Special Issue "Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu"

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

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 16591

Special Issue Editors

Prof. Dr. Yang-Chang Wu
E-Mail Website
Honorary Guest Editor
Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung 404333, Taiwan
Interests: natural product medicinal chemistry; bioactive compounds; translational research on Chinese herbal medicine and natural medicinal products—functional food and new drug development
Prof. Dr. Ping-Jyun Sung
E-Mail Website
Guest Editor
National Museum of Marine Biology and Aquarium, Pingtung 944401, Taiwan
Interests: marine natural products; marine chemical ecology; bioactive substances from cultured marine invertebrates
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Yuan-Bin Cheng
E-Mail Website
Guest Editor
Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804201, Taiwan
Interests: natural product chemistry; establishment and application of natural extract bank
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Please join us in extending, on the occasion of his 70th birthday, our congratulations to Professor Yang-Chang Wu, who has for many decades been a pioneer in the field of natural product chemistry and marine drugs. It is a great pleasure and honor for us to announce a new Special Issue of Marine Drugs to celebrate Professor Wu’s achievements.

Professor Yang-Chang Wu was born in Chiayi City, Taiwan in 1951. He received his Ph.D. in pharmacognosy from the College of Pharmacy, Kaohsiung Medical University (KMU), Taiwan, under the supervision of the late Professor Sheng-The Lu in 1986. After working as a postdoctoral fellow with Professor Yoshimasa Hirata at Meijo University, Japan, and Professor Kuo-Hsiung Lee at the University of North Carolina (UNC), Chapel Hill, USA, from 1986 to 1987, in 1990 he became professor at the College of Pharmacy, KMU, and director of the Graduate Institute of Natural Products (GINP) from 1992 to 2006. Later, he served as the dean of the Office of Research and Development at KMU from 2006 to 2009. Due to his significant contribution to research on natural products, he was selected as the chair professor and vice-president as well as dean of the School of Pharmacy at China Medical University (CMU), Taiwan, from 2010 to 2017. In 2017, he returned to KMU and served as the Chair Professor of the GINP. In 2019, he returned to CMU and served as the Chair Professor of the Graduate Institute of Integrated Medicine and Director of the Chinese Medicine Research and Development Center.

In 2007 and 2010, he was awarded by the Ming-Ning Wang and TienTe Lee Foundations for outstanding merit and high scholastic achievement of medical and pharmaceutical research, respectively. In 2009, he received the National Science Council Outstanding Research Outstanding Research Award in Taiwan.

Professor Wu has served as an editorial board number of 6 journals and a referee for about 40 journals. He is also an outstanding member of the American Society of Pharmacognosy. To date, Prof. Wu has published more than 610 research articles in SCI journals, has been granted more than 40 patents, and has cooperated with more 20 industry-academic organizations. Prof. Wu has transferred six patents/technologies to the industry.

In the beginning of 2021, he will be 70 years old. One’s 70th birthday is a significant milestone among Taiwanese people, often cited as the “Years from the Heart” in the Taiwanese language, which originally came from a Chinese classic, The Analects of Confucius, written about 2600 years ago by Confucius. Professor Wu is still quite active as a scientist following his move to CMU in 2019, as a Director of the Chinese Medicine Research and Development Center. As a result, we can find a number of his former colleagues and students in the fields of academia and industry. On behalf of Prof. Wu’s former and present colleagues and students, then, I would like to express our sincerest wishes for a happy “Years from the Heart” and a fruitful new decade in his life. In this Special Issue of Marine Drugs, some of these colleagues will contribute their most interesting research results in marine natural product chemistry.

This Special Issue, which is titled “Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites”, will focus on the diversity of chemical structures and biomedical activities of the natural products found in marine invertebrates, which have attracted the attention of researchers in the field of natural product chemistry. After nearly 40 years of research, considerable progress and development in various biomedical applications have been made. The cnidarians and sponges (Porifera) in coral reef areas have evolved to produce highly complex marine natural products due to their vast biological diversity and have been proven to be the most abundant source of marine natural compounds. These compounds have been shown to have a wide range of biomedical activities, such as cytotoxicity, anti-inflammation, antimicrobial activity, etc. The main purpose of this Special Issue, thus, is to explore the structural analysis and biological activity of the natural compounds contained in cnidaria and seawater sponges (Porifera) from coral reef areas.


