re = /([0-9]+)\s+(\w+)\s+(\w+).*?\r?\n•\s+(.*?)\s+[0-9]+\s\|.*\s*/
str = '1 el art the
• esa mujer era la mujer que yo quería ser
100 | 2037803
2 de prep of, from
• el hijo de un hermano mío
100 | 1319834
3 que conj that, which
• dice que no
100 | 662653'
subst = '\\1\\t\\2\\t\\3\\t\\4\\t\\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