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.     

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.     

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.     

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.     

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.     

Studies on the fungal phytotoxin victorin: Structures of three novel amino acids from the acid hydrolyzate

Summary The host-selective phytotoxin victorin, produced by the fungusCochliobolus victoriae, was found to be at least partially peptidic in nature, and did not contain victoxinine. The exact mass of the M-H ion was measured by FABMS as 795.1877. Derivatives of three major acid hydrolysis products were isolated. The structures of the corresponding amino acids were assigned as 2S,3R-3-hydroxyleucine, 5,5-dichloroleucine, and 3-hydroxylysine. A into victorin by the fungus in vivo.     

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.     

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.     

Pheromone components of the female elephant hawk-moth,Deilephila elpenor,and the silver-striped hawk-moth,Hippotion celerio

By means of gas chromatographic and mass spectroscopic methods, and combined GC-electroantennogram and electrosensillogram techniques, (E)-11-hexadecenal and (10E, 12E)-10,12-hexadecadienal [(E,E)-bombykal is also the main constituent of the pheromone of the silver-striped hawk-mothHippotion celerio. The biological activity of the substances was demonstrated with electroantennogram and single cell recording, and the physiological efficacy of the different hexadecadienal isomers compared.Pheromones, 79; as Pheromones, 78 is taken: Wu, Cai-Hong, and Bestmann, H. J., Chinese Science Bulletin34 (1989) 1475; pheromones, 77: Attygalle, A. B., Steghaus0Kovac, S., Ahmed, V. U., Maschwitz, U., Vostrowsky, Ol, and Bestmann, H. J., Naturwissen-schaften78 (1991) 90.     

Invaders,weeds and the risk from genetically manipulated organisms

Invaders, weeds and colonizers comprise different but overlapping sets of species. The probability of successful invasion is low. The 10:10 rule state that 10% of introduced speices (those with feral individuals) become established, 10% of established species (those with self-sustaining populations) become pests. The rule gives an adequate fit to British plant data. The rule predicts that invaders will be rarer than natives. This is shown for British Anatidae. There is a continuous spectrum of perceived weediness. Although this spectrum is significantly related to Baker characters, neither those characters or any others can usefully predict which species will be weeds over a wide range of species. Characters tuned to sets of closely related species shown more promise. A study of BritishImpatiens shows that the characters responsible for critical ecological behaviour are still obscure. Small genetic changes can cause large ecological changes. GMOs will have characters entirely new to that species' evolutionary history. While most will have little ecological effect, a few may be ecologically and economically damaging. A sensible programme of field trials and monitoring is justified to minimize the risk.     

Aberrant,canavanyl protein formation and the ability to tolerate or utilize L-canavanine

Summary L-Canavanine, 2-amino-4-(guanidinooxy)butyric acid, and L-arginine incorporation into de novo synthesized proteins was compared in six organisms. Utilizing L-[guanidinooxy¹⁴C]canavanine and L-[guanidino¹⁴C]arginine at substrate saturation, the canavanine to arginine incorporation ratio was determined in de, novo synthesized proteins.Caryedes brasiliensis andSternechus tuberculatus, canavanine utilizing insects;Canavalia ensiformis, a canavanine storing plant; and to a lesser extentHeliothis virescens, a canavanine resistant insect, failed to accumulate significant canavanyl proteins. By contrast,Manduca sexta, a canavanine-sensitive insect, andGlycine max, a canavanine free plant, readily incorporated canavanine into newly synthesized proteins. This study supports the contention that the incorporation of canavanine into proteins in place of arginine contributes significantly to canavanine's antimetabolic properties.     

Biomedicine and diseases: the Klippel-Trenaunay syndrome, vascular anomalies and vascular morphogenesis

