I think you would need a parser. So this stylesheet implements a verbose one:
<xsl:stylesheet version="1.0" xmlns:xsl="http://www.w3.org/1999/XSL/Transform">
<xsl:template match="text" name="block">
<xsl:param name="pString" select="."/>
<xsl:if test="$pString != ''">
<xsl:choose>
<xsl:when test="starts-with($pString,'#')">
<xsl:call-template name="header">
<xsl:with-param name="pString"
select="substring($pString,2)"/>
</xsl:call-template>
</xsl:when>
<xsl:when test="starts-with($pString,'
')">
<xsl:call-template name="list">
<xsl:with-param name="pString"
select="substring($pString,2)"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:call-template name="paragraph">
<xsl:with-param name="pString"
select="$pString"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:if>
</xsl:template>
<xsl:template name="header">
<xsl:param name="pString"/>
<xsl:variable name="vInside"
select="substring-before($pString,'#
')"/>
<xsl:choose>
<xsl:when test="$vInside != ''">
<h1>
<xsl:call-template name="inline">
<xsl:with-param name="pString" select="$vInside"/>
</xsl:call-template>
</h1>
<xsl:call-template name="block">
<xsl:with-param name="pString"
select="substring-after($pString,'#
')"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:call-template name="paragraph">
<xsl:with-param name="pString"
select="concat('#',$pString)"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:template>
<xsl:template name="list">
<xsl:param name="pString"/>
<xsl:variable name="vCheckList" select="starts-with($pString,'- ')"/>
<xsl:choose>
<xsl:when test="$vCheckList">
<ul>
<xsl:call-template name="listItem">
<xsl:with-param name="pString" select="$pString"/>
</xsl:call-template>
</ul>
<xsl:call-template name="block">
<xsl:with-param name="pString">
<xsl:call-template name="afterlist">
<xsl:with-param name="pString" select="$pString"/>
</xsl:call-template>
</xsl:with-param>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:call-template name="block">
<xsl:with-param name="pString" select="$pString"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:template>
<xsl:template name="paragraph">
<xsl:param name="pString"/>
<xsl:choose>
<xsl:when test="contains($pString,'
')">
<p>
<xsl:value-of select="substring-before($pString,'
')"/>
</p>
</xsl:when>
<xsl:otherwise>
<p>
<xsl:value-of select="$pString"/>
</p>
</xsl:otherwise>
</xsl:choose>
<xsl:call-template name="block">
<xsl:with-param name="pString"
select="substring-after($pString,'
')"/>
</xsl:call-template>
</xsl:template>
<xsl:template name="afterlist">
<xsl:param name="pString"/>
<xsl:choose>
<xsl:when test="starts-with($pString,'- ')">
<xsl:call-template name="afterlist">
<xsl:with-param name="pString"
select="substring-after($pString,'
')"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:value-of select="$pString"/>
</xsl:otherwise>
</xsl:choose>
</xsl:template>
<xsl:template name="listItem">
<xsl:param name="pString"/>
<xsl:if test="starts-with($pString,'- ')">
<li>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="substring-before(substring($pString,3),'
')"/>
</xsl:call-template>
</li>
<xsl:call-template name="listItem">
<xsl:with-param name="pString"
select="substring-after($pString,'
')"/>
</xsl:call-template>
</xsl:if>
</xsl:template>
<xsl:template name="inline">
<xsl:param name="pString" select="."/>
<xsl:if test="$pString != ''">
<xsl:choose>
<xsl:when test="starts-with($pString,'__')">
<xsl:call-template name="strong">
<xsl:with-param name="pString"
select="substring($pString,3)"/>
</xsl:call-template>
</xsl:when>
<xsl:when test="starts-with($pString,'*')">
<xsl:call-template name="span">
<xsl:with-param name="pString"
select="substring($pString,2)"/>
</xsl:call-template>
</xsl:when>
<xsl:when test="starts-with($pString,'"')">
<xsl:call-template name="link">
<xsl:with-param name="pString"
select="substring($pString,2)"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:value-of select="substring($pString,1,1)"/>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="substring($pString,2)"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:if>
</xsl:template>
<xsl:template name="strong">
<xsl:param name="pString"/>
<xsl:variable name="vInside" select="substring-before($pString,'__')"/>
<xsl:choose>
<xsl:when test="$vInside != ''">
<strong>
<xsl:value-of select="$vInside"/>
</strong>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="substring-after($pString,'__')"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:value-of select="'__'"/>
<xsl:call-template name="inline">
<xsl:with-param name="pString" select="$pString"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:template>
<xsl:template name="span">
<xsl:param name="pString"/>
