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Mar. Drugs, Volume 15, Issue 11 (November 2017)

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Cover Story (view full-size image) Shown on the cover is Agelas clathrodes, also known as the orange elephant ear sponge. This [...] Read more.
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Open AccessArticle High-Throughput Identification of Antimicrobial Peptides from Amphibious Mudskippers
Mar. Drugs 2017, 15(11), 364; https://doi.org/10.3390/md15110364
Received: 26 October 2017 / Revised: 12 November 2017 / Accepted: 15 November 2017 / Published: 22 November 2017
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Abstract
Widespread existence of antimicrobial peptides (AMPs) has been reported in various animals with comprehensive biological activities, which is consistent with the important roles of AMPs as the first line of host defense system. However, no big-data-based analysis on AMPs from any fish species
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Widespread existence of antimicrobial peptides (AMPs) has been reported in various animals with comprehensive biological activities, which is consistent with the important roles of AMPs as the first line of host defense system. However, no big-data-based analysis on AMPs from any fish species is available. In this study, we identified 507 AMP transcripts on the basis of our previously reported genomes and transcriptomes of two representative amphibious mudskippers, Boleophthalmus pectinirostris (BP) and Periophthalmus magnuspinnatus (PM). The former is predominantly aquatic with less time out of water, while the latter is primarily terrestrial with extended periods of time on land. Within these identified AMPs, 449 sequences are novel; 15 were reported in BP previously; 48 are identically overlapped between BP and PM; 94 were validated by mass spectrometry. Moreover, most AMPs presented differential tissue transcription patterns in the two mudskippers. Interestingly, we discovered two AMPs, hemoglobin β1 and amylin, with high inhibitions on Micrococcus luteus. In conclusion, our high-throughput screening strategy based on genomic and transcriptomic data opens an efficient pathway to discover new antimicrobial peptides for ongoing development of marine drugs. Full article
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Open AccessShort Note Aspersymmetide A, a New Centrosymmetric Cyclohexapeptide from the Marine-Derived Fungus Aspergillus versicolor
Mar. Drugs 2017, 15(11), 363; https://doi.org/10.3390/md15110363
Received: 10 October 2017 / Revised: 31 October 2017 / Accepted: 13 November 2017 / Published: 22 November 2017
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Abstract
A new centrosymmetric cyclohexapeptide, aspersymmetide A (1), together with a known peptide, asperphenamate (2), was isolated from the fungus Aspergillus versicolor isolated from a gorgonian coral Carijoa sp., collected from the South China Sea. The chemical structure of 1
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A new centrosymmetric cyclohexapeptide, aspersymmetide A (1), together with a known peptide, asperphenamate (2), was isolated from the fungus Aspergillus versicolor isolated from a gorgonian coral Carijoa sp., collected from the South China Sea. The chemical structure of 1 was elucidated by analyzing its NMR spectroscopy and MS spectrometry data, and the absolute configurations of the amino acids of 1 were determined by Marfey’s method and UPLC-MS analysis of the hydrolysate. Aspersymmetide A (1) represents the first example of marine-derived centrosymmetric cyclohexapeptide. Moreover, 1 exhibited weak cytotoxicity against NCI-H292 and A431 cell lines at the concentration of 10 μM. Full article
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Open AccessArticle Antimicrobial Peptide Epinecidin-1 Modulates MyD88 Protein Levels via the Proteasome Degradation Pathway
Mar. Drugs 2017, 15(11), 362; https://doi.org/10.3390/md15110362
Received: 27 October 2017 / Revised: 10 November 2017 / Accepted: 14 November 2017 / Published: 16 November 2017
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Abstract
The cationic antimicrobial peptide epinecidin-1 was identified from Epinephelus coioides and possesses multiple biological functions, including antibacterial, antifungal, anti-tumor, and immunomodulatory effects. In addition, epinecidin-1 suppresses lipopolysaccharide (LPS)-induced inflammation by neutralizing LPS and ameliorating LPS/Toll-like receptor (TLR)-4 internalization. However, it is unclear whether
