Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi
A sulfated emodin glucoside, emodin 8-O-beta-D-glucopyranosyl-6-O-sulfate (1), was isolated from the roots of Rheum emodi in an investigation of the active constituents of this Nepalese medicinal plant, and its structure was determined by spectroscopic and chemical methods. Additionally, two rare au...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2003-08, Vol.66 (8), p.1107-1109 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Krenn, L Presser, A Pradhan, R Bahr, B Paper, D.H Mayer, K.K Kopp, B |
| description | A sulfated emodin glucoside, emodin 8-O-beta-D-glucopyranosyl-6-O-sulfate (1), was isolated from the roots of Rheum emodi in an investigation of the active constituents of this Nepalese medicinal plant, and its structure was determined by spectroscopic and chemical methods. Additionally, two rare auronols, carpusin (2) and maesopsin (3), besides other anthraquinones and phenolics, were isolated and identified. Compounds 2 and 3 showed significant antioxidant activity in the DPPH assay, while chrysophanol, physcion, and emodin and their 8-O-glucosides were found to be inactive. |
| doi_str_mv | 10.1021/np0301442 |
| format | Article |
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Additionally, two rare auronols, carpusin (2) and maesopsin (3), besides other anthraquinones and phenolics, were isolated and identified. Compounds 2 and 3 showed significant antioxidant activity in the DPPH assay, while chrysophanol, physcion, and emodin and their 8-O-glucosides were found to be inactive.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np0301442</identifier><identifier>PMID: 12932135</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>1,1-diphenyl-2-picrylhydrazyl ; anthraquinones ; Anthraquinones - chemistry ; Anthraquinones - isolation & purification ; Anthraquinones - pharmacology ; antioxidant activity ; antioxidants ; Antioxidants - chemistry ; Antioxidants - isolation & purification ; Antioxidants - pharmacology ; auronol ; Benzofurans - chemistry ; Benzofurans - isolation & purification ; Benzofurans - pharmacology ; Biological and medical sciences ; Biphenyl Compounds ; carpusin ; chemical structure ; free radical scavenging effect ; free radicals ; General pharmacology ; glucose ; glucosides ; Glycosides - chemistry ; Glycosides - isolation & purification ; Glycosides - pharmacology ; glycosidic linkages ; Inhibitory Concentration 50 ; Medical sciences ; medicinal plants ; Molecular Structure ; Nepal ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phenolic compounds ; phytochemicals ; Picrates - pharmacology ; plant extracts ; Plant Roots - chemistry ; Plants, Medicinal - chemistry ; Polygonaceae ; Rheum ; Rheum - chemistry ; Rheum australe ; Rheum emodi ; roots ; spectral analysis ; sulfates ; sulfemodin 8-O-beta-d-glucoside</subject><ispartof>Journal of natural products (Washington, D.C.), 2003-08, Vol.66 (8), p.1107-1109</ispartof><rights>2003 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=15087920$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12932135$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Krenn, L</creatorcontrib><creatorcontrib>Presser, A</creatorcontrib><creatorcontrib>Pradhan, R</creatorcontrib><creatorcontrib>Bahr, B</creatorcontrib><creatorcontrib>Paper, D.H</creatorcontrib><creatorcontrib>Mayer, K.K</creatorcontrib><creatorcontrib>Kopp, B</creatorcontrib><title>Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A sulfated emodin glucoside, emodin 8-O-beta-D-glucopyranosyl-6-O-sulfate (1), was isolated from the roots of Rheum emodi in an investigation of the active constituents of this Nepalese medicinal plant, and its structure was determined by spectroscopic and chemical methods. Additionally, two rare auronols, carpusin (2) and maesopsin (3), besides other anthraquinones and phenolics, were isolated and identified. Compounds 2 and 3 showed significant antioxidant activity in the DPPH assay, while chrysophanol, physcion, and emodin and their 8-O-glucosides were found to be inactive.</description><subject>1,1-diphenyl-2-picrylhydrazyl</subject><subject>anthraquinones</subject><subject>Anthraquinones - chemistry</subject><subject>Anthraquinones - isolation & purification</subject><subject>Anthraquinones - pharmacology</subject><subject>antioxidant activity</subject><subject>antioxidants</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - isolation & purification</subject><subject>Antioxidants - pharmacology</subject><subject>auronol</subject><subject>Benzofurans - chemistry</subject><subject>Benzofurans - isolation & purification</subject><subject>Benzofurans - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Biphenyl Compounds</subject><subject>carpusin</subject><subject>chemical structure</subject><subject>free radical scavenging effect</subject><subject>free radicals</subject><subject>General pharmacology</subject><subject>glucose</subject><subject>glucosides</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - isolation & purification</subject><subject>Glycosides - pharmacology</subject><subject>glycosidic linkages</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Molecular Structure</subject><subject>Nepal</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phenolic compounds</subject><subject>phytochemicals</subject><subject>Picrates - pharmacology</subject><subject>plant extracts</subject><subject>Plant Roots - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>Polygonaceae</subject><subject>Rheum</subject><subject>Rheum - chemistry</subject><subject>Rheum australe</subject><subject>Rheum