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1.
The pressurized liquid extraction (PLE) technique was used to obtain protein extracts with antioxidant capacity from salmon muscle remains, heads, viscera, skin, and tailfins. A protein recovery percentage ≈28% was obtained for all samples except for viscera, which was ≈92%. These values represented an increase of 1.5–4.8-fold compared to stirring extraction (control). Different SDS-PAGE profiles in control and PLE extracts revealed that extraction conditions affected the protein molecular weight distribution of the obtained extracts. Both TEAC (Trolox equivalent antioxidant capacity) and ORAC (oxygen radical antioxidant capacity) assays showed an outstanding antioxidant activity for viscera PLE extract. Through liquid chromatography coupled with electrospray ionization triple time-of-flight (nanoESI qQTOF) mass spectrometry, 137 and 67 peptides were identified in control and PLE extracts from salmon viscera, respectively None of these peptides was found among the antioxidant peptides inputted in the BIOPEP-UMP database. However, bioinformatics analysis showed several antioxidant small peptides encrypted in amino acid sequences of viscera extracts, especially GPP (glycine-proline-proline) and GAA (glycine-alanine-alanine) for PLE extracts. Further research on the relationship between antioxidant activity and specific peptides from salmon viscera PLE extracts is required. In addition, the salmon side streams studied presented non-toxic levels of As, Hg, Cd, and Pb, as well as the absence of mycotoxins or related metabolites. Overall, these results confirm the feasible use of farmed salmon processing side streams as alternative sources of protein and bioactive compounds for human consumption.  相似文献   

2.
Fishery by-products are rich in biologically active substances and the use of green and efficient extraction methods to recover these high-added-value compounds is of particular importance. In this study, head, skin and viscera of rainbow trout and sole were used as the target matrices and accelerated solvent extraction (ASE) (45–55 °C, 15 min, pH 5.2–6.8, 103.4 bars) and pulsed electric fields (PEF) (1–3 kV/cm, 123–300 kJ/kg, 15–24 h) were applied as extraction technologies. The results showed that ASE and PEF significantly increased the protein extract efficiency of the fish by-products (p < 0.05) by up to 80%. SDS-PAGE results showed that ASE and PEF treatments changed the molecular size distribution of the protein in the extracts, which was specifically expressed as the change in the area or number of bands between 5 and 250 kDa. The antioxidant capacity of the extracts was evaluated by oxygen radical absorbance capacity (ORAC) and total antioxidant capacity (ABTS) assays. The results showed that both ASE and PEF treatments significantly increased the antioxidant capacity of rainbow trout and sole skin and head extracts (p < 0.05). ASE and PEF extraction processes can be used as new technologies to extract high-added-value compounds from fish by-products.  相似文献   

3.
4.
This study shows a pilot scale protocol aimed to obtain an omega 3-enriched oil after the processing of farmed gilthead sea bream viscera (SBV); this was oil was tested in vitro for bioactivity, attesting to the possibility to turn waste into profit The quality of the oil, in terms of requirements for animal and human consumption, was assessed by determining some chemical parameters, such as peroxide value (PV), thiobarbituric acid reactive substances (TBARS), ρ-anisidine (ρ-AV) content, total oxidation value (TOTOX), and phospholipids and free fatty acid (%), both in crude viscera oil (CVO) and refined viscera oil (RVO). Among the extraction conditions, the higher CVO yields were obtained at 60 °C for 10 min (57.89%) and at 80 °C for 10 min (67.5%), and the resulting oxidation levels were low when utilizing both extraction conditions. RVO, obtained from CVO extracted at 60 °C, showed the highest quality on the basis of the assessed parameters. The ethyl esters of the total fatty acid (TFA) contents extracted from RVO were enriched in the ω-3 polyunsaturated fatty acid fraction (PUFAE) up to almost 56% via short path distillation (SPD). Antioxidant activities and adipogenic properties were tested in vitro. PUFAE protected 3T3 L1 cells from oxidative stress and exerted an anti-adipogenic effect in Dicentrarchus labrax pre-adipocytes, attesting to the beneficial properties for both farmed fish and human health. These results could stimulate the adoption of solutions aimed to recover and utilize aquaculture by-products at a higher scale, turning “waste into profit” and indicating a strategy to reach more sustainable business models in aquaculture resource utilization according to the principles of the circular economy.  相似文献   

