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mw-first-heading"><i>Vinca</i> alkaloid</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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mw-list-item"><a href="https://de.wikipedia.org/wiki/Vincaalkaloide" title="Vincaalkaloide – German" lang="de" hreflang="de" data-title="Vincaalkaloide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Alcaloides_de_la_vinca" title="Alcaloides de la vinca – Spanish" lang="es" hreflang="es" data-title="Alcaloides de la vinca" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Vinca-alcalo%C3%AFde" title="Vinca-alcaloïde – French" lang="fr" hreflang="fr" data-title="Vinca-alcaloïde" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Alkaloid_vinka" title="Alkaloid vinka – Indonesian" lang="id" hreflang="id" data-title="Alkaloid vinka" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Alcaloidi_della_vinca" title="Alcaloidi della vinca – Italian" lang="it" hreflang="it" data-title="Alcaloidi della vinca" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%93%E3%83%B3%E3%82%AB%E3%82%A2%E3%83%AB%E3%82%AB%E3%83%AD%E3%82%A4%E3%83%89" title="ビンカアルカロイド – Japanese" lang="ja" hreflang="ja" data-title="ビンカアルカロイド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alkaloidy_barwinka_r%C3%B3%C5%BCyczkowego" title="Alkaloidy barwinka różyczkowego – Polish" lang="pl" hreflang="pl" data-title="Alkaloidy barwinka różyczkowego" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Alcaloides_da_vinca" title="Alcaloides da vinca – Portuguese" lang="pt" hreflang="pt" data-title="Alcaloides da vinca" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Alkaloid_ro%C5%BEnatega_zimzelena" title="Alkaloid rožnatega zimzelena – Slovenian" lang="sl" hreflang="sl" data-title="Alkaloid rožnatega zimzelena" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%92%D0%B8%D0%BD%D0%BA%D0%B0_%D0%B0%D0%BB%D0%BA%D0%B0%D0%BB%D0%BE%D0%B8%D0%B4" title="Винка алкалоид – Serbian" lang="sr" hreflang="sr" data-title="Винка алкалоид" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Vinka_alkaloid" title="Vinka alkaloid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Vinka alkaloid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Vinka-alkaloidit" title="Vinka-alkaloidit – Finnish" lang="fi" hreflang="fi" data-title="Vinka-alkaloidit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q3559405#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Alkaloid agents from the Cape periwinkle</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Vincristine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Vincristine.svg/220px-Vincristine.svg.png" decoding="async" width="220" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Vincristine.svg/330px-Vincristine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Vincristine.svg/440px-Vincristine.svg.png 2x" data-file-width="1712" data-file-height="1292" /></a><figcaption>Chemical structure of the <i>vinca</i> alkaloid <a href="/wiki/Vincristine" title="Vincristine">vincristine</a></figcaption></figure> <p><b><i>Vinca</i> alkaloids</b> are a set of <a href="/wiki/Antimitotic_agent" class="mw-redirect" title="Antimitotic agent">anti-mitotic</a> and <a href="/wiki/Anti-microtubule_activity" class="mw-redirect" title="Anti-microtubule activity">anti-microtubule</a> <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> agents originally derived from the periwinkle plant <i><a href="/wiki/Catharanthus_roseus" title="Catharanthus roseus">Catharanthus roseus</a></i> (<a href="/wiki/Basionym" title="Basionym">basionym</a> <i>Vinca rosea</i>) and other <i><a href="/wiki/Vinca" title="Vinca">vinca</a></i> plants. They block <a href="/wiki/Beta-tubulin" class="mw-redirect" title="Beta-tubulin">beta-tubulin</a> polymerization in a dividing cell. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinca_alkaloid&action=edit&section=1" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Madagascan periwinkle <i><a href="/wiki/Catharanthus_roseus" title="Catharanthus roseus">Catharanthus roseus</a></i> L. is the source for a number of important natural products,<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> including <a href="/wiki/Catharanthine" title="Catharanthine">catharanthine</a> and <a href="/wiki/Vindoline" title="Vindoline">vindoline</a><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and the vinca alkaloids it produces from them: <a href="/w/index.php?title=Leurosine&action=edit&redlink=1" class="new" title="Leurosine (page does not exist)">leurosine</a> and the <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a> agents <a href="/wiki/Vinblastine" title="Vinblastine">vinblastine</a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Vincristine" title="Vincristine">vincristine</a>,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> all of which can be obtained from the plant.<sup id="cite_ref-TopicsCurrentChem_5-0" class="reference"><a href="#cite_note-TopicsCurrentChem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MoleculesReview_7-0" class="reference"><a href="#cite_note-MoleculesReview-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The newer <a href="/wiki/Semisynthesis" title="Semisynthesis">semi-synthetic</a> chemotherapeutic agent <a href="/wiki/Vinorelbine" title="Vinorelbine">vinorelbine</a> is used in the treatment of <a href="/wiki/Non-small-cell_lung_cancer" title="Non-small-cell lung cancer">non-small-cell lung cancer</a><sup id="cite_ref-MoleculesReview_7-1" class="reference"><a href="#cite_note-MoleculesReview-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and is not known to occur naturally. However, it can be prepared either from vindoline and catharanthine<sup id="cite_ref-MoleculesReview_7-2" class="reference"><a href="#cite_note-MoleculesReview-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-anhydro2vinorelbine_10-0" class="reference"><a href="#cite_note-anhydro2vinorelbine-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> or from leurosine,<sup id="cite_ref-Anhydro_11-0" class="reference"><a href="#cite_note-Anhydro-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> in both cases by synthesis of anhydrovinblastine, which "can be considered as the key intermediate for the synthesis of vinorelbine."