Novel oligostilbenes from Vitis coignetiae

Oshima, Yoshiteru; Kamijou, A.; Ohizumi, Yasushi; Niwa, Masayuki; Itô, Junko; Hisamichi, Kanehiko; Takeshita, Mitsuhiro

doi:10.1016/0040-4020(95)00757-y

Cited by 45 publications

(32 citation statements)

References 5 publications

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“…Comparing the NMR data of the isolated metabolites with the previously reported has confirmed their identities as (+)-ampelopsin A ( 1 ), (+)-hopeaphenol ( 2 ) and (+)-vitisin A ( 3 ) [14,16,17]. The NMR data of compound ( 4 ) matched with the reported data for vitisin B [18], however it showed positive optical rotation indicating its identity as the (+)-enantiomer of vitisin B ( 4 ).…”

Section: Methodssupporting

confidence: 80%

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Antibacterial Activities of Metabolites from Vitis rotundifolia (Muscadine) Roots against Fish Pathogenic Bacteria

et al. 2018

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Enteric septicemia of catfish, columnaris disease and streptococcosis, caused by Edwardsiella ictaluri, Flavobacterium columnare and Streptococcus iniae, respectively, are the most common bacterial diseases of economic significance to the pond-raised channel catfish Ictalurus punctatus industry. Certain management practices are used by catfish farmers to prevent large financial losses from these diseases such as the use of commercial antibiotics. In order to discover environmentally benign alternatives, using a rapid bioassay, we evaluated a crude extract from the roots of muscadine Vitis rotundifolia against these fish pathogenic bacteria and determined that the extract was most active against F. columnare. Subsequently, several isolated compounds from the root extract were isolated. Among these isolated compounds, (+)-hopeaphenol (2) and (+)-vitisin A (3) were found to be the most active (bacteriostatic activity only) against F. columnare, with 24-h 50% inhibition concentrations of 4.0 ± 0.7 and 7.7 ± 0.6 mg/L, respectively, and minimum inhibitory concentrations of 9.1 ± 0 mg/L for each compound which were approximately 25X less active than the drug control florfenicol. Efficacy testing of 2 and 3 is necessary to further evaluate the potential for these compounds to be used as antibacterial agents for managing columnaris disease.

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Section: Methodssupporting

confidence: 80%

“…For 1 H and 13 C-NMR data, see Supporting Information [18]. High-resolution ESI/MS: m/z 930.26734 [M + Na + H] 2+ ; calculated for C 56 H 43 NaO 12 , 930.26522.…”

Section: Methodsmentioning

confidence: 99%

Antibacterial Activities of Metabolites from Vitis rotundifolia (Muscadine) Roots against Fish Pathogenic Bacteria

et al. 2018

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“…Isolation of resveratrol tetramers was performed using methods described previously (Oshima et al, 1995a;Ito et al, 1999). In brief, dried corks of Vitis vinifera and stems of Vitis coignetiae (Vitaceae) were extracted with methanol and acetone, respectively, at room temperature to yield methanol and acetone extracts.…”

Section: Methodsmentioning

confidence: 99%

“…In the last 3 decades, we have extracted and purified various novel oligostilbenes that are resveratrol tetramers from the genus Vitis (Oshima et al, 1995a;Ito et al, 1998Ito et al, , 1999. Some pharmacological properties of resveratrol tetramers such as anti-inflammatory and/or hepatoprotective effects have been reported (Oshima et al, 1993(Oshima et al, , 1995bHuang et al, 2001).…”

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confidence: 99%

Opposite Effects of Two Resveratrol (trans-3,5,4′-Trihydroxystilbene) Tetramers, Vitisin A and Hopeaphenol, on Apoptosis of Myocytes Isolated from Adult Rat Heart

