Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica

Voutquenne, Laurence; Guinot, Pauline; Froissard, Clément; Thoison, Odile; Litaudon, Marc; Lavaud, Catherine

doi:10.1016/j.phytochem.2005.02.009

Cited by 46 publications

(22 citation statements)

References 9 publications

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“…2)]-a-L-arabinofuranosyl(1 ! 3)-b- D-glucuronopyranosyl-21,22-O-diangeloyl-3b,16a,21b, 22a,24b,28-hexahydroxyolean-12-ene (27) (Voutquenne et al, 2005;Zhang et al, 2006), 3-O-[b-D-galactopyranosyl-(1 ! 2)]-a-L-arabinofuranosyl(1 !…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.

Zhang

2007

Phytochemistry

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Section: Resultsmentioning

confidence: 99%

Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.

Zhang

2007

Phytochemistry

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“…chinensis Makino (Apiaceae) (Matsushita et al, 2004), and Harpullia austro-caledonica Baill. (Sapindaceae) (Voutquenne et al, 2005). Some saponins have been shown to possess anti-inflammatory properties (Matsuda et al, 1997;Sirtori, 2001;Wei et al, 2004), anti-HIV-1 protease activity (Yang et al, 1999), and cytotoxicity for tumor cells (D'Acquarica et al, 2002;Fu et al, 2006;Chan, 2007;Zhang and Li, 2007).…”

Section: Introductionmentioning

confidence: 99%

Phenolic compounds and rare polyhydroxylated triterpenoid saponins from Eryngium yuccifolium

Zhang

Ownby

et al. 2008

Phytochemistry

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“…Of these, I was purified on Bakerbond SPE silica gel disposable extraction columns (500 mg, 6 mL) using aethyl acetate saturated with water to yield barringtogenol C (4.5 mg). The structure was elucidated on the basis of NMR data (Table 2), obtained by dissolving the sample in CD 3 OD on a Bruker DRX-600 spectrometer at 300 K, and direct comparison with published values [14][15][16]. Assignments were based on 2D COSY, HOHAHA, HSQC, and HMBC experiments.…”

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Aescin determination in seeds and capsules of three pure and hybrid Aesculus species

Gleńsk

Włodarczyk

Bassarello³

et al. 2011

Chem Nat Compd

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The genus Aesculus L. consists of 13 species, distributed in the northern hemisphere, primarily in eastern Asia and eastern North America, with one species native to Europe, one to western North America, and one to northwestern Mexico [1]. No previous phytochemical studies were carried out on the investigated species. According to earlier reports on other species, Aesculus hippocastanum contains an aescin that is a natural mixture of triterpene saponins. The aglycons are derivatives of protoaescygenin, acylated by acetic acid at C-22 and by either angelic or tiglic acids at C-21. Two forms exists, D and E, which can be distinguished by melting point, specific rotation, hemolytic index, and solubility in water. A number of other products have been isolated from chestnut seeds, i.e., flavonoids such as quercetin, as well as antioxidants such as proanthocyanidin A 2 and the coumarins esculin and fraxin [2][3][4][5][6]. However, all of these products can be found in larger amounts in other sources; furthermore, it was concluded that the antiedematous, antiexudative, and vasoprotective activities of hippocastanus extracts (HCE) are exclusively due to aescin [4]. From the ethanolic extract of the roots of Aesculus assamica two novel triterpenoid saponins with insulin-like activity were isolated [7]. Also identification of novel saponins from edible seeds of Japanese horse chestnut (Aesculus turbinata) after treatment with wooden ashes and their nutraceutical activity were recently reported [8]. It is worth noting that sapogenols from Aesculus hippocastanum showed significant in vitro cytotoxicity in the 9-KB cell culture assay [9].Aescin occurrence and quantitative determination in seeds and capsules of three Aesculus species was performed by TLC densitometry. Surprisingly the highest aescin content was found in Aesculus u marylandica capsules, not seeds, whereas there was a lack of this substance in Aesculus parviflora capsules. In case of Aesculus u hemiacantha, the seeds were a richer source than capsules (Table 1). Moreover, from capsules of Aesculus u marylandica two sapogenins were isolated: barringtogenol C and protoaescygenin. The latter two compounds are ubiquitious metabolites of the genus Aesculus; however, their presence in capsules of Aesculus u marylandica was not previously described. It is also worth noting that Aesculus u marylandica, especially Aesculus parviflora, is resistant to Cameraria ohridella -horse chestnut leafminer [10,11]. However, our findings indicate that the high aescin content most probably does not determine their resistance against the moth.Plant Material. Both mature seeds and capsules of Aesculus u hemiacantha Topa (hybrid of A. hippocastanum and A. turbinata) and Aesculus u marylandica Booth ex Kirchn. (hybrid of A. flava and A. glabra) were collected at the Botanical Garden of Wroclaw University in 2005. The mature seeds and capsules of Aesculus parviflora Walt. were collected at Wojslawice Arboretum in 2005. All plant material was dried in a dark place in an oven at 40qC. A vou...

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Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica

Cited by 46 publications

References 9 publications

Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.

Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.

Phenolic compounds and rare polyhydroxylated triterpenoid saponins from Eryngium yuccifolium

Aescin determination in seeds and capsules of three pure and hybrid Aesculus species

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