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Mar. Drugs, Volume 12, Issue 12 (December 2014), Pages 5719-6268

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Open AccessArticle Multiple Beneficial Lipids Including Lecithin Detected in the Edible Invasive Mollusk Crepidula fornicata from the French Northeastern Atlantic Coast
Mar. Drugs 2014, 12(12), 6254-6268; https://doi.org/10.3390/md12126254
Received: 29 September 2014 / Revised: 8 December 2014 / Accepted: 10 December 2014 / Published: 22 December 2014
Cited by 3 | PDF Full-text (400 KB) | HTML Full-text | XML Full-text
Abstract
The invasive mollusk Crepidula fornicata, occurring in large amounts in bays along the French Northeastern Atlantic coasts, may have huge environmental effects in highly productive ecosystems where shellfish are exploited. The present study aims at determining the potential economic value of this marine
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The invasive mollusk Crepidula fornicata, occurring in large amounts in bays along the French Northeastern Atlantic coasts, may have huge environmental effects in highly productive ecosystems where shellfish are exploited. The present study aims at determining the potential economic value of this marine species in terms of exploitable substances with high added value. Lipid content and phospholipid (PL) composition of this mollusk collected on the Bourgneuf Bay were studied through four seasons. Winter specimens contained the highest lipid levels (5.3% dry weight), including 69% of PLs. Phosphatidylcholine (PC) was the major PL class all year, accounting for 63.9% to 88.9% of total PLs. Consequently, the winter specimens were then investigated for PL fatty acids (FAs), and free sterols. Dimethylacetals (DMAs) were present (10.7% of PL FA + DMA mixture) revealing the occurrence of plasmalogens. More than forty FAs were identified, including 20:5n-3 (9.4%) and 22:6n-3 (7.3%) acids. Fourteen free sterols were present, including cholesterol at 31.3% of the sterol mixture and about 40% of phytosterols. These data on lipids of C. fornicata demonstrate their positive attributes for human nutrition and health. The PL mixture, rich in PC and polyunsaturated FAs, offers an interesting alternative source of high value-added marine lecithin. Full article
(This article belongs to the Special Issue Marine Lipids)
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Open AccessReview Design of Chitosan and Its Water Soluble Derivatives-Based Drug Carriers with Polyelectrolyte Complexes
Mar. Drugs 2014, 12(12), 6236-6253; https://doi.org/10.3390/md12126236
Received: 9 October 2014 / Revised: 11 December 2014 / Accepted: 12 December 2014 / Published: 19 December 2014
Cited by 16 | PDF Full-text (535 KB) | HTML Full-text | XML Full-text
Abstract
Chitosan, the cationic polysaccharide derived from the natural polysaccharide chitin, has been studied as a biomaterial for more than two decades. As a polycationic polymer with favorable properties, it has been widely used to form polyelectrolyte complexes with polyanions for various applications in
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Chitosan, the cationic polysaccharide derived from the natural polysaccharide chitin, has been studied as a biomaterial for more than two decades. As a polycationic polymer with favorable properties, it has been widely used to form polyelectrolyte complexes with polyanions for various applications in drug delivery fields. In recent years, a growing number of studies have been focused on the preparation of polyelectrolyte complexes based on chitosan and its water soluble derivatives. They have been considered well-suited as biomaterials for a number of vital drug carriers with targeted/controlled release profiles, e.g., films, capsules, microcapsules. In this work, an overview highlights not only the favorable properties of chitosan and its water soluble derivatives but also the good performance of the polyelectrolyte complexes produced based on chitosan. Their various types of applications as drug carriers are reviewed in detail. Full article
(This article belongs to the Special Issue Advances in Marine Chitin and Chitosan) Printed Edition available
