Bioactive Compounds from Soft Corals and Their Derived Microorganisms

A special issue of Marine Drugs (ISSN 1660-3397). This special issue belongs to the section "Structural Studies on Marine Natural Products".

Deadline for manuscript submissions: closed (31 December 2024) | Viewed by 15715

Special Issue Editor


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Guest Editor
Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
Interests: natural product chemistry; bioactive compounds; drug discovery; structure determination
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Special Issue Information

Dear Colleagues,                

The ocean provides a vast array of habitats for various living organisms. In order to survive in extreme environments, marine organisms have to produce highly potent metabolites. Among marine organisms, soft corals are promising providers of marine bioactive compounds and have received increasing attention. Over the past few decades, a fairly large variety of bioactive secondary metabolites including terpenoids, diterpenoids, sesquiterpenoids, steroids, quinones, prostaglandins, ceramides, and other chemical compounds have been discovered in soft corals, which exhibit a spectrum of biological activities, such as antimicrobial, anti-angiogenic, anticancer, immunomodulatory, anti-inflammatory, antiviral, and antifouling activities.

This Special Issue focuses on bioactive compounds derived from marine soft corals and their derived microorganisms and offers researchers the opportunity to publish original work on various topics including, but not limited to, the following:

  1. Isolation, structure elucidation, and bioactivity of compounds from soft corals and their derived microorganisms;
  2. Characterization of proteins, enzymes, and saccharides from soft corals and their derived microorganisms;
  3. Design, synthesis, modification, and structure–activity relationship of the abovementioned compounds.

Dr. Yan-Bo Zeng
Guest Editor

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Keywords

  • soft corals
  • soft coral-derived microorganisms
  • marine natural products
  • bioactive compounds
  • chemical structures
  • biosynthetic pathway
  • pharmacological mechanism

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Published Papers (9 papers)

