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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), 15-bromo-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.

The red algal genus Laurencia is a prolific producer of halogenated secondary metabolites. A new tricyclic dibrominated diterpenoid, neoiriepentaol (1) and chlorinated C15-acetogenin, nangenyne (2), along with two known terpenoids, neoirietetraol (3) and dactyloxene A (4), were isolated from methanol crude extract of red alga Laurencia nangii. The structures were established based on one- and two-dimensional nuclear magnetic resonance (NMR), Fourier-transform infrared (FTIR), and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. These compounds were screened against seven species of marine fungi. Compounds 1-3 exhibited activity against Lagenidium thermophilum and Haliphthoros sabahensis. Potent activity was showed by 1 with L. thermophilum hyphal inhibition at MIC value of 12.5 μg mL−1 and hyphal motility was observed at 50 μg mL−1 within 24 h. [ABSTRACT FROM AUTHOR]

A new C15-acetogenin, sagonenyne (20), exhibiting an unusual single tetrahydropyran ring was isolated from an ethyl acetate extract of Laurencia obtusa collected on the Corsican coastline. Its structure was established by detailed NMR spectroscopic analysis, mass spectrometry, and comparison with literature data. Twenty-three known compounds were identified in the same extract by means of column chromatography steps, using a 13C-NMR computer aided method developed in our laboratory. In addition to sesquiterpenes, which represent the main chemical class of this extract, diterpenes, sterols, and C15-acetogenins were identified. The crude extract was submitted to a cytotoxicity assay and was particularly active against THP-1 cells, a human leukemia monocytic cell line.

A new C15-acetogenin, sagonenyne (20), exhibiting an unusual single tetrahydropyran ring was isolated from an ethyl acetate extract of Laurencia obtusa collected on the Corsican coastline. Its structure was established by detailed NMR spectroscopic analysis, mass spectrometry, and comparison with literature data. Twenty-three known compounds were identified in the same extract by means of column chromatography steps, using a 13C-NMR computer aided method developed in our laboratory. In addition to sesquiterpenes, which represent the main chemical class of this extract, diterpenes, sterols, and C15-acetogenins were identified. The crude extract was submitted to a cytotoxicity assay and was particularly active against THP-1 cells, a human leukemia monocytic cell line. [ABSTRACT FROM AUTHOR]

A unifying stereochemical analysis for the formation of the constitutional isomeric halogenated C(15)-acetogenin medium-ring ether natural products from Laurencia species is presented, where an intramolecular bromonium ion assisted epoxide ring-opening reaction of enantiomerically pure epoxides can account for ring-size, the position of the halogen substituents, and relative and absolute configurations of the known natural products. Experimentally, a model epoxide corroborates the feasibility of this process for concurrent formation of 7-, 8- and 9-ring ethers corresponding to the halogenated medium-ring ethers of known metabolites from Laurencia species.

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 intermediates 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.

Two new C15-acetogenins, 4-epi-isolaurallene (1) and 4-epi-itomanallene A (2) were isolated from a population of marine red alga Laurencia nangii Masuda from Carrington Reef. The structures of these compounds were determined intensively by NMR and HRESIMS data. Their configurations were elucidated by detailed comparison of chemical shifts, germinal protons splitting and NOE correlations with known and synthesized analogues. In addition, antibacterial activities of these compounds were evaluated. These compounds would serve as diastereomeric models for future reference. Since the isolaurallene, neolaurallene, 9-acetoxy-1,10,12-tribromo-4,7:6,13-bisepoxypentadeca-1,2-diene, itomanallene A and laurendecumallene A were isolated, compounds 1 and 2 were the sixth example of C15-acetogenin with dioxabicyclo[7.3.0]dodecene skeleton. [ABSTRACT FROM AUTHOR]

Six populations of Laurencia nangii were found to produce three bromoallenes; dihydroitomanallene B (1), itomanallene B (2) and pannosallene (3). Prior to this report, L. nangii were only known to produce C15-acetogenins with acetylene functionality. This could be regarded as a new chemical race of L. nangii. The compound structures were elucidated on the basis of spectroscopic analysis and comparison with those previously reported in literature. Compound 1, dihydroitomanallene B, was isolated as a new compound representing a minor variation of itomanallene B (2).

