Sesterterpenes from Spongia idia

Walker, Roger P.; Thompson, J.R.; Faulkner, D. John

doi:10.1021/jo01312a032

Cited by 111 publications

(124 citation statements)

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“…The cyclization of the Czs ether (1) produces a scalarane sesterterpenoid. These scalarane derivatives are found only among sponges of the Dictyoceratidae family [24,[29][30][31][32][33][34][35]. Since in most of the sponges up to one third of the volume is occupied by symbiotic microbes and various detritus filtered off by the invertebrate, the origin of their terpenoid is still highly obscure and the presence of polycyclic terpenoids might be the expression of symbiont metabolism.…”

Section: Discussionmentioning

confidence: 99%

Enzymatic cyclization of all‐trans pentaprenyl and hexaprenyl methyl ethers by a cell‐free system from the protozoon Tetrahymena pyriformis

Renoux¹,

Rohmer²

1986

European Journal of Biochemistry

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A cell-free system from the protozoon Tetrahymenapyriforrnis capable of cyclizing squalene into tetrahymanol cyclizes all-trans pentaprenyl methyl ether to a scalarane-type sesterterpene and all-trans hexaprenyl methyl ether to bicyclo-, tricyclo-, tetracyclo-and pentacyclohexaprenyl methyl ethers, each corresponding to a possible cationic intermediate. The structures of the cyclization products have been determined by spectroscopic methods and are compatible with a biogenetic scheme involving polyprenyl ether cyclization. This is the first direct proof of an enzymatic cyclization of higher isoprenic alcohol derivatives, and we assume it was performed by the squalene-to-hopane cyclase of the protozoon. The formation of a scalarane-type sesterterpene from CZ5 polyprenyl methyl ether suggests that these terpenoids, whose presence is restricted to a few sponges, might be in fact microbial metabolites. Tricyclopolyprenyl derivatives have been identified in the organic matter from numerous sediments and they were interpreted as being chemical fossils of still unidentified microorganisms. The cyclization of hexaprenyl methyl ether is the first attempt of identification of these tricyclopolyprenol derivatives in living organisms.Some of the numerous microbial lipids have been discovered after the identification of their chemical fossils dispersed in the organic matter of sediments [l]. The ubiquitous geohopanoids are the most striking example: they have been found to be present, varied and abundant, in all sediments analyzed up to now, and they were found to be the molecular fossils of a new class of widespread and varied prokaryotic lipids, the microbial hopanoids [2, 31. The existence of other new classes of microbial lipids has been postulated by us from the wide distribution of still 'orphan' chemical fossils, plausible precursors of which were unknown in extant microorganisms [l]. These included, for instance, aliphathic glycerol ethers similar to the archaebacterial lipid ethers, the pentacyclic triterpene isoarborinol and the tricyclopolyprenols. The existence of the latter compounds in microorganisms was suggested by the identification of tricyclic sedimentary hydrocarbons in the CI9 to C45 range' [4-71. Biogenetically, these isoprenoids can be deduced from a proton-catalyzed cyclization of suitable regular polyprenol derivatives giving tricyclic compounds, the structures of which resemble those of some natural sesterterpenes isolated from a fern or a nudibranch [8,9]. Such cyclizations have already been studied in the biosynthesis of lower homologues from the mono-, sesqui-and diterpene series.Correspondence to M. Rohmer, Ecole Nationale Superieure de Chimie de Mulhouse, 3 rue Alfred Werner, F-68093 Mulhouse Cedex, France A bbreviutions. TLC, thin-layer chromatography; GLC, gas-liquid chromatography; MS, mass spectrometry; NMR, nuclear magnetic resonance.In an attempt to detect these isoprenoids in living organisms, we tried to cyclize tritium-labelled all-trans pentaprenol and hexaprenol derivatives with cell...

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Section: Discussionmentioning

confidence: 99%

Enzymatic cyclization of all‐trans pentaprenyl and hexaprenyl methyl ethers by a cell‐free system from the protozoon Tetrahymena pyriformis

Renoux¹,

Rohmer²

1986

European Journal of Biochemistry

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“…145 The sponge Spongia idia (Leiosella idia) from Pt Loma, San Diego, contained idiadione 267. 186 Idiadione was found to be toxic to the sea star Pisaster giganteus, a brine shrimp Artemia sp., and the ectoproct Membranipora memoranacea, and also immobilized the larvae of the red abalone Haliotis rufescens in sea-water. Idiadione 267 was synthesized from citronellal, establishing the stereogenic centre as S. 187 The sesterterpenoid 268, obtained from the Caribbean sponge Thorecta horridus, 188 possessed a marked inflammatory activity, inducing the release of histamine and causing oedema in the paw of test animals.…”

