Ellagic compounds from Diplopanax stachyanthus

Khac, Duc Do; Tran-Van, Sung; Campos, Angela Martha; Lallemand, Jean‐Yves; Fétizon, M.

doi:10.1016/0031-9422(90)89044-a

Cited by 82 publications

(57 citation statements)

References 17 publications

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“…Negative ESIMS: m/z 169 [M -1] − ; 1 H and 13 C NMR data are consistent with previously published data (Khac, Tran-Van, Campos, Lallemand & Fetizon, 1990). The compound was also identified by HPLC-PDA analysis (retention time and UV spectrum) with authentic standard.…”

Section: Isolation and Purificationsupporting

confidence: 70%

Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

et al. 2008

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Bioassay-guided fractionation of the methanolic extracts of the pulp and seeds of the fruits of Syzygium samarangense Merr. & Perry (Blume) led to the identification of four cytotoxic compounds and eight antioxidants on the basis of HPLC-PDA analysis, MS, and various NMR spectroscopic techniques. Three C-methylated chalcones, 2′,4′-dihydroxy-3′,5′-dimethyl-6′-methoxychalcone (1), 2′,4′-dihydroxy-3′-methyl-6′-methoxychalcone (stercurensin, 2), and 2′,4′-dihydroxy-6′-methoxychalcone (cardamonin, 3), were isolated and displayed cytotoxic activity (IC 50 = 10, 35, and 35 μM, respectively) against the SW-480 human colon cancer cell line. Also a number of known antioxidants were obtained including six quercetin glycosides: reynoutrin (4), hyperin (5), myricitrin (6), quercitrin (7), quercetin (9), and guaijaverin (10), one flavanone: (S)-pinocembrin (8), and two phenolic acids: gallic acid (11) and ellagic acid (12).

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Section: Isolation and Purificationsupporting

confidence: 70%

Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

et al. 2008

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“…3). Structures of the isolates were identified by comparison of NMR and mass spectra with data from the literature (1 8 , 2 15 , 3 16 , 4 17 , 5 16 , 6 16 ).…”

Section: Resultsmentioning

confidence: 99%

Phytotoxic Allelochemicals From Roots and Root Exudates of Leafy Spurge (Euphorbia esulaL.)

Qin

Perry

Broeckling

et al. 2006

Plant Signaling & Behavior

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Invasive plants are a widespread problem but the mechanisms used by these plants to become invasive are often unknown. The production of phytotoxic natural products by invasive weeds is one mechanism by which these species may become successful competitors. Here, we conducted a bioactivity-driven fractionation of root extracts and exudates from the invasive plant leafy spurge (Euphorbia esula L.), and structurally characterized jatrophane diterpenes and ellagic acid derivatives. Ellagic acid derivatives and one of the jatrophane diterpenes, esulone A, have been previously reported from leafy spurge, but another of the jatrophane diterpenes, kasuinine B, has not. We show that these compounds are phytotoxic but affect plants in different ways, either inducing overall plant necrosis or reducing root branching and elongation.

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“…The last fraction yielded colorless needles (26 mg) from MeOH, which were identified to be 3,3Ј-di-O-methyl ellagic acid (3) by comparison of the 1 H-and 13 C-NMR spectral data with previously published values. 31) Euscaphinin (2) 1H, dd, Jϭ9.2, 10.0 Hz, Glc-3, 3Ј), 5.31, 5.29 (each 1H, dd, Jϭ6.9, 13.5 Hz, Glc-6a, 6aЈ), 5.14, 5.13 (each 1H, t, Jϭ10.0 Hz, Glc-4, 4Ј), 5.13 (1H, dd, Jϭ8.5, 9.2 Hz, Glc-2), 5.11 (1H, dd, Jϭ8.7, 9.2 Hz, Glc-2Ј), 4.45, 4.41 (each 1H, ddd, Jϭ1.4, 6.9, 9.9 Hz, Glc-4, 4Ј), 3.82, 3.77 (each 1H, dd, Jϭ1.4, 13.5 Hz, Glc-6b, 6bЈ). …”

