Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii
From the water soluble fraction of the dried fruits of Alangium lamarckii, four tetrahydroisoquinoline-monoterpene glycosides, 6- O-methyl- N-deacetylisoipecosidic acid, 7- O-methyl- N-deacetylisoipecosidic acid, 6,7-di- O-methyl- N-deacetylisoipecosidic acid and 6″- O-α- d-glucopyranosyl-6- O-methy...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2001-03, Vol.56 (6), p.623-630 |
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| container_title | Phytochemistry (Oxford) |
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| creator | Itoh, Atsuko Tanahashi, Takao Tabata, Masako Shikata, Miho Kakite, Michiko Nagai, Maho Nagakura, Naotaka |
| description | From the water soluble fraction of the dried fruits of
Alangium lamarckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-
O-methyl-
N-deacetylisoipecosidic acid, 7-
O-methyl-
N-deacetylisoipecosidic acid, 6,7-di-
O-methyl-
N-deacetylisoipecosidic acid and 6″-
O-α-
d-glucopyranosyl-6-
O-methyl-
N-deacetylisoipecosidic acid, and an iridoid glycoside, 6′-
O-α-
d-glucopyranosylloganic acid, were isolated, together with six known compounds. The structures of the previously unknown compounds were determined by spectroscopic and chemical means. The significance of these glucosides in the biogenesis of
Alangium alkaloids is discussed; 6-
O-methyl-
N-deacetylisoipecosidic acid was also chemically converted into 10-
O-demethylprotoemetine and dihydroisoalangine. |
| doi_str_mv | 10.1016/S0031-9422(00)00417-9 |
| format | Article |
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Alangium lamarckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-
O-methyl-
N-deacetylisoipecosidic acid, 7-
O-methyl-
N-deacetylisoipecosidic acid, 6,7-di-
O-methyl-
N-deacetylisoipecosidic acid and 6″-
O-α-
d-glucopyranosyl-6-
O-methyl-
N-deacetylisoipecosidic acid, and an iridoid glycoside, 6′-
O-α-
d-glucopyranosylloganic acid, were isolated, together with six known compounds. The structures of the previously unknown compounds were determined by spectroscopic and chemical means. The significance of these glucosides in the biogenesis of
Alangium alkaloids is discussed; 6-
O-methyl-
N-deacetylisoipecosidic acid was also chemically converted into 10-
O-demethylprotoemetine and dihydroisoalangine.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/S0031-9422(00)00417-9</identifier><identifier>PMID: 11281140</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>6′- O-α- d-glucopyranosylloganic acid ; Alangiaceae ; Alangium lamarckii ; Alkaloids ; Asteraceae - chemistry ; Biological and medical sciences ; Chemical constitution ; Fruits ; Fundamental and applied biological sciences. Psychology ; Glycosides - chemistry ; Glycosides - isolation & purification ; Ipecoside ; Iridoid glycoside ; Isoquinolines - chemistry ; Isoquinolines - isolation & purification ; Magnetic Resonance Spectroscopy ; Medicine, Traditional ; Molecular Structure ; N-Deacetylisoipecosidic acids ; Phytotherapy ; Plant physiology and development ; Plants, Medicinal - chemistry ; Pyrans - chemistry ; Pyrans - isolation & purification ; Structure elucidation ; Terpenes - chemistry ; Terpenes - isolation & purification ; Tetrahydroisoquinoline-monoterpene glycosides</subject><ispartof>Phytochemistry (Oxford), 2001-03, Vol.56 (6), p.623-630</ispartof><rights>2001 Elsevier Science