The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa, collected in Corsica, allowed for the identification of three new compounds (1, 2, and 4) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysis. Compounds 1 and 2 are two C15-acetogenins sharing the same ring system: a tetrahydropyran linked by a methylene to a tetrahydrofuran ring. Compound 1 exhibits a bromoallene unit whereas compound 2 possesses an uncommon α-bromo-α,β-unsaturated aldehyde terminal unit. Compound 4 is the first diterpene exhibiting a 19(4 → 3)abeo-labdane skeleton isolated from a Laurencia species. Isolation of concinndiol (compound 3) together with compound 4 suggests a common biosynthetic origin. Additionally, five known compounds, namely sagonenyne, laurene, α-bromocuparene, microcladallene A, and β-snyderol were identified in chromatographic fractions by NMR analysis using a computerized method that was developed in our laboratory.

Two new halogenated nonterpenoids C15-acetogenins, nangallenes A-B (1-2), together with two known halogenated compounds itomanallene A (3) and 2,10-dibromo-3-chloro-α-chamigrene (4), were isolated and identified from the organic extract of the marine red alga Laurencia nangii Masuda collected from the coastal waters in Semporna, Borneo. Their structures were established by means of spectroscopic analysis including IR, high-resolution electrospray ionization mass spectrometry (HRESI-MS), and 1D and 2D NMR techniques. All these metabolites were submitted for the antifungal assay against four species of selected marine fungi. Compounds 1-4 showed potent activity against Haliphthoros sabahensis and Lagenidium thermophilum. [ABSTRACT FROM AUTHOR]

Six populations of Laurencia nangii were found to produce three bromoallenes; dihydroitomanallene B (1), itomanallene B (2) and pannosallene (3). Prior to this report, L. nangii were only known to produce C15-acetogenins with acetylene functionality. This could be regarded as a new chemical race of L. nangii. The compound structures were elucidated on the basis of spectroscopic analysis and comparison with those previously reported in literature. Compound 1, dihydroitomanallene B, was isolated as a new compound representing a minor variation of itomanallene B (2). [ABSTRACT FROM AUTHOR]

The present study focused on the physiological and biochemical aspects of Tricleocarpa fragilis, red seaweed belonging to the phylum Rhodophyta, along the South Andaman coast, with particular attention given to its symbiotic relationships with associated flora and fauna. The physicochemical parameters of the seawater at the sampling station, such as its temperature, pH, and salinity, were meticulously analyzed to determine the optimal harvesting period for T. fragilis. Seaweeds attach to rocks, dead corals, and shells in shallow areas exposed to moderate wave action because of its habitat preferences. Temporal variations in biomass production were estimated, revealing the highest peak in March, which was correlated with optimal seawater conditions, including a temperature of 34 ± 1.1 °C, a pH of 8 ± 0.1, and a salinity of 32 ± 0.8 psu. GC‒MS analysis revealed n-hexadecanoic acid as the dominant compound among the 36 peaks, with major bioactive compounds identified as fatty acids, diterpenes, phenolic compounds, and hydrocarbons. This research not only enhances our understanding of ecological dynamics but also provides valuable insights into the intricate biochemical processes of T. fragilis. The established antimicrobial potential and characterization of bioactive compounds from T. fragilis lay a foundation for possible applications in the pharmaceutical industry and other industries. [ABSTRACT FROM AUTHOR]

The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa, collected in Corsica, allowed for the identification of three new compounds (1, 2, and 4) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysis. Compounds 1 and 2 are two C15-acetogenins sharing the same ring system: a tetrahydropyran linked by a methylene to a tetrahydrofuran ring. Compound 1 exhibits a bromoallene unit whereas compound 2 possesses an uncommon α-bromo-α,β-unsaturated aldehyde terminal unit. Compound 4 is the first diterpene exhibiting a 19(4 → 3)abeo-labdane skeleton isolated from a Laurencia species. Isolation of concinndiol (compound 3) together with compound 4 suggests a common biosynthetic origin. Additionally, five known compounds, namely sagonenyne, laurene, α-bromocuparene, microcladallene A, and β-snyderol were identified in chromatographic fractions by NMR analysis using a computerized method that was developed in our laboratory. [ABSTRACT FROM AUTHOR]

