Laurendecumallenes A-B and laurendecumenynes A-B, halogenated nonterpenoid C-15-Acetogenins from the marine red alga Laurencia decumbens

Four new halogenated nonterpenoid C-15-acetogenins, 4:7,6:13-bisepoxy-9,10-diol-1,12-dibromopentadeca-1,2-diene (1, laurendecumallene A), 4:7,6:12-bisepoxy-9,10-diol-1,13-dibromopentadeca-1,2-diene (2, laurendecumallene 13), (3Z)-6:10,7:13-bisepoxy-12-bromo-9-hydroperoxylpentadeca-3-en-1-yne (3, laurendecumenyne A), and (3Z)-6:10,9:13-bisepoxy-12-bromo-7-chloropentadeca-3-en-1-yne (4, laurendecumenyne 13), together with one known halogenated C-15-acetogenin elatenyne (5) were isolated and identified from the organic extract of the marine red alga Laurencia decumbens. Their structures and relative stereochemistry were established by means of spectroscopic analysis including UV, IR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and ID and 2D NMR techniques. All these metabolites were submitted for the cytotoxic assay against tumor cell line A549 (human lung adenocarcinoma), but all of them were found inactive (IC50 > 10 mu g/mL).

Two new brominated diterpenes from Laurencia decumbens

Two new brominated diterpenes, namely, laurendecumtriol and 11-deacetylpinnaterpene C, were isolated and identified from the marine red alga Laurencia decumbens. Their structures were established on the basis of various NMR spectroscopic techniques and HR-ESI-MS analyses. (c) 2007 Bing Gui Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

Terpenes and polybromoindoles from the marine red alga Laurencia decumbens (Rhodomelaceae)

Two new brominated diterpenes, namely, laurendecumtriol (1) and 11-O-deacetylpinnaterpene C (2), one new polybromoindole, 2,3,4,6-tetrabromo-1-methyl-1H-indole (7), and six known natural products were isolated and identified from the marine red alga Laurencia decumbens. Their structures were elucidated on the basis of detailed spectroscopic and mass-spectrometric analysis as well as by comparison with literature data. Based on 2D-NMR experiments, the previously reported NMR data for pinnaterpene C (3) were reassigned.

Urceolatin, a structurally unique bromophenol from Polysiphonia urceolata

6-Bromo-1-(3-bromo-4,5-dihydroxybenzyl)phenanthro[4,5-bcd]furan-2,3,5-triol (urceolatin, 1), a highly oxygenated bromophenol containing an unprecedented naturally occurring benzylphenanthro[4,5-bcd]furan unit, was isolated from the marine red alga Polysiphonia urceolata. Its structure was established on the basis of extensive spectroscopic analysis. Compound 1 displayed significant DPPH radical-scavenging activity with an IC50 value of 7.9 mu M, which is 10-fold more potent than that of the positive control, butylated hydroxytoluene.

Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae)

Four new halogenated sesquiterpenes, 10-bromo-3-chloro-2,7-epoxychamigr-9-en-8a-of (1), 2,10 beta-dibromochamigra-2,7-dien-9 alpha-ol (2), (9S)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (3), and (9R)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (4), were characterized from the marine red alga Laurencia saitoi. In addition, two known halosesquiterpenes, 2,10-dibromo-3-chlorochamigr-7-en-9 alpha-ol (5) and isolaurenisol (6), were also isolated and identified. Their structures were established on the basis of extensive analysis of spectroscopic data.

Highly Oxygenated Triterpenoids from the Marine Red Alga Laurencia mariannensis (Rhodomelaceae)

Two new and one known squalenoid-derived triterpenoids. namely, laurenmariannol (1) and (21 alpha)-21-hydroxythyrsiferol (2). and the known thyrsiferol (3) were isolated and identified from the marine red alga Laurencia mariannensis, which was collected off the coast of Hainan and Weizhou Islands of China. The structures of these compounds were established by means of spectroscopic analyses, as well as by comparison with literature data. Compounds I and 2 displayed significant cytotoxic activity against P-388 tumor cells with IC50 values of 0.6 and 6.6 mu g/ml, respectively.

