$re = '/([\s\S]+)((from:(?:(?!from:)[\s\S])+?sent:(?:(?!sent:)[\s\S])+?to:(?:(?!to:)[\s\S])+?subject:(?:(?!subject:)[\s\S])+))/miU';
$str = 'Hello World from: the other side of the first email
from: this
sent: at
to: that
subject: what
second email
from: this
sent: at
to: that
subject: what
third email
from: this
date: at
to: that
subject: what
fourth email';
preg_match($re, $str, $matches, PREG_OFFSET_CAPTURE, 0);
// Print the entire match result
var_dump($matches);
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 PHP, please visit: http://php.net/manual/en/ref.pcre.php