5.
Turbo cornutus, the horned turban sea snail, is found along the intertidal and basaltic shorelines of Jeju Island, Korea. T. cornutus feeds on seaweeds (e.g., Undaria sp., and Ecklonia sp.) composed of diverse antioxidants. This study identified potential antioxidant properties from T. cornutus viscera tissues. Diverse extracts were evaluated for their hydrogen peroxide (H2O2) scavenging activities. T. cornutus viscera protamex-assisted extracts (TVP) were purified by gel filtration chromatography (GFC), and potential antioxidant properties were analyzed for their amino acid sequences and its peroxidase inhibition effects by in silico molecular docking and in vitro analysis. According to the results, T. cornutus viscera tissues are composed of many protein contents with each over 50%. Among the extracts, TVP possessed the highest H2O2 scavenging activity. In addition, TVP-GFC-3 significantly decreased intracellular reactive oxygen species (ROS) levels and increased cell viability in H2O2-treated HepG2 cells without cytotoxicity. TVP-GFC-3 comprises nine low molecular bioactive peptides (ELR, VGPQ, TDY, ALPHA, PAH, VDY, WSDK, VFSP, and FAPQY). Notably, the peptides dock to the active site of the myeloperoxidase (MPO), especially TDY and FAPQY showed the MPO inhibition effects with IC50 values of 646.0 ± 45.0 µM and 57.1 ± 17.7 µM, respectively. Altogether, our findings demonstrated that T. cornutus viscera have potential antioxidant properties that can be used as high value-added ingredients.  相似文献   

6.
To develop greener extraction alternatives for microalgae biomass, ultrasound assisted extraction (UAE) and pressurized liquid extraction (PLE) with different biobased solvents were investigated, demonstrating that both techniques are useful alternatives for algal lipid extraction. Specifically, Nannochloropsis gaditana lipids were extracted by UAE and PLE at different temperatures and extraction times with sustainable solvents like 2-Methyltetrahydrofuran (2-MeTHF) and its mixtures with ethanol and other alcohols. The best oil yields for both PLE and UAE of N. gaditana were achieved with the mixture of 2-MeTHF:ethanol (1:3), reaching yields of up to 16.3%, for UAE at 50 °C and up to 46.1% for PLE at 120 °C. Lipid composition of the extracts was analyzed by HPLC-ELSD and by GC-MS to determine lipid species and fatty acid profile, respectively. Different fractionation of lipid species was achieved with PLE and solvent mixtures of different polarity. Thus, for the extraction of glycolipids, ethanolic extracts contained higher amounts of glycolipids and EPA, probably due to the higher polarity of the solvent. The optimized method was applied to microalgae Isochrysis galbana and Tetraselmis chuii showing the potential of mixtures of biobased solvents like 2-methyl-THF and ethanol in different proportions to efficiently extract and fractionate lipids from microalgal biomass.  相似文献   

7.
This study aims to explore novel extraction technologies (ultrasound-assisted extraction (UAE), microwave-assisted extraction (MAE), ultrasound–microwave-assisted extraction (UMAE), hydrothermal-assisted extraction (HAE) and high-pressure-assisted extraction (HPAE)) and extraction time post-treatment (0 and 24 h) for the recovery of phytochemicals and associated antioxidant properties from Fucus vesiculosus and Pelvetia canaliculata. When using fixed extraction conditions (solvent: 50% ethanol; extraction time: 10 min; algae/solvent ratio: 1/10) for all the novel technologies, UAE generated extracts with the highest phytochemical contents from both macroalgae. The highest yields of compounds extracted from F. vesiculosus using UAE were: total phenolic content (445.0 ± 4.6 mg gallic acid equivalents/g), total phlorotannin content (362.9 ± 3.7 mg phloroglucinol equivalents/g), total flavonoid content (286.3 ± 7.8 mg quercetin equivalents/g) and total tannin content (189.1 ± 4.4 mg catechin equivalents/g). In the case of the antioxidant activities, the highest DPPH activities were achieved by UAE and UMAE from both macroalgae, while no clear pattern was recorded in the case of FRAP activities. The highest DPPH scavenging activities (112.5 ± 0.7 mg trolox equivalents/g) and FRAP activities (284.8 ± 2.2 mg trolox equivalents/g) were achieved from F. vesiculosus. Following the extraction treatment, an additional storage post-extraction (24 h) did not improve the yields of phytochemicals or antioxidant properties of the extracts.  相似文献   

