The trunk bark of Tabebuia caraiba Bignoniaceae was found to contain four novel iridoids, 6-O-E-p-coumaroyljioglutin D (2), 6-O-E-p-coumaroyl-3-demethyl-3-O-ethyljioglutin D (3), 6-O-E-p-coumaroyl-1-demethyl-1-O-ethyljioglutin D (4), 7-O-E-p-coumaroyljiofuranaldehyde (5), three known iridoids, including one iridoid glucoside, jioglutin D (1), rehmaglutin D (6), 6-O-E-p-coumaroylcatalpol (7). From the flowers were obtained six triterpenes, betulinic acid (8), olean-12-en-3-one (9), β-amyrin (10), oleanolic acid (11), ursolic acid (12), 3-O-E-p-coumaroylursolic acid (13), 2α-hydroxyursolic acid (14), 6β,19α-dihydroxyursolic acid (15), and one phenylethanoid, tyrosol (16), in addition to β-sitosterol, β-sitosterol-3-O-β-D-glucopyranoside and β-sitosterol-3-O-β-D-(6´-O-acyl)-glucopyranoside and E-p-coumaric acid. The structures of the isolated compounds were established on the basis of 1D and 2D NMR spectroscopic techniques. The chemical profile of the trunk bark of the plant was determined by HPLC/DAD/HRESIMS and did not present a good correlation with the phytochemical study. It did not detect most of the isolated substances and allowed to propose the presence of some non-isolated compounds. iridoids 6OEpcoumaroyljioglutin OEpcoumaroyljioglutin 6 O E p coumaroyljioglutin 2, 2 , (2) 6OEpcoumaroyl3demethyl3Oethyljioglutin OEpcoumaroyldemethylOethyljioglutin coumaroyl 3 demethyl ethyljioglutin 3, (3) 6OEpcoumaroyl1demethyl1Oethyljioglutin 1 4, 4 (4) 7OEpcoumaroyljiofuranaldehyde OEpcoumaroyljiofuranaldehyde 7 coumaroyljiofuranaldehyde 5, 5 (5) glucoside 1, (1) 6, (6) 6OEpcoumaroylcatalpol OEpcoumaroylcatalpol coumaroylcatalpol 7. . (7) triterpenes 8, 8 (8) olean12en3one oleanenone olean 12 en 9, 9 (9) βamyrin β amyrin 10, 10 (10) 11, 11 (11) 12, (12) 3OEpcoumaroylursolic OEpcoumaroylursolic coumaroylursolic 13, 13 (13) 2αhydroxyursolic αhydroxyursolic 2α hydroxyursolic α 14, 14 (14) 6β,19αdihydroxyursolic 6β19αdihydroxyursolic βαdihydroxyursolic 6β,19α dihydroxyursolic 6β 19α 15, 15 (15) phenylethanoid 16, 16 (16) βsitosterol, βsitosterol sitosterol, sitosterol β-sitosterol βsitosterol3OβDglucopyranoside βsitosterolOβDglucopyranoside glucopyranoside βsitosterol3OβD6´Oacylglucopyranoside βsitosterol3OβD6Oacylglucopyranoside βsitosterolOβDOacylglucopyranoside 6´ acyl Epcoumaric coumaric techniques HPLCDADHRESIMS HPLC DAD HRESIMS study nonisolated non (2 OEpcoumaroyl Oethyljioglutin (3 (4 (5 (1 (6 (7 (8 (9 (10 (11 (12 (13 (14 19αdihydroxyursolic αdihydroxyursolic 6β19α βα (15 (16 OβDglucopyranoside βsitosterol3OβD6 Oacylglucopyranoside OβD ( βsitosterolOβD βsitosterol3OβD