Five New Oligostilbenes with One or Two Dihydrofurans from the Stem Bark of Vatica rassak

Ito, Tetsuro; Tanaka, Toŝhiyuki; Ido, Yoshimi; Nakaya, Ken‐ichi; Iinuma, Munekazu; Takahashi, Yoshikazu; Naganawa, Hiroshi; Riswan, Soedarsono

doi:10.3987/com-00-9139

Cited by 34 publications

(28 citation statements)

References 5 publications

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“…[10][11][12][13][14][15][16][17] Melanoxylin A ( Bioassay Methods. Animals Male ddY mice and Wistar rats were purchased from Kiwa Laboratory Animal Co., Ltd. (Wakayama, Japan).…”

Section: Methodsmentioning

confidence: 99%

“…The EtOAc-soluble fraction from the wood was subjected to normal-and reversed-phase column chromatography and finally to HPLC to yield a new stilbene dimer, melanoxylin A (1, 0.0036%), together with four known stilbene derivatives, vaticanol G (5, 28.0%), 10) (ϩ)-ampelopsin F (6, 0.131%), 11) (ϩ)-isoampelopsin F (7, 0.0045%), 12) and (ϩ)-e-viniferin (8, 0.057%), 13) and a lignan, (ϩ)-lyoniresinol (10, 0.0062%). 14) In the same manner, a new stilbene trimer, melanoxylin B (2, 0.0032%), five known stilbene derivatives, vaticanols A (3, 2.0%), 15) E (4, 2.9%), 16) and G (5, 7.3%), (ϩ)-e-viniferin (8, 0.10%), and cis-(ϩ)-e-viniferin (9, 0.0034%), 17) and an aromatic compound, p-hydroxybenzoic acid (0.0044%), were obtained from the MeOH extract from the bark of C. melanoxylon. (Fig.…”

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Antidiabetogenic Constituents from the Thai Traditional Medicine Cotylelobium melanoxylon

et al. 2009

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The methanolic extracts from the wood and bark of Cotylelobium melanoxylon were found to inhibit plasma glucose elevation after sucrose loading in rats and triglyceride elevation after olive oil loading in mice. (vaticanols A, E, and G) were isolated from the bark extract of C. melanoxylon. The principal constituents, vaticanols A, E, and/or G, inhibited plasma glucose and triglyceride elevation after sucrose loading in rats and olive oil loading in mice, respectively. In addition, vaticanols A, E, and/or G inhibited the enzyme activities of rat intestinal a a-glucosidase, porcine pancreatic lipase, and rat lens aldose reductase.

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“…[10][11][12][13][14][15][16][17] Melanoxylin A ( Bioassay Methods. Animals Male ddY mice and Wistar rats were purchased from Kiwa Laboratory Animal Co., Ltd. (Wakayama, Japan).…”

Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Antidiabetogenic Constituents from the Thai Traditional Medicine Cotylelobium melanoxylon

et al. 2009

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“…In addition to the four new O-glucosides of stilbene oligomer, 1 and 5 ± 7, three known glucosides were isolated and identified as vaticasides B (3), C (4) [15], and paucifloroside A (8) [8].…”

Section: The Hr-fab-ms ([M à H]mentioning

confidence: 99%

Occurrence of Stilbene Glucosides in Upuna borneensis

Ito

Ali

Iliya

et al. 2005

Helvetica Chimica Acta

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Four new stilbene glucosides, upunosides A (1), B (5), C (6), and D (7), were isolated from the stem of Upuna borneensis (Dipterocarpaceae) together with the three known glucosides 3, 4, and 8. Upunoside A (1) is the first natural instance of a glucoside of a resveratrol pentamer, and its aglycone has a dibenzo-fused bicyclo[5.3.0]octadiene and two dihydrobenzofuran moieties. The relative structure of the aglycone was determined by spectral analysis including 1D and 2D NMR experiments.

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“…30) 2-b-glucopyranosyloxyphenanthrene-4,6-diol (9), 31) paucifloroside A (11), 23) cis-(Ϫ)-eviniferin (12), 32) upunoside D (13), 33) balanocarpol (14), 34) melanoxylin A (15), 35) malibatol (16), 36) (Ϫ)-ampelopsin F (17), 37) pauciflorol B (18), 23) vaticanol C (20), 38) hemsleyanols C (21) and D (22), 39) pauciflorol C (23), 23) vateriaphenol B (24), 4) nepalensinol G (25), 40) stenophyllol A (26), 41) vaticanol B (27), 38) vaticasides B (28) and C (29), 42) and upunaphenol F (30). 43) The other known compounds were identified to be flavonols [kaempferol 3-O-rhamnoside (31), 44) kaempferol 3-O-rhamnopyranosyl-(1→2)-rhamnopyranoside (32), and quercitrin (33) 45) ], diterpenes [columbin (34) 46) and palmarin (35) 47) ], bergenin (36), 11) and syringin (37).…”

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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Five New Oligostilbenes with One or Two Dihydrofurans from the Stem Bark of Vatica rassak

Cited by 34 publications

References 5 publications

Antidiabetogenic Constituents from the Thai Traditional Medicine Cotylelobium melanoxylon

Antidiabetogenic Constituents from the Thai Traditional Medicine Cotylelobium melanoxylon

Occurrence of Stilbene Glucosides in Upuna borneensis

Chemical Constituents in the Leaves of Vateria indica

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