The Securities and Exchange Commission crossed a new threshold this week by securing financial penalties against individual city officials in a municipal bond fraud case.

Four former San Diego officials agreed to pay the financial penalties to settle SEC charges accusing them of misleading municipal bond investors about the city’s fiscal problems.

“These former San Diego officials are paying a price for their actions that jeopardized the interests of investors and put the city’s current and future retirees at risk,” Rosalind Tyson, director of the SEC’s Los Angeles regional office, said in a statement Monday.

The four individuals are former city manager Michael Uberuaga, former city auditor and comptroller Edward Ryan, former deputy city manager of finance Patricia Frazier, and former city treasurer Mary Vattimo.

Uberuaga, Ryan, and Frazier each agreed to pay $25,000 in civil penalties and Vattimo agreed to a $5,000 penalty. The SEC’s charges against a fifth city official, Teresa Webster, a former assistant auditor and comptroller, are still pending.

The commission originally charged that the former officials intentionally misled investors.

The four individuals agreed to settle by accepting the civil penalties. They did not admit or deny the SEC’s allegations, but are enjoined from further violations of the securities laws.

It is the first time the commission secured financial penalties against individual city officials in a municipal bond fraud case, according to the SEC.

“This is a watershed,” said Robert Doty, president of financial advisory firm American Governmental Financial Services and author of “From Turmoil to Tomorrow,” a book about the impact of the financial crisis on the municipal securities market.

“I predict that the significance of this is going to be very far-reaching,” Doty said. “Every municipal official is going to be held responsible. They can’t rely on their bond counsel to do this for them. They can’t rely on their underwriter. They can’t rely on their financial adviser.”

Doty said that it was instructive that the consent agreements bar the individuals from seeking any form of reimbursement, ruling out compensation from employers or insurance, for example.

“The message here, the really clear message, is that the SEC is very, very serious,” he said. “And issuers need to figure out and issuer officials need to figure out how to protect themselves.”

The SEC filed the charges against the five city officials in April 2008, alleging that they knew San Diego had been intentionally underfunding its pension obligations to increase benefits while deferring the costs, and that they were aware that the city would face severe difficulty funding its future retirement obligations without new revenues or cuts to employee benefits or city services.

“Despite this extensive knowledge, they failed to inform municipal investors about the severe funding problems in 2002 and 2003 bond disclosure documents,” the SEC’s statement said.

U.S. District Judge Dana Sabraw must still sign off on the settlements,

The SEC sanctioned the San Diego government in 2006.

The city settled the action by agreeing to cease and desist from future securities fraud violations and to retain an independent consultant for three years to foster compliance with its disclosure ­obligations.

In 2005, the local district attorney brought state felony conflict of interest charges against six city officials involved in the pension agreements. Those charged included Vattimo and Webster.

The district attorney dropped the cases against the six this May, after the California Supreme Court reversed trial and appellate court determinations that there was enough evidence against them to warrant a trial.