Abstract
Siamenoside I is the sweetest mogroside that has several kinds of bioactivities, and it is also a constituent of Siraitiae Fructus, a fruit and herb in China. Hitherto the metabolism of siamenoside I in human or animals remains unclear. To reveal its metabolic pathways, a high-performance liquid chromatography-electrospray ionization-ion trap-time of flight-multistage mass spectrometry (HPLC-ESI-IT-TOF-MSn) method was used to profile and identify its metabolites in rats. Altogether, 86 new metabolites were identified or tentatively identified, and 23 of them were also new metabolites of mogrosides. In rats, siamenoside I was found to undergo deglycosylation, hydroxylation, dehydrogenation, deoxygenation, isomerization, and glycosylation reactions. Among them, deoxygenation, pentahydroxylation, and didehydrogenation were novel metabolic reactions of mogrosides. The distributions of siamenoside I and its 86 metabolites in rat organs were firstly reported, and they were mainly distributed to intestine, stomach, kidney, and brain. The most widely distributed metabolite was mogroside IIIE. In addition, eight metabolites were bioactive according to literature. These findings would help to understand the metabolism and effective forms of siamenoside I and other mogrosides in vivo.
Highlights
Mogrosides are a group of cucurbitane-type triterpenoid saponins which have the common aglycone of mogrol [1]
86 new metabolites of siamenoside I were detected in different biological samples from rats, and nine of them were unambiguously identified by comparison with reference compounds, and the others were tentatively identified by careful interpretation of their LC-MSn data
23 metabolites (M6, M7, M13, M14, M22, M23, M26-M28, M30, M62-M65, M78–M86) are firstly reported as new metabolites of mogrosides. These results suggest that siamenoside I has its own metabolism characteristics in comparison with mogroside V
Summary
Mogrosides are a group of cucurbitane-type triterpenoid saponins which have the common aglycone of mogrol [1]. They are responsible for the sweet taste and bioactivities of Siraitiae Fructus (Luo Han Guo in Chinese, the ripe fruits of Siraitia grosvenorii), a traditional Chinese medicine and an edible fruit [2]. Siamenoside I is one of the mogrosides, which is firstly isolated from Siraitia siamensis (a Chinese folk medicine) [3] and from Siraitia grosvenorii [4]. Besides its intense sweet taste, siamenoside I has several kinds of bioactivities. It can inhibit the induction of Epstein–Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate
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