Marine Sponge Haliclona Sp Research Articles

Antiproliferative and pro-apoptotic properties against colon carcinoma cell line of the marine sponge haliclona sp. From poblacion, kauswagan, lanao del norte, Philippines

Marine sponge Haliclona sp. was examined for its anticancer potential focusing on the antiproliferative and pro-apoptotic properties against HCT116 (colon) cancer cell line. The 16 fractions obtained from Haliclona sp. were subjected to antiproliferative and pro-apoptotic evaluation via MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay and Caspase-Glo 3/7 assay, respectively, at 30 μg/mL concentration. Fractions 10, 13, 14, and 15 exhibited a significant decrease (p < 0> 50�ll viability) against HCT116. Only fraction 8 showed a significant increase (p < 0.05) in relative light unit (RLU) and fold change (FC) (1809.78 and 2.42), more than two times larger, compared to the negative control (754.89 RLU and 1.00 FC). This result demands further study on fraction 8 to identify and characterize the structure of the compounds responsible for its bioactivity and hence could be a source of drug leads.

Isoquinolinequinone Derivatives from a Marine Sponge (Haliclona sp.) Regulate Inflammation in In Vitro System of Intestine

Using bio-guided fractionation and based on the inhibitory activities of nitric oxide (NO) and prostaglandin E2 (PGE2), eight isoquinolinequinone derivatives (1–8) were isolated from the marine sponge Haliclona sp. Among these, methyl O-demethylrenierate (1) is a noble ester, whereas compounds 2 and 3 are new O-demethyl derivatives of known isoquinolinequinones. Compound 8 was assigned as a new 21-dehydroxyrenieramycin F. Anti-inflammatory activities of the isolated compounds were tested in a co-culture system of human epithelial Caco-2 and THP-1 macrophages. The isolated derivatives showed variable activities. O-demethyl renierone (5) showed the highest activity, while 3 and 7 showed moderate activities. These bioactive isoquinolinequinones inhibited lipopolysaccharide and interferon gamma-induced production of NO and PGE2. Expression of inducible nitric oxide synthase, cyclooxygenase-2, and the phosphorylation of MAPKs were down-regulated in response to the inhibition of NF-κB nuclear translocation. In addition, nuclear translocation was markedly promoted with a subsequent increase in the expression of HO-1. Structure-activity relationship studies showed that the hydroxyl group in 3 and 5, and the N-formyl group in 7 may be key functional groups responsible for their anti-inflammatory activities. These findings suggest the potential use of Haliclona sp. and its metabolites as pharmaceuticals treating inflammation-related diseases including inflammatory bowel disease.

X-ray Crystallography and Unexpected Chiroptical Properties Reassign the Configuration of Haliclonadiamine.

Haliclonadiamine and papuamine are bis-indane marine natural products isolated from the marine sponge Haliclona sp. Their relative structures were previously reported to differ by inversion at only one of their eight shared stereocenters. Here X-ray crystallography shows the opposite to be true: papuamine has a 1R,3S,8R,9S,14S,15R,20S,22R configuration, while haliclonadiamine has a 1S,3R,8S,9R,14R,15S,20R,22R configuration. Paradoxically the ECD of each structure displays a negative Cotton effect. X-ray crystallography reveals the two structures adopt similar conformations of their 13-membered macrocyclic core that comprises a configurationally relevant diene. B97x-D/Def2-TZVPP-(MeOH)-calculated ECD supports the diene configuration with the macrocycle dominating the ECD Cotton effect for haliclonadiamine and papuamine. Additional crystallographic and chiroptical analyses of three sponge samples from geographically distant locations indicate this pair of natural products always exists as a configurationally related couple. The co-discovery of a biosynthetic precursor, halichondriamine C, present in these same Haliclona samples must be considered when discussing any biosynthetic pathway. Taken together, this work justifies a reassignment of haliclonadiamine's structure and opens the question of how this complex stereochemical relationship between haliclonadiamine and palauamine arises biosynthetically.

Two New Phthalate Derivatives from the Marine Sponge Haliclona sp.