Ltd</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-a30e34598cd7bfbbaf23980601d0217990e99a3029bc0b00297d9f8fc4cec3a53</citedby><cites>FETCH-LOGICAL-c389t-a30e34598cd7bfbbaf23980601d0217990e99a3029bc0b00297d9f8fc4cec3a53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0031-9422(00)00417-9$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3549,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=909886$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11281140$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Itoh, Atsuko</creatorcontrib><creatorcontrib>Tanahashi, Takao</creatorcontrib><creatorcontrib>Tabata, Masako</creatorcontrib><creatorcontrib>Shikata, Miho</creatorcontrib><creatorcontrib>Kakite, Michiko</creatorcontrib><creatorcontrib>Nagai, Maho</creatorcontrib><creatorcontrib>Nagakura, Naotaka</creatorcontrib><title>Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>From the water soluble fraction of the dried fruits of
Alangium lamarckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-
O-methyl-
N-deacetylisoipecosidic acid, 7-
O-methyl-
N-deacetylisoipecosidic acid, 6,7-di-
O-methyl-
N-deacetylisoipecosidic acid and 6″-
O-α-
d-glucopyranosyl-6-
O-methyl-
N-deacetylisoipecosidic acid, and an iridoid glycoside, 6′-
O-α-
d-glucopyranosylloganic acid, were isolated, together with six known compounds. The structures of the previously unknown compounds were determined by spectroscopic and chemical means. The significance of these glucosides in the biogenesis of
Alangium alkaloids is discussed; 6-
O-methyl-
N-deacetylisoipecosidic acid was also chemically converted into 10-
O-demethylprotoemetine and dihydroisoalangine.</description><subject>6′- O-α- d-glucopyranosylloganic acid</subject><subject>Alangiaceae</subject><subject>Alangium lamarckii</subject><subject>Alkaloids</subject><subject>Asteraceae - chemistry</subject><subject>Biological and medical sciences</subject><subject>Chemical constitution</subject><subject>Fruits</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - isolation & purification</subject><subject>Ipecoside</subject><subject>Iridoid glycoside</subject><subject>Isoquinolines - chemistry</subject><subject>Isoquinolines - isolation & purification</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medicine, Traditional</subject><subject>Molecular Structure</subject><subject>N-Deacetylisoipecosidic acids</subject><subject>Phytotherapy</subject><subject>Plant physiology and development</subject><subject>Plants, Medicinal - chemistry</subject><subject>Pyrans - chemistry</subject><subject>Pyrans - isolation & purification</subject><subject>Structure elucidation</subject><subject>Terpenes - chemistry</subject><subject>Terpenes - isolation & purification</subject><subject>Tetrahydroisoquinoline-monoterpene glycosides</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtLxDAUhYMozvj4CUpBEF1Ub5q2aVYyDL5AEFHXIU1ux2jbjElHmH9vxhl06epsvnPv4SPkiMIFBVpePgMwmoo8y84AzgFyylOxRca04ixlHGCbjH-REdkL4R0AiqIsd8mI0qyiNIcxeXrBwau3pfHOBve5sL1rbY9p53o3oJ9jj4nqTWK9Nc6aZNYutQvWYEga77pk0qp-Zhdd0qpOef1h7QHZaVQb8HCT--T15vplepc-PN7eTycPqWaVGFLFAFleiEobXjd1rZqMiQpKoAYyyoUAFCJCmag11BCTG9FUjc41aqYKtk9O13fnPu7GMMjOBo1tHIRuESTnQAXjIoLFGtTeheCxkXNv49ilpCBXLuWPS7kSJQHkj0u56h1vHizqDs1fayMvAicbQAWt2sarXtvwywkQVVVG6mpNYZTxZdHLoC32Go31qAcZtf4z5BunVJEu</recordid><startdate>20010301</startdate><enddate>20010301</enddate><creator>Itoh, Atsuko</creator><creator>Tanahashi, Takao</creator><creator>Tabata, Masako</creator><creator>Shikata, Miho</creator><creator>Kakite, Michiko</creator><creator>Nagai, Maho</creator><creator>Nagakura, Naotaka</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20010301</creationdate><title>Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii</title><author>Itoh, Atsuko ; Tanahashi, Takao ; Tabata, Masako ; Shikata, Miho ; Kakite, Michiko ; Nagai, Maho ; Nagakura, Naotaka</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-a30e34598cd7bfbbaf23980601d0217990e99a3029bc0b00297d9f8fc4cec3a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>6′- O-α- d-glucopyranosylloganic