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2011•Journal of Chemical ResearchRequires access

A New Friedelane Triterpenoid from the Branches of Maytenus Gonoclada (Celastraceae)

Fernando César Silva, Vanessa Gregório Rodrigues, Lucienir Pains Duarte, Grácia D. F. Silva, Roqueline Rodrigues Silva de Miranda, Sidney Augusto Vieira Filho

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Abstract

A new friedelane type triterpene, 3,16-dioxo-12α-hydroxyfriedelane was isolated from the chloroform extract of branches of Maytenus gonoclada Martius (Celastraceae) together with nine known compounds: 3, 11-dioxofriedelane, 3, 16-dioxofriedelane, 3, 12-dioxofriedelane, 3-oxo-12α,29-dihydroxyfriedelane, 3-oxofriedelane (friedelin), 3β-hydroxyfriedelane, 3-oxo-12α-hydroxyfriedelane and 3β-hydroxylup-20(29)-ene (lupeol) and a mixture of long chain hydrocarbons. The structure and stereochemistry of the new friedelane triterpene were established from the 1 H NMR and 13 C NMR spectra including two-dimensional experiments (HSQC, HMBC and NOESY) and high resolution mass spectrometry.

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What this paper is about

A new friedelane type triterpene, 3,16-dioxo-12α-hydroxyfriedelane was isolated from the chloroform extract of branches of Maytenus gonoclada Martius (Celastraceae) together with nine known compounds: 3, 11-dioxofriedelane, 3, 16-dioxofriedelane, 3, 12-dioxofriedelane, 3-oxo-12α,29-dihydroxyfriedelane, 3-oxofriedelane (friedelin), 3β-hydroxyfriedelane, 3-oxo-12α-hydroxyfriedelane and 3β-hydroxylup-20(29)-ene (lupeol) and a mixture of long chain hydrocarbons. The structure and stereochemistry of the new friedelane triterpene were established from the 1 H NMR and 13 C NMR spectra including two-dimensional experiments (HSQC, HMBC and NOESY) and high resolution mass spectrometry.

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Available abstract

A new friedelane type triterpene, 3,16-dioxo-12α-hydroxyfriedelane was isolated from the chloroform extract of branches of Maytenus gonoclada Martius (Celastraceae) together with nine known compounds: 3, 11-dioxofriedelane, 3, 16-dioxofriedelane, 3, 12-dioxofriedelane, 3-oxo-12α,29-dihydroxyfriedelane, 3-oxofriedelane (friedelin), 3β-hydroxyfriedelane, 3-oxo-12α-hydroxyfriedelane and 3β-hydroxylup-20(29)-ene (lupeol) and a mixture of long chain hydrocarbons. The structure and stereochemistry of the new friedelane triterpene were established from the 1 H NMR and 13 C NMR spectra including two-dimensional experiments (HSQC, HMBC and NOESY) and high resolution mass spectrometry.

Key concepts: Celastraceae, Friedelin, Lupeol, Triterpene, Chemistry, Two-dimensional nuclear magnetic resonance spectroscopy, Stereochemistry, Triterpenoid

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