Enantioselective total synthesis of macrosphelides A and E

Enantioselective synthesis of 16-membered trilactone macrolides, macrosphelide A and E from (S)-lactic acid is described. Key features of the synthesis include the utility of a hitherto unexplored beta-ketophosphonate derived from lactic acid and Yamaguchi lactonization leading to the title compounds. (C) 2011 Elsevier Ltd. All rights reserved.

Total synthesis and determination of the absolute configuration of 5,6-Dihydro-alpha-pyrone natural product synargentolide B

Enantiospecific total synthesis and determination of the absolute stereochemistry of the alpha-pyrone-containing natural product synargentolide B were accomplished. The absolute stereochemistry of the natural product was established by synthesizing the possible diastereomers and comparison of the data with those reported for the natural product. During the process, total synthesis of the putative structure of related natural product 6R-1S,2R,SR,6S-(tetraacetyloxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-o ne was also accomplished and confirmed by X-ray crystal structure analysis. Wittig-Horner reaction of a chiral phosphonate derived from (S)-lactic acid and ring-closing metathesis were the key reactions during the course of the total synthesis.

Enantiospecific total synthesis of indole alkaloids (+)-eburnamonine, (-)-aspidospermidine and (-)-quebrachamine

An enantiospecific total synthesis of indole alkaloids eburnamonine, aspidospermidine and quebrachamine is described from lactic acid. Synthesis of all three alkaloids is accomplished from a single chiral building block. Johnson-Claisen rearrangement of a chiral allyl alcohol is the main feature for the installation of the required quaternary centre.

Comportamiento prooxidante y antioxidante de hierbas aromáticas en queso

Los quesos de cabra, con mejores cualidades funcionales provienen de leche de cabras en pastoreo, esto obedece al mayor contenido de ácidos grasos ω-3 y ω-6 en una relación óptima para la salud, sumado a un menor contenido de grasa y colesterol. Saborizar quesos con especias, otorga beneficios sensoriales y saludables al producto. Las especias son usadas para realzar el flavor de los alimentos además presentan beneficios antioxidantes. Sin embargo, se reportaron evidencias del doble papel de los flavonoides como antioxidantes o prooxidantes en función de la concentración de uso. El objetivo del trabajo es evaluar el efecto de distintas concentraciones de especias aromáticas con capacidad antioxidante, frente a las reacciones de deterioro que ocurren en el almacenamiento de quesos de cabra. Se estudió la actividad antirradicalaria (AAR) de 18 especias. Para evaluar la actividad antioxidante (AA0) se usó la técnica de desaparición de un radical libre estable el 2,2-difenil-1-picril hidrazilo (DPPH) y se calculó la AAR porcentual. Definido el queso base estándar (control), se ensayaron tres variedades con especies, elegidas de entre las de mayor AAR (orégano, romero y tomillo) y se adicionaron con las concentraciones 0,4 – 1 % p/p. Estos, fueron madurados 30 días y almacenados 7 meses a 4 °C. Se analizaron cada 4 semanas. Se realizaron pruebas sensoriales de aceptabilidad con 60 consumidores de queso (condición), usando planillas, con escala hedónica. Se trabajó sobre los lípidos extraídos de los quesos. El rancidez y deterioro fueron evaluados con análisis de acidez; índice peróxido y sustancias reactivas al ácido TBA. Los resultados se compararon con el comportamiento sensorial del producto en el tiempo de almacenamiento. En los quesos adicionados al 1 %, la acidez se incrementó con el almacenamiento. El máximo valor corresponde al queso con orégano (3,72 % de ac. láctico a los 126 días). En el control, la acidez inicial fue inferior y alcanzó 1,05 g de ác. láctico % a los 166 días. El IP más alto corresponde a los quesos con orégano al 1% , resultado que se contrapone a la actividad antirradicalaria de esta especia. Al 0,4 %, tanto el IP como el número de TBA son menores en quesos adicionados, respecto del control. En los quesos de cabra analizados las especias agregadas al 1% ejercieron acción prooxidante, mientras que al ser agregadas al 0,4% la acción es antioxidante, lo que indica la importancia de la selección de concentraciones adecuadas.

