Benzaldehyde derivatives from Eurotium rubrum, an endophytic fungus derived from the mangrove plant Hibiscus tiliaceus

Four new (1-4) and seven known (5-11) benzaldehyde derivatives were characterized from the liquid fermentation cultures of Eurotium rubrum, an endophytic fungus that was isolated from the inner tissue of stems of the mangrove plant Hibiscus tiliaceus. The structures of these compounds were determined by extensive analysis of their spectroscopic data. Among these metabolites, compound 1, which was named as eurotirumin, possesses a new carbon skeleton with a cyclopentabenzopyran ring system.

Triterpenoids from the mangrove plant Hibiscus tiliaceus

Three new triterpenoids with the rarely occurring nigrum skeleton, namely (20E)-22-hydroxynigrum-20-en-3-one (1), 21 beta-hydroxynigrum-22(29)-en-3-one (2), and 21 alpha-hydroxynigrum-22(29)-en-3-one (3), were isolated from the mangrove plant Hibiscus tiliaceus. Additionally, five known triterpenoids including friedelin (4),12-oleanen-3 beta-ol (5), 3 beta-hydroxy-12-oleanen-28-oic acid (6),20(29)-lupen-3 beta,28-diol (7). and cucurbita-5,23-dien-3 beta,25-diol (8) were also isolated and identified. The latter structures were elucidated by a detailed NMR and MS analyses, as well as by comparison with reported literature data.

Caracterização química de extratos de Hibiscus tiliaceus : estudo comparativo de métodos de extração

O presente trabalho teve como objetivo estudar a composição química das flores de Hibiscus tiliaceus L usando diferentes técnicas de extração. Os métodos de extração usados foram maceração, Soxhlet, ultra-som, extração com fluido supercrítico e extração com líquido pressurizado. Foram investigadas as variáveis que podem influenciar no processo de extração tais como temperatura, pressão, polaridade do solvente, tempo de extração e massa de amostra, entre outras. A identificação dos compostos foi realizada por cromatografia gasosa acoplada com detector de espectrometria de massas. Os métodos de extração utilizados mostraram-se eficientes para a obtenção dos extratos, com algumas diferenças qualitativas. Quantitativamente, os compostos majoritários, em todas as técnicas de extração usadas, foram ácidos carboxílicos (C16 e C18), hidrocarbonetos com número ímpar de carbonos (C27, C29 e C31) e fitosteróis. Entre os métodos de extração que utilizam solventes orgânicos, a extração com líquido pressurizado apresentou maior rendimento em massa de extrato e maior concentração de alguns dos compostos presentes nas flores de Hibiscus tiliaceus L., com as vantagens de redução de solventes e do tempo de extração. A variável que se mostrou mais importante nos procedimentos de extração foi a polaridade do solvente. A composição química das flores Hibiscus tiliaceus L apresentou além dos compostos citados, álcoois, aldeídos e vitamina E. A determinação do potencial antioxidante da planta, utilizando o método por quimiluminescência, permitiu encontrar valores para TAR e TRAP superiores ao trolox, utilizado como padrão, indicando a presença de antioxidantes nos extratos.

Chemical Constituents of a Marine-Derived Endophytic Fungus Penicillium commune G2M

Cultivation of the endophytic fungus Penicillium commune, which was isolated from the semi-mangrove plant Hibiscus tiliaceus, afforded one new compound 1-O-(2,4-dihydroxy-6-methylbenzoyl)-glycerol (1) along with thirteen known products, including 1-O-acetylglycerol (2), N-acetyltryptophan (3), 3-indolylacetic acid methyl ester (4), 1-(2,4-dihydroxy-3,5-dimethylphenyl)ethanone (5), 2-(2,5-dihydroxyphenyl)acetic acid (6), (4R,5S)-5-hydroxyhexan-4-olide (7), thymidine (8), uracil (9), thymine (10), ergosterol (11), beta-sitosterol (12), beta-daucosterol (13), and ergosta-7,22-dien-3 beta,5 alpha,6 beta-triol (14). The structures of these compounds were established by detailed NMR spectroscopic analysis, as well as by comparison with literature data or with authentic samples.

