Oh there's plenty of companies that have lost more than 100% of their value. If you go from a positive value to a negative value (e.g. you have outstanding liabilities that cannot be discharged), that's a >100% reduction in value.

One good example would be old mining companies that went bankrupt. Their value cratered to zero, AND now the corporate overlords that ended up acquiring them are spending neverending millions of dollars spent to clean up Superfund sites decade after decade. There are some liabilities that simply cannot be discharged.