Candida spp. are common opportunistic microorganisms in the human body and can cause mucosal, cutaneous, and systemic infections, mainly in individuals with weakened immune systems. Candida albicans is the most isolated and pathogenic species; however, multi-drug-resistant yeasts like Candida auris have recently been found in many different regions of the world. The increasing development of resistance to common antifungals by Candida species limits the therapeutic options. In light of this, the present review attempts to discuss the significance of marine natural products in controlling the proliferation and metabolism of C. albicans and non-albicans species. Natural compounds produced by sponges, algae, sea cucumber, bacteria, fungi, and other marine organisms have been the subject of numerous studies since the 1980s, with the discovery of several products with different chemical frameworks that can inhibit Candida spp., including antifungal drug-resistant strains. Sponges fall under the topmost category when compared to all other organisms investigated. Terpenoids, sterols, and alkaloids from this group exhibit a wide array of inhibitory activity against different Candida species. Especially, hippolide J, a pair of enantiomeric sesterterpenoids isolated from the marine sponge Hippospongia lachne, exhibited strong activity against Candida albicans, Candida parapsilosis, and Candida glabrata. In addition, a comprehensive analysis was performed to unveil the mechanisms of action and synergistic activity of marine products with conventional antifungals. In general, the results of this review show that the majority of chemicals derived from the marine environment are able to control particular functions of microorganisms belonging to the Candida genus, which can provide insights into designing new anti-candidal therapies. [ABSTRACT FROM AUTHOR]

The gene encoding vanadium-dependent bromoperoxidase (V-BPO) was cloned for the first time from the red alga Laurencia saitoi, which produces pharmaceutically promising brominated diterpenoids and triterpenoids. The molecular weight of V-BPO from L. saitoi (LsVBPO1) was the highest (77.0 kDa) among previously reported V-BPOs from Laurencia with a peptide insertion Asn194-Ser221 containing short Gln repeats. It shares approximately 60% amino acid sequence identity with V-BPOs from L. nipponica (LnVBPO1 and LnVBPO2) and L. okamurae (LoVBPO1a and LoVBPO2a). Heterologously expressed LsVBPO1 in Escherichia coli was partially purified and exhibited low but significant bromination activity of 38 U mg−1 protein using monochlorodimedone. The pH optimum was 8.0, which was more alkaline than that for LnVBPOs and LoVBPO2a (pH 7.0). The Km for H2O2 was 0.04 mM, comparable to LnVBPO1 (0.026 mM), LnVBPO2 (0.025 mM), and LoVBPO2a (0.014 mM). LsVPBO1 retained its bromination activity until 45 °C for 20 min. When incubated at 55 °C for 20 min, catalytic activity decreased rapidly, as shown for LnVBPO1 and LoVBPO2a (retained at 45 °C, decreased at 55 °C) and LnVBPO2 (retained at 55 °C, decreased at 65 °C). Unlike other V-BPOs from Laurencia (LnVBPO1, LnVBPO2, and LoVBPO2a), dialysis and concentration during purification process were rapidly inactivated LsVBPO1, suggesting its structural instability. [ABSTRACT FROM AUTHOR]