Prof. Dr. Yang-Chang Wu
Prof. Dr. Ping-Jyun Sung
Prof. Dr. Yuan-Bin Cheng
Guest Editors

Manuscript Submission Information

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Keywords

  • Cnidaria
  • Porifera
  • Coral reef
  • Structure determination
  • Sponge

Published Papers (11 papers)

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Research

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Article
Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
Mar. Drugs 2021, 19(10), 529; https://doi.org/10.3390/md19100529 - 22 Sep 2021
Viewed by 1475
Abstract
To discover the new medical entity from edible marine algae, our continuously natural product investigation focused on endophytes from marine macroalgae Grateloupia sp. Two new azaphilones, 8a-epi-hypocrellone A (1), 8a-epi-eupenicilazaphilone C (2), together with five [...] Read more.
To discover the new medical entity from edible marine algae, our continuously natural product investigation focused on endophytes from marine macroalgae Grateloupia sp. Two new azaphilones, 8a-epi-hypocrellone A (1), 8a-epi-eupenicilazaphilone C (2), together with five known azaphilones, hypocrellone A (3), eupenicilazaphilone C (4), ((1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde (5), sclerotiorin (6), and isochromophilone IV (7) were isolated from the alga-derived fungus Penicillium sclerotiorum. The structures of isolated azaphilones (17) were elucidated by spectrometric identification, especially HRESIMS, CD, and NMR data analyses. Concerning bioactivity, cytotoxic, anti-inflammatory, and anti-fibrosis activities of those isolates were evaluated. As a result, compound 1 showed selective toxicity toward neuroblastoma cell line SH-SY5Y among seven cancer and one fibroblast cell lines. 20 μM of compounds 1, 3, and 7 inhibited the TNF-α-induced NFκB phosphorylation but did not change the NFκB activity. Compounds 2 and 6 respectively promoted and inhibited SMAD-mediated transcriptional activities stimulated by TGF-β. Full article
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Article
Antimicrobial Terpenoids from South China Sea Soft Coral Lemnalia sp.
Mar. Drugs 2021, 19(6), 294; https://doi.org/10.3390/md19060294 - 22 May 2021
Cited by 4 | Viewed by 1472
Abstract
Chemical investigation of the South China Sea soft coral Lemnalia sp. afforded 13 structurally diverse terpenoids, including three new neolemnane sesquiterpene lineolemnenes E–G (13); a new aristolane-type sesquiterpenoid, 2-acetoxy-aristolane (4); four new decalin-type bicyclic diterpenes, named biofloranates [...] Read more.
Chemical investigation of the South China Sea soft coral Lemnalia sp. afforded 13 structurally diverse terpenoids, including three new neolemnane sesquiterpene lineolemnenes E–G (13); a new aristolane-type sesquiterpenoid, 2-acetoxy-aristolane (4); four new decalin-type bicyclic diterpenes, named biofloranates A−D (58); a new serrulatane, named euplexaurene D (9); and a new aromadendrane-type diterpenoid cneorubin K (10), together with three known related compounds (1113). The structures of the new compounds were elucidated by NMR spectroscopy, the Mosher’s method, and ECD analysis. Compounds 113 were tested in a wide panel of biological assays. Lineolemnene J (3) showed weak cytotoxicity against the CCRF-CEM cancer cell line. The isolated new diterpenes, except euplexaurene D (9), demonstrated moderate antimicrobial activity against Bacillus subtilis and Staphylococcus aureus with a MIC of 4−64 μg/mL. Compound 2 exhibited a mild inhibitory effect against influenza A H1N1 virus (IC50 = 5.9 µM). Full article
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Article
Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri
Mar. Drugs 2021, 19(5), 260; https://doi.org/10.3390/md19050260 - 01 May 2021
Cited by 2 | Viewed by 1440
Abstract
Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, [...] Read more.
Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, MS, and 1D and 2D NMR data. Further, the absolute configuration of both compounds was determined by the comparison of CD spectra with that of isosarcophine (3). Notably, cherbonolide N (2) possesses the unique cembranoidal scaffold of tetrahydrooxepane with the 12,17-ether linkage fusing with a γ-lactone. In addition, the assay for cytotoxicity of both new compounds revealed that they showed to be noncytotoxic toward the proliferation of A549, DLD-1, and HuCCT-1 cell lines. Moreover, the anti-inflammatory activities of both metabolites were carried out by measuring the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced generation of superoxide anion and elastase release in the primary human neutrophils. Cherbonolide N (2) was found to reduce the generation of superoxide anion (20.6 ± 6.8%) and the elastase release (30.1 ± 3.3%) in the fMLF/CB-induced human neutrophils at a concentration of 30 μM. Full article
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Article
Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella sp.
Mar. Drugs 2021, 19(4), 206; https://doi.org/10.3390/md19040206 - 06 Apr 2021
Cited by 6 | Viewed by 1656
Abstract
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 [...] Read more.
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. Full article
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Article
8-Hydroxybriaranes from Octocoral Briareum stechei (Briareidae) (Kükenthal, 1908)
Mar. Drugs 2021, 19(3), 136; https://doi.org/10.3390/md19030136 - 28 Feb 2021
Cited by 5 | Viewed by 1270
Abstract
Chemical investigation of the octocoral Briareum stechei, collected in the Ie Island, Okinawa, Japan, resulted in the isolation of a new briarane-type diterpenoid, briastecholide A (1), as well as the previously reported metabolites, solenolide C (2) and briarenolide [...] Read more.
Chemical investigation of the octocoral Briareum stechei, collected in the Ie Island, Okinawa, Japan, resulted in the isolation of a new briarane-type diterpenoid, briastecholide A (1), as well as the previously reported metabolites, solenolide C (2) and briarenolide S (3). The structures of briaranes 13 were characterized through spectroscopic analysis, and the absolute configuration of 2 was corroborated by a single-crystal X-ray diffraction analysis. Briarane 3 exhibited bioactivity against the protein expression of inducible nitric oxide synthase (iNOS). Full article
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Article
Cembranoids from Octocoral Lobophytum crassum (von Marenzeller, 1886)
Mar. Drugs 2021, 19(3), 130; https://doi.org/10.3390/md19030130 - 27 Feb 2021
Viewed by 1539
Abstract
