Hobartine: a tetracyclic indole alkaloid extracted fromAristotelia chilensis(maqui)

Abstract

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.

A Comprehensive Literature Review on Cardioprotective Effects of Bioactive Compounds Present in Fruits of Aristotelia chilensis Stuntz (Maqui)

“…Only a few studies refer to the phytochemical analysis of leaf extracts of Maqui. The presence of indole and quinoline alkaloids has been reported in the leaves [ 19 ], being identified as aristoteline, serratoline, aristone, horbatinol, and horbatina [ 54 , 55 ]. Studies performed on ethanolic extracts of Maqui leaves reported the presence of some polyphenols such as gallic acid, coumaric acid, quercetin, myricetin, rutin, pelargonidin, and catechin.…”