Two new phthalate derivatives, N1-(2-aminoethyl)-N2-isopentylphthalamide (1) and N1-isobuty-N2-tridecylphthalamide (2), were isolated from the marine sponge Haliclona sp. The structures of the new isolates were elucidated on the basis of extensive spectroscopic analysis and by comparison of the data with those of related secondary metabolites.

Anti-mycobacterial alkaloids, cyclic 3-alkyl pyridinium dimers, from the Indonesian marine sponge Haliclona sp.

Three new dimeric 3-alkyl pyridinium alkaloids, named haliclocyclamines A–C (1–3), were isolated together with five known congeners, cyclostellettamines A (4), B (5), C (6), E (7), and F (8), from the Indonesian marine sponge Haliclona sp. The structures of 1–3 were assigned based on their spectroscopic data (1D and 2D NMR, HRFABMS, ESIMS/MS, UV, and IR). Compounds 1–8 exhibited antimicrobial activities against Mycobacterium smegmatis with inhibition zones of 17, 10, 13, 14, 8, 8, 12, and 12mm, respectively, at 10μg/disc. Compounds 3 and 8 also modestly inhibited the activity of vaccinia H-1-related phosphatase (VHR), a dual-specificity phosphatase, at 17–18μM.

A new 3-alkylpyridine alkaloid from the marine sponge Haliclona sp. and its cytotoxic activity

A new alkaloid, 3-dodecyl pyridine containing a terminal cyano group (1), was isolated from the methanol extract of an Indonesia marine sponge Haliclona sp. Its chemical structure was determined by a combination of spectroscopic methods, including 1D and 2D NMR. Bioassay results indicated that compound 1 had moderate cytotoxity against tumour cell lines A549, MCF-7 and Hela with IC50 values of 41.8, 48.4 and 33.2 μM, respectively.

Three new polyunsaturated lipids from a Guangxi marine sponge Haliclona sp.

Three new polyunsaturated lipids, (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-3-one (1), (6Z,9Z,12Z,15Z)-1-bromooctadeca-6,9,12,15-tetraen-3-one (2), and (Z)-ethyl docos-5-enoate (3), together with two known polyunsaturated lipids, 4(Z),7(Z),10(Z)-tridecatrienoic acid (4) and (6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-one (5), were isolated from the marine sponge Haliclona sp., which was collected from Guangxi, using HSCCC and HPLC methods. Chemical structures of the five compounds were elucidated by spectroscopic techniques.

Cyclic 3-Alkyl Pyridinium Alkaloid Monomers from a New Zealand Haliclona sp. Marine Sponge

Bioassay and NMR approaches have been used to guide the isolation of one known and two new cyclic 3-alkyl pyridinium alkaloid (3-APA) monomers from the New Zealand marine sponge Haliclona sp. The new compounds, dehydrohaliclocyclins C (3) and F (4), are the first reported examples of cyclic 3-APA monomers with unsaturation in the alkyl chain. The known compound haliclocyclin C (2) was also isolated from a mixture with 4. The structures of compounds 2-4 were elucidated using NMR spectroscopy, mass spectrometry, and chemical degradation.

Diversity of bacteria and polyketide synthase associated with marine sponge Haliclona sp.

The microbial community associated with a marine sponge (Haliclona sp.) collected from Tateyama city, Japan was studied using 16S rRNA gene clone libraries. Two DNA templates were prepared using methods recommended for Gram-positive and Gram-negative bacteria in the Qiagen kit manual. From each DNA template, two 16S rRNA genes were PCR amplified, using the combination of universal bacterial primer 27f and primers 1385r and 1492r, respectively. A total of 347 clones were sequenced and compared with those available in DNA data banks. These sequences were members of ten bacterial phyla. Interestingly, more than 30 % of the clones represent novel sequences. A comparison of these sequences with sequences in a library prepared from DNA extracted from the surrounding water shows minimum DNA contamination. Taxonomically, the highest diversity was detected in the clone library prepared using a combination of primers 27f and 1492r and DNA isolated using the Gram-positive bacteria protocol. The potential of Haliclona sp.-associated bacteria to produce secondary metabolites was studied by cloning and sequencing the polyketide synthase (PKS, type 1) gene using the same DNA samples. Analysis of partial sequences derived from the sponge metagenome revealed 27 unique ketosynthase domains of PKS type I. This study suggests strongly that this Haliclona sp. plays host to diverse novel bacteria with a potential to produce novel polyketides.

