Russia says it has for the first time hit targets in Syria with missiles launched from a submarine.
Defence Minister Sergei Shoigu said Kalibr cruise missiles from the Rostov-on-Don submarine were fired at so-called Islamic State (IS) militants, at two "terrorist positions" in Raqqa.
Russia began air strikes in Syria in September, saying this had been requested by President Bashar al-Assad.
A US-led coalition says Russia often targets moderate Syrian opposition.
The Kremlin denies the accusations.
It says it is hitting "all terrorists", but at least some of its air strikes have hit civilians and Western-backed rebels, according to Syrian activists.
"We used Kalibr cruise missiles from the Rostov-on-Don submarine from the Mediterranean Sea," Mr Shoigu said in televised meeting with President Vladimir Putin on Tuesday.
"We can say with complete confidence that fairly serious damage was done to weapons stores and a factory for preparing mines and, naturally, oil infrastructure," the defence minister added.
Raqqa, in northern Syria, is the self-proclaimed capital of the IS militant group.
Mr Shoigu also said that Russia had informed the US and Israel in advance about the missile strikes.
Neither country has publicly commented on the issue.
In October, Russia said it had fired 26 sea-based cruise missiles from warships in the Caspian Sea - about 1,500km (930 miles) away from targets in Syria.
The US-led coalition has been targeting IS militants in Syria since September 2014, and does not co-ordinate its raids with the authorities in Damascus.