re = /(?s)\b(X\d{2})(?:(?!X\d{2}).)*["\s]([^"\s]+\.dun)+|(?:(?!X\d{2}).)*/
str = 'X12
Source =asdjkasjd
file="x/y1.dun"
"x/y2.dun"
"x/y3.dun"
asds12
X22
p/q/xy.dun
asda=23
source =asdf
X44
1000
1001
file="abc.dun"'
subst = '$1\\t\\t$2\\n'
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