X.-F. Wu et al. / Tetrahedron 67 (2011) 8155e8159
8159
then purified by Sephadex LH-20 (MeOHeH2O, 1:1), finally sepa-
rated by ODS eluting with MeOHeH2O (45:55 to 80:20) to afford
compounds 3 (25.1 mg) and 4 (8.3 mg).
microsomal lipid per-oxidation induced by ferrous-cysteine. MDA
was detected by using the thiobarbituric acid (TBA) method. Mi-
crosomal protein (1 mg/mL), different concentration of compounds,
cysteine (0.2 mM) in 0.1 M PBS were incubated for 15 min at 37 ꢃC.
Ferrous (0.5 mM) was added and the mixture was incubated for
another 15 min at the same temperature. Equal volume of 20% TCA
was added to terminate the reaction. The above solvent was
centrifuged for 10 min at 3000 rpm. The supernatants reacted with
0.67% TBA for 10 min at 100 ꢃC. After being cooled to room tem-
perature, the MDA was determined by the absorbance at 532 nm,
and then the inhibitory rates were calculated.
4.4.1. Lysidicin I (1). Pale yellow powder; ½a D20
ꢂ14.0 (c 0.07,
ꢁ
MeOH); UV (MeOH) lmax (log ) 233 (3.19), 292 (2.75) nm; CD
3
(MeOH):
l
(
D
3
) 225 (þ0.5), 254 (þ19.5), 271 (0), 285 (ꢂ8.4), 314
(ꢂ0.3); IR (KBr): 3379,1624,1600,1510,1431,1369,1304,1209 cmꢂ1
;
for 1H and 13C NMR spectroscopic data see Table 1; HRESIMS: m/z
539.1902 [MþNa]þ (calcd for C27H32O10Na, 539.1893).
4.4.2. Lysidicin J (2). Pale yellow powder; ½a D20
ꢂ93.0 (c 0.05,
ꢁ
MeOH); UV (MeOH) lmax (log ) 230 (3.06), 290 (2.72) nm; CD
3
Acknowledgements
(MeOH):
l
(
D
3
385 (0); IR (KBr): 3319, 2952, 1639, 1620, 1523, 1464, 1117,
1087 cmꢂ1; for 1H and 13C NMR spectroscopic data see Table 1;
HRESIMS: m/z 377.1219 [MþNa]þ (calcd for C17H22O8Na, 377.1212).
This work was supported financially by the National Science
Fund for Distinguished Young Scholars (No. 30625040), the
National Natural Science Foundation of China (No. 20672145),
and the National Science and Technology Project of China (No.
2009ZX09311-004).
4.4.3. Lysidiside V (3). Pale yellow powder; ½a D20
þ67.1 (c 0.1,
ꢁ
MeOH); UV (MeOH) lmax (log ) 227 (4.23), 286 (3.75) nm; CD
3
(MeOH):
l
(
D
3
IR (KBr):3371, 2958, 2874, 1607, 1516, 1428, 1145, 1078 cmꢂ1; for 1H
and 13C NMR spectroscopic data see Table 1; HRESIMS: m/z
667.2015 [MþNa]þ (calcd for C32H36O14Na, 667.2003).
Supplementary data
Supplementary data associated with this article can be found, in
4.4.4. Lysidiside W (4). Pale yellow powder; ½a D20
þ52.0 (c 0.1,
ꢁ
MeOH); UV (MeOH) lmax (log ) 229 (4.19), 287 (3.71) nm; CD
3
(MeOH):
l
(
D
3
) 200 (0), 209 (ꢂ6.9), 237 (0), 240 (þ1.2), 300 (ꢂ3.8),
References and notes
360 (ꢂ0.1); IR (KBr): 3313, 2957, 1605, 1520, 1434, 1149, 1072 cmꢂ1
;
for 1H and 13C NMR spectroscopic data see Table 1; HRESIMS: m/z
661.2116 [MþH]þ (calcd for C32H37O15, 661.2127).
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A solution of compound 3 (18 mg) in water (2 mL) was incubated
with helicase (36 mg) for 12 h at 37 ꢃC, then extracted with EtOAc.
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(1H, m, H-200), 0.93 (3H, d, J¼6.6 Hz, H-1100), 0.90 (3H, d, J¼6.6 Hz, H-
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164.3 (C-800), 162.3 (C-600), 158.5 (C-9),157.7 (C-5/7/40), 132.0 (C-10),
129.0 (C-20/60); 115.8 (C-30/50); 107.9 (C-900); 105.6 (C-500), 102.4 (C-
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4.6. Bioassays28
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The antioxidant activities of 1e4 were determined by the con-
tent of MDA (malondialdehyde), which was produced during