Marine Natural Product Chemistry: A Themed Issue Dedicated to Prof. Dr. Peter Proksch on His Research Career

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

Deadline for manuscript submissions: closed (15 November 2021) | Viewed by 72870

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Guest Editor
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China
Interests: natural product chemistry; bioactive compounds; drug discovery; structure determination
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Guest Editor

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Guest Editor
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
Interests: marine natural products; isolation and structural confirmation; bioactivity; lead compounds; marine fungi
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear colleagues,

Prof. Dr. Peter Proksch is a distinguished and internationally known natural product chemist who devoted most of his professional career studying marine natural products derived from benthic macro-organisms, mainly sponges, molluscs and tunicates, and from fungi as well. His research interests focus on structure elucidation and mode of action of new bioactive metabolites with potential application in pharmaceutical sciences and in agriculture, on chemical ecology and natural functions of secondary metabolites as well as on co-cultivation techniques to activate silent biogenetic gene clusters of microorganisms to biosynthesize novel bioactive metabolites. Co-cultivation of micro-organisms relies on microbial crosstalk, which could induce the expression of cryptic natural products and/or strongly enhanced accumulation of constitutively present metabolites when compared to axenic microbial cultures.

Representative examples of his research findings include:

  • The discovery of wound-induced bioconversion of sponge-derived brominated isoxazoline alkaloids in Aplysina sponges, thereby yielding bioactive low molecular weight compounds such as aeroplysinin-1 that show pronounced antibiotic activity against many Gram-positive and -negative bacteria;
  • The discovery of the pronounced anti-fouling activity of brominated tyrosine-derived alkaloids such as dibromohemibastadin (DBHB) from the sponge Ianthella basta through inhibition of phenoloxidases that are involved in settling of macrofouling organisms such as barnacles;
  • The study of numerous antiproliferative and antibiotically active marine natural products from benthic invertebrates and fungi alike, as exemplified by phomoxanthone A from the mangrove-derived endophytic fungus Phomopsis longicolla. Phomoxanthone A is a new and unique mitochondrial toxin, which causes complete mitochondrial fragmentation in less than one minute, thereby provoking programmed cell death in the form of apoptosis.

Prof. Dr. Proksch has published over 600 peer-reviewed original papers, review articles and book chapters. Moreover, he has supervised more than 80 doctoral students and has maintained over the years numerous productive collaborations with partners from China, Indonesia, India, Vietnam, Egypt, Cameroon and Nigeria. During these international collaborations, foreign students both at the master and PhD level as well as postdoctoral fellows received their training in the lab of Prof. Dr. Proksch. Many of them now hold faculty positions in their home countries.

The achievements of Prof. Dr. Proksch in science have been internationally recognized through awards, numerous prizes and honorary positions he had received such as:

  • The Commemorative Medal of the Vietnamese Academy of Sciences (Vietnam) in 2008;
  • The Qilu Friendship Award of Shandong Province (P.R. China) in 2014;
  • The prestigious National Friendship Award of the Peoples Republic of China in 2016, which is only awarded for foreign experts who have made outstanding contributions to China's economic and social progress;
  • The Coconut Island Commemorative Award (China) in 2017; and
  • An Honorary Doctorate from the University of Abuja (Nigeria) in 2017.

Moreover, Prof. Dr. Proksch currently holds Honorary Professorships in Chinese academic institutions at the Three Gorges University and Chinese Academy of Tropical Agricultural Science (P.R. China).

Prof. Dr. Peter Proksch was born in Leipzig in 1953 and studied Biology at the University of Cologne, where he received his doctorate in 1980. For two years (1980–1982), he was a postdoctoral fellow at the University of California in Irvine (USA), then returned back to Germany where he held academic positions at the University of Cologne (1982–1985), the Technical University of Braunschweig (1986–1989) and the University of Wuerzburg (1990–1999). In 1999, he moved to the Heinrich-Heine University Düsseldorf as a Full Professor and Head of the Institute for Pharmaceutical Biology and Biotechnology until his retirement in 2019.

Marine Drugs is very pleased to host a Special Issue in honour of Prof. Dr. Peter Proksch, who served as Editor in Chief for Marine Drugs from 2005 to 2009, for his excellent research contribution, and we invite scientists to submit original contributions to “Marine Natural Product Chemistry: A Themed Issue Dedicated to Prof. Dr. Peter Proksch on His Research Career”.

