Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivatives
<abstract language="eng">Mixtures of α-Santonin and various solvents were irradiated by either high or low pressure mercury lamps. The photochemical reactions afforded lumisantonin (11) (76% in acetonitrile), (3S,3aS,9bS)-3,6,6-trimethyl-3,3a,4,5-tetrahydronafto[1,2-b]furan-...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2009-01-01
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| Series: | Química Nova |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422009000200025 |
| _version_ | 1818050758360170496 |
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| author | Elson S. Alvarenga Luiz C. A. Barbosa William A. Saliba Francisco F. P. Arantes Antônio J. Demuner Antônio A. Silva |
| author_facet | Elson S. Alvarenga Luiz C. A. Barbosa William A. Saliba Francisco F. P. Arantes Antônio J. Demuner Antônio A. Silva |
| author_sort | Elson S. Alvarenga |
| collection | DOAJ |
| description | <abstract language="eng">Mixtures of α-Santonin and various solvents were irradiated by either high or low pressure mercury lamps. The photochemical reactions afforded lumisantonin (11) (76% in acetonitrile), (3S,3aS,9bS)-3,6,6-trimethyl-3,3a,4,5-tetrahydronafto[1,2-b]furan-2,7(6H,9bH)dione (12) (100% in acetonitrile), 10α-acetoxy-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olide (8) (26% in acetic acid), 10α-hydroxy-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olide (10) (32%) and (E)-3-((3S,3aS,7aS)-3-methyl-2-oxo-6-(propan-2-ylidene)hexahydrobenzofuran-7-(7aH)-ylidene)propanoic acid (9) (44%) (in water/ acetic acid 1:1, v/v). Lactone 12 was also prepared by irradiation of lumisantonin in diethyl ether. Lactones 8 and 10 were converted, respectively, into the 10α-acetoxy-3β-hydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (13) (87%) and 3β,10α-dihydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (14) (75%) by sodium borohydride reduction. The effects of the compounds on the development of radicle of Sorghum bicolor and Cucumis sativus were evaluated. |
| first_indexed | 2024-12-10T10:58:34Z |
| format | Article |
| id | doaj.art-48839e0ce81947a798c7d1309c1270f2 |
| institution | Directory Open Access Journal |
| issn | 0100-4042 1678-7064 |
| language | English |
| last_indexed | 2024-12-10T10:58:34Z |
| publishDate | 2009-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Química Nova |
| spelling | doaj.art-48839e0ce81947a798c7d1309c1270f22022-12-22T01:51:47ZengSociedade Brasileira de QuímicaQuímica Nova0100-40421678-70642009-01-0132240140610.1590/S0100-40422009000200025Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivativesElson S. AlvarengaLuiz C. A. BarbosaWilliam A. SalibaFrancisco F. P. ArantesAntônio J. DemunerAntônio A. Silva<abstract language="eng">Mixtures of α-Santonin and various solvents were irradiated by either high or low pressure mercury lamps. The photochemical reactions afforded lumisantonin (11) (76% in acetonitrile), (3S,3aS,9bS)-3,6,6-trimethyl-3,3a,4,5-tetrahydronafto[1,2-b]furan-2,7(6H,9bH)dione (12) (100% in acetonitrile), 10α-acetoxy-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olide (8) (26% in acetic acid), 10α-hydroxy-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olide (10) (32%) and (E)-3-((3S,3aS,7aS)-3-methyl-2-oxo-6-(propan-2-ylidene)hexahydrobenzofuran-7-(7aH)-ylidene)propanoic acid (9) (44%) (in water/ acetic acid 1:1, v/v). Lactone 12 was also prepared by irradiation of lumisantonin in diethyl ether. Lactones 8 and 10 were converted, respectively, into the 10α-acetoxy-3β-hydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (13) (87%) and 3β,10α-dihydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (14) (75%) by sodium borohydride reduction. The effects of the compounds on the development of radicle of Sorghum bicolor and Cucumis sativus were evaluated.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422009000200025α-santoninphotochemistryherbicide |
| spellingShingle | Elson S. Alvarenga Luiz C. A. Barbosa William A. Saliba Francisco F. P. Arantes Antônio J. Demuner Antônio A. Silva Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivatives Química Nova α-santonin photochemistry herbicide |
| title | Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivatives |
| title_full | Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivatives |
| title_fullStr | Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivatives |
| title_full_unstemmed | Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivatives |
| title_short | Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina Synthesis and evaluation of the phytotoxic activity of α-Santonin derivatives |
| title_sort | sintese e avaliacao da atividade fitotoxica de derivados da 945 santonina synthesis and evaluation of the phytotoxic activity of 945 santonin derivatives |
| topic | α-santonin photochemistry herbicide |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422009000200025 |
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