Alkaloids from Psychotria oleoides with Activity on Growth Hormone Release

Psychotria genus (Rubiaceae) is featured into the angiosperm, being the most speciose genus comprising approximately 1600 species. The available references demonstrate that Psychotria has several uses on traditional medicine including spiritual and cultural purposes, and presents great potential on pharmacological properties, especially the one related to neurodegenerative diseases. Despite its wide biological properties, this genus has shown complex phylogenetic analysis due to lack of chemotaxonomic information. In recent years, the interest in these plants has increased considerably and many active compounds have been isolated. Phytochemical investigations described in the literature confirmed the indole alkaloids as the major compounds and besides that, another particular chemical constituent are cyclic peptides, known as cyclotides. This present review will cover the relevant literature from 1962 until 2015, and outlines the current data on taxonomy, chemotaxonomy, traditional uses, pharmacological properties, chemical composition and ecological approach from Psychotria genus.

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“…49 The extract from leaves and roots of P. stachyoides Benth. provided β-sitosterol (71) and stigmasterol glucosides (72) (Figure 4). 12 …”

Section: Terpenoidsmentioning

confidence: 99%

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Calixto¹,

Pinto²,

Ramalho³

et al. 2016

Journal of the Brazilian Chemical Society

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“…[24,25] It is also widely found within members of the Psychotria genera. [15,17,[26][27][28] A diastereomeric natural product, hodgkinsine B (11), [29] whose exact structure was only recently elucidated (see Section 6), [30] has contiguous quaternary stereocenters of opposite absolute configuration ( Figure 6). Hodgkinsine and hodgkinsine B are derived from the appendage of a cis-pyrrolidino [2,3-b]indoline subunit of R configuration at C3a to the enantiotopic peri positions 7 or 7' of meso-chimonanthine.…”

Section: Introductionmentioning

confidence: 99%

“…Quadrigemine C and psycholeine were co-isolated from Psychotria oleoides, [26,28,33,34] and were the first non-peptidic inhibitors of somatostatin to be reported.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

2007

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Our ability to access the more complex members of the cyclotryptamine family of alkaloids, and to exploit their disparate biological activities, is limited by the synthetic challenge posed by their oligomeric, polyindoline structures. A recurring structural theme within these molecules is the presence of multiple quaternary stereocenters in close proximity to one another. Over the last decade, we have developed a set of transformations that allow rapid access to polyindolines, a number of which exploit the ability of catalytic levels of palladium to orchestrate carbon-carbon bond formation with impressive levels of regio- and stereocontrol. This review tells the story behind the development of this toolbox of synthetic methods, and their validation through the total synthesis of a number of structurally complex cyclotryptamine alkaloids. It also highlights an aspect of asymmetric catalysis that has received little attention, the ability of catalytic asymmetric reactions to selectively elaborate complex, polyfunctional molecules.

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“…The hydroxypyrroloindoline gypsetin has evoked interest as a potential inhibitor of the enzyme acyl-CoA:cholesterol acyltransferase and as such might find therapeutic use as a cholesterol-lowering agent (10)(11)(12). Psycholeine and quadrigemine C have been documented as the first nonpeptide antagonists of the somatostatin family of receptors (13). Several other polyindolines in this natural product family have also been shown to exhibit significant biological properties (13,.…”

mentioning

confidence: 99%

“…Psycholeine and quadrigemine C have been documented as the first nonpeptide antagonists of the somatostatin family of receptors (13). Several other polyindolines in this natural product family have also been shown to exhibit significant biological properties (13,.…”

mentioning

confidence: 99%

Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B

Austin

Kim

Sinz

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

442

117

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Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with ␣,␤-unsaturated aldehydes in the presence of imidazolidinone catalysts 1 and 8 provides pyrroloindoline adducts in high yield and excellent enantioselectivities. This transformation is successful for a wide range of tryptamine and ␣,␤-unsaturated aldehyde substrates. This amine-catalyzed sequence has been extended to the enantioselective construction of furanoindoline frameworks. Application of this pyrroloindoline-forming reaction to natural product synthesis has been accomplished in the context of the enantioselective synthesis of (؊)-flustramine B.

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Alkaloids from Psychotria oleoides with Activity on Growth Hormone Release

Cited by 59 publications

References 8 publications

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Total Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters

Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B

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