Synthesis of Enantiomerically Pure Pheromones of South‐Pacific Brown Algae: Hormosirene and Dictyopterene A

Schotten, Theo; Boland, Wilhelm; Jaenicke, Lothar

doi:10.1002/hlca.19850680514

Cited by 30 publications

(13 citation statements)

References 19 publications

(10 reference statements)

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“…Evaporation of the analytes from the fibre was directly performed within the injection port (220°C) of the GC-MS (DB225-MS column, Alltech; T-program: 50°C [2 min, splitless]; ramped with 10°C min -1 to 200°C and with 30°C min -1 to 280°C [2 min]). Unsaturated aldehydes were identified as described (Pohnert 2000); long-chain aldehydes and volatile hydrocarbons were identified by comparison with synthetic (Schotten et al 1985) or commercially available reference compounds.Total fatty acid analysis. The analysis of total fatty acids was performed after trans-esterification following a modified procedure of Lepage & Roy (1984) (Rodriguez-Ruiz et al 1998).…”

mentioning

confidence: 99%

Are volatile unsaturated aldehydes from diatoms the main line of chemical defence against copepods?

Pohnert¹,

Lumineau²,

Cueff³

et al. 2002

Mar. Ecol. Prog. Ser.

127

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New experiments comparing the effects of 3 species of phytoplankton Prorocentrum minimum Schiller 1933 (PM), Thalassiosira rotula Meunier 1910 strains (TR1) and (TR2), and Skeletonema pseudocostatum (SPC) on the fecundity and egg-hatching rates of Calanus helgolandicus females are described. To further determine the chemical factors causing the inhibitory process related to diatoms, the biological findings were linked with an analysis of aldehydic oxylipins (metabolites derived from the oxidative transformation of fatty acids). Members of this compound class have previously been reported to inhibit copepod egg development. Comparison of the inhibitory properties with results from the chemical analysis, as well as bioassays with synthetic samples using sea urchin eggs as a model system, showed that the observed effect is not restricted to the previously identified volatile aldehydes decadienal and decatrienal but, in fact, depends on a reactive structural element (α,β,γ,δ-unsaturated aldehyde). In addition, the fatty acid content of the algae was verified with special emphasis on eicosapentaenoic acid (EPA), which is currently under discussion for its metabolic value and defensive potential. Our results demonstrate that only certain diatoms inhibit hatching in copepods and that this effect is independent of the EPA content of the diet. Moreover, saturated aldehydes, like the widely distributed tridecanal, did not affect our assay with sea urchin eggs. Since the observed hatching inhibition, as well as the capability for the formation of reactive aldehydes, is highly species and even isolate dependent, it would appear that no prediction of food quality of certain species can be given without a detailed analysis.KEY WORDS: Phytoplankton · Oxylipin · Diatom · Copepod · Hatching · Inhibition · Activated defence Resale or republication not permitted without written consent of the publisherMar Ecol Prog Ser 245: [33][34][35][36][37][38][39][40][41][42][43][44][45] 2002 nature of the factors that have anti-proliferative properties in marine pelagic algae and their ecological relevance. Miralto et al. (1999) identified reactive volatile aldehydes from the diatom Thalassiosira rotula Meunier 1910 (TR1) with the ability to inhibit egg hatching in copepods. As shown in Fig. 1, these aldehydes, namely 2E,4Z-decadienal (hereafter decadienal) and 2E,4Z,7Z-decatrienal (hereafter decatrienal) are derived from arachidonic acid (C20:4 n-6) and eicosapentaenoic acid (EPA, C20:5 n-3), respectively (Pohnert 2000). These metabolites thus belong to the oxylipins, a class of compounds that is by definition derived from the oxidative transformation of fatty acids. Their formation is initialised by the action of lipoxygenases, an enzyme class that has been previously detected to be active in numerous diatoms ( Fig. 1) (for a review see Pohnert & Boland 2002). For example, the freshwater diatom Gomphonema parvulum uses EPA as a precursor for the formation of hormosirene, a volatile C11-hydrocarbon released together with a seco...

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mentioning

confidence: 99%

Are volatile unsaturated aldehydes from diatoms the main line of chemical defence against copepods?

Pohnert¹,

Lumineau²,

Cueff³

et al. 2002

Mar. Ecol. Prog. Ser.

