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.

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.

Chemical constituents of marine medicinal mangrove plant Sonneratia caseolaris

Twenty-four compounds including eight steroids (1-8), nine triterpenoids (9-16, 24), three flavonoids (20-22), and four benzenecarboxylic derivatives (17-19, 23) were isolated and identified from stems and twigs of medicinal mangrove plant Sonneratia caseolaris. The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data. Among these metabolites, compounds 1, 4-20 and 22-24 were isolated and identified for the first time from S. caseolaris. In the in vitro cytotoxic assay against SMMC-7721 human hepatoma cells, compound 21 (3',4',5,7-tetrahydroxyflavone) exhibited significant activity with IC50 2.8 mu g/mL, while oleanolic acid (14), 3,3'-di-O-methyl ether ellagic acid (18), and 3,3',4-O-tri-O-methyl ether ellagic acid (19) showed weak activity. None of these compounds displayed significant antibacterial activites.

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.

Mangrove plant Ceriops tagal as a potential source of anti White Spot Syndrome Virus preparations for Penaeus monodon

White spot syndrome virus (WSSV) is the deadliest virus among crustaceans ever discovered having several unique and novel features. Recent developments in genomics and proteomics could elucidate the molecular process involved in the WSSV infection and the host pathogen interaction to some extent. Until now no fool proof treatment or prophylactic measure has been made available to control WSSV out breaks in culture system. Even though there are technologies like application of immunostimulants, vaccines, RNAi and several antiviral natural products none of them has been taken to the level of clinical trials. However, there are several management options such as application of bioremediation technologies to maintain the required environmental quality, maintenance of zero water exchange systems coupled with application of probiotics and vaccines which on adoption shall pave way for successful crops amidst the rapid spread of the virus. In this context the present work was undertaken to develop a drug from mangrove plants for protecting shrimp from WSSV.Mangroves belong to those ecosystems that are presently under the threat of destruction, diversion and blatant attack in the name of so called ‘developmental activities’. Mangrove plants have unique ecological features as it serves as an ecotone between marine and terrestrial ecosystem and hence possess diversity of metabolites with diverse activities. This prompted them being used as remedial measures for several ailments for ages. Among the mangrove plants Ceriops tagal, belonging to the family Rhizophororaceae was in attention for many years for isolating new metabolites such as triterpenes, phenolic compounds, etc. Even though there were attempts to study various plant extracts to develop anti-viral preparations their activity against WSSV was not investigated as yet.

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.

Intervariability of Phosphorus Speciation in Selected Mangrove Ecosystems Around the Greater Cochin

Mangrove forests are best developed on tropical shorelines where there is an extensive intertidal zone, with an abundant supply of fine-grained sediment. It receives a mixture of liable and refractory organic and inorganic phosphorus compounds from the overlying water and the surrounding landmasses. Organic phosphorus is not available for mangrove plant nutrition. While inorganic phosphate represents the largest potential pool of plant-available and which are bound in the form of Ca, Fe and Al phosphate. It deals with the scientific investigations on mangrove systems in the Kerala coastline and to investigate nutrient distribution of mangrove ecosystems of greater Cochin area. It discusses the description of study areas such as Murikkumpadam-Vypeen Island and Aroor. Then it deals with the spatial and seasonal distribution of dissolved ammonia, nitrite, nitrate, inorganic phosphate, organic phosphate and the total phosphorus in surface waters of mangrove fringed creeks. Then it discusses the geochemical compositions of mangrove-fringed sediments and also the chemical speciation of phosphorus in sediment cores.

In vivo screening of mangrove plants for anti WSSV activity in Penaeus monodon, and evaluation of Ceriops tagal as a potential source of antiviral molecules

The objective of the study was to find out a natural way to fight white spot syndrome virus (WSSV) in cultured shrimps, as the present scenario necessitated an organic remedy for the devastating pathogen in crustaceans. Under this research programme seven mangrove plants were collected, identified and aqueous extracts screened for their protective effect on the giant tiger shrimp Penaeus monodon against WSSV. The experimental design consisted two modes of application, such as exposure of the virus to the extract and injection challenge, and oral administration of the extract coated feed followed by oral challenge. All experimental animals were monitored through a nested diagnostic PCR analysis. Of the seven mangrove extracts screened aqueous extract from Ceriops tagal imparted total protection to shrimp from WSSV when challenged by both methods. Shrimps administered with the aqueous extract from C. tagal were devoid of virions. The HPLC fingerprint of the aqueous extracts from C. tagal showed more than 25 peaks and 7 of them were larger and well separated. Preliminary phytochemical analysis revealed the presence of alkaloids, flavonoids, polyphenolics, cardiac glycosides, saponins and sterols. The study indicated suitability of the aqueous extract of C. tagal as a possible prophylaxis for WSSV infection in shrimp. This is the first report on the anti WSSV property of the mangrove plant C. tagal

