Aplysioviolin
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3D model (
JSmol ) |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C34H40N4O6 | |
Molar mass | 600.716 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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![](http://upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Aplysia_californica.jpg/220px-Aplysia_californica.jpg)
Aplysioviolin is a purple-colored
Biosynthetic origin
Aplysioviolin is a metabolic product of Aplysia californica species of sea hare, and is a major component to its ink mixture. Sea hares first consume red algae as nutriment, and extract from it the light-harvesting pigment phycoerythrin, cleaving it to separate the red-colored chromophore phycoerythrobilin from its covalently-bound protein structure. The sea hare then methylates one of phycoerythrobilin's two carboxylic acid functional groups to form aplysioviolin, which is concentrated and then stored in the ink gland.[2]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/4/4d/APV_Mech.jpg/340px-APV_Mech.jpg)
Mechanism of action
Aplysioviolin, when squirted or otherwise exposed to predators, causes avoidance behavior that allows the sea hare to escape from being eaten. While its effects on predatory behavior have been investigated, the precise enzymatic targets of aplysioviolin are as of yet unknown. The behavioral effects of aplysioviolin have been especially characterized in blue crabs, whose feeding behavior is relatively easy to observe. In addition however, aplysioviolin has been shown to deter the approach of
History
Aplysioviolin, along with the other components of sea hare ink, has been utilized as a dye since antiquity. Aplysioviolin in particular has been implicated in
![](http://upload.wikimedia.org/wikipedia/commons/1/18/APV_Rudiger.jpg)
Human applications
The principal application of aplysioviolin has been historically in dyeing textiles. Aplysioviolin, in contrast to other more widely-used dyes, is considered a light-sensitive arylmethane dye, and is thus known for fading over time. Other pigments have been similarly extracted from marine animals, including Tyrian purple (6,6-dibromoindigo), from Murex purpuream shellfish, and additionally used as dyes.
Aplysioviolin has seen renewed interest in recent years due to its application to medicine and optical microscopy. Especially given its chirality, aplysioviolin and other natural compounds may serve as useful tools for stereoselective drug production and directed optical polarization. Within the past decade, aplysioviolin has additionally been hypothesized to confer medical pharmacodynamic effects. While as of yet uncharacterized in humans, the bioactive effects seen in fish are hypothesized to be recapitulated in some form in mammalian organisms.[9]
References
- ^ S2CID 53162083.
- ^ PMID 21705367.
- PMID 28217773.
- ^ Kitrossky, Levi. "Do We Know Tekhelet?" (PDF). Retrieved 24 April 2018.
- ISBN 978-3-642-80768-8.
- PMID 6033876.
- S2CID 4221727.
- PMID 5776242.
- S2CID 83074451.