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The cationic antimicrobial peptide epinecidin-1 was identified from Epinephelus coioides and possesses multiple biological functions, including antibacterial, antifungal, anti-tumor, and immunomodulatory effects. In addition, epinecidin-1 suppresses lipopolysaccharide (LPS)-induced inflammation by neutralizing LPS and ameliorating LPS/Toll-like receptor (TLR)-4 internalization. However, it is unclear whether the actions of epinecidin-1 depend on the regulation of TLR adaptor protein MyD88 or endogenous TLR signaling antagonists, which include A20, interleukin-1 receptor associated kinase (IRAK)-M, and suppressor of cytokine signaling (SOCS)-1. Our results demonstrate that epinecidin-1 alone does not affect A20, IRAK-M, or SOCS-1 protein levels. However, pre-incubation of epinecidin-1 significantly inhibits LPS-induced upregulation of A20, IRAK-M, and SOCS-1. In addition, epinecidin-1 significantly reduces the abundance of MyD88 protein. Both MG132 (a specific proteasome inhibitor) and Heclin (a specific Smurf E3 ligase inhibitor) are able to abolish epinecidin-1-mediated MyD88 degradation. Thus, our data suggest that epinecidin-1 directly inhibits MyD88 via induction of the Smurf E3 ligase proteasome pathway. Full article
(This article belongs to the Special Issue Marine Antimicrobial Agents)
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Open AccessFeature PaperReview The Oxepane Motif in Marine Drugs
Mar. Drugs 2017, 15(11), 361; https://doi.org/10.3390/md15110361
Received: 29 September 2017 / Revised: 3 November 2017 / Accepted: 8 November 2017 / Published: 15 November 2017
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Abstract
Oceans have shown to be a remarkable source of natural products. The biological properties of many of these compounds have helped to produce great advances in medicinal chemistry. Within them, marine natural products containing an oxepanyl ring are present in a great variety
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Oceans have shown to be a remarkable source of natural products. The biological properties of many of these compounds have helped to produce great advances in medicinal chemistry. Within them, marine natural products containing an oxepanyl ring are present in a great variety of algae, sponges, fungus and corals and show very important biological activities, many of them possessing remarkable cytotoxic properties against a wide range of cancer cell lines. Their rich chemical structures have attracted the attention of many researchers who have reported interesting synthetic approaches to these targets. This review covers the most prominent examples of these types of compounds, focusing the discussion on the isolation, structure determination, medicinal properties and total synthesis of these products. Full article
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Open AccessArticle Proximate Composition and Nutritional Value of Three Macroalgae: Ascophyllum nodosum, Fucus vesiculosus and Bifurcaria bifurcata
Mar. Drugs 2017, 15(11), 360; https://doi.org/10.3390/md15110360
Received: 8 August 2017 / Revised: 7 November 2017 / Accepted: 8 November 2017 / Published: 15 November 2017
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Abstract
Proximate composition (moisture, protein, lipid and ash content) and nutritional value (fatty acid, amino acid and mineral profile) of three macroalgae (Ascophyllum nodosum, Fucus vesiculosus and Bifurcaria bifurcate) were studied. Chemical composition was significantly (p < 0.001) different among
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Proximate composition (moisture, protein, lipid and ash content) and nutritional value (fatty acid, amino acid and mineral profile) of three macroalgae (Ascophyllum nodosum, Fucus vesiculosus and Bifurcaria bifurcate) were studied. Chemical composition was significantly (p < 0.001) different among the three seaweeds. In this regard, the B. bifurcata presented the highest fat content (6.54% of dry matter); whereas, F. vesiculosus showed the highest protein level (12.99% dry matter). Regarding fatty acid content, the polyunsaturated fatty acids (PUFAs) were the most abundant followed by saturated fatty acids (SFAs) and monounsaturated fatty acids (MUFAs). On the other hand, the three seaweeds are a rich source of K (from 3781.35 to 9316.28 mg/100 g), Mn (from 8.28 to 1.96 mg/100 g), Na (from 1836.82 to 4575.71 mg/100 g) and Ca (from 984.73 to 1160.27 mg/100 g). Finally, the most abundant amino acid was glutamic acid (1874.47–1504.53 mg/100 dry matter), followed by aspartic acid (1677.01–800.84 mg/100 g dry matter) and alanine (985.40–655.73 mg/100 g dry matter). Full article
