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).     

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

Luffolide (4) is a minor metabolite of the sponge Luffariella 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 products 5 and 6. 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.     

The role of glycine in the biosynthesis of a terpene

Zusammenfassung Mit doppelt markiertem Glycin konnte gezeigt werden, dass das Kohlenstoffatom der Methylgruppe viel besser als das Kohlenstoffatom der Karboxylgruppe in die Isoprengruppe des Ophiobolins B ausCochiobolus miyabeanus eingebaut wird. Die Radioaktivität wird in Ophiobolin B eingebaut, wenn die folgenden Verbindungen verwendet werden: [3-¹⁴C]-Serin, [¹⁴C-Methyl]-Sarcosin, [¹⁴C-Methyl]-Methionin, und [¹⁴C] Formate.

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a)Studies on Biosynthesis. Part V. for Part IV, seeM. Anchel, A. K. Bose, K. S. Khanchandani andP. T. Funke, Phytochem.9, 2135 (1970). b) Presented in part at the 3rd Natural Products Symposium, University of West Indies, Jamaica, January 1970.

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The support of this research by Stevens Institute of Technology is gratefully acknowledged. We wish to thank Dr.J. H. Davis and Prof.L. Z. Pollara for their interest and encouragement and Drs.H. Levy, P. T. Funke, M. S. Manhas, P. K. Bhattacharyya andM. Anchel for valuable discussions and help with some of the experiments. We are particularly thankful to Dr.L. Canonica for providing us with cultures ofCochiobolus miyabeanus that made our work on ophiobolin B possible.     

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.     

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.     

13C NMR-study of flexibilide,an anti-inflammatory agent from a soft cora

Summary The use of¹³C spin-lattice relaxation measurements as a probe of structure in solution is illustrated for flexibilide. Analysis of quaternary carbon relaxation behaviour indicates that the structure in solution differs from the crystal structure. The effects of lanthanide shift and relaxation reagents on¹³C spectral parameters are also reported.Acknowledgment. We thank R.J. Wells, RRIMP, for helpful discussions.     

Structure of podecdysone C,a steroid with moulting hormone activity from the bark ofPodocarpus elatus R. Br.

Résumé Le Podecdysone C, un stérol extrait de l'écorce de l'arbrePodocarpus elatus R. Br. et qui fonctionne comme hormone de mue est identique au THE-III (26-hydroxy--ecdysone, II) extrait du ver du tabacManduca sexta.     

The isolation,culture and organ differentiation from mesophyll protoplasts ofMollugo nudicaulis Lam., a C4 species

Summary Isolation and culture of mesophyll protoplasts fromMollugo nudicaulis, a C₄ species, is reported. Protoplasts developed into callus with root formation. However, no shoot was differentiated. This work was carried out as a part of our overall objective of inducing somatic fusion between the protoplasts of C₃ and C₄ species ofMollugo.     

Isolation of a new C14 hydrocarbon from north Indian vetiver oil

Zusammenfassung Isolierung und Strukturaufklärung eines ungewöhnlichen Terpen-Kohlenwasserstoffs aus nordindischem Vetiver-öl.     

Desacetylscalaradial,a cytotoxic metabolite from the spongeCacospongia scalaris

Summary From the marine spongeCacospongia scalaris, scalaradial1, desacetylscalaradial2, and heteronemin3 were isolated. Compound2 showed potent cell growth inhibition. The stereochemistry of3 is briefly discussed.Acknowledgments. The authors are grateful to Prof. T. Hase and Mr R. Nakai for collecting the sponge and to Dr s. Tanida for the sponge identification.     

The precipitation of cytochrome C with a lipidic fraction from tissues and yeast

Riassunto Nel corso di ricerche sopra l'azione esplicata da alcune frazioni lipidiche sulla succinossidasi presente nei mitocondri di fegato di ratto, l'autore ha osservato che il citocromo C aggiunto al sistema precipita in presenza della frazione contenente lecitine cefaline e fosfatidi, estratta dal lievito o dal fegato di animali diversi.Di questo materiale è stata compiuta l'analisi elettroforetica su carta che non ha rivelato proteine migranti. L'analisi cromatografica su carta non ha mostrato aminoacidi liberi, ma dopo idrolisi 6–10 aminoacidi sono evidenziabili. Il precipitato risultante dalla unione della frazione lecitinica con il citocromo C è stato analizzato per il suo contenuto in P ed in N comparativamente ai materiali di origine. Detto precipitato è solubile solo in etere e la curva spettrofotometrica del citocromo C in queste condizioni appare modificata rispetto alla norma.La frazione lecitine non precipita in presenza di albumina di uovo e di emoglobina umana, mentre dà un forte precipitato in presenza di solfato di Fe e di citrato ferrico ammoniacale.L'attività biologica del citocromo C si annulla completamente con la precipitazione.     

Pleraplysillin-2, a further furanosesquiterpenoid from the spongePleraplysilla spinifera

Cellular and Molecular Life Sciences - Si riporta l'isolamento dalla spugnaPleraplysilla spinifera di un ulteriore furanosesquiterpenoide pleraplysillina-2 per il quale si dimostra la struttura 3.