A non-peroxide norsesterterpene from a marine sponge Hyrtios erecta

A new norsesterterpene, hyrtial 4, and known sesterterpenes, 1-3, have been isolated from an anti-inflammatory active crude extract of the sponge Hyrtios erecta.     

A novel antagonist of serotonergic receptors,hymenidin, isolated from the Okinawan marine spongeHymeniacidon sp.

Summary A novel bromine-containing pyrrole compound, hymenidin, has been isolated from the Okinawan marine spongeHymeniacidon sp. as a potent antagonist of serotonergic receptors and its structure elucidated using spectral data.     

1,1-Dimethyl-5,6-dihydroxyindolinium chloride from a deep water marine sponge,Dercitus sp.

Summary 1,1-Dimethyl-5,6-dihydroxyindolinium chloride (1a)was identified from a deep water sample of the marine sponge,Dercitus sp., and its structure was elucidated by spectral methods.Acknowledgments. This is Harbor Branch Oceanographic Institution, Inc., SeaPharm Project Contribution No. 612. We thank Drs K. Rinehart, Jr, S. Pomponi and E. Armstrong for sponge collection.     

A new 9,11-secosterol,stellettasterol from a marine spongeStelletta sp

A new 9,11-secosteroid, stellettasterol (1) was isolated from a Japanese marine sponge,Stelletta sp.; its structure was determined by spectroscopic analysis. All NMR signals of1 were unambiguously assigned by application of various 2D NMR techniques. Stellettasterol exhibited antifungal activity againstMortieralla ramannianus.Part 62 of the Bioactive Marine Metabolites series. Part 61: Fusetani, N., Takahashi, M., and Matsunaga, S., Tetrahedron, in press.     

Plakorin,a potent Ca2+-ATPase activator from the Okinawan marine spongePlakortis sp.

Summary A new cyclic peroxide, plakorin, which is a potent sarcoplasmic reticulum (SR) Ca^a+-ATPase activator has been isolated from the Okinawan marine spongePlakortis sp., its structure was elucidated on the basis of spectral data.Acknowledgments. We thank Ms M. Hamashima and Ms A. Muroyama for their technical assistance.     

Novel diterpenoid diacylglycerols from marine molluscs: potent morphogens and protein kinase C activators

Five novel 1,2-sn-diacylglycerols with diterpenoid acyl moieties in thesn-1 position were isolated and characterized, together with the corresponding 1,3-sn-diacylglycerols, from three species of dorid nudibranchs molluscs. Their potent activity as morphogens in vivo in theHydra tentacle regeneration assay and their parallel activity as activators of rat brain protein kinase C (PKC) in vitro are reported here. Our findings promote the use of these compounds as useful molecular probes for both in vivo and in vitro studies on the participation of PKC in cell development.     

Okadaxanthin,a novel C50-carotenoid from a bacterium,Pseudomonas sp. KK10206C associated with marine sponge,Halichondria okadai

To study the origins of biologically active substances in marine sponges, a carotenoid produced by a marine bacterium,Pseudomonas sp. strain number KK10206C, which was associated with a marine sponge,Halichondra okadai, was investigated. A visible absorption spectrum-guided isolation procedure led to the isolation of a novel C₅₀-carotenoid, okadaxanthin. Its structure, 2,2-bis(4-hydroxy-2-methyl-2-butenyl)-,-carotene, was elucidated mainly by spectroscopic methods. Okadaxanthin turned out to be a potent singlet oxygen quencher, approximately 10 times as strong as -tocopherol.     

A potent actomyosin ATPase activator from the Okinawan marine spongeAgelas cf.nemoechinata

Summary A bromine-containing alkaloid, oxysceptrin, has been isolated as a potent actomyosin ATPase activator from the Okinawan marine spongeAgelas cf.nemoechinata, and the structure elucidated to be1 on the basis of the 2D NMR spectral data.Acknowledgments. We thank Mr Z. Nagahama for his help in sponge collecting and Ms M. Takamatsu for her technical assistance.     

Brominated diphenyl ethers from a marine bacterium associated with the spongeDysidea sp.

Summary BacteriaVibro sp. isolated from the spongeDysidea sp. were shown to biosynthesize brominated diphenyl ethers. We identified one of the bacterial brominated metabolites using gas liquid chromatography and mass spectrometry to compare this product with standard 3,5-dibromo-2-(3,5-dibromo-2-methoxyphenoxy)phenol. The latter has been isolated from ethanol extracts of the spongeDysidea sp.     

Polyclinal,a new sulfated polyhydroxy benzaldehyde from the marine ascidianPolyclinum planum

Summary A new sulfated polyhydroxy benzaldehyde has been isolated from extracts of the temperate colonial ascidianPolyclinum planum. The structure of the new metabolite was solved by an X-ray crystallographic study. The highest concentration of this metabolite was found in the zooid-rich outer layers of this ascidian suggesting that it may represent a potential chemical defense against predators.     

Purealidin A,a new cytotoxic bromotyrosine-derived alkaloid from the Okinawan marine spongePsammaplysilla purea

Summary A new bromotyrosine-derived alkaloid with antileukemic activity, purealidin A (5), has been isolated from the Okinawan marine spongePsammaplysilla purea and its chemical structure elucidated on the basis of the spectroscopic data.     