Alterações em genes relacionados à via glicolítica em tumores de carcinoma epidermoide de esôfago

O carcinoma epidermoide de esôfago (CEE) representa 90% dos casos de câncer de esôfago no Brasil. O CEE tem detecção tardia, um comportamento extremamente agressivo e baixa sobrevida, sendo, portanto, um alvo interessante para o estudo dos mecanismos envolvidos em sua carcinogênese, a fim de se identificar possíveis alvos terapêuticos ou marcadores moleculares que ajudem na prática clínica. Mudanças no metabolismo energético da célula tumoral parecem ter papel de destaque na transformação maligna. Sabe-se que células tumorais consomem glicose avidamente produzindo ácido lático, mesmo em condições de normóxia. Dentre os fatores que podem contribuir para o estímulo da glicólise em células tumorais destacam-se as alterações em enzimas da via glicolítica tais como: as piruvato-cinases M1 e M2 (PKM1 e PKM2), a hexocinase II (HKII), isofoma 1 do transportador de glicose, GLUT-1, e o fator de transcrição induzido por hipóxia (HIF1α), responsável pela transcrição das proteínas citadas. O objetivo do estudo é avaliar a relação entre a expressão de HIF1α, HK2, PKM2, PKM1 e GLUT-1 e dados clínico-patológicos no CEE. Para tal, foram avaliados tumores conservados em parafina de 44 pacientes com CEE matriculados no INCA e no Hospital das Clínicas de Porto Alegre. Além disso, foram coletadas amostras de biópsia de esôfago em 67 pacientes sem doença esofágica, que foram submetidos à endoscopia no Hospital Universitário Pedro Ernesto (HUPE). A expressão das proteínas foi avaliada nos tecidos por imuno-histoquímica, enquanto que a expressão do mRNA de GLUT-1 também foi avaliada nas amostras controle. Foi observado que as amostras controle expressam HK2, PKM1, PKM2, HIF1α nas camadas do epitélio esofágico. Já GLUT-1 e Ki-67 são vistos apenas na camada basal. Além disso, a expressão do mRNA de GLUT-1 não teve correlação com fatores etiológicos da doença. Em CEE a expressão de HK2, PKM2 e GLUT-1 foi vista em todos os tumores, já a expressão de HIF1α e PKM1 foi variável. Além disso, observou-se que maior expressão de HIF-1α apresenta correlação com invasão linfonodal e diferenciação, enquanto que a expressão de HK2 tem relação com sobrevida e PKM1 com diferenciação. As correlações clínicas encontradas sugerem que alterações no metabolismo energético é um alvo de estudo interessante para desenvolvimento de marcadores moleculares que auxiliem a prática clínica.

Evaluation of chemical tests for the quality of prawns

The object of this study was to determine the value of physical, bacteriological and chemical tests used to find out and compare the indices of quality of prawns stored at 0°C and at 18°C. pH value, nature of drip, the total bacterial count, presence or absence of tryptophan, trimethylamine content, glycogen, lactic acid, vitamins such as thiamin, riboflavin and niacin were estimated periodically to evaluate the quality of prawns stored at 0°C, whereas in addition to organoleptic changes, pH, bacterial count, nature of growth in peptone water, soluble protein in salt solution and loss of moisture, glycogen, lactic acid, and changes in vitamin B contents were noted periodically for prawns stored at -l8°C. Riboflavin and niacin were not affected appreciably but the retention of thiamin in prawns was very low.

Ensiled product from fish by microbial fermentation

Fish ensilage for animal feed stuff was prepared from Jew fish (Pseudosciaena spp.) and Silver bellies (Leiognathus spp.) by fermentation with pure culture of Lactobacillus piantarum NCIB 6105. The precooked ensiled product gave better product of fish silage (high content of lactic acid, about 5%). Protein Nitrogen content ranged between 1.76 to 1.94%. During storage for one year, the Protein Nitrogen loss was not significant. The material can be used as a supplemental animal ration.

Technological aspects of processing of edible mussels, clams and crabs. Pt. 1. Spoilage during ice storage

Rate and pattern of spoilage of some of the economically important edible species of shell fishes Mytilus edulis (Mussel), Villorita cornucopia (Clam), Neptunus pelagicus (Crab) and Scylla serrata (Crab) have been discussed in this communication. Chemical indices used for objective evaluation of quality were water extractable nitrogen (WEN), non-protein nitrogen (NPN), free α-amino nitrogen (α - NH2 -N), glycogen, lactic acid and inorganic phosphorus in addition to the subjective tests. No significant difference in the spoilage pattern of the species during ice storage was observed and these species could be preserved in ice in organoleptic acceptable condition up to 8 days, 9 days, 8 days and 11 days respectively.

Technological aspects of preservation and processing of edible shell fish 2. Influence of season on the chemical composition of crab (Scylla serrata)

The purpose of this communication is to bring out the influence of season on the chemical composition of crab, covering a period of 2 years. Changes in moisture, protein, water extractable nitrogen, non-protein nitrogen, glycogen, lactic acid, fat and free amino acid composition of crab meat have been reported on a monthly basis.

Pilot plant for production of fish ensilage and the economics of production

This communication describes the design aspect and functions of individual pieces of equipment of a pilot plant for the production of fish ensilage based on lactic acid fermentation process. Details about the equipment, process flow sheet and equipment layout of the pilot plant have been given. An attempt has been made to prepare an estimate of the cost of production of liquid ensilage and solid feed mix.