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Open AccessArticle Lactones from the Sponge-Derived Fungus Talaromyces rugulosus
Mar. Drugs 2017, 15(11), 359; https://doi.org/10.3390/md15110359
Received: 12 October 2017 / Revised: 6 November 2017 / Accepted: 9 November 2017 / Published: 14 November 2017
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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 (15), seven (3S)-resorcylide derivatives (612), two butenolide-resorcylide dimers
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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 (15), seven (3S)-resorcylide derivatives (612), two butenolide-resorcylide dimers (13 and 14), and three dihydroisocoumarins (1517). Among them, fourteen compounds (13, 616) 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, 2017)
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Open AccessArticle Asperlin Inhibits LPS-Evoked Foam Cell Formation and Prevents Atherosclerosis in ApoE−/− Mice
Mar. Drugs 2017, 15(11), 358; https://doi.org/10.3390/md15110358
Received: 18 September 2017 / Revised: 2 November 2017 / Accepted: 7 November 2017 / Published: 14 November 2017
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Abstract
Asperlin is a marine-derived natural product with antifungal and anti-inflammatory activities in vitro. In the present study, we isolated asperlin from a marine Aspergillus versicolor LZD4403 fungus and investigated its anti-atherosclerotic effects in vitro and in vivo. Asperlin significantly inhibited lipopolysaccharides (LPS)- but
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Asperlin is a marine-derived natural product with antifungal and anti-inflammatory activities in vitro. In the present study, we isolated asperlin from a marine Aspergillus versicolor LZD4403 fungus and investigated its anti-atherosclerotic effects in vitro and in vivo. Asperlin significantly inhibited lipopolysaccharides (LPS)- but not oxidated low-density lipoprotein (oxLDL)-evoked foam cell formation and promoted cholesterol efflux in RAW264.7 macrophages. Supplementation with asperlin also suppressed LPS-elicited production of pro-inflammatory factors in RAW264.7 macrophages, decreased the expression levels of iNOS, IL-1β and TNFα, and increased the expression of IL-10 and IL-4, indicating a remarkable shift in M1/M2 macrophages polarization. In vivo experiments in high-fat diet (HFD)-fed ApoE−/− mice showed that oral administration of asperlin for 12 weeks remarkably suppressed atherosclerotic plaque formation in the aorta, as revealed by the reduced aortic dilatation and decreased atherosclerotic lesion area. Asperlin also decreased serum levels of pro-inflammatory factors but showed little impact on blood lipids in ApoE−/− atherosclerotic mice. These results suggested that asperlin is adequate to prevent atherosclerosis in vivo. It may exert atheroprotective function through suppressing inflammation rather than ameliorating dyslipidemia. Full article
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Open AccessArticle Physiological and Biochemical Changes Reveal Differential Patterns of Docosahexaenoic Acid Partitioning in Two Marine Algal Strains of Isochrysis
Mar. Drugs 2017, 15(11), 357; https://doi.org/10.3390/md15110357
Received: 1 October 2017 / Revised: 31 October 2017 / Accepted: 6 November 2017 / Published: 12 November 2017
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Abstract
The marine microalgae Isochrysis are a good producer of natural docosahexaenoic acid (DHA). To better understand the patterns of DHA accumulation and distribution, two Isochrysis strains, CL153180 and CCMP462, were evaluated in this study. In a batch culture, CL153180 showed a decline in