Seya¹,

Kanemaru²,

Sugimoto³

et al. 2008

J Pharmacol Exp Ther

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It has been reported that resveratrol (trans-3,5,4Ј-trihydroxystilbene) from Vitis plants has various cardioprotective effects. Vitis plants also include various resveratrol tetramers. The aim of our study is to clarify the pharmacological properties of resveratrol tetramers. We isolated two resveratrol tetramers as major products of Vitis plants. One is vitisin A, a complex of two resveratrol dimers, (ϩ)--viniferin and ampelopsin B, and the other is hopeaphenol, composed of 2 mol ampelopsin B. Vitisin A (30 -300 nM) unexpectedly dose-dependently facilitated swelling and depolarization of mitochondria and cytochrome c release from mitochondria, which are indices of cardiomyocyte apoptosis. Furthermore, vitisin A induced apoptosis in the primary culture of adult rat ventricular myocytes. On the other hand, hopeaphenol (1-10 M) dose-dependently inhibited Ca 2ϩ (30 M)-induced mitochondrial depolarization and cytochrome c release from mitochondria but had not affected mitochondrial swelling. Moreover, hopeaphenol inhibited vitisin A-induced apoptosis. In structural and functional studies, we further confirmed that vitisin B, one of the resveratrol tetramers having (ϩ)--viniferin unit, induces mitochondrial swelling and cytochrome c release from mitochondria like vitisin A and that vitisifuran A, one of the resveratrol tetramers having the ampelopsin B unit, inhibits Ca 2ϩ -induced cytochrome c release from mitochondria like hopeaphenol. These results show that resveratrol tetramers have at least two opposite effects on cardiomyocytes; the one having the (ϩ)--viniferin unit induces cardiomyocyte apoptosis, and the other having ampelopsin B but not (ϩ)--viniferin unit inhibits it.

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“…The 1 H NMR spectral data also showed the presence of a set of methine aliphatic protons at d H 5.10/3.36 (H-7a/H-8a) belonging to a unit of 1,2-dihydrobenzofuran moiety, and a set of methine aliphatic protons in AX spin system with multiplicity of double doublet at d H 5.20/3.56 (H-7b/H8b) for CHZCHZX unit. The characteristic of this unit structure suggested a similar skeleton as dimer oligostilbenoid, 1-viniferin diol [8] or betulifol B [9]; however, the presence of two sets of double doublet aliphatic signals in AX spin system suggested a symmetrical element in the molecule of 1. To prove our observation, we further analyzed the HMBC and NOE correlations of 1.…”

Section: Resultsmentioning

confidence: 96%

A new symmetrical tetramer oligostilbenoid containing tetrahydrofuran ring from the stem bark ofDryobalanops lanceolata

Ahmat

Wibowo

Mohamad

et al. 2014

Journal of Asian Natural Products Research

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A new tetramer oligostilbenoid possessing tetrahydrofuran ring, malaysianol C (1), was isolated from the acetone extract of the stem bark of Dryobalanops lanceolata, together with four known oligostilbenoids nepalensinol E (2), ϵ-viniferin (3), laevifonol (4), and ampelopsin F (5). The structures of isolated compounds were elucidated on the basis of spectral evidence. The antibacterial activity of the isolated compounds was evaluated using resazurin microtitre-plate assay, whereas the cytotoxic activity was tested using MTT assay. The plausible biogenetic routes of the isolated compounds are also discussed.

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Novel oligostilbenes from Vitis coignetiae

Cited by 45 publications

References 5 publications

Antibacterial Activities of Metabolites from Vitis rotundifolia (Muscadine) Roots against Fish Pathogenic Bacteria

Antibacterial Activities of Metabolites from Vitis rotundifolia (Muscadine) Roots against Fish Pathogenic Bacteria

Opposite Effects of Two Resveratrol (trans-3,5,4′-Trihydroxystilbene) Tetramers, Vitisin A and Hopeaphenol, on Apoptosis of Myocytes Isolated from Adult Rat Heart

A new symmetrical tetramer oligostilbenoid containing tetrahydrofuran ring from the stem bark ofDryobalanops lanceolata

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