Clavulones and related tert-hydroxycyclopentenone fatty acids: occurrence, physiological activity and problem of biogenetic origin

Grechkin, Alexander N.

doi:10.1016/0929-7855(94)00039-f

Cited by 18 publications

(9 citation statements)

References 61 publications

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“…Table 3 also summarizes the other bioactivities of compounds 1Ϫ8. As has been proposed, [38] clavulones may have an allelopathic role in corals. Their potent cytotoxicity may play a role in coral defense against some other marine organisms.…”

Section: Resultsmentioning

confidence: 86%

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Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Řezanka

Dembitsky

2002

Eur J Org Chem

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Eight new brominated oxylipins 1−8, including two glycosides, were isolated from the Red Sea invertebrates Dendrophyllia sp., Dendronephthya sp. (red variety), Dendronephthya sp. (yellow variety), and Tubipora musica. Their structures were elucidated mainly on the basis of NMR spectroscopic data. The relative and absolute configurations were determined by analysis of NOESY and CD data and by the IntroductionThe ongoing investigation of the chemical constituents of soft corals of the Anthozoa class has resulted in the isolation of a number of different active metabolites.[1] Among them, halogenated compounds Ϫ predominantly steroids, [2] diterpenes, [3] alkaloids, [4] and prostanoids [5] Ϫ have received much attention because of their strong antiinflammatory and antitumor activities. The chemistry of prostaglandins has now entered a new stage, thanks to newly discovered, predominantly halogenated, compounds. The first paper describing the isolation of prostaglandins from a Caribbean gorgonian coral [6] was published more than 30 years ago; 16 years later, halogen-substituted prostaglandins were isolated for the first time from an octocoral. [5] Marine prostanoids, predominantly halogenated, are distributed among a number of different marine sources and include, for example, chloro-punaglandins [7Ϫ10] from octocorals living in the Pacific ocean, chloro-epoxy prostanoids from Clavularia viridis, [11] punaglandins from Hawaiian octocorals, [5] and also substituted chloro-, bromo-, and iodovulones [12Ϫ16] from corals.Further metabolites with different but similar structures Ϫ including a cyclopentenone ring Ϫ were found in Dendrophyllia sp. They are similar to chromomoric acids B and F, isolated from Chromolaena morii and C. chasleae. [17,18] Chromomoric acid B methyl ester has also been found in other species such as Schistostepnium, [19] Montanoa, [20] and [a] 309 modified Mosher method. The compounds gave positive results in a brine shrimp toxicity assay, a sea urchin eggs test (Paracentrotus lividus), and a crown gall tumor on potato disks test (Agrobacterium tumefaciens).

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Section: Resultsmentioning

confidence: 86%

“…[37,38] Chlorovulone I shows strong antiproliferative and cytotoxic activity. The IC 50 value (for HL-60 cells) is 0.01 µg/mL.…”

Section: Resultsmentioning

confidence: 99%

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Řezanka

Dembitsky

2002

Eur J Org Chem

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“…1) (6). In corals, subsequent steps may lead to cyclic products such as the clavulones (4,7), although this connection remains to be proven.…”

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confidence: 99%

The structure of coral allene oxide synthase reveals a catalase adapted for metabolism of a fatty acid hydroperoxide

Oldham

Brash

Newcomer

2004

Proc. Natl. Acad. Sci. U.S.A.

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8R-Lipoxygenase and allene oxide synthase (AOS) are parts of a naturally occurring fusion protein from the coral Plexaura homomalla. AOS catalyses the production of an unstable epoxide (an allene oxide) from the fatty acid hydroperoxide generated by the lipoxygenase activity. Here, we report the structure of the AOS domain and its striking structural homology to catalase. Whereas nominal sequence identity between the enzymes had been previously described, the extent of structural homology observed was not anticipated, given that this enzyme activity had been exclusively associated with the P450 superfamily, and conservation of a catalase fold without catalase activity is unprecedented. Whereas the heme environment is largely conserved, the AOS heme is planar and the distal histidine is flanked by two hydrogen-bonding residues. These critical differences likely facilitate the switch from a catalatic activity to that of a fatty acid hydroperoxidase.eicosanoids ͉ heme

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“…There are a few that are biosynthesized enzymatically as single enantiomers such as prostaglandins (PGs, I) and thromboxanes (Txs, II) in animals, (9S,13S)-12-oxophytodienoic acid (OPDA, III) and jasmonic acids (JAs, IV) in plants, [6] and the clavulones V and punaglandins VI in marine invertebrates. [12] Isoprostanes (IsoPs) 2 b,c, isothromboxanes (IsoTxs) 3 b, and isofurans (IsoFs) 4 b are the cyclic compounds formed autoxidatively from 1 b and 1 c. Neuroprostanes (NeuroPs) 2 d, which are present in human and animal brain, are derived from 1 d. Phytoprostanes (PhytoPs) 2 a, which are derived from 1 a, are the major cyclic metabolites found in plants. The common features of all autoxidatively generated PUFA Jean-Marie Galano studied chemistry at Paul CØzanne UniversitØ Marseille and obtained his PhD under the supervision of HonorØ Monti in 2001.…”

Section: Classification Of Pufa Metabolitesmentioning

confidence: 99%

Beyond Prostaglandins—Chemistry and Biology of Cyclic Oxygenated Metabolites Formed by Free‐Radical Pathways from Polyunsaturated Fatty Acids

2008

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Polyunsaturated fatty acids (PUFAs) are important constituents in all organisms. They fulfil many functions, ranging from modulating the structure of membranes to acting as precursors of physiologically important molecules, such as the prostaglandins, which for a long time were the most prominent cyclic PUFA metabolites. However, since the beginning of the 1990s a large variety of cyclic metabolites have been discovered that form under autoxidative conditions in vivo to a much larger extent than do prostaglandins. These compounds--isoprostanes, neuroprostanes, phytoprostanes, and isofurans--proved subsequently to be ubiquitous in nature. They display a wide range of biological activities, and isoprostanes have become the currently most reliable indicators of oxidative stress in humans. In a relatively short time, the structural variety, properties, and applications of the autoxidatively formed cyclic PUFA derivatives have been uncovered.

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Clavulones and related tert-hydroxycyclopentenone fatty acids: occurrence, physiological activity and problem of biogenetic origin

Cited by 18 publications

References 61 publications

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

The structure of coral allene oxide synthase reveals a catalase adapted for metabolism of a fatty acid hydroperoxide

Beyond Prostaglandins—Chemistry and Biology of Cyclic Oxygenated Metabolites Formed by Free‐Radical Pathways from Polyunsaturated Fatty Acids

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