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.     

Two sulfur-containing ansamycin antibiotics fromStreptomyces albolongus

Summary Two sulfur-containing ansamycin antibiotics were isolated from the culture broth ofStreptomyces albolongus C-46366; the major one was identical with awamycin and the minor one was a new ansamycin antibiotic, ansathiazin. Their structures were elucidated from their reactions and spectroscopic analyses. These antibiotics were active against gram-positive bacteria, acid-fast bacteria and a protozoan.We thank Dr I. Umezawa for his generous gift of awamycin. We are grateful to Drs K. Morita, Y. Nakao, H. Okazaki and H. Ono for their interest throughout this work. Thanks are also due to Messrs Y. Kono, K. Koyama, H. Fujiuchi and Y. Nakano, and Mrs K. Jinno for their skillful technical assistance.     

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.     

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.     

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.     

Isolation and characterization of fukujusonorone,a 18-norpregnane derivative fromAdonis amurensis Regel et Radd

Zusammenfassung Aus den Wurzeln des japanischen Adonisröschens (Adonis amurensis Regel et Radd) wurde Fukujusonoron, ein neues Aglykon, das sich von 18-nor-Pregnan ableitet, isoliert.

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Abstracted from the Symposium Papers of the 12th Symposium on the Chemistry of Natural Products, Sendai 1968, p. 174. Y.Shimizu, Y.Sato and H.Mitsuhashi, Chem. pharm. Bull., Tokyo15, 2005 (1967); Chem. pharm. Bull., Tokyo, submitted for publication.     

Determination of diel periodicity of sex pheromone release in three species of Lepidoptera by ‘closed-loop-stripping’

Summary By means of closed-loop-stripping and subsequent GC analyses the diel periodicity of release of (Z)-11-hexadecenyl acetate, (E)-8-dodecenyl acetate, and (Z)-9-tetradecenyl acetate, the main constituents of the respective sex pheromone blends ofMamestra brassicae, Cryptophlebia leucotreta andSpodoptera sunia females, was determined.Pheromones, 64. For the 63rd contribution we have taken from: Szöcs, G., Toth, M., Bestmann, H. J., Vostrowsky, O., Heath, R. R., and Tumlinson, J. H., Z. Naturforsch.42c (1987) 165; Pheromones, 62: Bestmann et al.¹³.     

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.     

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.     

Mating attempts between the Scarlet Tiger Moth,Callimorpha dominula L., and the Cinnabar Moth,Tyria jacobaeae L. (Lepidoptera: Arctiidae), involve a common sex pheromone composition

It has been suggested that a common sex pheromone composition may account for interspecific sexual interactions observed with certain moths in the Arctiidae. In this study, it is demonstrated that the sex pheromones released by females of the Scarlet Tiger Moth,Callimorpha dominula L., and the Cinnabar Moth,Tyria jacobaeae L., have similar activities and elute at the same retention time on analysis by coupled gas chromatography (GC)-electrophysiology with males from each species. Peak enhancement on GC, chiral GC and coupled GC-mass spectrometry using authentic compounds show that the sex pheromone for bothC. dominula andT. jacobaeae is (3Z,6Z,9S,10R)-9,10-epoxyheneicosa-3,6-diene.     

(+)-Curcuphenol and dehydrocurcuphenol, novel sesquiterpenes which inhibit H,K-ATPase, from a marine sponge Epipolasis sp

Two H,K-ATPase inhibitors and an inactive related compound have been isolated from a marine sponge Epipolasis sp. They are aromatic sesquiterpene alpha-curcumenes.     

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.     

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.     

Neuropeptides of the silkworm,Bombyx mori

Six neuropeptides of the silkworm,Bombyx mori, have been isolated and chemically characterized during the past 10 years. They are bombyxin, prothoracicotropic hormone, pheromone-biosynthesis-activating neuropeptide/melanization-and-reddish-coloration hormone, diapause hormone, eclosion hormone, and adipokinetic hormone. Recent progress in research on these neuropeptides is described.     

Dominance for enzyme activity inDrosophila melanogaster

Summary A regulatory element tightly linked to theGpdh locus inDrosophila melanogaster has been isolated from a natural population. Flies homozygous for second chromosomes bearing the element,H31, have half the GPDH activity of normal homozygotes. Heterozygotes betweenH31 andF orS alleles exhibit dominance in GPDH activity. Heterozygotes betweenH31, F orS andDf(2L) GdhA have half the diploid level. The contribution of theS allele to the activity inS/H31 heterozygotes is more than four times that ofH31. The regulatory element distinguishingH31 is tightly linked to theGpdh ⁺ locus.     

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.     

Staurosporine aglycone (K252-c) and arcyriaflavin A from the marine ascidian,Eudistoma sp

Staurosporine aglycone (K252-c) (compound1) and arcyriaflavin A (2) were isolated from a specimen of the marine ascidian,Eudistoma sp., collected off the coast of West Africa. In addition to expressing micromolar and submicromolar inhibition of enzyme activity against seven protein kinase C isoenzymes and inhibition of proliferation of the human lung cancer A549 and P388 murine leukemia cell lines,1 also inhibited cell adhesion of the EL-4.IL-2 cell line and expressed activity in the K562 bleb and neutrophil assays.     

Inhibitory effect of halocyamine,an antimicrobial substance from ascidian hemocytes,on the growth of fish viruses and marine bacteria

Summary Halocyamine A, an antimicrobial substance isolated from hemocytes of the solitary ascidianHalocynthia roretzi, inhibited in vitro the growth of fish RNA viruses (infectious hematopoietic necrosis virus and infectious pancreatic necrosis virus). Pretreatment of RNA virus with halocyamine A reduced the infectivity of the virus toward host cells. The growth of marine bacteria,Achromobacter aquamarinus andPseudomonas perfectomarinus, was also inhibited by halocyamine A but that ofAlteromonas putrefaciens andVibrio anguillarum was not. These results suggest that halocyamine may have a role in the defense mechanisms ofH. roretzi against marine viruses and bacteria.     

The origin of the series elastic component in single crayfish muscle fibres

Summary High-speed cinematographic studies on the length changes of single tetanized crayfish muscle fibres during a step decrease in length revealed a fairly uniform distribution of a highly compliant series elastic component along the fibre length, suggesting that it mainly originates from some structures in each sarcomere other than the cross-bridges.We wish to thank Dr H. Hashizume of the Engineering Research Institute, Tokyo University for providing facilities to use the ultra high-speed cine-camera, and Mr T. Tsuno, Mr Y. Nakamura and Miss S. Gomi for their technical assistance.     

Communicating junctions between pillar cells in the gills of the atlantic hagfish,Myxine glutinosa

Summary In the respiratory lamellae of the gills of the atlantic hagfish,Myxine glutinosa, pillar cells are coupled by communicating junctions. It is suggested that these cells behave like a functional syncytium.Supported by the DFG, SFB 146. The authors are indebted to Drs F. Walvig and H. Stolte for kindly providing the hagfish. The expert technical assistance of G. Voss-Wermbter, Dipl.-Ing., and H. Heidrich is gratefully acknowledged.