re = /(me)(?!([^<]+)?>)/i
str = 'I have ever been prone to seek adventure and to investigate and experiment where <span class=\'me\'>wiser men</span> would have left well enough alone.'
subst = '<span class=\'highlight\'>$1</span>'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html