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The marine microalgae Isochrysis are a good producer of natural docosahexaenoic acid (DHA). To better understand the patterns of DHA accumulation and distribution, two Isochrysis strains, CL153180 and CCMP462, were evaluated in this study. In a batch culture, CL153180 showed a decline in DHA content while CCMP462 exhibited a progressive increase during the late growth period when nitrogen was almost exhausted. In response to nitrogen deficiency (ND), both strains showed a considerable increase in neutral lipids (NL) at the expense of glycolipids (GL) but had little variation in phospholipids (PL). In CL153180, the DHA percentage of NL decreased gradually upon ND, while that in CCMP462 increased progressively to 21.4% after 4 days of ND, which is around 5-fold higher than CL153180. Accordingly, in contrast to CL153180 that stored DHA predominantly in GL, CCMP462 accumulated DHA mainly in NL in late days of ND. Taken together, we proposed a working model for the differential DHA partitioning patterns between two Isochrysis strains: for CCMP462, the degradation of GL released free fatty acids including DHA, which was incorporated into NL upon ND; whereas for CL153180, the released DHA from GL might not be incorporated into NL, and, consequently, might be subject to β-oxidation for degradation. Full article
(This article belongs to the collection Bioactive Compounds from Marine Plankton)
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Open AccessFeature PaperArticle New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.
Mar. Drugs 2017, 15(11), 356; https://doi.org/10.3390/md15110356
Received: 5 August 2017 / Revised: 1 November 2017 / Accepted: 6 November 2017 / Published: 11 November 2017
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Abstract
Three new 2-methoxy acetylenic acids (1–3) and a known derivative (4), in addition to three new natural pyrazole alkaloids (5–7) were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The
[...] Read more.
Three new 2-methoxy acetylenic acids (1–3) and a known derivative (4), in addition to three new natural pyrazole alkaloids (5–7) were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopy as well as by mass spectrometric data. The absolute configuration of the new acetylenic acid derivatives (1–3) was established by ECD spectroscopy. All isolated compounds were evaluated for their cytotoxicity against L5178Y mouse lymphoma cells. Compounds 1–4 exhibited strong activity with an IC50 value of 0.3 µM. A plausible biosynthetic pathway for the pyrazole metabolites 5–7 is proposed. Full article
(This article belongs to the collection Bioactive Compounds from Marine Invertebrates)
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Open AccessArticle Anandins A and B, Two Rare Steroidal Alkaloids from a Marine Streptomyces anandii H41-59
Mar. Drugs 2017, 15(11), 355; https://doi.org/10.3390/md15110355
Received: 26 August 2017 / Revised: 1 November 2017 / Accepted: 2 November 2017 / Published: 10 November 2017
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Abstract
Anandins A (1) and B (2), two rare steroidal alkaloids, were isolated from the fermentative broth of a marine actinobacteria Streptomyces anandii H41-59. The gross structures of the two alkaloids were elucidated by spectroscopic methods including HR-ESI-MS, and NMR.
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Anandins A (1) and B (2), two rare steroidal alkaloids, were isolated from the fermentative broth of a marine actinobacteria Streptomyces anandii H41-59. The gross structures of the two alkaloids were elucidated by spectroscopic methods including HR-ESI-MS, and NMR. Their absolute configurations were confirmed by single-crystal X-ray diffraction analysis and comparison of their experimental and calculated electronic circular dichroism spectra, respectively. Anandin A exhibited a moderate inhibitory effect against three human cancer cell lines MCF-7, SF-268, and NCI-H460 with IC50 values of 7.5, 7.9, 7.8 μg/mL, respectively. Full article
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Open AccessReview Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review
Mar. Drugs 2017, 15(11), 354; https://doi.org/10.3390/md15110354
Received: 29 September 2017 / Revised: 1 November 2017 / Accepted: 3 November 2017 / Published: 10 November 2017
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Abstract
Nowadays, various drugs on the market are becoming more and more resistant to numerous diseases, thus declining their efficacy for treatment purposes in human beings. Antibiotic resistance is one among the top listed threat around the world which eventually urged the discovery of
[...] Read more.