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Open AccessReview An Update on 2,5-Diketopiperazines from Marine Organisms
Mar. Drugs 2014, 12(12), 6213-6235; https://doi.org/10.3390/md12126213
Received: 14 September 2014 / Revised: 5 December 2014 / Accepted: 9 December 2014 / Published: 19 December 2014
Cited by 25 | PDF Full-text (808 KB) | HTML Full-text | XML Full-text
Abstract
2,5-Diketopiperazines (2,5-DKPs) are an important category of structurally diverse cyclic dipeptides with prominent biological properties. These 2,5-DKPs have been obtained from a variety of natural resources, including marine organisms. Because of the increasing numbers and biological importance of these compounds, this review covers
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2,5-Diketopiperazines (2,5-DKPs) are an important category of structurally diverse cyclic dipeptides with prominent biological properties. These 2,5-DKPs have been obtained from a variety of natural resources, including marine organisms. Because of the increasing numbers and biological importance of these compounds, this review covers 90 marine originated 2,5-DKPs that were reported from 2009 to the first half-year of 2014. The review will focus on the structure characterizations, biological properties and proposed biosynthetic processes of these compounds. Full article
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Open AccessReview Impact of DHA on Metabolic Diseases from Womb to Tomb
Mar. Drugs 2014, 12(12), 6190-6212; https://doi.org/10.3390/md12126190
Received: 9 October 2014 / Revised: 25 November 2014 / Accepted: 11 December 2014 / Published: 18 December 2014
Cited by 6 | PDF Full-text (637 KB) | HTML Full-text | XML Full-text
Abstract
Long chain polyunsaturated fatty acids (LC-PUFAs) are important mediators in improving and maintaining human health over the total lifespan. One topic we especially focus on in this review is omega-3 LC-PUFA docosahexaenoic acid (DHA). Adequate DHA levels are essential during neurodevelopment and, in
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Long chain polyunsaturated fatty acids (LC-PUFAs) are important mediators in improving and maintaining human health over the total lifespan. One topic we especially focus on in this review is omega-3 LC-PUFA docosahexaenoic acid (DHA). Adequate DHA levels are essential during neurodevelopment and, in addition, beneficial in cognitive processes throughout life. We review the impact of DHA on societal relevant metabolic diseases such as cardiovascular diseases, obesity, and diabetes mellitus type 2 (T2DM). All of these are risk factors for cognitive decline and dementia in later life. DHA supplementation is associated with a reduced incidence of both stroke and atherosclerosis, lower bodyweight and decreased T2DM prevalence. These findings are discussed in the light of different stages in the human life cycle: childhood, adolescence, adulthood and in later life. From this review, it can be concluded that DHA supplementation is able to inhibit pathologies like obesity and cardiovascular disease. DHA could be a dietary protector against these metabolic diseases during a person’s entire lifespan. However, supplementation of DHA in combination with other dietary factors is also effective. The efficacy of DHA depends on its dose as well as on the duration of supplementation, sex, and age. Full article
(This article belongs to the Special Issue Marine Functional Food Products - Cardiovascular Diseases)
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Open AccessArticle Briarane Diterpenoids from the Gorgonian Dichotella gemmacea
Mar. Drugs 2014, 12(12), 6178-6189; https://doi.org/10.3390/md12126178
Received: 21 October 2014 / Revised: 27 November 2014 / Accepted: 8 December 2014 / Published: 18 December 2014
Cited by 3 | PDF Full-text (189 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Seven new briarane diterpenoids, gemmacolides AS-AY (17), were isolated together with ten known analogues (817) from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the