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Research

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12 pages, 1562 KiB  
Article
Bioactive Steroids with Structural Diversity from the South China Sea Soft Coral Lobophytum sp. and Sponge Xestospongia sp.
by Lin-Mao Ke, Zi-Ru Zhang, Song-Wei Li, Yan-Bo Zeng, Ming-Zhi Su and Yue-Wei Guo
Mar. Drugs 2025, 23(1), 36; https://doi.org/10.3390/md23010036 - 13 Jan 2025
Viewed by 557
Abstract
A chemical investigation of the soft coral Lobophytum sp. and the sponge Xestospongia sp. from the South China Sea led to the isolation of five steroids, including two new compounds (1 and 4) and one known natural product (3). [...] Read more.
A chemical investigation of the soft coral Lobophytum sp. and the sponge Xestospongia sp. from the South China Sea led to the isolation of five steroids, including two new compounds (1 and 4) and one known natural product (3). Compounds 13 were derived from the soft coral Lobophytum sp., while 4 and 5 were obtained from the sponge Xestospongia sp. The structures of these compounds were determined by extensive spectroscopic analysis, the time-dependent density functional theory–electronic circular dichroism (TDDFT-ECD) calculation method, and comparison with the spectral data previously reported in the literature. The antibacterial and anti-inflammatory activities of isolated compounds were evaluated in vitro. Compounds 13, 4, and 5 exhibited weak antibacterial activity against vancomycin-resistant Enterococcus faecium G1, Streptococcus parauberis KSP28, Photobacterium damselae FP2244, Lactococcus garvieae FP5245, and Pseudomonas aeruginosa ZJ028. Moreover, compound 3 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced NO production in RAW 264.7 cells, with an IC50 value of 13.48 μM. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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13 pages, 3180 KiB  
Article
Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral Sarcophyton tortuosum, and Their Antibacterial and PPAR-β Agonist Activities
by Min Sun, Songwei Li, Jianang Zeng, Yuewei Guo, Changyun Wang and Mingzhi Su
Mar. Drugs 2024, 22(12), 553; https://doi.org/10.3390/md22120553 - 10 Dec 2024
Viewed by 855
Abstract
Two new cembrane-derived tricyclic diterpenes belonging to the sarcophytin family, namely 4a-hydroxy-chatancin (1) and sarcotoroid (2), together with two known related ones (3 and 4), were isolated from the soft coral Sarcophyton tortuosum collected off [...] Read more.
Two new cembrane-derived tricyclic diterpenes belonging to the sarcophytin family, namely 4a-hydroxy-chatancin (1) and sarcotoroid (2), together with two known related ones (3 and 4), were isolated from the soft coral Sarcophyton tortuosum collected off Ximao Island in the South China Sea. The structures of the new compounds were elucidated by extensive spectroscopic analysis, a quantum mechanical nuclear magnetic resonance (QM-NMR) method, a time-dependent density functional theory electronic circular dichroism (TDDFT-ECD) calculation, X-ray diffraction analysis, and comparison with the reported data in the literature. A plausible biosynthetic pathway of compounds 14 was proposed, involving undergoing a transannular Diels–Alder cycloaddition. In the bioassay, the new compound 1 displayed significant inhibitory activities against the fish pathogens Streptococcus parauberis KSP28, oxytetracycline-resistant Streptococcus parauberis SPOF3K, and Photobacterium damselae FP2244, with MIC values of 9.1, 9.1, and 18.2 μg/mL, respectively. Furthermore, by conducting a luciferase reporter assay on rat liver Ac2F cells, compounds 1, 3, and 4 were evaluated for peroxisome proliferator-activated receptor (PPAR) transcriptional activity, and compound 3 showed selective PPAR-β agonist activity at a concentration of 10 μΜ. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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12 pages, 1754 KiB  
Article
Cembranoid Diterpenes from South China Sea Soft Coral Sarcophyton crassocaule
by Hanyang Peng, Yanbo Zeng, Rui Zhang, Li Yang, Fei Wu, Cuijuan Gai, Jingzhe Yuan, Wenjun Chang, Haofu Dai and Xiachang Wang
Mar. Drugs 2024, 22(12), 536; https://doi.org/10.3390/md22120536 - 29 Nov 2024
Viewed by 902
Abstract
Cembranoid diterpenes are characteristic compounds of soft corals with diverse structures and significant activities, making them an important source of drug lead compounds. In this paper, five new cembranoid diterpenes, meijicrassolins A–E (15), were isolated from the soft coral [...] Read more.
Cembranoid diterpenes are characteristic compounds of soft corals with diverse structures and significant activities, making them an important source of drug lead compounds. In this paper, five new cembranoid diterpenes, meijicrassolins A–E (15), were isolated from the soft coral Sarcophyton crassocaule, along with five previously reported compounds (610). The structures and absolute configuration for new compounds 15 were assigned by extensive spectroscopic analysis, single-crystal X-ray crystallography, quantum mechanical nuclear magnetic resonance (QM-NMR), and time-dependent density functional theory/electronic circular dichroism (TDDFT/ECD) calculations. Compounds 3, 4, and 9 showed moderate inhibition of nitric oxide generation in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Overall, our research results have enriched the library of secondary metabolites from soft corals, providing more molecular entities for subsequent research and development of related compounds. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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8 pages, 761 KiB  
Communication
New Meroterpenes from South China Sea Soft Coral Litophyton brassicum
by Xiaoyi Chen, Jiahui Zhang, Jiayu Yang, Bing Li, Te Li, Han Ouyang, Wenhan Lin, Hongyu Hu, Xia Yan and Shan He
Mar. Drugs 2024, 22(9), 392; https://doi.org/10.3390/md22090392 - 30 Aug 2024
Viewed by 1359
Abstract
A chemical investigation of the extracts from the soft coral Litophyton brassicum led to the isolation and identification of four new meroterpenes, brassihydroxybenzoquinone A and B (1 and 2) and brassinaphthoquinone A and B (3 and 4), along with [...] Read more.
A chemical investigation of the extracts from the soft coral Litophyton brassicum led to the isolation and identification of four new meroterpenes, brassihydroxybenzoquinone A and B (1 and 2) and brassinaphthoquinone A and B (3 and 4), along with two known related meroterpenes (5 and 6). Their structures were elucidated using high-resolution electrospray ionization mass spectrometry (HRESIMS), nuclear magnetic resonance (NMR) spectroscopy, and a comparison with the literature data. All compounds were evaluated for antibacterial activity against six pathogenic bacterial strains and for cytotoxic activity against three cancer cell lines. In the cytotoxic assay, all compounds were inactive at 10 μM against the A549, HeLa, and MDA-MB-231 cell lines. In the antibacterial assay, compounds 1 and 2 exhibited moderate inhibitory activity with minimum inhibitory concentrations (MIC) ranging from 8 to 64 μg/mL. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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13 pages, 1518 KiB  
