4
58
J Nat Med (2012) 66:453–458
3
(1.1 mg, Fr-IV), 4 (11.7 mg, Fr-VI), 5 (1.4 mg, Fr-V and
of MeOH. These two solutions were mixed. The resulting
Fr-VI), 6 (2.9 mg, Fr-IX), 7 (1.0 mg, Fr-IV), 8 (3.7 mg, Fr-
VIII), 9 (2.4 mg, Fr-IV), 10 (2.4 mg, Fr-V), 11 (1.2 mg, Fr-
VIII), 12 (6.3 mg, Fr-IV), 13 (1.1 mg, Fr-VI), and 14
CH N gas was introduced into the solution of 6 (2.4 mg)
2
2
in MeOH for 24 h. After removing MeOH the reaction
product (6-Me, 2.7 mg) was obtained.
(
0.5 mg, Fr-VI).
-Hydroxy-1,8-dimethoxypyrene (1) Yellow amorphous
6-Me yellow oil. [a] -4.9° (c 0.26, CHC1 ), IR (KBr)
D
3
-
cm : 1715 (C=O), 1464, 1377, 1273, HREIMS (positive
1
2
-
resin. IR (KBr) cm : 3,300 (OH), 1591, 1313, 1251, 1091,
1
?
ion mode) m/z: 264.1726 [M] (calcd for C H O ,
16 24 3
?
1
000, HREIMS (positive ion mode) m/z: 278.0959 [M]
calcd for C H O , 278.0943), EIMS (positive ion mode)
264.1725), EIMS (positive ion mode) m/z (rel. int.): 264
?
1
13
(
[M] (42), 221 (93), 189 (100), H- and C-NMR
(Table 2).
1
8 14 3
?
1
13
m/z (rel. int.): 278 [M] (94), 263 (100), H- and C-
NMR (Table 1).
8
-Methoxy-1,2-methylenedioxypyrene
-
(2)
amorphous resin. IR (KBr) cm : 1597, 1510, 1461, 1444,
Yellow
1
References
1
2
336, 1253, 1136, HREIMS (positive ion mode) m/z:
?
76.0782 [M] (calcd for C H O , 276.0786), EIMS
1
8 12 3
?
positive ion mode) m/z (rel. int.): 276 [M] (100), 261
1. Verdcourt B (1971) Flora of tropical East Africa, annonaceae.
The East African Community, Nairobi, pp 17–18
(
(
1
13
99), H- and C-NMR (Table 1).
-Hydroxy-8-methoxy-1,2-methylenedioxypyrene (3)
2
. Achenbach A, Hohn M, Waibel R, Nkunya MH, Jorker SA,
Muhie S (1997) Oxygenated pyrenes, their potential biosynthetic
precursor and benzylated dihydroflavones from two African
Uvaria species. Phytochemistry 44:359–364
7
-
Yellow amorphous resin. IR (KBr) cm : 3,300 (OH),
1
1
602, 1508, 1460, 1444, 1336, 1251, 1193, HREIMS
3
4
. Weenen H, Nkunya MH, El-Fadl AA, Harkema S, Zwanenburg B
(
?
positive ion mode) m/z: 292.0741 [M] [calcd for
(
1990) Lucidine, a bis(benzoylpyranyl) sesquiterpene from
C H O , 292.0736), EIMS (positive ion mode) m/z (rel.
1
Uvaria lucida ssp. Lucida. J Org Chem 55:5107–5109
. Ichimaru M, Moriyasu M, Nishiyama Y, Kato A, Mathenge SG,
Juma FD, Nganga JN (1997) Studies on African medicinal plants.
Alkaloidal constituents of Uvaria accuminata and Uvaria lucida.
Nat Med 51:272–274
8 12 4
?
1
13
int.]: 292 [M] (100), 277 (93), 263 (59), H- and C-
NMR (Table 1).
2
-Hydroxy-1,8-pyrenedione (4) Purple amorphous resin.
1
-
IR (KBr) cm : 3,450 (OH), 1633 (C=O), 1587, 1500,
465, 1355, HREIMS (positive ion mode) m/z: 248.0487
5. Misra LN, Jakupovic J, Bohlmann F, Schmeda-Hirschmann G
1985) Isodaucane derivatives, norsesquiterpenes and clerodanes
(
1
?
from Chromolaena laevigata. Tetrahedron 41:5353–5356
. Hussein NS, Ahmed AA, Spaller M, Mabry TJ (1995) Terpenoids
from Conza linifolia. Asian J Chem 7:433–435
[
M] (calcd for C H O , 248.0473), EIMS (positive ion
16 8 3
6
?
1
mode) m/z (rel. int.): 245 [M] (100), 220 (37), H- and
1
3
C-NMR (Table 1).
-Methoxy-1,8-pyrenedione (5) Purple amorphous resin.
7. Hansson T, Wickberg B (1992) A short enantiospecific route to
isodaucane sesquiterpenes from limonene. On the absolute con-
figuration of (?)-aphanamol I and II. J Org Chem 57:5370–5376
2
-
1
IR (KBr) cm : 1645 (C=O), 1622 (C=O), 1595, 1348,
282, 1249, HREIMS (positive ion mode) m/z: 262.0623
1
8
. Lipaj T, Remco M, Polcin J (1980) Analysis of H-NMR spectra
of cinnamaldehyde type model substances in lignin. Collection
Czecoslov. Chem Commun 45:330–333
1
?
[
M] (calcd for C H O , 262.0630), EIMS (positive ion
17 10 3
?
1
13
mode) m/z (rel. int.): 262 [M] (100), H- and C-NMR
9
. Iijima T, Yaoita Y, Kikuchi M (2003) Five new sesquiterpenoids
and a new diterpenoid from Erigeron annuus (L.) Pers., Erigeron
philadelphicus L, and Erigeron summatrensis Rets. Chem Pharm
Bull 51:545–549
(
Table 1).
-)-10-oxo-isodauc-3-en-15-oic acid (6) Colorless oil.
(
-
1
[
a] -4.7° (c 0.09, CHC1 ), IR (KBr) cm : 1701 (C=O),
10. Zhang H-J, Tan GT, Santarsiero BD, Mesecar AD, Hung NV,
Cuong NM, Soejarto DD, Pezzuto JM, Fong HS (2003) New
sesquiterpenes from Listea verticillata. J Nat Med 66:609–615
D
3
1
675 (C=O), 1465, 1380, 1282, 1263, HREIMS (positive
?
ion mode) m/z: 250.1580 [M] (calcd for C H O ,
1
5 22 3
1
1. Ishiyama M, Miyazono Y, Sasamoto K, Ohkura Y, Ueno K
1997) A highly water-soluble disulfonated tetrazolium salt as
2
50.1569), EIMS (positive ion mode) m/z (rel. int.): 250
13
(
?
1
[
M] (42), 207 (93), 167 (100), H- and C-NMR
Table 2).
a chromogenic indicator for NADH as well as cell viability.
Talanta 44:1299–1305
(
1
2. Nakatani N, Ichimaru M, Moriyasu M, Kato A (2005) Induction
of apoptosis in human leukemia cell line HL-60 by C-benzylated
dihydrochalcones, uvaretin, isouvaretin, and diuvaretin. Biol
Pharm Bull 28:83–86
Methylation of 6 p-toluensulfonyl-N-methyl-N-nitros-
oamide (2 g) was dissolved in Et O (10 mL), and NaOH
2
(
0.5 g) was dissolved in 1 mL of water and added 10 mL
1
23