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, Des études métabolomiques comparant leur production en fonction de paramètres biotiques (infection par un champignon, infestation par des insectes ravageurs) et abiotiques (saisons, sécheresse, type de terrain) pourraient être menées afin d'apporter des éléments sur leur(s) rôle(s) biologique(s)

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, Chemical shifts (relative to TMS) are in ppm, and coupling constants are in Hz. Kromasil analytical and semi-preparative C 18 columns (250 × 4.6 mm and 250 × 10 mm i.d ; 5 µm Thermo Electron) and a Nucleodur PFP analytical column (250 × 4.6 mm i.d ; 5 µm Macherey-Nagel) were used for HPLC separations using a Waters autopurification system equipped with a binary pump (Waters 2525), a UV-vis diode array detector (190-600 nm, Waters 2996), and a PL-ELS 1000 ELSD Polymer Laboratory detector, Anton Paar MCP 300 polarimeter. UV spectra were recorded on a Varian Cary 100 UV-vis spectrophotometer. NMR spectra were recorded in MeOD or CDCl 3 on a Bruker 500 MHz instrument

. Merck-(france, Prepacked GraceResolv silica cartridges were used for flash chromatography using a Teledyne Isco Combiflash Rf 200i. HRESIMS data were acquired using an Acquity Waters UPLC coupled to a Waters LCT Premier XE mass spectrometer. The UPLC system was equipped with a Waters Acquity PDA dectector. Separation was achieved on a BEH C 18 column (1.7 µm, 2.1 mm × 50 mm) at a flow rate of 0.6 mL/min. Elution was conducted with a H 2 O-MeCN + 0.1% formic acid gradient as follows : 95 :5 to 0 :100 in 5.5 min. The ionization was carried out using an, The sulfuric molybdate was used as the staining reagent for TLC

, in Saint-Elie (French Guyana) and authenticated by Dr. Christian Moretti (IRD of French Guyana). A voucher 94 ANNEXE A. PROCÉDURES EXPÉRIMENTALES specimen (GUY-0361) has been deposited at IRD of French Guyana, Bark of Sandwithia guyanensis was, 2010.

, Extraction and isolation. The dried bark (704.2 g) of S. guyanensis were extracted with

. Etoac, 2 g) after concentration in vacuo at 40 ? C. This extract was dissolved in 250 mL of MeCN and subjected to a liquid/liquid partition with n-heptanes (3 × 250 mL) to afford 1.1 g of a MeCN-soluble fraction. This residue was subjected to silica gel column chromatography using a gradient of n-heptane-EtOAc-MeOH of increasing polarities, × 500 mL) to yield a crude extract

, MeCN-H 2 O + 0.1% formic acid, 52 :48, in 30 min, 4.7 mL/min) leading to five fraction (F3-1 to F3-6). F3-2 was further purified by analytical HPLC (Nucleodur PFP, MeCN-H 2 O (45 :55) + 0.1% formic acid at 1 mL/min), Purification of fraction F3 (55.2 mg) by semi-preparative HPLC (Kromasil C 18, vol.12, p.7

, MeCN-H 2 O (45 :55) + 0.1% formic acid at 1 mL/min), leading to compound jatrointelone C (3.2 mg) (Rt 12.94 min). F3-5 was further purified by analytical HPLC, min respectively). F3-3 was further purified by analytical HPLC (Nucleodur PFP, vol.70, p.30

, leading to compound 16 (0.5 mg) (Rt 6.39 min). F4 (36.1 mg) was purified by semi-preparative HPLC (Kromasil C 18 , MeCN-H 2 O + 0.1% formic acid, 52 :48, in 30 min, 4.7 mL/min) affording compound 1 (1.5 mg) (Rt 9, + 0.1% formic acid at 1 mL/min)

, Rt 11.5 min). F5 (54.2 mg) was purified by semi-preparative HPLC (Kromasil C 18

, 1% formic acid, 40 :60, in 30 min, 4.7 mL/min) affording compound 2 (23.7 mg) (Rt 11.5 min). F6 (36.1 mg) was purified by semi-preparative HPLC (Kromasil C 18

, 53, 12.76 and 17,13 min respectively). F10 (30.9 mg) was purified by semipreparative HPLC (Kromasil C 18 , MeCN-H 2 O + 0.1% formic acid, 35 :65, in 15 min, 4.7 mL/min) affording compound 4 (2.7 mg) (Rt 11.06 min). F11 (40.6 mg) was purified by semi-preparative HPLC (Kromasil C 18 , MeCN-H 2 O + 0.1% formic acid, 35 :65, in 30 min, 4.7 mL/min) affording compounds 7 (9.9 mg) and 15 (2.8 mg) (Rt 12.46 and 24.04 min respectively). F13 (96.4 mg) was purified by semi-preparative HPLC (Kromasil C 18 , MeCN-H 2 O + 0.1% formic acid, 35 :65, in 30 min, 4.7 mL/min) affording compounds 6 (21.0 mg). F14 (69.9 mg) was purified by semipreparative HPLC, 1% formic acid, vol.52, p.48

, mg) and 17 (1.5 mg) (Rt 12.18, 14.11 min and 7.49 min) and F14-1. F14-1 was purified by analytical HPLC (Kromasil C 18 , MeCN, MeOH (50 :50)-H 2 O + 0, mL/min) affording compounds 9

, F15 (45.1 mg) was purified by semi-preparative HPLC (Kromasil C 18 , MeCN-H 2 O + 0, p.1