Ilimaquinone, a sesquiterpenoid quinone from a marine sponge

Luibrand, Richard T.; Erdman, Timothy R.; Vollmer, John J.; Scheuer, Paul J.; Finer, Janet; Clardy, Jon

doi:10.1016/0040-4020(79)87004-0

Cited by 142 publications

(111 citation statements)

References 7 publications

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“…However, in some other cases, the assignment of absolute stereochemistry of asymmetric carbon atoms was not simple and was shown to be unreliable if based on correlations of circular dichroism (CD) measurements of low magnitude. For instance, the configuration of the carbon atoms at positions C-5,8,9 and 10 in ilimaquinone (3) was initially assigned as enantiomeric to those in avarol (1) [7]. The error was later corrected [8] by chemical degradation and correlation of the CD measurement data of the obtained products with those of compounds with firmly established stereochemistry to show that sesquiterpenoids 1, 2 and 3 have the same absolute stereochemistry, i.e.…”

Section: Structurementioning

confidence: 99%

“…Since their great structural diversity, differences in origin, biosynthetic pathways and biological activities require further divisions, in this report primarily one subgroup is considered, namely the quinoid compounds formed by a mixed shikimate-mevalonate biogenesis, resulting in formation of a 4,9-friedodrimane rearranged bicyclic sesquiterpene skeleton attached to a (hydro)quinone moiety. A representative group of compounds: avarol (1) [6] and avarone (2) [6] from Dysidea avara, ilimaquinone (3) [7,8] from Petrosaspongia metachromia (previously named Hippospongia metachromia), isospongiaquinone (4) [9,10] from Stelospongia conulata, the nakijiquinones 5a-d [11] from Spongia sp., bolinaquinone (6) [12] from Dysidea sp., is presented in Figure 1 and their chemistry and biological effects analyzed in the sections that follow.…”

Section: Quinones With a Rearranged Drimane Skeleton From Sponges Of mentioning

confidence: 99%

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Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

Sladić

Gašić

2006

Molecules

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A review of results of bioactivity and reactivity examinations of marine sesquiterpene (hydro)quinones is presented. The article is focused mostly on friedorearranged drimane structural types, isolated from sponges of the order Dictyoceratida. Examples of structural correlations are outlined. Available results on the mechanism of redox processes and examinations of chemo-and regioselectivity in addition reactions are presented and, where possible, analyzed in relation to established bioactivities. Most of the bioactivity examinations are concerned with antitumor activities and the mechanism thereof, such as DNA damage, arylation of nucleophiles, tubulin assembly inhibition, protein kinase inhibition, inhibition of the arachidonic cascade, etc. Perspectives on marine drug development are discussed with respect to biotechnological methods and synthesis. Examples of the recognition of validated core structures and synthesis of structurally simplified compounds retaining modes of activity are analyzed.

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Section: Structurementioning

confidence: 99%

Section: Quinones With a Rearranged Drimane Skeleton From Sponges Of mentioning

confidence: 99%

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

Sladić

Gašić

2006

Molecules

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“…Stahl et al 70 described the first enantioselective total synthesis of the nakijiquinones and their biological evaluation. Besides ilimaquinone (54), 71 smnenospongines (55-57), 72 metachromins L, N, P (58-60) 73 and mamanuthaquinone (61) 74 display antimicrobial, antiviral and cytotoxic activities.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

170

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As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

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“…Discovery of the linear zoanthoxanthin (1) and the angular pseudozoanthoxan- ingenious biomimetic synthesis of the two ring sp. 3 The structure of this metabolite is entirely (1, 2, R,R' = H) on an coupling consistent with the suggested C,N3 biogenetic of suitably functiOnalized C5N3 building blocks of these pigments. In this paper we moieties.…”

Section: R'mentioning

confidence: 80%

“…Yet surprisingly, 8 9 aside from a number of novel carotenoids (1) and quinones (2,3), and the unconventional chlorin bonellin (4), so far only one group of pigments belonging to an entirely new structural type has been…”

mentioning

confidence: 99%