Chemical profile and biological activities of Lysiphyllum binatum (Blanco) de Wit.

Abstract

Lysiphyllum binatum (Blanco) de Wit in the Fabaceae family, despite its traditional medicinal uses, has not been the subject of prior scientific inquiry into its chemical and biological profile. The dichloromethane and MeOH extracts of its roots exhibited notably similar antioxidant activity, while the dichloromethane extract of the vine stems showed aromatase inhibition. This study aimed to identify the bioactive components responsible for these activities. Chemical investigation of the roots led to the isolation of six new metabolites, named lysiphans A-F (1-6), along with eight known compounds (7-14). The vine stem yielded lysiphan C (3) and compound 7, as well as five known isolates (15-19). The structures of these metabolites were determined through NMR spectral analysis, HRESIMS, quantum chemical calculations of NMR and ECD spectra, and Mosher's modifications to establish their absolute configurations. The biogenetic relationships between the new compounds were proposed. Several of the isolates were evaluated for their antioxidant, anti-aromatase, and cytotoxic properties. Lysiphan B (2) exhibited significant antioxidant activity, with an IC₅₀ value of 28.8 ± 0.4 μM in the diphenyl picrylhydrazyl radical (DPPH) assay, 3.5 ± 0.2 μM in the xanthine/xanthine oxidase (XXO) assay, and 1.5 ± 0.0 ORAC units in oxygen radical absorbance capacity (ORAC) assay. Additionally, compounds 12, 13, and 16 exhibited very strong aromatase inhibitory activity with IC₅₀ values of 0.3 ± 0.2, 4.7 ± 0.1, and 0.9 ± 0.2 µM, respectively. Compound 16 also demonstrated strong ORAC activity of 1.9 ± 0.1 ORAC units.