In vivo screening of mangrove plants for anti WSSV activity in Penaeus monodon, and evaluation of Ceriops tagal as a potential source of antiviral molecules

The objective of the study was to find out a natural way to fight white spot syndrome virus (WSSV) in cultured shrimps, as the present scenario necessitated an organic remedy for the devastating pathogen in crustaceans. Under this research programme seven mangrove plants were collected, identified and aqueous extracts screened for their protective effect on the giant tiger shrimp Penaeus monodon against WSSV. The experimental design consisted two modes of application, such as exposure of the virus to the extract and injection challenge, and oral administration of the extract coated feed followed by oral challenge. All experimental animals were monitored through a nested diagnostic PCR analysis. Of the seven mangrove extracts screened aqueous extract from Ceriops tagal imparted total protection to shrimp from WSSV when challenged by both methods. Shrimps administered with the aqueous extract from C. tagal were devoid of virions. The HPLC fingerprint of the aqueous extracts from C. tagal showed more than 25 peaks and 7 of them were larger and well separated. Preliminary phytochemical analysis revealed the presence of alkaloids, flavonoids, polyphenolics, cardiac glycosides, saponins and sterols. The study indicated suitability of the aqueous extract of C. tagal as a possible prophylaxis for WSSV infection in shrimp. This is the first report on the anti WSSV property of the mangrove plant C. tagal

Foraminiferal ecological zonation along a Brazilian mangrove transect: Diversity, morphotypes and the influence of subaerial exposure time.

Two foraminiferal associations comprising only arenaceous species define two distinct environments in a 340 m-long mangrove transect at Cardoso Island, Trapande Bay (Cananeia-Iguape estuarine system, SP, Brazil). The "lower muddy flat" (LMF), from the outer mangrove fringe inwards towards land (100 m), is positioned in the lower plain between 0.04 and 0.23 m above the mean sea level (msl), and remains subaerially exposed between 48.5 and 65.6% of the time. This environment is characterized by higher foraminiferal diversity and evenness (McIntosh's D = 0.54 [plus or minus] 0.21 and Pielou's E = 0.68 [plus or minus] 0.25, respectively) and is dominated by Arenoparrella mexicana and Trochammina inflata, and to a lesser extent by Ammotium directum and Textularia earlandi. The mangrove plant of this segment is a Rhizophoretum with average height of 8.4 [plus or minus] 1.2 m. The sediment is characterized by higher concentration of organic matter (93.5 [plus or minus] 32.3 g dm-3) and metals (e.g. V = 53.4 [plus or minus] 21.8 ppm and Zn = 46.4 [plus or minus] 21.3 ppm). The "upper sandy flat" (USF), 240 m wide along the transect, is positioned in the upper plain between 0.28 and 0.89 m above the msl, and remains subaerially exposed between 69.7 and 98.5% of the time. This environment is characterized by a lower diversity and evenness (D = 0.33 [plus or minus] 0.17 and E = 0.49 [plus or minus] 0.20, respectively). The association is dominated by species T. inflata and Miliammina fusca. The Rhizophoretum exhibits a lower average height of 3.6 [plus or minus] 0.6 m. The sediment is poorer in organic matter (39.3 [plus or minus] 15.0 g dm-3) and metals (e.g. V = 13.0 [plus or minus] 6.8 ppm and Zn = 6.9 [plus or minus] 3.7 ppm). Whereas "elongate" tests (uniserial, biserial and planospiral followed by a uniserial portion) are restricted to the LMF, "spiraled" species dominate the USF. Subaerial exposure time seems to exert a primary influence on species distribution, in addition to salinity and sediment type. Species may be adapted to different exposure times, a factor dependent on their position on the intertidal zone and the tidal regime, which should be taken into account in relative sea level reconstructions based on intertidal foraminifera. These patterns have important implications for studies investigating the ecology and paleoecology of foraminifera and subtle fluctuations in relative sea level during the Quaternary.

