Trapanins A and B, oligomeric hydrolyzable tannins from Trapa japonica Flerov.

Hatano, Tsutomu; Okonogi, Akira; Yazaki, Kazufumi; Okuda, Takuo

doi:10.1248/cpb.38.2707

Cited by 26 publications

(12 citation statements)

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“…They posses a variety of structures, examples being gemins A, B and C (dimers) from Geum japonicum, an anti-inflammatory agent and a diuretic (Yoshida et al, 1982b,d, Fig 1985a), rugosins D, E and F (dimers) from Rosa rugosa, an antidiarrheic medicinal plant (Hatano et al, 1990c), cornusiins A (dimer), C (trimer), D, E (dimers) and F (trimer) from Cornus officinalis (Okuda et al, 1984d;Hatano et al, 1989a, and malabatrins B, C and D from Melastoma malabathricum . Several tetramers, e.g., trapanin B (22) from Trapa japonica, a tonic (Hatano et al, 1990a), nobotanin K from melastomataceous plants , and hirtellin Q 1 (along with a trimer, hirtellin T 1 and a dimer, hirtellin G) from Reaumuria hirtella (Ahmed et al, 1994b), as well as a pentamer from Monochaetum multiflorum (Jose et al, 2001) were also identified.…”

Section: Oligomeric Hydrolyzable Tanninsmentioning

confidence: 99%

“…9). Trapanin B (22) is a tetramer in which the monomeric units are linked via three m-DOG functionalities (Hatano et al, 1990a).…”

Section: Classification Of Hydrolyzable Tannin Oligomers Based On Thementioning

confidence: 99%

“…Anti-human immunodeficiency virus (HIV) activity was exhibited (Nakashima et al, 1992;Sakagami et al, 1999) by several hydrolyzable tannins, such as gemin D (monomer) (Yoshida et al, 1985b), nobotanin B (dimer) , camelliin B (dimer) (Yoshida et al, 1990b) and trapanin B (22) (tetramer) (Hatano et al, 1990a). In contrast to several biological activities exhibited by the high molecular weight tannins, gallic acid was the most active species in induction of DNA fragmentation and apoptosis, while the activities of the larger tannins were lower (Sakagami et al, 1995(Sakagami et al, , 1997(Sakagami et al, , 1999Inoue et al, 1994).…”

Section: Antiviral Activities Exhibited By Hydrolyzable Tannins and mentioning

confidence: 99%

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Systematics and health effects of chemically distinct tannins in medicinal plants

2005

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Section: Oligomeric Hydrolyzable Tanninsmentioning

confidence: 99%

“…9). Trapanin B (22) is a tetramer in which the monomeric units are linked via three m-DOG functionalities (Hatano et al, 1990a).…”

Section: Classification Of Hydrolyzable Tannin Oligomers Based On Thementioning

confidence: 99%

Section: Antiviral Activities Exhibited By Hydrolyzable Tannins and mentioning

confidence: 99%

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Systematics and health effects of chemically distinct tannins in medicinal plants

2005

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“…1). 1, 7 Oenothein B and A have both also been isolated as main components from other Oenothera species 8. Oenothein B has been detected in several other plant species, including Lythrum anceps (striped loosestrife), Epilobium parviflorum (small‐flowered hairy willowherb), Cuphea hyssopifolia (Mexican heather), Melaleuca leucadendron (melaleuca), Eugenia uniflora (surinam cherry), Eucalyptus alba (eucalyptus), Quercus rubra (red oak) and Woodfordia fruticosa (as listed in Coca et al 6…”

mentioning

confidence: 99%

“…1,7 Oenothein B and A have both also been isolated as main components from other Oenothera species. 8 Oenothein B has been detected in several other plant species, including Lythrum anceps (striped loosestrife), Epilobium parviflorum (small-flowered hairy willowherb), Cuphea hyssopifolia (Mexican heather), Melaleuca leucadendron (melaleuca), Eugenia uniflora (surinam cherry), Eucalyptus alba (eucalyptus), Quercus rubra (red oak) and Woodfordia fruticosa (as listed in Coca et al 6 ). We have previously isolated oenothein B from the inflorescences of Epilobium angustifolium (fireweed/willow herb) [2][3][4] and used it together with other purified ellagitannins to explore the in vitro anti-herbivore activity of ellagitannins, i.e.…”

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First evidence of hexameric and heptameric ellagitannins in plants detected by liquid chromatography/electrospray ionisation mass spectrometry

Karonen

Parker

Agrawal

et al. 2010

Rapid Commun. Mass Spectrom.