8.
Given the pivotal role of Platelet-Activating-Factor (PAF) in atherosclerosis and the cardio-protective role of PAF-inhibitors derived from olive pomace, the inclusion of olive pomace in fish feed has been studied for gilthead sea bream (Sparus aurata). The aim of the current research was to elucidate the anti-atherogenic properties of specific HPLC lipid fractions obtained from olive pomace, olive pomace enriched fish feed and fish fed with the olive pomace enriched fish feed, by evaluating their in vitro biological activity against washed rabbit platelets. This in vitro study underlines that olive pomace inclusion in fish feed improves the nutritional value of both fish feed and fish possibly by enriching the marine lipid profile of gilthead sea bream (Sparus aurata) with specific bioactive lipid compounds of plant origin.  相似文献   

9.
The sea cucumber, Cucumaria frondosa, is harvested primarily for its muscular bands and body wall. Development of a nutraceutical product based on lipid recovered from its viscera would give commercial value to the entire organism; however, such development requires knowledge of the lipid and fatty acid (FA) profiles of the viscera. Here, we describe the lipid and FA composition of viscera recovered from C. frondosa harvested in coastal waters in the northwest Atlantic, taking into account variation due to harvest season. We found highest lipid content at ~29% in winter, with diacylglyceryl ethers (DAGE) comprising ~55% of the total lipid mass and triacylglycerols (TAG), phospholipids (PL) and monoacylglycerol ethers (MAGE) at 5–25% each. The branched chain FA, 12-methyltetradecanoic acid (12-MTA), represented 42% of total FA mass in DAGE. In summer, lipid content was lower at 24% and TAG was the dominate lipid, with proportions more than double that found in winter (45% vs. 20%); DAGE in summer dropped to ~30% of total lipids. In TAG, 12-MTA was much lower than found in DAGE in winter, at only 10% but eicosapentaenoic acid (EPA) content was ~20%, which brought the total EPA% to 28% of total FA—the highest among all three seasons. There was little effect of season on MAGE or PL proportions. These data can help harvesters maximize catch efforts in terms of lipid yield and profile.  相似文献   

10.
Marine algae are recognised sources of bioactive compounds that have attracted great interest as nutritional supplements for aquaculture fish. Intensive rearing conditions often expose fish to husbandry-related stressors, rendering fish more susceptible to disease and reducing production yields. The present work evaluated the potential of two marine algae extracts (Fucus vesiculosus and Nannochloropsis gaditana) as nutritional supplements to mitigate stress effects in meagre (Argyrosomus regius) exposed to an acute handling stress (AS). A plant-based diet was used as a control, and three other diets were prepared, which were similar to the control diet but supplemented with 1% of each algal extract or a combination of the two extracts (0.5% each). The effects of supplemented diets on stress biomarkers, antioxidant enzyme activities, and immune response were analysed in fish exposed to AS after 4 weeks of feeding. Supplemented diets did not affect growth performance but the inclusion of F. vesiculosus promoted higher feed efficiency, as compared to the control group. Dietary algal extracts supplementation reduced plasma glucose levels, increased white blood cell counts, and reduced the expression of pro-inflammatory genes when compared with the control. N. gaditana supplementation led to a reduction in hepatic antioxidant enzyme activity and glutathione levels, while F. vesiculosus supplementation increased muscle glutathione reductase activity and reduced lipid peroxidation. These findings support the potential of algal extracts as nutraceuticals in aquafeeds to enhance the ability of fish to cope with husbandry-related stressful conditions and ultimately improve fish health and welfare.  相似文献   

11.
Codium fragile and Chondrus crispus are, respectively, green and red seaweeds which are abundant along the North Atlantic coasts. We investigated the chemical composition and antiviral activity of enzymatic extracts of C. fragile (CF) and C. crispus (CC). On a dry weight basis, CF consisted of 11% protein, 31% neutral sugars, 0.8% sulfate, 0.6% uronic acids, and 49% ash, while CC contained 27% protein, 28% neutral sugars, 17% sulfate, 1.8% uronic acids, and 25% ash. Enzyme-assisted hydrolysis improved the extraction efficiency of bioactive materials. Commercial proteases and carbohydrases significantly improved (p ≤ 0.001) biomass yield (40%–70% dry matter) as compared to aqueous extraction (20%–25% dry matter). Moreover, enzymatic hydrolysis enhanced the recovery of protein, neutral sugars, uronic acids, and sulfates. The enzymatic hydrolysates exhibited significant activity against Herpes simplex virus (HSV-1) with EC50 of 77.6–126.8 μg/mL for CC and 36.5–41.3 μg/mL for CF, at a multiplicity of infection (MOI) of 0.001 ID50/cells without cytotoxity (1–200 μg/mL). The extracts obtained from proteases (P1) and carbohydrases (C3) were also effective at higher virus MOI of 0.01 ID50/cells without cytotoxity. Taken together, these results indicate the potential application of enzymatic hydrolysates of C. fragile and C. crispus in functional food and antiviral drug discovery.  相似文献   

