Hydroxydanaidal is an insect
pheromone synthesized by some species of moth from
pyrrolizidine alkaloid
Pyrrolizidine alkaloids (PAs), sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine. Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect he ...
s found in their diet.
Use
The caterpillars of several kinds of
arctiid moth
The Arctiinae (formerly called the family Arctiidae) are a large and diverse subfamily of moths with around 11,000 species found all over the world, including 6,000 neotropical species.Scoble, MJ. (1995). ''The Lepidoptera: Form, Function and D ...
ingest pyrrolizidine alkaloids—substances which plants produce to deter herbivores—and use them as protection against insectivores. The larva converts the alkaloid into an
''N''-oxide for storage; on metamorphosis, the alkaloid is retained and used by the adult. This was discovered after the observation that ''
Utetheisa ornatrix
''Utetheisa ornatrix'', also called the bella moth, ornate moth or rattlebox moth is a moth of the subfamily Arctiinae. It is aposematically colored ranging from pink, red, orange and yellow to white coloration with black markings arranged in va ...
'' moths caught in spiderwebs were cut loose by the spiders.
Many insects that carry pyrrolizidine alkaloids are brightly-colored to signal their toxicity.
Male tiger moths convert the alkaloid through various intermediate stages
into the
pheromone hydroxydanaidal;
[{{cite journal , journal=J Chem Ecol , author=J A Edgar, M Boppré, E Kaufmann , title=Insect-synthesised Retronecine Ester Alkaloids: Precursors of the Common Arctiine (Lepidoptera) Pheromone Hydroxydanaidal , volume=33 , issue=12 , pages=2266–2280, pmid=18030534 , year=2007 , last2=Boppré , last3=Kaufmann , doi=10.1007/s10886-007-9378-y , s2cid=8963122 ] female moth prefer males with more pheromone, since the alkaloid will be transferred into her eggs and protect them from predation.
References
Insect pheromones
Aromatic aldehydes
Secondary alcohols
Pyrrolizidine alkaloids