Isolation and Absolute Configuration Determination of Aliphatic Sulfates as the Daphnia Kairomones Inducing Morphological Defense of a Phytoplankton-Part 2

Yasumoto, Ko; Nishigami, Akinori; Aoi, Hiroaki; Tsuchihashi, Chise; Kasai, Fumie; Kusumi, Takenori; Ooi, Takashi

doi:10.1248/cpb.56.129

Cited by 24 publications

(31 citation statements)

References 7 publications

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“…Recently, the chemical nature of the natural colony-inducing chemicals released from Daphnia has been elucidated and the active substances were identified as different aliphatic sulfates (Yasumoto et al 2005; 2006; 2008a, b). These compounds are closely related to commonly used manmade anionic surfactants.…”

Section: Discussionmentioning

confidence: 99%

“…The surfactant FFD-6 induced a response similar to the one evoked by the natural information conveying chemicals. These natural active substances have been extracted from Daphnia and could be identified as different aliphatic sulfates and sulfamates showing strong structural similarity with synthetic anionic surfactants (Yasumoto et al 2005, 2006, 2008a, b). Hence, despite various anionic surfactants have been classified as not dangerous to the environment with respect to their effect on Daphnia (Verge and Moreno 2000), the FFD-6-induced morphological effect might indicate potential adverse effects on the energy-flow from algae to higher trophic levels at concentrations previously thought to be safe.…”

Section: Introductionmentioning

confidence: 99%

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Effects of an anionic surfactant (FFD-6) on the energy and information flow between a primary producer (Scenedesmus obliquus) and a consumer (Daphnia magna)

2011

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The effects of a commercially available anionic surfactant solution (FFD-6) on growth and morphology of a common green alga (Scenedesmus obliquus) and on survival and clearance rates of the water flea Daphnia magna were studied. The surfactant-solution elicited a morphological response (formation of colonies) in Scenedesmus at concentrations of 10–100 μl l−1 that were far below the No Observed Effect Concentration (NOEC) value of 1,000 μl l−1 for growth inhibition. The NOEC-value of FFD-6 for colony-induction was 3 μl l−1. Daphnia survival was strongly affected by FFD-6, yielding LC50–24h and LC50–48h of 148 and 26 μl l−1, respectively. In addition, clearance rates of Daphnia feeding on unicellular Scenedesmus were inhibited by FFD-6, yielding a 50% inhibition (EC50–1.5h) at 5.2 μl l−1 with a NOEC of 0.5 μl l−1. When Daphnia were offered FFD-6-induced food in which eight-celled colonies (43 × 29 μm) were most abundant, clearance rates (~0.14 ml ind.−1 h−1) were only 25% the rates of animals that were offered non-induced unicellular (15 × 5 μm) Scenedesmus (~0.56 ml ind.−1 h−1). As FFD-6 concentrations in the treated food used in the experiments were far below the NOEC for clearance rate inhibition, it is concluded that the feeding rate depression was caused by the altered morphology of the Scenedesmus moving them out of the feeding window of the daphnids. The surfactant evoked a response in Scenedesmus that is similar to the natural chemically induced defensive reaction against grazers and could disrupt the natural information conveyance between these plankton organisms.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effects of an anionic surfactant (FFD-6) on the energy and information flow between a primary producer (Scenedesmus obliquus) and a consumer (Daphnia magna)

2011

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“…Some types of kairomones have been isolated and identified. For example, aliphatic sulfates and sulfamates [242][243][244] as well as an artificial substitute (octyl sodium sulfate) have been found to induce colony formation in Scenedesmus sp. and Desmodesmus sp.…”

Section: Infochemicalsmentioning

confidence: 99%

A review of potential methods for zooplankton control in wastewater treatment High Rate Algal Ponds and algal production raceways

et al. 2015

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“…A first attempt to analyse the infochemicals released by daphnids was made by Van Holthoon et al (2003). Some years ago, Yasumoto et al (2005Yasumoto et al ( , 2008 reported a major breakthrough with a bioassayguided characterization of infochemicals from a 10-kg sample of Daphnia. After several chromatographic steps, eight aliphatic sulphates that are active at low concentrations (\1 ng ml -1 ) were isolated and fully characterized.…”

Section: Morphological Defences In Phytoplanktonmentioning

confidence: 99%

Induced defences in marine and freshwater phytoplankton: a review

2010

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Many organisms have developed defences to avoid predation by species at higher trophic levels. The capability of primary producers to defend themselves against herbivores affects their own survival, can modulate the strength of trophic cascades and changes rates of competitive exclusion in aquatic communities. Algal species are highly flexible in their morphology, growth form, biochemical composition and production of toxic and deterrent compounds. Several of these variable traits in phytoplankton have been interpreted as defence mechanisms against grazing. Zooplankton feed with differing success on various phytoplankton species, depending primarily on size, shape, cell wall structure and the production of toxins and deterrents. Chemical cues associated with (i) mechanical damage, (ii) herbivore presence and (iii) grazing are the main factors triggering induced defences in both marine and freshwater phytoplankton, but most studies have failed to disentangle the exact mechanism(s) governing defence induction in any particular species. Induced defences in phytoplankton include changes in morphology (e.g. the formation of spines, colonies and thicker cell walls), biochemistry (such as production of toxins, repellents) and in life history characteristics (formation of cysts, reduced recruitment rate). Our categorization of inducible defences in terms of the responsible induction mechanism provides guidance for future work, as hardly any of the available studies on marine or freshwater plankton have performed all the treatments that are required to pinpoint the actual cue(s) for induction. We discuss the ecology of inducible defences in marine and freshwater phytoplankton with a special focus on the mechanisms of induction, the types of defences, their costs and benefits, and their consequences at the community level.

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Isolation and Absolute Configuration Determination of Aliphatic Sulfates as the Daphnia Kairomones Inducing Morphological Defense of a Phytoplankton-Part 2

Abstract: The countercations were not identified and expressed as M.Chart 1. Synthesis of (1S,2S)-2-ACyclo-COOH Ester 4

Cited by 24 publications

References 7 publications

Effects of an anionic surfactant (FFD-6) on the energy and information flow between a primary producer (Scenedesmus obliquus) and a consumer (Daphnia magna)

Effects of an anionic surfactant (FFD-6) on the energy and information flow between a primary producer (Scenedesmus obliquus) and a consumer (Daphnia magna)

A review of potential methods for zooplankton control in wastewater treatment High Rate Algal Ponds and algal production raceways

Induced defences in marine and freshwater phytoplankton: a review

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