The control of tetrahedral carbon stereocentres remains a focus of modern synthetic chemistry and is enabled by their configurational stability. By contrast, trisubstituted nitrogen1, phosphorus2 and sulfur compounds3 undergo pyramidal inversion, a fundamental and well-recognized stereochemical phenomenon that is widely exploited4. However, the stereochemistry of oxonium ions—compounds bearing three substituents on a positively charged oxygen atom—is poorly developed and there are few applications of oxonium ions in synthesis beyond their existence as reactive intermediates5,6. There are no examples of configurationally stable oxonium ions in which the oxygen atom is the sole stereogenic centre, probably owing to the low barrier to oxygen pyramidal inversion7 and the perception that all oxonium ions are highly reactive. Here we describe the design, synthesis and characterization of a helically chiral triaryloxonium ion in which inversion of the oxygen lone pair is prevented through geometric restriction to enable it to function as a determinant of configuration. A combined synthesis and quantum calculation approach delineates design principles that enable configurationally stable and room-temperature isolable salts to be generated. We show that the barrier to inversion is greater than 110 kJ mol−1 and outline processes for resolution. This constitutes, to our knowledge, the only example of a chiral non-racemic and configurationally stable molecule in which the oxygen atom is the sole stereogenic centre.The design, synthesis and characterization of a helically chiral triaryloxonium ion is reported, which is an example of a chiral non-racemic and configurationally stable molecule in which the oxygen atom is the sole stereogenic centre. [ABSTRACT FROM AUTHOR]

We examined the chemical constitution of the red alga Laurencia saitoi Perestenko, collected from Katsuura, Boso Peninsula, Chiba Prefecture, Japan. This specimen produced a new polyhalogenated acetogenin, named katsuurallene (1), which structure was determined by the spectral methods, along with known diterpene, deoxyparguerol (2) and triterpene, thyrsiferol (3). In this paper we describe the structural elucidation of katsuurallene together with some biological activities. [ABSTRACT FROM AUTHOR]

The total syntheses of 12-epoxyobtusallene IV, 12-epoxyobtusallene II, obtusallene X, marilzabicycloallene C, and marilzabicycloallene D as halogenated C15-acetogenin 12-membered bicyclic and tricyclic ether bromoallene-containing marine metabolites from Laurencia species are described. Two enantiomerically pure C4-epimeric dioxabicyclo[8.2.1]tridecenes were synthesized by E-selective ring-closing metathesis where their absolute stereochemistry was previously set via catalytic asymmetric homoallylic epoxidation and elaborated via regioselective epoxide-ring opening and diastereoselective bromoetherification. Epimeric face-selective oxidation of their Δ12,13 olefins followed by bromoallene installation allowed access to the oppositely configured 12,13-epoxides of 12-epoxyobtusallene II and 12-epoxyobtusallene IV. Subsequent exploration of their putative biomimetic oxonium ion formation-fragmentations reactions revealed diastereodivergent pathways giving marilzabicycloallene C and obtusallene X, respectively. The original configurations of the substrates evidently control oxonium ion formation and their subsequent preferred mode of fragmentation by nucleophilic attack at C9 or C12. Quantum modeling of this stereoselectivity at the ωB97X-D/Def2-TZVPPD/SCRF = methanol level revealed that in addition to direction resulting from hydrogen bonding, the dipole moment of the ion-pair transition state is an important factor. Marilzabicycloallene D as a pentahalogenated 12-membered bicyclic ether bromoallene was synthesized by a face-selective chloronium ion initiated oxonium ion formation-fragmentation process followed by subsequent bromoallene installation. [ABSTRACT FROM AUTHOR]

A polyoxygenated and halogenated labdane, spongianol (1); a polyoxygenated steroid, 3β,5α,9α-trihydroxy-24S-ethylcholest-7-en-6-one (2); a rare seven-membered lactone B ring, (22E,24S)-ergosta-7,22-dien-3β,5α-diol-6,5-olide (3); and an α,β-unsaturated fatty acid, (Z)-3-methyl-9-oxodec-2-enoic acid (4) as well as five known compounds, 10-hydroxykahukuene B (5), pacifenol (6), dysidamide (7), 7,7,7-trichloro-3-hydroxy-2,2,6-trimethyl-4-(4,4,4-trichloro-3-methyl-1-oxobu-tylamino)-heptanoic acid methyl ester (8), and the primary metabolite 2'-deoxynucleoside thymidine (9), have been isolated from the Red Sea sponge Spongia sp. The stereoisomer of 3 was discovered in Ganoderma resinaceum, and metabolites 5 and 6, isolated previously from red algae, were characterized unprecedentedly in the sponge. Compounds 7 and 8 have not been found before in the genus Spongia. Compounds 1–9 were also assayed for cytotoxicity as well as antibacterial and anti-inflammatory activities. [ABSTRACT FROM AUTHOR]