Prof. Dr. Bin-Gui Wang
Dr. RuAngelie Edrada-Ebel
Prof. Dr. Chang-Yun Wang
Guest Editors

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Published Papers (20 papers)

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Editorial

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1 pages, 135 KiB  
Editorial
Looking Back at My Years in Marine Natural Products Chemistry
by Peter Proksch
Mar. Drugs 2022, 20(3), 161; https://doi.org/10.3390/md20030161 - 24 Feb 2022
Viewed by 1495
Abstract
When I started to work on marine natural products some thirty years ago I was attracted to this fascinating field of science by the exotic environment, the colourful shapes of (mostly) marine invertebrates and their complex ecological interactions [...] Full article

Research

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10 pages, 1140 KiB  
Communication
Apoptotic Activity of New Oxisterigmatocystin Derivatives from the Marine-Derived Fungus Aspergillus nomius NC06
by Muh. Ade Artasasta, Yanwirasti Yanwirasti, Muhammad Taher, Akmal Djamaan, Ni Putu Ariantari, Ru Angelie Edrada-Ebel and Dian Handayani
Mar. Drugs 2021, 19(11), 631; https://doi.org/10.3390/md19110631 - 11 Nov 2021
Cited by 9 | Viewed by 3144
Abstract
Sponge-derived fungi have recently attracted attention as an important source of interesting bioactive compounds. Aspergillus nomius NC06 was isolated from the marine sponge Neopetrosia chaliniformis. This fungus was cultured on rice medium and yielded four compounds including three new oxisterigmatocystins, namely, J, [...] Read more.
Sponge-derived fungi have recently attracted attention as an important source of interesting bioactive compounds. Aspergillus nomius NC06 was isolated from the marine sponge Neopetrosia chaliniformis. This fungus was cultured on rice medium and yielded four compounds including three new oxisterigmatocystins, namely, J, K, and L (1, 2, and 3), and one known compound, aspergillicin A (4). Structures of the compounds were elucidated by 1D and 2D NMR spectroscopy and by high-resolution mass spectrometry. The isolated compounds were tested for cytotoxic activity against HT 29 colon cancer cells, where compounds 1, 2, and 4 exhibited IC50 values of 6.28, 15.14, and 1.63 µM, respectively. Under the fluorescence microscope by using a double staining method, HT 29 cells were observed to be viable, apoptotic, and necrotic after treatment with the cytotoxic compounds 1, 2, and 4. The result shows that compounds 1 and 2 were able to induce apoptosis and cell death in HT 29 cells. Full article
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8 pages, 1419 KiB  
Article
Chemical Constituents of the Deep-Sea-Derived Penicillium solitum
by Zhi-Hui He, Jia Wu, Lin Xu, Man-Yi Hu, Ming-Ming Xie, You-Jia Hao, Shu-Jin Li, Zong-Ze Shao and Xian-Wen Yang
Mar. Drugs 2021, 19(10), 580; https://doi.org/10.3390/md19100580 - 17 Oct 2021
Cited by 8 | Viewed by 3205
Abstract
A systematic chemical investigation of the deep-sea-derived fungus Penicillium solitum MCCC 3A00215 resulted in the isolation of one novel polyketide (1), two new alkaloids (2 and 3), and 22 known (425) compounds. The structures [...] Read more.
A systematic chemical investigation of the deep-sea-derived fungus Penicillium solitum MCCC 3A00215 resulted in the isolation of one novel polyketide (1), two new alkaloids (2 and 3), and 22 known (425) compounds. The structures of the new compounds were established mainly on the basis of exhaustive analysis of 1D and 2D NMR data. Viridicatol (13) displayed moderate anti-tumor activities against PANC-1, Hela, and A549 cells with IC50 values of around 20 μM. Moreover, 13 displayed potent in vitro anti-food allergic activity with an IC50 value of 13 μM, compared to that of 92 μM for the positive control, loratadine, while indole-3-acetic acid methyl ester (9) and penicopeptide A (10) showed moderate effects (IC50 = 50 and 58 μM, respectively). Full article
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14 pages, 3159 KiB  
Article
Secondary Metabolites with α-Glucosidase Inhibitory Activity from Mangrove Endophytic Fungus Talaromyces sp. CY-3
by Wencong Yang, Qi Tan, Yihao Yin, Yan Chen, Yi Zhang, Jianying Wu, Leyao Gao, Bo Wang and Zhigang She
