re = /(<mark[^>]*>.*?<\/mark>)|(( |.)((?:#|#)(?:[a-z0-9_\u00c0-\u00d6\u00d8-\u00f6\u00f8-\u00ff\u0100-\u024f\u0253-\u0254\u0256-\u0257\u{0259}\u{025b}\u{0263}\u{0268}\u{026f}\u{0272}\u{0289}\u{028b}\u{02bb}\u0300-\u036f\u1e00-\u1eff\u0400-\u04ff\u0500-\u0527\u2de0-\u2dff\ua640-\ua69f\u0591-\u05bf\u05c1-\u05c2\u05c4-\u05c5\u{05c7}\u05d0-\u05ea\u05f0-\u05f4\ufb12-\ufb28\ufb2a-\ufb36\ufb38-\ufb3c\u{fb3e}\ufb40-\ufb41\ufb43-\ufb44\ufb46-\ufb4f\u0610-\u061a\u0620-\u065f\u066e-\u06d3\u06d5-\u06dc\u06de-\u06e8\u06ea-\u06ef\u06fa-\u06fc\u{06ff}\u0750-\u077f\u{08a0}\u08a2-\u08ac\u08e4-\u08fe\ufb50-\ufbb1\ufbd3-\ufd3d\ufd50-\ufd8f\ufd92-\ufdc7\ufdf0-\ufdfb\ufe70-\ufe74\ufe76-\ufefc\u200c-\u200c\u0e01-\u0e3a\u0e40-\u0e4e\u1100-\u11ff\u3130-\u3185\ua960-\ua97f\uac00-\ud7af\ud7b0-\ud7ff\uffa1-\uffdc\u30a1-\u30fa\u30fc-\u30fe\uff66-\uff9f\uff10-\uff19\uff21-\uff3a\uff41-\uff5a\u3041-\u3096\u3099-\u309e\u3400-\u4dbf\u4e00-\u9fff\u{3003}\u{3005}\u{303b}]*[a-z_\u00c0-\u00d6\u00d8-\u00f6\u00f8-\u00ff\u0100-\u024f\u0253-\u0254\u0256-\u0257\u{0259}\u{025b}\u{0263}\u{0268}\u{026f}\u{0272}\u{0289}\u{028b}\u{02bb}\u0300-\u036f\u1e00-\u1eff\u0400-\u04ff\u0500-\u0527\u2de0-\u2dff\ua640-\ua69f\u0591-\u05bf\u05c1-\u05c2\u05c4-\u05c5\u{05c7}\u05d0-\u05ea\u05f0-\u05f4\ufb12-\ufb28\ufb2a-\ufb36\ufb38-\ufb3c\u{fb3e}\ufb40-\ufb41\ufb43-\ufb44\ufb46-\ufb4f\u0610-\u061a\u0620-\u065f\u066e-\u06d3\u06d5-\u06dc\u06de-\u06e8\u06ea-\u06ef\u06fa-\u06fc\u{06ff}\u0750-\u077f\u{08a0}\u08a2-\u08ac\u08e4-\u08fe\ufb50-\ufbb1\ufbd3-\ufd3d\ufd50-\ufd8f\ufd92-\ufdc7\ufdf0-\ufdfb\ufe70-\ufe74\ufe76-\ufefc\u200c-\u200c\u0e01-\u0e3a\u0e40-\u0e4e\u1100-\u11ff\u3130-\u3185\ua960-\ua97f\uac00-\ud7af\ud7b0-\ud7ff\uffa1-\uffdc\u30a1-\u30fa\u30fc-\u30fe\uff66-\uff9f\uff10-\uff19\uff21-\uff3a\uff41-\uff5a\u3041-\u3096\u3099-\u309e\u3400-\u4dbf\u4e00-\u9fff\u{3003}\u{3005}\u{303b}][a-z0-9_\u00c0-\u00d6\u00d8-\u00f6\u00f8-\u00ff\u0100-\u024f\u0253-\u0254\u0256-\u0257\u{0259}\u{025b}\u{0263}\u{0268}\u{026f}\u{0272}\u{0289}\u{028b}\u{02bb}\u0300-\u036f\u1e00-\u1eff\u0400-\u04ff\u0500-\u0527\u2de0-\u2dff\ua640-\ua69f\u0591-\u05bf\u05c1-\u05c2\u05c4-\u05c5\u{05c7}\u05d0-\u05ea\u05f0-\u05f4\ufb12-\ufb28\ufb2a-\ufb36\ufb38-\ufb3c\u{fb3e}\ufb40-\ufb41\ufb43-\ufb44\ufb46-\ufb4f\u0610-\u061a\u0620-\u065f\u066e-\u06d3\u06d5-\u06dc\u06de-\u06e8\u06ea-\u06ef\u06fa-\u06fc\u{06ff}\u0750-\u077f\u{08a0}\u08a2-\u08ac\u08e4-\u08fe\ufb50-\ufbb1\ufbd3-\ufd3d\ufd50-\ufd8f\ufd92-\ufdc7\ufdf0-\ufdfb\ufe70-\ufe74\ufe76-\ufefc\u200c-\u200c\u0e01-\u0e3a\u0e40-\u0e4e\u1100-\u11ff\u3130-\u3185\ua960-\ua97f\uac00-\ud7af\ud7b0-\ud7ff\uffa1-\uffdc\u30a1-\u30fa\u30fc-\u30fe\uff66-\uff9f\uff10-\uff19\uff21-\uff3a\uff41-\uff5a\u3041-\u3096\u3099-\u309e\u3400-\u4dbf\u4e00-\u9fff\u{3003}\u{3005}\u{303b}]*)))(( |\W)|$)/i
str = '<p>laboris nisi ut aliquip ex ea commodo</p><p> #adf -sdaf</p><p>dsf w#home</p>
<p>Lorem <mark contenteditable="false">#ipsum</mark> dolor sit amet, </p><p>consectetur adipisicing elit, sed do </p><p>eiusmod</p><p>tempor incididunt ut <mark contenteditable="false">#labore</mark> et </p><p>#dolore </p><p>magna aliqua. Ut enim ad minim </p><p>veniam,</p><p>quis @nostrud exercitation ul <mark contenteditable="false">#lamco</mark> </p>#else'
subst = '$1$3<mark contenteditable=\\"false\\">$4</mark>$5'
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