Tetracyclic Triterpenoids from the Leaves of Azadirachta indica and Their Insecticidal Activities
A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6α-O-methyl, 7α-senecioyl(7-deacetyl)-11α,12α,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the kno...
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| Published in | Chemical & pharmaceutical bulletin Vol. 51; no. 4; pp. 415 - 417 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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TOKYO
The Pharmaceutical Society of Japan
01.04.2003
Pharmaceutical Soc Japan Maruzen Japan Science and Technology Agency |
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| Abstract | A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6α-O-methyl, 7α-senecioyl(7-deacetyl)-11α,12α,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC50 values of 16 and 154 ppm, respectively. |
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| AbstractList | A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6α-O-methyl, 7α-senecioyl(7-deacetyl)-11α,12α,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC50 values of 16 and 154 ppm, respectively. A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6 alpha -O-methyl, 7 alpha -senecioyl(7-deacetyl)-11 alpha ,12 alpha ,21,23-tetrahydroxy-21,23-epoxy- 2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC sub(50) values of 16 and 154 ppm, respectively. A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6alpha-O-methyl, 7alpha-senecioyl(7-deacetyl)-11alpha12alpha,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC50 values of 16 and 154 ppm, respectively. A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6alpha-O-methyl, 7alpha-senecioyl(7-deacetyl)-11alpha,12alpha,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC(50) values of 16 and 154 ppm, respectively. |
| Author | Siddiqui, Bina Shaheen Afshan, Farhana Tariq, Rajput Mohammad Sultana, Razia Naqvi, Syed Naeemul-Hassan Gulzar, Tahsin |
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| Cites_doi | 10.1055/s-2007-971670 10.1016/S0040-4020(01)98254-7 10.1039/a902326g 10.1093/jee/18.2.265a 10.1016/S0031-9422(99)00548-8 10.1016/S0040-4020(00)00244-1 10.1021/np50055a003 10.1016/S0031-9422(97)00826-1 10.1016/0040-4020(68)88105-0 10.1016/0031-9422(95)00471-I |
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| Keywords | triterpenoid TETRANORTRITERPENOIDS FRUIT COATS Anopheles stephensi BIOGENETIC INTEREST Azadirachta indica Meliaccae Steroid Insecticide Insecta Pesticide crop Acetal Anophles stephensi Dicotyledones Angiospermae Acylate Terpenoid Pesticides Plant leaf Meliaceae Biological activity Larva Arthropoda Culicidae Plant origin Triterpene Isolation Spermatophyta Invertebrata Enone Diptera Structural analysis |
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| SubjectTerms | Animals Anopheles stephensi Azadirachta Azadirachta indica Biological and medical sciences Chemical control Chemistry Chemistry, Medicinal Chemistry, Multidisciplinary Control Culicidae - drug effects Fundamental and applied biological sciences. Psychology Insecticides - chemistry Insecticides - isolation & purification Insecticides - pharmacology Life Sciences & Biomedicine Meliaceae Pharmacology & Pharmacy Physical Sciences Phytopathology. Animal pests. Plant and forest protection Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology Plant Leaves Protozoa. Invertebrates Science & Technology Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - pharmacology triterpenoid |
| Title | Tetracyclic Triterpenoids from the Leaves of Azadirachta indica and Their Insecticidal Activities |
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