Mar. Drugs 2021, 19(9), 492; https://doi.org/10.3390/md19090492 - 28 Aug 2021
Cited by 10 | Viewed by 2924
Abstract
Eight new compounds, including two sambutoxin derivatives (12), two highly oxygenated cyclopentenones (78), four highly oxygenated cyclohexenones (912), together with four known sambutoxin derivatives (36), were isolated [...] Read more.
Eight new compounds, including two sambutoxin derivatives (12), two highly oxygenated cyclopentenones (78), four highly oxygenated cyclohexenones (912), together with four known sambutoxin derivatives (36), were isolated from semimangrove endophytic fungus Talaromyces sp. CY-3, under the guidance of molecular networking. The structures of new isolates were elucidated by analysis of detailed spectroscopic data, ECD spectra, chemical hydrolysis, 13C NMR calculation, and DP4+ analysis. In bioassays, compounds 15 displayed better α-glucosidase inhibitory activity than the positive control 1-deoxynojirimycin (IC50 = 80.8 ± 0.3 μM), and the IC50 value was in the range of 12.6 ± 0.9 to 57.3 ± 1.3 μM. Full article
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22 pages, 3287 KiB  
Article
Anthraquinones, Diphenyl Ethers, and Their Derivatives from the Culture of the Marine Sponge-Associated Fungus Neosartorya spinosa KUFA 1047
by Joana D. M. de Sá, José A. Pereira, Tida Dethoup, Honorina Cidade, Maria Emília Sousa, Inês C. Rodrigues, Paulo M. Costa, Sharad Mistry, Artur M. S. Silva and Anake Kijjoa
Mar. Drugs 2021, 19(8), 457; https://doi.org/10.3390/md19080457 - 11 Aug 2021
Cited by 14 | Viewed by 3287
Abstract
Previously unreported anthraquinone, acetylpenipurdin A (4), biphenyl ether, neospinosic acid (6), dibenzodioxepinone, and spinolactone (7) were isolated, together with (R)-6-hydroxymellein (1), penipurdin A (2), acetylquestinol (3), tenellic acid C [...] Read more.
Previously unreported anthraquinone, acetylpenipurdin A (4), biphenyl ether, neospinosic acid (6), dibenzodioxepinone, and spinolactone (7) were isolated, together with (R)-6-hydroxymellein (1), penipurdin A (2), acetylquestinol (3), tenellic acid C (5), and vermixocin A (8) from the culture of a marine sponge-associated fungus Neosartorya spinosa KUFA1047. The structures of the previously unreported compounds were established based on an extensive analysis of 1D and 2D NMR spectra as well as HRMS data. The absolute configurations of the stereogenic centers of 5 and 7 were established unambiguously by comparing their calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 2 and 58 were tested for their in vitro acetylcholinesterase and tyrosinase inhibitory activities as well as their antibacterial activity against Gram-positive and Gram-negative reference, and multidrug-resistant strains isolated from the environment. The tested compounds were also evaluated for their capacity to inhibit biofilm formation in the reference strains. Full article
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10 pages, 1937 KiB  
Article
Four New Chromones from the Endophytic Fungus Phomopsis asparagi DHS-48 Isolated from the Chinese Mangrove Plant Rhizophora mangle
by Chengwen Wei, Chunxiao Sun, Zhao Feng, Xuexia Zhang and Jing Xu
Mar. Drugs 2021, 19(6), 348; https://doi.org/10.3390/md19060348 - 19 Jun 2021
Cited by 12 | Viewed by 2353
Abstract
Four new chromones, phomochromenones D–G (14), along with four known analogues, diaporchromone A (5), diaporchromanone C (6), diaporchromanone D (7), and phomochromenone C (8), were isolated from the culture of Phomopsis [...] Read more.
Four new chromones, phomochromenones D–G (14), along with four known analogues, diaporchromone A (5), diaporchromanone C (6), diaporchromanone D (7), and phomochromenone C (8), were isolated from the culture of Phomopsis asparagi DHS-48 from Chinese mangrove Rhizophora mangle. Their structures were elucidated on the basis of comprehensive spectroscopic analysis. The absolute configurations of 1 and 4 were assigned on the basis of experimental and calculated electronic circular dichroism (ECD) data, and those of enantiomers 2 and 3 were determined by a modified Mosher’s method and basic hydrolysis. To the best of our knowledge, phomochromenones D–F (14) possessing a 3-substituted-chroman-4-one skeleton are rarely found in natural sources. Diaporchromone A (5) showed moderate to weak immunosuppressive activity against T and/or B lymphocyte cells with IC50 of 34 μM and 117 μM. Full article