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Seven new briarane diterpenoids, gemmacolides AS-AY (17), were isolated together with ten known analogues (817) from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data and comparison with reported data. The absolute configuration of compounds was determined based on electronic circular dichroism (ECD) experiments and genetic correlations as well. Compounds 15 and 16 were reported for the first time for the gorgonian. In the preliminary in vitro bioassays, compound 5 showed potential growth inhibitory activity against MG63 cells. Full article
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Open AccessReview Synthetic Approaches to the Lamellarins—A Comprehensive Review
Mar. Drugs 2014, 12(12), 6142-6177; https://doi.org/10.3390/md12126142
Received: 3 November 2014 / Revised: 1 December 2014 / Accepted: 5 December 2014 / Published: 18 December 2014
Cited by 23 | PDF Full-text (5436 KB) | HTML Full-text | XML Full-text
Abstract
The present review discusses the known synthetic routes to the lamellarin alkaloids published until 2014. It begins with syntheses of the structurally simpler type-II lamellarins and then focuses on the larger class of the 5,6-saturated and -unsaturated type-I lamellarins. The syntheses are grouped
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The present review discusses the known synthetic routes to the lamellarin alkaloids published until 2014. It begins with syntheses of the structurally simpler type-II lamellarins and then focuses on the larger class of the 5,6-saturated and -unsaturated type-I lamellarins. The syntheses are grouped by the strategy employed for the assembly of the central pyrrole ring. Full article
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
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Open AccessArticle Astaxanthin Activates Nuclear Factor Erythroid-Related Factor 2 and the Antioxidant Responsive Element (Nrf2-ARE) Pathway in the Brain after Subarachnoid Hemorrhage in Rats and Attenuates Early Brain Injury
Mar. Drugs 2014, 12(12), 6125-6141; https://doi.org/10.3390/md12126125
Received: 9 October 2014 / Revised: 19 November 2014 / Accepted: 8 December 2014 / Published: 18 December 2014
Cited by 28 | PDF Full-text (1175 KB) | HTML Full-text | XML Full-text
Abstract
Astaxanthin (ATX) has been proven to ameliorate early brain injury (EBI) after experimental subarachnoid hemorrhage (SAH) by modulating cerebral oxidative stress. This study was performed to assess the effect of ATX on the Nrf2-ARE pathway and to explore the underlying molecular mechanisms of
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Astaxanthin (ATX) has been proven to ameliorate early brain injury (EBI) after experimental subarachnoid hemorrhage (SAH) by modulating cerebral oxidative stress. This study was performed to assess the effect of ATX on the Nrf2-ARE pathway and to explore the underlying molecular mechanisms of antioxidant properties of ATX in EBI after SAH. A total of 96 male SD rats were randomly divided into four groups. Autologous blood was injected into the prechiasmatic cistern of the rat to induce an experimental SAH model. Rats in each group were sacrificed at 24 h after SAH. Expressions of Nrf2 and heme oxygenase-1 (HO-1) were measured by Western blot and immunohistochemistry analysis. The mRNA levels of HO-1, NAD (P) H: quinone oxidoreductase 1 (NQO-1), and glutathione S-transferase-α1 (GST-α1) were determined by real-time polymerase chain reaction (PCR). It was observed that administration of ATX post-SAH could up-regulate the cortical expression of these agents, mediated in the Nrf2-ARE pathway at both pretranscriptional and posttranscriptional levels. Meanwhile, oxidative damage was reduced. Furthermore, ATX treatment significantly attenuated brain edema, blood–brain barrier (BBB) disruption, cellular apoptosis, and neurological dysfunction in SAH models. This study demonstrated that ATX treatment alleviated EBI in SAH model, possibly through activating the Nrf2-ARE pathway by inducing antioxidant and detoxifying enzymes. Full article
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Open AccessArticle Territrem and Butyrolactone Derivatives from a Marine-Derived Fungus Aspergillus Terreus
Mar. Drugs 2014, 12(12), 6113-6124; https://doi.org/10.3390/md12126113
Received: 17 September 2014 / Revised: 24 November 2014 / Accepted: 8 December 2014 / Published: 17 December 2014
