the Soft Coral Lobophytum michaelae

by Chiung-Yao Huang, Wan-Ru Tseng, Atallah F. Ahmed, Pei-Lun Chiang, Chi-Jen Tai, Tsong-Long Hwang, Chang-Feng Dai and Jyh-Horng Sheu

Mar. Drugs 2018, 16(3), 93; https://doi.org/10.3390/md16030093 - 13 Mar 2018

Cited by 25 | Viewed by 5260

Abstract

Three new polyoxygenated steroids, michosterols A–C (1–3), and four known compounds (4–7) were isolated from the ethyl acetate (EtOAc) extract of the soft coral Lobophytum michaelae, collected off the coast of Taitung. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and comparison of the nuclear magnetic resonance (NMR) data with related steroids. The cytotoxicity of compounds 1–3 against the proliferation of a limited panel of cancer cell lines was assayed. Compound 1 was found to display moderate cytotoxicity against adenocarcinomic human alveolar basal epithelial (A549) cancer cells. It also exhibited potent anti-inflammatory activity by suppressing superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-stimulated human neutrophils. Furthermore, 3 could effectively inhibit elastase release, as well. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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13 pages, 3491 KiB

Open AccessArticle

Briaviolides K–N, New Briarane-Type Diterpenoids from Cultured Octocoral Briareum violaceum

by Jing-Hao Xu, Kuei-Hung Lai, Yin-Di Su, Yu-Chia Chang, Bo-Rong Peng, Anders Backlund, Zhi-Hong Wen and Ping-Jyun Sung

Mar. Drugs 2018, 16(3), 75; https://doi.org/10.3390/md16030075 - 27 Feb 2018

Cited by 17 | Viewed by 4498

Abstract

Four new briarane diterpenoids, briaviolides K–N (1–4), have been obtained from the cultured-type octocoral Briareum violaceum. Using a spectroscopic approach, the structures of briaranes 1–4 were identified. This study employed an in vitro model of lipopolysaccharide (LPS)-induced inflammation in the murine macrophage RAW 264.7 cell line, and found that among the four briaranes, briarane 2 possessed anti-inflammatory activity against inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expressions in cells. In addition, principal component analysis using the chemical global positioning system (ChemGPS) for natural products (ChemGPS-NP) was employed in order to analyze the structure-activity relationship (SAR), and the results indicated that the ring conformation of the compound has a leading role in suppressing the expressions of pro-inflammatory iNOS and COX-2 proteins in macrophages. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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9 pages, 2088 KiB

Open AccessArticle

Tetrocarcin Q, a New Spirotetronate with a Unique Glycosyl Group from a Marine-Derived Actinomycete Micromonospora carbonacea LS276

by Ting Gong, Xin Zhen, Xing-Lun Li, Jing-Jing Chen, Tian-Jiao Chen, Jin-Ling Yang and Ping Zhu

Mar. Drugs 2018, 16(2), 74; https://doi.org/10.3390/md16020074 - 24 Feb 2018

Cited by 23 | Viewed by 5244

Abstract

A new spirotetronate glycoside tetrocarcin Q (1) and six known analogues tetrocarcin A (2), AC6H (3), tetrocarcin N (4), tetrocarcin H (5), arisostatin A (6), and tetrocarcin F1 (7) [...] Read more.

A new spirotetronate glycoside tetrocarcin Q (1) and six known analogues tetrocarcin A (2), AC6H (3), tetrocarcin N (4), tetrocarcin H (5), arisostatin A (6), and tetrocarcin F1 (7) were isolated from the fermentation broth of the marine-derived actinomycete Micromonospora carbonacea LS276. Their chemical structures were established on the basis of 1D- and 2D-NMR spectroscopy, as well as HR-ESI-MS analysis. The absolute configurations of their stereogenic carbons were determined by circular dichroism (CD) analysis. Compound 1 possesses 2-deoxy-allose, which is a unique sugar type at the C-9 position. This type has not been found in the previously reported spirotetronate glycosides. Compound 1 displayed moderate antibacterial activity against Bacillus subitlis ATCC 63501 with minimum inhibitory concentration (MIC) value of 12.5 μM. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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10 pages, 1634 KiB

Open AccessArticle

Anti-Lymphangiogenesis Components from Zoanthid Palythoa tuberculosa

by Shu-Rong Chen, Shih-Wei Wang, Chien-Jung Su, Hao-Chun Hu, Yu-Liang Yang, Chi-Ting Hsieh, Chia-Chi Peng, Fang-Rong Chang and Yuan-Bin Cheng

