The natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N - H⋯N hydrogen bond which is the only significant intermolecular interaction present in the structure. © 2014 International Union of Crystallography.
Documento: | Artículo |
Título: | Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui) |
Autor: | Paz Robles, C.; Badilla Vidal, N.; Suarez, S.; Baggio, R. |
Filiación: | Departamento de Ciencias Químicas y Recursos Naturales, Facultad de Ingeniería, Universidad de la Frontera, Temuco, Chile Departamento de Química Inorgánica Analítica y Química, Física/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina Gerencia de Investigación y Aplicaciones, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina |
Palabras clave: | alkaloid; Aristotelia chilensis; Chilean flora metabolites; crystal structure; hobartine; maqui; natural products; tetracyclic compound; Alkaloids; Hydrogen bonds; Metabolites; Polycyclic aromatic hydrocarbons; Aristotelia chilensis; hobartine; maqui; Natural products; tetracyclic compound; Crystal structure; Aristotelia chilensis; biological product; hobartine; indole alkaloid; chemical structure; chemistry; hydrogen bond; isolation and purification; metabolism; synthesis; X ray crystallography; Biological Products; Crystallography, X-Ray; Hydrogen Bonding; Indole Alkaloids; Molecular Structure |
Año: | 2014 |
Volumen: | 70 |
Página de inicio: | 1075 |
Página de fin: | 1078 |
DOI: | http://dx.doi.org/10.1107/S205322961402258X |
Título revista: | Acta Crystallographica Section C: Structural Chemistry |
Título revista abreviado: | Acta crystallogr., C Struct. Chem. |
ISSN: | 20532296 |
CODEN: | ACSCG |
CAS: | Biological Products; hobartine; Indole Alkaloids |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20532296_v70_n_p1075_PazRobles |