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9 pages, 2271 KiB  
Article
Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete Aspergillus oryzae
by Raha Orfali, Shagufta Perveen, Muhammad Farooq Khan, Atallah F. Ahmed, Mohammad A. Wadaan, Areej Mohammad Al-Taweel, Ali S. Alqahtani, Fahd A. Nasr, Sobia Tabassum, Paolo Luciano, Giuseppina Chianese, Jyh-Horng Sheu and Orazio Taglialatela-Scafati
Mar. Drugs 2021, 19(6), 333; https://doi.org/10.3390/md19060333 - 10 Jun 2021
Cited by 8 | Viewed by 3117
Abstract
The new asperorlactone (1), along with the known illudalane sesquiterpene echinolactone D (2), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (3) and its acetate 4, and 4-hydroxybenzaldehyde (5), were isolated from a culture of Aspergillus [...] Read more.
The new asperorlactone (1), along with the known illudalane sesquiterpene echinolactone D (2), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (3) and its acetate 4, and 4-hydroxybenzaldehyde (5), were isolated from a culture of Aspergillus oryzae, collected from Red Sea marine sediments. The structure of asperorlactone (1) was elucidated by HR-ESIMS, 1D, and 2D NMR, and a comparison between experimental and DFT calculated electronic circular dichroism (ECD) spectra. This is the first report of illudalane sesquiterpenoids from Aspergillus fungi and, more in general, from ascomycetes. Asperorlactone (1) exhibited antiproliferative activity against human lung, liver, and breast carcinoma cell lines, with IC50 values < 100 µM. All the isolated compounds were also evaluated for their toxicity using the zebrafish embryo model. Full article
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13 pages, 1975 KiB  
Article
Characteristic Volatile Composition of Seven Seaweeds from the Yellow Sea of China
by Pengrui Wang, Jiapeng Chen, Lujing Chen, Li Shi and Hongbing Liu
Mar. Drugs 2021, 19(4), 192; https://doi.org/10.3390/md19040192 - 29 Mar 2021
Cited by 12 | Viewed by 3088
Abstract
Plant volatile organic compounds (VOCs) represent a relatively wide class of secondary metabolites. The VOC profiles of seven seaweeds (Grateloupia filicina, Polysiphonia senticulosa, Callithamnion corymbosum, Sargassum thunbergii, Dictyota dichotoma, Enteromorpha prolifera and Ulva lactuca) from the [...] Read more.
Plant volatile organic compounds (VOCs) represent a relatively wide class of secondary metabolites. The VOC profiles of seven seaweeds (Grateloupia filicina, Polysiphonia senticulosa, Callithamnion corymbosum, Sargassum thunbergii, Dictyota dichotoma, Enteromorpha prolifera and Ulva lactuca) from the Yellow Sea of China were investigated using multifiber headspace solid phase microextraction coupled with gas chromatography–mass spectrometry (HS-SPME/GC–MS), among them, the VOCs of three red algae Grateloupia filicina, Polysiphonia senticulosa, and Callithamnion corymbosum were first reported. Principal component analysis (PCA) was used to disclose characteristic categories and molecules of VOCs and network pharmacology was performed to predict potential biomedical utilization of candidate seaweeds. Aldehyde was found to be the most abundant VOC category in the present study and (E)-β-ionone was the only compound found to exist in all seven seaweeds. The chemical diversity of aldehydes in E. prolifera suggest its potential application in chemotaxonomy and hinted that divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) fiber is more suitable for aldehyde extraction. VOCs in D. dichotoma were characterized as sesquiterpenes and diterpenes and the most relevant pharmacological pathway was the neuroactive ligand–receptor interaction pathway, which suggests that D. dichotoma may have certain preventive and therapeutic values in cancer, especially in lung cancer, in addition to neuropsychiatric diseases. Full article
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10 pages, 2620 KiB  
Article
Metabolites with Anti-Inflammatory Activity from the Mangrove Endophytic Fungus Diaporthe sp. QYM12
by Yan Chen, Ge Zou, Wencong Yang, Yingying Zhao, Qi Tan, Lin Chen, Jinmei Wang, Changyang Ma, Wenyi Kang and Zhigang She
