Specific hydrolysis and accumulation of antiproliferative lignans in the fruit of Leuzea carthamoides (Willd.) DC.

Abstract

Dibenzylbutyrolactone-type lignan glycosides (tracheloside and carthamoside), their aglycones (trachelogenin and carthamogenin) and feruloyl-serotonin isomers were determined in the fruits of Leuzea carthamoides by using LC–UV, LC–MS/MS and GC–MS techniques. The composition of the embryo and wall parts of the fruits was analysed before and after their hydrolysis. As a result of these studies, fruit part-specific accumulation of lignan glycosides and feruloyl-serotonins were confirmed, demonstrating that the embryo contains a high amount of lignan glycosides (tracheloside 32.9 mg/g, carthamoside 45.3 mg/g), while the wall part of the fruit accumulates feruloyl-serotonins (63.0 mg/g). Enzymatic hydrolysis of the embryo resulted in the quantitative transformation of lignan glycosides into their corresponding aglycones, allowing selective isolation of trachelogenin and carthamogenin. These aglycones were subjected to an antiproliferative study against the SW480 colon adenocarcinoma cell line. In this test, moderate activity of carthamogenin and a significant effect of trachelogenin were demonstrated in a concentration range of 22–185 μM.

Keywords::

• Leuzea
• analysis of lignans
• carthamogenin
• trachelogenin
• arctigenin
• antiproliferative activity

Acknowledgements

The authors are grateful to Professor Ilona Kovalszky and to Dr Kornélia Baghy for their valuable advice in preparing this article.

Notes

^1. Isolations were performed from selected fruit tissues; see Section 2.3, paragraphs 1–3.