The chemical diversity of the approximately 1,200 natural products isolated from red algae of the genus Laurencia, in combination with the wide range of their biological activities, have placed species of Laurencia in the spotlight of marine chemists' attention for over 60 years. The chemical investigation of the organic (CH2Cl2/MeOH) extracts of Laurencia microcladia and Laurencia obtusa, both collected off the coasts of Tinos island in the Aegean Sea, resulted in the isolation of 32 secondary metabolites, including 23 C15 acetogenins (1–23), 7 sesquiterpenes (24–30) and 2 diterpenes (31 and 32). Among them, six new C15 acetogenins, namely 10-acetyl-sagonenyne (2), cis-sagonenyne (3), trans-thuwalenyne C (4), tinosallene A (11), tinosallene B (12) and obtusallene XI (17), were identified and their structures were elucidated by extensive analysis of their spectroscopic data. Compounds 1–3, 5–11, 13 and 15–32 were evaluated for their antibacterial activity against Staphylococcus aureus and Escherichia coli. [ABSTRACT FROM AUTHOR]

Abstract: Three new halogenated sesquiterpenes, 10-bromo-7α,8α-expoxychamigr-1-en-3-ol (1), 10-bromo-β-chamigren-8-ol (2), and 10-bromo-3-chlorocupar-5-en-2-ol (3), one new C12-acetogenin, desepilaurallene (7), one new naturally occurring sesquiterpene, 7-hydroxylaurene acetate (4), two known sesquiterpenes, allolaurinterol acetate (5) and laurene (6), and one known C15-acetogenin, epilaurallene (8), were isolated from the marine red alga Laurencia okamurai collected from the coast of Rongcheng, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 4, 5 exhibited potent antibacterial activity, and 1, 4, 5 were toxic to brine shrimp. [Copyright &y& Elsevier]

We report on the chemical characteristics of the red alga Laurencia japonensis, collected off the coast of Yoshio, Katsuura, Boso Peninsula, Japan. We isolated two new brominated C15-acetogenins in this species, which we name katsuurenyne A (1) and katsuurenyne B (2), along with two already known halogenated terpenes [2,10-dibromo-3-chloro-α-chamigrene (7) and aplysiadiol (8)]. We extensively analysed spectral data (from IR, ESI-MS, 1D-NMR and 2D-NMR) to confirm the structure of these compounds. [ABSTRACT FROM AUTHOR]

Biosecurity is emerging as one of the most important issues facing the agricultural and forestry communities, with the use of chemical pesticides being the main protocol for controlling plant pathogens. However, as a result of the emergence of resistance against these controls and the negative impact chemicals have on the environment, coupled with more stringent European Union regulations, this will have to change. The search for safer alternatives has begun, with seaweed becoming an interesting focus as a potential biopesticide due to its ability to produce a broad spectrum of chemically active secondary metabolites. These secondary metabolites possess biological properties including antimicrobial, antioxidant, anti-inflammatory, and antifungal. There is a need to develop reliable methods with the ability to rapidly screen and evaluate the potential pesticidal activity in seaweeds. This review focuses on the current methods used to investigate the fungicidal activity of seaweed extracts including in vitro methods namely disk diffusion and in vivo methods namely, the screen-house study and the advantages and disadvantages associated with each method. It was concluded that no one method is suitable for all test organisms or extracts after careful consideration of the literature. Additionally, this review confirms the promising potential of seaweeds as biopesticides with studies demonstrating that seaweeds are active against a wide variety of fungal diseases. It was noted that further research needs to be carried out on the isolation, purification, and identification of the bioactive compounds present in seaweeds in order to facilitate the future potential application of these novel biopesticides. [ABSTRACT FROM AUTHOR]

