A new hemiterpene glycoside from the ripe tomatoes

Abstract

A new hemiterpene glycoside (1) was isolated from ripe tomatoes (the fruit of Lycopersicon esculentum, Solanaceae) along with eight known compounds. The chemical structure of 1 was determined to be 2-methylbutan-1-ol β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside, based on spectroscopic data as well as chemical evidence. In addition, the radical-scavenging activities of the isolated compounds on the free radical of 1,1-diphenyl-2-picrylhydrazyl were examined. Among the tested compounds, tryptophan, 4-O-β-d-glucopyranosyl caffeic acid and dihydro-p-coumaryl alcohol γ-O-β-d-glucopyranoside demonstrated 42.0%, 50.1% and 76.0% scavenging activities, respectively, at a concentration of 0.5 mM.

Keywords::

• Lycopersicon esculentum
• tomato
• Solanaceae
• hemiterpene glycoside
• radical-scavenging effect

Acknowledgements

We express our appreciation to Mr. K. Takeda and Mr. T. Iriguchi of Kumamoto University for their measurement of the MS and NMR spectra.

Additional information

Funding

This research was supported in part by a Grant-in-Aid for Scientific Research (C) (JSPS KAKENHI [grant numbers 19590030], [grant number 24590022]) from the Japan Society for the Promotion of Science. A part of this work was also supported by the Research and Study Project of Tokai University Educational System General Research Organisation (Kanagawa, Japan).