emodi</subject><subject>roots</subject><subject>spectral analysis</subject><subject>sulfates</subject><subject>sulfemodin 8-O-beta-d-glucoside</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0c9P2zAUB3ALDa0d22H_wPCF2wz-ESfxcYNRkIqo1lbiFr3GdmuW2FmcaCDxx2NRYKd3-H70fdJ7CH1l9JRRzs58RwVlWcYP0JRJTklOufyAppTlgogyzyboU4z3lCam5Ec0YVwJzoScoqfl2FjTBu08Lskt2ZgByAXZNmMdotPmOwbszT8cE4PBaAx-2PXwd3Q-eIO3zeO78y-hCw9Op4m7nfGhcTWuQ9uF0euIbR9a_Htnxha_rPyMDi000Xx5nUdofflrdX5F5rez6_Mfc2K5UgOxWpemBKE30oCwWmZ1rRXLmBaFraFUIrdSs1JIAZQZxtSmoCKjIk-ZASaO0Ld9bzduWqOrrnct9I_V2xkSOHkFEGtobA--dvG_k7QsFKfJkb1zcTAP7zn0f6q8EIWsVotlJX_OVrO7G14tkj_eewuhgm2fOtdLTln6FpWqVFw8Awi-hSk</recordid><startdate>20030801</startdate><enddate>20030801</enddate><creator>Krenn, L</creator><creator>Presser, A</creator><creator>Pradhan, R</creator><creator>Bahr, B</creator><creator>Paper, D.H</creator><creator>Mayer, K.K</creator><creator>Kopp, B</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope></search><sort><creationdate>20030801</creationdate><title>Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi</title><author>Krenn, L ; Presser, A ; Pradhan, R ; Bahr, B ; Paper, D.H ; Mayer, K.K ; Kopp, B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f299t-fdd8e8a3db5ea3fd54ccd9141d37fca8936f5d18353a01e119b7034036a89ea13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>1,1-diphenyl-2-picrylhydrazyl</topic><topic>anthraquinones</topic><topic>Anthraquinones - chemistry</topic><topic>Anthraquinones - isolation & purification</topic><topic>Anthraquinones - pharmacology</topic><topic>antioxidant activity</topic><topic>antioxidants</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - isolation & purification</topic><topic>Antioxidants - pharmacology</topic><topic>auronol</topic><topic>Benzofurans - chemistry</topic><topic>Benzofurans - isolation & purification</topic><topic>Benzofurans - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Biphenyl Compounds</topic><topic>carpusin</topic><topic>chemical structure</topic><topic>free radical scavenging effect</topic><topic>free radicals</topic><topic>General pharmacology</topic><topic>glucose</topic><topic>glucosides</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - isolation & purification</topic><topic>Glycosides - pharmacology</topic><topic>glycosidic linkages</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Molecular Structure</topic><topic>Nepal</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phenolic compounds</topic><topic>phytochemicals</topic><topic>Picrates - pharmacology</topic><topic>plant extracts</topic><topic>Plant Roots - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>Polygonaceae</topic><topic>Rheum</topic><topic>Rheum - chemistry</topic><topic>Rheum australe</topic><topic>Rheum emodi</topic><topic>roots</topic><topic>spectral analysis</topic><topic>sulfates</topic><topic>sulfemodin 8-O-beta-d-glucoside</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krenn, L</creatorcontrib><creatorcontrib>Presser, A</creatorcontrib><creatorcontrib>Pradhan, R</creatorcontrib><creatorcontrib>Bahr, B</creatorcontrib><creatorcontrib>Paper, D.H</creatorcontrib><creatorcontrib>Mayer, K.K</creatorcontrib><creatorcontrib>Kopp, B</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krenn, L</au><au>Presser, A</au><au>Pradhan, R</au><au>Bahr, B</au><au>Paper, D.H</au><au>Mayer, K.K</au><au>Kopp, B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2003-08-01</date><risdate>2003</risdate><volume>66</volume><issue>8</issue><spage>1107</spage><epage>1109</epage><pages>1107-1109</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>A sulfated emodin glucoside, emodin 8-O-beta-D-glucopyranosyl-6-O-sulfate (1), was isolated from the roots of Rheum emodi in an investigation of the active constituents of this Nepalese medicinal plant, and its structure was determined by spectroscopic and chemical methods. Additionally, two rare auronols, carpusin (2) and maesopsin (3), besides other anthraquinones and phenolics, were isolated and identified. Compounds 2 and 3 showed significant antioxidant activity in the DPPH assay, while chrysophanol, physcion, and emodin and their 8-O-glucosides were found to be inactive.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>12932135</pmid><doi>10.1021/np0301442</doi><tpages>3</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2003-08, Vol.66 (8), p.1107-1109 |
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| source | ACS Publications; MEDLINE |
| subjects | 1,1-diphenyl-2-picrylhydrazyl anthraquinones Anthraquinones - chemistry Anthraquinones - isolation & purification Anthraquinones - pharmacology antioxidant activity antioxidants Antioxidants - chemistry Antioxidants - isolation & purification Antioxidants - pharmacology auronol Benzofurans - chemistry Benzofurans - isolation & purification Benzofurans - pharmacology Biological and medical sciences Biphenyl Compounds carpusin chemical structure free radical scavenging effect free radicals General pharmacology glucose glucosides Glycosides - chemistry Glycosides - isolation & purification Glycosides - pharmacology glycosidic linkages Inhibitory Concentration 50 Medical sciences medicinal plants Molecular Structure Nepal Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phenolic compounds phytochemicals Picrates - pharmacology plant extracts Plant Roots - chemistry Plants, Medicinal - chemistry Polygonaceae Rheum Rheum - chemistry Rheum australe Rheum emodi roots spectral analysis sulfates sulfemodin 8-O-beta-d-glucoside |
| title | Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi |
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