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11 pages, 1295 KiB

Open AccessArticle

2-Alkyl-4-hydroxyquinolines from a Marine-Derived Streptomyces sp. Inhibit Hyphal Growth Induction in Candida albicans

by Heegyu Kim, Ji-Yeon Hwang, Beomkoo Chung, Eunji Cho, Suhyun Bae, Jongheon Shin and Ki-Bong Oh

Mar. Drugs 2019, 17(2), 133; https://doi.org/10.3390/md17020133 - 22 Feb 2019

Cited by 13 | Viewed by 3145

Abstract

Four 2-alkyl-4-hydroxyquinoline derivatives (1–4) were isolated from a semisolid rice culture of the marine-derived actinomycete Streptomyces sp. MBTG13. The structures of these compounds were elucidated by a combination of spectroscopic methods, and their data were in good agreement with [...] Read more.

Four 2-alkyl-4-hydroxyquinoline derivatives (1–4) were isolated from a semisolid rice culture of the marine-derived actinomycete Streptomyces sp. MBTG13. The structures of these compounds were elucidated by a combination of spectroscopic methods, and their data were in good agreement with previous reports. Compounds 1 and 2 exhibited weak to moderate antibacterial activity against pathogenic bacteria. Unexpectedly, we found that compound 1 acted as a potent inhibitor of hyphal growth induction in the dimorphic fungus Candida albicans, with an IC₅₀ value of 11.4 μg/mL. Growth experiments showed that this compound did not inhibit yeast cell growth, but inhibited hyphal growth induction. Semi-quantitative reverse transcription (RT)-PCR analysis of hyphal-inducing signaling pathway components indicated that compound 1 inhibited the expression of mRNAs related to the cAMP-Efg1 pathway. The expression of HWP1 and ALS3 mRNAs (hypha-specific genes positively regulated by Efg1, an important regulator of cell wall dynamics) was significantly inhibited by the addition of compound 1. These results indicate that compound 1 acts on the Efg1-mediated cAMP pathway and regulates hyphal growth in Candida albicans. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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17 pages, 1928 KiB

Open AccessArticle

Biosynthesis of Nutraceutical Fatty Acids by the Oleaginous Marine Microalgae Phaeodactylum tricornutum Utilizing Hydrolysates from Organosolv-Pretreated Birch and Spruce Biomass

by Alok Patel, Leonidas Matsakas, Kateřina Hrůzová, Ulrika Rova and Paul Christakopoulos

Mar. Drugs 2019, 17(2), 119; https://doi.org/10.3390/md17020119 - 15 Feb 2019

Cited by 53 | Viewed by 3822

Abstract

Polyunsaturated fatty acids (PUFAs) are essential for human function, however they have to be provided through the diet. As their production from fish oil is environmentally unsustainable, there is demand for new sources of PUFAs. The aim of the present work was to [...] Read more.

Polyunsaturated fatty acids (PUFAs) are essential for human function, however they have to be provided through the diet. As their production from fish oil is environmentally unsustainable, there is demand for new sources of PUFAs. The aim of the present work was to establish the microalgal platform to produce nutraceutical-value PUFAs from forest biomass. To this end, the growth of Phaeodactylum tricornutum on birch and spruce hydrolysates was compared to autotrophic cultivation and glucose synthetic media. Total lipid generated by P. tricornutum grown mixotrophically on glucose, birch, and spruce hydrolysates was 1.21, 1.26, and 1.29 g/L, respectively. The highest eicosapentaenoic acid (EPA) production (256 mg/L) and productivity (19.69 mg/L/d) were observed on spruce hydrolysates. These values were considerably higher than those obtained from the cultivation without glucose (79.80 mg/L and 6.14 mg/L/d, respectively) and also from the photoautotrophic cultivation (26.86 mg/L and 2.44 mg/L/d, respectively). To the best of our knowledge, this is the first report describing the use of forest biomass as raw material for EPA and docosapentaenoic acid (DHA) production. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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15 pages, 4299 KiB