12.
The effects of three independent variables: solvent polarity, temperature and extraction time on the antioxidant capacity, total phenolic content and phenolic acid composition in extracts obtained from sunflower shells before and after enzymatic treatment were studied. Response surface methodology based on three-level, three-variable Box-Behnken design was used for optimization of extraction parameters and evaluation of their effect on antioxidant capacity and total phenolic content in shell extracts.The average antioxidant capacities of extracts from sunflower shells without enzymatic treatment (368.1-1574.4 μmol TE/100 g) were higher than those for cellulolytic and pectolytic enzymes-treated shells (222.7-1419.0 and 270.7-1570.7 μmol TE/100 g, respectively). The content of total phenolic compounds ranged between 58.2-341.2 mg CGA/100 g, 26.7-277.3 mg CGA/100 g and 51.4-301.5 mg CGA/100 g for extracts obtained from shells without enzyme and treated with cellulolytic and pectolytic enzymes, respectively. Total phenolic content (TPC) in the studied shell extracts correlated significantly (p < 0.0001) positively with their antioxidant capacity determined by the ferric reducing antioxidant power (FRAP) method (r = 0.9275). Results of FRAP, TPC and phenolic acid composition in the studied shell extracts depend on the extraction conditions (solvent polarity, temperature, time), but they are independent on the addition of enzyme solutions. The antioxidant capacity and total phenolic content in the resulting extracts increased with a line in extraction temperature and solvent polarity.  相似文献   

13.
The recovery of amino acids and other important bioactive compounds from the comb penshell (Atrina pectinata) using subcritical water hydrolysis was performed. A wide range of extraction temperatures from 140 to 290 °C was used to evaluate the release of proteins and amino acids. The amount of crude protein was the highest (36.14 ± 1.39 mg bovine serum albumin/g) at 200 °C, whereas a further increase in temperature showed the degradation of the crude protein content. The highest amount of amino acids (74.80 mg/g) was at 230 °C, indicating that the temperature range of 170–230 °C is suitable for the extraction of protein-rich compounds using subcritical water hydrolysis. Molecular weights of the peptides obtained from comb penshell viscera decreased with the increasing temperature. SDS-PAGE revealed that the molecular weight of peptides present in the hydrolysates above the 200 °C extraction temperature was ≤ 1000 Da. Radical scavenging activities were analyzed to evaluate the antioxidant activities of the hydrolysates. A. pectinata hydrolysates also showed a particularly good antihypertensive activity, proving that this raw material can be an effective source of amino acids and marine bioactive peptides.  相似文献   

14.
Sargassum brown seaweed is reported to exhibit several biological activities which promote human health, such as anticancer, antimicrobial, antidiabetic, anti-inflammatory, and antioxidant activity. This study aimed to investigate the anti-inflammatory and antioxidant activity of crude lipid extracts of Sargassum ilicifolium obtained from four different coastal areas in Indonesia, namely Awur Bay–Jepara (AB), Pari Island–Seribu Islands (PI), Sayang Heulang Beach–Garut (SHB), and Ujung Genteng Beach–Sukabumi (UGB). Results showed that treatment of RAW 264.7 macrophage cells with UGB and AB crude lipid extracts (12.5–50 µg/mL) significantly suppressed the nitric oxide production after lipopolysaccharide stimulation, both in pre-incubated and co-incubated cell culture model. The anti-inflammatory effect was most marked in the pre-incubated cell culture model. Both two crude lipid extracts showed 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity and high ferric reducing antioxidant power, which were amounted to 36.93–37.87 µmol Trolox equivalent/g lipid extract and 681.58–969.81 µmol FeSO4/g lipid extract, respectively. From this study, we can conclude that crude lipid extract of tropical S. ilicifolium can be further developed as a source of anti-inflammatory and antioxidant agent.  相似文献   

