Antiprotozoal alkaloids from Psychotria prunifolia (Kunth) Steyerm
Laryssa Ribeiro2012, Journal of the Brazilian Chemical Society
Sign up for access to the world's latest research
checkGet notified about relevant papers
checkSave papers to use in your research
checkJoin the discussion with peers
checkTrack your impact
Abstract
A continuidade do estudo fitoquímico de P. prunifolia com a análise dos extratos etanólicos obtidos a partir de suas raízes e galhos levou ao isolamento de cinco alcaloides indol-b-carbolínicos dos quais, dois derivados, o 10-hidróxi-iso-deppeaninol e o N-óxido-10-hidróxi-antirhina são descritos pela primeira vez. As estruturas foram determinadas por análise de técnicas espectroscópicas de IV, EMAR e RMN ( 1 H e 13 C, 1D e 2D). A avaliação da atividade frente à Leishmania amazonensis e Trypanosoma cruzi, mostrou que os extratos brutos e os alcaloides 14-oxoprunifoleína e estrictosamida inibiram as formas promastigotas de L. amazonensis, com valores de CI 50 de 16,0 e 40,7 mg per mL, respectivamente.
Related papers
Bioactive alkaloids from medicinal plants of Lombok
2002
The aims of this project were to: 1) assess the efficacy of a combined chemo-and biorational approach involving alkaloid occurrence with antimicrobial medicinal plant use, focussing on plants from Lombok island. Lombok has a large population while herbal medicines are widely used with a diverse range of plant species. 2) Investigate the alkaloid constituents of selected plants including isolation, purification, and characterisation, and structure elucidation. 3) Evaluate antibacterial and antimalarial activities of crude alkalo extracts and major alkaloid compounds isolated from the plants. 4) Identify compounds as possible new drug leads. A combined chemo-and bio-rational strategy based on alkaloid content and traditional medicinal plant use was demonstrated to be an effective and efficient approach to finding new biologically active compounds in nature. Several new alkaloids were isolated with some potential for development as antibacterial and antimalarial agents. Some previously known alkaloids were also isolated, and in some cases NMR features not previously reported in the literature are presented. A new optically active indole alkaloid, lombine (major), and the known alkaloid voacangine (minor), were identified from the bark of Voacanga foetida (Bl.) Rolfe, used ethnomedically for the treatment of wounds, itches, and swellings. The fruits of the plant produced three known alkaloid compounds, coronaridine (major), voacangine, and xi voacristine, together with the new indole alkaloids mataranine A and B, which were also isolated from Alstonia scholaris R. Br. in this study. Voacristine was found as a major alkaloid together with the minor alkaloid voacangine from the leaves of V. foetida (Bl.) Rolfe. A structural revision for voacristine was also completed. Initial antibacterial testing of the crude alkaloid extract from V. foetida (Bl.) Rolfe (and fruits) showed activity against both Gram-positive bacteria [Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). The new alkaloids lombine (bark) and mataranine A and B (fruits) also exhibited antibacterial activity. Bactericidal activity observed for lombine at a concentration of 0.5 mg/ml against S. aureus and E. coli. At the lower concentration of 0.05 mg/l, it partially inhibited the growth of both S. aureus and E coli. The crude alkaloid extract from the leaves was found to be active only against S. aureus. Voacristine was considered most likely to be the main active component. These compounds particularly lombine, are thus useful as potential drug leads. Another new antibacterial agent (LPM-574), a substituted derivative of hodgkinsine, was isolated from Psychotria malayana Jack (leaves). This compound, the structure of which was not completely elucidated, was found to have bacteriostatic potency against S. aureus and