Hydroperoxides are a small and interesting group of biologically active natural marine compounds. All these metabolites contain a group (R-O-O-H). In this mini-review, studies of more than 80 hydroperoxides isolated from bacteria, fungi, algae, and marine invertebrates are described. Hydroperoxides from the red, brown, and green algae exhibit high antineoplastic, anti-inflammatory, and antiprotozoal activity with a confidence of 73 to 94%. Hydroperoxides produced by soft corals showed antineoplastic and antiprotozoal activity with confidence from 81 to 92%. Metabolites derived from sea sponges, mollusks, and other invertebrates showed antineoplastic and antiprotozoal (Plasmodium) activity with confidence from 80 to 90%. [ABSTRACT FROM AUTHOR]

Cyanobacteria are found globally due to their adaptation to various environments. The occurrence of cyanobacterial blooms is not a new phenomenon. The bloom-forming and toxin-producing species have been a persistent nuisance all over the world over the last decades. Evidence suggests that this trend might be attributed to a complex interplay of direct and indirect anthropogenic influences. To control cyanobacterial blooms, various strategies, including physical, chemical, and biological methods have been proposed. Nevertheless, the use of those strategies is usually not effective. The isolation of natural compounds from many aquatic and terrestrial plants and seaweeds has become an alternative approach for controlling harmful algae in aquatic systems. Seaweeds have received attention from scientists because of their bioactive compounds with antibacterial, antifungal, anti-microalgae, and antioxidant properties. The undesirable effects of cyanobacteria proliferations and potential control methods are here reviewed, focusing on the use of potent bioactive compounds, isolated from seaweeds, against microalgae and cyanobacteria growth. [ABSTRACT FROM AUTHOR]

Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C15 acetogenin medium-ring ethers. Here, we described the isolation of three new C15 acetogenins (3-5), and one truncated derivative (6) from Laurencia viridis collected on the Canary Islands. These compounds are interesting variations on the pinnatifidenyne structure that included the first examples of ethynyl oxirane derivatives (3-4). The structures were elucidated by extensive study of NMR (Nuclear Magnetic Resonance) data, J-based configuration analysis and DFT (Density Functional Theory) calculations. Their antiproliferative activity against six human solid tumor cell lines was evaluated. [ABSTRACT FROM AUTHOR]

An unprecedented non-isoprenoid oxocine carboxylate cyclic ether characterised as (3S, 4R, 5S, 6Z)-3-((R)-hexan-2′-yl)-3,4,5,8-tetrahydro-4-methyl-2H-oxocin-5-yl acetate was isolated from the ethyl acetate–methanol extract of the red seaweed Kappaphycus alvarezii. The structure, as well as its relative stereochemistry, was proposed on the basis of extensive spectral data. The antioxidative activity of the isolated metabolite was found to have significantly greater as determined by 1, 1-diphenyl-2-picrylhydrazyl and 2,2′-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid radical scavenging activities (IC50 ~ 0.3 mg/mL) compared to α-tocopherol (IC50 > 0.6 mg/mL) and was comparable to the synthetic antioxidants butylated hydroxytoluene and butylated hydroxyanisole (IC50 ~ 0.35–0.34 mg/mL). The compound exhibited greater activity against COX-2 (cyclooxygenase-2) than COX-1 (cyclooxygenase-1) isoform, and therefore, the selectivity index remained significantly lesser (anti-COX-1IC50: anti-COX-2IC50 0.87) than synthetic anti-inflammatory drugs (0.02–0.44). No significant difference of in vivo 5-lipoxidase activity (IC50 0.95 mg/mL) than ibuprofen (IC50 0.93 mg/mL) indicated the potential anti-inflammatory properties of the title compound. [ABSTRACT FROM AUTHOR]

We report on the chemical characteristics of the red alga Laurencia japonensis , collected off the coast of Yoshio, Katsuura, Boso Peninsula, Japan. We isolated two new brominated C 15 -acetogenins in this species, which we name katsuurenyne A ( 1 ) and katsuurenyne B ( 2 ), along with two already known halogenated terpenes [2,10-dibromo-3-chloro-α-chamigrene ( 7 ) and aplysiadiol ( 8 )]. We extensively analysed spectral data (from IR, ESI-MS, 1D-NMR and 2D-NMR) to confirm the structure of these compounds.