15.
The methanol and ethyl acetate (EA) extracts of four species of sea lily (Himerometra magnipinna, Comaster multifidus, Comanthina sp., and Comatella maculata) were evaluated for their insecticidal activity against Yellow-fever mosquito larvae (Aedes aegypti) and their repellency against adult Asian Tiger mosquitoes (Aedes albopictus). The 24-hr minimum inhibition concentration (MIC) data revealed that the extracts from H. magnipinna and the C. maculata were the most active, killing mosquito larvae at 12.5 ppm. The toxicity of the extracts from these four sea lilies in descending order was H. magnipinna (12.5 ppm), C. maculata (12.5 ppm), C. multifidus (100 ppm), and Comanthina sp. (200 ppm). Furthermore, no significant difference in toxicity was found using either EA or methanol as the extraction solvent. The MIC at 12.5 ppm is promising as an insecticide lead. The repellency study results show that EA is a better solvent for one species (H. magnipinna), but the methanol is a better solvent overall. The repellency of these sea lily extracts in descending order was Comanthina sp. MeOH (ED50 at 0.32%), followed by H. magnipinna EA (ED50 at 0.38%), C. multifidus MeOH (ED50 at 0.57%), C. maculata MeOH (ED50 at 0.76%), C. multifidus EA (ED50 at 1.25%), and H. magnipinna MeOH (ED50 at 1.67%). A compound with ED50 <0.5% is considered to be a promising repellant. Among the studied sea lilies, both Comanthina sp. and H. magnipinna have potential to be further developed as mosquito control agents due to their favorable toxicity and repellency.  相似文献   

16.
Green extraction was applied to Argentinean shortfin squid (Illex argentinus) viscera, consisting of a wet pressing method including a drying step, mechanic pressing, centrifugation of the resulting slurry, and oil collection. To maximise the oil yield and ω3 fatty acid content and to minimise the oil damage degree, a response surface methodology (RSM) design was developed focused on the drying temperature (45–85 °C) and time (30–90 min). In general, an increase of the drying time and temperature provided an increase in the lipid yield recovery from the viscera. The strongest drying conditions showed a higher recovery than 50% when compared with the traditional chemical method. The docosahexaenoic and eicosapentaenoic acid contents in the extracted oil revealed scarce dependence on drying conditions, showing valuable ranges (149.2–166.5 and 88.7–102.4 g·kg−1 oil, respectively). Furthermore, the values of free fatty acids, peroxides, conjugated dienes, and ω3/ω6 ratio did not show extensive differences by comparing oils obtained from the different drying conditions. Contrary, a polyene index (PI) decrease was detected with increasing drying time and temperature. The RSM analysis indicated that optimised drying time (41.3 min) and temperature (85 °C) conditions would lead to 74.73 g·kg−1 (oil yield), 1.87 (PI), and 6.72 (peroxide value) scores, with a 0.67 desirability value.  相似文献   

17.
Microalgae are well known for their biotechnological potential, namely with regard to bioactive lipidic components—especially carotenoids and polyunsaturated fatty acids (PUFA), well-known for therapeutic applications based on their antioxidant capacity. The aim of this work was to evaluate the influence of four distinct food-grade solvents upon extractability of specific lipidic components, and on the antioxidant capacity exhibited against both synthetic (2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS+•)) and biological reactive species (O2 and NO). A eukaryotic microalga (Scenedesmus obliquus (M2-1)) and a prokaryotic one (Gloeothece sp.) were used as case studies. Concerning total antioxidant capacity, the hexane:isopropanol (3:2) and acetone extracts of Sc. obliquus (M2-1) were the most effective against DPPH and ABTS+•, respectively. Gloeothece sp. ethanol extracts were the most interesting scavengers of O2, probably due the high content of linolenic acid. On the other hand, acetone and hexane:isopropanol (3:2) extracts were the most interesting ones in NO assay. Acetone extract exhibited the best results for the ABTS assay, likely associated to its content of carotenoids, in both microalgae. Otherwise, ethanol stood out in PUFA extraction. Therefore, profiles of lipidic components extracted are critical for evaluating the antioxidant performance—which appears to hinge, in particular, on the balance between carotenoids and PUFAs.  相似文献   