Valor nutritivo del pasto pangola (Digitaria decumbens stent.) vr. transvala a distintos niveles de fertilización y diversas edades de corte

Este estudio Se desarrolló en el periodo de julio a diciembre de 1990 en el Centro de Investigación Zootecnia “La Polvosa” de la UCA (Universidad Centroamericana), situada en el km 23 112 de la carretera nueva a León, depto. de Managua. El centro se ubica a una elevación de 40 msnrn a 1 2 grados 12 minutos, Latitud norte y 86 grados 22 minutos, longitud oeste registra temperaturas promedio anuales de 32 grados centígrados los y unos 8OO mm de precipitación media por año, por lo cual, es posible calificar su zona agroecológica como de trópico seco se evaluó la respuesta en términos de valor nutritivo del pasto Pangola (Digitaria decumbens Stent.) vr. Transvala, utilizándose un diseño experimental en bloques completos al azar (BCA) con arreglo factorial, se estudió el efecto de dos factores (Niveles de fertilizantes-edades de cortes) con cuatro repeticiones, formándose un total de 16 tratamientos El ensayo contó con un área experimental total de 357.75 mt2 para la toma de muestras, se empleó el método del metro cuadrado realizándose en las parcelas un muestreo sin reemplazo para cada frecuencia en estudio. Previo al momento experimental, se efectúo una poda de control procediéndose después a aplicar de una sola vez los respectivos niveles de fertizante. El estudio estadístico contempló el uso del análisis de varianza (ANDEVA), se hizo una separción de medias por Tukey, y se midió la influencia porcentual (Individual y asociada) de 4 niveles de fertilizante (0, 50,100 y150 kg urea (46%N2) / mz) y 4 edades de corte (15, 30.. 45y 60 días), sobre nueve variables o componentes bromatológicos (MS, PB,FC, ELN, EE, EB (Kcal/ 100g), Cz, Ca y P). Todos los componentes bromatológicos evaluados excepto el EE.. presentaron una variación significativa (P<0.05), bajo el efecto de los factores en estudio. Los niveles de fertilizante influyeron ios valores de mayor mérito con la dosis •150 kg urea / rnz, observando la PB.. 9.76% ;el ELN, 56.54 y la EB,190.97 Kcal ,' 100 g. En tanto que los 50 kg1mz mostraron !os mayores índices en FC (28.88), EE (2.75) y Cz. (11.:39) las parcelas no fertilizadas brindaron los porcentajes más altos de MS (23.78) y Ca (0.60),y el nivel 100 kg/ mz El mejor en P (0.39) y el más bajo en FC (26.61). A su vez con O kg / mz_. Observaron sus níveles minimos la PB (6.91), el ELN (53.58). el valor energético (175.45 Kcal/ 100 g) y el P (O.28), y con 100 kg/ mz los menores en MS y Cz (25.08 y 10.38 respectivamente), a. los 150kg/mz el EE (2.29) y el Ca (0.49), rindieron sus índices más bajos. En cuanto a la frecuencia de corte, la edad 15 días presentó los máximos contenidos en PH (11.95), ELN (56.45),EB (202.40 Kcal/ 100g), EE (2.65) y el mínimo en FC (27.09). Observando el corte a los 60 días, las mayores proporciones en MS (30.91) Cz (12.43) )'Ca (0.58),en tanto que con 30 y 45 días se dieron los más altos valores de P (0.34) FC (28.55) respectivamente los índices más bajos de PB (6.48),ELN (52.63), Ca (0.47)y P (0.30), se obtuvieron a los 45 días de madurez mientras que la MS (22.88) y la Cz (9.56),alcanzaron sus valores más pequeños con 15 días de corte a los 60 días, la EB (175. 42 Kcal ./ 100g) y el EE (2.20) respondieron con sus por cientos más bajos. Para los tratamientos resultantes de la combinación de un nivel de fertilizante y una edad de corte, la interacción 50 kg/mz-60 días reportó el mayor contenido en MS (32.72), sobresaliendo el tratamiento 150 kg / mz-15 días al presentar los valores más altos en EB (214.39 Kcal/100g), PB (14.30) y ELN (59.02), aunque la combinación 50 kg/mz-30 días brindó igual valor en ELN y el máximo en Cz (13.10) con aplicaciones de 100 kg/mz y frecuencia de 15 días se obtuvieron los menores índices en FC (24.82) y Cz (9.37). Consiguiéndose en O kg / mz-15 días el valor más alto en Ca (0.76) y el menor en P (0.22), observando la MS su índice más bajo (18.37) con el tratamiento 100 kg / mz-15 días. Finalmente, en las interacciones que incluyen la frecuencia 45 días, se encontró que las parcelas no fertilizadas presentaron los menores contenidos en PB (5.02), ELN (48.95) y EB (165.44 Kcal/ 1oo g). en cambio al aplicar 100 kg /rnz, se obtuvieron (para la misma interacción) los valores más bajos en EE (1.72), Ca (0.43) y el mayor en P (0.44),en tanto los niveles 50 y 150 kg / mz influyeron los índices más altos en EE (3.85) y FC (30.75) respectivamente.