E. coli at a concentration of 1.0 mg/ml. The major alkaloid component, hodgkinsine, showed no antibacterial activity at this concentration. However, further structure elucidation and testing are needed for compound LMP-574 before it can be considered as a viable drug lead. Another new indole alkaloid labeled as LPM-186 was isolated as minor compound from this plant. xii F r o m the plant Alstonia scholaris (leaves; young trees), used in the treatment of malaria, the new indole alkaloids mataranine A and B were isolated. The crude extract of this plant exhibited antimalarial activity against Plasmodium falciparum, with EC50 values in vitro against antifolate resistant parasites (KI strain) and antifolate sensitive parasites (TM4 strain) of 15.6 Jig/ml and 21.0 (ig/ml respectively. The new diastereomeric alkaloids mataranine A and B (mixture) had increased potency against KI with an EC50 of 2.6 M-g/ml (7.4 |iM) and EC 50 value of 3.4 p,g/ml (9.7 pM) against the TM4 strain. Thus, either mataranine A or B, or the mixture, could provide useful new leads not only for antimalarial compounds but also for antibacterial agents. Two other new alkaloids, (15S*, 16S*)losbanine and kotarajine, and the known alkaloids alstonamine and (EAakuammidine, were also isolated from leaves of young trees of A. scholaris. The antimalarial testing of these compounds has not been carried out as yet. While there is some indication that the plants, Clerodendron calamitosum L. (the leaves were used for the treatment of malaria and wounds) and C. paniculatum (the flowers were used to cure sore eyes), based on their traditional medicinal uses, might contain some new alkaloids, full structure elucidation was not achieved due to the very small quantities available. The crude alkaloid extract from each plant did show some antibacterial activity against E. coli. The crude alkaloid extract from C. calamitosum L. also showed activity against antifolate-resistant Plasmodium falciparum parasites (KI) in vitro and it was found that the major alkaloid, compound Lcc-3, was responsible for the activity.
Alkaloid and other chemical constituents from Psychotria stachyoides Benth
Journal of the Brazilian Chemical Society, 2011
Os extratos orgânicos das folhas e raízes de Psychotria stachyoides forneceram o novo alcaloide indólico monoterpênico glicosilado N-desmetil-correantosida, além de bizantionosida B, a-amirina, éter metílico da alizarina, rubiadina, escopoletina, ácido barbinévico e uma mistura de b-sitosterol e estigmasterol glicosilados. A caracterização estrutural dos compostos isolados foi estabelecida com base na espectroscopia no infravermelho (IR), espectrometria de massa (MS) e particularmente ressonância magnética nuclear (RMN) 1D e 2D.
Natural products and bioactive alkaloids from plants
Natural products had been indispensably used in traditional medicines for thousands of years. These traditional medicines cater to about 85% ofthe world population for their primary health care needs.
Indole monoterpene alkaloids from leaves of Psychotria suterella Müll. Arg. (Rubiaceae)
Biochemical Systematics and Ecology, 2001
S 0 3 0 5 -1 9 7 8 ( 0 1 ) 0 0 0 5 9 -X
Quaternary β-carboline alkaloids from Psychotria prunifolia (Kunth) Steyerm
Phytochemistry Letters, 2010
Indole Alkaloids from Antirhea portoricensis
Journal of Natural Products, 1994
Bioactive Alkaloids from South American Psychotria and Related Species
The Open Bioactive Compounds Journal, 2009
Many important molecules have been discovered from tropical and sub-tropical plant biodiversity. However, the largest part of the chemical profile of such biodiversity remains unknown. Combining ethnopharmacological and chemotaxonomical investigation can be a good strategy in bioactive compound discovery. South American Psychotria species studied by this approach proved to be a rich source of new bioactive alkaloids, some of which bear unique chemical skeletons.