Article
Marine Prostanoids with Cytotoxic Activity from Octocoral Clavularia spp.
by Ming-Ya Cheng, I-Chi Hsu, Shi-Ying Huang, Ya-Ting Chuang, Tzi-Yi Ke, Hsueh-Wei Chang, Tian-Huei Chu, Ching-Yeu Chen and Yuan-Bin Cheng
Mar. Drugs 2024, 22(5), 219; https://doi.org/10.3390/md22050219 - 14 May 2024
Cited by 1 | Viewed by 1499
Abstract
Octocoral of the genus Clavularia is a kind of marine invertebrate possessing abundant cytotoxic secondary metabolites, such as prostanoids and dolabellanes. In our continuous natural product study of C. spp., two previously undescribed prostanoids [clavulone I-15-one (1) and 12-O-deacetylclavulone [...] Read more.
Octocoral of the genus Clavularia is a kind of marine invertebrate possessing abundant cytotoxic secondary metabolites, such as prostanoids and dolabellanes. In our continuous natural product study of C. spp., two previously undescribed prostanoids [clavulone I-15-one (1) and 12-O-deacetylclavulone I (2)] and eleven known analogs (313) were identified. The structures of these new compounds were elucidated based on analysis of their 1D and 2D NMR, HRESIMS, and IR data. Additionally, all tested prostanoids (1 and 313) showed potent cytotoxic activities against the human oral cancer cell line (Ca9-22). The major compound 3 showed cytotoxic activity against the Ca9-22 cells with the IC50 value of 2.11 ± 0.03 μg/mL, which echoes the cytotoxic effect of the coral extract. In addition, in silico tools were used to predict the possible effects of isolated compounds on human tumor cell lines and nitric oxide production, as well as the pharmacological potentials. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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10 pages, 4593 KiB  
Article
New Diterpenes and Diterpene Glycosides with Antibacterial Activity from Soft Coral Lemnalia bournei
by Xiao Han, Huiting Wang, Bing Li, Xiaoyi Chen, Te Li, Xia Yan, Han Ouyang, Wenhan Lin and Shan He
Mar. Drugs 2024, 22(4), 157; https://doi.org/10.3390/md22040157 - 29 Mar 2024
Cited by 1 | Viewed by 1889
Abstract
Five new biflorane-type diterpenoids, biofloranates E–I (15), and two new bicyclic diterpene glycosides, lemnaboursides H–I (67), along with the known lemnabourside, were isolated from the South China Sea soft coral Lemnalia bournei. Their chemical [...] Read more.
Five new biflorane-type diterpenoids, biofloranates E–I (15), and two new bicyclic diterpene glycosides, lemnaboursides H–I (67), along with the known lemnabourside, were isolated from the South China Sea soft coral Lemnalia bournei. Their chemical structures and stereochemistry were determined based on extensive spectroscopic methods, including time-dependent density functional theory (TDDFT) ECD calculations, as well as a comparison of them with the reported values. The antibacterial activities of the isolated compounds were evaluated against five pathogenic bacteria, and all of these diterpenes and diterpene glycosides showed antibacterial activities against Staphylococcus aureus and Bacillus subtilis, with MICs ranging from 4 to 64 µg/mL. In addition, these compounds did not exhibit noticeable cytotoxicities on A549, Hela, and HepG2 cancer cell lines, at 20 μM. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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11 pages, 2179 KiB  
Article
Lemneolemnanes A–D, Four Uncommon Sesquiterpenoids from the Soft Coral Lemnalia sp.
by Yuan Zong, Tian-Yun Jin, Jun-Jie Yang, Kun-Ya Wang, Xing Shi, Yue Zhang and Ping-Lin Li
Mar. Drugs 2024, 22(4), 145; https://doi.org/10.3390/md22040145 - 26 Mar 2024
Cited by 1 | Viewed by 1656
Abstract
Four undescribed sesquiterpenoids, lemneolemnanes A–D (14), have been isolated from the marine soft coral Lemnalia sp. The absolute configurations of the stereogenic carbons of 14 were determined by single-crystal X-ray crystallographic analysis. Compounds 1 and 2 are [...] Read more.
Four undescribed sesquiterpenoids, lemneolemnanes A–D (14), have been isolated from the marine soft coral Lemnalia sp. The absolute configurations of the stereogenic carbons of 14 were determined by single-crystal X-ray crystallographic analysis. Compounds 1 and 2 are epimers at C-3 and have an unusual skeleton with a formyl group on C-6. Compound 3 possesses an uncommonly rearranged carbon skeleton, while 4 has a 6/5/5 tricyclic system. Compound 1 showed significant anti-Alzheimer’s disease (AD) activity in a humanized Caenorhabditis elegans AD pathological model. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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16 pages, 4884 KiB  
Article
In Vitro Insights into the Role of 7,8-Epoxy-11-Sinulariolide Acetate Isolated from Soft Coral Sinularia siaesensis in the Potential Attenuation of Inflammation and Osteoclastogenesis
by Lin-Mao Ke, Dan-Dan Yu, Ming-Zhi Su, Liao Cui and Yue-Wei Guo
Mar. Drugs 2024, 22(2), 95; https://doi.org/10.3390/md22020095 - 19 Feb 2024
Cited by 1 | Viewed by 2275
Abstract
The balance between bone-resorbing osteoclasts and bone-forming osteoblasts is essential for the process of bone remodeling. Excessive osteoclast differentiation plays a pivotal role in the pathogenesis of bone diseases such as rheumatoid arthritis and osteoporosis. In the present study, we examined whether 7,8-epoxy-11-sinulariolide [...] Read more.
The balance between bone-resorbing osteoclasts and bone-forming osteoblasts is essential for the process of bone remodeling. Excessive osteoclast differentiation plays a pivotal role in the pathogenesis of bone diseases such as rheumatoid arthritis and osteoporosis. In the present study, we examined whether 7,8-epoxy-11-sinulariolide acetate (Esa), a marine natural product present in soft coral Sinularia siaesensis, attenuates inflammation and osteoclastogenesis in vitro. The results indicated that Esa significantly inhibited lipopolysaccharide (LPS)-induced inflammation model of RAW264.7 cells and suppressed receptor activator for nuclear factor-κB ligand (RANKL)-triggered osteoclastogenesis. Esa significantly down-regulated the protein expression of iNOS, COX-2, and TNF-α by inhibiting the NF-κB/MAPK/PI3K pathways and reducing the release of reactive oxygen species (ROS) in RAW264.7 macrophages. Besides, Esa treatment significantly inhibited osteoclast differentiation and suppressed the expression of osteoclast-specific markers such as NFATC1, MMP-9, and CTSK proteins. These findings suggest that Esa may be a potential agent for the maintenance of bone homeostasis associated with inflammation. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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Review