Open AccessArticle

Marine Bacterial Polysaccharide EPS11 Inhibits Cancer Cell Growth and Metastasis via Blocking Cell Adhesion and Attenuating Filiform Structure Formation

by Ju Wang, Ge Liu, Weiping Ma, Zhongxia Lu and Chaomin Sun

Mar. Drugs 2019, 17(1), 50; https://doi.org/10.3390/md17010050 - 11 Jan 2019

Cited by 19 | Viewed by 3595

Abstract

Our previous results suggested that EPS11, a novel marine bacterial polysaccharide, might be a potential drug candidate for human non-small cell lung carcinoma treatment. In this study, we further investigate the anticancer mechanisms against liver cancer and the anti-metastatic effects in vivo of [...] Read more.

Our previous results suggested that EPS11, a novel marine bacterial polysaccharide, might be a potential drug candidate for human non-small cell lung carcinoma treatment. In this study, we further investigate the anticancer mechanisms against liver cancer and the anti-metastatic effects in vivo of EPS11. Firstly, we found that EPS11 exerts cytotoxic effects via blocking cell adhesion and destroying filiform structure formation in Huh7.5 cells. Moreover, mass spectrometry-based proteomic analysis of EPS11-treated Huh7.5 cells revealed that expression of many adhesion-related proteins was significantly changed. It is noteworthy that the expression of CD99, a key factor related to cell adhesion, migration and cell death, is remarkably down-regulated after EPS11 treatment. Importantly, over-expression of CD99 partly rescues cell death rate, and improves cell adhesion and migration ability in Huh7.5 treated by EPS11. Thus, we propose that CD99 is a potential action target of EPS11, inhibiting cancer cell proliferation, adhesion and migration. Notably, administration of EPS11 simultaneously with tumor induction evidently reduces tumor nodule formation in the lungs, which strongly indicates that EPS11 has anti-metastatic effects in vivo. Taken together, our results suggest that EPS11 inhibits liver cancer cell growth via blocking cell adhesion and attenuating filiform structure formation, and has potential as an anti-cancer drug, targeting metastasis of cancer cells, in the future. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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9 pages, 2082 KiB

Open AccessArticle

Citrinin Monomer and Dimer Derivatives with Antibacterial and Cytotoxic Activities Isolated from the Deep Sea-Derived Fungus Penicillium citrinum NLG-S01-P1

by Weiyi Wang, Yanyan Liao, Beibei Zhang, Maolin Gao, Wenqian Ke, Fang Li and Zongze Shao

Mar. Drugs 2019, 17(1), 46; https://doi.org/10.3390/md17010046 - 10 Jan 2019

Cited by 35 | Viewed by 4308

Abstract

Two previously unreported citrinin dimer derivatives, penicitol D (1) and 1-epi-citrinin H1 (2), were isolated from the culture of a deep sea-derived fungus Penicillium citrinum NLG-S01-P1, together with 11 biogenetic related compounds (3–13). [...] Read more.

Two previously unreported citrinin dimer derivatives, penicitol D (1) and 1-epi-citrinin H1 (2), were isolated from the culture of a deep sea-derived fungus Penicillium citrinum NLG-S01-P1, together with 11 biogenetic related compounds (3–13). A plausible biogenetic pathway for compounds 2–4 was proposed. Their structures, including absolute configurations, were established through analysis of extensive spectroscopic data and time-dependent density functional theory (TD-DFT) ECD calculations. Compounds 1 and 2 showed antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA). Compounds 5 and 10 displayed relatively stronger activities than the other compounds against Vibrio vulnificus and Vibrio campbellii. Compound 1 showed the most potent cytotoxic activity towards the HeLa cell. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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9 pages, 3754 KiB