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Ellagitannins are bioactive plant polyphenols of which more than 500 individual compounds have been identified from plants. An ellagitannin-rich fraction was isolated by Sephadex LH-20 from Oenothera biennis (common evening primrose) leaves and roots and analysed by high-performance liquid chromatography/diode-array detection coupled to high-resolution mass spectrometry with an electrospray ionisation interface. The high-molecular mass ellagitannins were characterised by their UV spectra, molecular masses and mass spectral fragments. In addition to the previously reported dimers and trimers, an entire series of oligomeric ellagitannins from dimers to heptamers was characterised in both roots and leaves of O. biennis. This is the first report of natural ellagitannins larger than pentamers. Copyright # 2010 John Wiley & Sons, Ltd.Ellagitannins are the most numerous plant phenolics among the hydrolysable tannins. They are often connected with potent biological activities, including antiviral and immunomodulatory to defence against herbivores. [1][2][3][4][5][6] In fact, the developments in ellagitannin chemistry over the past decades are turning ellagitannins from the most underestimated class of plant tannins into one of the most promising ones. The past 45 years have witnessed the isolation and characterisation of over 500 pure ellagitannins, many of which have been used in traditional herbal medicines. More than half of these ellagitannins are oligomers, structures ranging from dimers up to pentamers. Until now, there has been no evidence of the presence of ellagitannins larger than pentamers in any plant species.Oenothera biennis (Onagraceae), common evening primrose, is a well-studied plant species with known medical applications. 5 Its foliage in particular has been reported to contain ellagitannins, including the primary molecules oenothein B and oenothein A (a macrocyclic dimer and a macrocyclic trimer, respectively; Fig. 1). 1,7 Oenothein B and A have both also been isolated as main components from other Oenothera species. 8 Oenothein B has been detected in several other plant species, including Lythrum anceps (striped loosestrife), Epilobium parviflorum (small-flowered hairy willowherb), Cuphea hyssopifolia (Mexican heather), Melaleuca leucadendron (melaleuca), Eugenia uniflora (surinam cherry), Eucalyptus alba (eucalyptus), Quercus rubra (red oak) and Woodfordia fruticosa (as listed in Coca et al. 6 ). We have previously isolated oenothein B from the inflorescences of Epilobium angustifolium (fireweed/willow herb) 2-4 and used it together with other purified ellagitannins to explore the in vitro anti-herbivore activity of ellagitannins, i.e. their ease of oxidation at the high pH values found in guts of lepidopteran insects. Here, we focus additional attention on O. biennis ellagitannins for two reasons: (1) our highperformance liquid chromatography/diode-array detection mass spectrometric (HPLC-DAD-MS) analyses revealed high complexity of ellagitannins in both roots and leaves of O. biennis, and (2) O....

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Ellagitannins - nature, occurrence and dietary burden

Clifford

Scalbert²

2000

J. Sci. Food Agric.

390

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The occurrence of ellagitannins in common foodstuffs is limited to a few fruit and nut species. Dietary intake of ellagitannins is largely explained by the consumption of strawberries, raspberries and blackberries. No reliable figures are available for the ellagitannin burden, but it will probably not exceed 5 mg day−1. Their bioavailability is not well defined. A fraction of the ellagitannins ingested is hydrolysed in the gut and the resulting ellagic acid absorbed and metabolised, but whether intact ellagitannins are absorbed is not clear. There are apparently conflicting claims for beneficial and toxic effects caused by ellagitannins, ellagic acid or ellagitannin‐containing extracts in various animal species including rodents and ruminants. It seems unlikely that normal consumption can cause toxic effects in man, but any attempt to increase the intake significantly in pursuit of the suggested benefits should be resisted until the metabolism and pharmacokinetics are better understood. © 2000 Society of Chemical Industry

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Trapanins A and B, oligomeric hydrolyzable tannins from Trapa japonica Flerov.

Cited by 26 publications

References 0 publications

Systematics and health effects of chemically distinct tannins in medicinal plants

Systematics and health effects of chemically distinct tannins in medicinal plants

First evidence of hexameric and heptameric ellagitannins in plants detected by liquid chromatography/electrospray ionisation mass spectrometry

Ellagitannins - nature, occurrence and dietary burden

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