Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus .

A new psammaplysin derivative, ceratinadin G (), was obtained from the Okinawan marine sponge sp., and the gross structure was clarified through spectroscopic and spectrometric analyses. The absolute configuration of compound was established by comparing its NMR and ECD data with those of the known psammaplysin derivative, psammaplysin F ().

Evaluating the activity of N-89 as an oral antimalarial drug.

Despite the recent progress in public health measures, malaria remains a troublesome disease that needs to be eradicated. It is essential to develop new antimalarial medications that are reliable and secure. This report evaluated the pharmacokinetics and antimalarial activity of 1,2,6,7-tetraoxaspiro[7.

Zamamiphidins B and C, Manzamine-Related Alkaloids from an sp. Marine Sponge Collected in Okinawa.

Zamamiphidins B () and C (), two new manzamine-related alkaloids with an unprecedented fused diazahexacyclic ring system, were isolated from an sp. marine sponge collected in Okinawa. The structures of zamamiphidins B () and C () including the relative configurations were elucidated on the basis of spectroscopic data.

Integrated omics unveil the secondary metabolic landscape of a basal dinoflagellate.

Background: Some dinoflagellates cause harmful algal blooms, releasing toxic secondary metabolites, to the detriment of marine ecosystems and human health. Our understanding of dinoflagellate toxin biosynthesis has been hampered by their unusually large genomes. To overcome this challenge, for the first time, we sequenced the genome, microRNAs, and mRNA isoforms of a basal dinoflagellate, Amphidinium gibbosum, and employed an integrated omics approach to understand its secondary metabolite biosynthesis.

Macrocarquinoids A-C, new meroterpenoids from Sargassum macrocarpum.

The production and accumulation of advanced glycation end products (AGEs) have been implicated in diabetes and diabetic complication. This study was conducted as a search for an AGE inhibitor from brown alga, Sargassum macrocarpum. Separation and purification were performed using AGEs inhibitory activity as an index, yielding isolation of 11 meroterpenoids, of which 3 were new compounds: macrocarquinoids A (1), B (6), and C (9).

Kamiohnoyneosides A and B, two new polyacetylene glycosides from flowers of edible Chrysanthemum "Kamiohno".

Two new polyacetylene glycosides, kamiohnoyneosides A and B, were isolated from the flowers of edible Chrysanthemum "Kamiohno", along with a known polyacetylene glycoside and two known monoterpene glycosides. The structures of new compounds were elucidated on the basis of spectroscopic data. Kamiohnoyneoside A and three known compounds moderately inhibited formation of N-(carboxymethyl)lysine, one of the representative advanced glycation endproducts.

The manzamine alkaloids.

The manzamine alkaloids are absolutely one of the most fascinating marine natural products. The representative manzamine alkaloids, manzamines A-C, were isolated from a marine sponge Haliclona sp. collected off Cape Manzamo, Okinawa, Japan.

Ma'edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge sp.

Two new bromotyrosine alkaloids, ma'edamines C and D, were isolated from an Okinawan marine sponge sp. The structures of ma'edamines C and D were elucidated on the basis of spectroscopic data. Ma'edamines C and D were the first natural products possessing a unique tetrasubstituted pyridinium moiety such as -alkyl-3,5-diethyl-2-propylpyridinium and -alkyl-3,5-diethyl-4-propylpyridinium, respectively.

Ceratinadins E and F, New Bromotyrosine Alkaloids from an Okinawan Marine Sponge sp.

Two new bromotyrosine alkaloids, ceratinadins E () and F (), were isolated from an Okinawan marine sponge sp. as well as a known bromotyrosine alkaloid, psammaplysin F (). The gross structures of and were elucidated on the basis of spectroscopic data.

New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.

The investigation of the Vietnamese marine sponge Spongia sp. led to the isolation of three new sesquiterpene phenols, langconols A-C (1-3), and one new sesquiterpene hydroxyquinone, langcoquinone C (4), together with two known meroterpenoids (5 and 6). Their structures were determined on the basis of spectroscopic analyses and comparisons with published data.

Zamamidine D, a Manzamine Alkaloid from an Okinawan Amphimedon sp. Marine Sponge.

A new manzamine alkaloid, zamamidine D (1), was isolated from an Okinawan Amphimedon sp. marine sponge. The structure of zamamidine D (1) including the relative configuration was elucidated on the basis of spectroscopic data.

Biosynthetic Study of Amphidinin A and Amphidinolide P.

The biogenetic origins of amphidinin A (1) and amphidinolide P (2) were investigated by feeding experiments with (13)C-labeled acetates. (13)C-NMR data of (13)C-enriched samples revealed that the all carbons of 1 and 2 were derived from acetates. The polyketide chain of 1 was formed from one triketide chain, two diketide chains, and three unusual isolated C1 units derived from C-2 of cleaved acetates, while the polyketide chain of 2 was formed from one pentaketide chain, two acetate units, and three unusual isolated C1 units derived from C-2 of cleaved acetates.

