The U.S. on Friday sanctioned four companies that transported crude oil from Venezuela to Cuba, according to the Treasury Department.

Three of the companies — Jennifer Navigation Ltd., Lima Shipping Corp. and Large Range Ltd. — are based in Monrovia, Liberia, and the fourth, PB Tankers SpA, is based in Italy, the Treasury said. Treasury also identified nine vessels as blocked property owned by the four companies.

Four of the vessels — NEDAS, NEW HELLAS, S-TROTTER and SILVER POINT — delivered crude oil or oil products to Cuba over the course of 2019, according to the Treasury.