Isolation and Structure of a 20,21-Epoxybufenolide Series from “Ch'an Su”
Steroid bufenolides resulting from epoxidation of the 17β-2-pyrone ring of bufadienolides are rare. Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2002-07, Vol.65 (7), p.1001-1005 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Kamano, Yoshiaki Nogawa, Toshihiko Yamashita, Ayano Hayashi, Masahiko Inoue, Masuo Drašar, Pavel Pettit, George R |
| description | Steroid bufenolides resulting from epoxidation of the 17β-2-pyrone ring of bufadienolides are rare. Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-epoxyresibufogenin (5), were isolated from the Chinese toad skin extract drug Ch'an Su. The structures were elucidated by spectroscopic and chemical methods. The configuration at C-20 was assigned by the analysis of difference NOE spectra. The cancer cell (KB and MH-60) growth inhibition by the new 20,21-epoxybufenolides was examined, and 20,21-epoxides 1, 2, and 5 were found to significantly inhibit the leukemia MH-60 cell line. |
| doi_str_mv | 10.1021/np0200360 |
| format | Article |
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Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-epoxyresibufogenin (5), were isolated from the Chinese toad skin extract drug Ch'an Su. The structures were elucidated by spectroscopic and chemical methods. The configuration at C-20 was assigned by the analysis of difference NOE spectra. The cancer cell (KB and MH-60) growth inhibition by the new 20,21-epoxybufenolides was examined, and 20,21-epoxides 1, 2, and 5 were found to significantly inhibit the leukemia MH-60 cell line.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np0200360</identifier><identifier>PMID: 12141860</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Bufanolides - chemistry ; Bufanolides - isolation & purification ; Bufanolides - pharmacology ; Bufonidae ; Chromatography, High Pressure Liquid ; Chromatography, Thin Layer ; Drug Screening Assays, Antitumor ; Epoxy Compounds - chemistry ; Epoxy Compounds - isolation & purification ; Epoxy Compounds - pharmacology ; General pharmacology ; HL-60 Cells - drug effects ; Humans ; KB Cells - drug effects ; Leukemia, Myeloid ; Magnetic Resonance Spectroscopy ; Medical sciences ; Medicine, Chinese Traditional ; Mice ; Molecular Conformation ; Molecular Structure ; Nasopharyngeal Neoplasms ; Pharmacognosy. 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Drug treatments ; Skin - metabolism ; Spectrophotometry, Infrared ; Stereoisomerism ; Tumor Cells, Cultured - drug effects</subject><ispartof>Journal of natural products (Washington, D.C.), 2002-07, Vol.65 (7), p.1001-1005</ispartof><rights>Copyright © 2002 American Chemical Society and American Society of Pharmacognosy</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-f577a01bbb794681a437d835419f19e1ee4b0036c4f6d31bc1e8580e85d5f0513</citedby><cites>FETCH-LOGICAL-a445t-f577a01bbb794681a437d835419f19e1ee4b0036c4f6d31bc1e8580e85d5f0513</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np0200360$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np0200360$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13826489$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12141860$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kamano, Yoshiaki</creatorcontrib><creatorcontrib>Nogawa, Toshihiko</creatorcontrib><creatorcontrib>Yamashita, Ayano</creatorcontrib><creatorcontrib>Hayashi, Masahiko</creatorcontrib><creatorcontrib>Inoue, Masuo</creatorcontrib><creatorcontrib>Drašar, Pavel</creatorcontrib><creatorcontrib>Pettit, George R</creatorcontrib><title>Isolation and Structure of a 20,21-Epoxybufenolide Series from “Ch'an Su”</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Steroid bufenolides resulting from epoxidation of the 17β-2-pyrone ring of bufadienolides are rare. Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-epoxyresibufogenin (5), were isolated from the Chinese toad skin extract drug Ch'an Su. The structures were elucidated by spectroscopic and chemical methods. The configuration at C-20 was assigned by the analysis of difference NOE spectra. The cancer cell (KB and MH-60) growth inhibition by the new 20,21-epoxybufenolides was examined, and 20,21-epoxides 1, 2, and 5 were found to significantly inhibit the leukemia MH-60 cell line.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Bufanolides - chemistry</subject><subject>Bufanolides - isolation & purification</subject><subject>Bufanolides - pharmacology</subject><subject>Bufonidae</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Chromatography, Thin Layer</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Epoxy Compounds - chemistry</subject><subject>Epoxy Compounds - isolation & purification</subject><subject>Epoxy Compounds - pharmacology</subject><subject>General pharmacology</subject><subject>HL-60 Cells - drug effects</subject><subject>Humans</subject><subject>KB Cells - drug effects</subject><subject>Leukemia, Myeloid</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Medicine, Chinese Traditional</subject><subject>Mice</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Nasopharyngeal Neoplasms</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Skin - metabolism</subject><subject>Spectrophotometry, Infrared</subject><subject>Stereoisomerism</subject><subject>Tumor Cells, Cultured - drug effects</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtO3DAUBmCrKioDdNEXqLwpCInQc3xLskSj4SKoOtJMpe4sJ7FFIBMPdiLBbh4EXo4nIWhGzIaNz8Kffp3zE_ID4RSB4e92CQyAK_hCRigZJAqY_EpGgIonPFNil-zFeAeDgVx-I7vIUGCmYET-XEXfmK72LTVtRWdd6MuuD5Z6Rw1lcMIwmSz941PRO9v6pq4sndlQ20hd8Av6unoe3x6Zls7619XLAdlxpon2-2buk3_nk_n4Mrn5e3E1PrtJjBCyS5xMUwNYFEWaC5WhETytMi4F5g5zi9aK4v2eUjhVcSxKtJnMYHgq6UAi3yeH69xl8A-9jZ1e1LG0TWNa6_uoU8ylGDoY4PEalsHHGKzTy1AvTHjSCPq9O_3R3WB_bkL7YmGrrdyUNYBfG2BiaRoXTFvWcet4xpTI8sEla1fHzj5-_Jtwr1XKU6nn05k-v0YG4_9Tzbe5poz6zvehHbr7ZME3ReSPuA</recordid><startdate>20020701</startdate><enddate>20020701</enddate><creator>Kamano, Yoshiaki</creator><creator>Nogawa, Toshihiko</creator><creator>Yamashita, Ayano</creator><creator>Hayashi, Masahiko</creator><creator>Inoue, Masuo</creator><creator>Drašar, Pavel</creator><creator>Pettit, George R</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>BSCLL</scope><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>20020701</creationdate><title>Isolation and Structure of a 20,21-Epoxybufenolide Series from “Ch'an Su”</title><author>Kamano, Yoshiaki ; Nogawa, Toshihiko ; Yamashita, Ayano ; Hayashi, Masahiko ; Inoue, Masuo ; Drašar, Pavel ; Pettit, George R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-f577a01bbb794681a437d835419f19e1ee4b0036c4f6d31bc1e8580e85d5f0513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Bufanolides - chemistry</topic><topic>Bufanolides - isolation & purification</topic><topic>Bufanolides - pharmacology</topic><topic>Bufonidae</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Chromatography, Thin Layer</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Epoxy Compounds - chemistry</topic><topic>Epoxy Compounds - isolation & purification</topic><topic>Epoxy Compounds - pharmacology</topic><topic>General pharmacology</topic><topic>HL-60 Cells - drug effects</topic><topic>Humans</topic><topic>KB Cells - drug effects</topic><topic>Leukemia, Myeloid</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Medicine, Chinese Traditional</topic><topic>Mice</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Nasopharyngeal Neoplasms</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Skin - metabolism</topic><topic>Spectrophotometry, Infrared</topic><topic>Stereoisomerism</topic><topic>Tumor Cells, Cultured - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamano, Yoshiaki</creatorcontrib><creatorcontrib>Nogawa, Toshihiko</creatorcontrib><creatorcontrib>Yamashita, Ayano</creatorcontrib><creatorcontrib>Hayashi, Masahiko</creatorcontrib><creatorcontrib>Inoue, Masuo</creatorcontrib><creatorcontrib>Drašar, Pavel</creatorcontrib><creatorcontrib>Pettit, George R</creatorcontrib><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><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kamano, Yoshiaki</au><au>Nogawa, Toshihiko</au><au>Yamashita, Ayano</au><au>Hayashi, Masahiko</au><au>Inoue, Masuo</au><au>Drašar, Pavel</au><au>Pettit, George R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation and Structure of a 20,21-Epoxybufenolide Series from “Ch'an Su”</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2002-07-01</date><risdate>2002</risdate><volume>65</volume><issue>7</issue><spage>1001</spage><epage>1005</epage><pages>1001-1005</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Steroid bufenolides resulting from epoxidation of the 17β-2-pyrone ring of bufadienolides are rare. Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-epoxyresibufogenin (5), were isolated from the Chinese toad skin extract drug Ch'an Su. The structures were elucidated by spectroscopic and chemical methods. The configuration at C-20 was assigned by the analysis of difference NOE spectra. The cancer cell (KB and MH-60) growth inhibition by the new 20,21-epoxybufenolides was examined, and 20,21-epoxides 1, 2, and 5 were found to significantly inhibit the leukemia MH-60 cell line.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>12141860</pmid><doi>10.1021/np0200360</doi><tpages>5</tpages></addata></record> |
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| subjects | Animals Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Biological and medical sciences Bufanolides - chemistry Bufanolides - isolation & purification Bufanolides - pharmacology Bufonidae Chromatography, High Pressure Liquid Chromatography, Thin Layer Drug Screening Assays, Antitumor Epoxy Compounds - chemistry Epoxy Compounds - isolation & purification Epoxy Compounds - pharmacology General pharmacology HL-60 Cells - drug effects Humans KB Cells - drug effects Leukemia, Myeloid Magnetic Resonance Spectroscopy Medical sciences Medicine, Chinese Traditional Mice Molecular Conformation Molecular Structure Nasopharyngeal Neoplasms Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Skin - metabolism Spectrophotometry, Infrared Stereoisomerism Tumor Cells, Cultured - drug effects |
| title | Isolation and Structure of a 20,21-Epoxybufenolide Series from “Ch'an Su” |
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