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).     

Molecular characterization and expression of the antimicrobial peptide defensin from the housefly (Musca domestica)

A 430-bp cDNA encoding the insect antimicrobial peptide defensin was cloned from the housefly, and designated Musca domestica defensin (Mdde). The open reading frame of the cDNA encoded a 92-amino acid peptide with an N-terminal signal sequence followed by a propeptide that is processed by cleavage to a 40-amino acid mature peptide. Northern analysis and in situ hybridization identified the corresponding mRNA in the fat body of bacterially challenged houseflies and in the epidermis of the body wall of naive and challenged houseflies. The Gram-negative bacterium (Escherichia coli) is a strong inducer of the gene. By RT-PCR, Mdde mRNA was also detected in naive and challenged insects. These findings suggest that the defensin gene is constitutively expressed in the epidermis of the housefly body wall. The predicted mature form of Mdde was expressed as a recombinant peptide in E. coli and Pichia pastoris. The recombinant Mdde expressed in Pichia was active against Gram-positive and some Gram-negative bacteria. Received 20 June 2006; received after revision 3 October 2006; accepted 30 October 2006     

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.     

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.     

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.     

Transfer of secondary metabolites from the spongesDysidea fragilis andPleraplysilla spinifera to the mantle dermal formations (MDFs) of the mudibranchHypserlodoris webbi

The opisthobranch molluscHypselodoris webbi is able to select, among its potential preys, sponges chemically rich in furanosesquiterpenoids. The sequestered secondary metabolites act as defensive allomones against predators and are accumulated in some dorsal glands (MDFs). This transfer from sponges to MDFs has been proven by maintainingH. webbi together with some selected sponges in an aquarium for a prolonged period.     

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.     

(E)-3-tridecen-2-one,an antibiotic from the interdigital glands of black-tailed deerOdocoileus hemionus columbianus

(E)-3-tridecen-2-one, the major volatile component of interdigital gland extracts from the black-tailed deer,Odocoileus hemionus columbianus, inhibited the growth of gram-positive bacteria and fungi. The bacteria,Propionibacterium acnes, and the fungi,Trichophyton mentagrophytes had a minimum inhibitory concentration (MIC) of 12.5 g/mL and 25 g/mL, respectively.     

Isolation and characterization of hemagglutinins from the spongeDysidea herbacea

Summary The spongeDysidea herbacea (Keller) was found to possess hemagglutinins. The major component, DHA-I, is a protein with a mol.wt of 26,000, which dissociates into subunits of equal size (14,000). It contains large amounts of glutamic acid and aspartic acid residues, but no half-cystine, methionine or histidine residues. DHA-I reacted with rabbit and human AB0 erythrocytes. D-galactose and lactose were effective inhibitors of DHA-I. The sponge also contained a minor component(s) which reacted preferentially with rabbit erythrocytes but not with human AB0 erythrocytes.Acknowledgment. We thank Dr. M. Yamazaki, Faculty of Pharmaceutical Sciences, Teikyo University, for testing mitogenic activity ofDysidea agglutinins. This study was partly supported by a grant-in-aid for Overseas Scientific Survey from the Ministry of Education, Science and Culture, Japan.     

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.     

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.     

New tamjamine class alkaloids from the marine ascidianAtapozoa sp. and its nudibranch predators. Origin of the tambjamines inAtapozoa

Summary Two new tambjamine class alkaloids, possessing ichthyodeterrent properties, have been isolated from the organic extracts of the marine ascidianAtapozoa sp. and its nudibranch predators. The structure of the new metabolites were elucidated through interpretation of their physical and spectral data and by comparison with spectral data for related compounds. Microscopic examination ofAtapozoa considering the yellow color of the tambjamines suggested thatAtapozoa is capable of the de novo biosynthesis of these metabolites.     

Relevance of chlorine-substituent for the antifungal activity of syringomycin and syringotoxin,metabolites of the phytopathogenic bacteriumPseudomonas syringae pv.syringae

Structural analogues of syringomycin and syringotoxin were produced by fermentation, characterized by FAB-MS and amino acid analysis and compared to the parent compounds in the antibiosis test againstRhodotorula pilimanae. The C-terminal residue was shown to be important for the activity.     

A blue light-reversible reaction in an animal system (Daphnia pulex)

Summary A photoreversible reaction, previously found only in plants and fungi, has now been found in an animal system. Activation of development in diapausing embryos ofDaphnia pulex, induced with white light, was suppressed with subsequent exposure to narrow-band (470 nm) or wide-band (410–525 nm) blue light. Pulses of wide-band blue light repeatedly reversed white light activation.     

A non-peroxide norsesterterpene from a marine spongeHyrtios erecta

Summary A new norsesterterpene, hyrtial4, and known sesterterpenes,1–3, have been isolated from an anti-inflammatory active crude extract of the spongeHyrtios erecta.This sponge,Hyrtios (Heteronema) erecta Keller 1889, collected in 1980/81, from Tonga was extremely abundant in the Vava'u Is. Group.We thank Prof. R. Jacobs and his research group at UCSB for this data.     

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.     

Secondary metabolites of the chemically rich ascoglossanCyerce nigricans

Summary Two new metabolites of an apparent propionate origin have been isolated from the organic extract of the ascoglossan molluscCyerce nigricans. The proposed structures for the new natural products are based on interpretation of their physical and spectral properties. The new compounds isolated lacked the potent ichthyodeterrent properties of the whole animal extract suggesting that other molecules are involved in the defense of this shell-less mollusc.     

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.