New Cytotoxic Bibenzyl and Other Constituents from Bauhinia ungulata L. (Fabaceae)

Chem Biodivers. 2016 Dec;13(12):1630-1635. doi: 10.1002/cbdv.201600058. Epub 2016 Nov 16.

Abstract

A new bibenzyl, 2'-hydroxy-3,5-dimethoxy-4-methylbibenzyl (1) and four known compounds identified as 2'-hydroxy-3,5-dimethoxybibenzyl (2), liquiritigenin (3), guibourtinidol (4) and fisetinidol (5) were isolated from the roots of Bauhinia ungulata L. Phytochemical investigations of the stems of B. ungulata led to the isolation of the known compounds identified as liquiritigenin (3), guibourtinidol (4), fisetinidol (5), taraxerol (6), betulinic acid (7), taraxerone (8), glutinol (9), a mixture of sitosterol (10) and stigmasterol (11), pacharin (12), naringenin (13) and eriodictyol (14). The structures of these compounds were elucidated on the basis of their spectral data (IR, MS, 1D- and 2D-NMR). The cytotoxicity of the bibenzyl 1 has been evaluated against four human cancer cell lines, showing the IC50 values of 4.3 and 6.5 μg ml-1 against pro-myelocytic leukemia (HL-60) and cervical adenocarcinoma (HEP-2) cell lines, respectively. This article also registers for the first time the 13 C-NMR data of the known bibenzyl 2.

Keywords: Bauhinia ungulata; Bibenzyls; Cytotoxic activities; Flavonoids; Triterpenoids.

MeSH terms

  • Benzyl Compounds / chemistry
  • Benzyl Compounds / isolation & purification
  • Benzyl Compounds / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Fabaceae / chemistry*
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Benzyl Compounds