Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F

Takaya, Yoshiaki; Yan, Ke-Xu; Terashima, Kenji; Itô, Junko; Niwa, Masayuki

doi:10.1016/s0040-4020(02)00785-8

Cited by 75 publications

(60 citation statements)

References 9 publications

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“…The 13 C-NMR spectra showed twenty eight carbon signals comprising one oxygenated methine carbon at G 88.4 (C-7), one aliphatic methylene carbon at G 33.9 (C-8'), two aliphatic methine carbons at G 35.7 (C-7') and 49.4 (C-8), together with six quaternary carbons at G 131.1 (C-1), 134.8 (C-9), 122.9 (C-14), 138.2 (C-1'), 142.7 (C-9'), and 119.1 (C-10'), six oxygenated aromatic carbons at G 158.8 (C-4), 156.2 (C-11), 158.6 (C-13), 156.6 (C-4'), 157.2 (C-11') and 160.5 (C-13'), and twelve aromatic carbons. These data alluded that 13 was a dimer resveratrol derivative, and in comparison with those of published data and the structure of 13 was identified as ampelopsin B (Keckei et al, 2000;Takaya et al, 2002). This is the first occurrence of ampelopsin B from rhubarb.…”

Section: Resultssupporting

confidence: 55%

Lipoxygenase inhibitory constituents from rhubarb

et al. 2008

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Phytochemical study on the ethanol extract of rhubarb led to the isolation of fifteen compounds, including five anthraquinones: chrysophanol (1), physcion (2), emodin (7), chrysophanol-8-O-beta-D: -glucopyranoside (9) and emodin-8-O-beta-D: -glucopyranoside (15), and ten stilbenes: desoxyrhaponticin (3), rhaponticin (4), resveratrol (5), desoxyrhapotigenin (6), rhapontigenin (8), piceatannol-3'-O-beta-D: -glucopyranoside (10), piceid (11), epsilon-viniferin (12), ampelopsin B (13) and isorhaponticin (14). Their structures were identified by comparing the physicochemical data with those of published papers. Among the isolated compounds, stilbene derivatives (3-6, 8 and 10-14) showed remarkable inhibitory effect on lipoxygenase with IC(50) values ranging from 6.7 to 74.1 microM. The inhibition kinetics analyzed by Lineweaver-Burk plots found that they were competitive inhibitors with the linoleic acid at the active site of lipoxygenase. In addition, stilbenes exhibited significantly free radical scavenging activity against ABTS(.+) with trolox equivalent activity capacity (TEAC) values ranging from 1.16 to 4.64. Whereas, anthraquinone derivatives (1-2, 7, 9 and 15) neither inhibited lipoxygenase nor scavenged free radical ABTS(.+). These results indicated that stilbene derivatives were considerate to be mainly lipoxygenase inhibitor and free radical scavenger constituents of rhubarb.

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Section: Resultssupporting

confidence: 55%

Lipoxygenase inhibitory constituents from rhubarb

et al. 2008

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“…The structures of the isolated compounds were identified by comparing their spectral λ max MeOH data ( 1 H-, and 13 C-NMR) to those reported in the literature. They were identified to be r-2-viniferin (1) , trans-amurensin B (2) , trans-ε-viniferin (3) (Li et al, 1996), gnetin H (4) (Kim et al, 2002a), amurensin G (5) , resveratrol (6) (Jin et al, 2002), (+)-ampelopsin F (7) (Takaya et al, 2002), (+)-ampelopsin A (8) (Kulesh et al, 2006;Tanaka et al, 2000;Ito et al, 1998;Li et al, 1996), piceatannol (9) (Vastano et al, 2000), and trans-piceid (10) (Terguo et al, 1996). Of these, compounds 1, 2, 4, 5, and 7 were isolated for the first time from the leaf and stem of Vitis amurensis.…”

Section: Resultsmentioning

confidence: 99%

“…Hz, H-2a, 6a); 13 C-NMR (75 MHz, Acetone-d 6 ) δ: 37.6 (C-7b), 48.9 (C-8a), 52.5 (C8b), 57.4 (C-8c), 62.1(C-7c), 90.6 (C-7a), 96.7 (C-12b), 101.7 (C-12c), 101.9 (C-12a), 105.9 (C-14a), 105.9 (C14c), 107.5 (C-10c), 115.6 (C-3b, 5b), 115.9 (C-3c, 5c), 116.1 (C-3a, 5a), 116.1 (C-10b), 121.1 (C-14b), 124.8 (C10a), 130.0 (C-2c, 6c), 130.3 (C-2a, 6a), 130.6 (C-2b, 6b), 130.8 (C-1a), 132.8 (C-1c), 133.4 (C-1b), 141.7 (C9a), 144.2 (C-9b), 146.9 (C-9c), 154.8 (C-13b), 155.9 (C4b), 155.9 (C-11a), 156.9 (C-4c), 156.9 (C-13a), 158.7 (C-4a), 159.3 (C-11c), 159.3 (C-13c), 159.5 (C-11b) . C-3b, 5b), 115.9 (C-3a, 5a), 128.9 (C-10a), 129.5 (C-2b, 6b), 130.2 (C-2a, 6a), 136.3 (C-10a), 139.2 (C-1a), 147.9 (C-9a), 147.6 (C-9b), 153.3 (C-11a), 156.2 (C-4a), 156.2 (C-4b), 157.3 (C-13b), 158.2 (C-11b), 158.6 (C-13a) (Takaya et al, 2002). .…”

Section: Extraction and Isolation Processmentioning

confidence: 99%

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

Chen

Hung

et al. 2009

Arch. Pharm. Res.

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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.

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“…The structures of 10 known compounds were identified by comparing their physico-chemical and spectroscopic data with those published in literatures as piceatannol (1) (Vastano et al, 2000), (+)-ampelopsin A (2) (Takaya et al, 2002), (+)-ampelopsin F (3) (Tanaka et al, 1998), trans-reveratrol (4) (Jin et al, 2002), amurensin G (5) (Huang et al, 1999b), trans--viniferin (6) (Li et al, 1996), gnetin H (7) (Kim et al, 2002), r-2-viniferin (8) (Korhammer et al, 1995), trans-amurensin B (10) (Huang and Lin, 1999), and trans-piceid (11) (Terguo et al, 1996) (Fig. 1A).…”

Section: Structures Of Isolated Oligostilbenesmentioning

confidence: 99%