Nowadays, various drugs on the market are becoming more and more resistant to numerous diseases, thus declining their efficacy for treatment purposes in human beings. Antibiotic resistance is one among the top listed threat around the world which eventually urged the discovery of new potent drugs followed by an increase in the number of deaths caused by cancer due to chemotherapy resistance as well. Accordingly, marine cyanobacteria, being the oldest prokaryotic microorganisms belonging to a monophyletic group, have proven themselves as being able to generate pharmaceutically important natural products. They have long been known to produce distinct and structurally complex secondary metabolites including peptides, polyketides, alkaloids, lipids, and terpenes with potent biological properties and applications. As such, this review will focus on recently published novel compounds isolated from marine cyanobacteria along with their potential bioactivities such as antibacterial, antifungal, anticancer, anti-tuberculosis, immunosuppressive and anti-inflammatory capacities. Moreover, various structural classes, as well as their technological uses will also be discussed. Full article
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Open AccessArticle An Insight into Sargassum muticum Cytoprotective Mechanisms against Oxidative Stress on a Human Cell In Vitro Model
Mar. Drugs 2017, 15(11), 353; https://doi.org/10.3390/md15110353
Received: 10 May 2017 / Revised: 17 October 2017 / Accepted: 4 November 2017 / Published: 10 November 2017
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Abstract
Sargassum muticum is a brown seaweed with strong potential to be used as a functional food ingredient, mainly due to its antioxidant properties. It is widely used in traditional oriental medicine for the treatment of numerous diseases. Nevertheless, few studies have been conducted
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Sargassum muticum is a brown seaweed with strong potential to be used as a functional food ingredient, mainly due to its antioxidant properties. It is widely used in traditional oriental medicine for the treatment of numerous diseases. Nevertheless, few studies have been conducted to add scientific evidence on its effects as well as on the mechanisms of action involved. In this work, the human cell line MCF-7 was used as an in vitro cellular model to evaluate the capability of Sargassum muticum enriched fractions to protect cells on an oxidative stress condition. The concentration of the bioactive compounds was obtained by vacuum liquid chromatography applied on methanol (M) and 1:1 methanol:dichloromethane (MD) crude extracts, resulting in seven enriched fractions from the M extraction (MF2–MF8), and eight fractions from the MD extraction (MDF1–MDF8). All fractions were tested for cytotoxic properties on MCF-7 cells and the nontoxic ones were tested for their capacity to blunt the damaging effects of hydrogen peroxide-induced oxidative stress. The nontoxic effects were also confirmed in 3T3 fibroblast cells as a nontumor cell line. The antioxidant potential of each fraction, as well as changes in the cell’s real-time hydrogen peroxide production, in the mitochondrial membrane potential, and in Caspase-9 activity were evaluated. The results suggest that the protective effects evidenced by S. muticum can be related with the inhibition of hydrogen peroxide production and the inhibition of Caspase-9 activity. Full article
(This article belongs to the Special Issue Nutraceuticals and Functional Foods)
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Open AccessReview Bioactive Secondary Metabolites from the Marine Sponge Genus Agelas
Mar. Drugs 2017, 15(11), 351; https://doi.org/10.3390/md15110351
Received: 19 September 2017 / Revised: 25 October 2017 / Accepted: 3 November 2017 / Published: 8 November 2017
Cited by 1 | PDF Full-text (7740 KB) | HTML Full-text | XML Full-text
Abstract
The marine sponge genus Agelas comprises a rich reservoir of species and natural products with diverse chemical structures and biological properties with potential application in new drug development. This review for the first time summarized secondary metabolites from Agelas sponges discovered in the
