Prince Andrew has been befriended by a Libyan-born businessman who in 2005 was convicted of buying a machine gun and trying to smuggle it into France. On a private visit to Tunisia earlier this month Andrew was shown around by his friend Tarek Kaituni, who has a house there. He also met Colonel Muammar Gadaffi, the Libyan president.

Andrew and Kaituni, who were introduced by a Middle Eastern sheikh, are regularly seen together on the European party circuit and last year both attended a lavish VIP hunting trip in Kazakhstan hosted by the country’s president.

Andrew’s choice of associates has come under scrutiny since The Sunday Times revealed earlier this year that he had sold Sunninghill Park, his former home in Berkshire, for more than £3m over the asking price to senior Kazakh figures. It has since been left to rot.

Both Andrew and Kaituni are friends of Goga Ashkenazi, the Kazakh-born socialite who has been linked to the Sunninghill Park purchase. Kaituni has also told friends that he is trying to interest Andrew in a potential business deal.

The Duke of York is apparently unaware that Kaituni was arrested in Paris in November 2004 for buying a weapon, understood to be a machinegun. Last week the chief prosecutor’s office in Paris confirmed that Kaituni was given a two-month suspended sentence and fined ¤10,000 (£7,880) by the city’s correctional tribunal in November 2005.

According to former associates of Kaituni, he employed a taxi driver to import the weapon from Amsterdam. The driver was stopped by police and said he was working on Kaituni’s instructions.

Salam Said, a property developer in Qatar and former business associate of Kaituni, said Kaituni had bought the gun after his ex-wife Lisa Van Goinga, a fashion model, left him for Matteo Marzotto, a senior executive at the Valentino and Marzotto fashion group.

Said, director of The Land, a Qatar-based property developer, said: “At a meeting in Paris in November he \ told me that he was with this girl in Turkey and she left him for his friend . . . he got depressed.

“He got his driver to bring a gun from Holland. He was trying to show he was tough. He said the guy was stupid; he got caught at the borders with the gun.”

Marzotto, who is based in Italy, was invited by police to come to Paris, where he gave a deposition. According to a friend, police told him they had found pictures of him and Van Goinga at Kaituni’s house, together with pictures of properties that Marzotto owned.

Kaituni was not charged with any violent offence or threatening behaviour.

A source close to Kaituni said he and Andrew were close friends: “Kaituni has been telling people that Andrew visited Tunisia at his invitation. They have met dozens of times.”

When initially approached, Kaituni confirmed that he knew Andrew but said he needed to speak to the prince before discussing the visit further.

He later admitted meeting Andrew that trip, but said the two were not friends. “I don’t know Andrew, I’m a simple guy . . . he was here and I just happened to see him one day,” he said.

Kaituni also denied that he had been convicted of buying a gun, claiming he was in Qatar at the time of the arrest. “It’s not true. I’m not the only Kaituni in the world, there’s thousands in Libya,” he said.

Andrew met Gadaffi at a dinner in the Libyan president’s honour in the Tunisian resort of Gammarth. The Libyan embassy in London said the meeting was “unplanned”.

A spokeswoman for Prince Andrew said he was on holiday and unavailable for comment.

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