Open AccessArticle

Two New Diketomorpholine Derivatives and a New Highly Conjugated Ergostane-Type Steroid from the Marine Algal-Derived Endophytic Fungus Aspergillus alabamensis EN-547

by Sui-Qun Yang, Xiao-Ming Li, Xin Li, Lu-Ping Chi and Bin-Gui Wang

Mar. Drugs 2018, 16(4), 114; https://doi.org/10.3390/md16040114 - 31 Mar 2018

Cited by 18 | Viewed by 4288

Abstract

Chemical investigation of the marine algal-derived endophytic fungus Aspergillus alabamensis EN-547 resulted in the isolation of 4-epi-seco-shornephine A methyl ester (1) and 4-epi-seco-shornephine A carboxylic acid (2), two new secondary metabolites [...] Read more.

Chemical investigation of the marine algal-derived endophytic fungus Aspergillus alabamensis EN-547 resulted in the isolation of 4-epi-seco-shornephine A methyl ester (1) and 4-epi-seco-shornephine A carboxylic acid (2), two new secondary metabolites having a rare diketomorpholine motif, and 28-acetoxy-12β,15α,25-trihydroxyergosta-4,6,8(14),22-tetraen-3-one (3), a new highly conjugated ergostane-type steroid, together with four known metabolites (4–7). Their chemical structures were elucidated by detailed analysis of their NMR spectra, ECDs, HRESIMS, optical rotation, and X-ray crystallographic data, and by comparison with literature data as well. The antimicrobial activities of compounds 1–7 were evaluated. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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11 pages, 2383 KiB

Open AccessArticle

Chlorinated Azaphilone Pigments with Antimicrobial and Cytotoxic Activities Isolated from the Deep Sea Derived Fungus Chaetomium sp. NA-S01-R1

by Weiyi Wang, Yanyan Liao, Ruixuan Chen, Yanping Hou, Wenqian Ke, Beibei Zhang, Maolin Gao, Zongze Shao, Jianming Chen and Fang Li

Mar. Drugs 2018, 16(2), 61; https://doi.org/10.3390/md16020061 - 13 Feb 2018

Cited by 58 | Viewed by 4642

Abstract

Four novel compounds, chaephilone C (1), chaetoviridides A–C (2–4), were obtained from the culture of a deep sea derived fungus Chaetomium sp. NA-S01-R1, together with four known compounds—chaetoviridin A (5), chaetoviridine E (6), [...] Read more.

Four novel compounds, chaephilone C (1), chaetoviridides A–C (2–4), were obtained from the culture of a deep sea derived fungus Chaetomium sp. NA-S01-R1, together with four known compounds—chaetoviridin A (5), chaetoviridine E (6), chaetomugilin D (7) and cochliodone A (8). Their structures, including absolute configurations, were assigned based on NMR, MS and time-dependent density functional theory (TD-DFT) ECD calculations. A plausible biogenetic pathway for compounds 1–3 was proposed. Compounds 2 and 3 exhibited antibacterial activities against Vibrio rotiferianus and Vibrio vulnificus. Compounds 1, 3 and 4 displayed similar anti-methicillin resistant Staphylococcus aureus (anti-MRSA) activities in comparison to chloramphenicol. Compound 2 showed the most potent cytotoxic activities towards the Hep G2 cell and compounds 1 and 3 demonstrated relatively stronger cytotoxic activities than the other compounds against the HeLa cell. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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15 pages, 1816 KiB

Open AccessArticle

Anti-Phytopathogenic and Cytotoxic Activities of Crude Extracts and Secondary Metabolites of Marine-Derived Fungi

by Dong-Lin Zhao, Dan Wang, Xue-Ying Tian, Fei Cao, Yi-Qiang Li and Cheng-Sheng Zhang

Mar. Drugs 2018, 16(1), 36; https://doi.org/10.3390/md16010036 - 18 Jan 2018

Cited by 39 | Viewed by 6776

Abstract

Thirty-one isolates belonging to eight genera in seven orders were identified from 141 strains that were isolated from several marine plants. Alternaria sp. and Fusarium sp. were found to be the predominant fungi. Evaluation of the anti-phytopathogenic bacterial and fungal activities, as well [...] Read more.

