A resveratrol dimer from Parthenocissus tricuspidata

Lins, Arlete Paulino; Felício, Joana D.; Braggio, Maria Maia; Roque, Luiz Carlos

doi:10.1016/s0031-9422(00)98274-8

Cited by 33 publications

(22 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…8a, A], which is consistent with the coupling pattern of tricuspidatol A (Jϭ6.0, 2.0 Hz; measured at 200 MHz). 21) Decoupling of H-7b(H-7c) causes disappearance of four main peaks (b-e) and appearance of a sharp signal (h), which proves that H-8b(H-8c) bears an AXXЈ system rather than an AX system ( 3 J AX ϭ7. 1 H-NMR Spectra (Acetone-d 6 , 600 (Fig.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 94%

“…Unfortunately, CD spectroscopic evidence has not been reported for tricuspidatol A, 20) restrytisols A and B. 21) On the other hand, a similar structure is shown by 2,5-diaryltetrahydrofuran lignan derivatives, which are prominently present in CD spectroscopic data. In the case of 2,5-diaryltetrahydrofurans bearing anti-oriented aromatic rings, the absolute con- 17) Namely, S-absolute configurations of C-2 and C-5 in the molecules will display a strong negative Cotton effect.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 98%

See 1 more Smart Citation

Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Regular ArticleDipterocarpaceaeous plants have been known to have an abundance of stilbene oligomers that have a blocking unit of resveratrol. The woody plant Vateria indica LINN. (Dipterocarpaceae) is distributed in India and Sri Lanka, and the resin has been used as a traditional medicine for sore throat, chronic bronchitis, rheumatism, and diarrhea.1) The stem of the genus Vateria is known to produce biologically active compounds such as oligostilbenoids and monoterpenes. [2][3][4][5][6] Our previous study demonstrated that the leaves also contain stilbene derivatives in high quantity. 6) Recently, the bioactivities of stilbenoids isolated from Dipterocarpaceaeous plants have been reported to have antimicrobial activites, 7,8) antitumor activities, [9][10][11] and regulation of endoplasmic reticulum stress. H COSY, and heteronuclear multiple bond connectivity (HMBC). Stereostructures were proposed by analysis of nuclear Overhauser effect spectroscopy (NOESY), differential rotating frame Overhauser enhancement (ROE), and ROESY spectra, as well as high-resolution (HR) FAB-MS and electrospray ionization (ESI)-MS analysis and circular dichroism (CD) spectroscopic properties. Vateriaphenol F (1) has a unique C 2 -symmetric structure. Results and DiscussionVateriaphenol F (1) and vaterioside A (2) were purified from an acetone extract of V. indica by open column chromatography on DMS, octadecyl silica (ODS), Silica gel, and Sephadex LH-20, as well as HPLC. Vaterioside B (4) was purified from MeOH extract by repeated chromatography.Vateriaphenol F (1) ([a] D 25 Ϫ136°), obtained as a pale-yellow solid, showed positive reaction to Gibbs reagent. The structure is composed of four resveratrol units (A-D; resveratrol A unit: i.e., between rings A 1 and A 2 via carbons C-7a and C-8a). A detailed elucidation was carried out as follows. The molecular formula was assigned to C 56 H 44 O 13 by HR-ESI-MS that showed a pseudomolecular ion [MϩNa] ϩ at m/z 947.2670, indicating 35 degrees of unsaturation. In the 1 H-and 13 C-NMR spectra at rt, some signals due to ring A 2 were broadened in various solvents. In the 1 H-NMR spectrum in acetone-d 6 at Ϫ30°C, the signals due to Pharmacognosy, Gifu Pharmaceutical University; 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan: b Institute of Microbial Chemistry, Tokyo; 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan: and c Survey of Medicinal Plant Unit, Central Council for Research in Ayurveda and Siddha; Tirunelveli-627002, Tamil Nadu, India. Received June 23, 2010; accepted July 15, 2010; published online July 16, 2010 Comprehensive re-investigation of the chemical constituents in the leaves of Vateria indica (Dipterocarpaceae) resulted in the isolation of a novel resveratrol dimeric dimer having a C 2 -symmetric structure, vateriaphenol F (1), and two new O-glucosides of resveratrol oligomers, vateriosides A (2) (resveratrol dimer) and B (4) (resveratrol tetramer), along with a new natural compound (3) and 33 known compounds including 26 resveratrol derivatives. The absolu...

