A British subsidiary of mining giant Glencore has been ordered to pay more than £275 million for bribing officials in African countries to gain access to oil.
The company paid $26m (£23m) through agents and employees to crude oil company officials in Nigeria, Cameroon and Ivory Coast between 2011 and 2016.
Prosecutors said Glencore Energy UK employees and agents used private jets to transfer money to pay bribes.
Glencore Energy UK pleaded guilty to seven corruption offences in June.
He was fined £182.9 million by Judge Peter Fraser of Southwark Crown Court, who also approved the forfeiture of £93.5 million from the company.
In addition to five corruption charges, the subsidiary admitted charges of failing to prevent officials from using bribes to secure oil contracts in Equatorial Guinea and South Sudan.
Mr Justice Fraser said that the offences to which Glencore had pleaded guilty amounted to "corporate corruption on a massive scale, deploying very substantial sums of money in bribes".
"The corruption is long-standing and has taken place in five separate West African countries, but has its origins in the defendant's West African oil trading desk in London. It was endemic among the traders in that particular office," he added.
Glencore, founded in 1974, is one of the world's largest multinational commodity trading and mining companies.
Its subsidiaries operate in over 35 countries, but Glencore's London office was primarily concerned with oil, with one of its crude oil divisions responsible for West Africa.
On Wednesday, the Serious Fraud Office told Southwark Crown Court that Glencore Energy UK had paid - or failed to prevent the payment of - millions of dollars in bribes to officials in five African countries.
The bribery charges stated that the company's objective was for officials to "improperly perform their duties, or reward them for doing so, by unduly favouring Glencore Energy UK in the allocation of crude oil cargoes, crude oil withdrawal dates and grades of crude oil allocated".
In 2018, the US Department of Justice (DoJ) launched an investigation into Glencore's compliance with US money laundering and corruption laws dating back to 2007. It concerned the mining giant's operations in Nigeria, the Democratic Republic of Congo and Venezuela.
The UK SFO followed suit in 2019, investigating one of Glencore's UK subsidiaries for "suspected corruption" in Africa.
The Serious Fraud Office has previously stated that its investigation revealed 'bribery and corruption for profit'.
Clare Montgomery, representing Glencore, said: "The company fully regrets the harm caused by these offences and recognises the harm caused, both domestically and publicly in the African states concerned, as well as the harm caused to others.
Justice Fraser stated in his sentencing remarks that Glencore "has engaged in corporate reform and now appears to be a very different company from what it was at the time of these offences".
Lisa Osofsky, director of the Serious Fraud Office, said the case was the first time since the introduction of the Bribery Act 2010 "that a company has been convicted for actively enabling bribery, rather than simply failing to prevent it".
"For years and across the globe, Glencore has sought profits at the expense of national governments in some of the world's poorest countries. The company's ruthless greed and criminality have been rightly exposed," she added.
In May, the company agreed to a $1.1 billion (£900 million) settlement in the US over a scheme to bribe officials in seven countries over a decade.
It concerned the mining giant's operations in Nigeria, the Democratic Republic of Congo and Venezuela.