Two cembranoids, including a new compound, lobocrassin I (1), as well as a known analogue, lobohedleolide (2), were obtained by solvent extraction from octocoral Lobophytum crassum. This study employed a spectroscopic approach to establish the structures of these [...] Read more.
Two cembranoids, including a new compound, lobocrassin I (1), as well as a known analogue, lobohedleolide (2), were obtained by solvent extraction from octocoral Lobophytum crassum. This study employed a spectroscopic approach to establish the structures of these two cembranoids, and utilized single-crystal X-ray diffraction analysis to determine their absolute configurations. The results of biological activity assays demonstrated that cembranoid 2 exhibited bioactivity against the protein expressions of inducible nitric oxide synthase (iNOS) lipopolysaccharide (LPS)-treated RAW 264.7 mouse macrophage cells. Full article
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Article
Isoquinolinequinone Derivatives from a Marine Sponge (Haliclona sp.) Regulate Inflammation in In Vitro System of Intestine
Mar. Drugs 2021, 19(2), 90; https://doi.org/10.3390/md19020090 - 04 Feb 2021
Cited by 1 | Viewed by 1325
Abstract
Using bio-guided fractionation and based on the inhibitory activities of nitric oxide (NO) and prostaglandin E2 (PGE2), eight isoquinolinequinone derivatives (18) were isolated from the marine sponge Haliclona sp. Among these, methyl O-demethylrenierate (1) is a [...] Read more.
Using bio-guided fractionation and based on the inhibitory activities of nitric oxide (NO) and prostaglandin E2 (PGE2), eight isoquinolinequinone derivatives (18) were isolated from the marine sponge Haliclona sp. Among these, methyl O-demethylrenierate (1) is a noble ester, whereas compounds 2 and 3 are new O-demethyl derivatives of known isoquinolinequinones. Compound 8 was assigned as a new 21-dehydroxyrenieramycin F. Anti-inflammatory activities of the isolated compounds were tested in a co-culture system of human epithelial Caco-2 and THP-1 macrophages. The isolated derivatives showed variable activities. O-demethyl renierone (5) showed the highest activity, while 3 and 7 showed moderate activities. These bioactive isoquinolinequinones inhibited lipopolysaccharide and interferon gamma-induced production of NO and PGE2. Expression of inducible nitric oxide synthase, cyclooxygenase-2, and the phosphorylation of MAPKs were down-regulated in response to the inhibition of NF-κB nuclear translocation. In addition, nuclear translocation was markedly promoted with a subsequent increase in the expression of HO-1. Structure-activity relationship studies showed that the hydroxyl group in 3 and 5, and the N-formyl group in 7 may be key functional groups responsible for their anti-inflammatory activities. These findings suggest the potential use of Haliclona sp. and its metabolites as pharmaceuticals treating inflammation-related diseases including inflammatory bowel disease. Full article
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Article
Briarenols W–Z: Chlorine-Containing Polyoxygenated Briaranes from Octocoral Briareum stechei (Kükenthal, 1908)
Mar. Drugs 2021, 19(2), 77; https://doi.org/10.3390/md19020077 - 31 Jan 2021
Cited by 3 | Viewed by 1350
Abstract
Briareum stechei is proven to be a rich source of 3,8-cyclized cembranoids (briarane) with a bicyclo[8.4.0] carbon core. In the present study, four previously unreported briaranes, briarenols W–Z (14), along with solenolide A (5), briarenolide M ( [...] Read more.
Briareum stechei is proven to be a rich source of 3,8-cyclized cembranoids (briarane) with a bicyclo[8.4.0] carbon core. In the present study, four previously unreported briaranes, briarenols W–Z (14), along with solenolide A (5), briarenolide M (6), briaexcavatolide F (7), and brianolide (8), were isolated and characterized through spectroscopic analysis, and the absolute configuration of 8 was corroborated by a single-crystal x-ray diffraction analysis. Briaranes 2 and 5 were found to induce significant inflammatory activity in lipopolysaccharide (LPS)-induced RAW 264.7 mouse macrophage cells by enhancing the expression of the inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins. Full article
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Communication
Screening for Small Molecule Inhibitors of BMP-Induced Osteoblastic Differentiation from Indonesian Marine Invertebrates
Mar. Drugs 2020, 18(12), 606; https://doi.org/10.3390/md18120606 - 30 Nov 2020
Cited by 5 | Viewed by 1605
Abstract
Fibrodysplasia ossificans progressiva (FOP) is a rare congenital disorder with heterotopic ossification (HO) in soft tissues. The abnormal activation of bone morphogenetic protein (BMP) signaling by a mutant activin receptor-like kinase-2 (ALK2) leads to the development of HO in FOP patients, and, thus, [...] Read more.
Fibrodysplasia ossificans progressiva (FOP) is a rare congenital disorder with heterotopic ossification (HO) in soft tissues. The abnormal activation of bone morphogenetic protein (BMP) signaling by a mutant activin receptor-like kinase-2 (ALK2) leads to the development of HO in FOP patients, and, thus, BMP signaling inhibitors are promising therapeutic applications for FOP. In the present study, we screened extracts of 188 Indonesian marine invertebrates for small molecular inhibitors of BMP-induced alkaline phosphatase (ALP) activity, a marker of osteoblastic differentiation in a C2C12 cell line stably expressing ALK2(R206H) (C2C12(R206H) cells), and identified five marine sponges with potent ALP inhibitory activities. The activity-guided purification of an EtOH extract of marine sponge Dysidea sp. (No. 256) resulted in the isolation of dysidenin (1), herbasterol (2), and stellettasterol (3) as active components. Compounds 13 inhibited ALP activity in C2C12(R206H) cells with IC50 values of 2.3, 4.3, and 4.2 µM, respectively, without any cytotoxicity, even at 18.4–21.4 µM. The direct effects of BMP signaling examined using the Id1WT4F-luciferase reporter assay showed that compounds 13 did not decrease the reporter activity, suggesting that they inhibit the downstream of the Smad transcriptional step in BMP signaling. Full article
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Article
Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)
Mar. Drugs 2020, 18(11), 554; https://doi.org/10.3390/md18110554 - 06 Nov 2020
Cited by 8 | Viewed by 1427
Abstract
Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, [...] Read more.
Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC50 values of 11.22 and 23.53 μM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC50 value of 7.63 μM. Full article
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Review

