Metabolism of stilbene phytoalexins by botrytis cinerea: 1. Characterization of a resveratrol dehydrodimer

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 537-540

  Breuil, Anne Céline ^a   Adrian, Marielle ^a   Pirio, Nadine ^a   Meunier, Philippe ^a   Bessis, Roger ^a   Jeandet, Philippe ^b  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHYTOALEXIN; RESVERATROL; STILBENE DERIVATIVE;

ARTICLE; DIMERIZATION; METABOLISM; METABOLITE; MOULD; NONHUMAN; REACTION ANALYSIS;

EID: 0032510087     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10622-0     Document Type: Article

References (17)

1. 1. Langcake, P.; Pryce, R.J., Physiol. Plant Pathol., 1976, 9, 77-86.
2. 2. Adrian, M.; Jeandet P.; Veneau, J.; Weston, L.A.; Bessis, R., J. Chem. Ecol., 1997, 23, 1689-1702.
3. 3. Stoessl, A., Biosynthesis of phytoalexins, in : Phytoalexins, Bailey, J.A.; Mansfield, J.W., Eds.; Blackie : Glasgow and London, 1982, pp. 133-180.
4. 4. Langcake, P.; Pryce, R.J., Experientia, 1977a, 33, 151-152.
5. 5. Pezet, R.; Pont, V.; Hoang-Van, K., Physiol. Mol. Plant Pathol., 1991, 39, 441-450.
6. 6. Sbaghi, M.; Jeandet, P.; Bessis, R.; Leroux, P., Plant Pathol., 1996, 45, 139-144.
7. 7. Jeandet, P.; Breuil, A.C.; Adrian, M.; Weston, L.A.; Debord, S.; Meunier, P.; Maume, G.; Bessis, R., Anal. Chem., 1997, in press.
8. 8. Hillis, W.E.; Ishikura, N., J. Chromatogr., 1968, 32, 323-336.
9. 9. Langcake, P.; Pryce, R.J., J.C.S. Chem. Comm., 1977b, 208-210.
10. 10. Hölscher, D.; Schneider, R., Phytochemistry, 1996, 43, 471-473.
11. 11. Mayer, A. M., Phytochemistry, 1987, 26, 11-20.
12. 12. Mayer, A.M.; Harel, E., Phytochemistry, 1979, 18, 193-215.
13. 13. Pedreno, M.A.; Morales, M.; Calderon, A.A.; Zapata, J.M.; Ros Barcelo, A., A trans-Resveratrol oxidizing basic peroxydase isoenzyme from Vitis vinifera, in : Plant peroxidases : Biochemistry and Physiology, Obinger, C.; Burger, U.; Ebermann, R.; Penel, C.; Greppin, H., Eds; University of Genova, 1996, pp. 338-344.
14. 6. Resveratrol and its major metabolite (3) were extracted with ethyl acetate (v : v). Organic phases were concentrated under vacuum, at 35°C. The dried extract was then dissolved in MeOH before pre-purification by TLC.
15. 1. The first compound (Rf = 0.66) was identified as the non-degraded resveratrol, the second compound (Rf = 0.53) corresponding to the resveratrol metabolite (3). Bands corresponding to compound (3) were collected and eluted in ethyl acetate. The cis and the trans isomers of (3) were then separated by semi-preparative HPLC using an Ultrabase C18 reversed-phase column (5μm, 250×4 mm) with a mobile phase of 40% acetonitrile / 60% water at a flow rate of 4 mL / min. Detection was at 308 nm.
16. 6O) δ 57.15 (C-2C), 93.57 (C-1C), 106.86 (C-2B, C-6B), 101.79 (C-4B), 102.12 (C-4E), 105.15 (C-2E, C-6E), 109.86 (C-5D), 115.62 (C-3A, C-5A), 123.44 (C-2D), 126.7 (C-α), 128.09 (C-2A, C-6A), 128.60 (C-β), 128.14 (C-6D), 131.26, 131.67 and 132.05 (C-1D, C-1A, C-3D), 140.28 (C-1E), 144.73 (C-1B), 157.88 (C-4A), 159.00 (C-3E, C-5E), 159.22 (C-3B, C-5B), 160.13 (C-4D).
17. 6O) : δ 4.43 (d, J = 8.4 Hz, H-2C), 5.38 (d, J = 8.6 Hz, H-1C), 6.14 (d, J = 2.2 Hz, H-2B, H-6B), 6.23 (t, J = 2.1 Hz, H-4E), 6.25 (t, J = 2.2 Hz, H-4B), 6.33 (d, J = 2.0 Hz, H-2E, H-6E), 6.36 (d, J = 12.4 Hz, Hα), 6.50 (d, J = 12.1 Hz, Hβ), 6.77 (d, J= 8.3 Hz, H-5D), 6.87 (d, J = 8.8 Hz, H-3A, H-5A), 6.96 (brs, H-2D), 7.22 (d, J = 8.8 Hz, H-6D), 7.23 (d, J = 8.8 Hz, H-2A, H-5A).