The dried aerial part (1.5 kg) of T. laurifolia was
extracted with hot MeOH (40 l, with reflux for 24 h,
Table 1
13C NMR Spectral data of compounds 3–5 (CD3OD, 100 MHz)
C 3 4 5
1 96.2 95.5 96.5
3 140.3 140.7 143.1
4 108.2 107.6 108.2
5 34.4 34.6 73.6
6 33.1 33.0 79.2
7 29.8 29.0 59.4
8 46.8 45.8 56.3
9 48.4 46.4 50.7
10 185.7 179.5
10 99.8 99.7 100.0
20 74.8 74.7 74.1
30 78.2 78.1 87.4
40 71.6 71.4 70.1
50 77.9a 77.9 77.9a
60 62.8 62.6 62.7
100 105.3
200 75.6
300 78.1a
400 71.6
500 78.2a
600 62.7
a May be interchanged.
770 T. Kanchanapoom et al. / Phytochemistry 60 (2002) 769–771
70 C). After removal of the solvent in vacuo, the resulting
residue (189 g) was suspended in H2O (1 l) and defatted
with Et2O (3 l). The aqueous layer was applied to a column
of highly porous copolymer of styrene and divinylbenzene
and eluted with H2O, 50% MeOH, MeOH and Me2CO,
successively. The fraction eluted with 50%MeOH(10.0 g)
was applied to a column of silica gel (solvent systems I, II
and III, respectively) affording six fractions. Fraction 1
(4.0 g) was separated on a RP-18 column (solvent system
IV) to give six fractions. Fraction 1-2 (520 mg) was
purified by prep. HPLC-ODS (solvent system V) to afford
1 (41 mg), 2 (74 mg) and 4 (10 mg). Fractions 1-3 (222 mg)
and 1-5 (434 mg) were purified by using RP-18 column
(solvent system VI) and prep.HPLC-ODS (solvent system
VII) to give 6 (7 mg), 7 (9 mg) and 8 (47 mg). Fraction 2
(2.3 g) was applied to a RP-18 column (solvent system
IV) to afford five fractions. Fraction 2-1 (877 mg) was
purified by using RP-18 column (solvent system VI) and
prep. HPLC-ODS (solvent system VI) to provide compounds
3 (55 mg) and 5 (17 mg). Finally, fraction 2-2 (145
mg) was purified by prep. HPLC-ODS to give 9 (20 mg).