acid</topic><topic>Alangiaceae</topic><topic>Alangium lamarckii</topic><topic>Alkaloids</topic><topic>Asteraceae - chemistry</topic><topic>Biological and medical sciences</topic><topic>Chemical constitution</topic><topic>Fruits</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - isolation & purification</topic><topic>Ipecoside</topic><topic>Iridoid glycoside</topic><topic>Isoquinolines - chemistry</topic><topic>Isoquinolines - isolation & purification</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medicine, Traditional</topic><topic>Molecular Structure</topic><topic>N-Deacetylisoipecosidic acids</topic><topic>Phytotherapy</topic><topic>Plant physiology and development</topic><topic>Plants, Medicinal - chemistry</topic><topic>Pyrans - chemistry</topic><topic>Pyrans - isolation & purification</topic><topic>Structure elucidation</topic><topic>Terpenes - chemistry</topic><topic>Terpenes - isolation & purification</topic><topic>Tetrahydroisoquinoline-monoterpene glycosides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Itoh, Atsuko</creatorcontrib><creatorcontrib>Tanahashi, Takao</creatorcontrib><creatorcontrib>Tabata, Masako</creatorcontrib><creatorcontrib>Shikata, Miho</creatorcontrib><creatorcontrib>Kakite, Michiko</creatorcontrib><creatorcontrib>Nagai, Maho</creatorcontrib><creatorcontrib>Nagakura, Naotaka</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Itoh, Atsuko</au><au>Tanahashi, Takao</au><au>Tabata, Masako</au><au>Shikata, Miho</au><au>Kakite, Michiko</au><au>Nagai, Maho</au><au>Nagakura, Naotaka</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2001-03-01</date><risdate>2001</risdate><volume>56</volume><issue>6</issue><spage>623</spage><epage>630</epage><pages>623-630</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>From the water soluble fraction of the dried fruits of
Alangium lamarckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-
O-methyl-
N-deacetylisoipecosidic acid, 7-
O-methyl-
N-deacetylisoipecosidic acid, 6,7-di-
O-methyl-
N-deacetylisoipecosidic acid and 6″-
O-α-
d-glucopyranosyl-6-
O-methyl-
N-deacetylisoipecosidic acid, and an iridoid glycoside, 6′-
O-α-
d-glucopyranosylloganic acid, were isolated, together with six known compounds. The structures of the previously unknown compounds were determined by spectroscopic and chemical means. The significance of these glucosides in the biogenesis of
Alangium alkaloids is discussed; 6-
O-methyl-
N-deacetylisoipecosidic acid was also chemically converted into 10-
O-demethylprotoemetine and dihydroisoalangine.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>11281140</pmid><doi>10.1016/S0031-9422(00)00417-9</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Phytochemistry (Oxford), 2001-03, Vol.56 (6), p.623-630 |
| issn | 0031-9422 1873-3700 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_77019379 |
| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | 6′- O-α- d-glucopyranosylloganic acid Alangiaceae Alangium lamarckii Alkaloids Asteraceae - chemistry Biological and medical sciences Chemical constitution Fruits Fundamental and applied biological sciences. Psychology Glycosides - chemistry Glycosides - isolation & purification Ipecoside Iridoid glycoside Isoquinolines - chemistry Isoquinolines - isolation & purification Magnetic Resonance Spectroscopy Medicine, Traditional Molecular Structure N-Deacetylisoipecosidic acids Phytotherapy Plant physiology and development Plants, Medicinal - chemistry Pyrans - chemistry Pyrans - isolation & purification Structure elucidation Terpenes - chemistry Terpenes - isolation & purification Tetrahydroisoquinoline-monoterpene glycosides |
| title | Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii |
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