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Hobartine: a tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
Author(s) -
Paz Robles Cristian,
Badilla Vidal Natalia,
Suarez Sebastián,
Baggio Ricardo
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s205322961402258x
Subject(s) - indole alkaloid , indole test , chemistry , stereochemistry , hydrogen bond , double bond , crystallography , molecule , organic chemistry
The natural compound hobartine {systematic name: (1 R )‐3‐[(1 S ,5 S )‐(4,4,8‐trimethylbicyclo[3.3.1]non‐7‐en‐2‐yl)methyl]‐2,3‐dihydro‐1 H ‐indole}, C 20 H 26 N 2 , (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), C 69 , 1509–1512] and Watson et al. [ Acta Cryst. (1989), C 45 , 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.