Hyrtinadines C and D, New Azepinoindole-Type Alkaloids from a Marine Sponge Hyrtios sp.

New bisindole alkaloids, hyrtinadines C (1) and D (2), have been isolated from an Okinawan marine sponge Hyrtios sp. The structures of hyrtinadines C (1) and D (2) were elucidated based on analyses of the spectral data. Hyrtinadines C (1) and D (2) were the relatively rare alkaloids possessing a 3,4-fused azepinoindole skeleton.

Enantioselective Utilization of D-Amino Acids by Deep-Sea Microorganisms.

Microorganisms that utilize various D-amino acids (DAAs) were successfully isolated from deep-sea sediments. The isolates were phylogenetically assigned to Alphaproteobacteria, Gammmaproteobacteria, and Bacilli. Some of the isolates exhibited high enantioselective degradation activities to various DAAs.

Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis.

The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP "linchpin" as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16.

Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part I: Synthesis of the C1-C13 Subunit.

Amphidinolide N, the structure of which has been recently revised, is a 26-membered macrolide featuring allyl epoxide and tetrahydropyran moieties with 13 chiral centers. Due to its challenging structure and extraordinary potent cytotoxicity, amphidinolide N is a highly attractive target of total synthesis. During our total synthesis studies of the 7,10-epimer of the proposed structure of amphidinolide N, we have synthesized the C1-C13 subunit enantio- and diastereoselectively.

sp. nov., an anaerobic, amino-acid-utilizing bacterium isolated from marine subsurface sediment.

A novel, anaerobic bacterium, strain MO-SEDI, was isolated from a methanogenic microbial community, which was originally obtained from marine subsurface sediments collected from off the Shimokita Peninsula of Japan. Cells were Gram-stain-negative, non-motile, non-spore-forming rods, 0.4-1.

Distribution of eukaryotic serine racemases in the bacterial domain and characterization of a representative protein in Roseobacter litoralis Och 149.

Two distinct bacterial and eukaryotic serine racemases (SRs) have been identified based on phylogenetic and biochemical characteristics. Although some reports have suggested that marine heterotrophic bacteria have the potential to produce d-serine, the gene encoding bacterial SRs is not found in those bacterial genomes. In this study, using in-depth genomic analysis, we found that eukaryotic SR homologues were distributed widely in various bacterial genomes.

Tyrokeradines G and H, new bromotyrosine alkaloids from an Okinawan Verongid sponge.

Two new bromotyrosine alkaloids, tyrokeradines G (1) and H (2), have been isolated from an Okinawan marine sponge of the order Verongida. The structures of 1 and 2 were elucidated on the basis of spectroscopic data. Tyrokeradine G (1) is the first bromotyrosine alkaloid possessing a β-alanine unit, while tyrokeradine H (2) is a rare bromotyrosine alkaloid possessing a N-substituted pyridinium ring.

Biochemical and genetic characterization of β-1,3 glucanase from a deep subseafloor Laceyella putida.

A β-1,3-glucanase (LpGluA) of deep subseafloor Laceyella putida JAM FM3001 was purified to homogeneity from culture broth. The molecular mass of the enzyme was around 36 kDa as judged by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). LpGluA hydrolyzed curdlan optimally at pH 4.

Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis.

Speradine A is a derivative of cyclopiazonic acid (CPA) found in culture of an Aspergillus tamarii isolate. Heterologous expression of a predicted methyltransferase gene, cpaM, in the cpa biosynthesis gene cluster of A. tamarii resulted in the speradine A production in a 2-oxoCPA producing A.

Iejimalide C is a potent V-ATPase inhibitor, and induces actin disorganization.

Iejimalides (IEJLs) A-D are 24-membered macrolides isolated from a tunicate Eudistoma cf. rigida, and exhibit potent cytotoxicity in vitro and antitumor activity in vivo. We previously reported that the molecular target of IEJL-A and -B was the vacuolar-type H(+)-ATPases (V-ATPases).

Amphidinins C-F, amphidinolide Q analogues from marine dinoflagellate Amphidinium sp.

Four new polyketides, amphidinins C-F (1-4), have been isolated from the culture broth of symbiotic dinoflagellate Amphidinium sp. The analysis of their spectral data revealed that amphidinins C-F (1-4) were 4,5-seco-analogues of amphidinolide Q (5). The absolute configurations of the new compounds were elucidated by the combination of J-based configuration analysis, modified Mosher's method, and chemical derivatization.

Predictive factors related to the efficacy of pelvic arterial embolization for postpartum hemorrhage: a retrospective analysis of 21 cases.

Objective: This retrospective study aimed to determine the predictive factors for the efficacy of pelvic arterial embolization for postpartum hemorrhage.

Materials And Methods: Twenty-one patients who underwent pelvic arterial embolization for postpartum hemorrhage of >1000 mL between September 2006 and September 2011 were enrolled in this study. The patients were divided into two subgroups according to the blood loss and time from the end of pelvic arterial embolization to complete hemostasis: good-response (16 patients) and poor-response groups (5 patients).