Agrimoniin and potentillin, an ellagitannin dimer and monomer having an α-glucose core

Okuda, Takuo; Yoshida, Takashi; Kuwahara, Masaaki; Memon, Muhammad Usman; Shingu, Tetsuro

doi:10.1039/c39820000163

Cited by 46 publications

(28 citation statements)

References 1 publication

(1 reference statement)

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“…1D) of the ellagitannin group, named as HeT in this work. Two isomers, casuarictin and potentillin Haddock et al 1982;Okuda et al 1981Okuda et al , 1982Okuda et al , 1983, which respond to the same molecular formula and chemical structure as HeT have previously been reported in strawberry (Fait et al 2008;Hukkanen et al 2007;Oertel et al 2001).…”

Section: Resultsmentioning

confidence: 72%

Pathogen-Induced Accumulation of an Ellagitannin Elicits Plant Defense Response

Mamani¹,

Filippone²,

Grellet³

et al. 2012

MPMI

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In an incompatible interaction between Colletotrichum fragariae and strawberry plants, the accumulation of phenolic compounds in plant leaves was observed. A particularly abundant penta-esterified ellagitannin that accumulated in response to pathogen attack was identified as 1-0-galloyl-2,3;4,6-bis-hexahydroxydiphenoyl-β-d-glucopyranose (HeT) by mass spectroscopy and nuclear magnetic resonance. Foliar application of purified HeT prior to inoculation with a virulent pathogen was shown to increase resistance toward C. acutatum in strawberry plants and to Xanthomonas citri subsp. citri in lemon plants. The induced resistance in strawberry was associated with a rapid oxidative burst, callose deposition, a transient increase of salicylic acid in phloem, and induction of gene expression responsive to salicylic acid. Results obtained suggested that HeT could be a common plant defense response molecule capable of inducing pathogen resistance in different plant species.

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Section: Resultsmentioning

confidence: 72%

Pathogen-Induced Accumulation of an Ellagitannin Elicits Plant Defense Response

Mamani¹,

Filippone²,

Grellet³

et al. 2012

MPMI

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“…In particular, we found that Agrimonia pilosa (4) also had inhibitory activity on PR (35.0%, at 100 mg/mL). Although active constituents were not identified in this study, it is well known that Agrimonia pilosa contains agrimoniin, which is an oligomeric hydrolysable tannin (Okuda et al, 1982). Our previous investigation demonstrated that tannins inhibited RT and PR activity in a non-competitive manner (Kakiuchi et al, 1985;Kusumoto et al, 1995).…”

Section: Discussionmentioning

confidence: 71%

Inhibitory effects of Korean plants on HIV‐1 activities

Min

Kim

Tomiyama

et al. 2001

Phytotherapy Research

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In the search for novel anti-human immunodeficiency virus type 1 (anti-HIV-1) agents from natural sources, 49 MeOH extracts of Korean plants were screened for their inhibitory effects against RNA-dependent DNA polymerase (RT) and ribonuclease H (RNase H) activities of HIV-1 reverse transcriptase and HIV-1 protease, and anti-HIV-1 activity. Regarding the HIV-1 reverse transcriptase, Agrimonia pilosa (whole plant), Cornus kousa (stem and leaf), Limonium tetragonum (root) and Mallotus japonicus (stem) showed significant inhibitory activity on RT activity with 50% inhibitory activity (IC(50)) of 8.9, 6.3, 7.5 and 11.9 microg/mL, respectively, whereas Agrimonia pilosa was also active against RNase H activity (IC(50) = 98.4 microg/mL). Four plants, namely Agrimonia pilosa (whole plant), Atractylodes japonica (root), Clematis heracleifolia (whole plant) and Syneilesis palmata (whole plant), were appreciably active (<35%) against recombinant HIV-1 protease at a concentration of 100 microg/mL. Crinum asiaticum var. japonicum (root) showed significant anti-HIV-1 activity (ED(50) = 12.5 microg/mL) with a favourable SI value of 16.

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“…Baker, USA) and next on a Sephadex LH‐20 column (70 × 4 cm i.d., Pharmacia LKB, Sweden), using the following eluents: methanol:water (1:9, 2:8, 3:7, 4:6, 5:5, 7:3 and 10:0, v/v) and methanol:acetone (1:9, 2:8, and 5:5, v/v), respectively. The structures of isolated compounds were established by high‐resolution electrospray ionisation mass spectrometry (HRESI‐MS), 1 H‐, 13 C‐ and 2D‐NMR data and were confirmed by comparison with those reported in the literature (Okuda et al ., , ; Nishimura et al ., ; Saito et al ., ). ellagic acid ( EA ), gallic acid ( GA ), racemic catechin ( C ) and epicatechin ( EC ) were purchased from Extrasynthese (France).…”

Section: Methodsmentioning

confidence: 99%

“…Nevertheless, the use of octadecyl columns in the qualitative and quantitative analyses made it possible to identify polar phenolic compounds in a wider spectrum. Using UPLC-qTOF-MS/MS it was possible to identify altogether 42 constituents in tormentil products (Table 1), including well known compounds such as quinic acid stereoisomers (peaks 1 and 2), catechin (peak 10), procyanidin B3 (peak 8), procyanidin C2 (peak 9), ellagic acid (peak 38), pedunculagin anomers (peaks 3 and 7), potentillin (peak 35), agrimonic acid (peak 23), laevigatins (peaks 15, 20, 27 and 32) and agrimoniin (peak 41) (Okuda et al, 1982(Okuda et al, , 1984Yoshida et al, 1989aYoshida et al, , 1989bGeiger et al, 1994;Friedrich et al, 2000). Additionally there was a chance of identification of new compounds not described previously in this plant material such as the three isomeric monogalloylquinic acids (peaks 4-6) (Clifford et al, 2007) and 12 glycosides of ellagic or methylellagic acids (peaks 17, 18, 21, 24, 26, 28, 31, 36, 37, 39, 40 and 42) (Sun et al, 2014).…”

Section: Analysis Of Potentilla Tormentilla Rhizomesmentioning

confidence: 99%