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Janus Capital Group had its biggest monthly mutual-fund withdrawals in more than three years after a large client pulled money from the money-manager’s oldest fund.

Investors pulled a net $2.2 billion from the company’s long-term funds in July, the most since May 2010, according to research firm Morningstar.

A single client redeemed $1.3 billion from the now $7 billion Janus Fund in July, said John Groneman, head of investor relations at Denver-based Janus.

“The redemptions are a function of the underperformance the fund has experienced over the last three years,” Groneman said.

Janus, with more than 80 percent of its assets in actively managed equity products, has struggled to retain clients over the past four years as investors flooded into bonds and index-based products. The company last month reported its 16th straight quarter of net investor withdrawals for the three months ended June 30. The Janus Fund, started in 1970, has trailed 87 percent of competing funds over the past three years, according to data compiled by Bloomberg.

Investors removed money from Janus even as they deposited $15.9 billion with long-term U.S.-registered mutual funds in July, according to Morningstar.