Journal of Asian Natural Products Research
49
(
log 1): 279 (3.38) nm. IR (KBr) nmax:
424, 2921, 1619, 1500, 1468, 1325, 1073,
3.4 Acid hydrolysis
3
1
Each of compounds 1–4 (2 mg) was
dissolved in MeOH (1.0 ml) and 4 M
H SO (1.0 ml) solution and hydrolyzed
2
043, 835, 670, 567 cm . H and
1
1
13
C
NMR spectral (CD OD) data are listed in
3
2
4
Tables 1 and 2. FAB-MS (negative): m/z
2
under reflux for 2 h. The hydrolysate
was allowed to cool, diluted with 2 ml
H O, and extracted with 2 ml EtOAc.
2 2
55 [M2H] , 239 [M2OH] , 123
2
M2H2xylose] . HR-ESI-MS (nega-
[
2
2
tive): m/z 291.0637 [MþCl] (calcd for
The aqueous layer was neutralized with
aqueous Ba(OH)2 and concentrated in
vacuo to give a residue, in which xylose
C H O Cl, 291.0653).
12 16 6
(
from 1), glucose (from 2–4) and apiose
from 2 and 3) were identified by
3
.3.2 Orcinoside E (2)
(
2
D
0:8
Colorless powder. ½aꢀ
266.67
MeOH
max
comparing with authentic samples on
PC [BuOH–EtOAc–H O 4:1:5, upper
layer,
¼ 0.60 (xylose); BuOH–
EtOAc–H 4:1:5, upper layer,
¼ 0.45 (glucose); PhOH–H O, 4:1,
(
(
c ¼ 0.3, MeOH). UV (MeOH) l
2
log 1): 273 (3.21) nm. IR (KBr) nmax:
R
f
3
1
431, 2923, 1627, 1506, 1464, 1318, 1113,
13
O
2
2
1
1
071, 1033, 577, 563 cm . H and
C
R
R
f
f
2
NMR spectral (CD OD) data are listed in
3
¼ 0.55 (apiose) on PC, respectively].
Tables 1 and 2. FAB-MS (negative): m/z
2
17 [M2H] . HR-ESI-MS (negative):
Orcinol (from 1–3) was detected from
the EtOAc layer by TLC comparison
with an authentic sample (silica gel,
4
m/z 417.1404 [M2H]
2
(calcd for
C H O , 417.1396).
18 25 11
CHCl –MeOH 9:1).
3
Acknowledgements
3
.3.3 Orcinoside F (3)
2
D
0:9
This work was financially supported by the
project of Yunnan Science and Technology
Plan (No. 2008IF011), the major projects of
new drugs development of China (No.
2009ZX09102-126), the 973 project of the
Ministry of Sciences and Technology (No.
2009CB941300) and the Open Fund of the
State Key Laboratory in KIB (No.
Colorless powder. ½aꢀ
274.24
MeOH
max
(
(
c ¼ 0.3, MeOH). UV (MeOH) l
log 1): 279 (3.30) nm. IR (KBr) nmax:
3
1
422, 2923, 1615, 1462, 1426, 1321, 1172,
21 1
071, 994, 828, 677, 650, 571 cm . H
1
3
and C NMR spectral (CD OD) data are
3
listed in Tables 1 and 2. FAB-MS
0
807E31211). The authors are grateful to the
2
negative): m/z 417 [M2H] ; HR-ESI-
2
(
MS (negative): m/z 417.1407 [M2H]
members of the staff of analytical group of
State Key Laboratory of Phytochemistry and
Plant Resources, West China, Kunming Insti-
tute of Botany, Chinese Academy of Sciences,
for the measurements of all spectra.
(
calcd for C H O , 417.1396).
18 25 11
3
.3.4 Orcinoside G (4)
2
D
7:4
References
Colorless powder. ½aꢀ
235.16
MeOH
max
[1] G.W. Liu, Chinese Herbal Medicine
(
(
c ¼ 0.28, MeOH). UV (MeOH) l
(
HuaXia Publishing House, Beijing,
001), p. 99.
2] N.M. Triguna, S.S. Ram, M.T. Deonath,
log 1): 286 (3.31) nm. IR (KBr) nmax:
2
3
1
415, 2974, 1628, 1500, 1453, 1383, 1293,
21 1
074, 1044, 894, 803, 633, 582 cm . H
[
[
[
and C.S. Shekhar, Phytochemistry 29, 929
(
1
3
1990).
and C NMR spectral (CD OD) data are
3
3] M. Kubo, K. Namba, N. Nagamoto,
T. Nagao, J. Nakanishi, and H. Nishimura,
Planta Med. 47, 52 (1983).
4] J.P. Xu and R.S. Xu, Acta Pharm. Sin. 27,
353 (1992).
listed in Tables 1 and 2. FAB-MS
(
2
negative): m/z 329 [M2H] ; HR-ESI-
2
MS (negative): m/z 365.1010 [MþCl]
(
calcd for C H O Cl, 365.1003).
1
5 22 8