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Alkaloids from Nerine filifolia
The alkaloids N-demethylbelladine, 6α-methoxybuphanidrine and filifoline are described for the first time from bulbs of Nerine filifolia (Amaryllidaceae). The nicotinate ester in filifoline was observed to reverse molecular ellipticity as expressed in the shape of the CD curve. The novel compounds N...
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| Published in: | Phytochemistry (Oxford) 2005-02, Vol.66 (3), p.373-382 |
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| Main Authors: | , , , , , |
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| Language: | English |
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| container_end_page | 382 |
| container_issue | 3 |
| container_start_page | 373 |
| container_title | Phytochemistry (Oxford) |
| container_volume | 66 |
| creator | Nair, Jerald J. Campbell, William E. Brun, Reto Viladomat, Francesc Codina, Carles Bastida, Jaume |
| description | The alkaloids
N-demethylbelladine, 6α-methoxybuphanidrine and filifoline are described for the first time from bulbs of
Nerine filifolia (Amaryllidaceae). The nicotinate ester in filifoline was observed to reverse molecular ellipticity as expressed in the shape of the CD curve.
The novel compounds
N-demethylbelladine, 6α-methoxybuphanidrine and filifoline, in addition to five known alkaloids, and phenol have been isolated from fresh bulbs of
Nerine filifolia (Amaryllidaceae). The structure and stereochemistry of the compounds were determined by physical and spectroscopic methods, including 1D and 2D NMR and mass spectroscopic techniques. An unusual circular dichroism response from filifoline has required a semi-synthetic derivatisation strategy towards key C-11
endo analogues of the β-crinane representative ambelline in which the nature of substituents was observed to have a profound effect on molecular ellipticity. Filifoline was not cytotoxic to myoblast (L6) cells and exhibited no anti-protozoal activity in an in vitro screen against four different parasitic protozoa. |
| doi_str_mv | 10.1016/j.phytochem.2004.12.009 |
| format | article |
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N-demethylbelladine, 6α-methoxybuphanidrine and filifoline are described for the first time from bulbs of
Nerine filifolia (Amaryllidaceae). The nicotinate ester in filifoline was observed to reverse molecular ellipticity as expressed in the shape of the CD curve.
The novel compounds
N-demethylbelladine, 6α-methoxybuphanidrine and filifoline, in addition to five known alkaloids, and phenol have been isolated from fresh bulbs of
Nerine filifolia (Amaryllidaceae). The structure and stereochemistry of the compounds were determined by physical and spectroscopic methods, including 1D and 2D NMR and mass spectroscopic techniques. An unusual circular dichroism response from filifoline has required a semi-synthetic derivatisation strategy towards key C-11
endo analogues of the β-crinane representative ambelline in which the nature of substituents was observed to have a profound effect on molecular ellipticity. Filifoline was not cytotoxic to myoblast (L6) cells and exhibited no anti-protozoal activity in an in vitro screen against four different parasitic protozoa.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2004.12.009</identifier><identifier>PMID: 15680994</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>11- O-Acetylambelline ; 6α-Hydroxybuphanidrine ; 6α-Methoxybuphanidrine ; Alkaloids ; Amaryllidaceae ; Amaryllidaceae Alkaloids - chemistry ; Amaryllidaceae Alkaloids - isolation & purification ; Ambelline ; Belladine ; Biological and medical sciences ; Bulbs ; Chemical constitution ; chemical structure ; Circular Dichroism ; Filifoline ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Leishmania donovani ; Liliaceae ; Liliaceae - chemistry ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular Structure ; N-Demethylbelladine ; Nerine filifolia ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Phenol ; phytochemicals ; plant extracts ; Plant physiology and development ; Plasmodium falciparum ; spectral analysis ; Trypanosoma cruzi ; Trypanosoma rhodesiense ; Undulatine</subject><ispartof>Phytochemistry (Oxford), 2005-02, Vol.66 (3), p.373-382</ispartof><rights>2004 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16475156$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15680994$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nair, Jerald J.</creatorcontrib><creatorcontrib>Campbell, William E.</creatorcontrib><creatorcontrib>Brun, Reto</creatorcontrib><creatorcontrib>Viladomat, Francesc</creatorcontrib><creatorcontrib>Codina, Carles</creatorcontrib><creatorcontrib>Bastida, Jaume</creatorcontrib><title>Alkaloids from Nerine filifolia</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>The alkaloids
N-demethylbelladine, 6α-methoxybuphanidrine and filifoline are described for the first time from bulbs of
Nerine filifolia (Amaryllidaceae). The nicotinate ester in filifoline was observed to reverse molecular ellipticity as expressed in the shape of the CD curve.