Section: Methodsmentioning

confidence: 99%

Euscaphinin, a New Ellagitannin Dimer from Euscaphis japonica (THUNB.) KANITZ

Maeda

Matsuo

Tanaka

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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NotesRecent studies on plant polyphenols have revealed various biological activities for ellagitannins.1,2) Distribution of ellagitannins in plants is relatively limited compared with that of condensed tannins (proanthocyanidins).3) In this study, we proposed to find new plant sources of functional polyphenols and examined the leaves, bark and wood of 39 plant samples belonging to 32 genera of 29 families, distributed in the Nagasaki region of Japan, by thin-layer chromatography (TLC) and high performance liquid chromatography (HPLC). Plants belonging to the Elaeocarpaceae, 4) Myricaceae, 5) Anacardiaceae, 6) Juglandaceae, 7) Stachyuraceae,8) and Fagaceae [9][10][11] families were shown to contain high concentrations of polyphenols, substances that have already been studied chemically. Unexpectedly, our study disclosed accumulation of ellagitannins in the leaves of Euscaphis japonica (THUNB.) KANITZ (Staphyleaceae). E. japonica is a deciduous tree distributed in western Japan, and little is known about the phenolic constituents of this plant. [12][13][14][15][16] Presence of ellagitannins in Staphyleaceae has not yet been reported. This paper describes the isolation and structural determination of two ellagitannins, including a new dimeric ellagitannin. Results and DiscussionAn aqueous acetone extract of the fresh leaves of E. japonica was subjected to a combination of Diaion HP20SS, Sephadex LH-20, and Chromatorex ODS column chromatography to furnish two major phenolic compounds. One of the products was identified as 1(b)-O-galloyl pedunculagin (1) 17,18) by comparisons of 1 H-NMR spectral data, HPLC retention time and UV absorption with those of an authentic sample.Compound 2 was isolated as a white amorphous powder and produced a dark-blue coloration upon reaction with FeCl 3 and a brown coloration upon reaction with NaNO 2 -AcOH reagent, 19) suggesting this compound is an ellagitannin. The Rf value on silica gel TLC was much smaller than that of 1 and the matrix-assisted laser desorption/ionizationtime-of-flight (MALDI-TOF) MS showed a [MϩNa] ϩ peak at m/z 1893, indicating that 2 is a dimeric ellagitannin. This was supported by appearance of signals attributable to two sugar anomeric protons [d 6.16 (1H, d, Jϭ8.5 Hz, Glc-1), 6.06 (1H, d, Jϭ8.7 Hz, Glc-1Ј)] in the 1 H-NMR spectrum.The sugar was confirmed to be D-glucose by the HPLC analysis of the thiocarbamoyl-thiazolidine derivative of the acid hydrolysis products.20) The chemical shifts (d 3.7-6.2) and the large coupling constants of the sugar proton signals were similar to those of 1 and indicated that the anomeric positions were b-configurations and that all the hydroxyl groups of the pyranose ring were acylated. In the aromatic region of the spectrum, nine singlets [d 7.16, 6.66, 6.65, 6.51, 6.50, 6.47, 6.46, 6.33, 6.33] and two mutually coupled doublets [d 7.30, 6.84 (each d, Jϭ1.9 Hz)] were observed. The hetero-nuclear multiple-bond connectivity (HMBC) correlations (Fig. 2) of these aromatic protons indicated that all of the protons are attached t...

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Ellagic compounds from Diplopanax stachyanthus

Cited by 82 publications

References 17 publications

Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

Phytotoxic Allelochemicals From Roots and Root Exudates of Leafy Spurge (Euphorbia esulaL.)

Euscaphinin, a New Ellagitannin Dimer from Euscaphis japonica (THUNB.) KANITZ

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