Tertiary Indole Alkaloids of Tabernaemontana dichotoma Seeds

Perera, Premila; Sandberg, F; Beek, T.A. van; Verpoorte, Robert

doi:10.1055/s-2007-969804

Cited by 21 publications

(11 citation statements)

References 6 publications

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“…This fact and the relative low field shifts of the H-19 protons (i.e. compare with voaphylline which has 11-18 at 0.73 ppm and both H-19 at 1.11 ppm) [9] agreed well with structure 1, which has an oxygen substitution at C-20. This structure constitutes a novel type of iboga skeleton.…”

Section: Resultssupporting

confidence: 72%

“…In determining the absolute stereochemistry at C-14 the recorded CD spectrum was of little use because no reference spectrum of a similar substance existed. Therefore by biosynthetical reasoning the stereochemistry at C-14 was assumed to be S because all other iboga alkaloids isolated from the two species investigated [1,3,9,11] and from all Taber- fig. 1).…”

Section: Resultsmentioning

confidence: 99%

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Dichomine, a Novel Type of Iboga Alkaloid*,**

Perera

Beek²,

Verpoorte³

1983

Planta Med

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Section: Resultssupporting

confidence: 72%

Section: Resultsmentioning

confidence: 99%

Dichomine, a Novel Type of Iboga Alkaloid*,**

Perera

Beek²,

Verpoorte³

1983

Planta Med

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“…Os compostos majoritários presentes nos alcalóides totais foram isolados por sucessivas etapas de cromatografia em camada preparativa sendo os compostos isolados analisados por CG-EM e 1 H-RMN e os dados espectrais foram comparados com dados da literatura (Perera et al, 1983) indicando que os mesmos tratavamse da voacangina 1 e da coronaridina 2. Estes alcalóides são comumente encontrados em espécies do gênero Tabernaemontana com ocorrência no Brasil, tais como T. fuchsiaefolia, T. divaricata, T. catharinensis e T. laeta (Andrade et a., 2005;Zocoler et al, 2005;Pereira et al, 2004;Medeiros et al, 2001) …”

Section: Resultsunclassified

Isolamento e avaliação da atividade biológica dos alcalóides majoritários de Tabernaemontana angulata Mart. ex Müll. Arg., Apocynaceae

Assis¹,

Moreno²,

Young³

et al. 2009

Rev. bras. farmacogn.

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RESUMO:A necessidade da introdução de novos agentes quimioterápicos é uma realidade no controle de doenças infecciosas. O Brasil é o país mais rico em biodiversidade, e o Laboratório de Extração da Universidade Paulista tem coletado plantas na Amazônia e Mata Atlântica com a finalidade de identificar extratos vegetais antibacterianos e antitumorais. Estudos prévios demonstraram que a fração etanólica obtida do extrato bruto orgânico do caule de Tabernaemontana angulata Mart. ex Müll. Arg. apresentou atividade antimicrobiana significante contra Staphylococcus aureus ATCC6538, no ensaio de diluição em caldo. Verificou-se por cromatografia em camada delgada que os compostos majoritários presentes na fração ativa eram alcalóides. No presente trabalho, foi obtida a fração de alcalóides totais a partir do extrato bruto, da qual os compostos majoritários foram isolados por sucessivas cromatografias e, posteriormente, identificados por CG-EM e 1 H-RMN como os alcalóides indólicos coronaridina e voacangina. As frações obtidas do isolamento foram testadas no ensaio biológico, porém não demonstraram atividade antimicrobiana.Unitermos: Tabernaemontana angulata, Apocynaceae, alcalóides, atividade antibacteriana, citotoxicidade.ABSTRACT: "Isolation and evaluation of the biological activity related to the major alkaloids in Tabernaemontana angulata Mart. ex Müll. Arg., Apocynaceae." Introducing new chemotherapeutic agents is a great demand in the control of infectious diseases. Brazil is one of the richest countries in biodiversity and the Laboratório de Extração at UNIP has been collecting plants from the Amazon and Atlantic Rain Forests with the aim of screening for new antibacterial and antitumor plant extracts. Previous studies demonstrated that the ethanol fraction obtained from the crude extract of Tabernaemontana angulata stems showed an antibacterial activity against Staphylococcus aureus (ATCC 6538) in the microdilution broth assay. Two alkaloids were the major compounds in the active fraction, verified by thin layer chromatography analysis. In the present study, the total alkaloids were obtained from the crude extract and were fractionated by preparative thin layer chromatography for the isolation of the main components. The isolated compounds were identified by GC/MS and 1 H-NMR as coronaridine and voacangine. The alkaloid fractions obtained from the isolation procedure were tested for antibacterial activity, but no activity was detected.

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“…a few unassigned signals 4 by the combined use of COSY, HMQC and HMBC experiments. The complete 1 H and 13 C assignments are presented in Table 1, and show significant differences from the 13 C assignments of stemmadenine.…”

Section: Spectral Assignments and Reference Datamentioning

confidence: 99%

“…The complete 1 H and 13 C assignments are presented in Table 1, and show significant differences from the 13 C assignments of stemmadenine. 4 …”

Section: Spectral Assignments and Reference Datamentioning

confidence: 99%