Isolation and structure elucidation of azoricasterol, a new sterol of the deepwater sponge Macandrewia azorica

Gross, Harald; Reitner, J.; König, Gabriele M.

doi:10.1007/s00114-004-0552-6

Cited by 9 publications

(7 citation statements)

References 29 publications

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“…Marine organisms, above all sponges, contain unusual sterols (Djerassi, 1981;D'Auria et al, 1993;Fujita et al, 2001;Rudi et al, 2001;Volkman, 2003;Gross et al, 2004b), one of which is contignasterol (12) from Petrosia contignata. This highly oxygenated steroid is remarkable due to the unusual 14b proton configuration and the half acetal functionality in the side chain (Burgoyne et al, 1992;Yang and Andersen, 2002).…”

Section: Terpenoid Drugs Leadsmentioning

confidence: 99%

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

2006

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Marine organisms produce a wide array of fascinating terpenoid structures distinguished by characteristic structural features. Certain structural classes, e.g. cembrane, chamigrene, amphilectane skeletons, and unusual functional groups such as isonitrile, isothiocyanate, isocyanate, dichloroimine and halogenated functionalities occur predominantly in marine metabolites. Especially striking is the frequent occurrence of sesterterpenes in marine organisms, and sponges must be considered as one of the prime sources of these C 25 terpenoid compounds. In most cases however, these structural features are not strictly unique for marine natural products. The prominent biological activity of marine terpenes is evident in their ecological role in the marine environment, and makes them interesting as potential drugs. Several terpenoid compounds, e.g. eleutherobin, sarcodictyin, contignasterol derivatives, are in preclinical or clinical development. Despite the many structures known and their ecological and pharmacological importance, only a few biosynthetic studies on marine terpenoid compounds have been performed.

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Section: Terpenoid Drugs Leadsmentioning

confidence: 99%

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

2006

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“…To our knowledge the S-methylated form of ergothioneine was known only as a synthetic compound and not a natural product until it has once been reported in deepwater sponge extract in 2004. 41 For these authors as the ergothioneine can be only biosynthesized in some fungi and mycobacteria, it was probably assimilated by the sponge through dietary intake or it is present in the microbial symbionts of the sponge. As regards with the presence of the Se-methylselenoneine in the urine sample, no explanation about its origin can be given yet but as selenoneine appears to be a major selenium compound in tissues of some fishes, it can be postulated that its origin is probably from the diet of the volunteers and that it was later on partially methylated, most likely by methyltransferase enzymes present in liver or kidney.…”

Section: Identification Of Selenocompounds Present In Urine By Coupli...mentioning

confidence: 99%

Identification in human urine and blood of a novel selenium metabolite, Se-methylselenoneine, a potential biomarker of metabolization in mammals of the naturally occurring selenoneine, by HPLC coupled to electrospray hybrid linear ion trap-orbital ion trap MS

et al. 2011

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Speciation analysis of selenium in human urine allowed for the first time the identification of a novel selenium metabolite, Se-methylselenoneine. Despite a concentration at low ppb level, its characterization was achieved after sample purification by solid phase extraction (SPE) followed by the parallel coupling of the bidimensional RP/HILIC chromatography with ICP-MS and ESI-LTQ Orbitrap MS detection. To confirm its biological significance with regards to selenoneine, the recently discovered analog of ergothioneine, and to discard the possibility of sample preparation artifacts, a new method was developed to monitor its actual presence, as well as the occurrence of its sulfur and/or non-methylated analogs, in non-preconcentrated urine and blood samples of non-supplemented humans. It consisted in a HILIC ESI-MS(3) method in high resolution mode (resolution 30 000 at m/z 400) with large isolation width windows for precursor ions. These two particular settings allowed respectively to keep observing the specific mass defect of selenium- and sulfur-containing molecules and to maintain the characteristic selenium pattern in product ions created through MS(n) fragmentations. As a result, all four metabolites were detected in blood and three of them in urine. Moreover, different ratios "methylated/non-methylated" were observed between urine and blood samples, which seemed to indicate their active metabolization. The analytical tool developed here will be of a great importance to further study the occurrence and the potential metabolic role in mammalian organelles, cells and fluids of these very particular and promising redox metabolites.

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“…Azoricasterol ( 105 ) is the first metabolite isolated from Macandrewia azorica (Figure 29) [103]. The specimen was collected from a depth of 600 m off the flanks of the Gettysburg and Ormonde Sea Mount in the North Atlantic by benthic dredging.…”

Section: Sterols Lipids and Fatty Acidsmentioning

confidence: 99%

Natural Products from the Lithistida: A Review of the Literature since 2000

2011

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Lithistid sponges are known to produce a diverse array of compounds ranging from polyketides, cyclic and linear peptides, alkaloids, pigments, lipids, and sterols. A majority of these structurally complex compounds have very potent and interesting biological activities. It has been a decade since a thorough review has been published that summarizes the literature on the natural products reported from this amazing sponge order. This review provides an update on the current taxonomic classification of the Lithistida, describes structures and biological activities of 131 new natural products, and discusses highlights from the total syntheses of 16 compounds from marine sponges of the Order Lithistida providing a compilation of the literature since the last review published in 2002.

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Isolation and structure elucidation of azoricasterol, a new sterol of the deepwater sponge Macandrewia azorica

Cited by 9 publications

References 29 publications

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

Identification in human urine and blood of a novel selenium metabolite, Se-methylselenoneine, a potential biomarker of metabolization in mammals of the naturally occurring selenoneine, by HPLC coupled to electrospray hybrid linear ion trap-orbital ion trap MS

Natural Products from the Lithistida: A Review of the Literature since 2000

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