Thirty-one isolates belonging to eight genera in seven orders were identified from 141 strains that were isolated from several marine plants. Alternaria sp. and Fusarium sp. were found to be the predominant fungi. Evaluation of the anti-phytopathogenic bacterial and fungal activities, as well as the cytotoxicity of these 31 extracts, revealed that most of them displayed different levels of bioactivities. Due to their interesting bioactivities, two fungal strains—Fusarium equiseti (P18) and Alternaria sp. (P8)—were selected for chemical investigation and compounds 1–4 were obtained. The structure of 1 was elucidated by 1D and 2D NMR analysis, as well as high-resolution electrospray ionization mass spectroscopy (HRESIMS), and the absolute configuration of its stereogenic carbon (C-11) was established by comparison of the experimental and calculated electronic circular-dichroism (ECD) spectra. Moreover, alterperylenol (4) exhibited antibacterial activity against Clavibacter michiganensis with a minimum inhibitory concentration (MIC) of 1.95 μg/mL, which was 2-fold stronger than that of streptomycin sulfate. Additionally, an antibacterial mechanism study revealed that 4 caused membrane hyperpolarization without evidence of destruction of cell membrane integrity. Furthermore, stemphyperylenol (3) displayed potent antifungal activity against Pestallozzia theae and Alternaria brassicicola with MIC values equal to those of carbendazim. The cytotoxicity of 1 and 2 against human lung carcinoma (A-549), human cervical carcinoma (HeLa), and human hepatoma (HepG2) cell lines were also evaluated. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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6173 KiB

Open AccessArticle

α-Glucosidase and Protein Tyrosine Phosphatase 1B Inhibitory Activity of Plastoquinones from Marine Brown Alga Sargassum serratifolium

by Md. Yousof Ali, Da Hye Kim, Su Hui Seong, Hyeung-Rak Kim, Hyun Ah Jung and Jae Sue Choi

Mar. Drugs 2017, 15(12), 368; https://doi.org/10.3390/md15120368 - 01 Dec 2017

Cited by 57 | Viewed by 6574

Abstract

Sargassum serratifolium C. Agardh (Phaeophyceae, Fucales) is a marine brown alga that belongs to the family Sargassaceae. It is widely distributed throughout coastal areas of Korea and Japan. S. serratifolium has been found to contain high concentrations of plastoquinones, which have strong anti-cancer, [...] Read more.

Sargassum serratifolium C. Agardh (Phaeophyceae, Fucales) is a marine brown alga that belongs to the family Sargassaceae. It is widely distributed throughout coastal areas of Korea and Japan. S. serratifolium has been found to contain high concentrations of plastoquinones, which have strong anti-cancer, anti-inflammatory, antioxidant, and neuroprotective activity. This study aims to investigate the anti-diabetic activity of S. serratifolium and its major constituents through inhibition of protein tyrosine phosphatase 1B (PTP1B), α-glucosidase, and ONOO⁻-mediated albumin nitration. S. serratifolium ethanolic extract and fractions exhibited broad PTP1B and α-glucosidase inhibitory activity (IC₅₀, 1.83~7.04 and 3.16~24.16 µg/mL for PTP1B and α-glucosidase, respectively). In an attempt to identify bioactive compounds, three plastoquinones (sargahydroquinoic acid, sargachromenol and sargaquinoic acid) were isolated from the active n-hexane fraction of S. serratifolium. All three plastoquinones exhibited dose-dependent inhibitory activity against PTP1B in the IC₅₀ range of 5.14–14.15 µM, while sargachromenol and sargaquinoic acid showed dose-dependent inhibitory activity against α-glucosidase (IC₅₀ 42.41 ± 3.09 and 96.17 ± 3.48 µM, respectively). In the kinetic study of PTP1B enzyme inhibition, sargahydroquinoic acid and sargaquinoic acid led to mixed-type inhibition, whereas sargachromenol displayed noncompetitive-type inhibition. Moreover, plastoquinones dose-dependently inhibited ONOO⁻-mediated albumin nitration. Docking simulations of these plastoquinones demonstrated negative binding energies and close proximity to residues in the binding pocket of PTP1B and α-glucosidase, indicating that these plastoquinones have high affinity and tight binding capacity towards the active site of the enzymes. These results demonstrate that S. serratifolium and its major plastoquinones may have the potential as functional food ingredients for the prevention and treatment of type 2 diabetes. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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2734 KiB

