Configurational and conformational analyses by theoretical methods of pentacyclic triterpenes isolated from Myricaria elegans

A. G. Pacheco, G. Salgado-Morán, A. F.C. Alcântara

Resultado de la investigación: Chapter

Resumen

Triterpenes are a large group of natural products widely distributed in the plant kingdom. These natural products exhibit a variety of pharmacological activities, such as anti-microbial, cytotoxic, hepatoprotective, and anti-inflammatory activities, making it a natural resource of great importance for the development of new drugs. The pentacyclic triterpenes eleganene-A and eleganene-B were isolated from aerial parts of Myricaria elegans Royle (Tamariscineae) and their structures were proposed through spectroscopic data of IR and NMR (1H and 13C) and mass spectrometry. The proposed structure of the phytoconstituents isolated of M. elegans indicates configuration 5S,9R for eleganene-A and configuration 5R,9R for eleganene-B (ring junctions A/B and B/C in cis form) which is in disagreement with the biosynthesis reported in the literature for these compounds. The configurational and conformational analyses of the triterpenes isolated from M. elegans were based on correlations between values of calculated carbon chemical shift (sC) and experimental data of 13C NMR (?C). As result, the correlations indicated stereochemistry 5R,9S for eleganene-A and 5S,9S for eleganene-B. Both the configurations show the slowest electronic-nuclear energies and ring junctions A/B and B/C in trans geometries, being in agreement with the biosynthesis proposed to these compounds.The structural analysis of eleganene-B also evaluated the stereochemical variations on centers which have substitutions by hydroxyl groups. Correlations between the values of sC and ?C show the best value of R2 for the structure with configuration 1R,2S,3S,6S.

Idioma originalEnglish
Título de la publicación alojadaNew Developments in Terpenes Research
EditorialNova Science Publishers Inc
Páginas237-247
Número de páginas11
ISBN (versión digital)9781629487618
ISBN (versión impresa)9781629487601
EstadoPublished - 1 ene 2014

Huella dactilar

Pentacyclic Triterpenes
Triterpenes
Biosynthesis
Biological Products
Nuclear magnetic resonance
Stereochemistry
Chemical shift
Natural resources
Structural analysis
Nuclear energy
Hydroxyl Radical
Mass spectrometry
Substitution reactions
Anti-Inflammatory Agents
Carbon
Antennas
Geometry
Pharmaceutical Preparations

ASJC Scopus subject areas

  • Chemical Engineering(all)

Citar esto

Pacheco, A. G., Salgado-Morán, G., & Alcântara, A. F. C. (2014). Configurational and conformational analyses by theoretical methods of pentacyclic triterpenes isolated from Myricaria elegans. En New Developments in Terpenes Research (pp. 237-247). Nova Science Publishers Inc.
Pacheco, A. G. ; Salgado-Morán, G. ; Alcântara, A. F.C. / Configurational and conformational analyses by theoretical methods of pentacyclic triterpenes isolated from Myricaria elegans. New Developments in Terpenes Research. Nova Science Publishers Inc, 2014. pp. 237-247
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Pacheco, AG, Salgado-Morán, G & Alcântara, AFC 2014, Configurational and conformational analyses by theoretical methods of pentacyclic triterpenes isolated from Myricaria elegans. En New Developments in Terpenes Research. Nova Science Publishers Inc, pp. 237-247.

Configurational and conformational analyses by theoretical methods of pentacyclic triterpenes isolated from Myricaria elegans. / Pacheco, A. G.; Salgado-Morán, G.; Alcântara, A. F.C.

New Developments in Terpenes Research. Nova Science Publishers Inc, 2014. p. 237-247.

Resultado de la investigación: Chapter

TY - CHAP

T1 - Configurational and conformational analyses by theoretical methods of pentacyclic triterpenes isolated from Myricaria elegans

AU - Pacheco, A. G.

AU - Salgado-Morán, G.

AU - Alcântara, A. F.C.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - Triterpenes are a large group of natural products widely distributed in the plant kingdom. These natural products exhibit a variety of pharmacological activities, such as anti-microbial, cytotoxic, hepatoprotective, and anti-inflammatory activities, making it a natural resource of great importance for the development of new drugs. The pentacyclic triterpenes eleganene-A and eleganene-B were isolated from aerial parts of Myricaria elegans Royle (Tamariscineae) and their structures were proposed through spectroscopic data of IR and NMR (1H and 13C) and mass spectrometry. The proposed structure of the phytoconstituents isolated of M. elegans indicates configuration 5S,9R for eleganene-A and configuration 5R,9R for eleganene-B (ring junctions A/B and B/C in cis form) which is in disagreement with the biosynthesis reported in the literature for these compounds. The configurational and conformational analyses of the triterpenes isolated from M. elegans were based on correlations between values of calculated carbon chemical shift (sC) and experimental data of 13C NMR (?C). As result, the correlations indicated stereochemistry 5R,9S for eleganene-A and 5S,9S for eleganene-B. Both the configurations show the slowest electronic-nuclear energies and ring junctions A/B and B/C in trans geometries, being in agreement with the biosynthesis proposed to these compounds.The structural analysis of eleganene-B also evaluated the stereochemical variations on centers which have substitutions by hydroxyl groups. Correlations between the values of sC and ?C show the best value of R2 for the structure with configuration 1R,2S,3S,6S.

AB - Triterpenes are a large group of natural products widely distributed in the plant kingdom. These natural products exhibit a variety of pharmacological activities, such as anti-microbial, cytotoxic, hepatoprotective, and anti-inflammatory activities, making it a natural resource of great importance for the development of new drugs. The pentacyclic triterpenes eleganene-A and eleganene-B were isolated from aerial parts of Myricaria elegans Royle (Tamariscineae) and their structures were proposed through spectroscopic data of IR and NMR (1H and 13C) and mass spectrometry. The proposed structure of the phytoconstituents isolated of M. elegans indicates configuration 5S,9R for eleganene-A and configuration 5R,9R for eleganene-B (ring junctions A/B and B/C in cis form) which is in disagreement with the biosynthesis reported in the literature for these compounds. The configurational and conformational analyses of the triterpenes isolated from M. elegans were based on correlations between values of calculated carbon chemical shift (sC) and experimental data of 13C NMR (?C). As result, the correlations indicated stereochemistry 5R,9S for eleganene-A and 5S,9S for eleganene-B. Both the configurations show the slowest electronic-nuclear energies and ring junctions A/B and B/C in trans geometries, being in agreement with the biosynthesis proposed to these compounds.The structural analysis of eleganene-B also evaluated the stereochemical variations on centers which have substitutions by hydroxyl groups. Correlations between the values of sC and ?C show the best value of R2 for the structure with configuration 1R,2S,3S,6S.

KW - Eleganenes

KW - Myricaria elegans

KW - Triterpenes

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M3 - Chapter

AN - SCOPUS:84949498883

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SP - 237

EP - 247

BT - New Developments in Terpenes Research

PB - Nova Science Publishers Inc

ER -

Pacheco AG, Salgado-Morán G, Alcântara AFC. Configurational and conformational analyses by theoretical methods of pentacyclic triterpenes isolated from Myricaria elegans. En New Developments in Terpenes Research. Nova Science Publishers Inc. 2014. p. 237-247