1074 Natral Product Communications Vol.1(12)2006 Piacenteetal. O 0 H OH H OH HO H OH H OH H Figure 1:Compounds 1-13 isolated from the botk of M Column chromatography of a CHCl extract of the HSOC hark of M on silica gel.yielded compounds 1-13. crocarpa enal at 6 5.24 (IH.t J=3.5Hz） Compound 1 was obtained as an amorphous white mnd.which showed in theion IMH t m473. nparison with those of 33.22a-dihydi mode the quas at m/ 29-oic acid (3).known as maytenfolic acid [11] go the suggested that the difference between the two carbons.TheHNMR spectrum showed seven compounds should be confined to ring E[12]39.5 tertiary methyl singlets at 60.82.0.94.1.00.1.03. (C-17),49.9(C-18),44.3(C-19,46.2(C-20),40. 1.05,1.26,and 1.33.The presence of two secondary (C-21),78.8(C-22)34.1(C-29),181.1(C-30)in1上6 alcoholic functions was evident from the signals at 63.19 (IH,dd,J=3.5 and 11.5 Hz)and 63.62 a (IH.dd./=3.0 and 11.0 Hz).which correlated in the 1074 Natural Product Communications Vol. 1 (12) 2006 Piacente et al. R R''' R' R'' CH2OH HO R C C COO H H R 7 8 H OH R 9 10 11 12 H R' R'' H H H OH OH OH OH H CH2R'' RO R' HO C C CO H H HO C C CO H H HO C C CO H H HO R 1 2 3 4 5 6 β-OH O β-OH O β-OH O R' R'' R''' Me Me COOH COOH COOH COOH COOH COOH Me Me Me Me OH OH OH OH OH OH HO HO COOH O 13 Figure 1: Compounds 1-13 isolated from the bark of Maytenus macrocarpa. Column chromatography of a CHCl3 extract of the bark of M. macrocarpa on silica gel, yielded compounds 1-13. Compound 1 was obtained as an amorphous white solid, which showed in the ESI-MS in positive ion mode the quasi-molecular ion [M+H] + at m/z 473, corresponding to the molecular formula C30H48O4. The 13 C NMR spectrum showed signals for 30 carbons. The 1 H NMR spectrum showed seven tertiary methyl singlets at δ 0.82, 0.94, 1.00, 1.03, 1.05, 1.26, and 1.33. The presence of two secondary alcoholic functions was evident from the signals at δ 3.19 (1H, dd, J = 3.5 and 11.5 Hz) and δ 3.62 (1H, dd, J = 3.0 and 11.0 Hz), which correlated in the HSQC spectrum with the carbon resonances at δ 79.7 and 78.8, respectively. An additional feature of the 1 H NMR spectrum was a signal at δ 5.24 (1H, t, J = 3.5 Hz) typical of H-12 of a Δ-12 oleanene. Analysis of 1 H and 13 C NMR spectroscopic data and comparison with those of 3β,22α-dihydroxy-12-en- 29-oic acid (3), known as maytenfolic acid [11], suggested that the difference between the two compounds should be confined to ring E [12] [δ 39.5 (C-17), 49.9 (C-18), 44.3 (C-19), 46.2 (C-20), 40.7 (C-21), 78.8 (C-22) 34.1 (C-29), 181.1 (C-30) in 1; δ 39.9 (C-17), 48.3 (C-18), 42.3 (C-19), 45.2 (C-20), 38.9 (C-21), 76.9 (C-22), 180.6 (C-29), 21.6 (C-30) in 3]. Comparison of the ROESY spectra of 1 and 3