Antiprotozoal activity of Brazilian plant extracts from isoquinoline alkaloid-producing families
Phytomedicine, 2005
Leishmaniasis and Chagas disease afflict the poorest countries in the world. The Brazilian flora represents a rich source for the screening of potential antiparasitic compounds. In this work, we tested the total alkaloid and ethanol extracts of nine different plants from Brazilian families which produce isoquinoline alkaloids, to determine their in vitro antiparasitic effect against L. chagasi and T. cruzi parasites. Promastigotes of L .chagasi were shown to be susceptible only to the total alkaloid extracts of A. crassiflora (EC50 value=24.89μg/ml), A. coriacea (EC50 value=41.60μg/ml), C. ovalifolia (EC50 value=63.88μg/ml) and G. australis (EC50 value=37.88μg/ml). Except for the G. australis total alkaloids, all the three extracts presented a considerable activity when tested against intracellular amastigotes. The most effective alkaloid extracts were those from A. crassiflora and C. ovalifolia, which reduced the number of infected macrophages at 25μg/ml by 86.1% and 89.8%, respect...
Some of South Sumatran Plants Containing Alkaloids
IJFAC (Indonesian Journal of Fundamental and Applied Chemistry), 2022
A phytochemical survey for alkaloid-containing plants has been conducted in South Sumatra including traditional medicinal plants. During the survey 180 satisfactory herbarium sample were obtained and all of them were tested for alkaloids. The results showed that 33 species gave a positive test for alkaloids, and high alkaloid contents were shown by: Alstonia scholaris, Alstonia angustiloba, Ervatamia coronariaa, Voacanga foetida Bl. K. Schum, Litseaacceden toides K & V, Litsea angualata, Litsea tomentosa, Fibraurea chloroleuca Miers (root), and Uncaria cordata (Lour.) Merr. The aboved survey was also continued to be an intensively phytochemical work focusing on alkaloid of Fibraurea chloroleuca Miers root. A quaternary isoquinoline alkaloid as a yellowish crystal, m.p. 214-215 o C; MS (FAB) m/z 352 has been successfully isolated and tested for antibacterial activity. This isolated alkaloid significantly inhibited Bacilus substilis, Shigela dysentriae, Staphylococus aireus, and Pseudomonas sp growth at 1 mg/mL. As a result, all of these alkaloid-containing plants are potential to explore their alkaloids and utilitarian for traditional medicines.
Unusual monoterpene indole alkaloids from Psychotria stachyoides Benth
Biochemical Systematics and Ecology, 2010
Antimycobacterial Activity and Alkaloid Prospection of Psychotria Species (Rubiaceae) from the Brazilian Atlantic Rainforest
Planta Medica, 2011
Antimycobacterial Activity and Alkaloid Prospection of<i>Psychotria</i>Species (Rubiaceae) from the Brazilian Atlantic Rainforest
Planta Medica, 2011
Antileishmanial potential of alkaloids isolated from plants: an integrative review
Research, Society and Development, 2020
Leishmaniasis treatment is often carried out with drugs of high toxic potential and high cost, and satisfactory therapeutic response is not usually observed. In this context, searching for therapeutic alternatives is urgent. This study seeks to evaluate the antileishmanial potential of alkaloids from plants. The search for scientific papers occurred at Pubmed, CAPES Journal Portal (PPC), Virtual Health Library (VHL) and COCHRANE using the descriptors: alkaloid and antileishmanial. The inclusion criteria were studies about alkaloids isolated from plants and tested against Leishmania parasite. A total of 805 publications were found in Pubmed, 825 in PPC, 4 in VHL and none in COCRHANE. After reading the titles and abstracts, articles containing other biological evaluations (350), chemical studies such as docking and material characterizations (388), evaluation of extracts and fractions activities (406) which did not fit in this research or were in duplicate (377) were excluded. Acridon...
Neuropharmacology Activity of Alkaloids from South American Medicinal Plants
Current Medicinal Chemistry-Central Nervous System Agents, 2002
Higher plants, which have served humankind as sources of biologically active molecules since its earliest beginnings, continue to play a key role in the world health. Compounds from higher plants are of great potential value as medicinal agents, as "leads" or model compounds for synthetic or semisynthetic structure modifications and optimization, as biochemical and/or pharmacological probes.
