<?php
$re = '~(?:<figcaption|(?!^)\G)[^<#]*(?:(?:<(?!\/figcaption>)|#\B)[^<#]*)*\K#\w+~';
$str = "<figcaption>blah # blah #hashtag1, #hashtag2</figcaption> #ee <figcaption>#ddddd";
$subst = "<span class=\"highlight\">$0</span>";
echo $result;
PD9waHAKCiRyZSA9ICd+KD86PGZpZ2NhcHRpb258KD8hXilcRylbXjwjXSooPzooPzo8KD8hXC9maWdjYXB0aW9uPil8I1xCKVtePCNdKikqXEsjXHcrfic7IAokc3RyID0gIjxmaWdjYXB0aW9uPmJsYWggIyBibGFoICNoYXNodGFnMSwgI2hhc2h0YWcyPC9maWdjYXB0aW9uPiAjZWUgPGZpZ2NhcHRpb24+I2RkZGRkIjsgCiRzdWJzdCA9ICI8c3BhbiBjbGFzcz1cImhpZ2hsaWdodFwiPiQwPC9zcGFuPiI7IAokcmVzdWx0ID0gcHJlZ19yZXBsYWNlKCRyZSwgJHN1YnN0LCAkc3RyKTsKZWNobyAkcmVzdWx0Ow==