A new indole alkaloid from Aristotelia chilensis

Watson, William H.; Nagl, Ante; Silva, M.; Cespedes‐Acuña, Carlos L.; Jakupovic, Jasmin

doi:10.1107/s0108270189001150

Cited by 13 publications

(9 citation statements)

References 3 publications

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“…A perhaps related issue concerns the delocalization of the terminal C-CH 3 $ C CH 2 bond. As previously stated, Watson et al (1989) differentiated the isomeric forms (Ia) and (Ib) by their NMR results, ascribing to (Ia) a double bond at C5 C20 [1.344 (8) Å ] and a single bond at C5-C16 [1.419 (9) Å ]. Unfortunately, no crystal data for (Ib) are available to confirm this difference by crystallographic means.…”

Section: Figurementioning

confidence: 84%

“…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. Both forms [hereinafter (Ia) and (Ib)] were characterized by NMR, and the results showed that the main difference resided in a double bond being either exo-or endocyclic (see Scheme, encircled regions).…”

Section: Introductionmentioning

confidence: 99%

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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: Figurementioning

confidence: 84%

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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“…Initial studies [16,17] indicated the presence of indole alkaloids (aristotelinone, makonine, 8-oxo-9-dehydrohobartine and 8-oxo-9-dehydromakomakine) that were elucidated by high field NMR spectroscopy. In successive studies, these findings were complemented with the isolation of a quinoline alkaloid, the coumarin scopoletin [18] and other indole alkaloids such as makomakine, hobartine and serratoline [19].…”

Section: Maqui Leavesmentioning

confidence: 99%

The powerful colour of the maqui (Aristotelia chilensis [Mol.] Stuntz) fruit

Fredes

Robert

2014

JBR

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Abstract. Over the past 10 years, the research interest on maqui has increased due to the potential health benefits of the fruit, which are largely attributed to the high anthocyanin content and high antioxidant capacity. Furthermore, maqui fruit has earned the name of 'superfruit', and several products based on the dehydrated fruit and maqui juice are available on the international market. Although the maqui fruit is not frequently consumed by the Chilean population from urban areas, its use is deeply rooted in rural and native cultures (Mapuche and Huilliche). This review summarises the validation of the traditional uses of maqui and new evidence highlighting the principal role of anthocyanins in the antioxidant, anti-inflammatory and anti-diabetic activity of maqui fruit. The identification of a particular anthocyanin (delphinidin-3-glucoside-5-sambubioside) in maqui fruit and its anti-diabetic effect in in vivo models, in addition to its presence at higher concentrations in some maqui genotypes, encourages investigation into maqui genotypes that may have higher contents of particular anthocyanins. However, information concerning maqui domestication is still deficient.

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“…However, there are certain representatives within this family that cannot be approached by proper modification of the monoterpinylamine building block, but require oxidative modifications at the indole alkaloid level. In the case of 79, the structure proposal, based on spectroscopic arguments, was secured by a single-crystal X-ray analysis [49]. The two formal dehydration products 78 and 79 were isolated from A. chilensis and were shown to display the same characteristic UV spectra as 77 [49,50].…”

Section: Aristotelia Alkaloidsmentioning

confidence: 99%

“…A retrosynthetic analysis of this allo-series leads from aristolasicone (47) to alloserratenone (48) (Scheme 8) and thence to the known building block 41 and to indoleprotected 2-indolylacetaldehyde (49). The actual synthesis of racemic 47 was straightforward and the target was assembled in 4 steps from 41 and 49 with an overall yield of 50% [26].…”

Section: Aristotelia Alkaloidsmentioning

confidence: 99%

New Strategies for the Synthesis of Monoterpene Indole Alkaloids

Borschberg

2005

COC

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The synthetic efforts of the author's research team in several areas within the monoterpene indole alkaloid family are summarized. Most of the work was accomplished in the field of the Aristotelia alkaloids, where some 25 natural products were synthesized for the first time. Systematic investigations on the oxidative rearrangement of indoles to oxindoles and pseudoindoxyl derivatives led to control over the chemoselectivity and stereoselectivity of this process, which served for enantioselective preparations of the simple alkaloids horsfiline and elacomine. In addition, recent developments in a novel approach to Iboga alkaloids containing a hydroxyl group at C(19) are presented. The key steps involved a self-immolating 1,4-chirality transfer in an Ireland-Claisen rearrangement and an intramolecular nitrone-olefin [2+3]-cycloaddition to give the aliphatic isoquinuclidine core of the target molecules. The first synthesis of (19R)hydroxyibogamine was completed by grafting a 3-ethylindole unit onto the aliphatic nitrogen, followed by closing the 7membered ring.

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A new indole alkaloid from Aristotelia chilensis

Cited by 13 publications

References 3 publications

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)

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)

The powerful colour of the maqui (Aristotelia chilensis [Mol.] Stuntz) fruit

New Strategies for the Synthesis of Monoterpene Indole Alkaloids

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