Alkaloids and other compounds from Psychotria correae

Achenbach, Hans; Lottes, M.; Waibel, Reiner; Karikas, George A.; Correa, Mireya; Gupta, Mahabir P.

doi:10.1016/0031-9422(94)00823-c

Cited by 74 publications

(61 citation statements)

References 20 publications

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“…Hodgkinsine (39), quadrigemine C (40), isopsychotridine B (41), psychotridine (42) , quadrigemine I (43), oleoidine (44) and caledonine (45) were obtained from P. oleoides. 66 From the aerial parts of P. glomerulata were isolated three quinoline alkaloids such as glomerulatine A (46), B (47) and C (48). 53 From extracts of the leaves and the roots of P. correae were obtained isodolichantoside (49) and the alkaloids correantoside (50), 10-hydroxycorreantoside (51), correantine A (52), B (53), and C (54), and 20-epi-correantine B (55).…”

Section: Alkaloidsmentioning

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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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 GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Calixto¹,

Pinto²,

Ramalho³

et al. 2016

Journal of the Brazilian Chemical Society

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“…7.6). 12 This chemical shift difference to a more deshielded position provided the clue for the determination of a seven member lactam ring derived from the intramolecular condensation of the indole nitrogen (N-1) with the original carbonyl of the methyl ester of secologanin. Comparison of these spectral features with those related to correantoside, a monoterpene indole alkaloid previously isolated from P. correae, showed high similarity, 12 with exception of the N-methyl group at N-1, present in correantoside but missing in 1.…”

Section: Resultsmentioning

confidence: 99%

“…The 12 From the above evidences, compound 1 was identified and named as the new N-demethylcorreantoside. The chemical structure and the observed key nOe correlations for compound 1 are presented in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

Alkaloid and other chemical constituents from Psychotria stachyoides Benth.

Pimenta

Uchôa

Braz‐Filho

et al. 2011

J. Braz. Chem. Soc.

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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.The organic extracts of leaves and roots of Psychotria stachyoides provided the new glucoside monoterpenoid indole alkaloid N-demethylcorreantoside, besides bizantionoside B, a-amyrin, alizarine methyl-ether, rubiadine, scopoletin, barbinevic acid and a mixture of b-sitosterol and stigmasterol glucosides. The structural characterization of the isolates was established based on infrared spectroscopy (IR), mass spectrometry (MS) and, particularly, 1D and 2D nuclear magnetic resonance (NMR). Keywords: monoterpene indole alkaloid, coumarins, naphthoquinones, triterpenes, Psychotria stachyoides IntroductionIndole alkaloids represent the biggest single class of all alkaloids from plants. The major groups under investigation are the ones with monoterpene (C 10 ) or nor-monoterpene (C 9 ) moieties joined to the tryptamine, which are distributed on a wide range of different structures in the Apocynaceae, Loganiaceae, Nyssaceae and Rubiaceae families. The genus Psychotria (Rubiaceae) comprises more than 1000 species distributed in tropical regions worldwide. This genus is taxonomically complex, and is particularly characterized as a prolific source of bioactive polyindole and monoterpenoid indole alkaloids. Previous phytochemical studies of species of Psychotria from the Southern Brazil have revealed the remarkable presence of glycosylated indole monoterpenoid alkaloids. 1As part of the investigative efforts to find alkaloids from Rubiaceae species of the Northeastern Brazil flora, Psychotria stachyoides (subgroup Heteropsychotria), a shrub growing predominantly in tropical and sub-tropical forests from Brazil (where it is popularly named as "erva-d'anta"), 2 has been investigated. This work reports the isolation and structural characterization of the new glucosilated monoterpene indole alkaloid named as N-demethylcorreantoside (1) from the leaves of P. stachyoides, in addition to the known bizantionoside B and a-amyrin. ) functionalities. From the 1 H NMR spectrum, a tetrahydro-b-carboline system was defined by Pimenta et al. 2217 Vol. 22, No. 11, 2011 the typical aromatic signals at d 7.22 (td, J 7.4 and 1.0 Hz, H-10), 7.26 (td, J 7.4 and 1.3 Hz, H-11), 7.45 (dd, J 7.4 and 1.3 Hz, H-9), 8.15 (dd, J 7.4 and 1.0 Hz, H-12), besides the two methylenes at d 3.10 (t, J 5.5 Hz, 2H-5) and 2.70 (t, J 5.4 Hz, 2H-6). 10 The 1 H NMR spectrum also showed signals relative to an iridoid unit related to a secologanin moiety due to the signals of the olefinic hydrogen at d 5.85 (ddd, J 17.6, 10.0 and 7.6 Hz, H...

