The last time Russia fired Kalibr cruise missiles from its ships at militant targets in Syria was in November 2016.
A Russian warship and submarine fired four cruise missiles from the Mediterranean at Daesh targets near the Syrian city of Palmyra, the Russian Defence Ministry said on Wednesday.
The strike was the first of its kind since November 2016, according to Russian media. They reported that the frigate "Admiral Essen" and the submarine "Krasnodar" launched the missiles which targeted militants and equipment in an area east of Palmyra.
The defence ministry said the hardware and forces struck had previously been deployed by Daesh in its de facto Syrian capital, Raqqa.
"All targets were destroyed," the ministry said in a statement.
Russia had warned the United States, Turkey and Israel before launching the missiles, the ministry said.
It did not say when the strike took place, but Russian news agencies quoted Kremlin spokesman Dmitry Peskov as saying that Defence Minister Sergei Shoigu had personally told President Vladimir Putin about the military action late on Tuesday.
Russia is an ally of Syrian regime leader Bashar al Assad. Russian military intervention in the war in September 2015 turned the tide against a range of opposition groups backed by the US and its allies, including Turkey.