Alan swept his spot-kick past Jose Reina after Sotirios Kyrgiakos had needlessly fouled Brazilian Mossoro in the area, paving the way for the Portuguese side to claim a shock 1-0 win.

Kenny Dalglish's men seldom threatened and Braga could have made it more with Hugo Viana troubling Reina with a free-kick and full-back Silvio beating the keeper but rattling the crossbar.

There was more action in Germany where Villarreal's Brazilian striker Nilmar came off the bench to net a dramatic double and wrap up a 3-2 victory over Bayer Leverkusen.

The Spaniards had fallen behind to Michal Kadlec's 33rd-minute opener but were level before the break through Giuseppe Rossi and Nilmar nudged the visitors ahead with his first after 70 minutes.

Gonzalo Castro equalised less than two minutes later but as the game headed into injury time Nilmar finished off a surging run with his second goal to leave his side well in control.

Fredy Guarin fired home from the edge of the box in the 70th minute to give Porto a superb 1-0 win over CSKA Moscow at the Luzhniki Stadium and the advantage heading back to Portugal next week.

Rangers shut out PSV Eindhoven in their first leg in Holland with Marcelo and Marcus Berg both missing golden chances for the Dutch outfit and recalled keeper Neil Alexander performing heroics in the Rangers goal.