If the following org file is exported as HTML, any *strong* markup for words at the beginning or the end of the input string are ignored.  (I have included several slight variations to help testing.)

#+TITLE: Test MACRO with *strong* Markup Input
#+OPTIONS: date:nil timestamp:nil num:nil stat:t title:t toc:nil
#+MACRO: quote @@html:<span class="quote">&ldquo;@@$1@@html:&rdquo;</span>@@

* Test macro with non-marked text:
Demonstrating that, {{{quote(This is a vanilla quote without markup)}}}, Abraham Lincoln.

{{{quote(This is a similar control quote without markup)}}}, George Washington said.

* Test macro with leading *strongly* marked text:
Wilson quipped, {{{quote(*Not all* quotes are important!)}}}.

{{{quote(*But this* is a very important quote)}}}, Thomas Jefferson replied.

* Test macro with trailing *strongly* marked text:
Retorted Yoda, {{{quote(Critical if not uncertain\, all *my quotes are*)}}}.

{{{quote(I am certain they are *all uncertain*)}}}, Anakin sneered.

* Test macro with leading, middle, and trailing marked text:
Darth Vader threatened, {{{quote(*All* of *my quotes* are *heeded carefully!*)}}}.

{{{quote(*Nobody* listens to *meesa* quotes. *Why?*)}}}, Jar-Jar whined.

The condensed filtered HTML output is:

...
<h2 id="org40a1103">Test macro with non-marked text:</h2>
<p>Demonstrating that, <span class="quote">&ldquo;This is a vanilla quote without markup&rdquo;</span>, Abraham Lincoln.</p>
<p><span class="quote">&ldquo;This is a similar control quote without markup&rdquo;</span>, George Washington said.</p>

<h2 id="org962a914">Test macro with leading <b>strongly</b> marked text:</h2>
<p>Wilson quipped, <span class="quote">&ldquo;*Not all* quotes are important!&rdquo;</span>.</p>
<p><span class="quote">&ldquo;*But this* is a very important quote&rdquo;</span>, Thomas Jefferson replied.</p>

<h2 id="org47bf84f">Test macro with trailing <b>strongly</b> marked text:</h2>
<p>Retorted Yoda, <span class="quote">&ldquo;Critical if not uncertain, all *my quotes are*&rdquo;</span>.</p>
<p><span class="quote">&ldquo;I am certain they are *all uncertain*&rdquo;</span>, Anakin sneered.</p>

<h2 id="org08c1694">Test macro with leading, middle, and trailing marked text:</h2>
<p>Darth Vader threatened, <span class="quote">&ldquo;*All* of <b>my quotes</b> are *heeded carefully!*&rdquo;</span>.</p>
<p><span class="quote">&ldquo;*Nobody* listens to <b>meesa</b> quotes. *Why?*&rdquo;</span>, Jar-Jar whined.</p>
...

Notice how the *strong* marks are only transformed into <b></b> tags inside a string, not at the boundaries.

Can anybody confirm or explain what I am doing wrong?

Thanks!

Trevor