Aplysiid egg compounds

September 22, 2000
From: Kirsten Benkendorff

Hi Bill,

Following on your reply to Nerissa's question, here is what I know about toxic compounds from Aplysiidae egg masses. It probably doesn't help much in deciding whether Dolabella eggs are toxic but I don't think I would be eating them based on this info - at least without boiling them really well!

The most interesting compound is a lipid, diacyl hexadecylglycerol, which has been isolated from the egg masses of Aplysia kurodai. This compound is known to have laxative properties and is also thought to cause vomitting in people. A range of novel sterols have also been isolated from this species and A. juliana, which are thought to function as defensive substances based on the biological activities of similar sterols.

Antineoplastic and cytolytic glycoproteins have been isolated from the egg masses of A. juliana and A. kurodai. Antitumor activity has also been reported in the egg mass of Dolabella auricularia but the cytolytic factor has not been isolated. It appears to be different from the compounds isolated from the Aplysia spp. but is still likely to be a glycoprotein, which would be destroyed by heating.

A factor capable of agglutinating vertebrate blood cells has been isolated from Aplysia kurodai eggs, which appears to be a protein that decomposes after heating at 60 degrees.

I found a range of small chlorinated compounds in the freeze dried eggs of Aplysia juliana including chloro propene, dichloropropene and di and tri chloro propanone. These compounds are known to have mutagenic and cytotoxic effects. However, these compounds were not present in the freshly extracted egg mass, suggesting that they could have been breakdown products, possibly from the dietary derived chlorinated terpenes that are commonly found in Aplysia adults.

I also found a range of long chained saturated and unsaturated fatty acids in Aplysia egg masses. Most of these are standard compounds that are unlikely to be toxic, although several could not be identified. It is therefore of interest that a range of novel lactonized dihydroxyfatty acids have been isolated fron the skin of Aplysia depilans, which have ichthyotoxic properties.

Cheers,
Kirsten Benkendorff
Coordinator
Marine Bioprospecting Initiative
Departments of Biological Sciences and Chemistry
University of Wollongong, NSW, 2522

kirsten@uow.edu.au

Benkendorff, K., 2000 (Sep 22) Aplysiid egg compounds. [Message in] Sea Slug Forum. Australian Museum, Sydney. Available from http://www.seaslugforum.net/find/3065

Thanks Kirsten,
It is indeed surprising they are eaten, but it seems they are a regular part of some people's diets in Fiji and the Philippines. One other interesting point about aplysiid eggs that needs further study is their colour. In my reply to Nerissa's message I mentioned reports of studies showing that egg colour was dependent on the colour of the algae eaten by the adults. I have just noticed Itai Plaut's report that the eggs of Aplysia oculifera change colour during development, which certainly occurs in other opisthobranchs.

Perhaps I should start a page on aplysiid eggs to summarise all this information.

Best wishes,
Bill Rudman.

Rudman, W.B., 2000 (Sep 22). Comment on Aplysiid egg compounds by Kirsten Benkendorff. [Message in] Sea Slug Forum. Australian Museum, Sydney. Available from http://www.seaslugforum.net/find/3065

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