Antiplasmodial Alkaloids from the Bark of
2013
A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC 50 value of 2.82 μg/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished by means of high field 1D-and 2D-NMR, IR, UV and LCMS spectral data. The isolated extract constituents (+)-N-methylisococlaurine (1), atherosperminine (2) and 2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC 50 values of 5.40, 5.80 and 0.75 μM, respectively. In addition, (+)-N-methylisocolaurine (1) and atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC 50 values of 29.56 ug/mL and 54.53 ug/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC 50 values of 50.08 ug/mL and 42.87 ug/mL, respectively.
Plant-derived antimalarial agents: new leads and efficient phythomedicines. Part I. Alkaloids
Anais da Academia Brasileira de Ciências, 2009
Malaria remains one of the most serious world health problem and the major cause of mortality and morbidity in the endemic regions. Brazil is among the 30 high-burden countries and most of the cases occur in the Legal Amazonian Region. New chemotherapeutical agents are needed for the treatment of malaria. Many plant species are used in traditional medicines of malarious countries and a relatively few number of these have been investigated for evaluation of their antimalarial effect. Still lower is the number of those that have had the active natural compounds isolated and the toxicity determined. This area is, then, of great research interest. A discovery project of antimalarial natural products from plants traditionally used to treat malaria must include in vitro and in vivo assays as well as bioguided isolation of active compounds. The final products would be antimalarial chemical entities, potential new drugs or templates for new drugs development, and/or standardized antimalarial extracts which are required for pre-clinical and clinical studies when the aim is the development of effective and safe phythomedicines. This review discusses these two approaches, presents briefly the screening methodologies for evaluation of antimalarial activity and focuses the activity of alkaloids belonging to different structural classes as well as its importance as new antimalarial drugs or leads and chemical markers for phytomedicines.
Indole alkaloids: 2012 until now, highlighting the new chemical structures and biological activities
Fitoterapia, 2020
Indole alkaloids have attracted attention because of their therapeutic properties, being anti-inflammatory, antinociceptive, antitumoural, antioxidant and antimicrobial. These compounds present a wide structural diversity, which is directly related to the genera of the producing plants, as well as the biological activities. Indole alkaloids have attracted attention over the last decade because of this combination of bioactivity and structural diversity. Therefore, this review presented recent (2012-2018) advances in alkaloids, focusing on new compounds, extraction methods and biological activities. As such, approximately 70 articles were identified, which showed 261 new compounds produced by plants of the families Apocynaceae, Rubiaceae, Annonaceae and Loganiaceae. In addition, different extraction methods were identified, and the structures of the new compounds were analysed. In addition to indole molecules, there were mono-indole-, di-indole-, vinblastine-, vimblastine-, gelsedine-, geissospermidine-, koumine-, geissospermidine-, iboga-, perakine-, corynanthe-, vincamine-, ajmaline-, aspidorpema-, strychnos-type, β-carboline alkaloids and indole alkaloid glucosides. The reported biological activities are mainly anticancer, antibacterial, antimalarial, antifungal, antiparasitic, and antiviral, as well as anti-acetylcholinesterase and anti-butyrylcolinesterase properties. This review serves as a guide for those wishing to find the most recently identified alkaloid structures and their associated activities.
Structure elucidation of alkaloids from Philippine flowering plants
1992
This work forms part of growing studies on Natural Product Chemistry in the Philippines. Alkaloid field screening conducted by the University of Santo Tomas Research Centre provided the opportunity to carry out this study on five endemic Philippine plants. Structural elucidation of the alkaloids present in three of these plants was obtained largely by physical methods, most importantly by the use of sophisticated NMR techniques which are described in detail in the text. Talauma gitingensis of the family Magnoliaceae afforded the oxoaporphine liriodenine and two noraporphine alkaloids, anonaine and xylopine, both of which were characterised as their N-acetyl derivatives. The existence of conformational isomerism for the Nacetyl derivatives was described for the first time together with a complete NMR characterisation of the compounds using 1-D decoupling experim ents, nOe enhancem ent and 2-D COSY spectroscopy. This was also the first reported isolation of anonaine in the genus Talau...