18.
This study was aimed at investigating the effect of low polarity water (LPW) on the extraction of bioactive compounds from Fucus vesiculosus and to examine the influence of temperature on the extraction yield, total phenolic content, crude alginate, fucoidan content, and antioxidant activity. The extractions were performed at the temperature range of 120–200 °C with 10 °C increments, and the extraction yield increased linearly with the increasing extraction temperature, with the highest yields at 170–200 °C and with the maximum extraction yield (25.99 ± 2.22%) at 190 °C. The total phenolic content also increased with increasing temperature. The extracts showed a high antioxidant activity, measured with DPPH (2,2-Diphenyl-1-picrylhydrazyl) radicals scavenging and metal-chelating activities of 0.14 mg/mL and 1.39 mg/mL, respectively. The highest yield of alginate and crude fucoidan were found at 140 °C and 160 °C, respectively. The alginate and crude fucoidan contents of the extract were 2.13% and 22.3%, respectively. This study showed that the extraction of bioactive compounds from seaweed could be selectively maximized by controlling the polarity of an environmentally friendly solvent.  相似文献   

19.
Caulerpa racemosa (sea grapes) and Ulva lactuca (sea lettuces) are edible green seaweeds and good sources of bioactive compounds for future foods, nutraceuticals and cosmeceutical industries. In the present study, we determined nutritional values and investigated the recovery of bioactive compounds from C. racemosa and U. lactuca using hot water extraction (HWE) and subcritical water extraction (SWE) at different extraction temperatures (110 to 230 °C). Besides significantly higher extraction yield, SWE processes also give higher protein, sugar, total phenolic (TPC), saponin (TSC), flavonoid contents (TFC) and antioxidant activities as compared to the conventional HWE process. When SWE process was applied, the highest TPC, TSC and TFC values were obtained from U. lactuca hydrolyzed at reaction temperature 230 °C with the value of 39.82 ± 0.32 GAE mg/g, 13.22 ± 0.33 DE mg/g and 6.5 ± 0.47 QE mg/g, respectively. In addition, it also showed the highest antioxidant activity with values of 5.45 ± 0.11 ascorbic acid equivalents (AAE) mg/g and 8.03 ± 0.06 trolox equivalents (TE) mg/g for ABTS and total antioxidant, respectively. The highest phenolic acids in U. lactuca were gallic acid and vanillic acid. Cytotoxic assays demonstrated that C. racemosa and U. lactuca hydrolysates obtained by HWE and SWE did not show any toxic effect on RAW 264.7 cells at tested concentrations after 24 h and 48 h of treatment (p < 0.05), suggesting that both hydrolysates were safe and non-toxic for application in foods, cosmeceuticals and nutraceuticals products. In addition, the results of this study demonstrated the potential of SWE for the production of high-quality seaweed hydrolysates. Collectively, this study shows the potential of under-exploited tropical green seaweed resources as potential antioxidants in nutraceutical and cosmeceutical products.  相似文献   

20.
Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was collected at a depth of 45 m. Chemical fractionation followed by detailed spectroscopic analysis led to the discovery of a new tryptophan-derived alkaloid, thorectandrin A (1), with the GNPS cluster revealing a halo of related alkaloids 1a–1n. In considering biosynthetic origins, we propose that Thorectandra choanoides (CMB-01889) produces four well-known alkaloids, 6-bromo-1′,8-dihydroaplysinopsin (2), 6-bromoaplysinopsin (3), aplysinopsin (4), and 1′,8-dihydroaplysinopsin (10), all of which are susceptible to processing by a putative indoleamine 2,3-dioxygenase-like (IDO) enzyme to 1a–1n. Where the 1′,8-dihydroalkaloids 2 and 10 are fully transformed to stable ring-opened thorectandrins 1 and 1a–1b, and 1h–1j, respectively, the conjugated precursors 3 and 4 are transformed to highly reactive Michael acceptors that during extraction and handling undergo complete transformation to artifacts 1c–1g, and 1k–1n, respectively. Knowledge of the susceptibility of aplysinopsins as substrates for IDOs, and the relative reactivity of Michael acceptor transformation products, informs our understanding of the pharmaceutical potential of this vintage marine pharmacophore. For example, the cancer tissue specificity of IDOs could be exploited for an immunotherapeutic response, with aplysinopsins transforming in situ to Michael acceptor thorectandrins, which covalently bind and inhibit the enzyme.  相似文献   

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