Chemistry of Puupehenone:  1,6-Conjugate Addition to Its Quinone−Methide System

Zjawiony, Jordan K.; Bartyzel, Piotr; Hamann, Mark T.

doi:10.1021/np9802062

Cited by 29 publications

(16 citation statements)

References 26 publications

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“…A compound whose structure differs from typical natural sesquiterpene quinones in that it has a quinone-methide system is puupehenone (14), and it was suggested that it interacts with DNA through addition to the quinone methide [87].…”

Section: Arylation Of Nucleophilesmentioning

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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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: Arylation Of Nucleophilesmentioning

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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“…Puupehenone and other related compounds exhibit very potent cytotoxic and antimicrobial activities, pointing to their possible role as defensive weapons in sponges. Apart from these detected activities that could be important in the chemical ecology of sponges, the exact role of puupehenones in sponges’ biology is not fully defined, although an interesting mechanism has been proposed for puupehenone by which this metabolite could participate in the detoxification of excess of hydrogen cyanide (HCN), probably produced by sponges as chemical weapon with defensive purpose [ 6 ]. It has been reported that harvested sponges from the order Verongida emitted HCN when they were broken apart, and this observation correlates with the necessity of a mechanism of detoxification of this toxic compound in the sponge [ 7 ].…”

Section: Origin and Biological Role Of Puupehenones In Spongesmentioning

confidence: 99%

“…It has been reported that harvested sponges from the order Verongida emitted HCN when they were broken apart, and this observation correlates with the necessity of a mechanism of detoxification of this toxic compound in the sponge [ 7 ]. The easy conversion of puupehenone into its cyano-derivatives (15α-cyanopuupehenol and its oxidation product 15α-cyanopuupehenone) by the addition of hydrogen cyanide under aqueous conditions suggests a possible hydrogen–cyanide–puupehenone cycle, highlighting the putative biological function of puupehenone in the sponge’s biochemical system [ 6 ].…”

Section: Origin and Biological Role Of Puupehenones In Spongesmentioning

confidence: 99%

“…Puupehenone, the most representative compound of this family, structurally differs from other sesquiterpene quinones because of the presence of a quinone–methide system responsible for its unique chemical behavior; it exhibits high chemical reactivity, facilitating the formation of many derived metabolites. The 1,6-Conjugated nucleophilic addition of HCN to puupehenone in the presence of water and alkaline conditions yields 15α-cyanopuupehenol and its oxidation product 15α-cyanopuupehenone [ 6 ]. Addition of oxygen nucleophiles such as acetoxy and methoxy ions to puupehenone (obtaining 15α-acetoxypuupehenol diacetate and 15α-methoxypuupehenol) has been also reported [ 4 , 10 ].…”

Section: Diversity and Chemical Synthesis Of Puupehenonesmentioning

confidence: 99%

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Pleiotropic Role of Puupehenones in Biomedical Research

2017

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Marine sponges represent a vast source of metabolites with very interesting potential biomedical applications. Puupehenones are sesquiterpene quinones isolated from sponges of the orders Verongida and Dictyoceratida. This family of chemical compounds is composed of a high number of metabolites, including puupehenone, the most characteristic compound of the family. Chemical synthesis of puupehenone has been reached by different routes, and the special chemical reactivity of this molecule has allowed the synthesis of many puupehenone-derived compounds. The biological activities of puupehenones are very diverse, including antiangiogenic, antitumoral, antioxidant, antimicrobial, immunomodulatory and antiatherosclerotic effects. Despite the very important roles described for puupehenones concerning different pathologies, the exact mechanism of action of these compounds and the putative therapeutic effects in vivo remain to be elucidated. This review offers an updated and global view about the biology of puupehenones and their therapeutic possibilities in human diseases such as cancer.

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“…58 Several nucleophilic agents have been used in a study of the 1,6-conjugate addition to the quinone-methide system of puupehenone. 59…”

Section: Bicyclofarnesanementioning

confidence: 99%