Two new C 15 -acetogenins, 4- epi -isolaurallene ( 1 ) and 4- epi -itomanallene A ( 2 ) were isolated from a population of marine red alga Laurencia nangii Masuda from Carrington Reef. The structures of these compounds were determined intensively by NMR and HRESIMS data. Their configurations were elucidated by detailed comparison of chemical shifts, germinal protons splitting and NOE correlations with known and synthesized analogues. In addition, antibacterial activities of these compounds were evaluated. These compounds would serve as diastereomeric models for future reference. Since the isolaurallene, neolaurallene, 9-acetoxy-1,10,12-tribromo-4,7:6,13-bisepoxypentadeca-1,2-diene, itomanallene A and laurendecumallene A were isolated, compounds 1 and 2 were the sixth example of C 15 -acetogenin with dioxabicyclo[7.3.0]dodecene skeleton.

In addition to 13 known compounds, four new bisabolane sesquiterpenes, okamurenes A-D (1-4), a new chamigrane derivative, okamurene E (5), and a new C12-acetogenin, okamuragenin (6), were isolated from the marine red alga Laurencia okamurai. The structures of these compounds were determined through detailed spectroscopic analyses. Of these, okamurenes A and B (1 and 2) are the first examples of bromobisabolane sesquiterpenes possessing a phenyl moiety among Laurencia-derived sesquiterpenes, while okamuragenin (6) was the first acetogenin aldehyde possessing a C12-carbon skeleton. Each of the isolated compounds was evaluated for the brine shrimp (Artemia salina) lethal assay and 7-hydroxylaurene displayed potent lethality with LD50 1.8 µM. [ABSTRACT FROM AUTHOR]

Specimens of the cosmopolitan sea hare Aplysia parvula , collected in the Tsistsikamma National Park on the south-east coast of South Africa yielded the new dibromo-C15-acetogenin, (3 Z )-bromofucin ( 1 ). Standard spectroscopic methods were used to establish the structure of this compound. [ABSTRACT FROM AUTHOR]

Macroalgae are the source of many harmful allelopathic compounds, which are synthesized as a defense strategy against competitors and herbivores. Therefore, it can be predicted that certain species reduce aquaculture performance. Herein, the allelopathic ability of 123 different taxa of green, red, and brown algae have been summarized based on literature reports. Research on macroalgae and their allelopathic effects on other animal organisms was conducted primarily in Australia, Mexico, and the United States. Nevertheless, there are also several scientific reports in this field from South America and Asia; the study areas in the latter continents coincide with areas where aquaculture is highly developed and widely practiced. Therefore, the allelopathic activity of macroalgae on coexisting animals is an issue that is worth careful investigation. In this work, we characterize the distribution of allelopathic macroalgae and compare them with aquaculture locations, describe the methods for the study of macroalgal allelopathy, present the taxonomic position of allelopathic macroalgae and their impact on coexisting aquatic competitors (Cnidaria) and herbivores (Annelida, Echinodermata, Arthropoda, Mollusca, and Chordata), and compile information on allelopathic compounds produced by different macroalgae species. This work gathers the current knowledge on the phenomenon of macroalgal allelopathy and their allelochemicals affecting aquatic animal (competitors and predators) worldwide and it provides future research directions for this topic. [ABSTRACT FROM AUTHOR]

