“…The aqueous layer was further partitioned with EtOAc and n-BuOH, successively. The combined EtOAc soluble fractions were then separated using Si-open column chromatography and HPLC repeatedly to yield thirty seven components: betulonic acid (1), 10 betulinic acid (2), 11 betulin (3), 12 lantabetulic acid (4), 13 3-oxoolean-18-en-28-oic acid (5), 14 3b-hydroxyolean-18-en-28-oic acid (6), 15 3-oxo-6b-hydroxyolean-18-en-28-oic acid (7), 16 semimoronic acid (8), 13 3-O-methyl semimoronic acid (9), 17 3-oxoolean-12-en-28oic acid (10), 18 oleanolic acid (11), 19 lantanolic acid (12), 20 3-oxotirucalla-7,24-dien-21-oic acid (13), 21 dipterocarpol (14), 22 3b-hydroxy-22,23,24,25,26,27-hexanordammaran-20-one (15), 23 b-sitosterol (16), 24 stigmast-4-en-3-one (17), 25 stigmast-4-ene-3,6-dione (18), 26 stigmastane-3,6-dione (19), 25 stigmast-7-en-3-ol (20), 27 pinoresinol (21), 28 4-oxopinoresinol (22), 29 4¢,5,7-trihydroxyflavanone (23), 30 trans-3,4¢,7-trihydroxyflavanone (24), 31 vanillin (25), 32 methyl ferulate (26), 33 3,5-dihydroxytoluene (27), 34 4-hydroxy-3,5dimethoxybenzaldehyde (28), 35 methyl gallate (29), 36 2,6dimethoxy [1,4]benzoquinone (30), 37 3,4,5-trimethoxyben-Hz) having W-shaped 1 H-1 H correlations with those of Ha-1 and H-5, respectively. The orientation of H 2 -25 was assigned to be b-form by a NOESY experiment.…”