Chilocorine: heptacyclic alkaloid from a coccinellid beetle
A novel heptacyclic alkaloid, for which we coin the name chilocorine, was isolated from a ladybird beetle, Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro- 9b-azaphenalene and 3,4-dimethyloctahydro- 8b-azaacenaphthylene. The proposed structure is...
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| Published in | Tetrahedron Vol. 50; no. 8; pp. 2365 - 2372 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
21.02.1994
Elsevier |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0040-4020 1464-5416 |
| DOI | 10.1016/S0040-4020(01)86955-6 |
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| Abstract | A novel heptacyclic alkaloid, for which we coin the name
chilocorine, was isolated from a ladybird beetle,
Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro-
9b-azaphenalene and 3,4-dimethyloctahydro-
8b-azaacenaphthylene. The proposed structure is based on mass spectrometric, ultraviolet spectroscopic, and NMR evidence.
Chilocorine, a novel heptacyclic alkaloid, was isolated from a ladybird beetle,
Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro-9
b-azaphenalene and 3,4-dimethyloctahydro-8
b-azaacenaphthylene. |
|---|---|
| AbstractList | A novel heptacyclic alkaloid, for which we coin the name
chilocorine, was isolated from a ladybird beetle,
Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro-
9b-azaphenalene and 3,4-dimethyloctahydro-
8b-azaacenaphthylene. The proposed structure is based on mass spectrometric, ultraviolet spectroscopic, and NMR evidence.
Chilocorine, a novel heptacyclic alkaloid, was isolated from a ladybird beetle,
Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro-9
b-azaphenalene and 3,4-dimethyloctahydro-8
b-azaacenaphthylene. A novel heptacyclic alkaloid, for which we coin the name chilocorine, was isolated from a ladybird beetle, Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro-9b-azaphenalene and 3,4-dimethyloctahydro-8b-azaacenaphthyle The proposed structure is based on mass spectrometric, ultraviolet spectroscopic, and NMR evidence. |
| Author | Attygalle, Athula B. Houck, Marilyn A. Meinwald, Jerrold Svatoš, Aleš McCormick, Kevin D. Xu, Shang-Cheng Blankespoor, Curtis L. Eisner, Thomas |
| Author_xml | – sequence: 1 givenname: Kevin D. surname: McCormick fullname: McCormick, Kevin D. – sequence: 2 givenname: Athula B. surname: Attygalle fullname: Attygalle, Athula B. – sequence: 3 givenname: Shang-Cheng surname: Xu fullname: Xu, Shang-Cheng – sequence: 4 givenname: Aleš surname: Svatoš fullname: Svatoš, Aleš – sequence: 5 givenname: Jerrold surname: Meinwald fullname: Meinwald, Jerrold – sequence: 6 givenname: Marilyn A. surname: Houck fullname: Houck, Marilyn A. organization: Department of Biological Sciences, Texas Tech University, Lubbock, Texas 79404 U.S.A – sequence: 7 givenname: Curtis L. surname: Blankespoor fullname: Blankespoor, Curtis L. – sequence: 8 givenname: Thomas surname: Eisner fullname: Eisner, Thomas |
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| Cites_doi | 10.1016/0040-4020(93)80019-P 10.1126/science.134.3475.329 10.1016/0040-4020(75)87008-6 10.3987/S-1977-01-0685 10.1007/BF01952471 10.1071/CH9821255 10.1146/annurev.en.36.010191.003143 10.1021/jo00186a029 10.1007/BF01966179 10.1016/S0040-4039(01)95617-5 10.1073/pnas.90.11.5204 10.1002/bscb.19850940809 10.1139/v76-256 10.1016/S0040-4039(00)91601-0 |
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| Keywords | (Z)-1,17-DIAMINOOCTADEC-9-ENE COLEOPTERA ALIPHATIC DIAMINE Alkaloid Coccinellidae Molecular structure Coleoptera Angular nitrogen heterocycle Arthropoda Insecta Polycyclic compound Isolation Invertebrata NMR spectrum |