Mar. Drugs 2021, 19(2), 56; https://doi.org/10.3390/md19020056 - 24 Jan 2021
Cited by 25 | Viewed by 3046
Abstract
One new diterpenoid, diaporpenoid A (1), two new sesquiterpenoids, diaporpenoids B–C (2,3) and three new α-pyrone derivatives, diaporpyrones A–C (46) were isolated from an MeOH extract obtained from cultures of the mangrove [...] Read more.
One new diterpenoid, diaporpenoid A (1), two new sesquiterpenoids, diaporpenoids B–C (2,3) and three new α-pyrone derivatives, diaporpyrones A–C (46) were isolated from an MeOH extract obtained from cultures of the mangrove endophytic fungus Diaporthe sp. QYM12. Their structures were elucidated by extensive analysis of spectroscopic data. The absolute configurations were determined by electronic circular dichroism (ECD) calculations and a comparison of the specific rotation. Compound 1 had an unusual 5/10/5-fused tricyclic ring system. Compounds 1 and 4 showed potent anti-inflammatory activities by inhibiting the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW264.7 cells with IC50 values of 21.5 and 12.5 μM, respectively. Full article
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18 pages, 2190 KiB  
Article
Preparation, COX-2 Inhibition and Anticancer Activity of Sclerotiorin Derivatives
by Tao Chen, Yun Huang, Junxian Hong, Xikang Wei, Fang Zeng, Jialin Li, Geting Ye, Jie Yuan and Yuhua Long
Mar. Drugs 2021, 19(1), 12; https://doi.org/10.3390/md19010012 - 29 Dec 2020
Cited by 12 | Viewed by 3135
Abstract
The latest research has indicated that anti-tumor agents with COX-2 inhibitory activity may benefit their anti-tumor efficiency. A series of sclerotiorin derivatives have been synthesized and screened for their cytotoxic activity against human lung cancer cells A549, breast cancer cells MDA-MB-435 using the [...] Read more.
The latest research has indicated that anti-tumor agents with COX-2 inhibitory activity may benefit their anti-tumor efficiency. A series of sclerotiorin derivatives have been synthesized and screened for their cytotoxic activity against human lung cancer cells A549, breast cancer cells MDA-MB-435 using the MTT method. Among them, compounds 3, 7, 12, 13, 15, 17 showed good cytotoxic activity with IC50 values of 6.39, 9.20, 9.76, 7.75, 9.08, and 8.18 μM, respectively. In addition, all compounds were tested in vitro the COX-2 inhibitory activity. The results disclosed compounds 7, 13, 25 and sclerotiorin showed moderate to good COX-2 inhibition with the inhibitory ratios of 58.7%, 51.1%, 66.1% and 56.1%, respectively. Notably, compound 3 displayed a comparable inhibition ratio (70.6%) to the positive control indomethacin (78.9%). Furthermore, molecular docking was used to rationalize the potential of the sclerotiorin derivatives as COX2 inhibitory agents by predicting their binding energy, binding modes and optimal orientation at the active site of the COX-2. Additionally, the structure-activity relationships (SARS) have been addressed. Full article
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10 pages, 1229 KiB  
Article
Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum
by Ya-Ping Liu, Sheng-Tao Fang, Zhen-Zhen Shi, Bin-Gui Wang, Xiao-Nian Li and Nai-Yun Ji
Mar. Drugs 2021, 19(1), 9; https://doi.org/10.3390/md19010009 - 28 Dec 2020
Cited by 23 | Viewed by 3257
Abstract
Three new phenylhydrazones, penoxahydrazones A–C (compounds 13), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures [...] Read more.
Three new phenylhydrazones, penoxahydrazones A–C (compounds 13), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria. Full article
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11 pages, 1722 KiB  
Article
Antimicrobial and Antioxidant Polyketides from a Deep-Sea-Derived Fungus Aspergillus versicolor SH0105
by Lu-Jia Yang, Xiao-Yue Peng, Ya-Hui Zhang, Zhi-Qing Liu, Xin Li, Yu-Cheng Gu, Chang-Lun Shao, Zhuang Han and Chang-Yun Wang
Mar. Drugs 2020, 18(12), 636; https://doi.org/10.3390/md18120636 - 11 Dec 2020
Cited by 22 | Viewed by 3251
Abstract
Fifteen polyketides, including four new compounds, isoversiol F (1), decumbenone D (2), palitantin B (7), and 1,3-di-O-methyl-norsolorinic acid (8), along with 11 known compounds (36 and 915), [...] Read more.