Natural Anthraquinone Derivatives from a Marine Mangrove Plant-Derived Endophytic Fungus Eurotium rubrum: Structural Elucidation and DPPH Radical Scavenging Activity

There is considerable interest in the isolation of potent radical scavenging compounds from natural resources to treat diseases involving oxidative stress. In this report, four new fungal metabolites including one new bisdihydroanthracenone derivative (1, eurorubrin), two new seco-anthraquinone derivatives [3, 2-O-methyl-9-dehydroxyeurotinone and 4, 2-O-methyl4-O-(alpha-D-ribofuranosyl)-9-dehydroxyeurotinone], and one new anthraquinone glycoside [6,3-O-(alpha-D-ribofuranosyl)questin], were isolated and identified from Eurotium rubrum, an endophytic fungal strain that was isolated from the inner tissue of the stem of the marine mangrove plant Hibiscus tiliaceus. In addition, three known compounds including asperflavin (2), 2-O-methyleurotinone (5), and questin (7) were also isolated and identified. Their structures were elucidated on the basis of spectroscopic analysis. All of the isolated compounds were evaluated for 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity.

Dioxopiperazine Alkaloids Produced by the Marine Mangrove Derived Endophytic Fungus Eurotium rubrum

Cultivation of the fungal strain Eurotium rubrum, an endophytic fungus that was isolated from the inner tissue of stems of the mangrove plant Hibiscus tiliaceus, resulted in the isolation of two new dioxopiperazine derivatives, namely, dehydrovariecolorin L (1) and dehydroechinulin (2), together with eight known dioxopiperazine compounds including variecolorin L (3), echinulin (4), isoechinulin A (5), dihydroxyisoechinulin A (6), preechinulin (7), neoechinulin A (8), neoechinulin E (9), and cryptoechinuline D (10). The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data as well as by comparison with literature. Compounds 1, 2, 9, and 10 were investigated for their a,a-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity. In addition, the new compounds, 1 and 2, were evaluated for their cytotoxic activity against the P-388, HL-60, and A549 cell lines.

两种红树林植物黄槿和长梗肖槿化学成分研究

由于红树林植物的重要药用价值及其特殊的生长环境，越来越多的学者关注于红树林植物的活性成分及其作用机理的研究。本论文对两种药用红树林植物黄槿（Hibiscus tiliaceus L.）和长梗肖槿（Thespesia populneoides (Roxb.) Kostel）的化学成分进行了系统研究。对从其中分离得到的部分化合物进行了初步的抗菌活性筛选。 黄槿和长梗肖槿均采自海南岛，干燥粉碎的样品用90％的乙醇水以及1：1氯仿-甲醇混合溶液室温浸泡提取得总浸膏，将总浸膏悬浮于水中，分别用石油醚和乙酸乙酯萃取，获得石油醚相和乙酸乙酯相萃取物。 采用常规的硅胶柱层析、制备薄层层析、凝胶Sephadex LH-20柱层析、反相硅胶柱层析、以及重结晶等手段，从黄槿和长梗肖槿的乙酸乙酯相中共分离得到43个化合物。利用各种现代波谱技术（IR、UV、MS、HR-MS、1D-NMR、2D-NMR等）确定了38个化合物的结构。其中，从黄槿的乙酸乙酯相中分离得到22个化合物，鉴定了其中19个化合物的结构，包括3个新的三萜类化合物(H1*-H3*)以及15个首次从该种中报道的化合物。从长梗肖槿的乙酸乙酯相中分离得到21个化合物，鉴定了其中19个化合物的结构，这些化合物皆为首次从该种中报道，其中1个为新的倍半萜类化合物T1*。本文为首次报道长梗肖槿的化学成分。 对分离得到的部分样品进行了抗菌活性测试，仅T1*表现微弱的抗金黄色葡萄球菌活性，抑菌圈直径为8mm（阳性对照氯霉素的抑菌圈直径为20mm），其余各样品在测试浓度下对测试菌株均未表现出活性。