Open AccessArticle

Lactones from the Sponge-Derived Fungus Talaromyces rugulosus

by Lisa Küppers, Weaam Ebrahim, Mona El-Neketi, Ferhat C. Özkaya, Attila Mándi, Tibor Kurtán, Raha S. Orfali, Werner E. G. Müller, Rudolf Hartmann, Wenhan Lin, Weiguo Song, Zhen Liu and Peter Proksch

Mar. Drugs 2017, 15(11), 359; https://doi.org/10.3390/md15110359 - 14 Nov 2017

Cited by 31 | Viewed by 6058

Abstract

The marine-derived fungus Talaromyces rugulosus isolated from the Mediterranean sponge Axinella cannabina and cultured on solid rice medium yielded seventeen lactone derivatives including five butenolides (1–5), seven (3S)-resorcylide derivatives (6–12), two butenolide-resorcylide dimers [...] Read more.

The marine-derived fungus Talaromyces rugulosus isolated from the Mediterranean sponge Axinella cannabina and cultured on solid rice medium yielded seventeen lactone derivatives including five butenolides (1–5), seven (3S)-resorcylide derivatives (6–12), two butenolide-resorcylide dimers (13 and 14), and three dihydroisocoumarins (15–17). Among them, fourteen compounds (1–3, 6–16) are new natural products. The structures of the isolated compounds were elucidated by 1D and 2D NMR (Nuclear Magnetic Resonance) spectroscopy as well as by ESI-HRMS (ElectroSpray Ionization-High Resolution Mass Spectrometry). TDDFT-ECD (Time-Dependent Density Functional Theory-Electronic Circular Dichroism) calculations were performed to determine the absolute configurations of chiral compounds. The butenolide-resorcylide dimers talarodilactones A and B (13 and 14) exhibited potent cytotoxicity against the L5178Y murine lymphoma cell line with IC₅₀ values of 3.9 and 1.3 µM, respectively. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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1927 KiB

Open AccessArticle

Biological and Chemical Diversity of Bacteria Associated with a Marine Flatworm

by Hui-Na Lin, Kai-Ling Wang, Ze-Hong Wu, Ren-Mao Tian, Guo-Zhu Liu and Ying Xu

Mar. Drugs 2017, 15(9), 281; https://doi.org/10.3390/md15090281 - 01 Sep 2017

Cited by 19 | Viewed by 4503

Abstract

The aim of this research is to explore the biological and chemical diversity of bacteria associated with a marine flatworm Paraplanocera sp., and to discover the bioactive metabolites from culturable strains. A total of 141 strains of bacteria including 45 strains of actinomycetes [...] Read more.

