Sibiraea angustata RCHD. (Rosaceae) is a shrub found at high-elevation dryland around 3000 to 4000 m height in the areas of Xizang (Tibet), Sichuan, Qinghai, Gansu and Yunnan in China. The Tibetans believe that a long-term consumption of the aerial part of S. angustata as tea has some benefit of health in humans. And they avoid mixing this plant into sheep feed, since it has been practically known to cause weight-loss during ingestion. It was no more than one of folklores before our study. These traditions were not recorded on any literature, but directly collected by our hearing from Tibetans. This folklore leads to the hypothesis that the aerial part of S. angustata might have preventive effects on obesity. Then, we had interest and study about the properties of S. angustata.In the previous studies, 43 essential oils 1) and glucityl ferulate (sibirate)2) were identified from the aerial part of S. angustata. The extract of S. angustata improved immune system 3) and prevented CCl 4 -induced liver diseases. 4) However, the active ingredients for these pharmacological effects have not yet been identified.In this study, we present the isolation and structure determination of a new compound (1), together with two known compounds, isoferulic acid and quercetin 3-O-a-L-arabinopyranosyl(1-6)-b-D-galactopyranoside 5) from the aerial part of S. angustata, and the anti-obestic effect of 1 is also discussed.
Results and DiscussionsThe aerial part of S. angustata was boiled in water and the decoction was spray dried. C-NMR and DEPT spectra suggested the presence of two tertiary methyl groups, three methylenes, seven methines, three quaternary carbons including a carbonyl group. In addition, heteronuclear single quantum correlation (HSQC) analysis suggested the presence of a methine (d C 124.1) overlapped with a signal due to the solvent (pyridine) ( Table 1).The chemical structure of the compound 1 was elucidated by 1 H-1 H correlation spectroscoopy (COSY), nuclear overhauser effect spectroscopy (NOESY), HSQC and heteronuclear multiple bond correlation (HMBC) analyses (Fig. 1). The connectives of these partial structures and the functional groups were determined by analysis of HMBC. As shown in Fig. 1, key long range correlations were observed between the following proton and carbon signals: H-1 and C-2, C-3; H-2 and C-4, C-10; H-4 (a and b) and C-3, C-6; H-6 and C-7, C-8, C-9; H-8 and C-6, C-7, C-9; H-9 and C-6, C-7, C-8; H-1Ј and C-1. Furthermore, NOESY spectrum exhibited Iskra Industry Co., Ltd.; Japan: b Graduate School of Pharmaceutical Sciences, Chiba University; Japan: and c Institute of Natural Medicine, University of Toyama; 2630 Sugitani, Toyama 930-0194, Japan. Received October 8, 2008 accepted December 19, 2008; published online January 8, 2009 A new monoterpene glycoside (1) isolated from the aerial part of Sibirae angustata RCHD. (Rosaceae) was found to be 1-O-b b-D-glucopyranosyl-geraniol-5,10-olide and named as sibiskoside. Acute toxicity study revealed that oral administration of 1 (2.5 g/kg body w...