The cytotoxic activities of the ethyl acetate and butanol crude extracts of marine cyanobacteria collected from Udar Island, Malaysia

The ocean is abundant in organisms beneficial to living beings, including cyanobacteria that are widely studied for their bioactive compounds. This research was conducted to observe the compounds and concomitant cytotoxic activities of cyanobacteria in Udar Island waters, Sabah, Malaysia, against cancer cells. The samples were identified by the 16S DNA method, and a phylogenetic tree was built to check similarities in the genus. The samples were extracted using ethyl acetate and butanol. Afterward, the compounds were determined by Liquid Chromatography-Mass Spectrometry (LCMS), while the cytotoxicity activities were examined by the MTT assay. Several known compounds in ethyl acetate crude extract, such as several types of Apratoxins, and possible new compounds were observed. The compounds examined were mainly peptide. The crude ethyl acetate extracts of Moorea sp. in Udar Island waters were found to contain cytotoxic compounds, with the IC50 value of 0.072 µg/mL against the MCF-7 breast cancer cell lines, that were more potent compared to the butanol crude extract, whose IC50 was 2.031 µg/mL. Further isolation and cytotoxic tests are necessary to confirm which compounds are responsible as cytotoxic agents. This finding provides an opportunity for the discovery of anticancer compounds from marine cyanobacteria

Cytotoxicity and antibacterial poteltial of haligenated chamigrenes from Malaysian red algae, Laurencia majuscula

Red algae of the genus Laurencia have been known to produce a wide array of bioactive secondary metabolites. Here, we report the isolation of two new halogenated chamigrenes, lauremantanones A (1) and B (2), along with seven known compounds, dendroidiol (3), (+)-elatol (4), cartilagineol (5), obtusol (6), (+)-laurencenone B (7), 2-chloro-3-hydroxy- α-chamigren-9- one (8), and puertitol A (9), from a population of Laurencia majuscula (Harvey) Lucas from Mantanani Island (North Borneo). The structures of the two new metabolites were determined based on spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds isolated from this alga exhibited potent cytotoxic (HeLa, MCF-7, P-388) and antibacterial (against antibiotic-resistant clinical bacteria) activities. The major metabolite of this population has significant importance in the geographical distribution of this species globally

Biosurfactants from marine Cyanobacteria collected in Malaysia, Sabah

ABSTRACT Chemical investigation of the organic extract from Moorea bouillonii, collected in Sabah, Malaysia, led to the isolation of three new chlorinated fatty acid amides, columbamides F (1), G (2), and H (3). The planar structures of 1–3 were established by a combination of mass spectrometric and NMR spectroscopic analyses. The absolute configuration of 1 was determined by Marfey’s analysis of its hydrolysate and chiral-phase HPLC analysis after conversion and esterification with Ohrui’s acid, (1S,2S)-2- (anthracene-2,3-dicarboximido) cyclohexanecarboxylic acid. Compound 1 showed biosurfactant activity by an oil displacement assay. Related known fatty acid amides columbamide D and serinolamide C exhibited biosurfactant activity with critical micelle concentrations of about 0.34 and 0.78 mM, respectively

Bioactivities of Lyngbyabellins from Cyanobacteria of Moorea and Okeania Genera

Cyanobacteria are reported as rich sources of secondary metabolites that provide biological activities such as enzyme inhibition and cytotoxicity. Ten depsipeptide derivatives (lyngbyabellins) were isolated from a Malaysian Moorea bouillonii and a Red Sea Okeania sp.: lyngbyabellins G (1), O (2), P (3), H (4), A (7), 27-deoxylyngbyabellin A (5), and homohydroxydolabellin (6). This study indicated that lyngbyabellins displayed cytotoxicity, antimalarial, and antifouling activities. The isolated compounds were tested for cytotoxic effect against human breast cancer cells (MCF7), for antifouling activity against Amphibalanus amphitrite barnacle larvae, and for antiplasmodial effect towards Plasmodium falciparum. Lyngbyabellins A and G displayed potent antiplasmodial effect against Plasmodium, whereas homohydroxydolabellin showed moderate effect. For antifouling activity, the side chain decreases the activity slightly, but the essential feature is the acyclic structure. As previously reported, the acyclic lyngbyabellins are less cytotoxic than the corresponding cyclic ones, and the side chain increases cytotoxicity. This study revealed that lyngbyabellins, despite being cytotoxic agents as previously reported, also exhibit antimalarial and antifouling activities. The unique chemical structures and functionalities of lyngbyabellin play an essential role in their biological activities

Induction of larval metamorphosis in the sea cucumber Apostichopus japonicus by neurotransmitters