<sup id="cite_ref-MoleculesReview_7-3" class="reference"><a href="#cite_note-MoleculesReview-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The leurosine pathway uses the <a href="/wiki/Nugent%E2%80%93RajanBabu_reagent" class="mw-redirect" title="Nugent–RajanBabu reagent">Nugent–RajanBabu reagent</a> in a highly <a href="/wiki/Chemoselective" class="mw-redirect" title="Chemoselective">chemoselective</a> de-oxygenation of leurosine.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Anhydro_11-1" class="reference"><a href="#cite_note-Anhydro-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Anhydrovinblastine is then reacted sequentially with <a href="/wiki/N-bromosuccinimide" class="mw-redirect" title="N-bromosuccinimide"><i>N</i>-bromosuccinimide</a> and <a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">trifluoroacetic acid</a> followed by <a href="/wiki/Silver_tetrafluoroborate" title="Silver tetrafluoroborate">silver tetrafluoroborate</a> to yield vinorelbine.<sup id="cite_ref-anhydro2vinorelbine_10-1" class="reference"><a href="#cite_note-anhydro2vinorelbine-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Vinorelbine_from_leurosine_and_from_catharanthine_plus_vindoline.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Vinorelbine_from_leurosine_and_from_catharanthine_plus_vindoline.jpg/1000px-Vinorelbine_from_leurosine_and_from_catharanthine_plus_vindoline.jpg" decoding="async" width="1000" height="374" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Vinorelbine_from_leurosine_and_from_catharanthine_plus_vindoline.jpg/1500px-Vinorelbine_from_leurosine_and_from_catharanthine_plus_vindoline.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Vinorelbine_from_leurosine_and_from_catharanthine_plus_vindoline.jpg/2000px-Vinorelbine_from_leurosine_and_from_catharanthine_plus_vindoline.jpg 2x" data-file-width="2254" data-file-height="842" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinca_alkaloid&action=edit&section=2" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Vinca</i> alkaloids are used in <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a> for cancer. They are a class of <a href="/wiki/Cell_cycle" title="Cell cycle">cell cycle</a>–specific <a href="/wiki/List_of_chemotherapeutic_agents" title="List of chemotherapeutic agents">cytotoxic drugs</a> that work by inhibiting the ability of cancer cells to divide: Acting upon tubulin, they prevent it from forming into <a href="/wiki/Microtubules" class="mw-redirect" title="Microtubules">microtubules</a>, a necessary component for <a href="/wiki/Cellular_division" class="mw-redirect" title="Cellular division">cellular division</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The <i>vinca</i> alkaloids thus prevent microtubule <i>polymerization</i>, as opposed to the mechanism of action of <a href="/wiki/Taxane" title="Taxane">taxanes</a>. </p><p><i>Vinca</i> alkaloids are now produced <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthetically</a> and used as drugs in cancer therapy and as immunosuppressive drugs. These compounds include vinblastine, vincristine, <a href="/wiki/Vindesine" title="Vindesine">vindesine</a>, and vinorelbine. Additional researched <i>vinca</i> alkaloids include <a href="/wiki/Vincaminol" title="Vincaminol">vincaminol</a>, <a href="/wiki/Vineridine" title="Vineridine">vineridine</a>, and <a href="/wiki/Vinburnine" title="Vinburnine">vinburnine</a>. </p><p><a href="/wiki/Vinpocetine" title="Vinpocetine">Vinpocetine</a> is a semi-synthetic <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivative</a> of <a href="/wiki/Vincamine" title="Vincamine">vincamine</a> (sometimes described as "a <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthetic</a> <a href="/wiki/Ethyl_ester" class="mw-redirect" title="Ethyl ester">ethyl ester</a> of apovincamine").<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Minor <i>vinca</i> alkaloids include minovincine, methoxyminovincine, minovincinine, vincadifformine, desoxyvincaminol, and vincamajine.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinca_alkaloid&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFvan_der_HeijdenJacobsSnoeijerHallard2004" class="citation journal cs1">van der Heijden, Robert; Jacobs, Denise I.; Snoeijer, Wim; Hallard, Didier; Verpoorte, Robert (2004). "The <i>Catharanthus</i> alkaloids: Pharmacognosy and biotechnology". <i><a href="/wiki/Current_Medicinal_Chemistry" title="Current Medicinal Chemistry">Current Medicinal Chemistry</a></i>. <b>11</b> (5): <span class="nowrap">607–</span>628. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F0929867043455846">10.2174/0929867043455846</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15032608">15032608</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Medicinal+Chemistry&rft.atitle=The+Catharanthus+alkaloids%3A+Pharmacognosy+and+biotechnology&rft.volume=11&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E607-%3C%2Fspan%3E628&rft.date=2004&rft_id=info%3Adoi%2F10.2174%2F0929867043455846&rft_id=info%3Apmid%2F15032608&rft.aulast=van+der+Heijden&rft.aufirst=Robert&rft.au=Jacobs%2C+Denise+I.&rft.au=Snoeijer%2C+Wim&rft.au=Hallard%2C+Didier&rft.au=Verpoorte%2C+Robert&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVinca+alkaloid" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHirataMiyamotoMiura1994" class="citation book cs1">Hirata, K.; Miyamoto, K.; Miura, Y. (1994). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=e64hCDBddowC&pg=PA47">"<i>Catharanthus roseus</i> L. (Periwinkle): Production of Vindoline and Catharanthine in Multiple Shoot Cultures"</a>. In Bajaj, Y. P. S. (ed.). <a rel="nofollow" class="external text" href="https://archive.org/details/medicinalaromati0006unse/page/46"><i>Biotechnology in Agriculture and Forestry 26</i></a>. Medicinal and Aromatic Plants. 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