A novel hexachloro-metabolite from the sponge dysidea herbacea

Kazlauskas, Rymantas; Lidgard, RO; Wells, Robert J.; Vetter, Walter

doi:10.1016/s0040-4039(01)83192-0

Cited by 85 publications

(53 citation statements)

References 2 publications

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“…The sponge genus Dysidea has been the source of diverse organic metabolites, which have included bromophenols [6] and thiazole derivatives [7] in addition to numerous sesquiterpenoids [8]. Although the nakafuran skeletons have not previously been encountered, they can be readily related by established biogenetic transformations (Scheme 3) to known sesquiterpenes from Dysidea and from other sponges.…”

Section: 'mentioning

confidence: 99%

Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties

Schulte

Scheuer

McConnell

1980

Helvetica Chimica Acta

118

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SummaryTwo new sesquiterpenoids, nakafuran-8 (1) and -9 (8), have been isolated from the marine sponge Dysidea fragilis and from its prey, the nudibranchs Hypselodoris godeffroyana and Chromodoris maridadilus. The structures were established by spectral analysis and chemical transformations. Both compounds possess antifeedant properties when assayed in the laboratory against common reef fishes, Chaetodon spp.

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Section: 'mentioning

confidence: 99%

Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties

Schulte

Scheuer

McConnell

1980

Helvetica Chimica Acta

118

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“…The isolated polybrominated compounds were also active in the brine shrimp lethality test. In the latter bioassay, compounds 1 and 6 were the most active with LC 50 The marine sponge Dysidea herbacea Keller (family Dysideidae, Order Dendroceratida) occurs in two chemotypes; 1 one chemotype contains both polychlorinated amino acid derivatives 2,3 and sesquiterpenes, 4,5 while the second chemotype contains only polybrominated diphenyl ethers. 6,7 Thus, it has been previously argued that this chemical variation in D. herbacea is due to different algal or bacterial symbionts associated with the sponge.…”

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confidence: 99%

Four New Bioactive Polybrominated Diphenyl Ethers of the SpongeDysidea herbaceafrom West Sumatra, Indonesia

Handayani¹,

Edrada²,

Proksch³

et al. 1997

J. Nat. Prod.

126

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“…HFLWTICA CHIMICA ACTA Vol 67 (19x4) [2], das (-)-Dysidenin ((-)-3) [3] und das (+)-Isodysidenin ((+)-4) [4]. An einem Derivat des (+)-Isodysidenins ((+)-4) wurde von Kurlson et al [4] eine Rontgenstrukturanalyse durchgefuhrt und die absolute Konfiguration ebenfalls n i t Hilfe der anomalen Rontgenstreuung abgeleitet.…”

Section: R4unclassified

Synthese des Dysidins

Köhler

Gerlach

1984

Helvetica Chimica Acta

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The synthesis of dysidin ((-)-l), the enantiomer of a metabolite of the marine sponge Dysidea herbacea, is described. To effect the synthesis, (&)-5-isopropyl-4-methoxy-3-pyrrolin-Zone (7) is converted to its lithium salt and reacted with (-)-(5R,2E)-3-methoxy-5-trichloromethyl-2-hexenoyl chloride ((-)-11) to give (-)-1 and its diastereoisomer (+)-5-epidysidin ((+)-12) epimeric at C(5) of the pyrrolinone ring. The (-)acyl chloride (-)-11 has been synthesized from (+)-(R)-3-(trichloromethyl)butanoic acid ((+)-8) via the intermediates (+)-9 and (-)-lo, the pyrrolinone 7 from N-benzyloxycarbonyl-L-valine via the intermediate 5. The enantiomers of acid 8 have been resolved by fractional crystallization of their diastereoisomeric N-( 1 -phenylethyl)amides. The (R)-chirality of (+)-8 was determined by comparing the 'H-NMR spectra of the diastereoisomeric N-( 1 -phenylethyl)amides 16 and 17, made from (+)-8 by substituting deuterium for chlorine, with the spectra of the N-(1-phenylethy1)amides 14 and 15 of known absolute configuration. This correlation shows that literature value ( R ) for (-)-8 is in error. Therefore, the structural formulae of (-)-dysidenin and (+)-isodysidenin, two other metabolites of D. herbacea. have to be changed to their mirror images as shown in formulae (-)-3 and (+)-4, respectively. Einleitung. -Bei der Untersuchung der antimikrobiell wirksamen Inhaltsstoffe des krustenbildenden Meeresschwammes Dysidea herbacea wurde das (+)-Dysidin ((+)-1) isoliert und seine Struktur von Hoj7teinz & Oberhansli [I] durch Abbaureaktionen und niittels einer Rontgenstrukturanalyse bestimmt. Die auf dem australischen Great Barrier Reef gesammelten Exemplare des Meeresschwammes enthielten ca. 1 % des Naturstoffs (+)-1 in der Trockenmasse. Das Tetramsaurederivat Dysidin (1) besitzt eine neuartige Struktur mit CC1,-Gruppe, eine Gruppierung, welche vorher bei Naturstoffen nicht aufgefunden wurde. Bei der Rontgenstrukturanalyse des (+)-Dysidins wurde eine Reihe von Rontgen-Reflexen (Friedel-Paare) unter Verwendung von Cu-Ka Strahlung nochmals vermessen. Aus dem anomalen Streuverhalten der C1-Atome konnte die absolute Konfiguration des Naturstoffs bestimmt werden. Beide asymmetrischen C-Atome des (+)-Dysidins besitzen demnach (S)-Chiralitat (vgl. Formel (+)-1).Spater isolierten andere Arbeitsgruppen aus der Spezies Dysidea herbacea drei weitere Verbindungen mit CC1,-Gruppen, namlich das (-)-Dehydrodiketopiperazin (-)-2

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A novel hexachloro-metabolite from the sponge dysidea herbacea

Cited by 85 publications

References 2 publications

Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties

Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties

Four New Bioactive Polybrominated Diphenyl Ethers of the SpongeDysidea herbaceafrom West Sumatra, Indonesia

Synthese des Dysidins

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