Recent research in marine natural products: the puupehenones

Ravi, Bhavya; Perzanowski, Herman P.; Ross, Ronald; Erdman, Timothy R.; Scheuer, Paul J.; Finer, Janet; Clardy, Jon

doi:10.1351/pac197951091893

Cited by 90 publications

(100 citation statements)

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“…puupehenone (14) from the sponge Hyrtios sp. [46,47], which also shows a potent antituberculosis activity [48]). Among those are also the ones with a 4,9-friedo-rearranged skeleton, such as ilimaquinone (3) [49], and a related amino derivative 15 from the sponge Dactylospongia elegans [50], the nakijiquinones 5 [11] and especially avarone (2) and avarol (1), with strong ED 50 activities of 0.62 µM and 0.93 µM, respectively, for mouse lymphoma cells [51,52].…”

Section: Biological Effects I) Antitumor Activitymentioning

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: Biological Effects I) Antitumor Activitymentioning

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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“…The sesquiterpene quinones such as puupehenone 32 and the hundreds of natural or synthetic analogues [55] including 15-cyanopuupehenone 33 [56], proved to be a fertile source for the development of antituberculosis drugs. Puupehenone 32 was initially isolated in 1979 by Scheuer's group from the Hawaiian Chondrosia chucalla sponge [57] but its absolute configuration, and consequently that of its many co-metabolites, was only determined in 1996 by Capon's group [58]. These compounds displayed a wide range of biological activities such as antifungal, antimicrobial, antimalarial, antiviral, cytotoxic, and immunodulatory activity but have not, until now, progressed to more thorough development.…”

Section: Antituberculosis Agents Of Marine Originmentioning

confidence: 99%

Marine Pharmacology: Potentialities in the Treatment of Infectious Diseases, Osteoporosis and Alzheimer's Disease

Bourguet‐Kondracki

Kornprobst²

2005

Marine Biotechnology II

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“…A composition of C42H5406 was ascertained by mass spectrometry. The fragmentation pattern, including abundant M + -15 (m/z 639) and M + -151 (see wiggly line in 4) ions, were reminiscent of the puupehenone spectrum [2]. The presence of OH-groups was indicated by IR bands at 3560 and 3420 cm-I.…”

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confidence: 93%

“…Occasionally, compounds of mixed biosynthesis have been encountered, among them the puupehenones 1-3, which are constructed of sesquiterpene and benzene moieties [2]. The yellow encrusting sponge, identified as Heteronenza sp.…”

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confidence: 99%

A Dimer of Puupehenone

Amade

Chevelot

Perzanowski³

et al. 1983

Helvetica Chimica Acta

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SummaryThe structure of a colorless dimer (4a) of puupehenone (l), which was isolated from Pacific marine sponges, has been elucidated from spectral data.Marine sponges are a rich source of secondary metabolites, particularly terpenoids [ 11. Occasionally, compounds of mixed biosynthesis have been encountered, among them the puupehenones 1-3, which are constructed of sesquiterpene and benzene moieties [2]. The yellow encrusting sponge, identified as Heteronenza sp. (family Spongiidue, order Dictyoceratidu, class Demospongiae), from which puupehenone (1) was originally isolated, was first collected by us off the Hawaiian islands of Lanai and Oahu. The halopuupehenones 2 and 3 were minor constituents in a Heteronemu sample from Enewetak in the Marshall islands. In all collections we encountered several dimeric compounds, some of them highly colored. A colorless dimer, bispuupehenone (4a). was subsequently also isolated from a Tahitian sponge, Hjrtios (= Inodes) eubumma (family Thorectidae, order Dictyoceratida), and is the subject of this report.H. eubumma was preserved in EtOH and then further extracted with the same solvent. The aqueous residue was partitioned with cyclohexane. Chromatography of the organic residue on Sephadex, then silica gel, yielded puupehenone (1) and bispuupehenone (4a), m.p. 234-240". A composition of C42H5406 was ascertained by mass spectrometry. The fragmentation pattern, including abundant M + -15 (m/z 639) and M + -151 (see wiggly line in 4) ions, were reminiscent of the puupehenone spectrum [2]. The presence of OH-groups was indicated by IR bands at 3560 and 3420 cm-I.The I3C-NMR spectrum displayed 2 1 signals, thus confirming that bispuupehenone (4a),is a symmetrical dimer of 1. Fifteen upfield signals parallel those of other drimane derivatives, e.g. 1, its methanol adduct 5, or 8-epichromazonarol (6) [3] I )

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Recent research in marine natural products: the puupehenones

Cited by 90 publications

References 0 publications

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

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

Marine Pharmacology: Potentialities in the Treatment of Infectious Diseases, Osteoporosis and Alzheimer's Disease

A Dimer of Puupehenone

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