The aim of this research is to explore the biological and chemical diversity of bacteria associated with a marine flatworm Paraplanocera sp., and to discover the bioactive metabolites from culturable strains. A total of 141 strains of bacteria including 45 strains of actinomycetes and 96 strains of other bacteria were isolated, identified and fermented on a small scale. Bioactive screening (antibacterial and cytotoxic activities) and chemical screening (ultra-performance liquid chromatography–mass spectrometry (UPLC-MS)) yielded several target bacterial strains. Among these strains, the ethyl acetate (EA) crude extract of Streptomyces sp. XY-FW47 fermentation broth showed strong antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC43300 (MRSA ATCC43300) and potent cytotoxic effects on HeLa cells. The UPLC-MS spectral analysis of the crude extract indicated that the strain XY-FW47 could produce a series of geldanamycins (GMs). One new geldanamycin (GM) analog, 4,5-dihydro-17-O-demethylgeldanamycin (1), and three known GMs (2–4) were obtained. All of these compounds were tested for antibacterial, cytotoxic, and antifungal activities, yet only GM (3) showed potent cytotoxic (HeLa cells, EC₅₀ = 1.12 μg/mL) and antifungal (Setosphaeria turcica MIC = 2.40 μg/mL) activities. Their structure–activity relationship (SAR) was also preliminarily discussed in this study. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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3432 KiB

Open AccessArticle

5-Hydroxycyclopenicillone, a New β-Amyloid Fibrillization Inhibitor from a Sponge-Derived Fungus Trichoderma sp. HPQJ-34

by Fang Fang, Jiaying Zhao, Lijian Ding, Chunhui Huang, C. Benjamin Naman, Shan He, Bin Wu, Peng Zhu, Qijun Luo, William H. Gerwick, Xiaojun Yan, Qinwen Wang, Zaijun Zhang and Wei Cui

Mar. Drugs 2017, 15(8), 260; https://doi.org/10.3390/md15080260 - 19 Aug 2017

Cited by 27 | Viewed by 4864

Abstract

Abstract: A new cyclopentenone, 5-hydroxycyclopeni cillone (1), was isolated together with three known compounds, ar-turmerone (2), citreoisocoumarin (3), and 6-O-methyl-citreoisocoumarin (4), from a culture of the sponge-derived fungus Trichoderma sp. HPQJ-34. The [...] Read more.

Abstract: A new cyclopentenone, 5-hydroxycyclopeni cillone (1), was isolated together with three known compounds, ar-turmerone (2), citreoisocoumarin (3), and 6-O-methyl-citreoisocoumarin (4), from a culture of the sponge-derived fungus Trichoderma sp. HPQJ-34. The structures of 1–4 were characterized using comprehensive spectroscopic analyses. The absolute configuration of 1 was determined by comparison of electronic circular dichroism (ECD) spectra with literature values used for the reported analogue, cyclopenicillone (5), which was not isolated in this research. Compound 1 was shown to scavenge 2,2-diphenyl-1-picrylhydrazyl free radicals, and decrease β-amyloid (Aβ) fibrillization in vitro. Moreover, 1 significantly reduced H₂O₂-induced neurotoxicity in SH-SY5Y cells. These findings suggested that compound 1, a newly discovered cyclopentenone, has moderate anti-oxidative, anti-Aβ fibrillization properties and neuroprotective effects, and might be a good free radical scavenger. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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1676 KiB

Open AccessArticle

A Novel Benzoquinone Compound Isolated from Deep-Sea Hydrothermal Vent Triggers Apoptosis of Tumor Cells

by Chenxi Xu, Xumei Sun, Min Jin and Xiaobo Zhang

Mar. Drugs 2017, 15(7), 200; https://doi.org/10.3390/md15070200 - 26 Jun 2017

Cited by 17 | Viewed by 4691

Abstract

Microorganisms are important sources for screening bioactive natural products. However, natural products from deep-sea microbes have not been extensively explored. In this study, the metabolites of bacteriophage GVE2 -infected (Geobacillus sp. E263 virus) thermophilic bacterium Geobacillus sp. E263, which was isolated from [...] Read more.