Mar. Drugs 2018, 16(2), 47; https://doi.org/10.3390/md16020047 - 31 Jan 2018

Cited by 11 | Viewed by 4500

Abstract

Three new compounds, tuberazines A–C (1–3), and eleven known compounds (4–14) were obtained from the ethanolic extract of Taiwanese zoanthid Palythoa tuberculosa. Compounds 1–4 are rare marine natural products with a pyrazine moiety, and compound 5 is a tricyclic tryptamine derivative isolated from nature for the first time. The structures of all isolated metabolites were determined by analyzing their IR, Mass, NMR, and UV spectrometric data. The absolute configuration of 1 was confirmed by comparing the trend of experimental electronic circular dichroism (ECD) with calculated ECD spectra. The anti-lymphangiogenic activities of new compounds were evaluated in human lymphatic endothelial cells (LECs). Of these, new compound 3 displayed the most potent anti-lymphangiogenesis property by suppressing cell growth and tube formation of LECs. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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6 pages, 2725 KiB

Open AccessArticle

Xeniaphyllane-Derived Terpenoids from Soft Coral Sinularia nanolobata

by Fu-Yun Hsu, Shang-Kwei Wang and Chang-Yih Duh

Mar. Drugs 2018, 16(2), 40; https://doi.org/10.3390/md16020040 - 24 Jan 2018

Cited by 13 | Viewed by 3747

Abstract

A novel tetranorditerpenoid, sinubatin A (1) (having an unprecedented carbon skeleton), a new norditerpenoid, sinubatin B (2) (a 4,5-epoxycaryophyllene possessing an unusual methylfuran moiety side chain), and a known diterpenoid, gibberosin J (3) were isolated from soft coral Sinularia nanolobata. The structures of the new compounds were elucidated by extensive analysis of spectroscopic data. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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12 pages, 3991 KiB

Open AccessArticle

Aquaculture Soft Coral Lobophytum crassum as a Producer of Anti-Proliferative Cembranoids

by Bo-Rong Peng, Mei-Chin Lu, Mohamed El-Shazly, Shwu-Li Wu, Kuei-Hung Lai and Jui-Hsin Su

Mar. Drugs 2018, 16(1), 15; https://doi.org/10.3390/md16010015 - 7 Jan 2018

Cited by 19 | Viewed by 6447

Abstract

Our continuous search for marine bioactive secondary metabolites led to the screening of crude extracts from a variety of aquaculture soft corals. The ethyl acetate (EtOAc) extract of Lobophytum crassum showed a distinctive chemical profile that was different from the wild type. It demonstrated significant anti-proliferative activity against Molt 4 leukemia cell with an IC₅₀ value of 1 μg/mL after 24 h. Chemical investigation focusing on the unique peaks in L. crassum profile led to the discovery of a new α-tocopherol crassumtocopherol C (1), and two new cembrane-based diterpenoids culobophylins D (2) and E (3), along with ten known cembranoids (4–13). The structures of these isolates were elucidated using extensive spectroscopic techniques and a comparison with previously published data of related metabolites. Compound 2 was found to possess the first identified saturated internal C₄-O-C₁₄ linkage six-membered ring among all cembrane-type diterpenoids. The anti-proliferative activity of all the isolates (except 3) was evaluated against a limited panel of leukemia cell lines (Molt 4, K562, U937, and Sup-T1). The major compounds 8 and 10 exhibited the most anti-proliferative potent effect, with IC₅₀ values ranging from 1.2 to 7.1 μM. The Structure Activity Relationship (SAR) of the isolates suggested that the presence of lactone moieties is crucial for the anti-proliferative activity against leukemia cells. Our work indicated that the development of an efficient aquaculture protocols for soft corals led to the discovery of new secondary metabolites with unique structural features. Such protocols can lead to a sustainable supply of biologically active compounds in enough quantities for the pharmaceutical industry. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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1272 KiB

Open AccessArticle

New Cytotoxic Terpenoids from Soft Corals Nephthea chabroli and Paralemnalia thyrsoides

by Yu-Sheng Lee, Tsai-Hui Duh, Shu-Sheng Siao, Rey-Chang Chang, Shang-Kwei Wang and Chang-Yih Duh

Mar. Drugs 2017, 15(12), 392; https://doi.org/10.3390/md15120392 - 19 Dec 2017

Cited by 19 | Viewed by 5109

Abstract

A novel cytotoxic diterpenoid, chabrolin A (1) (possessing an unprecedented terpenoid skeleton), as well as three new cytotoxic sesquiterpenoids, parathyrsoidins E–G (2–4), were isolated by cytotoxicity-guided fractionation from soft corals Nephthea chabroli and Paralemnalia thyrsoides. The [...] Read more.