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The marine sponge genus Agelas comprises a rich reservoir of species and natural products with diverse chemical structures and biological properties with potential application in new drug development. This review for the first time summarized secondary metabolites from Agelas sponges discovered in the past 47 years together with their bioactive effects. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges)
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Open AccessFeature PaperArticle Reclamation of Marine Chitinous Materials for the Production of α-Glucosidase Inhibitors via Microbial Conversion
Mar. Drugs 2017, 15(11), 350; https://doi.org/10.3390/md15110350
Received: 4 October 2017 / Revised: 29 October 2017 / Accepted: 3 November 2017 / Published: 7 November 2017
Cited by 2 | PDF Full-text (1160 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Six kinds of chitinous materials have been used as sole carbon/nitrogen (C/N) sources for producing α-glucosidase inhibitors (aGI) by Paenibacillus sp. TKU042. The aGI productivity was found to be highest in the culture supernatants using demineralized crab shell powder (deCSP) and demineralized shrimp
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Six kinds of chitinous materials have been used as sole carbon/nitrogen (C/N) sources for producing α-glucosidase inhibitors (aGI) by Paenibacillus sp. TKU042. The aGI productivity was found to be highest in the culture supernatants using demineralized crab shell powder (deCSP) and demineralized shrimp shell powder (deSSP) as the C/N source. The half maximal inhibitory concentration (IC50) and maximum aGI activity of fermented deCSP (38 µg/mL, 98%), deSSP (108 µg/mL, 89%), squid pen powder (SPP) (422 µg/mL, 98%), and shrimp head powder (SHP) (455 µg/mL, 92%) were compared with those of fermented nutrient broth (FNB) (81 µg/mL, 93%) and acarbose (1095 µg/mL, 74%), a commercial antidiabetic drug. The result of the protein/chitin ratio on aGI production showed that the optimal ratio was 0.2/1. Fermented deCSP showed lower IC50 and higher maximum inhibitory activity than those of acarbose against rat intestinal α-glucosidase. Full article
(This article belongs to the Special Issue Bioconversion of Marine Resources)
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Open AccessArticle Evidence for a Saponin Biosynthesis Pathway in the Body Wall of the Commercially Significant Sea Cucumber Holothuria scabra
Mar. Drugs 2017, 15(11), 349; https://doi.org/10.3390/md15110349
Received: 9 August 2017 / Revised: 30 October 2017 / Accepted: 31 October 2017 / Published: 7 November 2017
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Abstract
The sea cucumber (phylum Echinodermata) body wall is the first line of defense and is well known for its production of secondary metabolites; including vitamins and triterpenoid glycoside saponins that have important ecological functions and potential benefits to human health. The genes involved
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The sea cucumber (phylum Echinodermata) body wall is the first line of defense and is well known for its production of secondary metabolites; including vitamins and triterpenoid glycoside saponins that have important ecological functions and potential benefits to human health. The genes involved in the various biosynthetic pathways are unknown. To gain insight into these pathways in an echinoderm, we performed a comparative transcriptome analysis and functional annotation of the body wall and the radial nerve of the sea cucumber Holothuria scabra; to define genes associated with body wall metabolic functioning and secondary metabolite biosynthesis. We show that genes related to signal transduction mechanisms were more highly represented in the H. scabra body wall, including genes encoding enzymes involved in energy production. Eight of the core triterpenoid biosynthesis enzymes were found, however, the identity of the saponin specific biosynthetic pathway enzymes remains unknown. We confirm the body wall release of at least three different triterpenoid saponins using solid phase extraction followed by ultra-high-pressure liquid chromatography-quadrupole time of flight-mass spectrometry. The resource we have established will help to guide future research to explore secondary metabolite biosynthesis in the sea cucumber. Full article
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