Larval metamorphosis inducers of the sea cucumber Apostichopus japonicus were screened from physiologically active compounds. Doliolaria larvae completed their metamorphosis to juveniles in 120 hours when treated with 5-10 μM of dopamine and L-DOPA, and 50 μM of L-adrenaline and L-noradrenaline. Doliolaria larvae had to be exposed to dopamine or L-DOPA for at least 24 h. D1-like dopamine receptor antagonists SKF87566 and LE300 (10 μM) inhibited metamorphosis by dopamine. However, the D2-like dopamine receptor antagonists sulpiride and nemonapride (10 μM) did not inhibit the effect of dopamine. The results suggest that D1-like dopamine receptors are involved in larval metamorphosis of the sea cucumber A. japonicus

Late Pleistocene changes in terrestrial biomarkers in sediments from the central Arctic Ocean

Biomarkers in Late Pleistocene sediments collected from the Integrated Ocean Drilling Program (IODP)-Arctic Coring Expedition (ACEX) Hole M0004C (central Arctic Ocean) were investigated. The major biomarkers are long-chain n-alkanes, n-fatty acids and n-alkan-1-ols, indicating fresh organic matter (OM) derived predominantly from higher plants. The dominance of terrestrial biomarkers is attributed to severe OM degradation caused by slow sedimentation in oxygen-rich benthic water and/or low primary production due to permanent sea-ice coverage. Hopanes, representing thermally altered OM, tend to be abundant in samples with abundant ice rafted debris (IRD). An OM-rich dark grey layer deposited during marine isotope stage (MIS) 6 contains a significant amount of branched glycerol dialkyl glycerol tetraethers (branched GDGTs), suggesting ice erosion of organic-rich continental soil followed by transportation to the central Arctic by drifting ice. The labile–refractory index (i.e., the abundance ratio of long-chain n-alkan-1-ols to the sum of long-chain n-alkanes and long-chain n-alkan-1-ols) decreases above the dark grey layer, indicating that the OM became more refractory. This change suggests that coverage of the source region by OM-rich soil decreased because of extensive glacial erosion during MIS-6

The cytotoxic activities of the ethyl acetate and butanol crude extracts of marine cyanobacteria collected from Udar Island, Malaysia

The ocean is abundant in organisms beneficial to living beings, including cyanobacteria that are widely studied for their bioactive compounds. This research was conducted to observe the compounds and concomitant cytotoxic activities of cyanobacteria in Udar Island waters, Sabah, Malaysia, against cancer cells. The samples were identified by the 16S DNA method, and a phylogenetic tree was built to check similarities in the genus. The samples were extracted using ethyl acetate and butanol. Afterward, the compounds were determined by Liquid Chromatography-Mass Spectrometry (LCMS), while the cytotoxicity activities were examined by the MTT assay. Several known compounds in ethyl acetate crude extract, such as several types of Apratoxins, and possible new compounds were observed. The compounds examined were mainly peptide. The crude ethyl acetate extracts of Moorea sp. in Udar Island waters were found to contain cytotoxic compounds, with the IC50 value of 0.072 µg/mL against the MCF-7 breast cancer cell lines, that were more potent compared to the butanol crude extract, whose IC50 was 2.031 µg/mL. Further isolation and cytotoxic tests are necessary to confirm which compounds are responsible as cytotoxic agents. This finding provides an opportunity for the discovery of anticancer compounds from marine cyanobacteria

Heat shock and iron limitation modulate the metabolic profile of the cyanobacterium Microcystis aeruginosa NIES-88

The freshwater cyanobacterium Microcystis aeruginosa NIES-88, which can produce microcystins, micropeptins, and argicyclamides, was subjected to a one strain many compounds (OSMAC) analysis. We report its response to two environmental stressors, temperature and iron limitation, by means of untargeted and targeted metabolomics. The results demonstrated a slower specific growth rate of 0.20 per day and 0.16 per day in adverse conditions of 37 & DEG;C and iron limitation, respectively. The metabolic signature of M. aeruginosa was highly dependent on incubation temperatures. Production of microcystins LR and RR was severely downregulated while that of argicyclamide B was significantly upregulated, with a highest 10-fold increase on day 14 of heat shock treatment. M. aeruginosa NIES-88 was found to produce a new compound, argicyclamide D (1), in iron limited medium, which has the same macrocyclic structure as the previously reported analogs. Hence, it is proposed that acclimation of M. aeruginosa to environmental stressors might be mediated by a change in the metabolic pathways as well as modulation of the levels of their expressed metabolites

Antioxidants from the Brown Alga Dictyopteris undulata

An investigation of anti-oxidative compounds from the brown alga Dictyopteris undulata has led to the isolation and identification of isozonarol, isozonarone, chromazonarol, zonaroic acid and isozonaroic acid. Their structures were identified by comparison of MS and NMR spectra. Full NMR assignment and absolute configuration of isozonaroic acid are described. Isozonarol showed the most potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity among the compounds isolated