黄槿内生真菌赤散囊菌及红海榄的次生代谢产物及其生物活性研究

由于生长环境的特殊性，红树林及其内生真菌的代谢产物在化学类型和生物活性方面都具有多样性，因此对其代谢产物的研究引起了人们越来越多的关注。本论文以菌丝体生物量、代谢产物量等指标及薄层色谱分析、高效液相色谱分析、抗菌活性测试等筛选手段对来源于我国海南红树植物的九株内生真菌在四种不同液体培养基上的静置发酵产物进行了综合评价，并从中选择了来源于半红树植物黄槿（Hibiscus tiliaceus）的内生真菌G2——赤散囊菌（Eurotium rubrum）进行了30 L规模发酵（采用PDB培养基）和次生代谢产物的研究，对分离得到的部分化合物进行了初步的生物活性评价。此外，本论文还对海南真红树植物红海榄（Rhizophora stylosa Griff.）的化学成分进行了研究，并对分离得到的部分化合物进行了二苯代苦味酰自由基（DPPH）清除活性的评价。 采用常规的硅胶柱层析、Sephadex LH-20柱层析、反相硅胶柱层析、制备薄层层析（pTLC）、重结晶等分离手段，分离纯化得到单体化合物。综合运用现代波谱技术 (IR、UV、MS、1D-NMR 和 2D-NMR) 以及与标准品或文献比对鉴定单体化合物的结构。从G2菌丝体和发酵液的合并提取物中鉴定了45个化合物的结构，其中13个为新化合物，结构类型包括6个苯甲醛类化合物（ER1*~ER6*）、4个蒽醌类化合物（ER15*~ ER18*）和3个含吲哚的二酮哌嗪生物碱类化合物（ER27*~ER29*）。 对以上分离鉴定的部分单体化合物进行了DPPH自由基清除活性、拒食杀虫活性、抗细菌活性以及体外细胞毒活性的初步评价。新化合物ER15*和三个已知化合物ER20、ER39和ER40都表现很强的DPPH自由基清除活性。化合物ER15*还表现较好的拒食杀虫活性，而化合物ER5*和ER18*不但没有杀虫活性，反而能促进幼虫的生长。所测试的化合物只有ER15*和ER18*表现出微弱的抗金黄色葡萄球菌活性。所测试的化合物对A-549、HL-60和P-388细胞株均未表现出有意义的体外细胞毒活性。 从红海榄枝条的提取物中分离鉴定了29个化合物，其中2个为新化合物，包括1个三萜酯（RS1*）和1个黄烷醇类化合物（RS12*）；另有1个三萜酯（RS5）和1个黄烷醇类化合物（RS11）作为新的天然产物被分离鉴定。 对从红海榄提取物乙酸乙酯相和正丁醇相分离得到的部分单体化合物进行了DPPH自由基清除活性的研究。黄烷醇类化合物RS16和RS17显示最强的活性。另外，实验结果说明黄烷醇类化合物的DPPH自由基清除活性与其分子中所含的羟基数目有一定关系，而且若芳香环上有多个邻位酚羟基，则该化合物的活性将增强。本论文实验结果为海南红海榄植物资源的利用提供了化学成分及抗氧化活性方面的科学依据。

Aplicação dos isótopos estáveis em aqüicultura

O produto mais importante do conhecimento é a ignorância. A situação sugere a imagem de alguém que vive numa ilha de conhecimento cercado por um mar de ignorância. Quando a área dessa ilha aumenta pelo progresso da ciência, também aumenta o litoral, - a fronteira com o desconhecido. Esta expansão é o fruto mais valioso do conhecimento (David Gross, Nobel em Física, 2004). O uso dos isótopos estáveis dos bioelementos (CHON'S) presentes na Atmosfera, Hidrosfera, Litosfera e Biosfera enquadra-se neste contexto, surgindo como ferramenta de alto potencial em pesquisas nas diversas áreas das Ciências da Vida. Com organismos aquáticos, a aplicação dos isótopos estáveis do carbono (δ 13C) e do nitrogênio (δ 15N) tem ocorrido em diversas áreas. em larvas de pacu Piaractus mesopotamicus, a técnica evidenciou a escolha voluntária entre organismos vivos e dieta seca pelos animais, desde as primeiras alimentações até o final da larvicultura. Na carcinicultura, o crescimento do Penaeus vannamei resultou do aproveitamento dos alimentos oferecidos e da produtividade primária do lago (biota). Por meio do balanço de massa e isotópico foi possível determinar a contribuição da biota, da ordem de 44 a 86% do carbono assimilado pelos animais durante o crescimento. Outro exemplo é com o caranguejo de mangue Sesarma rectum, em que sua preferência alimentar por Spartina alterniflora (C4) versus Rhizophora mangle (C3) ou Hibiscus tiliaceus (C3) foi evidenciada pelo modelo isotópico de duas fontes alimentares e os isótopos estáveis do carbono (δ13C). A técnica dos isótopos estáveis associada ao conhecimento dos conceitos básicos da variabilidade isotópica natural e ao uso criterioso das razões 13C/12C; ²H/¹H; 18O/16O; 15N/14N e 36S/34S revela-se como um avanço na fronteira dos conhecimentos, nas diversas reentrâncias do litoral da aqüicultura.

Emergence and seed persistence of Echinochloa colona, Urochloa panicoides and Hibiscus trionum in the sub-tropical environment of north-eastern Australia.

