Isolation of Echinocystic Acid-3-O-Sulfate, a New Triterpene, from Tetrapleura tetraptera, and Evaluation of the Mutagenic Potential of Molluscicidal Extracts and Isolates
A known triterpene glycoside, 3-O-[beta-D-glucopyranosyl-(1"-6')-2'-acetamido-2'-deoxy-beta-D-gluco pyranosyl]olean-12-en-28-oic acid [3], and new sulfated triterpene, echinocystic acid-3-O-sodium sulfate [4], have been isolated from the stem bark of Tetrapleura tetraptera. Compo...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1993-11, Vol.56 (11), p.1872-1877 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Ngassapa, Olipa Beecher, Christopher W. W Pezzuto, John M Farnsworth, Norman R Henderson, Thomas O Boye, Gilbert L |
| description | A known triterpene glycoside, 3-O-[beta-D-glucopyranosyl-(1"-6')-2'-acetamido-2'-deoxy-beta-D-gluco pyranosyl]olean-12-en-28-oic acid [3], and new sulfated triterpene, echinocystic acid-3-O-sodium sulfate [4], have been isolated from the stem bark of Tetrapleura tetraptera. Compound 3 was 100% lethal to Biomphalaria glabrata at 20 ppm, while 4 was not molluscicidal at the same concentration. In a forward mutation assay utilizing Salmonella typhimurium strain TM677, T. tetraptera stem bark extracts were found to be mutagenic in the absence of a metabolic activating system (S-9). An MeOH extract of the fruit exhibited weak mutagenic activity only in the presence of S-9. The stem bark isolates, which included aridanin [1], 3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl)echinocystic acid [2], and compounds 3 and 4, were not mutagenic either with or without metabolic activation. |
| doi_str_mv | 10.1021/np50101a002 |
| format | Article |
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W ; Pezzuto, John M ; Farnsworth, Norman R ; Henderson, Thomas O ; Boye, Gilbert L</creator><creatorcontrib>Ngassapa, Olipa ; Beecher, Christopher W. W ; Pezzuto, John M ; Farnsworth, Norman R ; Henderson, Thomas O ; Boye, Gilbert L</creatorcontrib><description>A known triterpene glycoside, 3-O-[beta-D-glucopyranosyl-(1"-6')-2'-acetamido-2'-deoxy-beta-D-gluco pyranosyl]olean-12-en-28-oic acid [3], and new sulfated triterpene, echinocystic acid-3-O-sodium sulfate [4], have been isolated from the stem bark of Tetrapleura tetraptera. Compound 3 was 100% lethal to Biomphalaria glabrata at 20 ppm, while 4 was not molluscicidal at the same concentration. In a forward mutation assay utilizing Salmonella typhimurium strain TM677, T. tetraptera stem bark extracts were found to be mutagenic in the absence of a metabolic activating system (S-9). An MeOH extract of the fruit exhibited weak mutagenic activity only in the presence of S-9. The stem bark isolates, which included aridanin [1], 3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl)echinocystic acid [2], and compounds 3 and 4, were not mutagenic either with or without metabolic activation.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np50101a002</identifier><identifier>PMID: 8289059</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Biomphalaria - drug effects ; BIOMPHALARIA GLABRATA ; Biotransformation ; DESARROLLO DE UN PRODUCTO ; DEVELOPPEMENT DE PRODUIT ; EXTRACTOS VEGETALES ; EXTRAIT D'ORIGINE VEGETALE ; Fabaceae - chemistry ; In Vitro Techniques ; LEGUMINOSAE ; Magnetic Resonance Spectroscopy ; MOLECULAR STRUCTURE ; Molluscacides - isolation & purification ; Molluscacides - pharmacokinetics ; Molluscacides - toxicity ; MOLLUSCICIDAL PROPERTIES ; MOLLUSCICIDE ; MOLLUSCICIDES ; MOLUSCOCIDAS ; MUTAGENE ; MUTAGENOS ; MUTAGENS ; Mutagens - isolation & purification ; Mutagens - pharmacokinetics ; Mutagens - toxicity ; NEW PRODUCTS ; Oleanolic Acid - analogs & derivatives ; Oleanolic Acid - isolation & purification ; Oleanolic Acid - pharmacokinetics ; Oleanolic Acid - toxicity ; PLANT EXTRACTS ; Plant Extracts - toxicity ; Plants, Medicinal ; PRODUCT DEVELOPMENT ; Rats ; Salmonella typhimurium - genetics ; Spectrophotometry, Infrared ; STRUCTURE ; TOXICIDAD ; TOXICITE ; TOXICITY ; TRITERPENOIDE ; TRITERPENOIDOS ; TRITERPENOIDS ; X-Ray Diffraction</subject><ispartof>Journal of natural products (Washington, D.C.), 1993-11, Vol.56 (11), p.1872-1877</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a439t-1c8469bfedc5ce5215454dbb81e5e8994ed0b4e9d5d172e3692a250cc9e43bcb3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np50101a002$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np50101a002$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8289059$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ngassapa, Olipa</creatorcontrib><creatorcontrib>Beecher, Christopher W. W</creatorcontrib><creatorcontrib>Pezzuto, John M</creatorcontrib><creatorcontrib>Farnsworth, Norman R</creatorcontrib><creatorcontrib>Henderson, Thomas O</creatorcontrib><creatorcontrib>Boye, Gilbert L</creatorcontrib><title>Isolation of Echinocystic Acid-3-O-Sulfate, a New Triterpene, from Tetrapleura tetraptera, and Evaluation of the Mutagenic Potential of Molluscicidal Extracts and Isolates</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A known triterpene glycoside, 3-O-[beta-D-glucopyranosyl-(1"-6')-2'-acetamido-2'-deoxy-beta-D-gluco pyranosyl]olean-12-en-28-oic acid [3], and new sulfated triterpene, echinocystic acid-3-O-sodium sulfate [4], have been isolated from the stem bark of Tetrapleura tetraptera. Compound 3 was 100% lethal to Biomphalaria glabrata at 20 ppm, while 4 was not molluscicidal at the same concentration. In a forward mutation assay utilizing Salmonella typhimurium strain TM677, T. tetraptera stem bark extracts were found to be mutagenic in the absence of a metabolic activating system (S-9). An MeOH extract of the fruit exhibited weak mutagenic activity only in the presence of S-9. The stem bark isolates, which included aridanin [1], 3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl)echinocystic acid [2], and compounds 3 and 4, were not mutagenic either with or without metabolic activation.</description><subject>Animals</subject><subject>Biomphalaria - drug effects</subject><subject>BIOMPHALARIA GLABRATA</subject><subject>Biotransformation</subject><subject>DESARROLLO DE UN PRODUCTO</subject><subject>DEVELOPPEMENT DE PRODUIT</subject><subject>EXTRACTOS VEGETALES</subject><subject>EXTRAIT D'ORIGINE VEGETALE</subject><subject>Fabaceae - chemistry</subject><subject>In Vitro Techniques</subject><subject>LEGUMINOSAE</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>MOLECULAR STRUCTURE</subject><subject>Molluscacides - isolation & purification</subject><subject>Molluscacides - pharmacokinetics</subject><subject>Molluscacides - toxicity</subject><subject>MOLLUSCICIDAL PROPERTIES</subject><subject>MOLLUSCICIDE</subject><subject>MOLLUSCICIDES</subject><subject>MOLUSCOCIDAS</subject><subject>MUTAGENE</subject><subject>MUTAGENOS</subject><subject>MUTAGENS</subject><subject>Mutagens - isolation & purification</subject><subject>Mutagens - pharmacokinetics</subject><subject>Mutagens - toxicity</subject><subject>NEW PRODUCTS</subject><subject>Oleanolic Acid - analogs & derivatives</subject><subject>Oleanolic Acid - isolation & purification</subject><subject>Oleanolic Acid - pharmacokinetics</subject><subject>Oleanolic Acid - toxicity</subject><subject>PLANT EXTRACTS</subject><subject>Plant Extracts - toxicity</subject><subject>Plants, Medicinal</subject><subject>PRODUCT DEVELOPMENT</subject><subject>Rats</subject><subject>Salmonella typhimurium - genetics</subject><subject>Spectrophotometry, Infrared</subject><subject>STRUCTURE</subject><subject>TOXICIDAD</subject><subject>TOXICITE</subject><subject>TOXICITY</subject><subject>TRITERPENOIDE</subject><subject>TRITERPENOIDOS</subject><subject>TRITERPENOIDS</subject><subject>X-Ray Diffraction</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1u1DAURi0EKtPCih0SknddgMGO7Uy8rKoBKqY_YlIWbCzHuWldMnFkO6V9Jl4St6lGLFjZuufou1cfQm8Y_chowT4No6SMMkNp8QwtmCwoKWkhn6MFZSUnvCrFS7Qf4w2llFMl99BeVVSKSrVAf06i701yfsC-wyt77QZv72NyFh9Z1xJOzslm6juT4AM2-Ax-4zq4BGGEIU-64Le4hhTM2MMUDE6P_8xN1ocWr25NP-3y0zXg0ymZKxjyggufYEjO9A_o1Pf9FK3LS_NgdZdjbIqPGfOJEF-hF53pI7x-eg_Q5edVffyVrM-_nBwfrYkRXCXCbCVK1XTQWmlBFkwKKdqmqRhIqJQS0NJGgGply5YF8FIVppDUWgWCN7bhB-j9nGuDjzFAp8fgtibca0b1Q-P6n8az_W62x6nZQrtznyrOnMzcxQR3O2zCL10u-VLq-mKj19_rb2c_yx9aZP_t7HfGa3MVXNSXGyU4ZaLK8HCGxkZ946cw5CL-e9ZfeEeiqA</recordid><startdate>19931101</startdate><enddate>19931101</enddate><creator>Ngassapa, Olipa</creator><creator>Beecher, Christopher W. 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W ; Pezzuto, John M ; Farnsworth, Norman R ; Henderson, Thomas O ; Boye, Gilbert L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a439t-1c8469bfedc5ce5215454dbb81e5e8994ed0b4e9d5d172e3692a250cc9e43bcb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Animals</topic><topic>Biomphalaria - drug effects</topic><topic>BIOMPHALARIA GLABRATA</topic><topic>Biotransformation</topic><topic>DESARROLLO DE UN PRODUCTO</topic><topic>DEVELOPPEMENT DE PRODUIT</topic><topic>EXTRACTOS VEGETALES</topic><topic>EXTRAIT D'ORIGINE VEGETALE</topic><topic>Fabaceae - chemistry</topic><topic>In Vitro Techniques</topic><topic>LEGUMINOSAE</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>MOLECULAR STRUCTURE</topic><topic>Molluscacides - isolation & purification</topic><topic>Molluscacides - pharmacokinetics</topic><topic>Molluscacides - toxicity</topic><topic>MOLLUSCICIDAL PROPERTIES</topic><topic>MOLLUSCICIDE</topic><topic>MOLLUSCICIDES</topic><topic>MOLUSCOCIDAS</topic><topic>MUTAGENE</topic><topic>MUTAGENOS</topic><topic>MUTAGENS</topic><topic>Mutagens - isolation & purification</topic><topic>Mutagens - pharmacokinetics</topic><topic>Mutagens - toxicity</topic><topic>NEW PRODUCTS</topic><topic>Oleanolic Acid - analogs & derivatives</topic><topic>Oleanolic Acid - isolation & purification</topic><topic>Oleanolic Acid - pharmacokinetics</topic><topic>Oleanolic Acid - toxicity</topic><topic>PLANT EXTRACTS</topic><topic>Plant Extracts - toxicity</topic><topic>Plants, Medicinal</topic><topic>PRODUCT DEVELOPMENT</topic><topic>Rats</topic><topic>Salmonella typhimurium - genetics</topic><topic>Spectrophotometry, Infrared</topic><topic>STRUCTURE</topic><topic>TOXICIDAD</topic><topic>TOXICITE</topic><topic>TOXICITY</topic><topic>TRITERPENOIDE</topic><topic>TRITERPENOIDOS</topic><topic>TRITERPENOIDS</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ngassapa, Olipa</creatorcontrib><creatorcontrib>Beecher, Christopher