Studies on canning Psenopsis cyanea

Suitability of Psenopsis cyanea, a deep sea fish caught on board FORV Sagar Sampada from a depth of 350m off Cochin for processing into canned product was studied. The fish having high fat content around 52% (DWB) and white attractive meat renders itself well for canning yielding a product good in organoleptic characteristics. However to have a presentable appearance to the product the fish has to be skinned prior to canning. Gentle agitation of P. cyanea in 0.25% aqueous solution of lactic acid at ambient temperature for 15 min followed by thorough washing yields skinless fish. Fish suffers around 8% (DWB) fat loss during skinning. Fish canned in natural style and in brine have better organoleptic characteristics initially. On storage they develop slight rancidity. Fish canned in oil maintains the characteristics over a longer period.

Comparative effect of Pediococcus acidilactici and Lactococcus lactis on growth performance, survival and enzyme activity of western white leg shrimp (Litopenaeus vannamei)

This study was done in Shahid Kiani Marine Aquaculture Development Center, Choebde, Abadan in order to evaluate the effects of Pediiococcus acidilactici, Lactococcus lactis and vitamin C on growth performance, survival, enzymatic activities and immune responses of L. vannamei during three months. Treatments were included control group, Pediiococcus and Lactococcus treatments which fed with diet containing 1×10P9P cfu gP_1P bacteria and vitamin C. At the end of the experiment, the growth factors, immune parameters, digestive enzymes, intestinal, histology of intestine, carcasses and microbial flora (bacterial total count and lactic acid count) were evaluated. The results indicated that administration of lactobacillus had significant effects on the growth factors as the highest weight, increase specific growth rate, relative growth rate, feed conversion ratio and protein efficiency in the shrimps received pediococcus and then Lactococcus (P<0.05). The best immune function was also observed in the shrimps fed by probiotics, so that proteins and hemoglobin̛ hemolymph, phenoloxidase activity and challenged with V. parahaemolyticus showed a statistical difference comparing to the control group and the group received vitamin C (P<0.05). Some digestive enzymes, in pediococcus treatment showed a significant increase when compared to other treatments (P<0.05). Significant changes in bacterial intestinal flora were observed in probiotic groups compared with control and vitamin C groups (P < 0.05). Histological results showed the positive effects of probiotics in the gut (P < 0.05). While these supplements cannot caused to significant impacts on the shrimp carcass composition (P ˃ 0.05). As a result pediococcus group had the best performance among treatments.

Application of encapsulated nisin and sodium citrate for shelf life increasing of Rainbow trout (Onchorhynchus mykiss) fillet packaged with MAP and their effect on Staphylococcus aureus

Nisin is a widely used naturally occurring antimicrobial effective against many pathogenic and spoilage microorganisms. It has been proposed that reduced efficacy of nisin in foods can be improved by technologies such as encapsulation to protect it from interferences by food matrix components. The aim of this study was using of spray dried encapsulated nisin with zein in concentration of (0.15 and 0.25 g/kg) and sodium citrate (1.5 and 2.5%) and treatments with both of them to extent the shelf life of filleted trouts packaged by Modified Atmosphere Packaging (45% CO2, 50% N2 ,5% O2) and stored at 4±1 °C for 20 days. Furthermore, to evaluate the antimicrobial efficiency of encapsulated nisin and soudium citrate the trouts fillets was inoculated with Staphylococcus aureus as an index pathogenic bacteria. Assessment of chemical spoilage indexes such as (Proxide value, Thiobarbituric acid, total volatile base nitrogen and pH) , microbial parameters (Total Plate Count, Psychrotrophic count, Lactic acid bacteria count), Staphylococcus aureus cont in treatments which were inoculated with 5 logcfu/g of this bacteria and sensory evaluation of fillets including (smell, color, texture and total acceptability) was carried out in days of 0, 4, 8, 12, 16 and 20. The results revealed that treatment with both exposure of nisin and sodium citrate showed significantly lower chemical spoilage indexes in comparison with controls (vaccum packed and MAP) (P<0.05). Furthermore, (nisin 0.25 g/kg sodium citrate 2.5%) treatment which was exposed to the maximal level used of both materials was significantly the lowest treatment with (Proxide value, Thiobarbituric acid, total volatile base nitrogen and pH) of 9.95 (meq O2/kg) , 1.55 (mgMA/kg), 29.65 (mgN/100g) and 6.65 , respectively and according to the maximal recommended level of this indices , shelf life of fillets in this treatment was esstimated 20 days.The control (vaccum packed) treatment was significantly the highest treatment with (Proxide value, Thiobarbituric acid, total volatile base nitrogen and pH) of 15.17 (meq O2/kg), 3.03 (mgMA/kg), 38.4 (mgN/100g) and 6.95 , respectively and according to the maximal recommended level of this indices , shelf life of fillets in this treatment was estimated 11 days. Also, in microbial point of view (nisin 0.25 g/kg- sodium citrate 2.5%) treatment was the lowest treatment with Total Plate Count, Psychrotrophic count, Lactic acid bacteria count and Staphylococcus aureus count of 6.7, 6.83, 5.25 and 6.04 logcfu/g respectively, and conrol (vaccum packed) treatment was the highest treatment with 9.15, 9.41, 7.7 and 9.01 logcfu/g respectively. According to the lower results of chemical and microbial indices and higher sensory evaluated scores assessed in this research for encapsulated nisin in comparison with free nisin , it was concluded that encapsulation of nisin with zein capsules may improve the efficiency of nisin. The measuremented values of Mass yield, Total solids content of capsules, Encapsulation efficiency, In vitro release kinetics in 200 hour for encapsulated nisin in this study was 49.89, 62, 98.31 and 69% respectively and Encapsulated particle size was lower than 674.21 μm for 90% of particles. As a consequence, nisin , in particular encapsulated nisin, and sodium citrate alone or together with and Modified Atmosphere packaging might be considered as effective tools in preventing the quality degradation of the fillets, resulting in an extension of their shelf life.

