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

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

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 26377

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Prof. Dr. Yang-Chang Wu

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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

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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

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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

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

Cnidaria
Porifera
Coral reef
Structure determination
Sponge

Published Papers (11 papers)

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Research

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11 pages, 2169 KiB

Open AccessArticle

Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum

by Hui-Chun Wang, Tzu-Yi Ke, Ya-Chen Ko, Jue-Jun Lin, Jui-Sheng Chang and Yuan-Bin Cheng

Mar. Drugs 2021, 19(10), 529; https://doi.org/10.3390/md19100529 - 22 Sep 2021

Cited by 9 | Viewed by 2580

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 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 (1–7) 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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12 pages, 2918 KiB

Open AccessArticle

Antimicrobial Terpenoids from South China Sea Soft Coral Lemnalia sp.

by Xia Yan, Han Ouyang, Wei Wang, Jing Liu, Te Li, Bin Wu, Xiaojun Yan and Shan He

Mar. Drugs 2021, 19(6), 294; https://doi.org/10.3390/md19060294 - 22 May 2021

Cited by 13 | Viewed by 2368

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 (1–3); a new aristolane-type sesquiterpenoid, 2-acetoxy-aristolane (4); four new decalin-type bicyclic diterpenes, named biofloranates A−D (5−8); a new serrulatane, named euplexaurene D (9); and a new aromadendrane-type diterpenoid cneorubin K (10), together with three known related compounds (11−13). The structures of the new compounds were elucidated by NMR spectroscopy, the Mosher’s method, and ECD analysis. Compounds 1–13 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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10 pages, 2126 KiB

Open AccessArticle

Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri

by Chia-Chi Peng, Tzu-Yin Huang, Chiung-Yao Huang, Tsong-Long Hwang and Jyh-Horng Sheu

Mar. Drugs 2021, 19(5), 260; https://doi.org/10.3390/md19050260 - 01 May 2021

Cited by 5 | Viewed by 2227

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, 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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8 pages, 1739 KiB

Open AccessArticle

Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella sp.

by Kuei-Hung Lai, Zheng-Hao Huang, Mohamed El-Shazly, Bo-Rong Peng, Wen-Chi Wei and Jui-Hsin Su

Mar. Drugs 2021, 19(4), 206; https://doi.org/10.3390/md19040206 - 06 Apr 2021

Cited by 7 | Viewed by 2462

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 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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8 pages, 2386 KiB

Open AccessArticle

8-Hydroxybriaranes from Octocoral Briareum stechei (Briareidae) (Kükenthal, 1908)

by Thanh-Hao Huynh, Su-Ying Chien, Junichi Tanaka, Zhi-Hong Wen, Yang-Chang Wu, Tung-Ying Wu and Ping-Jyun Sung

Mar. Drugs 2021, 19(3), 136; https://doi.org/10.3390/md19030136 - 28 Feb 2021

Cited by 6 | Viewed by 1847

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 S (3). The structures of briaranes 1–3 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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9 pages, 5414 KiB

Open AccessArticle

Cembranoids from Octocoral Lobophytum crassum (von Marenzeller, 1886)

by Yao-Tsung Yeh, Sung-Chun Lin, Gene-Hsiang Lee, Zhi-Hong Wen, Tsong-Long Hwang, Yu-Jen Wu, Jih-Jung Chen, Lee-Shing Fang, Mei-Kang Yuan and Ping-Jyun Sung

Mar. Drugs 2021, 19(3), 130; https://doi.org/10.3390/md19030130 - 27 Feb 2021

Cited by 4 | Viewed by 2268

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 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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16 pages, 4984 KiB

Open AccessArticle

Isoquinolinequinone Derivatives from a Marine Sponge (Haliclona sp.) Regulate Inflammation in In Vitro System of Intestine

by Yun Na Kim, Yeong Kwang Ji, Na-Hyun Kim, Nguyen Van Tu, Jung-Rae Rho and Eun Ju Jeong

Mar. Drugs 2021, 19(2), 90; https://doi.org/10.3390/md19020090 - 04 Feb 2021

Cited by 7 | Viewed by 2130

Abstract

Using bio-guided fractionation and based on the inhibitory activities of nitric oxide (NO) and prostaglandin E2 (PGE2), eight isoquinolinequinone derivatives (1–8) 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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14 pages, 3477 KiB

Open AccessArticle

Briarenols W–Z: Chlorine-Containing Polyoxygenated Briaranes from Octocoral Briareum stechei (Kükenthal, 1908)

by You-Ying Chen, Yi-Lin Zhang, Gene-Hsiang Lee, Lun Kelvin Tsou, Mingzi M. Zhang, Hsing-Pang Hsieh, Jih-Jung Chen, Chou-Yuan Ko, Zhi-Hong Wen and Ping-Jyun Sung

Mar. Drugs 2021, 19(2), 77; https://doi.org/10.3390/md19020077 - 31 Jan 2021

Cited by 4 | Viewed by 2099

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 (1–4), 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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6 pages, 521 KiB

Open AccessCommunication

Screening for Small Molecule Inhibitors of BMP-Induced Osteoblastic Differentiation from Indonesian Marine Invertebrates

by Hiroyuki Yamazaki, Satoshi Ohte, Henki Rotinsulu, Defny S. Wewengkang, Deiske A. Sumilat, Delfly B. Abdjul, Wilmar Maarisit, Magie M. Kapojos, Michio Namikoshi, Takenobu Katagiri, Hiroshi Tomoda and Ryuji Uchida

Mar. Drugs 2020, 18(12), 606; https://doi.org/10.3390/md18120606 - 30 Nov 2020

Cited by 5 | Viewed by 2432

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, 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 1–3 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 1–3 did not decrease the reporter activity, suggesting that they inhibit the downstream of the Smad transcriptional step in BMP signaling. Full article

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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10 pages, 1873 KiB

Open AccessArticle

Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)

by Yu-Chia Chang, Chih-Chao Chiang, Yuan-Shiun Chang, Jih-Jung Chen, Wei-Hsien Wang, Lee-Shing Fang, Hsu-Ming Chung, Tsong-Long Hwang and Ping-Jyun Sung

Mar. Drugs 2020, 18(11), 554; https://doi.org/10.3390/md18110554 - 06 Nov 2020

Cited by 12 | Viewed by 2284

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, 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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Review

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36 pages, 4192 KiB

Open AccessReview

Metabolities from Marine Sponges of the Genus Callyspongia: Occurrence, Biological Activity, and NMR Data

by Lucas Hilário Nogueira de Sousa, Rusceli Diego de Araújo, Déborah Sousa-Fontoura, Fabrício Gava Menezes and Renata Mendonça Araújo

Mar. Drugs 2021, 19(12), 663; https://doi.org/10.3390/md19120663 - 26 Nov 2021

Cited by 3 | Viewed by 2429

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 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

(This article belongs to the Special Issue Reef Cnidaria and Porifera as Sources of Bioactive Secondary Metabolites—Honoring the 70th Birthday of Professor Yang-Chang Wu)

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