Food selection by a mangrove crab: Temporal changes in fasted animals

The feeding choices of the mangrove crab Ucides cordatus for various mangrove plant leaves (Avicennia schaueriana, Laguncularia racemosa, and Rhizophora mangle) at different ages (mature, senescent pre-abscission, and decomposing leaves) were examined. In a controlled experiment set in a mangrove area, we evaluated crab selection for different plant leaves by analyzing foraging rate (number of leaves with predation marks) and leaf consumption. Crabs were housed individually in plastic containers and after a 3-day fast supplied with leaf fragments every 24 h for 72 h. Uneaten leaves were removed before each new food offering. No food selection was observed in the first day, but after this period, senescent leaves, which have a high polyphenol content, were rejected. On the third day, an interactive effect between plant species and leaf age was shown to affect leaf selection, with mature leaves of A. schaueriana and L. racemosa being more selected than the other treatments. This observation was consistent across crab sexes and ages. Our results show that food selection by this mangrove crab changes through time in fasted animals, suggesting that this variable must be controlled in food preference studies. © 2012 Springer Science+Business Media B.V.

Flavanol derivatives from Rhizophora stylosa and their DPPH radical scavenging activity

A new acetylated flavanol, 3,7-O-diacetyl (-)-epicatechin (3), and seven known flavanol derivatives, (-)-epicatechin (1), 3-O-acetyl (-)-epicatechin (2), 3,3 ',4 ',5,7-O-pentaacetyl (-)-epicatechin (4), (+)-afzelechin (5), (+)-catechin (6), cinchonain Ib (7), and proanthocyanidin B2 (8), were isolated from the stems and twigs of the mangrove plant Rhizophora stylosa and identified. The crude extract, the different fractions and all of the purified compounds were evaluated for DPPH radical scavenging activity.

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.

A new acylated iridoid glucoside from Avicennia marina

A new acylated iridoid glucoside, namely, 2'-O-(5-phenyl-2E, 4E-pentadienoyl)mussaenosidic acid, was isolated from the aerial parts of the mangrove plant Avicennia marina. The structure of the new compound was established on the basis of various NMR spectroscopic analyses, including 2D NMR techniques (H-1-H-1 COSY, HMQC, and HMBC) and HR-FAB-MS. This compound displayed moderate antioxidant activity.

红树林植物木榄和一株海藻内生真菌的化学成分研究

本论文对民间药用红树植物木榄（Bruguiera gymnorrhiza）中的次生代谢产物进行了研究，同时还对分离自似瘤凹顶藻（Laurencia similis Namet Saito）的内生真菌EN21（Exophiala oligosperma）进行了化学成分研究。对分离得到的部分化合物进行了初步的DPPH自由基清除活性和抗菌活性筛选。 采用常规的硅胶柱层析、反相硅胶柱层析、制备薄层层析、凝胶Sephadex LH-20 柱层析、半制备型高效液相色谱（HPLC）以及重结晶等手段，从木榄（Bruguiera gymnorrhiza）中分离得到23个化合物；从EN21（Exophiala oligosperma）中分离得到23个化合物。利用一维、二维核磁、质谱、元素分析等各种现代波谱技术及化学反应方法，确定了木榄中20个化合物的结构，包括黄酮单体化合物5个，三萜类化合物11个，甾体化合物2个，长链烷烃2个，其中4个化合物为首次从木榄中报道的黄酮；确定了EN-21中20个化合物的结构，其中脑苷脂1个，甾体化合物7个，芳环化合物3个，三萜类化合物2个，包括1个新天然产物。本文系首次报道Exophiala oligosperma 的化学成分。 对从木榄中分离得到的部分化合物进行了DPPH自由基清除活性筛选， 发现黄酮类化合物BRG-1、BRG-2、BRG-3 、BRG-4显示了较强的DPPH自由基清除活性，而三萜类化合物则未表现出DPPH自由基清除活性。抗菌筛选实验中所有测试样品未显示出活性。 研究结果充实了红树林植物和海藻内生真菌代谢产物的内容，为其有效利用提供了一定的科学依据。