<?xml version="1.0" encoding="UTF-8"?><!DOCTYPE article  PUBLIC "-//NLM//DTD Journal Publishing DTD v3.0 20080202//EN" "http://dtd.nlm.nih.gov/publishing/3.0/journalpublishing3.dtd"><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" dtd-version="3.0" xml:lang="en" article-type="research article"><front><journal-meta><journal-id journal-id-type="publisher-id">IJAMSC</journal-id><journal-title-group><journal-title>International Journal of Analytical Mass Spectrometry and Chromatography</journal-title></journal-title-group><issn pub-type="epub">2332-1768</issn><publisher><publisher-name>Scientific Research Publishing</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="doi">10.4236/ijamsc.2018.62003</article-id><article-id pub-id-type="publisher-id">IJAMSC-85152</article-id><article-categories><subj-group subj-group-type="heading"><subject>Short Communications</subject></subj-group><subj-group subj-group-type="Discipline-v2"><subject>Chemistry&amp;Materials Science</subject></subj-group></article-categories><title-group><article-title>
 
 
  Super Antibiotics, Part VI: Hyperforin, Revision of Stereochemistry. Short Communications
 
</article-title></title-group><contrib-group><contrib contrib-type="author" xlink:type="simple"><name name-style="western"><surname>Ilia</surname><given-names>Brondz</given-names></name><xref ref-type="aff" rid="aff1"><sub>1</sub></xref><xref ref-type="corresp" rid="cor1"><sup>*</sup></xref></contrib></contrib-group><aff id="aff1"><label>1</label><addr-line>Norwegian Drug Control and Drug Discovery Institute (NDCDDI), Ski, Norway</addr-line></aff><author-notes><corresp id="cor1">* E-mail:<email>ilia.brondz@gmail.com</email></corresp></author-notes><pub-date pub-type="epub"><day>04</day><month>06</month><year>2018</year></pub-date><volume>06</volume><issue>02</issue><fpage>37</fpage><lpage>39</lpage><history><date date-type="received"><day>22,</day>	<month>March</month>	<year>2018</year></date><date date-type="rev-recd"><day>5,</day>	<month>June</month>	<year>2018</year>	</date><date date-type="accepted"><day>8,</day>	<month>June</month>	<year>2018</year></date></history><permissions><copyright-statement>&#169; Copyright  2014 by authors and Scientific Research Publishing Inc. </copyright-statement><copyright-year>2014</copyright-year><license><license-p>This work is licensed under the Creative Commons Attribution International License (CC BY). http://creativecommons.org/licenses/by/4.0/</license-p></license></permissions><abstract><p>
 
 
  This short communication is an overview and revision of previous published papers about the relative and absolute stereochemistry of hyperforin and discovery of a new isomer of hyperforin that has been named perforatrin.
 
