N,β-d-Glucopyranosyl vincosamide, a light regulated indole alkaloid from the shoots of Psychotria leiocarpa

Henriques, Amélia T.; Lopes, S.O; Paranhos, Juçara Terezinha; Gregianini, Tatiana Schäffer; Poser, Gilsane Lino von; Fett-Neto, Arthur Germano; Schripsema, Jan

doi:10.1016/j.phytochem.2003.10.027

Cited by 56 publications

(38 citation statements)

References 23 publications

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“…was obtained the major indole alkaloid N,β-D-glucopyranosyl vincosamide (15). 62,98 Psychotriasine (16) was isolated from the leaves of P. calocarpa. This compound is the first example of a dimeric tryptamine-related alkaloid that contains a free N-methyltryptamine unit in the molecule.…”

Section: Alkaloidsmentioning

confidence: 99%

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The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Calixto¹,

Pinto²,

Ramalho³

et al. 2016

Journal of the Brazilian Chemical Society

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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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Section: Alkaloidsmentioning

confidence: 99%

“…The phytochemical study on P. yunnanensis allowed the isolation of four norisoprenoids (58-61) and one monoterpenic acid (62). From the aerial parts of this plant a new type of sesquiterpene derived from acorane, possessing rare spirobicyclic carbon skeleton, known as psycacoraone A, was identified (63).…”

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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“…Henriques et al [34] reported the isolation of N-b-D-glucopyranosyl vincosamide (28) from leaves of P. leiocarpa. It was the first report of an N-glycosylated monoterpenoid indole alkaloid.…”

Section: Monoterpene Indole Alkaloids Isolated From Psychotria Speciesmentioning

confidence: 99%

Psychotria Genus

Carvalho

Braz‐Filho

et al. 2016

Studies in Natural Products Chemistry

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“…Neotropical species, belonging to the subgenus Heteropsychotria, have been subjected to chemical and pharmacological investigations, revealing the presence of bioactive glucosidic monotepene indole alkaloids (MIAs) [8][9][10][11][12][13][14]. Psychollatine, the major MIA isolated from Psychotria umbellata Vell., exhibited mild analgesic effects against a number of algogenic stimuli [15], anxiolytic (7.5 and 15 mg/kg) and antidepressant effects (3 and 7.5 mg/kg) in mice models [16,17].…”

Section: Introductionmentioning

confidence: 99%

Strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae), decreases serotonin levels in rat hippocampus

et al. 2012

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Psychotria is a complex genus whose neotropical species are known by the presence of glucosidic monoterpene indole alkaloids. These compounds are able to display a large range of effects on the central nervous system, such as anxiolytic, antidepressant, analgesic, and impairment of learning and memory acquisition. The aims of this study were to investigate the effects displayed by strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae) leaves, on monoamine levels in rat hippocampus and on monoamine oxidase activity. A significance (p<0.01) of 83.5% reduction in 5-HT levels was observed after intra-hippocampal injection (20 μg/μl). After treatment by intraperitoneal route (10 mg/kg), a 63.4% reduction in 5-HT levels and a 67.4% reduction in DOPAC values were observed. The results indicate that strictosidinic acid seems to act on 5-HT system in rat hippocampus, possibly inhibiting precursor enzymes of 5-HT biosynthesis. The decrease verified in DOPAC levels suggests a role of strictosidinic acid in the dopaminergic transmission, probably due to an inhibition of monoamine oxidase activity, confirmed by the enzymatic assay, which demonstrated an inhibitory effect on MAO A in rat brain mitochondria.

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N,β-d-Glucopyranosyl vincosamide, a light regulated indole alkaloid from the shoots of Psychotria leiocarpa

Cited by 56 publications

References 23 publications

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Psychotria Genus

Strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae), decreases serotonin levels in rat hippocampus

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