Stilbenes and oligostilbenes from leaf and stem of Vitis amurensis and their cytotoxic activity

Abstract

Chromatographic separation of the EtOAc fraction from the leaf and stem of Vitis amurensis led to the isolation of six oligostilbenoids (i.e., r-2-viniferin (1), trans-amurensin B (2), trans-epsilon-viniferin (3), gnetin H (4), amurensin G (5), (+)-ampelopsin A (8)) and four stilbenoids (i.e., trans-resveratrol (6), (+)-ampelopsin F (7), piceatannol (9), and trans-piceid (10)). The structures have been identified on the basis of spectroscopic evidence and physicochemical properties. The isolates were investigated for cytotoxic activity against three cancer cell lines in vitro using the MTT assay method. Amurensin G (5) and trans-resveratrol (6) showed significant cytotoxic activity against L1210, K562 and HTC116 cancer cell lines with IC(50) values ranging from 15.7 +/- 2.1 to 30.9 +/- 1.8 microM. (+)-Ampelopsin A (8) and trans-piceid (10) exhibited considerable cytotoxic activity against L1210 (IC(50) values of 30.6 +/- 4.1 and 28.7 +/- 2.81 microM, respectively) and K562 (IC(50) values of 38.6 +/- 0.82 and 24.6 +/- 0.76 microM, respectively). Gnetin H (4) showed only weak cytotoxic activity against L1210 with an IC(50) value of 40.1 +/- 4.23 microM. On the other hand, r-2-viniverin (1), trans-amurensin B (2), trans-epsilon-viniferin (3), (+)-ampelopsin F (7), and piceatannol (9) exhibited no activity on three cancer cell lines.

Leaf and stem of Vitis amurensis and its active components protect against amyloid β protein (25–35)-induced neurotoxicity

“…The purification of Fr. 4.3.4 (2.1 g) using MPLC (ODS column 25 × 300 mm, flow rate 4 mL/min, detection at 254 nm) with MeOH-H 2 O (1:2) as the eluent gave amurensin G (500 mg) (Ha et al, 2009a). The structures of amurensin G, r-2-viniferin and trans-ε-viniferin are shown in Fig.…”

“…In cultures treated with V. amurensis extract (5 or 10 µg/mL), the Aβ (25-35)-induced neuronal death was significantly reduced (absorbance, 77.2 ± 3.1% of control with 10 µg/mL V. amurensis). To determine which components of V. amurensis exhibit neuroprotective activity, we examined all of the stilbenes and oligostilbenes isolated from V. amurensis in our previous study (Ha et al, 2009a(Ha et al, , 2009b. Of these components, amurensin G, r-2-viniferin and trans-ε-viniferin protected against Aβ (25-35)-induced neurotoxicity in cultured cortical neurons.…”

“…Recently, the root and stem of V. amurensis have been reported to possess anti-inflammatory and anti-tumor activities and neuroprotective effect against β-amyloid-induced oxidative stress in cell cultures (Huang et al, 2001;Lee et al, 2006;Jang et al, 2007) and to contain a wide variety of structurally diverse resveratrol oligomers (Huang et al, 2000(Huang et al, , 2001. Studies on the chemical substances and pharmacological activities of the leaf and stem of V. amurensis have isolated eleven resveratrols, including stilbenes and oligostilbenes, which have antioxidant and antiinflammatory effects and cytotoxic activity when assayed using cancer cell lines in vitro (Ha et al, 2009a(Ha et al, , 2009bYim et al, 2010). Since oxidative stress has been shown to precede the formation of senile plaques (Petersen et al, 2007) and inflammatory responses may significantly contribute to the progression of AD (Heneka and O'Banion, 2007), free radical scavengers and anti-inflammatory agents have attracted considerable attention as potential neuroprotective agents in AD.…”

Greater Effectiveness of ε-Viniferin in Red Wine Than Its Monomer Resveratrol for Inhibiting Vascular Smooth Muscle Cell Proliferation and Migration

“…15) Several biological functions of "-viniferin have so far been demonstrated; for example, "-viniferin exhibited hepatoprotective activity in cultured rat hepatocytes, 17) and had a potent inhibitory effect against lipoxygenase and the oxidation of low-density lipoprotein and highdensity lipoprotein. 18,19) Resveratrol and its oligomers, including "-viniferin, have also been suggested to show anti-proliferative and pro-apoptotic effects on cancer cells such as human and murine leukemia cells, [20][21][22] human hepatoma HepG2 cells, 23) and human colon cancer cells. 22,24,25) Although "-viniferin was ineffective or less effective than resveratrol towards these cancer cells, [20][21][22][23][24][25] it was more effective than resveratrol in inducing the relaxation of isolated rat thoracic aorta preparations.…”

Generation and Analysis of ESTs in <i>V. amurensis</i> Grapevine Pericarp at Veraison

“…Grape berries are processed into wine, produced commercially for fresh consumption, dried into raisins, processed into non-alcoholic juice and distilled into spirits (Lund et al, 2008). As one of the most important wild germplasm resources, V. amurensis (Amur grape) is widely distributed in China, Korean and Japan (Ha et al, 2009). It is very resistant to frost, withstanding temperature as low as -40℃, but it is not tolerant to drought.…”