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48 pages, 5981 KiB  
Review
An Overview of Secondary Metabolites from Soft Corals of the Genus Capnella over the Five Decades: Chemical Structures, Pharmacological Activities, NMR Data, and Chemical Synthesis
by Can-Qi Liu, Qi-Bin Yang, Ling Zhang and Lin-Fu Liang
Mar. Drugs 2024, 22(9), 402; https://doi.org/10.3390/md22090402 - 2 Sep 2024
Viewed by 3424
Abstract
There has been no specific review on the secondary metabolites from soft corals of the genus Capnella till now. In this work, all secondary metabolites from different species of the title genus were described. It covered the first work from 1974 to May [...] Read more.
There has been no specific review on the secondary metabolites from soft corals of the genus Capnella till now. In this work, all secondary metabolites from different species of the title genus were described. It covered the first work from 1974 to May 2024, spanning five decades. In the viewpoint of the general structural features, these chemical constituents were classified into four groups: sesquiterpenes, diterpenes, steroids, and lipids. Additionally, the 1H and 13C NMR data of these metabolites were provided when available in the literature. Among them, sesquiterpenes were the most abundant chemical compositions from soft corals of the genus Capnella. A variety of pharmacological activities of these compounds were evaluated, such as cytotoxic, antibacterial, antifungal, and anti-inflammatory activities. In addition, the chemical synthesis works of several representative sesquiterpenes were provided. This review aims to provide an up-to-date knowledge of the chemical structures, pharmacological activities, and chemical synthesis of the chemical constituents from soft corals of the genus Capnella. Full article
(This article belongs to the Special Issue Bioactive Compounds from Soft Corals and Their Derived Microorganisms)
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