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.     

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.     

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.     

Inhibitory effect of bacterial ubiquinones on the settling of barnacle,Balanus amphitrite

In an attempt to clarify the influence of marine bacteria on the settling of fouling invertebrate larvae, we screened for inhibitors, produced by marine bacteria, of settling by cyprids of the barnacle,Balamus amphitrite. We found that the culture broth ofAlteromonas sp. strain number KK10304, which was associated with the marine sponge,Halichondria okadai, effectively inhibited settling of the cyprids. Bioassay-guided isolation indicated ubiquinone-8 (1) as an effective inhibitor of cyprid settling. As ubiquinones are widely distributed in bacteria, several related compounds were also tested.     

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.     

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).     

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.     

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.     

Symbioramide,a novel Ca2+-ATPase activator from the cultured dinoflagellateSymbiodinium sp.

Summary A novel sphingosine derivative, symbioramide, has been isolated from the laboratory-cultured dinoflagellateSymbiodinium sp. as a sarcoplasmic reticulum (SR) Ca²⁺-ATPase activator, and its structure elucidated to be1 on the basis of spectral and chemical means.Acknowledgments. We thank Ms M. Hamashima and Ms A. Muroyama for their technical assistance.     

Luffolide,a novel anti-inflammatory terpene from the spongeLuffariella sp.

Summary Luffolide (4) is a minor metabolite of the spongeLuffariella sp. from Palau. The structure of luffolide was determined by single crystal X-ray analysis. Luffolide is relatively unstable and undergoes a complex cyclization reaction to give the hexacyclic products5 and6. Luffolide (4) has some of the anti-inflammatory properties of manoalide (1): this may help to define the chemical reaction between manoalide (1) and phospholipase A₂.All crystallographic calculations were done on a PRIME 9950 computer operated by the Cornell Chemistry Computing Facility. Principal programs employed were: FOBS, a data reduction program by G.D. Van Duyne, Cornell University, 1987; MULTAN 80, and RANTAN 80, systems of computer programs for the automatic solution of crystal structures from X-ray diffraction data (locally modified to perform all Fourier calculations including Patterson syntheses) written by P. Main, S. E. Hull, L. Lessinger, G. Germain, J. P. Declercq and M. M. Woolfson, University of York, England, 1980 BDLS, an, anisotropic block diagonal least squares refinement written by K. Hirotsu, E. Arnold, and G. D. Van Duyne, Cornell University, 1987; PLUTO 78, a locally modified crystallographic illustration program by W. D. S. Motherwell, Cambridge Crystallographic Data Centre, 1978; and BOND, a program to calculate molecular parameters and prepare tables written by K. Hirotsu and G. Van Duyne, Cornell University, 1985.Acknowledgment. We thank the Government of the Republic of Palau for a scientific research permit. We thank Dr Klaus Rützler, Smithsonian Institution, Washington, D.C. for identifying the sponge and Mary Kay Harper for performing additional bioassays. This research was supported by grants from the Sea Grant College Programs of California [Projects R/MP-30 to DJF) and R/MP-31 (to RSJ)] and New York (to JC) and the National Institutes of Health (CA 24487 to JC).     

2,3-Dihydrolinderazulene,a new bioactive azulene pigment from the gorgonianAcalycigorgia sp.

Summary A new azulene pigment, 2,3-dihydrolinderazulene, has been isolated along with guaiazulene and linderazulene as bioactive metabolites from the gorgonianAcalycigorgia sp.     

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.     

Structure and stereochemistry of brianolide,a new antiinflammatory diterpenoid from the Okinawan gorgonianBriareum sp.

Summary Brianolide (1), a new antiinflammatory diterpenoid of the briarein class, possessing a substituent at C-12 (R), has been isolated from the Okinawan gorgonianBriareum sp. Its structure has been established from spectral data in conjunction with a single crystal X-ray analysis.     

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.     

A farnesyl arabinoside as an enhancer of glucose transport in rat adipocytes from a soft coral,Sinularia sp.

Separation of a lipophilic extract of a soft coral,Sinularia sp., assayed by enhancement of glucose transport in rat adipocytes, gave farnesyl 4-O--D-arabinopyranosyl--D-arabinopyranoside-2,2,3-triacetate (1a) whose structure was determined by spectroscopy. Enhancers of glucose transport may be useful for the prevention and treatment of diabetic disorders.