W. W</creatorcontrib><creatorcontrib>Pezzuto, John M</creatorcontrib><creatorcontrib>Farnsworth, Norman R</creatorcontrib><creatorcontrib>Henderson, Thomas O</creatorcontrib><creatorcontrib>Boye, Gilbert L</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ngassapa, Olipa</au><au>Beecher, Christopher W. W</au><au>Pezzuto, John M</au><au>Farnsworth, Norman R</au><au>Henderson, Thomas O</au><au>Boye, Gilbert L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation of Echinocystic Acid-3-O-Sulfate, a New Triterpene, from Tetrapleura tetraptera, and Evaluation of the Mutagenic Potential of Molluscicidal Extracts and Isolates</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1993-11-01</date><risdate>1993</risdate><volume>56</volume><issue>11</issue><spage>1872</spage><epage>1877</epage><pages>1872-1877</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>A known triterpene glycoside, 3-O-[beta-D-glucopyranosyl-(1"-6')-2'-acetamido-2'-deoxy-beta-D-gluco pyranosyl]olean-12-en-28-oic acid [3], and new sulfated triterpene, echinocystic acid-3-O-sodium sulfate [4], have been isolated from the stem bark of Tetrapleura tetraptera. Compound 3 was 100% lethal to Biomphalaria glabrata at 20 ppm, while 4 was not molluscicidal at the same concentration. In a forward mutation assay utilizing Salmonella typhimurium strain TM677, T. tetraptera stem bark extracts were found to be mutagenic in the absence of a metabolic activating system (S-9). An MeOH extract of the fruit exhibited weak mutagenic activity only in the presence of S-9. The stem bark isolates, which included aridanin [1], 3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl)echinocystic acid [2], and compounds 3 and 4, were not mutagenic either with or without metabolic activation.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>8289059</pmid><doi>10.1021/np50101a002</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1993-11, Vol.56 (11), p.1872-1877 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_np50101a002 |
| source | American Chemical Society; MEDLINE |
| subjects | Animals Biomphalaria - drug effects BIOMPHALARIA GLABRATA Biotransformation DESARROLLO DE UN PRODUCTO DEVELOPPEMENT DE PRODUIT EXTRACTOS VEGETALES EXTRAIT D'ORIGINE VEGETALE Fabaceae - chemistry In Vitro Techniques LEGUMINOSAE Magnetic Resonance Spectroscopy MOLECULAR STRUCTURE Molluscacides - isolation & purification Molluscacides - pharmacokinetics Molluscacides - toxicity MOLLUSCICIDAL PROPERTIES MOLLUSCICIDE MOLLUSCICIDES MOLUSCOCIDAS MUTAGENE MUTAGENOS MUTAGENS Mutagens - isolation & purification Mutagens - pharmacokinetics Mutagens - toxicity NEW PRODUCTS Oleanolic Acid - analogs & derivatives Oleanolic Acid - isolation & purification Oleanolic Acid - pharmacokinetics Oleanolic Acid - toxicity PLANT EXTRACTS Plant Extracts - toxicity Plants, Medicinal PRODUCT DEVELOPMENT Rats Salmonella typhimurium - genetics Spectrophotometry, Infrared STRUCTURE TOXICIDAD TOXICITE TOXICITY TRITERPENOIDE TRITERPENOIDOS TRITERPENOIDS X-Ray Diffraction |
| title | Isolation of Echinocystic Acid-3-O-Sulfate, a New Triterpene, from Tetrapleura tetraptera, and Evaluation of the Mutagenic Potential of Molluscicidal Extracts and Isolates |
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