Novel resveratrol tetramer, vaticaffinol, from Vatica affinis Thw. (dipterocarpaceae)

Sultanbawa, M. Uvais S.; Surendrakumar, Sivaguanasundram; Wazeer, Mohamed I. M.; Bladon, Peter

doi:10.1039/c39810001204

Cited by 25 publications

(21 citation statements)

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“…Vateriaphenol F (1) has the same partial structure as (Ϫ)-e-viniferin (10), 16) the main constituent of this substance. From the viewpoint of biogenetic pathways, 10 could be a precursor of 1 and the configuration of corresponding carbons of 1 (C-7a, C-8a, C-7d, and C-8d) are all absolute R configurations.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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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...

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Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…7). NOE interactions were observed between H-Glc2-1/H-8b and H-7b/H-14b, while NOEs for H-Glc2-1/H-7b and H-8b/H-14b were absent, indicating the necessity of an anti-orientation of two methine protons (H-7b and H- (19) would generate equilibrium radicals (D-F), where D, E, and F bear each radical on positions C-12b, C-10b, and C-14b, respectively. Radical (F) reacts with B to afford 3.…”

Section: Resultsmentioning

confidence: 95%

“…In the NOESY spectrum, NOEs were observed between H2a(6a)/H-8a, H-2a(6a)/H-14a, and H-7a/H-14a, confirming the trans orientation of the two methine protons (H-7a and H-8a). The aglycone can be regarded as the condensation product of a resveratrol dimer [3A; e-viniferin 19) ] and a resveratrol monomer (3B). The configuration of 3B and the stereochemical relationship between 3A and 3B was determined by NOESY spectral analysis together with consideration of anisotropy.…”

Section: Resultsmentioning

confidence: 99%

Occurrence of C-Glucoside of Resveratrol Oligomers in Hopea parviflora

Abe

Ito

Oyama

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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The new structures have a common partial structure of the 1-hydroxy-1-(3,5-dihydroxy-2-C-glucopyranosylphenyl)-2-(4-hydroxyphenyl)ethane-2-yl group after oxidative condensation of (E)-resveratrol-10-C-b b-glucopyranoside (14). The structures were determined by spectroscopic analysis including 2D-NMR and computeraided molecular modeling. The biogenetic relationship of the isolates and NMR characteristics caused by steric hindrance are also discussed in this paper.

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“…Stilbene dimmer that contain stilbene skeleton is ε-viniferin (3), which is a precursor to other oligostilbenoids [39] and was isolated from V. affinis [40], V. rassak [35], V. pauciflora [30,31], V. umbonata [39], V. albiramis [37] and V. odorata [38]. The isomer, (Z)-ε-viniferin (9) was isolated from V. albiramis [37].…”

Section: Stilbene Dimmermentioning

confidence: 99%

“…The first group is symmetrical stilbene and the second group is unsymmetrical stilbene. The constituents that fall in the first group are hopeaphenol (42) from V. umbonata [39], V. albiramis [37] and V. odorata [38]; hopeaphenol A (43) and isohopeaphenol A (44) from V. oblongifolia [48]; pauciflorol C (45) and vateriaphenol B (46) from V. pauciflora [31]; stenophyllol C (47) and vatalbinoside A (48) from V. albiramis [37] as well as vaticaffinol (49) from V. affinis [40].…”

Section: Stilbene Tetramermentioning

confidence: 99%

Oligostilbenoids from Vatica Species and Bioactivities

Kamarozaman

Rajab²,

Latip³

2014

Recent Trends in Physics of Material Science and Technology

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Reactive species (RS) which are generated from the pollution, deep fried and spicy foods, leakage of electrons from mitochondrial electron transport chains etc. may result in an oxidative damage in the body. The oxidative damage may lead to various diseases such as Alzheimer, atherosclerosis and cancer. In order to prevent such diseases, antioxidants play important roles in reducing the powerful oxidizing agents. Vatica species that belongs to the family of Dipterocarpaceae has been widely known to contain abundant source of oligostilbenoids which demonstrated interesting result in biological activities such as anticancer and antioxidant. This may lead to a development of drugs as well as natural antioxidants. In this chapter, we are highlighting the oligostilbenoids isolated from Vatica species from various researcher as well as the biological activities.

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Novel resveratrol tetramer, vaticaffinol, from Vatica affinis Thw. (dipterocarpaceae)

Cited by 25 publications

References 0 publications

Chemical Constituents in the Leaves of Vateria indica

Chemical Constituents in the Leaves of Vateria indica

Occurrence of C-Glucoside of Resveratrol Oligomers in Hopea parviflora

Oligostilbenoids from Vatica Species and Bioactivities

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