re = /[^[:graph:]*](?#Do not match on any visible character)
\K\*(?#Reset starting point and then match on a *)
([[:alpha:].,\ ]+(?:\*{2}[[:alpha:].,\ ]+\*{2}?\ ?)?)(*COMMIT)
\*\ ?(?#Match on ending * then stop matching with COMMIT)/xm
str = 'This text is not italic.
*This text is italic.*
This text is *partially* italic
This text has *two* *italic* bits
**bold text (not italic)**
**bold text with *italic* **
**part bold,** *part italic*
*italic text **with bold** *
*italic* **bold** *italic* **bold**
*invalid markdown (do not parse)**
random * asterisk'
subst = '<i>$1</i> '
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