</p></abstract><kwd-group><kwd>Revision</kwd><kwd> Relative and Absolute Stereochemistry</kwd><kwd> Hyperforin</kwd><kwd> Perforatrin</kwd></kwd-group></article-meta></front><body><sec id="s1"><title>1. Introduction</title><p>The antibiotic properties of the antibacterial substances known to be present in species of the genus Hypericum (Hypericaceae (Guttiferae)), is well established. Extracts from the plant Hypericum perforatum L. have been used to preserve food [<xref ref-type="bibr" rid="scirp.85152-ref1">1</xref>] , treat infections [<xref ref-type="bibr" rid="scirp.85152-ref2">2</xref>] , as immunomodulating agent [<xref ref-type="bibr" rid="scirp.85152-ref3">3</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref4">4</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref5">5</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref6">6</xref>] and for many other medical purposes. One active constituent designated hyperforin, was isolated and characterized in 1971 [<xref ref-type="bibr" rid="scirp.85152-ref7">7</xref>] . The absolute configuration was suggested in 1975-1976 [<xref ref-type="bibr" rid="scirp.85152-ref8">8</xref>] . The report [<xref ref-type="bibr" rid="scirp.85152-ref9">9</xref>] presents arguments suggesting that a crystal structures determination of the 3.5-dinitrobenzoate ester [<xref ref-type="bibr" rid="scirp.85152-ref10">10</xref>] and p-bromobenzoate ester [<xref ref-type="bibr" rid="scirp.85152-ref11">11</xref>] are in contradiction with the proposed absolute configuration published in [<xref ref-type="bibr" rid="scirp.85152-ref8">8</xref>] . In order to obtain direct evidence for the absolute stereochemistry of hyperforin, a single crystal structure analysis of its p-bromobenzoate ester has been carried out [<xref ref-type="bibr" rid="scirp.85152-ref11">11</xref>] and has been supported by GC-MS [<xref ref-type="bibr" rid="scirp.85152-ref9">9</xref>] . In accordance to X-ray crystallography [<xref ref-type="bibr" rid="scirp.85152-ref11">11</xref>] , it may be pointed out that the difference between the earlier suggested absolute configuration by Bystrov et al. [<xref ref-type="bibr" rid="scirp.85152-ref7">7</xref>] and absolute configuration [<xref ref-type="bibr" rid="scirp.85152-ref8">8</xref>] suggested also by Bystrov et al. in 1975-1976, the absolute configuration resolved by X-ray crystallography and presented by Brondz et al. in [<xref ref-type="bibr" rid="scirp.85152-ref11">11</xref>] , is that stereochemistry at the two chiral centers is different. The same is supported by [<xref ref-type="bibr" rid="scirp.85152-ref10">10</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref11">11</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref12">12</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref13">13</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref14">14</xref>] .</p><p>First time MS spectrum of hyperforin has been obtained by using chemical ionization (CI) [<xref ref-type="bibr" rid="scirp.85152-ref1">1</xref>] (<xref ref-type="fig" rid="fig1">Figure 1</xref>).</p><p>In following publication [<xref ref-type="bibr" rid="scirp.85152-ref9">9</xref>] has been discovered two isomers of hyperforin, the major is hyperforin and the minor was named perforatrin (<xref ref-type="fig" rid="fig2">Figure 2</xref>).</p><p>The stereochemistry proposed by Bystrov et al. in [<xref ref-type="bibr" rid="scirp.85152-ref7">7</xref>] and [<xref ref-type="bibr" rid="scirp.85152-ref8">8</xref>] was wrong, comparison of absolute configuration of hyperforin has been proposed by Brondz et al. [<xref ref-type="bibr" rid="scirp.85152-ref11">11</xref>] and supported by Brondz [<xref ref-type="bibr" rid="scirp.85152-ref9">9</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref12">12</xref>] . In independent research [<xref ref-type="bibr" rid="scirp.85152-ref13">13</xref>] and [<xref ref-type="bibr" rid="scirp.85152-ref14">14</xref>] conclusively has been demonstrated correctness of stereochemistry of hyperforin proposed by Brondz in [<xref ref-type="bibr" rid="scirp.85152-ref9">9</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref10">10</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref11">11</xref>] [<xref ref-type="bibr" rid="scirp.85152-ref12">12</xref>] .</p></sec><sec id="s2"><title>Acknowledgements</title><p><xref ref-type="fig" rid="fig1">Figure 1</xref> and <xref ref-type="fig" rid="fig2">Figure 2</xref> was republished from publication [<xref ref-type="bibr" rid="scirp.85152-ref9">9</xref>] .</p></sec><sec id="s3"><title>Cite this paper</title><p>Brondz, I. (2018) Super Antibiotics, Part VI: Hyperforin, Revision of Stereochemistry. Short Communications. International Journal of Analytical Mass Spectrometry and Chromatography, 6, 37-39. https://doi.org/10.4236/ijamsc.2018.62003</p></sec></body><back><ref-list><title>References</title><ref id="scirp.85152-ref1"><label>1</label><mixed-citation publication-type="other" xlink:type="simple">Brondz, I. (1979) Antibiotikumet “Hyperforin” og andre innholdsstoffer i drogen Hypricum perforatum L. Thesis (Cand. Pharm.). University of Oslo, Oslo. (In Norwegian)</mixed-citation></ref><ref id="scirp.85152-ref2"><label>2</label><mixed-citation publication-type="other" xlink:type="simple">Gurevich, A.I., Dobrynin, V.N., Kolosov, M.N., Popravko, S.A., Ryabova, I.D., Chernov, B.K., Derbentseva, N.A., Aizenman, B.E. and Garagulya, A.D. (1971) Hyperforin, an Antibiotic from Hypericum perforatum L. 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