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“…13 O ácido rotúndico já havia sido isolado nas espécies G. platypoda, 11 G. angelica 14 e G. grazielae 4 e o triterpeno 6 já havia sido encontrado no caule de G. grazielae. 4 O ácido clétrico está sendo descrito pela primeira vez no gênero, mas na família Rubiaceae já foi relatada sua presença em Morinda citrifolia (Noni), 15 Psychotria correae 16 e Mussaenda pubescens, 13 espécies consideradas medicinais. A substância 8 foi isolada da fração AcOEt como sólido amorfo e caracterizada como ácido 5-O-cafeoilquínico, através da comparação dos dados espectroscópicos de RMN com os descritos na literatura.…”

Section: Resultsunclassified

Constituintes químicos das folhas e avaliação da atividade anti-inflamatória de extratos das raízes e folhas de Guettarda pohliana Müll. Arg. (Rubiaceae)

Testa¹,

Oliveira²,

Silva³

et al. 2012

Quím. Nova

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Müll. Arg. (RUBIACEAE). This phytochemical investigation of Guettarda pohliana leaves led to the isolation of the triterpenes pomolic acid, rotundic acid, 3b,6a,19a,23-tetrahydroxyurs-12-en-28-oic acid, clethric acid, ursolic acid and oleanolic acid, the monoterpenoids loliolide and secoxyloganin, besides daucosterol and steroids. The structures of the isolated compounds were assigned on the basis of NMR data, including two-dimensional NMR methods. The anti-inflammatory activity of the crude methanolic extracts from leaves and roots, as well as of their fractions, was evaluated.Keywords: Guettarda pohliana; triterpenoid; anti-inflammatory activity. INTRODUÇÃOO gênero Guettarda, pertencente à tribo Guettardeae (Rubiaceae), compreende cerca de 150 espécies distribuídas em regiões tropicais e neotropicais.1 Espécies do gênero são popularmente utilizadas na América do Sul para tratamento de ferimentos e inflamações. 2Guettarda pohliana é uma espécie arbórea conhecida vulgarmente como angélica-do-mato. As espécies brasileiras G. platypoda e G. angelica, conhecidas pelo mesmo nome vulgar, são utilizadas popularmente como antifebris e antiespasmódicos 3 e possuem comprovadas atividades anti-inflamatória 3 e antibacteriana, 4 respectivamente. Em trabalho anterior, realizado com as raízes de Guettarda pohliana, reportou-se o isolamento do ácido quinóvico, de saponinas derivadas dos ácidos quinóvico e cinchólico, do daucosterol e do ácido 4,5-O-dicafeoilquínico, bem como a atividade antioxidante do extrato bruto e de suas frações. 5Em continuidade ao estudo da espécie G. pohliana, no presente trabalho descreve-se o isolamento e identificação de seis triterpenos, um monoterpeno, um derivado do ácido clorogênico, um secoiridoide e, ainda, os resultados de atividade anti-inflamatória dos extratos brutos e frações das folhas e das raízes. As estruturas das substâncias isoladas foram definidas com base na análise de dados espectroscópicos de RMN 1 H e 13 C uni-e bidimensionais (HMQC, HMBC, COSY e NOESY) e a comparação dos dados obtidos com os registrados na literatura. PARTE EXPERIMENTAL Procedimentos experimentais geraisOs espectros de RMN (uni-e bidimensionais) foram obtidos em espectrômetro Varian, modelo Mercury plus 300, operando a 300,06 MHz para 1 H e 75,46 MHz para 13 C. Os deslocamentos químicos são dados em ppm, tendo como referência interna o sinal do solvente e/ ou do tetrametilsilano (TMS, δ = 0,0 ppm). Para as cromatografias em coluna (CC) utilizou-se gel de sílica 60 (0,063-0,200 mm, Merck) ou Sephadex LH-20, como fase estacionária. Para as cromatografias em camada delgada (CCD) e em camada delgada preparativa (CCDP) empregou-se gel de sílica 60 G e 60 GF 254 (Merck). A visualização dos compostos em CCD foi realizada por irradiação com luz ultravioleta em 254 e 366 nm e/ou por pulverização com solução de H 2 SO 4 /MeOH (1:1), H 2 SO 4 /anisaldeído/ácido acético (1:0,5:50 mL) seguido de aquecimento. Material vegetalAs folhas da espécie Guettarda pohliana foram coletadas em abril de 2005, às margens da bacia de i...

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Alkaloids and other compounds from Psychotria correae

Cited by 74 publications

References 20 publications

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

Alkaloid and other chemical constituents from Psychotria stachyoides Benth.

Constituintes químicos das folhas e avaliação da atividade anti-inflamatória de extratos das raízes e folhas de Guettarda pohliana Müll. Arg. (Rubiaceae)

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