Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms

Adolph, Sven; Poulet, S. A.; Pohnert, Georg

doi:10.1016/s0040-4020(03)00382-x

Cited by 70 publications

(62 citation statements)

References 23 publications

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“…By contrast, saturated aldehydes are more stable and relatively non-toxic (Bruenner et al, 1994;Kruman et al, 1997;Spiteller, 2001). Recently, Adolph et al (2003) reported that the antiproliferative activity of diatom-derived fatty aldehydes on sea urchin embryos depends on the degree of unsaturation and length of the chain, and that saturated aldehydes were biologically less active than unsaturated aldehydes of the same chain length. We here confirm that the apoptogenic activity of an unsaturated diatom aldehyde (decadienal) is greater than that of a saturated aldehyde (decanal) in both sea urchin and copepod embryos.…”

Section: Discussionmentioning

confidence: 99%

A marine diatom-derived aldehyde induces apoptosis in copepod and sea urchin embryos

Romano

Russo

Buttino

et al. 2003

Journal of Experimental Biology

100

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SUMMARY The diatom-derived aldehyde 2-trans-4-trans-decadienal(DD) was tested as an apoptogenic inducer in both copepod and sea urchin embryos, using terminal-deoxynucleotidyl-transferase-mediated dUTP nick-end labelling (TUNEL), DNA fragmentation profiling (laddering) and an assay for caspase-3 activity. DD induced TUNEL positivity and DNA laddering, but not caspase-like activation, in copepod embryos spawned by females fed for 10-15 days the diatom diet Thalassiosira rotula Meunier (in vivo),or when newly spawned eggs were exposed for 1 h to 5 μg ml-1 DD(in vitro). To our knowledge, this is the first time that evidence for an apoptotic process in copepods has been obtained by cytochemical (TUNEL)and biochemical (DNA fragmentation) approaches. The absence of caspase-like activity in copepod embryos suggests that caspase-independent programmed cell death occurs in these organisms. In sea urchin embryos, DD induced apoptosis and also activated a caspase-3-like protease. The saturated aldehyde decanal induced apoptosis at higher concentrations and after a longer incubation period than DD, indicating that α,β-unsaturation of the molecule,coupled with the aldehyde group, is responsible for the greater biological activity of DD. Since diatoms are an important food source for marine herbivores such as copepods and sea urchins, these findings may help explain why unsaturated aldehydes often induce reproductive failure, with important ecological consequences at the population level.

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Section: Discussionmentioning

confidence: 99%

A marine diatom-derived aldehyde induces apoptosis in copepod and sea urchin embryos

Romano

Russo

Buttino

et al. 2003

Journal of Experimental Biology

100

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“…This property may explain the dynamics behind some blooms and also explain why oxylipin profiles can be used as an additional taxonomic identification tool, providing a functional feature to species characterization and morphological traits. Study on structure-activity relationship of oxylipins has revealed that the double bond geometry E/Z has no effects on inhibiting the development of embryos of sea urchin egg while the inhibition is primarily due to the chain length, the α, β, γ, δ-unsaturated aldehyde element, and the side chain polarity of PUAs (Adolph et al, 2003). Moreover, the biological importance of PUAs has been increasingly noted for their antimitotic and proapoptotic properties (Nappez et al, 1996), anti-inflammatory activity (Girona et al, 1997), anti-cancer activity (Sansone et al, 2014) and antimicrobial properties (Paul and Fenical, 1986).…”

Section: Oxylipinsmentioning

confidence: 99%

Exploring Valuable Lipids in Diatoms

et al. 2017

Front. Mar. Sci.

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Diatoms are one major group of algae in oceans that accounts almost half of marine primary food production and have also been identified as a promising candidate for biofuel production for their high level accumulation of lipids. They have gained increasingly attention for their potential applications in pharmaceuticals, cosmetics, nutrient supplements, and biofuels. This review aims to summarize the recent advances in diatom lipid study. Chemical structures and bioactivities of different lipid classes are discussed with a focus on valuable lipids such as fatty acids, polar lipids, steroids, and oxylipins from various diatoms species. Further, current extraction and fractionation approaches are compared and recent analytical techniques and methods are also reviewed with an emphasis on lipid class composition and fatty acid profiling. Biosynthetic pathways and key catalyzing enzymes are illustrated for a better understanding of fatty acid metabolism. Past engineering attempts toward generating appropriate diatom strains for lipid production are discussed with examples using mutagenesis, environmental stimulants, and genetic modification methods. Some possible future directions and applications of diatom-derived lipids are also proposed.

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“…Like most ␣,␤,␥,␦-unsaturated aldehydes, 12-ODTE exhibits antiproliferative activity against fast growing and dividing cells (33,34). The 12-ODTE producing PpLOX1 might accordingly be regarded as enzyme involved in an activated chemical defense of P. patens although pathogens or herbivores that might be targeted by this chemical are not identified as of yet.…”

Section: Table I Hydroperoxides Formed From the Reaction Of Pplox1 Wimentioning

confidence: 99%

A Multifunctional Lipoxygenase with Fatty Acid Hydroperoxide Cleaving Activity from the Moss Physcomitrella patens

Senger

Wichard

Kunze

et al. 2005

Journal of Biological Chemistry

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A complex mixture of fatty acid-derived aldehydes, ketones, and alcohols is released upon wounding of the moss Physcomitrella patens. To investigate the formation of these oxylipins at the molecular level we isolated a lipoxygenase from P. patens, which was identified in an EST library by sequence homology to lipoxygenases from plants. Sequence analysis of the cDNA showed that it exhibits a domain structure similar to that of type2 lipoxygenases from plants, harboring an N-terminal import signal for chloroplasts. The recombinant protein was identified as arachidonate 12-lipoxygenase and linoleate 13-lipoxygenase with a preference for arachidonic acid and eicosapentaenoic acid. In contrast to any other lipoxygenase cloned so far, this enzyme exhibited in addition an unusual high hydroperoxidase and also a fatty acid chain-cleaving lyase activity. Because of these unique features the pronounced formation of (2Z)-octen-1-ol, 1-octen-3-ol, the dienal (5Z,8Z,10E)-12-oxo-dodecatrienoic acid and 12-keto eicosatetraenoic acid was observed when arachidonic acid was administered as substrate. 12-Hydroperoxy eicosatetraenoic acid was found to be only a minor product. Moreover, the P. patens LOX has a relaxed substrate tolerance accepting C 18 -C 22 fatty acids giving rise to even more LOX-derived products. In contrast to other lipoxygenases a highly diverse product spectrum is formed by a single enzyme accounting for most of the observed oxylipins produced by the moss. This single enzyme might, in a fast and effective way, be involved in the formation of signal and/or defense molecules thus contributing to the broad resistance of mosses against pathogens.

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Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms

Cited by 70 publications

References 23 publications

A marine diatom-derived aldehyde induces apoptosis in copepod and sea urchin embryos

A marine diatom-derived aldehyde induces apoptosis in copepod and sea urchin embryos

Exploring Valuable Lipids in Diatoms

A Multifunctional Lipoxygenase with Fatty Acid Hydroperoxide Cleaving Activity from the Moss Physcomitrella patens

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