Fifteen polyketides, including four new compounds, isoversiol F (1), decumbenone D (2), palitantin B (7), and 1,3-di-O-methyl-norsolorinic acid (8), along with 11 known compounds (36 and 915), were isolated from the deep-sea-derived fungus Aspergillus versicolor SH0105. Their structures and absolute configurations were determined by comprehensive spectroscopic data, including 1D and 2D NMR, HRESIMS, and ECD calculations, and it is the first time to determine the absolute configuration of known decumbenone A (6). All of these compounds were evaluated for their antimicrobial activities against four human pathogenic microbes and five fouling bacterial strains. The results indicated that 3,7-dihydroxy-1,9-dimethyldibenzofuran (14) displayed obvious inhibitory activity against Staphylococcus aureus (ATCC 27154) with the MIC value of 13.7 μM. In addition, the antioxidant assays of the isolated compounds revealed that aspermutarubrol/violaceol-I (15) exhibited significant 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity with the IC50 value of 34.1 μM, and displayed strong reduction of Fe3+ with the ferric reducing antioxidant power (FRAP) value of 9.0 mM under the concentration of 3.1 μg/mL, which were more potent than ascorbic acid. Full article
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8 pages, 1507 KiB  
Article
Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus Penicillium cyclopium SD-413
by Yan-He Li, Xiao-Ming Li, Xin Li, Sui-Qun Yang, Xiao-Shan Shi, Hong-Lei Li and Bin-Gui Wang
Mar. Drugs 2020, 18(11), 553; https://doi.org/10.3390/md18110553 - 6 Nov 2020
Cited by 21 | Viewed by 2702
Abstract
Nine secondary metabolites (19), including two new polyketide derivatives 9-dehydroxysargassopenilline A (4) and 1,2-didehydropeaurantiogriseol E (5), along with seven known related secondary metabolites (13 and 69), were isolated and [...] Read more.
Nine secondary metabolites (19), including two new polyketide derivatives 9-dehydroxysargassopenilline A (4) and 1,2-didehydropeaurantiogriseol E (5), along with seven known related secondary metabolites (13 and 69), were isolated and identified from the deep sea-derived fungus Penicilliumcyclopium SD-413. Their structures were elucidated on the basis of 1D/2D NMR spectroscopic and mass spectrometric analysis and the absolute configurations were determined by the combination of NOESY correlations and time-dependent density functional (TDDFT) ECD calculations. Compounds 19 inhibited some pathogenic bacteria including Escherichia coli, E. ictaluri, Edwardsiella tarda, Micrococcus luteus, Vibrio anguillarum, and V. harveyi, with MIC (minimum inhibitory concentration) values ranging from 4 to 32 μg/mL. Full article
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10 pages, 2081 KiB  
Article
Lipopeptide Epimers and a Phthalide Glycerol Ether with AChE Inhibitory Activities from the Marine-Derived Fungus Cochliobolus Lunatus SCSIO41401
by Yu Dai, Kunlong Li, Jianglian She, Yanbo Zeng, Hao Wang, Shengrong Liao, Xiuping Lin, Bin Yang, Junfeng Wang, Huaming Tao, Haofu Dai, Xuefeng Zhou and Yonghong Liu
Mar. Drugs 2020, 18(11), 547; https://doi.org/10.3390/md18110547 - 30 Oct 2020
Cited by 15 | Viewed by 2364
Abstract
A pair of novel lipopeptide epimers, sinulariapeptides A (1) and B (2), and a new phthalide glycerol ether (3) were isolated from the marine algal-associated fungus Cochliobolus lunatus SCSIO41401, together with three known chromanone derivates (4 [...] Read more.
A pair of novel lipopeptide epimers, sinulariapeptides A (1) and B (2), and a new phthalide glycerol ether (3) were isolated from the marine algal-associated fungus Cochliobolus lunatus SCSIO41401, together with three known chromanone derivates (46). The structures of the new compounds, including the absolute configurations, were determined by comprehensive spectroscopic methods, experimental and calculated electronic circular dichroism (ECD), and Mo2 (OAc)4-induced ECD methods. The new compounds 13 showed moderate inhibitory activity against acetylcholinesterase (AChE), with IC50 values of 1.3–2.5 μM, and an in silico molecular docking study was also performed. Full article
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Review