Section: Furanoditerpenoidsmentioning

confidence: 99%

Heterocyclic Terpenes: Linear Furano‐ and Pyrroloterpenoids

Wang

et al. 2006

ChemInform

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“…Considera-se que as esponjas foram os primeiros animais marinhos estudados do ponto de vista químico [11][12][13][14][15][16] . Estudos com produtos naturais de esponjas marinhas forneceram importantes informações do ponto de vista quimiotaxonômico [17][18][19][20] , ecológi-co [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] , e sobre sua química e bioquímica 1,[38][39][40][41][42][43] . Porém, tendose em vista que diversas espécies de esponjas apresentam associações com cianobactérias e bactérias [44][45][46][47] , considera-se que vários produtos naturais isolados de esponjas possam ser originários de microorganismos 48 .…”

Section: Introductionunclassified

unclassified

Alcalóides alquilpiridínicos de esponjas marinhas

Almeida¹,

Berlinck²,

Hajdu³

1997

Quím. Nova

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Recebido em 8/3/96; aceito em 29/8/96 ALKYLPYRIDINE ALKALOIDS FROM MARINE SPONGES. The chemistry of alkylpyridine alkaloids originating from marine sponges is comprehensively reviewed, with emphasis on their natural occurrence, methods for their isolation, spectroscopic characterization, biological activities e chemical synthesis. A likely chemotaxonomic role is suggested, as markers for sponges of the Order Haplosclerida (Demospongiae).Keywords: marine sponges; alkylpyridine alkaloids. REVISÃO INTRODUÇÃOEsponjas (Phylum Porifera) são animais aquáticos, marinhos ou de água doce, sésseis na fase adulta, de cores, formas e dimensões variadas. São metazoários primitivos (considera-se que as esponjas surgiram há entre 600.000.000 e 450.000.000 anos, no período Cambriano), provavelmente os primeiros animais pluricelulares a surgirem ao longo da evolução. As esponjas não possuem órgãos ou sistemas diferenciados, suas células não constituem tecidos strictu sensu, e as ligações intercelulares são lábeis e instáveis. Devido a seu caráter primitivo, as esponjas são um dos elementos dominantes em diversos ecossistemas marinhos passados e presentes, dentre estes os arrecifes coralinos e os ambientes antárticos 1-3 . Mais de 5000 espécies de esponjas já foram descritas até o momento presente. O filo Porifera é cosmopolita, podendo ser encontrado da faixa entremarés ao assoalho dos oceanos, inclusive em fossas abissais (abaixo de 8000 metros). A classificação atual dos espongiários divide o filo Porifera em dois subfilos: Symplasma com uma única Classe, Hexactinellida (esponjas com esqueleto formado por espículas com seis pontas, ou hexáctinas, compostas de silício), também conhecidas como esponjas-de-vidro; e Cellularia, com duas Classes, Calcarea (esponjas com esqueleto formado por espículas de carbonato de cálcio), e Demospongiae (esponjas com esqueleto de espículas de silício ou de espongina, ou ainda de uma combinação de ambas), esta compreendendo 90% do número total de espécies 4-9 . Apesar de estudados há mais de um século e meio, ainda há questões fundamentais a responder acerca dos Porifera devido, em grande parte, à controvérsias quanto à sua taxonomia, o acesso à muitas espécies só ter sido possível após o advento do mergulho autônomo a partir da II Guerra Mundial, bem como à dificuldade de sua manutenção em aquários devido a sua morte precoce ou significativas alterações no seu padrão metabólico. Dentre os invertebrados, os espongiários são os menos estudados do ponto de vista biológico 10 . Considera-se que as esponjas foram os primeiros animais marinhos estudados do ponto de vista químico [11][12][13][14][15][16] . Estudos com produtos naturais de esponjas marinhas forneceram importantes informações do ponto de vista quimiotaxonômico [17][18][19][20] , ecológi-co [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] . Sem perder tempo, ele as corta vigorosamente com uma pequena foice. Tão logo arranca a esponja da rocha, ele puxa a corda à qual está atado chamando seus companheiros pa...

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Sesterterpenes from Spongia idia

Cited by 111 publications

References 0 publications

Enzymatic cyclization of all‐trans pentaprenyl and hexaprenyl methyl ethers by a cell‐free system from the protozoon Tetrahymena pyriformis

Enzymatic cyclization of all‐trans pentaprenyl and hexaprenyl methyl ethers by a cell‐free system from the protozoon Tetrahymena pyriformis

Heterocyclic Terpenes: Linear Furano‐ and Pyrroloterpenoids

Alcalóides alquilpiridínicos de esponjas marinhas

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