Streptomyces tateyamensis sp. nov., Streptomyces marinus sp. nov. and Streptomyces haliclonae sp. nov., isolated from the marine sponge Haliclona sp.

Three Gram-positive, NaCl-requiring actinobacteria were isolated from a marine sponge, Haliclona sp., collected from the coast of Tateyama City, Japan. Comparison of 16S rRNA gene sequences indicated that these strains represent novel members of the genus Streptomyces, exhibiting low 16S rRNA gene sequence similarities of 98.3-97.4 % with recognized members of the genus. The cell hydrolysates contained the LL-isomer of diaminopimelic acid and the predominant quinones were MK-9 (H(6) and/or H(8)). The DNA G+C contents were in the range 72-75mol%. A polyphasic study of the strains and comparison of the characters with related species of the genus show that these strains represent three novel species of the genus Streptomyces. Therefore, the names Streptomyces tateyamensis sp. nov., Streptomyces haliclonae sp. nov. and Streptomyces marinus sp. nov. are proposed for strains Sp080513SC-30(T) (=NBRC 105048(T) =DSM 41969(T)), Sp080513SC-31(T) (=NBRC 105049(T) =DSM 41970(T)) and Sp080513GE-26(T) (=NBRC 105047(T) =DSM 41968(T)), respectively.

Nucleosides from the Marine Sponge Haliclona sp.

Three known nucleosides were isolated from the sponge Haliclona sp. The structures were established on the basis of NMR data and comparison with those reported, and chemotaxonomic relationships of the sponge nucleosides were discussed.

2-Palmitamidoethanesulfonic acid, a taurine derivative from the marine sponge Haliclona sp.

[Wang, Bin; Zhang, Si; Liu, Yonghong] Chinese Acad Sci, Key Lab Marine Bioresources Sustainable Utilizat, S China Sea Inst Oceanol, Guangzhou 510301, Guangdong, Peoples R China; [Wang, Bin] Beihua Univ, Jilin 132001, Peoples R China; [Lee, Kyung Jin] Hannam Univ, Dept Biol, Taejon, South Korea; [Jung, Jee H.] Pusan Natl Univ, Coll Pharm, Pusan 609735, South Korea

Renierosides, Cerebrosides from a Marine Sponge Haliclona (Reniera) sp.

Guided by the brine shrimp lethality assay, eight new cerebrosides (1-8) have been isolated from an extract of the marine sponge Haliclona (Reniera) sp. A novel feature of these cerebrosides was the presence of unprecedented amide-linked long-chain fatty acid moieties. The planar structures of the cerebrosides (1-8) were established by 1D and 2D NMR spectroscopic techniques, mass spectrometric analyses, and chemical degradation methods. The isolated compounds did not display cytotoxicity to a panel of five human solid tumor cell lines.

Diversity of culturable actinobacteria isolated from marine sponge Haliclona sp.

This study describes actinobacteria isolated from the marine sponge Haliclona sp. collected in shallow water of the South China Sea. A total of 54 actinobacteria were isolated using media selective for actinobacteria. Species diversity and natural product diversity of isolates from marine sponge Haliclona sp. were analysed. Twenty-four isolates were selected on the basis of their morphology on different media and assigned to the phylum Actinobacteria by a combination of 16S rRNA gene based restriction enzymes digestion and 16S rRNA gene sequence analysis. The 16S rRNA genes of 24 isolates were digested by restriction enzymes TaqI and MspI and assigned to different groups according to their restriction enzyme pattern. The phylogenetic analysis based on 16S rRNA gene sequencing showed that the isolates belonged to the genera Streptomyces, Nocardiopsis, Micromonospora and Verrucosispora; one other isolate was recovered that does not belong to known genera based on its unique 16S rRNA gene sequence. To our knowledge, this is the first report of a bacterium classified as Verrucosispora sp. that has been isolated from a marine sponge. The majority of the strains tested belong to the genus Streptomyces and three isolates may be new species. All of the 24 isolates were screened for genes encoding polyketide synthases (PKS) and nonribosomal peptide synthetases (NRPS). PKS and NRPS sequences were detected in more than half of the isolates and the different "PKS-I-PKS-II-NRPS" combinations in different isolates belonging to the same species are indicators of their potential natural product diversity and divergent genetic evolution.