127

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“…Many of these compounds are produced by the organism with the primary function of attracting male gametes to complete sexual reproduction, but some have also been shown to function as effective anti-predation agents, or may even be used to interfere with other pheromone communication systems of competing alga [103,104]. Many species of brown algae reported herein, including X. chondrophylla, Scytosiphon lomentaria and Hormosira banksii, have been found to produce the sexual pheromone hormosirene (309), suggesting that this is a particularly important pheromone for the phylum Ochrophyta [103,105]. The brown alga C. peregrina has been found to exhibit the pheromone (304), which has long been suspected as a sperm attractant for this and many other species [106].…”

Section: Miscellaneousmentioning

confidence: 95%

“…Terpenoids that populate this class are both acyclic and cyclic and are identified by terminal ketone or aldehyde functional groups, followed by C-15 or C-20 terpenoid tails. There are multiple varieties of mono-and sesquiterpenes including farnesylacetone epoxides (92)(93)(94), cyclic farnesylacetones (102)(103)(104)(105)(106)(107)(108)(109)(110), farnesylacetones (95-97, 101), geranylacetones (100) and geranylgeranal epoxides (98, 99) (see Supporting Information Figure S12). All compounds in this class were isolated and characterised from the alga Cystophora moniliformis [58,68,[70][71][72].…”

Section: Sesquiterpenes and Monoterpenesmentioning

confidence: 99%

Natural Products of Marine Macroalgae from South Eastern Australia, with Emphasis on the Port Phillip Bay and Heads Regions of Victoria

et al. 2020

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Marine macroalgae occurring in the south eastern region of Victoria, Australia, consisting of Port Phillip Bay and the heads entering the bay, is the focus of this review. This area is home to approximately 200 different species of macroalgae, representing the three major phyla of the green algae (Chlorophyta), brown algae (Ochrophyta) and the red algae (Rhodophyta), respectively. Over almost 50 years, the species of macroalgae associated and occurring within this area have resulted in the identification of a number of different types of secondary metabolites including terpenoids, sterols/steroids, phenolic acids, phenols, lipids/polyenes, pheromones, xanthophylls and phloroglucinols. Many of these compounds have subsequently displayed a variety of bioactivities. A systematic description of the compound classes and their associated bioactivities from marine macroalgae found within this region is presented.

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“…Chemoenzymatic syntheses of these compounds have been carried out through optical resolution of racemic synthons [192,193,194]. For example, enantiomerically pure dictyopterenes A (48) and C' (49) were synthesized through enzymatic hydrolysis of cis-1,2-bis(butyryloxymethyl) cyclopropane to give optically pure cis-(1S, 2R)-1-hydroxymethyl-2-butyryloxymethylcyclopropane, a versatile cyclopropane synthon [195].…”

Section: Synthesis Of Other Pheromonesmentioning

confidence: 99%

Biocatalysis Applied to the Synthesis of Pheromones

Aleu¹,

Bustillo²,

Hernández-Galán³

et al. 2007

COC

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The application of biologically derived catalysts to the synthesis of agrochemicals has become increasingly popular in recent years. In most cases, the aim of using a biotransformation is either to introduce chirality into the molecule, to achieve a regioselective functionalization, or to selectively convert a functional group among other groups with similar reactivity. Pheromones, which have recently been commercialized as agrochemicals, are generally used in enantiopure forms with their intentional mixtures. Since they are usually highly effective, only very small quantities are needed to achieve the desired activity. This review, with approximately 200 references covering the period previous to December 2004, describes various efficient means of preparing optically pure pheromones and their precursors with the aid of isolated enzymes and microorganisms serving as catalysts.

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Synthesis of Enantiomerically Pure Pheromones of South‐Pacific Brown Algae: Hormosirene and Dictyopterene A

Cited by 30 publications

References 19 publications

Are volatile unsaturated aldehydes from diatoms the main line of chemical defence against copepods?

Are volatile unsaturated aldehydes from diatoms the main line of chemical defence against copepods?

Natural Products of Marine Macroalgae from South Eastern Australia, with Emphasis on the Port Phillip Bay and Heads Regions of Victoria

Biocatalysis Applied to the Synthesis of Pheromones

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