Vascular morphogenesis is a vital process for embryonic development, normal physiologic conditions (e.g. wound healing) and pathological processes (e.g. atherosclerosis, cancer). Genetic studies of vascular anomalies have led to identification of critical genes involved in vascular morphogenesis. A susceptibility gene, VG5Q (formally named AGGF1), was cloned for Klippel-Trenaunay syndrome (KTS). AGGF1 encodes a potent angiogenic factor, and KTS-associated mutations enhance angiogenic activity of AGGF1, defining ‘increased angiogenesis’ as one molecular mechanism for the pathogenesis of KTS. Similar studies have identified other genes involved in vascular anomalies as important genes for vascular morphogenesis, including TIE2, VEGFR-3, RASA1, KRIT1, MGC4607, PDCD10, glomulin, FOXC2, NEMO, SOX18, ENG, ACVRLK1, MADH4, NDP, TIMP3, Notch3, COL3A1 and PTEN. Future studies of vascular anomaly genes will provide insights into the molecular mechanisms for vascular morphogenesis, and may lead to the development of therapeutic strategies for treating these and other angiogenesis-related diseases, including coronary artery disease and cancer.Received 24 November 2004; received after revision 21 January 2005; accepted 2 March 2005     

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.     

Effects of the virulence plasmid ColV,I-K94 on the sensitivity ofEscherichia coli to putative environmental inhibitory agents

Summary Derivatives ofEscherichia coli carrying the virulence plasmid, ColV, I-K94 were more resistant than the ColV^– parents to phage Mel but were more sensitive to the hydrophobic inhibitors deoxycholate, erythromycin and lysozyme. The basis for these changes in sensitivity has been examined in ColV⁺ mutants with altered colicin or VmpA protein levels and in ColV⁺ strains with repressed transfer properties.The authors wish to thank the Fondacion Gran Marischal de Ayacucho and the Central Research Fund of the University of London for financial support.     

Pectinoacetals A-C: novel sterol hemiacetals from the gorgonianCtenocella pectinata

Three polyhydroxylated sterol hemiacetals, pectinoacetals A-C (1–3) have been isolated as their acetyl derivatives (4–6) from the acetic anhydride treated organic extract of the Indo-Pacific gorgonianCtenocella pectinata. These natural products were found to undergo very rapid epimerization at the C-18 chiral center and thus exist only as an equilibrium mixture of two diastereomers. The structure assignments are based on spectral studies and chemical modifications of the natural products.     

Structure assignments of two new C-18-oxygenated steroidal ketals isolated from a pacific soft coral of the genusSinularia

Summary Two new C-18-oxygenated sterols possessing a spiroketal function (1 and2) have been isolated from a soft coral of the genusSinularia. The proposed structures are based on spectral data.     

Vidalols A and B,new anti-inflammatory bromophenols from the Caribbean marine red algaVidalia obtusaloba

Chemical studies of the Caribbean red algaVidalia obtusaloba have resulted in the isolation of two new bromophenolic metabolites, vidalols A and B (1, 2). The new compounds were discovered as part of an organized effort to isolate new naturally-occurring anti-inflammatory agents with a focus upon those which may function through the inhibition of phospholipase A₂.     

Insect tissues,not microorganisms,produce linoleic acid in the house cricket and the American cockroach

Summary Biosynthesis of linoleic acid, 182(n–6), was unambiguously demonstrated to occur in the cockroach,Periplaneta americana, and the cricket,Acheta domesticus. Axenic tissue from both of these insect species was demonstrated by radio-gas-liquid chromatography (radio-GLC) and radio-high-performance liquid chromatography (radio-HPLC) to incorporate [1-¹⁴C]acetate and [1-¹⁴C]oleate into this essential fatty acid.This work was supported by the National Science Foundation under grant DCB-8914417. We would like to thank Coby Schal for his generous gift of American cockroaches and Tania Kellermeyer for her excellent technical assistance.     

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).     

Identification of a new predaceous stink bug pheromone and its attractiveness to the eastern yellowjacket

Summary Males ofPodisus fretus (Hemiptera: Pentatomidae) release a long-range attractant pheromone containing linalool (49.0%), (E)-2-hexenal (34.5%), benzyl alcohol (12.0%), nerolidol (2.0%),-terpineol (1.1%), and traces of several other compounds. The eastern yellowjacket,Vespula maculifrons (Hymenoptera: Vespidae), is attracted to artificial pheromones forP. fretus and for the sympatric species,Podisus maculiventris.The authors thank Mr T.J. Henry of the USDA Systematic Entomology Laboratory and Dr J.E. McPherson, Southern Illinois University, for examining the pentatomid species and Dr A.S. Menke, USDA-SEL, for determining the yellowjacket species. We also thank S. Wilzer for technical assistance. Mention of a company name does not imply endorsement by the US Department of Agriculture.