The novel compounds
N-demethylbelladine, 6α-methoxybuphanidrine and filifoline, in addition to five known alkaloids, and phenol have been isolated from fresh bulbs of
Nerine filifolia (Amaryllidaceae). The structure and stereochemistry of the compounds were determined by physical and spectroscopic methods, including 1D and 2D NMR and mass spectroscopic techniques. An unusual circular dichroism response from filifoline has required a semi-synthetic derivatisation strategy towards key C-11
endo analogues of the β-crinane representative ambelline in which the nature of substituents was observed to have a profound effect on molecular ellipticity. Filifoline was not cytotoxic to myoblast (L6) cells and exhibited no anti-protozoal activity in an in vitro screen against four different parasitic protozoa.</description><subject>11- O-Acetylambelline</subject><subject>6α-Hydroxybuphanidrine</subject><subject>6α-Methoxybuphanidrine</subject><subject>Alkaloids</subject><subject>Amaryllidaceae</subject><subject>Amaryllidaceae Alkaloids - chemistry</subject><subject>Amaryllidaceae Alkaloids - isolation & purification</subject><subject>Ambelline</subject><subject>Belladine</subject><subject>Biological and medical sciences</subject><subject>Bulbs</subject><subject>Chemical constitution</subject><subject>chemical structure</subject><subject>Circular Dichroism</subject><subject>Filifoline</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Leishmania donovani</subject><subject>Liliaceae</subject><subject>Liliaceae - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>N-Demethylbelladine</subject><subject>Nerine filifolia</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenol</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>Plant physiology and development</subject><subject>Plasmodium falciparum</subject><subject>spectral analysis</subject><subject>Trypanosoma cruzi</subject><subject>Trypanosoma rhodesiense</subject><subject>Undulatine</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpF0U1vGjEQBmCrSlUo7V8IXNLbbsfr7yNCSRsJtYeWs2Xs2WCyyxIbKvHvawRJTiONHo1m5iVkSqGmQOX3bb3fnA6D32BfNwC8pk0NYD6QMdWKVUwB3JAxAKOV4U0zIp9z3gKAEFJ-IiMqpAZj-JhM592z64YY8qxNQz_7hSnucNbGLrZDF90X8rF1Xcav1zohq4f7v4uf1fL3j8fFfFkha-ihwrVWhgelRMBgtBKm9B2aNUOpgwOllW_RsdYLHrjzrpFeKK-ZUlwaztiEfLvM3afh5Yj5YPuYPXad2-FwzFYqpg2XusDbKzyuewx2n2Lv0sm-nlTA3RW47F3XJrfzMb87yZUouLjpxbVusO4pFbP60wBl5Y9KSHPeaX4RWA7_FzHZ7CPuPIaY0B9sGKKlYM-B2K19C8SeA7G0sWUQ-w8qZXv8</recordid><startdate>20050201</startdate><enddate>20050201</enddate><creator>Nair, Jerald J.</creator><creator>Campbell, William E.</creator><creator>Brun, Reto</creator><creator>Viladomat, Francesc</creator><creator>Codina, Carles</creator><creator>Bastida, Jaume</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050201</creationdate><title>Alkaloids from Nerine filifolia</title><author>Nair, Jerald J. ; Campbell, William E. ; Brun, Reto ; Viladomat, Francesc ; Codina, Carles ; Bastida, Jaume</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-e321t-eb8794d775ded98759e32ae9b3e68da0787cfea3fc54d4aca26c57c8377469433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>11- O-Acetylambelline</topic><topic>6α-Hydroxybuphanidrine</topic><topic>6α-Methoxybuphanidrine</topic><topic>Alkaloids</topic><topic>Amaryllidaceae</topic><topic>Amaryllidaceae Alkaloids - chemistry</topic><topic>Amaryllidaceae Alkaloids - isolation & purification</topic><topic>Ambelline</topic><topic>Belladine</topic><topic>Biological and medical sciences</topic><topic>Bulbs</topic><topic>Chemical constitution</topic><topic>chemical structure</topic><topic>Circular Dichroism</topic><topic>Filifoline</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Leishmania