Palaeontologists have just identified three new species of fossil octopus discovered in Cretaceous rocks in Lebanon. The five specimens, described are 95 million years old but, astonishingly, preserve the octopuses' eight arms with traces of muscles and those characteristic rows of suckers. Even traces of the ink and internal gills are present in some specimens.
What surprised the scientists most was how similar the specimens are to modern octopus: 'these things are 95 million years old, yet one of the fossils is almost indistinguishable from living species." This provides important evolutionary information. "The more primitive relatives of octopuses had fleshy fins along their bodies. The new fossils are so well preserved that they show, like living octopus, that they didn't have these structures.'
This pushes back the origins of modern octopus by tens of millions of years. link
Ref: New Octopods (Cephalopoda: Coleoidea) from the Late Cretaceous (Upper Cenomanian) of Hakel and Hadjoula, Lebanon. 2009. D. Fuchs, et al. Palaeontology
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Adventure Comics #202 (1954); Art by Ralph Mayo