A total of 22 triterpene glycosides, including 10 new compounds (1-10), were isolated from the underground parts of Caulophyllum thalictroides. The structures of the new glycosides were determined on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. All 22 compounds were evaluated for cytotoxicity against HL-60 human leukemia cells. The triterpene monodesmosides based on oleanolic acid (1 and 11-16) showed cytotoxic activity against HL-60 cells with IC(50) values that ranged from 3.4 to 15.9 microg/mL.

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Three new sesquiterpenoids-vetiverianines A (1), B (2), and C (3)-and a known eudesmane sesquiterpenoid (4) were isolated from the roots of Vetiveria zizanioides. Vetiverianine A (1) has a unique carbon framework comprising a rigid tricyclic ring system. Vetiverianines B (2) and C (3) are new eremophilane sesquiterpenoids. The structures of sesquiterpenoids 1-3, including the absolute configurations, were determined by NMR spectroscopic, X-ray crystallography, and vibrational circular dichroism data analysis. Vetiverianine C (3) exhibited weak cytotoxic activity against HL-60 cells.

The genus Anemone (Ranunculaceae) is taxonomically related to the genus Pulsatilla and the underground parts of several Anemone species such as Anemone tomentosa, A. japonica, and A. vififolia are used in traditional Chinese medicine as crude drug substitutes for Pulsatillae Radix (the roots of Pulsatilla chinensis).1) Previous phytochemical examinations of the roots of P. chinensis have resulted in the isolation of new triterpene glycosides based on the oleanane and lupane skeletons, some of which have showed cytotoxic activity against HL-60 human promyelocytic leukemia cells.2,3) Anemone coronaria L. is indigenous to the Mediterranean Sea coast and is cultivated for ornamental purposes around the world; it has no folkloric background. However, preliminary TLC analysis of the MeOH extract suggests that it contains numerous triterpene glycosides and a glycosideenriched fraction showed cytotoxic activity against HSC-2 human oral squamous cell carcinoma cells, which prompted us to make a phytochemical examination of the MeOH extract of A. coronaria tubers. As a result, six new triterpene glycosides (1-6), together with 11 known ones (7-17), were isolated. This paper deals with the structural determination of 1-6 on the basis of extensive spectroscopic analysis, including two-dimensional (2D) NMR, and the results of hydrolytic cleavage. In addition, the cytotoxic activity of the isolated compounds against HSC-2 cells is also described. Results and DiscussionThe glycoside-enriched fraction prepared from A. coronaria tubers (fresh weight, 3.3 kg) was subjected to column chromatography over silica gel and octadecylsilanized (ODS) silica gel, as well as preparative HPLC, giving compounds 1 (18.5 mg), 2 (46.6 mg), 3 (15.3 mg), 4 (46.5 mg), 5 (10.4 mg), 6 (10.8 mg), 7 (7.4 mg), 8 (4.2 mg), 9 (33.7 mg), 10 (36.9 mg), 11 (1.20 g), 12 (15.3 mg), 13 (624 mg), 14 (1.11 g), 15(70.5 mg), 16 (223 mg), and 17 (4.4 mg).Compounds 7-17 were identified as 3b-[(a-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid (7), Six new triterpene glycosides (1-6), together with 11 known ones (7-17), have been isolated from a glycoside-enriched fraction prepared from the tubers of Anemone coronaria L. (Ranunculaceae). On the basis of extensive spectroscopic analysis, including 2D NMR data, and the results of hydrolytic cleavage, the structures of 1-6 were determined to be 3b