re = /<a(.*?)><img(.*?)(\/)?><\/a>/i
str = '<h4>Bild mit Verlinkung und ohne Caption</h4>
<p><a title="" data-original-title="" href="/site/assets/files/1807/bora_bora_3.jpg"><img alt="Rochen" class="align_left" src="/site/assets/files/1807/bora_bora_3.150x0-is.jpg" width="150"></a>Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam nonumy eirmod tempor invidunt ut labore et dolore magna aliquyam erat, sed diam voluptua. At vero eos et accusam et justo duo dolores et ea rebum. Stet clita kasd gubergren, no sea takimata sanctus est Lorem ipsum dolor sit amet. Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam nonumy eirmod tempor invidunt ut labore et dolore magna aliquyam erat, sed diam voluptua. At vero eos et accusam et justo duo dolores et ea rebum. Stet clita kasd gubergren, no sea takimata sanctus est Lorem ipsum dolor sit amet.</p>
<h4>Bild mit Verlinkung und mit Caption</h4>
<figure class="align_left"><a title="" data-original-title="" href="/site/assets/files/1807/bora_bora_3.jpg"><img alt="Rochen" src="/site/assets/files/1807/bora_bora_3.132x0-is.jpg" width="132"></a>
<figcaption>Rochen</figcaption></figure><p>Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam nonumy eirmod tempor invidunt ut labore et dolore magna aliquyam erat, sed diam voluptua. At vero eos et accusam et justo duo dolores et ea rebum. Stet clita kasd gubergren, no sea takimata sanctus est Lorem ipsum dolor sit amet. Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam nonumy eirmod tempor invidunt ut labore et dolore magna aliquyam erat, sed diam voluptua. At vero eos et accusam et justo duo dolores et ea rebum. Stet clita kasd gubergren, no sea takimata sanctus est Lorem ipsum dolor sit amet.</p>'
subst = '<a$1 class="thumbnail"><div class="scalecontainer"><span class="roll"></span><img$1></div></a>'
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