re = /(^(?:(?:§.*|[^[:alpha:]\n\r]*[[:upper:]]+(?:[^[:alpha:]\n\r]+[[:upper:]]+)*[^[:alpha:]\n\r]*))$|(?i:\bmany of\b))|(?i:\bof\b)/m
str = '§History of TIME
HISTORY OF TIME
of
Future
Past
Of
Many Of
Official
Officer'
subst = '$1'
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