Effect of dietary inulin as prebiotic on growth, survival and intestinal bacterial density of juvenile great sturgeon (Huso huso)

Use of prebiotics, nondigestible dietary ingredients that beneficially affect the host by selectively stimulating the growth of and/or activating the metabolism of healthpromoting bacteria in the intestinal tract, is a novel concept in aquaculture. An 8-week feeding experiment was conducted to investigate the effects of dietary prebiotic inulin on the growth performance, intestinal bacterial density, body composition and values of blood serum enzymes in the juvenile great sturgeon (Huso huso). Three replicate groups of fish (initially averaging weight 16.14±0.38g) were fed diets containing prebiotic inulin at levels ranging from 1% to 3%. The basal diet was contained 3% cellulose. The results of linear regression showed there was a negative relationship between some performance indices including weight gain (WG), specific growth rate (SGR), protein efficiency ratio (PER), net protein utilization (NPU), energy retention (ERE), feed efficincy (FE), protein retention (PR) and supplementation level of inulin. At the end of trial, the 1% inulin treatment insignificantly showed an enhaced survival between the treatment groups. Intestinal lactic acid bacteria (LAB) increased in group treated with 1% inulin compare to other groups. No significant difference were observed in body composition and level of serum enzymes (P>0.05). Moreover there was significant correlation between ALT and LDH values (P<0.01). Result obtained in this study shows that the prebiotic inulin didn’t influence the increase of the growth performance of juvenile great sturgeon and it is not appropriate for supplementation in the diet of beluga.

Study on effects of extracted probiotics from microbial flora of digestive system on growth indices in beluga (Huso huso) and Persian sturgeon (Acipenser persicus)

Isolation of Lactic Acid Bacteria (LAB) was carried out from gastro intestinal tract of beluga and Persian sturgeon at international sturgeon research institute and PCR has been used for bacteria Identification. Two species of LAB including Enterococcus seriolicida and Leuconostoc mesenteroides were isolated from Gastrointestinal tract (GI) of persian sturgeon in this study and the counts of Leu. mesenteroides (4.63×102 CFU/gr of GI) was significantly higher than other species. Lactobacillus curvatus, Lactococcus raffinolactis, Lactococcus lactis and Streptococcus sp. were also isolated from GI of beluga and maximum counts was belonged to Lb. curvatus (4.63×102 CFU/gr of GI) in this species. Dominant species were lyophilized and adding to the water since start of mix feeding of sturgeon with different counts including 2×109, 5×109 and 9×109 CFU/gr of live food, 4 times a day. The results revealed that the maximum and minimum growth rate and protease, amylase, and lipase activity in beluga was gained by using of Lb. curvatus with total viable count of 9×10 9 CFU/gr of live food and Leu. mesenteroides with total viable count of 9×109 CFU/gr of live food. According to the results of this study, the maximum and minimum growth rate and protease, amylase, and lipase activity in Persian sturgeon was gained by using of Leu. mesenteroides with total viable count of 2×10 9 CFU/gr of live food and Lb. curvatus with total viable count of 9×109 CFU/gr of live food. Histological study showed that gastrointestinal development was same during larva rearing in control and other treatments but the size of liver was bigger in treatments that received nonspecific LAB in both species. According to the results, positive effects of using dominant specific LAB bacteria for larviculture of sturgeon has been proved in this study.