Cited by 16 | PDF Full-text (567 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Seventeen lactones including eight territrem derivatives (18) and nine butyrolactone derivatives (917) were isolated from a marine-derived fungus Aspergillus terreus SCSGAF0162 under solid-state fermentation of rice. Compounds 13 and 910
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Seventeen lactones including eight territrem derivatives (18) and nine butyrolactone derivatives (917) were isolated from a marine-derived fungus Aspergillus terreus SCSGAF0162 under solid-state fermentation of rice. Compounds 13 and 910 were new, and their structures were elucidated by spectroscopic analysis. The acetylcholinesterase inhibitory activity and antiviral activity of compounds 117 were evaluated. Among them, compounds 1 and 2 showed strong inhibitory activity against acetylcholinesterase with IC50 values of 4.2 ± 0.6, 4.5 ± 0.6 nM, respectively. This is the first time it has been reported that 3, 6, 10, 12 had evident antiviral activity towards HSV-1 with IC50 values of 16.4 ± 0.6, 6.34 ± 0.4, 21.8 ± 0.8 and 28.9 ± 0.8 μg·mL−1, respectively. Antifouling bioassay tests showed that compounds 1, 11, 12, 15 had potent antifouling activity with EC50 values of 12.9 ± 0.5, 22.1 ± 0.8, 7.4 ± 0.6, 16.1 ± 0.6 μg·mL−1 toward barnacle Balanus amphitrite larvae, respectively. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle Anti-Mycobacterial Nucleoside Antibiotics from a Marine-Derived Streptomyces sp. TPU1236A
Mar. Drugs 2014, 12(12), 6102-6112; https://doi.org/10.3390/md12126102
Received: 30 October 2014 / Revised: 9 December 2014 / Accepted: 10 December 2014 / Published: 17 December 2014
Cited by 14 | PDF Full-text (663 KB) | HTML Full-text | XML Full-text
Abstract
Five new nucleoside antibiotics, named streptcytosines A–E (15), and six known compounds, de-amosaminyl-cytosamine (6), plicacetin (7), bamicetin (8), amicetin (9), collismycin B (10), and SF2738 C (11),
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Five new nucleoside antibiotics, named streptcytosines A–E (15), and six known compounds, de-amosaminyl-cytosamine (6), plicacetin (7), bamicetin (8), amicetin (9), collismycin B (10), and SF2738 C (11), were isolated from a culture broth of Streptomyces sp. TPU1236A collected in Okinawa, Japan. The structures of new compounds were elucidated on the basis of their spectroscopic data (HRFABMS, IR, UV, and 2D NMR experiments including 1H-1H COSY, HMQC, HMBC, and NOESY spectra). Streptcytosine A (1) belonged to the amicetin group antibiotics, and streptcytosines B–E (25) were derivatives of de-amosaminyl-cytosamine (6), 2,3,6-trideoxyglucopyranosyl cytosine. Compound 1 inhibited the growth of Mycobacterium smegmatis (MIC = 32 µg/mL), while compounds 25 were not active at 50 µg/disc. Bamicetin (8) and amicetin (9) showed the MICs of 16 and 8 µg/mL, respectively. Full article
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Open AccessReview Conotoxin Gene Superfamilies
Mar. Drugs 2014, 12(12), 6058-6101; https://doi.org/10.3390/md12126058
Received: 28 October 2014 / Revised: 29 November 2014 / Accepted: 4 December 2014 / Published: 17 December 2014
Cited by 43 | PDF Full-text (2366 KB) | HTML Full-text | XML Full-text
Abstract
Conotoxins are the peptidic components of the venoms of marine cone snails (genus Conus). They are remarkably diverse in terms of structure and function. Unique potency and selectivity profiles for a range of neuronal targets have made several conotoxins valuable as research
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Conotoxins are the peptidic components of the venoms of marine cone snails (genus Conus). They are remarkably diverse in terms of structure and function. Unique potency and selectivity profiles for a range of neuronal targets have made several conotoxins valuable as research tools, drug leads and even therapeutics, and has resulted in a concerted and increasing drive to identify and characterise new conotoxins. Conotoxins are translated from mRNA as peptide precursors, and cDNA sequencing is now the primary method for identification of new conotoxin sequences. As a result, gene superfamily, a classification based on precursor signal peptide identity, has become the most convenient method of conotoxin classification. Here we review each of the described conotoxin gene superfamilies, with a focus on the structural and functional diversity present in each. This review is intended to serve as a practical guide to conotoxin superfamilies and to facilitate interpretation of the increasing number of conotoxin precursor sequences being identified by targeted-cDNA sequencing and more recently high-throughput transcriptome sequencing. Full article