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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1864 KiB

Open AccessArticle

Anti-Inflammatory Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium

by Atallah F. Ahmed, Wan-Ting Teng, Chiung-Yao Huang, Chang-Feng Dai, Tsong-Long Hwang and Jyh-Horng Sheu

Mar. Drugs 2017, 15(10), 300; https://doi.org/10.3390/md15100300 - 29 Sep 2017

Cited by 14 | Viewed by 5790

Abstract

New lobane-based diterpenoids lobovarols A–D (1–4) and a prenyleudesmane-type diterpenoid lobovarol E (5) along with seven known related diterpenoids (6–12) were isolated from the ethyl acetate extract of a Taiwanese soft coral Lobophytum varium. Their structures were identified on the basis of multiple spectroscopic analyses and spectral comparison. The absolute configuration at C-16 of the known compound 11 is reported herein for the first time. The anti-inflammatory activities of compounds 1–12 were assessed by measuring their inhibitory effect on N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release in human neutrophils. Metabolites 2, 5, and 11 were found to show moderate inhibitory activity on the generation of superoxide anion, while compounds 5, 8, 11, and 12 could effectively suppress elastase release in fMLP/CB-stimulated human neutrophil cells at 10 μM. All of the isolated diterpenoids did not exhibit cytotoxic activity (IC₅₀ > 50 μM) towards a limited panel of cancer cell lines. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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1648 KiB

Open AccessArticle

Bioactive Steroids with Methyl Ester Group in the Side Chain from a Reef Soft Coral Sinularia brassica Cultured in a Tank

by Chiung-Yao Huang, Jui-Hsin Su, Chih-Chuang Liaw, Ping-Jyun Sung, Pei-Lun Chiang, Tsong-Long Hwang, Chang-Feng Dai and Jyh-Horng Sheu

Mar. Drugs 2017, 15(9), 280; https://doi.org/10.3390/md15090280 - 1 Sep 2017

Cited by 23 | Viewed by 5013

Abstract

A continuing chemical investigation of the ethyl acetate (EtOAc) extract of a reef soft coral Sinularia brassica, which was cultured in a tank, afforded four new steroids with methyl ester groups, sinubrasones A–D (1–4) for the first time. In particular, 1 possesses a β-D-xylopyranose. The structures of the new compounds were elucidated on the basis of spectroscopic analyses. The cytotoxicities of compounds 1–4 against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of these new compounds 1–4 were also evaluated by measuring their ability to suppress superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced human neutrophils. Compounds 2 and 3 were shown to exhibit significant cytotoxicity, and compounds 3 and 4 were also found to display attracting anti-inflammatory activities. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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6121 KiB

Open AccessArticle

Sinulariolide Suppresses Cell Migration and Invasion by Inhibiting Matrix Metalloproteinase-2/-9 and Urokinase through the PI3K/AKT/mTOR Signaling Pathway in Human Bladder Cancer Cells

by Te-Chih Cheng, Zhong-Hao Din, Jui-Hsin Su, Yu-Jen Wu and Chih-I Liu

Mar. Drugs 2017, 15(8), 238; https://doi.org/10.3390/md15080238 - 2 Aug 2017

Cited by 47 | Viewed by 4978

Abstract

Sinulariolide is a natural product extracted from the cultured-type soft coral Sinularia flexibilis, and possesses bioactivity against the movement of several types of cancer cells. However, the molecular pathway behind its effects on human bladder cancer remain poorly understood. Using a human bladder cancer cell line as an in vitro model, this study investigated the underlying mechanism of sinulariolide against cell migration/invasion in TSGH-8301 cells. We found that sinulariolide inhibited TSGH-8301 cell migration/invasion, and the effect was concentration-dependent. Furthermore, the protein expressions of matrix metalloproteinases (MMPs) MMP-2 and MMP-9, as well as urokinase, were significantly decreased after 24-h sinulariolide treatment. Meanwhile, the increased expression of tissue inhibitors of metalloproteinases (TIMPs) TIMP-1 and TIMP-2 were in parallel with an increased concentration of sinulariolide. Finally, the expressions of several key phosphorylated proteins in the mTOR signaling pathway were also downregulated by sinulariolide treatment. Our results demonstrated that sinulariolide has significant effects against TSGH-8301 cell migration/invasion, and its effects were associated with decreased levels of MMP-2/-9 and urokinase expression, as well as increased TIMP-1/TIMP-2 expression. The inhibitory effects were mediated by reducing phosphorylation proteins of the PI3K, AKT, and mTOR signaling pathway. The findings suggested that sinulariolide is a good candidate for advanced investigation with the aim of developing a new drug for the treatment of human bladder cancer. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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1262 KiB