The exponential growth of emerging multidrug-resistant microorganisms, including foodborne pathogens affecting the shelf-life and quality of foods, has recently increased the needs of the food industry to search for novel, natural and eco-friendly antimicrobial agents. Macroalgae are a bio-diverse group distributed worldwide, known to produce multiple compounds of diverse chemical nature, different to those produced by terrestrial plants. These novel compounds have shown promising health benefits when incorporated into foods, including antimicrobial properties. This review aims to provide an overview of the general methods and novel compounds with antimicrobial properties recently isolated and characterized from macroalgae, emphasizing the molecular pathways of their antimicrobial mechanisms of action. The current scientific evidence on the use of macroalgae or macroalgal extracts to increase the shelf-life of foods and prevent the development of foodborne pathogens in real food products and their influence on the sensory attributes of multiple foods (i.e., meat, dairy, beverages, fish and bakery products) will also be discussed, together with the main challenges and future trends of the use of marine natural products as antimicrobials. [ABSTRACT FROM AUTHOR]

Analysis of the air-dried marine red alga Laurencia papillosa, collected near Ras-Bakr at the Suez gulf (Red Sea) in Egypt delivered five new halogenated terpene derivatives: aplysiolic acid (1), 7-acetyl-aplysiol (2), aplysiol-7-one (3), 11,14-dihydroaplysia-5,11,14,15-tetrol (5a), and a new maneonene derivative 6, named 5-epi-maneolactone. The chemical structures of these metabolites were characterized employing spectroscopic methods, and the relative and absolute configurations were determined by comparison of experimental and ab initio-calculated NMR, NOE, ECD, and ORD data, and by X-ray diffraction of 2 and 6. The antimicrobial activities of the crude extract and compounds 1–3, 5a and 6 were studied. [ABSTRACT FROM AUTHOR]

Seaweeds have received huge interest in recent years given their promising potentialities. Their antioxidant, anti-inflammatory, antitumor, hypolipemic, and anticoagulant effects are among the most renowned and studied bioactivities so far, and these effects have been increasingly associated with their content and richness in both primary and secondary metabolites. Although primary metabolites have a pivotal importance such as their content in polysaccharides (fucoidans, agars, carragenans, ulvans, alginates, and laminarin), recent data have shown that the content in some secondary metabolites largely determines the effective bioactive potential of seaweeds. Among these secondary metabolites, phenolic compounds feature prominently. The present review provides the most remarkable insights into seaweed research, specifically addressing its chemical composition, phytopharmacology, and cosmetic applications. [ABSTRACT FROM AUTHOR]

Fungal sensitization is very common in bronchial asthmatic cases, and the connection with airway colonization by fungi remains uncertain. Antifungal therapy failure is a significant fraction of the cost and morbidity and mortality in the majority of the asthmatic cases. Hence, the present study aimed to investigate the antifungal activity of five marine macroalgae—Acanthaophora specifera, Cladophoropsis sp., Laurencia paniculata, Tydemania sp., and Ulva prolifera—which were tested on selected fungal pathogens isolated from 15 sputum of 45 bronchial asthmatic patients. The highest antifungal activity was observed in ethanol fractions of L. paniculata followed by U. prolifera, Cladophoropsis sp., A. specifera, and Tydemania sp. The minimum fungicidal concentration and minimum inhibitory concentration values of the ethanolic fractions of algal species were found to be 125–1000 µg/mL and 125–500 µg/mL, respectively. The algal extracts contained terpene alcohol, diterpene, steroids, sesquiterpene, and sesquiterpene alcohol, as determined by GC–MS/MS analyses. The present study shows that the marine macroalgae containing bioactive compounds had excellent inhibitory activity against a variety of fungal pathogens, which may be useful for combating fungal infections and recovering from chronic asthmatic states. [ABSTRACT FROM AUTHOR]

In connection with our chemotaxonomic studies of Malaysian species of the red algal genus Laurencia, the chemical composition of Laurencia pannosa Zanardini was examined. Two halogenated sesquiterpenoids, named pannosanol (1) and pannosane (2), have been isolated along with a halogenated C15-acetogenin, (3Z)-chlorofucin (3). The structures of these compounds were determined from their spectroscopic data (IR, 1H NMR, 13C NMR, 2D NMR, and MS). Pannosanol and pannosane are novel halometabolites with an unusual rearranged chamigrane framework. Antibacterial activities of these metabolites against marine bacteria are also described.