(This article belongs to the Special Issue Marine Peptides and Their Mimetics)
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Open AccessReview Glycol Chitosan-Based Fluorescent Theranostic Nanoagents for Cancer Therapy
Mar. Drugs 2014, 12(12), 6038-6057; https://doi.org/10.3390/md12126038
Received: 9 October 2014 / Revised: 27 November 2014 / Accepted: 27 November 2014 / Published: 17 December 2014
Cited by 14 | PDF Full-text (1449 KB) | HTML Full-text | XML Full-text
Abstract
Theranostics is an integrated nanosystem that combines therapeutics with diagnostics in attempt to develop new personalized treatments with enhanced therapeutic efficacy and safety. As a promising therapeutic paradigm with cutting-edge technologies, theranostic agents are able to simultaneously deliver therapeutic drugs and diagnostic imaging
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Theranostics is an integrated nanosystem that combines therapeutics with diagnostics in attempt to develop new personalized treatments with enhanced therapeutic efficacy and safety. As a promising therapeutic paradigm with cutting-edge technologies, theranostic agents are able to simultaneously deliver therapeutic drugs and diagnostic imaging agents and also monitor the response to therapy. Polymeric nanosystems have been intensively explored for biomedical applications to diagnose and treat various cancers. In recent years, glycol chitosan-based nanoagents have been developed as dual-purpose materials for simultaneous diagnosis and therapy. They have shown great potential in cancer therapies, such as chemotherapeutics and nucleic acid and photodynamic therapies. In this review, we summarize the recent progress and potential applications of glycol chitosan-based fluorescent theranostic nanoagents for cancer treatments and discuss their possible underlying mechanisms. Full article
(This article belongs to the Special Issue Advances in Marine Chitin and Chitosan) Printed Edition available
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Open AccessArticle Secocrassumol, a seco-Cembranoid from the Dongsha Atoll Soft Coral Lobophytum crassum
Mar. Drugs 2014, 12(12), 6028-6037; https://doi.org/10.3390/md12126028
Received: 16 October 2014 / Revised: 7 November 2014 / Accepted: 28 November 2014 / Published: 17 December 2014
Cited by 7 | PDF Full-text (504 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Chemical investigations on the Dongsha Atoll soft coral Lobophytum crassum led to the purification of a new seco-cembranoid, secocrassumol. The structural elucidation was established by extensive NMR, HRESIMS and CD data. The absolute configuration at C-12 was determined as S using a
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Chemical investigations on the Dongsha Atoll soft coral Lobophytum crassum led to the purification of a new seco-cembranoid, secocrassumol. The structural elucidation was established by extensive NMR, HRESIMS and CD data. The absolute configuration at C-12 was determined as S using a modified Mosher’s acylation. Secocrassumol differs from previously known marine seco-cembranoid in that it possesses an unprecedented skeleton functionalized at C11-C12 bond cleavage. Secocrassumol showed antiviral activity against human cytomegalovirus (HCMV) with an IC50 value of 5.0 μg/mL. Full article
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Open AccessReview Nano- and Microdelivery Systems for Marine Bioactive Lipids
Mar. Drugs 2014, 12(12), 6014-6027; https://doi.org/10.3390/md12126014
Received: 11 October 2014 / Revised: 24 November 2014 / Accepted: 28 November 2014 / Published: 17 December 2014
Cited by 6 | PDF Full-text (530 KB) | HTML Full-text | XML Full-text
Abstract
