re = /<span(?=\s)(?=(?:[^>"']|"[^"]*"|'[^']*')*?\sstyle\s*=\s*(?:(['"])(?:(?!\1)[\S\s])*?font-weight:700(?:(?!\1)[\S\s])*\1))\s+(?:"[\S\s]*?"|'[\S\s]*?'|[^>]*?)+>([\S\s]*?)<\/span\s*>/
str = '<p><span style="color:#2c2c2c;font-weight:700;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">Strong content</span></p><ul><li><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">list item</span></li><li><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">list item</span></li><li><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">list item</span></li><li><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">list item</span></li><li><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">list item</span></li><li><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">list item</span></li></ul><p><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">Content text</span></p><p><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">Content text</span></p><p><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">Content text</span></p><p><span style="font-size:10.5pt;color:#2c2c2c;font-weight:700">Should be bold</span><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">: regular text</span></p><p><span style="font-size:10.5pt;color:#2c2c2c;font-weight:700">Should be bold</span><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">: regular text </span></p><p><span style="font-size:10.5pt;color:#2c2c2c;font-weight:700">Should be bold</span><span style="color:#2c2c2c;font-weight:400;text-decoration:none;vertical-align:baseline;font-size:10.5pt;font-family:"Arial";font-style:normal">: regular text</span></p>'
subst = '<strong>$2</strong>'
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