<?php
$html = <<< EOF
<a href="www.site.com/document.pdf"><img src="../images/image.jpg" /></a>
<img src="../images/image1.jpg" />
<a href="www.site.com/document.txt"><IMG src="../images/image2.jpg" /></a>
<a href="www.site.com/document.doc"><img src="../images/image3.jpg" /></a>
<a href="www.site.com/document1.pdf">My PDF</a>
EOF;
$doc = new DOMDocument();
libxml_use_internal_errors(true);
$doc->loadHTML($html); // loads your html
$nodeList = $doc->getElementsByTagName('a');
for($i=0; $i < $nodeList->length; $i++) {
    $node = $nodeList->item($i);
    $children = $node->childNodes; 
    $hasImage = false;
    foreach ($children as $child) { 
       if ($child->nodeName == 'img') {
          $hasImage = true;
          break;
       }
    }
    if (!$hasImage)
       continue;
    if ($node->hasAttributes())
       foreach ($node->attributes as $attr) {
          $name = $attr->nodeName;
          $value = $attr->nodeValue;
          if ( $attr->nodeName == 'href' && preg_match('/\.(doc|pdf)$/i', $attr->nodeValue) )
             echo $attr->nodeValue . " - Image is wrapped in a link to a PDF or DOC file\n";
       }
}	
?>