donovani</topic><topic>Liliaceae</topic><topic>Liliaceae - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>N-Demethylbelladine</topic><topic>Nerine filifolia</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenol</topic><topic>phytochemicals</topic><topic>plant extracts</topic><topic>Plant physiology and development</topic><topic>Plasmodium falciparum</topic><topic>spectral analysis</topic><topic>Trypanosoma cruzi</topic><topic>Trypanosoma rhodesiense</topic><topic>Undulatine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nair, Jerald J.</creatorcontrib><creatorcontrib>Campbell, William E.</creatorcontrib><creatorcontrib>Brun, Reto</creatorcontrib><creatorcontrib>Viladomat, Francesc</creatorcontrib><creatorcontrib>Codina, Carles</creatorcontrib><creatorcontrib>Bastida, Jaume</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nair, Jerald J.</au><au>Campbell, William E.</au><au>Brun, Reto</au><au>Viladomat, Francesc</au><au>Codina, Carles</au><au>Bastida, Jaume</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Alkaloids from Nerine filifolia</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2005-02-01</date><risdate>2005</risdate><volume>66</volume><issue>3</issue><spage>373</spage><epage>382</epage><pages>373-382</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>The alkaloids
N-demethylbelladine, 6α-methoxybuphanidrine and filifoline are described for the first time from bulbs of
Nerine filifolia (Amaryllidaceae). The nicotinate ester in filifoline was observed to reverse molecular ellipticity as expressed in the shape of the CD curve.
The novel compounds
N-demethylbelladine, 6α-methoxybuphanidrine and filifoline, in addition to five known alkaloids, and phenol have been isolated from fresh bulbs of
Nerine filifolia (Amaryllidaceae). The structure and stereochemistry of the compounds were determined by physical and spectroscopic methods, including 1D and 2D NMR and mass spectroscopic techniques. An unusual circular dichroism response from filifoline has required a semi-synthetic derivatisation strategy towards key C-11
endo analogues of the β-crinane representative ambelline in which the nature of substituents was observed to have a profound effect on molecular ellipticity. Filifoline was not cytotoxic to myoblast (L6) cells and exhibited no anti-protozoal activity in an in vitro screen against four different parasitic protozoa.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>15680994</pmid><doi>10.1016/j.phytochem.2004.12.009</doi><tpages>10</tpages></addata></record> |
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| ispartof | Phytochemistry (Oxford), 2005-02, Vol.66 (3), p.373-382 |
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| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | 11- O-Acetylambelline 6α-Hydroxybuphanidrine 6α-Methoxybuphanidrine Alkaloids Amaryllidaceae Amaryllidaceae Alkaloids - chemistry Amaryllidaceae Alkaloids - isolation & purification Ambelline Belladine Biological and medical sciences Bulbs Chemical constitution chemical structure Circular Dichroism Filifoline Fundamental and applied biological sciences. Psychology General pharmacology Leishmania donovani Liliaceae Liliaceae - chemistry Magnetic Resonance Spectroscopy Medical sciences Molecular Structure N-Demethylbelladine Nerine filifolia Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phenol phytochemicals plant extracts Plant physiology and development Plasmodium falciparum spectral analysis Trypanosoma cruzi Trypanosoma rhodesiense Undulatine |
| title | Alkaloids from Nerine filifolia |
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