Jump to: Editorial, Research

24 pages, 2206 KiB  
Review
Impact of Co-Culture on the Metabolism of Marine Microorganisms
by Flore Caudal, Nathalie Tapissier-Bontemps and Ru Angelie Edrada-Ebel
Mar. Drugs 2022, 20(2), 153; https://doi.org/10.3390/md20020153 - 21 Feb 2022
Cited by 18 | Viewed by 4624
Abstract
Natural products from plants have been listed for hundreds of years as a source of biologically active molecules. In recent years, the marine environment has demonstrated its ability to provide new structural entities. More than 70% of our planet’s surface is covered by [...] Read more.
Natural products from plants have been listed for hundreds of years as a source of biologically active molecules. In recent years, the marine environment has demonstrated its ability to provide new structural entities. More than 70% of our planet’s surface is covered by oceans, and with the technical advances in diving and remotely operated vehicles, it is becoming easier to collect samples. Although the risk of rediscovery is significant, the discovery of silent gene clusters and innovative analytical techniques has renewed interest in natural product research. Different strategies have been proposed to activate these silent genes, including co-culture, or mixed fermentation, a cultivation-based approach. This review highlights the potential of co-culture of marine microorganisms to induce the production of new metabolites as well as to increase the yields of respective target metabolites with pharmacological potential, and moreover to indirectly improve the biological activity of a crude extract. Full article
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13 pages, 319 KiB  
Review
Marine Microbial Fibrinolytic Enzymes: An Overview of Source, Production, Biochemical Properties and Thrombolytic Activity
by Noora Barzkar, Saeid Tamadoni Jahromi and Fabio Vianello
Mar. Drugs 2022, 20(1), 46; https://doi.org/10.3390/md20010046 - 2 Jan 2022
Cited by 30 | Viewed by 3695
Abstract
Cardiovascular diseases (CVDs) have emerged as a major threat to global health resulting in a decrease in life expectancy with respect to humans. Thrombosis is one of the foremost causes of CVDs, and it is characterized by the unwanted formation of fibrin clots. [...] Read more.
Cardiovascular diseases (CVDs) have emerged as a major threat to global health resulting in a decrease in life expectancy with respect to humans. Thrombosis is one of the foremost causes of CVDs, and it is characterized by the unwanted formation of fibrin clots. Recently, microbial fibrinolytic enzymes due to their specific features have gained much more attention than conventional thrombolytic agents for the treatment of thrombosis. Marine microorganisms including bacteria and microalgae have the significant ability to produce fibrinolytic enzymes with improved pharmacological properties and lesser side effects and, hence, are considered as prospective candidates for large scale production of these enzymes. There are no studies that have evaluated the fibrinolytic potential of marine fungal-derived enzymes. The current review presents an outline regarding isolation sources, production, features, and thrombolytic potential of fibrinolytic biocatalysts from marine microorganisms identified so far. Full article
19 pages, 2726 KiB  
Review
Marine Power on Cancer: Drugs, Lead Compounds, and Mechanisms
by Lichuan Wu, Ke Ye, Sheng Jiang and Guangbiao Zhou
Mar. Drugs 2021, 19(9), 488; https://doi.org/10.3390/md19090488 - 27 Aug 2021
Cited by 18 | Viewed by 5232
Abstract
Worldwide, 19.3 million new cancer cases and almost 10.0 million cancer deaths occur each year. Recently, much attention has been paid to the ocean, the largest biosphere of the earth that harbors a great many different organisms and natural products, to identify novel [...] Read more.
Worldwide, 19.3 million new cancer cases and almost 10.0 million cancer deaths occur each year. Recently, much attention has been paid to the ocean, the largest biosphere of the earth that harbors a great many different organisms and natural products, to identify novel drugs and drug candidates to fight against malignant neoplasms. The marine compounds show potent anticancer activity in vitro and in vivo, and relatively few drugs have been approved by the U.S. Food and Drug Administration for the treatment of metastatic malignant lymphoma, breast cancer, or Hodgkin′s disease. This review provides a summary of the anticancer effects and mechanisms of action of selected marine compounds, including cytarabine, eribulin, marizomib, plitidepsin, trabectedin, zalypsis, adcetris, and OKI-179. The future development of anticancer marine drugs requires innovative biochemical biology approaches and introduction of novel therapeutic targets, as well as efficient isolation and synthesis of marine-derived natural compounds and derivatives. Full article
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35 pages, 10358 KiB  
Review
Structures and Biological Activities of Diketopiperazines from Marine Organisms: A Review
