Terpenoids from Eupatorium fortuneiTurcz

Abstract

Four new terpenoids, namely, rel-(1R,2S,3R,4R,6S)-p-menthane-1,2,3,6-tetrol (1), rel-(1R,2R,3R,4S,6S)-p-menthane-1,2,3,6-tetrol (2), 9-hydroxythymol 3-O-angelate (3), and (3b,20R)-20hydroxylanost-25-en-3-yl palmitate (4), together with fourteen known compounds, were isolated from the AcOEt part of the MeOH extracts of Eupatorium fortunei. In addition, two other monoterpenoids, 'acetone thymol-8,9-diyl ketal' (19) and 8-methoxy-9-hydroxythymol 3-O-angelate (20) were also obtained which were probably artifacts but have never been reported in the literature. The structures of the new compounds, including their relative configurations, were established by an extensive study of their spectral data, especially 1D-and 2D-NMR. The cytotoxic activity of the new compounds against human hepatoma (SMMC-7721), human leukemia (HL-60), and human hepatocyte (LO 2 ) cells was investigated.1. Introduction. -The genus Eupatorium (Compositae) consists of about 1200 species, with 14 species widely distributed in China [1], of which 8 species have long been used as Chinese folk medicines [2], especially Eupatorium fortunei. This species has been used as a diuretic and detoxifying drug [3] in China for the treatment of a dropsy, chill, and fever. In continuation of our search for bioactive compounds from species of the family of Compositae [4] [5], we studied the whole plant of E. fortunei. The petroleum ether, AcOEt, and BuOH extracts of the initially obtained MeOH extract of E. fortune were firstly tested for their antitumor activities against human hepatoma (SMMC-7721) and human leukemia (HL-60) cells, establishing cytotoxicity of the AcOEt extract (see below, Table 3). Therefore, we investigated the AcOEt extract and succeeded isolating of four new terpenoids 1 -3 and 4, together with the fourteen known compounds 5 -18. Furthermore, two new monoterpenoids, 19 and 20, were also obtained which were probably artifacts. These new compounds were investigated for the cytotoxic activities against SMMC-7721, HL-60, and human hepatocyte (LO 2 ) cells, revealing that compounds 1, 2, 19, and 20 were cytotoxic against HL-60 cell. We report here on the isolation and structural elucidation of these compounds and the cytotoxicity-assay results. Results andDiscussion. -The known compounds were identified by comparing their spectral data (MS, IR, 1 H-and 13 C-NMR) with those reported in the literature, i.e., as thymol (= 5-methyl-2-(1-methylethyl)phenol; 5) [6], 7-hydroxythymol (= 5-(hydroxymethyl)-2-(1-methylethyl)phenol; 6) [7] [8], 9-hydroxythymol (= 2-(2-hy-

New monocyclic monoterpenoid glycoside from Mentha haplocalyxBriq.

“…The relative configuration at C(1) was determined from ROESY correlation of δ 1.21 (Me(7)) with H-2 ( δ 3.33). It was in good agreement with those of rel- (1 R ,2 S ,3 R ,4 R ,6 S ) p -menthane-1,2,3,6-tetrol [8]. Therefore 1 should possess rel -(1 R ,2 S ,3 R ,4 R )-configuration.…”

“…The 1 H- and 13 C-NMR spectral data displayed the presence of two secondary methyl δ 0.81 (3H, d J  = 7.0 Hz, H-10), 0.92 (3H, d J  = 7.0 Hz, H-9)], a tertiary methyl δ 1.21 (3H, s , H-7)], two methylenes δ 1.37 (2H, dt J  = 11.7, 8.3 Hz, H-5), 1.40 (1H, m, H-6α) and 1.57 (1H, m, H-6β)], four methines (two of them was oxygenated) δ 3.82 (1H, d J  = 10.8, 9.2 Hz, H-3), 3.33 (1H, d J  = 10.8 Hz, H-2), 2.31 (1H, m, H-8), and 1.69 (1H, m, H-4)], and an oxygentated quaternary carbon, suggesting that compound 1 was a menthane-type monoterpene with three OH-groups [7,8]. Moreover, 1 H- 1 H COSY correlations were observed between H-C(9)/H-C(8)/H-C(10), H-C(8)/H-C(4), and H-C(6)/H-C(5)/H-C(4)/H-C(3)/H-C(2), that the deduced spin system implied that the three OH-groups were located at C(1), C(2) and C(3) in 1, respectively.…”

Chemical constituents from the flower of Datura metel L.

“…Compounds 2-6 were identified as grasshopper ketone (3S,5R,8R)-3,5-dihydroxy megastigma-6,7-dien-9-one (Jiang et al, 2006), citroside A [(3S,5R,8R)-3,5-dihydroxymega stigma-6,7-dien-9-one-3-O-β-D-glucopyranoside (Wang et al, 2005), vomifoliol [(6S,9R) 6-hydroxyl-3-oxo-α-ionol] (Otsuka et al, 1995), (6S,9R)-3-oxo-α-ionol-9-O-β-Dglucopyranoside (Dwivedi et al, 1991), and (6S,9R)-3-oxo-α-ionol-9-O-β-D-glucopyranoside (Otsuka et al, 1995) with the help of spectroscopic techniques, respectively. Their 1 H-NMR and 13 C-NMR data were in agreement with the ones reported in the literature.…”

Reduction of metastatic and angiogenic potency of malignant cancer by Eupatorium fortunei via suppression of MMP-9 activity and VEGF production

“…Additionally, p- cymene and neryl acetate, major components of E. fortunei , have been reported to possess anti-influenza activity. In a recent study, it was demonstrated that the ethyl acetate fraction of a methanol extract of E. fortunei exhibited cytotoxicity against human leukemia (HL-60) cells 20 .…”