Microorganisms are important sources for screening bioactive natural products. However, natural products from deep-sea microbes have not been extensively explored. In this study, the metabolites of bacteriophage GVE2 -infected (Geobacillus sp. E263 virus) thermophilic bacterium Geobacillus sp. E263, which was isolated from a deep-sea hydrothermal vent, were characterized. A novel quinoid compound, which had anti-tumor activity, was isolated from the phage-challenged thermophile. The chemical structure analysis showed that this novel quinoid compound was 2-amino-6-hydroxy-[1,4]-benzoquinone. The results indicated that 2-amino-6-hydroxy-[1,4]-benzoquinone and its two derivatives could trigger apoptosis of gastric cancer cells and breast cancer cells by inducing the accumulation of intracellular reactive oxygen species. Therefore, our study highlighted that the metabolites from the phage-challenged deep-sea microbes might be a kind of promising sources for anti-tumor drug discovery, because of the similarity of metabolic disorder between bacteriophage-infected microbes and tumor cells. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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1064 KiB

Open AccessArticle

Effect of Supercritical Carbon Dioxide Extraction Parameters on the Biological Activities and Metabolites Present in Extracts from Arthrospira platensis

by Diego A. Esquivel-Hernández, José Rodríguez-Rodríguez, Sara P. Cuéllar-Bermúdez, J. Saúl García-Pérez, Elena I. Mancera-Andrade, Jade E. Núñez-Echevarría, Aura Ontiveros-Valencia, Magdalena Rostro-Alanis, Rebeca M. García-García, J. Antonio Torres, Wei Ning Chen and Roberto Parra-Saldívar

Mar. Drugs 2017, 15(6), 174; https://doi.org/10.3390/md15060174 - 12 Jun 2017

Cited by 25 | Viewed by 5739

Abstract

Arthrospira platensis was used to obtain functional extracts through supercritical carbon dioxide extraction (SFE-CO₂). Pressure (P), temperature (T), co-solvent (CX), static extraction (SX), dispersant (Di) and dynamic extraction (DX) were evaluated as process parameters through a Plackett–Burman design. The maximum extract [...] Read more.

Arthrospira platensis was used to obtain functional extracts through supercritical carbon dioxide extraction (SFE-CO₂). Pressure (P), temperature (T), co-solvent (CX), static extraction (SX), dispersant (Di) and dynamic extraction (DX) were evaluated as process parameters through a Plackett–Burman design. The maximum extract yield obtained was 7.48 ± 0.15% w/w. The maximum contents of bioactive metabolites in extracts were 0.69 ± 0.09 µg/g of riboflavin, 5.49 ± 0.10 µg/g of α-tocopherol, 524.46 ± 0.10 µg/g of β-carotene, 1.44 ± 0.10 µg/g of lutein and 32.11 ± 0.12 mg/g of fatty acids with 39.38% of palmitic acid, 20.63% of linoleic acid and 30.27% of γ-linolenic acid. A. platensis extracts had an antioxidant activity of 76.47 ± 0.71 µg GAE/g by Folin–Ciocalteu assay, 0.52 ± 0.02, 0.40 ± 0.01 and 1.47 ± 0.02 µmol TE/g by DPPH, FRAP and TEAC assays, respectively. These extracts showed antimicrobial activity against Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922 and Candida albicans ATCC 10231. Overall, co-solvent was the most significant factor for all measured effects (p < 0.05). Arthrospira platensis represents a sustainable source of bioactive compounds through SFE using the following extraction parameters P: 450 bar, CX: 11 g/min, SX: 15 min, DX: 25 min, T: 60 °C and Di: 35 g. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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1814 KiB

Open AccessArticle

Three New Indole Diterpenoids from the Sea-Anemone-Derived Fungus Penicillium sp. AS-79

by Xue-Yi Hu, Ling-Hong Meng, Xin Li, Sui-Qun Yang, Xiao-Ming Li and Bin-Gui Wang

Mar. Drugs 2017, 15(5), 137; https://doi.org/10.3390/md15050137 - 12 May 2017

Cited by 30 | Viewed by 4865

Abstract

Three new indolediterpenoids, namely, 22-hydroxylshearinine F (1), 6-hydroxylpaspalinine (2), and 7-O-acetylemindole SB (3), along with eight related known analogs (4–11), were isolated from the sea-anemone-derived fungus Penicillium sp. AS-79. The structures [...] Read more.

