Floresolides, new metacyclophane hydroquinone lactones from an ascidian, Aplidium sp

Issa, Hassan; Tanaka, Junichi; Rachmat, Rachmaniar; Higa, Tatsuo

doi:10.1016/s0040-4039(02)02812-5

Cited by 29 publications

(27 citation statements)

References 5 publications

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“…collected in Indonesian. All of these floresolides exhibited moderate cytotoxicity against KB tumor cells [49]. The synthesis of floresolide B ( 40 ) hydroquinone lactone core was performed by employing ring-closing metathesis approach by Briggs and Dudley [50].…”

Section: Introductionmentioning

confidence: 99%

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

et al. 2014

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Ascidians of the genus Aplidium are recognized as an important source of chemical diversity and bioactive natural products. Among the compounds produced by this genus are non-nitrogenous metabolites, mainly prenylated quinones and hydroquinones. This review discusses the isolation, structural elucidation, and biological activities of quinones, hydroquinones, rossinones, longithorones, longithorols, floresolides, scabellones, conicaquinones, aplidinones, thiaplidiaquinones, and conithiaquinones. A compilation of the 13C-NMR spectral data of these compounds is also presented.

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Section: Introductionmentioning

confidence: 99%

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

et al. 2014

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“…These natural products are structurally characterized by the presence of a paracyclophane and/or metacyclophane system built in a farnesyl quinone or hydroquinone. Longithorones B-D (24)(25)(26) which are closely related to the proposed monomer precursors of longithorone A, were isolated as minor components of A. longithorax together with the dimeric longithorones E-I (27)(28)(29)(30)(31). Longithorone A (23) is a dimeric prenylated quinone whose highly strained structure was determined by X-ray analysis [20].…”

Section: Non-nitrogenous Metabolitesmentioning

confidence: 99%

“…In 1994 Schmitz and co-workers isolated the first member of the longithorone series, longithorone A (23), from A. longithorax collected in Palau. On the other hand, the dimers longithorones E (27) and F (28) are atropoisomers about the para disubstituted benzoquinone ring. The authors proposed that 23 might biosynthetically derive by Diels-Alder cyclization of two appropriate cyclofarnesyl benzoquinones.…”

Section: Non-nitrogenous Metabolitesmentioning

confidence: 99%

Natural Products Chemistry in Marine Ascidians of the Genus Aplidium

Zubı́a¹,

Ortega²,

Salvá

2005

MROC

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Ascidians (tunicates) are widely recognized as one of the most prolific producers of bioactive natural products in the marine environment. In particular, ascidians of the genus Aplidium are renowned for the variability in the metabolites that they content. The non-nitrogenous compounds are dominated by the presence of meroterpenoids exemplified by the longithorones. Among the nitrogen containing group, nucleosides, cyclic peptides and a high variety of alkaloids can be mentioned. In this review the most interesting aspects of structure elucidation and bioactivity of the natural products from species of the genus Aplidium reported up to the end of 2004 will be presented.

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“…The structures were determined by spectroscopic and X-ray analysis [13]. These compounds are related to the class of compounds known as longithorones and longithorols, but their unique features are in the presence of an ε-lactone bridging the aromatic ring and a [10]metacyclophane band and of a double bond or an epoxy function at the bridgehead, confining the cyclophane ring into a relatively rigid system.…”

Section: Metabolites From An Ascidianmentioning

confidence: 99%

Diverse metabolites of coral reef organisms

Tanaka

Kuniyoshi

Tanaka

et al. 2005

Pure and Applied Chemistry

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A detailed mechanism for the spontaneous transformation of 2-chloro-1-hydroxyoctoda-3(8),5-dien-4-one, a metabolite of Portieria hornemanni, into 4,5-dimethylbenzo[b]-furan was presented. Five new terpenoids have been isolated from the red alga Laurencia luzonensis. Five species of sponges yielded various metabolites: furanosesterterpenes from Ircinia sp., scalarane derivatives from Phyllospongia sp., polyketides from Theonella cf. swinhoei, a polyacetylene from Callyspongia sp., and cyclic depsipeptides from Suberites japonicus. Other new metabolites were sponge-derived secomanoalide derivative and imidazole alkaloids from nudibranchs, briarane class diterpenes from octocorals, and cyclofarnesylated hydroquinones, floresolides A-C, from an ascidian, Aplidium sp. Many of these compounds showed cytotoxicity.

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Floresolides, new metacyclophane hydroquinone lactones from an ascidian, Aplidium sp

Cited by 29 publications

References 5 publications

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

Quinone and Hydroquinone Metabolites from the Ascidians of the Genus Aplidium

Natural Products Chemistry in Marine Ascidians of the Genus Aplidium

Diverse metabolites of coral reef organisms

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