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Review
Metabolities from Marine Sponges of the Genus Callyspongia: Occurrence, Biological Activity, and NMR Data
Mar. Drugs 2021, 19(12), 663; https://doi.org/10.3390/md19120663 - 26 Nov 2021
Cited by 1 | Viewed by 1186
Abstract
The genus Callyspongia (Callyspongiidae) encompasses a group of demosponges including 261 described species, of which approximately 180 have been accepted after taxonomic reviews. The marine organisms of Callyspongia are distributed in tropical ecosystems, especially in the central and western Pacific, but also in [...] Read more.
The genus Callyspongia (Callyspongiidae) encompasses a group of demosponges including 261 described species, of which approximately 180 have been accepted after taxonomic reviews. The marine organisms of Callyspongia are distributed in tropical ecosystems, especially in the central and western Pacific, but also in the regions of the Indian, the West Atlantic, and the East Pacific Oceans. The reason for the interest in the genus Callyspongia is related to its potential production of bioactive compounds. In this review, we group the chemical information about the metabolites isolated from the genus Callyspongia, as well as studies of the biological activity of these compounds. Through NMR data, 212 metabolites were identified from genus Callyspongia (15 species and Callyspongia sp.), belonging to classes such as polyacetylenes, terpenoids, steroids, alkaloids, polyketides, simple phenols, phenylpropanoids, nucleosides, cyclic peptides, and cyclic depsipeptides. A total of 109 molecules have been reported with bioactive activity, mainly cytotoxic and antimicrobial (antibacterial and antifungal) action. Thus, we conclude that polyacetylenes, terpenoids and steroids correspond to the largest classes of compounds of the genus, and that future research involving the anticancer action of the species’ bioactive metabolites may become relevant. Full article
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