Property investment and development business W G Mitchell has had 30 out of 75 of its divisions placed into administration.
Northern Irish brothers Patrick and Hugh Hegarty own the £500m property company.
The administrators Ernst & Young are to continue running the distressed businesses while looking into selling them.
The properties owned by the businesses in administration include two hotels in Edinburgh's Grassmarket, which WG Mitchell acquired for £54m in October 2006.
The portfolio also includes property on Charlotte Square and George Street in Edinburgh, the 200,000 sq. ft. Richmond shopping centre in Derry and properties in Glasgow and Perth in Aberdeenshire. The properties are leased to third parties.
The Hegarty family began building their property portfolio in Northern Ireland in the 1960s. It was estimated in the 2008 Sunday Times rich list that Patrick Hegarty and his family had a fortune of £40m.