<xsl:variable name="vInside" select="substring-before($pString,'*')"/>
<xsl:choose>
<xsl:when test="$vInside != ''">
<span>
<xsl:value-of select="$vInside"/>
</span>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="substring-after($pString,'*')"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:value-of select="'*'"/>
<xsl:call-template name="inline">
<xsl:with-param name="pString" select="$pString"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:template>
<xsl:template name="link">
<xsl:param name="pString"/>
<xsl:variable name="vInside"
select="substring-before($pString,'"')"/>
<xsl:choose>
<xsl:when test="$vInside != ''">
<xsl:call-template name="href">
<xsl:with-param name="pString"
select="substring-after($pString,'"')"/>
<xsl:with-param name="pInside" select="$vInside"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:value-of select="'"'"/>
<xsl:call-template name="inline">
<xsl:with-param name="pString" select="$pString"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:template>
<xsl:template name="href">
<xsl:param name="pString"/>
<xsl:param name="pInside"/>
<xsl:variable name="vHref"
select="substring-before(substring($pString,2),']')"/>
<xsl:choose>
<xsl:when test="starts-with($pString,'[') and $vHref != ''">
<a href="{$vHref}">
<xsl:value-of select="$pInside"/>
</a>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="substring-after($pString,']')"/>
</xsl:call-template>
</xsl:when>
<xsl:otherwise>
<xsl:value-of select="concat('"',$pInside,'"')"/>
<xsl:call-template name="inline">
<xsl:with-param name="pString" select="$pString"/>
</xsl:call-template>
</xsl:otherwise>
</xsl:choose>
</xsl:template>
</xsl:stylesheet>
With this input:
<text>
# This is a title with __bold__ text and *italic* #
This is just a normal line
- list point with some __bold__
- list point with a "link"[http://www.stackoverflow.com]
</text>
Output:
<h1> This is a title with
<strong>bold</strong> text and
<span>italic</span>
</h1>
<p>This is just a normal line</p>
<ul>
<li>list point with some
<strong>bold</strong>
</li>
<li>list point with a
<a href="http://www.stackoverflow.com">link</a>
</li>
</ul>
Note: Look how many templates are simitar (they follow a pattern), so these could be parameterized. I didn't do that in this case because there seems to be more questions wich need some sort of parser, so by the end of the week I will repost an answer implementing fuctional parser and parser combinators pattern that make very easy to write parsers (just writing its grammar rules).
Edit: XSLT 2.0 solution. This stylesheet:
<xsl:stylesheet version="2.0" xmlns:xsl="http://www.w3.org/1999/XSL/Transform">
<xsl:template match="text">
<xsl:param name="pString" select="."/>
<xsl:analyze-string select="$pString"
regex="(#(.*)#
)|((- (.*)
)+)">
<xsl:matching-substring>
<xsl:choose>
<xsl:when test="regex-group(1)">
<h1>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="regex-group(2)"/>
</xsl:call-template>
</h1>
</xsl:when>
<xsl:when test="regex-group(3)">
<ul>
<xsl:call-template name="list">
<xsl:with-param name="pString"
select="regex-group(3)"/>
</xsl:call-template>
</ul>
</xsl:when>
</xsl:choose>
</xsl:matching-substring>
<xsl:non-matching-substring>
<xsl:if test=".!='
'">
<p>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="normalize-space(.)"/>
</xsl:call-template>
</p>
</xsl:if>
</xsl:non-matching-substring>
</xsl:analyze-string>
</xsl:template>
<xsl:template name="list">
<xsl:param name="pString"/>
<xsl:analyze-string select="$pString" regex="- (.*)
">
<xsl:matching-substring>
<li>
<xsl:call-template name="inline">
<xsl:with-param name="pString"
select="regex-group(1)"/>
</xsl:call-template>
</li>
</xsl:matching-substring>
</xsl:analyze-string>
</xsl:template>
<xsl:template name="inline">
<xsl:param name="pString" select="."/>
<xsl:analyze-string select="$pString"
regex="(__(.*)__)|(\*(.*)\*)|("(.*)"\[(.*)\])">
<xsl:matching-substring>
<xsl:choose>
<xsl:when test="regex-group(1)">
<strong>
<xsl:value-of select="regex-group(2)"/>
</strong>
</xsl:when>
<xsl:when test="regex-group(3)">
<span>
<xsl:value-of select="regex-group(4)"/>
</span>
</xsl:when>
<xsl:when test="regex-group(5)">
<a href="{regex-group(7)}">
<xsl:value-of select="regex-group(6)"/>
</a>
</xsl:when>
</xsl:choose>
</xsl:matching-substring>
<xsl:non-matching-substring>
<xsl:value-of select="."/>
</xsl:non-matching-substring>
</xsl:analyze-string>
</xsl:template>
</xsl:stylesheet>
Output:
<h1> This is a title with
<strong>bold</strong> text and
<span>italic</span>
</h1>
<p>This is just a normal line</p>
<ul>
<li>list point with some
<strong>bold</strong>
</li>
<li>list point with a
<a href="http://www.stackoverflow.com">link</a>
</li>
</ul>