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Quercetin 3-arabinopyranoside, a major flavonoid compound from Alchemilla xanthochlora

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  • .Fitoterapia 71 2000 463]464

    Phytochemical communication

    Quercetin 3-arabinopyranoside, a majorflavonoid compound from Alchemilla

    xanthochlora

    D. Fraissea, A. Heitzb, A. Carnata, A.-P. Carnata,J.-L. Lamaisona,U

    aLaboratoire de Pharmacognosie et Phytotherapie, Faculte de Pharmacie, Uniersite dAuergne, 28 place Henri Dunant, F-63000 Clermont-Ferrand, France

    bCBS, CNRS INSERM, Faculte de Pharmacie, Uniersite de Montpellier I, 15 aenue Charles Flahault, F-34060 Montpellier Cedex 1, France

    Received 13 December 1999; accepted 22 January 2000

    Abstract

    .Quercetin 3-O-a-L-arabinopyranoside 1 was isolated from the aerial parts of Alchemillax a n th o c h lo r a a n d c h a r a c t e r i z e d b y s p e c t r o s c o p i c a n a l y s i s .Q 2000 Elsevier Science B.V. All rights reserved.

    Keywords: Alchemilla xanthochlora; Flavonoids; Quercetin 3-O-arabinopyranoside

    .Plant. Alchemilla xanthochlora Rothm. Rosaceae flowering aerial parts were .collected in July 1998 in Puy-de-Dome France and authenticated by Prof. J.-L.

    Lamaison. A voucher specimen is deposited in the herbarium of the Faculty of .Pharmacy of Clermont-Ferrand France .

    Uses in traditional medicine. Used in European traditional medicine as an astrin-w xgent against bleeding and diarrhoea 1 .

    U Corresponding author. .E-mail address: [email protected] J.-L. Lamaison .

    0367-326Xr00r$ - see front matter Q 2000 Elsevier Science B.V. All rights reserved. .PII: S 0 3 6 7 - 3 2 6 X 0 0 0 0 1 4 5 - 3

  • ( )D. Fraisse et al. r Fitoterapia 71 2000 463]464464

    Previously isolated constituents. Other flavonoids, including quercetin 3-O-w xglucuronide 2]4 .

    . .New-isolated constituents. Quercetin 3-O-a-L-arabinopyranoside guaijaverin 1w x .5,6 yield: 0.2% on dry wt. Yellowish powder; m.p. 2408C; UV max MeOH : 254,

    1 . .353 nm; H-NMR 300 MHz, DMSO-d6 : d 3.22 C-H, dd, J 2.0, 11.2 Hz, H-50 , d . .3.52 1H, dd, J 7.1, 3.2 Hz, H-30 , d 3.60 C-H, dd, J 5.2, 11.2 Hz, H-50 , d 3.66

    . . 1H, ddd, J 3.2, 5.2, 2.0 Hz, H-40 , d 3.76 1H, dd, J 5.1, 7.1 Hz, H-20 , d 5.27 1H,. . .d, J 5.1 Hz, H-10 , 6.18 1H, d, J 1.7 Hz, H-6 , 6.38 1H, d, J 1.7 Hz, H-8 , 6.83

    . . 1H, d, J 8.5 Hz, H-59 , 7.50 1H, d, J 2.2 Hz, H-29 , 7.65 1H, dd, J 8.5, 2.2 Hz,. 13 . . . . .H-69 ; C-NMR DMSO-d : 156.3 C-2 , 133.6 C-3 , 177.4 C-4 , 161.1 C-5 , 98.76

    . . . . . . .C-6 , 164.6 C-7 , 93.5 C-8 , 156.1 C-9 , 103.7 C-10 , 120.8 C-19 , 115.6 C-29 , . . . . . .144.9 C-39 , 148.6 C-49 , 115.3 C-59 , 122.0 C-69 , 101.4 C-10 , 70.7 C-20 , 71.6

    . . . w xC-30 , 66.0 C-40 , 64.2 C-50 5,6 .

    References

    w x1 Wichtl M, Anton R. Plantes therapeutiques. Tec & Doc Paris 1999:10.w x2 Lamaison JL, Carnat A, Petitjean-Freytet C, Carnat AP. Ann Pharm Fr 1991;49:186.w x3 DAgostino M, Dini I, Ramundo E, Senatore F. Phytother Res 1998;12:S162.w x4 Felser C, Schimmer O. Planta Med 1999;65:668.w x5 Markham KR, Ternai B, Stanley R, Geiger H, Mabry TJ. Tetrahedron 1978;34:1389.w x6 Pachaly P, Klein M. Planta Med 1987;53:442.