There is an increasing body of evidence of the positive impact of several marine lipids on human health. These compounds, which include ω-3 polyunsaturated fatty acids, have been shown to improve blood lipid profiles and exert anti-inflammatory and cardioprotective effects. The high instability
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There is an increasing body of evidence of the positive impact of several marine lipids on human health. These compounds, which include ω-3 polyunsaturated fatty acids, have been shown to improve blood lipid profiles and exert anti-inflammatory and cardioprotective effects. The high instability of these compounds to oxidative deterioration and their hydrophobicity have a drastic impact in their pharmacokinetics. Thus, the bioavailability of these compounds may be affected, resulting in their inability to reach the target sites at effective concentrations. In this regard, micro/nanoparticles can offer a wide range of solutions that can prevent the degradation of targeted molecules, increase their absorption, uptake and bioavailability. In this work we will present the options currently available concerning micro- and nanodelivery systems for marine lipids; with emphasis on micro/nanoparticles; such as micro/nanocapsules and emulsions. A wide range of bottom-up approaches using casein, chitosan, cyclodextrins, among others; will be discussed. Full article
(This article belongs to the Special Issue Marine Functional Food Products - Cardiovascular Diseases)
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Open AccessArticle Aaptamine Derivatives with Antifungal and Anti-HIV-1 Activities from the South China Sea Sponge Aaptos aaptos
Mar. Drugs 2014, 12(12), 6003-6013; https://doi.org/10.3390/md12126003
Received: 15 October 2014 / Revised: 3 November 2014 / Accepted: 2 December 2014 / Published: 16 December 2014
Cited by 8 | PDF Full-text (525 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Five new alkaloids of aaptamine family, compounds (15) and three known derivatives (68), have been isolated from the South China Sea sponge Aaptos aaptos. The structures of all compounds were unambiguously elucidated by spectroscopic
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Five new alkaloids of aaptamine family, compounds (15) and three known derivatives (68), have been isolated from the South China Sea sponge Aaptos aaptos. The structures of all compounds were unambiguously elucidated by spectroscopic analyses, as well as by comparison with the literature data. Compounds 12 are characterized with triazapyrene lactam skeleton, whereas compounds 45 share an imidazole-fused aaptamine moiety. These compounds were evaluated in antifungal and anti-HIV-1 assays. Compounds 3, 7, and 8 showed antifungal activity against six fungi, with MIC values in the range of 4 to 64 μg/mL. Compounds 78 exhibited anti-HIV-1 activity, with inhibitory rates of 88.0% and 72.3%, respectively, at a concentration of 10 μM. Full article
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Open AccessArticle Three New Asperentin Derivatives from the Algicolous Fungus Aspergillus sp. F00785
Mar. Drugs 2014, 12(12), 5993-6002; https://doi.org/10.3390/md12125993
Received: 21 October 2014 / Revised: 21 November 2014 / Accepted: 4 December 2014 / Published: 15 December 2014
Cited by 6 | PDF Full-text (582 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new asperentin-type compounds, 6-O-α-d-ribosylasperentin (1) and 6-O-α-d-ribosyl-8-O-methylasperentin (2) and 5-hydroxyl-6-O-methylasperentin (3), along with asperentin (4) and its known analogues (59), were isolated
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Three new asperentin-type compounds, 6-O-α-d-ribosylasperentin (1) and 6-O-α-d-ribosyl-8-O-methylasperentin (2) and 5-hydroxyl-6-O-methylasperentin (3), along with asperentin (4) and its known analogues (59), were isolated from a halotolerant Aspergillus sp. strain F00785, an endotrophic fungus from marine alga. Their structures were determined using extensive NMR and HRESIMS spectroscopic analysis, including the X-ray crystallographic data for the assignment of the absolute configurations of compound 9. Compound 4 exhibited highly potent inhibitory activity against crop pathogens, Colletotrichum gleosporioides Penz. and Colletotrichum gleosporioides (Penz.) Sacc. Full article
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