Hexaprenoid Hydroquinones from the Sponge Haliclona (aka Adocia) sp.

Three new hexaprenoid hydroquinones, adociaquinol (1), adociasulfate 11 (2), and adociasulfate 12 (3), together with the known adociasulfates 2, 4, and 6, were isolated from the marine sponge Haliclona (aka Adocia) sp. The structures of these compounds were elucidated by interpretation of spectroscopic data.

A new pentacyclic sulfated hydroquinone from the marine sponge Haliclona sp.

A new pentacyclic sulfated hydroquinone, phuklona sulfate, has been isolated from the marine sponge Haliclona sp. collected near Phuket Island, Thailand. The structure was elucidated by a variety of spectroscopic methods including 1D and 2D NMR experiments. Phuklona sulfate contains a novel triterpenoid carbon skeleton linked to a sulfated hydroquinone moeity.

Halipeptins A and B: two novel potent anti-inflammatory cyclic depsipeptides from the Vanuatu marine sponge Haliclona species.

Two new metabolites, named halipeptins A and B, have been isolated from the marine sponge Haliclona sp. Their structures were determined by extensive use of one- and two-dimensional NMR experiments, mass spectrometry, and UV and IR spectroscopy. Halipeptin A is a novel 17-membered cyclic depsipeptide, consisting of five residues including two alanines (with L stereochemistry) and three new residues that appear to be previously undescribed from natural sources: 1,2-oxazetidine-4-methyl-4-carboxylic acid, 3-hydroxy-2,2,4-trimethyl-7-methoxydecanoic acid (HTMMD), and N-methyl-delta-hydroxyisoleucine. The HTMMD residue is substituted with 3-hydroxy-2,2,4-trimethyl-7-hydroxydecanoic acid in halipeptin B. Halipeptin A was found to possess very potent anti-inflammatory activity in vivo, causing about 60% inhibition of edema in mice at the dose of 300 microg/kg (i.p.).

A new isoquinoline alkaloid from the marine sponge Haliclona species.

Two isoquinoline alkaloids, including the new compound 1, were isolated from the cytotoxic fractions of an aqueous extract of the marine sponge Haliclona sp. The structures of these compounds were established as 1-hydroxymethyl-7-methoxyisoquinolin-6-ol (1) and mimosamycin (2) by conventional spectroscopic methods and by comparison with related compounds. Mimosamycin (2) was the principal cytotoxin with an IC(50) of approximately 10 microg/mL against melanoma and ovarian human tumor cell lines.

Haliclamide, a novel cyclic metabolite from the Vanuatu marine sponge Haliclona sp.

A new cyclic metabolite, named haliclamide ( 1), has been isolated from the Vanuatu marine sponge Haliclona sp. Its structure was determined from 1D and 2D NMR studies and mass spectral data. Haliclamide ( 1) represents a new 16-membered cyclic depsipeptide containing, along with a N-methylphenylalanine, two residues never isolated from natural sources: 5-hydroxy-octanoic acid (HOA) and 6-amino-7-hydroxy-2-methylheptanoic acid (AHMA). Haliclamide ( 1) exhibited cytotoxicity against the NSCLC-N6 human bronchopulmonary non-small-cell-lung carcinoma cell lines with an IC 50 value of 4.0 μg/mL.

Apicularens A and B, new cytostatic macrolides from Chondromyces species (myxobacteria): production, physico-chemical and biological properties.

A novel macrolide, apicularen A, was produced by several species of the genus Chondromyces. Initially it was discovered by bioassay-guided RP-HPLC-fractionation of culture extracts of Chondromyces robustus, strain Cm a13. Apicularen A showed no antimicrobial activity, but was highly cytotoxic for cultivated human and animal cells, with IC50 values ranging between 0.1 and 3 ng/ml. A cometabolite of apicularen A, the N-acetylglucosamine glycoside apicularen B, was distinctly less cytotoxic with IC50 values between 0.2 and 1.2 microg/ml, and showed weak activity against a few Gram-positive bacteria. Apicularen A is chemically closely related to the salicylihalamides A and B from the marine sponge Haliclona sp.