Some marine algae from Ceylon - 2. Laurencia lamouroux

The herbarium material belonging to the genus Laurencia kept at the Royal Botanical Gardens, Peradeniya together with my collections of material belonging to this genus from various parts of Ceylon have been examined. Most of the material belonging to the genus Laurencia had been incorrectly identified and their true identity has been determined. A key to the Ceylon species of Laurencia is given.

Diterpenes, sesquiterpenes, and a C-15-acetogenin from the marine red alga Laurencia mariannensis

In addition to 10 known compounds (7-16), one new brominated diterpene, 10-hydroxykahukuene B (1), two new sesquiterpenes, 9-deoxyelatol (2) and isodactyloxene A (3), one new brominated C-15-acetogenin, laurenmariallene (4), and two new naturally occurring halogenated sesquiterpenes (5 and 6) that were previously obtained as intemediates in a biomimetic synthetic study of rhodolaureol and rhodolauradiol have been isolated and identified from the organic extract of the marine red alga Laurencia mariannensis. The structures of these compounds were established by spectroscopic methods. The antibacterial and antifungal activities of new compounds 1-4 were evaluated.

Halogenated Terpenes and a C-15-Acetogenin from the Marine Red Alga Laurencia saitoi

Seven parguerane diterpenes: 15-bromo-2,7,19-triacetoxyparguer-9(11)-en-16-ol (1), 15-bromo-2,7,16,19-tetraacetoxyparguer-9(11)-ene (2), 15-bromo-2,19-diacetoxyparguer-9(11)-en-7,16-diol (3), 15-bromo-2,16,19-triacetoxyparguer-9(11)-en-7-ol (4), 15bromo-2,16-diacetoxyparguer-9(11)-en-7-ol (5), 15-bromoparguer-9(11)-en-16-ol (6), 15-bromoparguer-7-en-16-ol (7), two polyether triterpenes: thyrsiferol (8) and thyrsiferyl 23-acetate (9), and one C15-acetogenin, neolaurallene (10), were isolated from a sample of marine red alga Laurencia saitoi collected off the coast of Yantai. Their structures were established by detailed NMR spectroscopic analysis and comparison with literature data.

A new rearranged chamigrane sesquiterpene from Laurencia okamurai

A new rearranged chamigrane sesquiterpene, named laurenokamurin, was isolated from the marine red alga Laurencia okamurai. Its structure was determined on the basis of spectroscopic methods. (C) 2008 Bin Gui Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

Two new aristolane sesquiterpenes from Laurencia similis

Two new aristolane sesquiterpenes, namely, aristolan-10-ol-9-one and aristolan-8-en-1-one, were isolated from the red alga Laurencia similis. Their structures were established on the basis of various NMR spectroscopic analyses, including 2D NMR techniques (H-1-H-1 COSY, HMQC, HMBC, and NOESY) and HR-FAB-MS. (c) 2007 Bin Gui Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

Laurenidificin, a new brominated C-15-acetogenin from the marine red alga Laurencia nidifica

new brominated C-15-acetogenin, namely, laurenidificin, was isolated from the marine red alga Laurencia nidifica. Its structure was determined on the basis of spectroscopic methods. (C) 2010 Bin Gui Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.