Stereochemical Analysis of Leubethanol, an Anti-TB-Active Serrulatane, from <i>Leucophyllum frutescens</i>
Gloria M. Molina-Salinas
Verónica M. Rivas-Galindo
Salvador Said-Fernández
David C. Lankin
Marcelo A. Muñoz
Pedro Joseph-Nathan
Guido F. Pauli
Noemí Waksman
10.1021/np2000667.s001
https://acs.figshare.com/articles/journal_contribution/Stereochemical_Analysis_of_Leubethanol_an_Anti_TB_Active_Serrulatane_from_i_Leucophyllum_frutescens_i_/2611636
Bioactivity-guided fractionation of the methanolic root bark extract of <i>Leucophyllum frutescens</i> led to the identification of leubethanol (<b>1</b>), a new serrulatane-type diterpene with activity against both multi-drug-resistant and drug-sensitive strains of virulent <i>Mycobacterium tuberculosis</i>. Leubethanol (<b>1</b>) was identified by 1D/2D NMR data, as a serrulatane closely related to erogorgiane (<b>2</b>), and exhibited anti-TB activity with minimum inhibitory concentrations in the range 6.25–12.50 μg/mL. Stereochemical evidence for <b>1</b> was gleaned from 1D and 2D NOE experiments, from <sup>1</sup>H NMR full spin analysis, and by comparison of the experimental vibrational circular dichroism (VCD) spectrum to density functional theory calculated VCD spectra of two diastereomers.
2011-09-23 00:00:00
Mycobacterium tuberculosis
VCD spectra
evidence
strain
fractionation
serrulatane
Leubethanol
methanolic root bark
2 D NOE experiments
Leucophyllum frutescens
density
spectrum
erogorgiane
1 H NMR
concentration
identification
Stereochemical Analysis
leubethanol
data
1 D
diterpene
dichroism
vibrational
analysis
diastereomer
Serrulatane