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| References | Brown, Moore (BIB9) 1982; 35 Gordon (BIB15) 1985; 93 Timmermans, Braekman, Daloze, Pasteels, Merlin, Declercq (BIB14) 1992; 33 Mueller, Thompson, DiPardo (BIB19) 1984; 49 Happ, Eisner (BIB17) 1961; 134 Tursch, Daloze, Hootele (BIB18) 1972; 26 Ayer, Bennett, Browne, Purdham (BIB11) 1976; 54 Braconnier, Braekman, Daloze, Pasteels (BIB4) 1985; 41 Eisner, Goetz, Aneshansley, Ferstandig-Arnold, Meinwald (BIB7) 1986; 42 Braconnier, Braekman, Daloze (BIB5) 1985; 94 Attygalle, Xu, McCormick, Meinwald, Blankespoor, Eisner (BIB6) 1993; 49 Attygalle, McCormick, Blankespoor, Eisner, Meinwald (BIB13) 1993; 90 Tursch, Braekman, Daloze, Hootele, Losman, Karlsson, Pasteels (BIB8) 1973 Ayer, Browne (BIB12) 1977; 7 Tursch, Daloze, Braekman, Hootele, Pasteels (BIB10) 1975 Houck, OConnor (BIB16) 1991; 36 Mueller (10.1016/S0040-4020(01)86955-6_BIB19) 1984; 49 Tursch (10.1016/S0040-4020(01)86955-6_BIB8) 1973 Braconnier (10.1016/S0040-4020(01)86955-6_BIB5) 1985; 94 Houck (10.1016/S0040-4020(01)86955-6_BIB16) 1991; 36 Tursch (10.1016/S0040-4020(01)86955-6_BIB18) 1972; 26 Attygalle (10.1016/S0040-4020(01)86955-6_BIB6) 1993; 49 Ayer (10.1016/S0040-4020(01)86955-6_BIB12) 1977; 7 Brown (10.1016/S0040-4020(01)86955-6_BIB9) 1982; 35 Eisner (10.1016/S0040-4020(01)86955-6_BIB7) 1986; 42 Attygalle (10.1016/S0040-4020(01)86955-6_BIB13) 1993; 90 Tursch (10.1016/S0040-4020(01)86955-6_BIB10) 1975 Timmermans (10.1016/S0040-4020(01)86955-6_BIB14) 1992; 33 Braconnier (10.1016/S0040-4020(01)86955-6_BIB4) 1985; 41 Ayer (10.1016/S0040-4020(01)86955-6_BIB11) 1976; 54 Gordon (10.1016/S0040-4020(01)86955-6_BIB15) 1985; 93 Happ (10.1016/S0040-4020(01)86955-6_BIB17) 1961; 134 ATTYGALLE AB (WOS:A1994MW95800003.2) 1993; 90 GORDON, RD (WOS:A1985AHD5700001) 1985; 93 TURSCH, B (WOS:A1975AH18400008) 1975; 31 EISNER, T (WOS:A1986A476100046) 1986; 42 HOUCK, MA (WOS:A1991EQ80700026) 1991; 36 MUELLER, RH (WOS:A1984SW65900029) 1984; 49 BRACONNIER, MF (WOS:A1985ATU4500008) 1985; 94 BRACONNIER, MF (WOS:A1985AGJ6700040) 1985; 41 BROWN, WV (WOS:A1982NU72100021) 1982; 35 TIMMERMANS, M (WOS:A1992HH25200008) 1992; 33 ATTYGALLE, AB (WOS:A1993MB07600018) 1993; 49 AYER, WA (WOS:A1976BU46100021) 1976; 54 HAPP, GM (WOS:A19612982C00051) 1961; 134 TURSCH, B (WOS:A1973O503600009) 1973 AYER, WA (WOS:A1977DZ30900061) 1977; 7 TURSCH, B (WOS:A1972L687400005) 1972; 26 |
| References_xml | – volume: 26 start-page: 74 year: 1972 end-page: 75 ident: BIB18 publication-title: Chimia – start-page: 201 year: 1973 end-page: 202 ident: BIB8 publication-title: Tetrahedron Lett. – volume: 35 start-page: 1255 year: 1982 end-page: 1261 ident: BIB9 publication-title: Aust. J. Chem. – volume: 93 start-page: 1 year: 1985 end-page: 912 ident: BIB15 publication-title: J. N. Y. Entomol. 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| Snippet | A novel heptacyclic alkaloid, for which we coin the name
chilocorine, was isolated from a ladybird beetle,
Chilocorus cacti. It has a unique structure made up... A novel heptacyclic alkaloid, for which we coin the name chilocorine, was isolated from a ladybird beetle, Chilocorus cacti. It has a unique structure made up... |
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| StartPage | 2365 |
| SubjectTerms | Alcaloids Analytical, structural and metabolic biochemistry Biological and medical sciences Chemistry Chemistry, Organic Fundamental and applied biological sciences. Psychology Heterocyclic compounds, pigments Other biological molecules Physical Sciences Science & Technology |
| Title | Chilocorine: heptacyclic alkaloid from a coccinellid beetle |
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