Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 374497
Title Isolation, Characterization, and Surfactant Properties of the Major Triterpenoid Glycosides from Unripe Tomato Fruits
Author(s) Yamanaka, T.; Vincken, J.P.; Waard, P. de; Sanders, M.G.; Takada, N.; Gruppen, H.
Source Journal of Agricultural and Food Chemistry 56 (2008)23. - ISSN 0021-8561 - p. 11432 - 11440.
DOI https://doi.org/10.1021/jf802351c
Department(s) Food Chemistry
Biophysics
AFSG Quality in Chains
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2008
Keyword(s) steroidal alkaloid glycosides - tandem mass-spectrometry - lycopersicon-esculentum - electrospray-ionization - liquid-chromatography - glycoalkaloids - saponins - plant - dehydrotomatine - soyasaponins
Abstract Various triterpenoid glycosides were extracted from whole unripe tomato fruits (Lycopersicon esculentum cv. Cedrico), using aqueous 70% (v/v) ethanol to study their surfactant properties. Cation-exchange chromatography using a Source 15S column and subsequent semipreparative HPLC using an XTerra RP18 were employed to purify individual triterpenoid glycosides from the extract. The structure of the purified compounds was established by mass spectrometry and nuclear magnetic resonance spectroscopy. The furostanol glycoside tomatoside A (749 mg/kg of DW) and the glycoalkaloids ¿-tomatine (196 mg/kg of DW) and esculeoside A (427 mg/kg of DW) were the major triterpenoid glycosides present. Furthermore, minor amounts of a new dehydrofurostanol glycoside, dehydrotomatoside, were found. The critical micelle concentrations of the major triterpenoid glycosides, ¿-tomatine, tomatoside A, and esculeoside A, were determined as 0.099, 0.144, and 0.412 g/L, respectively. The results show that tomatoside A, and not the more well-known ¿-tomatine, is the predominant triterpenoidal surfactant in unripe tomato fruits.
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