Alarm pheromones from the Mediterranean opisthobranchHaminoea navicula

Summary Structure and absolute stereochemistry of two new 3-alkylpyridines, haminol-A (3) and haminol-B (4), isolated from the cephalaspidean molluscHaminoea navicula, have been determined by means of spectral and chemical methods. Haminols are secreted byH. navicula when it is molested, and these induce an alarm response in trail-following conspecifics.In part presented at the 32nd IUPAC Congress Stockholm, 2–7 August 1989. Cimino, G., and Sodano, G., Abstracts SL 302, p. 63.     

Possible origin of zeaxanthin in the marine sponge,Reniera japonica

As part of a study to clarify the origins of biologically active substances in marine sponges, the carotenoids produced by two species of marine bacteria,Flexibacter sp. strain number DK30213 and DK30223, associated with the marine sponge,Reniera japonica, were investigated. Both bacteria were found to produce zeaxanthin [(3R, 3R)-dihydroxy-,-carotene] which is widely distributed in marine organisms. This carotenoid was also detected in the host sponge, suggesting the transport of zeaxanthin from the microorganisms to the host. As zeaxanthin plays the role of a quencher and scavenger for active species of oxygen, it is presumed that the sponge accumulates the bacterial product as a defense substance against the active oxygen species produced under irradiation by strong sunlight. It is thought that the bacteria are symbionts of the host sponge and act by obtaining the solid substrate and medium needed for settlement and growth from the host, and by producing and transmitting the biologically active substance to the host. Zeaxanthin-producing bacteria are also considered to have potential for practical uses by the aquacultural, pharmaceutical and food industries.     

Extraordinary levels of cadmium and zinc in a marine sponge,Tedania charcoti Topsent: inorganic chemical defense agents

The Antarctic marine spongeTedania charcoti has been shown to contain extraordinarily high natural concentrations of cadmium and zinc, which have in turn been correlated to the ability of the crude ethanol extract to modulate protein phosphorylation in chicken forebrain and to inhibit the growth of several test bacteria.     

Luffariellolide,an anti-inflammatory sesterterpene from the marine spongeLuffariella sp.

Summary Luffariellolide (2) is a sesterterpene from the Palauan spongeLuffariella sp. that has useful anti-inflammatory properties. In contrast with the irreversible action of manoalide (1) on phospholipase A₂, luffariellolide (2) is a slightly less potent but partially reversible PLA₂ inhibitor.30 December 1986Acknowledgment We thank Edward Luedtke, Elise Clason and Ellen Snideman for performing some of the assays reported above. The sponge was identified by Dr. Klaus Rützler, Smithsonian Institution, Washington, D.C. The research was supported by grants from Allergan Pharmaceuticals and the California Sea Grant College Program (Projects R/MP-30 and R/MP-31).     

Cyanobacterial symbiont biosynthesis of chlorinated metabolites fromDysidea herbacea (Porifera)

The tropical marine spongeDysidea herbacea contains large numbers of a symbiotic filamentous cyanobacterium identified on the basis of a detailed ultrastructural study asOscillatoria spongeliae. We report the flow-cytometric separation of the symbiont from the sponge cells, and demonstrate by chemical analyses that a unique group of polychlorinated compounds isolated from the whole sponge tissue is limited to the cyanobacterial filaments, whereas the accompanying sesquiterpenoids are found only in the sponge cells. This is the first demonstration that secondary metabolites ascribed to a sponge are localized in prokaryotic symbiont cells.     

Lipopurealins,novel bromotyrosine derivatives with long chain acyl groups,from the marine spongePsammaplysilla purea

Summary Lipopurealin-A,-B and-C have been isolated from the Okinawan marine spongePsammaplysilla purea. They are inhibitors of Na, K-ATPase, and the structures have been elucidated on the basis of spectral data. They are bromotyrosine derived structures with saturated long chain acyl parts.Physiologically active marine natural products from Porifera X. Preceding paper: Nakamura, H., Wu, H., Kobayashi, J., Nakamura, Y., Ohizumi, Y., and Hirata, Y., Tetrahedron Lett.26 (1985) 4517.     

Aragusterol C: A novel halogenated marine steroid from an Okinawan sponge,Xestospongia sp., possessing potent antitumor activity

A novel chlorinated steroid, aragusterol C, was isolated from an Okinawan marine sponge of the genusXestospongia. The compound strongly inhibited the proliferation of KB cells in vitro, and also showed potent in vivo antitumor activity against L1210 cells in mice. The complete structure of aragusterol C was determined by spectroscopic analysis and X-ray crystallographic analysis.     

Bioactive marine metabolites. VIII. Isolation of an antimicrobial blue pigment from the bryozoanBugula dentata

Summary An antimicrobial blue pigment, which is identical with a tetrapyrrole from a bacterium, was isolated from the bryozoanBugula dentata.     

Partial sequence of the gene for a serine protease from a halophilic archaeumhaloferax mediterranei R4, and nucleotide sequences of 16S rRNA encoding genes from several halophilic archaea

A part of the gene coding for a halophilic serine protease from a halophilic archaeumHaloferax mediterranei R4 was amplified by PCR and its 672 nucleotide sequence was determined. Tentative translation to the amino acid sequence suggested that the enzyme was quite similar to halolysin produced by another halophilic archaeum strain 172P1. Nucleotide sequences of 16S rRNA encoding genes from 9 halophilic archaea were determined. Alignment of 19 sequences known so far showed that there are more than 20 positions carrying bases or deletions specific for each halobacterial genus:Halobacterium, Haloarcula, Haloferax, andHalococcus.