re = /(?<!\d|^)(?<!(?<![^\W_])(?:sha|md))(?=\d)|(?<=\d)(?!\d|$)|_/m
str = 'Aisha256
ai_sha256
test123
84test
test md5
sha256
word two sha1
w0rd
test_md5
sha256
md5'
subst = ' '
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