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.     

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.     

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 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.     

Polypeptides and Leuches' anhydrides from carbamic acid derivatives of C-activated amino acids

Zusammenfassung Durch katalytische Hydrierung von C-aktivierten Carbobenzoxyaminosäurederivaten, z. B. von gemischten Anhydriden und aktivierten Estern, werden via die Carbaminsäurederivate die entsprechenden Leuchsschen Anhydride und Polypeptide erhalten.

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This work was supported by grants from the National Institutes of Health, U.S. Public Health Service (G.M. 06579 and G.M. 08795).     

Palinurin,a new linear sesterterpene from a marine sponge

Summary The structure of a new linear sesterterpene, palinurin (1), obtained from the marine spongeIrcinia variabilis, was determined by spectral and chemical means.This work was carried out at the Progetto Finalizzato Oceanografia e Fondi Marini, C.N.R., Roma. We thank Professor M. Sarà (University of Genova) for the identification of the sponge, Mr C. Di Pinto for¹H-and¹³C-NMR, Mr G. Scognamiglio for technical assistance.     

Furan fatty acid steryl esters from the marine spongeDictyonella incisa which show inflammatory activity

Summary Three new furan fatty acids, (9Z, 19Z)-3, 6-epoxyhexacosa-3,5,19-tetraenoic acid (1a), (8Z, 11Z, 14Z, 17Z)-3, 6-epoxyeicosa-3,5,8,11,14,17-hexaenoic acid (2a), and (8Z, 11Z, 14Z, 17E)-3, 6-epoxyeicosa-3,5,8,11,14,17-hexaenoic acid (3a), and a new polyunsaturated fatty acid (5Z, 8Z, 11Z, 14Z, 17E)-eicosa-5,8,11,14,17-pentaenoic acid (6a), present in the spongeDictyonella incisa as the respective steryl esters, have been isolated as methyl esters and their structures have been determined by spectral and chemical analysis. The furan fatty acid esters have shown a high inflammatory activity, which suggests their potential role as feeding deterrents.     

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.     

Furospongolide,a new C21 furanoterpene from a marine organism

Summary The structure of a new linear C₂₁ furanoterpene, furospongolide (1), obtained from the marine spongeDysidea herbacea, was determined by spectral means.We thank Professor J. Vacelet for the identification and Dr Loya and Mr Benayahu for the collection of the sponge.     

The amino acid sequence of the agglutinin isolated from the red marine alga Bryothamnion triquetrum defines a novel lectin structure

The primary structure of a lectin isolated from the red alga Bryothamnion triquetrum was established by combination of Edman degradation of sets of overlapping peptides and mass spectrometry. It contains 91 amino acids and two disulphide bonds. The primary structure of the B. triquetrum lectin does not show amino acid sequence similarity with known plant and animal lectin structures. Hence, this protein may be the paradigm of a novel lectin family.     

Scalarolbutenolide,a new sesterterpenoid from the marine spongeSpongia nitens

Summary A new sesterterpenoid, scalarolbutenolide (5), has been isolated from the marine spongeSpongia nitens; its structure, including the absolute stereochemistry, has been established by chemical and spectroscopic studies.This work is a part of the Progetto Finalizzato per l'Oceanografia e i Fondi Marini, C.N.R., Roma.We are indebted to A. Crispino, C. Di Pinto, G. Scognamiglio and R. Turco for their technical assistance.     

Isolation and amino acid compositions of geographutoxin I and II from the marine snail Conus geographus

The peptide toxins having inhibitory effects on the contractile response of the mouse diaphragm to direct stimulation, geographutoxin I and II, have been isolated from Conus geographus, and their amino acid compositions have been determined.     

Losses of nucleic acid derivatives from fixed tissues during flattening of paraffin sections on water

Zusammenfassung Aus fixiertem Gewebe bzw. Paraffinschnitten, die mit normaler Technik auf Wasser ausgebreitet werden, gelingt es, Nukleotide und Eiweissderivate zu extrahieren. Quantitative Daten werden mitgeteilt, und es wird deren Bedeutung für die Histochemie diskutiert.

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Aided by a grant from The Royal Physiographic Society, Lund.     

Diabetogenic action of alloxan-like derivatives of uric acid

Summary Two new potent diabetogenic substances 4,5-dihydro-4,5-dihydroxyuric acid (1) and 5-hydroxy-pseudouric acid (2) have been found.     

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.     

Further perhydroazulene diterpenes from marine organisms

Summary 3 novel diterpenes,4–6, having the perhydroazulene skeleton already found in pachydictiol A (1) and dictyol A (2) and B (3), have been isolated from both the digestive gland of Aplysia depilans and algae of the family Dictyotaceae.