New alkaloids from Aristotelia chilensis(Mol.) stuntz

Bittner, M.; Silva, Mario; Gopalakrishna, E. M.; Watson, William H.; Zabel, V.; Matlin, Stephen A.; Sammes, Peter G.

doi:10.1039/c39780000079

Cited by 21 publications

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“…Among others, a number of different indole alkaloids have been identified, some of them already known from other botanical species [viz. aristoteline, aristotelone (Bhakuni et al, 1976), aristotelinine, aristone (Bittner et al, 1978)] and others originally described from A. chilensis extracts. One of these latter alkaloids was 4,4-dimethyl-8-methylene-3-azabicyclo-[3.3.1]non-2-en-2-yl 3-indolyl ketone, structurally characterized by Watson et al (1989), where two isomers of this molecule were mentioned as isolated from A. chilensis.…”

Section: Introductionmentioning

confidence: 99%

A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en-2-yl 3-indolyl ketone, an indole alkaloid extracted fromAristotelia chilensis(maqui)

Paz¹,

Becerra²,

Silva³

et al. 2013

Acta Crystallogr C

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The title compound [systematic name: (4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone], C20H22N2O, (II), was obtained from mother liquors extracted from Aristotelia chilensis (commonly known as maqui), a native Chilean tree. The compound is a polymorphic form of that obtained from the same source and reported by Watson, Nagl, Silva, Cespedes & Jakupovic [Acta Cryst. (1989), C45, 1322-1324], (Ia). The molecule consists of an indolyl ketone fragment and a nested three-ring system, with both groups linked by a C-C bridge. Comparison of both forms shows that they do not differ in their gross features but in the relative orientation of the two ring systems, due to different rotations around the bridge, as measured by the O=C-C=N torsion angle [130.0 (7)° in (Ia) and 161.6 (2)° in (II)]. The resulting slight conformational differences are reflected in a number of intramolecular contacts being observed in (II) but not in (Ia). Regarding intermolecular interactions, both forms share a similar N-H···O synthon but with differing hydrogen-bonding strength, leading in both cases to C(6) catemers with different chain motifs. There are marked differences between the two forms regarding colour and the (de)localization of a double bond, which allows speculation about the possible existence of different variants of this type of molecule.

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Section: Introductionmentioning

confidence: 99%

A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en-2-yl 3-indolyl ketone, an indole alkaloid extracted fromAristotelia chilensis(maqui)

Paz¹,

Becerra²,

Silva³

et al. 2013

Acta Crystallogr C

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“…Maqui berries are a healthy fruit with high ORAC (Oxygen Radical Absorbance Capacity) antioxidant properties (Cé spedes et al, 2010). Indole alkaloids have been identified from extracts of maqui, examples being aristoteline, aristotelone (Bhakuni et al, 1976), aristotelinine and aristone (Bittner et al, 1978). Continuing our study of naturally occurring products from Chilean flora, we have isolated from Aristotelia chilensis the indole alkaloid hobartine, (I).…”

Section: Introductionmentioning

confidence: 93%

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

Robles

Vidal

Suárez

et al. 2014

Acta Crystallogr C Struct Chem

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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.

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“…Aristotelia serrata from New Zealand contains peduncularine (2), aristoteline (3) and several unidentified components (Anderson, Robertson, Avey, Donovan, Bick, Bremner, Finney, Preston, Gallagher & Russell, 1975). Aristotelia chilensis, collected in Chile, has yielded aristoteline (3), aristotelinine (4) (Gopalakrishna, Watson, Silva & Bittner, 1978), aristotelone (5) (Bhakuni, Silva, Matlin & Sammes, 1976), and aristone (6) (Bittner, Silva, Gopalakrishna, Watson, Zabel, Matlin & Sammes, 1978). Compound (6) was postulated to arise via rearrangement of a derivative of (4) (Zabel, Watson, Bittner & Silva, 1980).…”

Section: Introductionmentioning

confidence: 99%