show abstract

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 94%

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 98%

Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…Keywords: biomimetic synthesis · hard/soft acids · oxidation · stacking interactions · stilbene dimers the dibenzocyloheptanoid ampelopsin F (6), [7] the dibenzooctahydropentalene pallidol (7), [8] and the tetraarylfuran tricuspidatol A (8). [9] In spite of the structural diversity and attractiveness of oligostilbenoids, only very few studies were undertaken to attempt their synthesis. A recent paper by Snyder et al [10] describes elegant and versatile routes to a few dimeric species by adding and/or constructing additional rings onto a brominated stilbenes.…”

Section: Introductionmentioning

confidence: 99%

Regio‐ and Stereoselective Biomimetic Synthesis of Oligostilbenoid Dimers from Resveratrol Analogues: Influence of the Solvent, Oxidant, and Substitution

Velu

Buniyamin

Ching

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

Oligostilbenoids are polyphenols that are widely distributed in nature with multifaceted biological activities. To achieve biomimetic synthesis of unnatural derivatives, we subjected three resveratrol analogues to oligomerization by means of one-electron oxidants. Upon varying the metal oxidant (AgOAc, CuBr(2), FeCl(3)6 H(2)O, FeCl(3)6 H(2)O/NaI, PbO(2), VOF(3)), the solvent (over the whole range of polarities), and the oxygenated substitution pattern of the starting material, stilbenoid oligomers with totally different carbon skeletons were obtained. Here we propose to explain the determinism of the type of skeleton produced with the aid of hard and soft acid/base concepts in conjunction with the solvating properties of the solvents and the preferred alignment by the effect of pi stacking.

show abstract

“…The chemical shifts of the C-atoms bonded to the former H-atoms (93.39 (C(7c)), 55.54 (C(8c)), 94.55 (C(7d)), 55.00 (C(8d))) were typical for C-atoms of a dihydrobenzofuran moiety [5a], and those of the C-atoms bonded to the latter H-atoms (81.86 (C(7a)), 58.76 (C(8a)), 84.84 (C(7b)), 52.95 (C(8b))) were also similar to those of a tetrahydrofuran moiety such as that of kobophenol A (15) [10]. Several stilbene oligomers containing a tetrahydrofuran structure including 15 have been reported hitherto, and they are all resveratrol oligomers (tricuspidatol A (16) [11]; compound 17 [12]). Their relative configurations and the summarized NMR spectral data are given with their formulae in Fig.…”

mentioning

confidence: 86%

Two New Resveratrol (=5‐[(1E)‐2‐(4‐Hydroxyphenyl)ethenyl]benzene‐1,3‐diol) Tetramers with a Tetrahydrofuran Ring from Dipterocarpus grandiflorus

Ito

Tanaka

Iinuma

et al. 2004

Helvetica Chimica Acta

View full text Add to dashboard Cite

Two new stilbene tetramers, grandiphenols A (1) and B (2), along with ten known stilbene oligomers and bergenin were isolated from the stem of Dipterocarpus grandiflorus. The structures of 1 and 2 composed of four resveratrol ( 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol) units had eight asymmetric C-atoms in the partial structures of a tetrahydrofuran and two dihydrobenzofuran moieties. Detailed spectroscopic analyses, especially HMBC and NOESY experiments, allowed to differentiate the configurations of 1 and 2.

show abstract

A resveratrol dimer from Parthenocissus tricuspidata

Cited by 33 publications

References 8 publications

Chemical Constituents in the Leaves of Vateria indica

Chemical Constituents in the Leaves of Vateria indica

Regio‐ and Stereoselective Biomimetic Synthesis of Oligostilbenoid Dimers from Resveratrol Analogues: Influence of the Solvent, Oxidant, and Substitution

Two New Resveratrol (=5‐[(1E)‐2‐(4‐Hydroxyphenyl)ethenyl]benzene‐1,3‐diol) Tetramers with a Tetrahydrofuran Ring from Dipterocarpus grandiflorus

Contact Info

Product

Resources

About