by Zhiqiang Song, Yage Hou, Qingrong Yang, Xinpeng Li and Shaohua Wu
Mar. Drugs 2021, 19(8), 403; https://doi.org/10.3390/md19080403 - 21 Jul 2021
Cited by 41 | Viewed by 4875
Abstract
Diketopiperazines are potential structures with extensive biological functions, which have attracted much attention of natural product researchers for a long time. These compounds possess a stable six-membered ring, which is an important pharmacophore. The marine organisms have especially been proven to be a [...] Read more.
Diketopiperazines are potential structures with extensive biological functions, which have attracted much attention of natural product researchers for a long time. These compounds possess a stable six-membered ring, which is an important pharmacophore. The marine organisms have especially been proven to be a wide source for discovering diketopiperazine derivatives. In recent years, more and more interesting bioactive diketopiperazines had been found from various marine habitats. This review article is focused on the new 2,5-diketopiperazines derived from marine organisms (sponges and microorganisms) reported from the secondary half-year of 2014 to the first half of the year of 2021. We will comment their chemical structures, biological activities and sources. The objective is to assess the merit of these compounds for further study in the field of drug discovery. Full article
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15 pages, 5505 KiB  
Review
Marine Polysaccharides as a Versatile Biomass for the Construction of Nano Drug Delivery Systems
by Ying Sun, Xiaoli Ma and Hao Hu
Mar. Drugs 2021, 19(6), 345; https://doi.org/10.3390/md19060345 - 16 Jun 2021
Cited by 59 | Viewed by 6350
Abstract
Marine biomass is a treasure trove of materials. Marine polysaccharides have the characteristics of biocompatibility, biodegradability, non-toxicity, low cost, and abundance. An enormous variety of polysaccharides can be extracted from marine organisms such as algae, crustaceans, and microorganisms. The most studied marine polysaccharides [...] Read more.
Marine biomass is a treasure trove of materials. Marine polysaccharides have the characteristics of biocompatibility, biodegradability, non-toxicity, low cost, and abundance. An enormous variety of polysaccharides can be extracted from marine organisms such as algae, crustaceans, and microorganisms. The most studied marine polysaccharides include chitin, chitosan, alginates, hyaluronic acid, fucoidan, carrageenan, agarose, and Ulva. Marine polysaccharides have a wide range of applications in the field of biomedical materials, such as drug delivery, tissue engineering, wound dressings, and sensors. The drug delivery system (DDS) can comprehensively control the distribution of drugs in the organism in space, time, and dosage, thereby increasing the utilization efficiency of drugs, reducing costs, and reducing toxic side effects. The nano-drug delivery system (NDDS), due to its small size, can function at the subcellular level in vivo. The marine polysaccharide-based DDS combines the advantages of polysaccharide materials and nanotechnology, and is suitable as a carrier for different pharmaceutical preparations. This review summarizes the advantages and drawbacks of using marine polysaccharides to construct the NDDS and describes the preparation methods and modification strategies of marine polysaccharide-based nanocarriers. Full article
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26 pages, 5302 KiB  
Review
Progress in Research on Bioactive Secondary Metabolites from Deep-Sea Derived Microorganisms
by Ya-Nan Wang, Ling-Hong Meng and Bin-Gui Wang
Mar. Drugs 2020, 18(12), 614; https://doi.org/10.3390/md18120614 - 2 Dec 2020
Cited by 48 | Viewed by 5330
Abstract
Deep sea has an extreme environment which leads to biodiversity of microorganisms and their unique physical and biochemical mechanisms. Deep-sea derived microorganisms are more likely to produce novel bioactive substances with special mechanism of action for drug discovery. This article reviews secondary metabolites [...] Read more.
Deep sea has an extreme environment which leads to biodiversity of microorganisms and their unique physical and biochemical mechanisms. Deep-sea derived microorganisms are more likely to produce novel bioactive substances with special mechanism of action for drug discovery. This article reviews secondary metabolites with biological activities such as anti-tumor, anti-bacterial, anti-viral, and anti-inflammatory isolated from deep-sea fungi and bacteria during 2018–2020. Effective methods for screening and obtaining natural active compounds from deep-sea microorganisms are also summarized, including optimizing the culture conditions, using genome mining technology, biosynthesis and so on. The comprehensive application of these methods makes broader prospects for the development and application of deep sea microbial bioactive substances. Full article
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