Cited by
Secondary Metabolites from Rubiaceae Species
Molecules, 2015
This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion.
Alkaloid diversification in the genus Palicourea (Rubiaceae: Palicoureeae) viewed from a (retro-)biogenetic perspective
Phytochemistry Reviews
The species-rich genus Palicourea (Rubiaceae: Palicoureeae) is source of an intriguing diversity of alkaloids derived from tryptamine and its precursor tryptophan. So far simple tryptamine analogues, polypyrroloindoline, β-carboline, and, most importantly, monoterpene-indole, i.e., tryptamine-iridoid alkaloids of various structural types including javaniside, alstrostine and strictosidine derivatives have been identified. Here the diverse alkaloids that numerous studies have found in the genus are examined and organized according to their structures and biosynthetic groups. Using a parsimony-based approach that follows the concept of retro-biogenesis usually applied in synthetic chemistry, possible biosynthetic pathways are proposed and important steps and relationships between these alkaloids are highlighted. Understanding alkaloid diversification is of importance in studying the ecological significance and evolution of biosynthetic capabilities of the genus Palicourea, and should ...
13C-NMR Spectral Data of Alkaloids Isolated from Psychotria Species (Rubiaceae)
Molecules, 2017
The genus Psychotria (Rubiaceae) comprises more than 2000 species, mainly found in tropical and subtropical forests. Several studies have been conducted concerning their chemical compositions, showing that this genus is a potential source of alkaloids. At least 70 indole alkaloids have been identified from this genus so far. This review aimed to compile 13 C-NMR data of alkaloids isolated from the genus Psychotria as well as describe the main spectral features of different skeletons.
The Spatial Distribution of Alkaloids in Psychotria prunifolia (Kunth) Steyerm and Palicourea coriacea (Cham.) K. Schum Leaves Analysed by Desorption Electrospray Ionisation Mass Spectrometry Imaging
Phytochemical analysis : PCA, 2017
Species of the genera Psychotria and Palicourea are sources of indole alkaloids, however, the distribution of alkaloids within the plants is not known. Analysing the spatial distribution using desorption electrospray ionisation mass spectrometry imaging (DESI-MSI) has become attractive due to its simplicity and high selectivity compared to traditional histochemical techniques. To apply DESI-MSI to visualise the alkaloid distribution on the leaf surface of Psychotria prunifolia and Palicourea coriacea and to compare the distributions with HPLC-MS and histochemical analyses. Based upon previous structure elucidation studies, four alkaloids targeted in this study were identified using high resolution mass spectrometry by direct infusion of plant extracts, and their distributions were imaged by DESI-MSI via tissue imprints on a porous Teflon surface. Relative quantitation of the four alkaloids was obtained by HPLC-MS/MS analysis performed using multiple-reaction monitoring (MRM) mode on...
Anti-inflammatory constituents from Psychotria prainii H. Lév
Natural product research, 2017
One new and three known compounds were isolated from the ethanol extract of Psychotria prainii aerial parts. By means of spectroscopic methods, their structures were elucidated to be deacetylasperulosidic acid 6-ethyl ether (1), asperulosidic acid (2), asperuloside (3) and obtucarbamates C (4). The isolated compounds were evaluated for their inhibitory effect on NO production in LPS-stimulated RAW264.7 cells. Among them, compounds 2 and 4 exhibited strong effect with the IC50 values of 5.75 ± 0.85 and 6.92 ± 0.43 μM, respectively. This is the first report for the chemical composition and biological activity of P. prainii.
Loading Preview
Sorry, preview is currently unavailable. You can download the paper by clicking the button above.