Open AccessArticle

Sterols from the Octocoral Nephthea columnaris

by Ta-Yuan Whuang, Hong-Chieh Tsai, Yin-Di Su, Tsong-Long Hwang and Ping-Jyun Sung

Mar. Drugs 2017, 15(7), 212; https://doi.org/10.3390/md15070212 - 4 Jul 2017

Cited by 9 | Viewed by 3794

Abstract

Two new sterols, columnaristerols B (1) and C (2), along with two known analogues, 5,6-epoxylitosterol (3) and litosterol (4), were obtained from the octocoral Nephthea columnaris. The structures of new sterols 1 and 2 were elucidated by using spectroscopic methods and comparing the spectroscopic data with those of known related metabolites. Sterol 3 was found to suppress superoxide anion production and elastase secretion by human neutrophils. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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2516 KiB

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24-Methyl-Cholesta-5,24(28)-Diene-3β,19-diol-7β-Monoacetate Inhibits Human Small Cell Lung Cancer Growth In Vitro and In Vivo via Apoptosis Induction

by Ting-Wen Chung, Jui-Hsin Su, Chi-Chen Lin, Yi-Rong Li, Ya-Hsuan Chao, Sheng-Hao Lin and Hong-Lin Chan

Mar. Drugs 2017, 15(7), 210; https://doi.org/10.3390/md15070210 - 1 Jul 2017

Cited by 10 | Viewed by 4502

Abstract

24-methyl-cholesta-5,24(28)-diene-3β,19-diol-7β-monoacetate (MeCDDA) is a natural steroid compound isolated from a wild-type soft coral (Nephthea erecta). The present study aimed to investigate the anti-small cell lung cancer (SCLC) effects of MeCDDA in vitro and in vivo, as well as to elucidate its underlying mechanism. Our results indicated that H1688 and H146 cells show relevant sensitivity to MeCDDA, and the exposure to MeCDDA in SCLC cells caused dose-dependent growth inhibitory responses. In addition, MeCDDA treatment promoted cell apoptosis and increased the activities of caspases in H1688 cells, reducing the mitochondrial membrane potential and stimulating the release of cytochrome c into the cytosol. Along with the increase in Bax expression and reduction in Bcl-2, the MeCDDA treatment also significantly decreased Akt and mTOR phosphorylation. Finally, MeCDDA treatment in the mouse xenograft model of H1688 cells exhibited significant inhibition of tumor growth, corroborating MeCDDA as a potential pre-clinical candidate for the treatment of SCLC. Overall, our results demonstrate that the cytotoxic effects of MeCDDA towards H1688 and H146 cells, possibly through the activation of the mitochondrial apoptotic pathway and inhibition of the PI3K/Akt/mTOR pathway, merit further studies for its possible clinical application in chemotherapy. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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2119 KiB

Open AccessArticle

Isoprenoids from the Soft Coral Sarcophyton glaucum

by Chih-Hua Chao, Wen-Liang Li, Chiung-Yao Huang, Atallah F. Ahmed, Chang-Feng Dai, Yang-Chang Wu, Mei-Chin Lu, Chih-Chuang Liaw and Jyh-Horng Sheu

Mar. Drugs 2017, 15(7), 202; https://doi.org/10.3390/md15070202 - 27 Jun 2017

Cited by 24 | Viewed by 4837

Abstract

Five new isoprenoids, 3,4,8,16-tetra-epi-lobocrasol (1), 1,15β-epoxy-deoxysarcophine (2), 3,4-dihydro-4α,7β,8α-trihydroxy-Δ²-sarcophine (3), ent-sarcophyolide E (4), and 16-deacetyl- halicrasterol B (5) and ten known compounds 6‒15, were characterized from the marine soft coral Sarcophyton glaucum, collected off Taitung coastline. Their structures were defined by analyzing spectra data, especially 2D NMR and electronic circular dichroism (ECD). The structure of the known compound lobocrasol (7) was revised. Cytotoxicity potential of the isolated compounds was reported, too. Full article

(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)

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