Better understanding of seed-bank dynamics of Echinochloa colona, Urochloa panicoides and Hibiscus trionum, major crop weeds in sub-tropical Australia, was needed to improve weed control. Emergence patterns and seed persistence were investigated, with viable seeds sown at different depths in large in-ground pots. Seedlings of all species emerged between October and March when mean soil temperatures were 21-23C. However, E. colona emerged as a series of flushes predominantly in the first year, with most seedlings emerging from 0-2 cm. Urochloa panicoides emerged mostly as a single large flush in the first two years, with most seedlings emerging from 5 cm. Hibiscus trionum emerged as a series of flushes over three seasons, initially with majority from 5 cm and then 0-2 cm in the later seasons. Longevity of the grass seed was short, with <5% remaining after burial at 0-2 cm for 24 months. In contrast, 38% of H. trionum seeds remained viable after the same period. Persistence of all species increased significantly with burial depth. These data highlight that management strategies need to be tailored for each species, particularly relating to the need for monitoring, application times for control tactics, impact of tillage, and time needed to reduce the seed-bank to low numbers.

Insect induced bud fall in cultivated hibiscus and aspects of the biology of Macroura concolor (Macleay) (Coleoptera: Nitidulidae)

The influence of insect attack on bud fall and subsequent poor flowering in cultivated hibiscus (Hibiscus rosa-sinensis) was studied in cages and in the field in southern Queensland. Three species of Hemiptera (most importantly Aulacosternum nigrorubrum but also Nezara viridula and Tectocoris diophthalmus) caused some bud fall in 2 plantations studied. Adults of Macroura concolor suppressed flowering for long periods in spring and summer. Data from white funnel traps and counts in flowers showed that M. concolor was most active in these seasons. Methiocarb (0.75 g a.i./litre) reduced beetle numbers and increased flowering. When 15 or more adults of M. concolor occurred per bud (or flower) most buds fell and few flowers were produced, but when beetles declined to 10 or fewer many buds survived and widespread flowering occurred. Larvae fed in fallen buds and flowers and the mean duration of development of the combined immature stages was 14 days at 26 deg C. The preference of adults of M. concolor for pale coloured flowers was examined. Hibiscus plants produced most buds from December to June with lower numbers in winter and spring (July to November). Bud production in spring and early summer (September-December) varied greatly and probably contributed to poor flowering, however, even when large numbers of buds occurred very few flowers were produced because of the activities of M. concolor.

Producción y composición química de la avispa (Hibiscus rosa-sinensis), a diferentes frecuencias de corte, Rancho Ebenezer, Masaya, Nicaragua

Se llevó a cabo un estudio durante el período lluvioso del año 2005, ‘Rancho Agropecológico’ “EBENEZER” Comarca ‘Hoja Chigüe’ Niquinohomo, Masaya, Nicaragua. El objetivo fue determinar la producción de materia seca y composición química de la biomasa a diferentes frecuencias de corte en Avispa (Hibiscus rosa - sinensis) . Se utilizó un diseño de bloques completos al azar (BCA) con tres repeticiones. Las frecuencias de corte fueron; 30, 45 y 60 días de rebrote. Las variables de estudio fueron longitud de rebrotes (cm), rendimiento de materia seca (kg de MS/ha/corte), porcentajes de materia seca, proteína cruda, fibra cruda, calcio y fósforo. Se realizaron análisis de varianza (ANDEVA) y separaciones de medias, usando Duncan (P<0.05). Las variables codificadas en porcentajes se transformaron, según, dos veces por el arco seno de la raíz cuadrada de la proporción, con el fin de ajustar los datos porcentuales a una distribución normal, Los resultados indican diferencias significativ as entre tratamientos para las variables; longitud de rebrote ( 29.90 y 1 3 .57 cm para frecuencias de 60 y 30 días); rendimiento de materia seca (1, 279.2 y 346.0 kg/ha/corte, para las mismas frecuencias). Se encontraron diferencias significativas para la materia seca (2 6.03, 15.15% para 60 y 30 días), proteína cruda (18.62 y, 23.16% para las mismas frecuencias), y fibra cruda (20.16 VS 15.67 % para 60 y 30 días). En cuanto a minerales, se encontró diferencias estadísticas para el fósforo no así, para el caso del calcio. El estudio permitió demostrar diferencias marcadas en la producción y composición química del forraje de Avispa (Hibiscus rosa-sinensis), observándose que, a diferencias de otros forrajes, los parámetros de calidad no presentan una disminución drástica a medida que se aumenta la edad de rebrote, con las frecuencias estudiadas.