Three new indolediterpenoids, namely, 22-hydroxylshearinine F (1), 6-hydroxylpaspalinine (2), and 7-O-acetylemindole SB (3), along with eight related known analogs (4–11), were isolated from the sea-anemone-derived fungus Penicillium sp. AS-79. The structures and relative configurations of these compounds were determined by a detailed interpretation of the spectroscopic data, and their absolute configurations were determined by ECD calculations (1 and 2) and single-crystal X-ray diffraction (3). Some of these compounds exhibited prominent activity against aquatic and human pathogenic microbes. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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Review

Jump to: Research

25 pages, 4732 KiB

Open AccessReview

Bioactive Secondary Metabolites from Octocoral-Associated Microbes—New Chances for Blue Growth

by Inês Raimundo, Sandra G. Silva, Rodrigo Costa and Tina Keller-Costa

Mar. Drugs 2018, 16(12), 485; https://doi.org/10.3390/md16120485 - 04 Dec 2018

Cited by 60 | Viewed by 9267

Abstract

Octocorals (Cnidaria, Anthozoa Octocorallia) are magnificent repositories of natural products with fascinating and unusual chemical structures and bioactivities of interest to medicine and biotechnology. However, mechanistic understanding of the contribution of microbial symbionts to the chemical diversity of octocorals is yet to be [...] Read more.

Octocorals (Cnidaria, Anthozoa Octocorallia) are magnificent repositories of natural products with fascinating and unusual chemical structures and bioactivities of interest to medicine and biotechnology. However, mechanistic understanding of the contribution of microbial symbionts to the chemical diversity of octocorals is yet to be achieved. This review inventories the natural products so-far described for octocoral-derived bacteria and fungi, uncovering a true chemical arsenal of terpenes, steroids, alkaloids, and polyketides with antibacterial, antifungal, antiviral, antifouling, anticancer, anti-inflammatory, and antimalarial activities of enormous potential for blue growth. Genome mining of 15 bacterial associates (spanning 12 genera) cultivated from Eunicella spp. resulted in the identification of 440 putative and classifiable secondary metabolite biosynthetic gene clusters (BGCs), encompassing varied terpene-, polyketide-, bacteriocin-, and nonribosomal peptide-synthase BGCs. This points towards a widespread yet uncharted capacity of octocoral-associated bacteria to synthetize a broad range of natural products. However, to extend our knowledge and foster the near-future laboratory production of bioactive compounds from (cultivatable and currently uncultivatable) octocoral symbionts, optimal blending between targeted metagenomics, DNA recombinant technologies, improved symbiont cultivation, functional genomics, and analytical chemistry are required. Such a multidisciplinary undertaking is key to achieving a sustainable response to the urgent industrial demand for novel drugs and enzyme varieties. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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3401 KiB

Open AccessReview

Cytotoxic Natural Products from Marine Sponge-Derived Microorganisms

by Huawei Zhang, Ziping Zhao and Hong Wang

Mar. Drugs 2017, 15(3), 68; https://doi.org/10.3390/md15030068 - 10 Mar 2017

Cited by 52 | Viewed by 9482

Abstract

A growing body of evidence indicates that marine sponge-derived microbes possess the potential ability to make prolific natural products with therapeutic effects. This review for the first time provides a comprehensive overview of new cytotoxic agents from these marine microbes over the last [...] Read more.

A growing body of evidence indicates that marine sponge-derived microbes possess the potential ability to make prolific natural products with therapeutic effects. This review for the first time provides a comprehensive overview of new cytotoxic agents from these marine microbes over the last 62 years from 1955 to 2016, which are assorted into seven types: terpenes, alkaloids, peptides, aromatics, lactones, steroids, and miscellaneous compounds. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes - II)

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