Med Chem Res
1636 (C=C), 1595, 1512, 1466 (ar. C=C); 1H NMR
(CDCl3, 200 MHz) d ppm: 7.0 (1H, Ar–H), 6.69–6.64 (m,
2H, Ar–H), 5.9–5.8 (1H, Allylic), 5.2–4.8 (m, 6H, sp3,
Allylic), 4.3–4.0 (m, 2H, sp3), 3.8–3.7 (m, 4H, sp3), 3.3
(2H, sp3), 2.05–2.01 (12H, sp3); 13C NMR (CDCl3,
50 MHz) d ppm: 170.4–169.1 (4C, C=O), 150.2 (1C, ar.),
144.1 (1C, ar.), 136.9 (1C, ar.), 136.5 (1C, allylic), 120.3
(1C, ar.), 120.0 (1C, ar.), 115.7 (1C, allylic), 112.7 (1C,
ar.), 100.7 (1C, sugar), 72.3 (1C, sugar), 71.6 (1C, sugar),
70.9 (1C, sugar), 68.1 (1C, sugar), 61.6 (1C, sugar), 55.6
(1C, sp3), 39.6 (1C, sp3), 20.3–20.3 (4C, sp3); Mol. for-
mula: C24H30O11; Mol. Weight: 494.4.
2975, 2917 (sp3 C–H), 1638 (C=C), 1595, 1512, 1465 (ar.
1
C=C); H NMR (DMSO, 200 MHz) d ppm: 7.0 (1H, Ar–
H), 6.8 (1H, Ar–H), 6.6 (1H, Ar–H), 6.0–5.8 (1H, Allylic),
5.1–4.8 (m, 6H, sp3, Allylic, OH), 4.5 (1H, OH), 3.7–3.1
(m, 10H, sp3, Allylic, OH); 13C NMR (DMSO, 50 MHz) d
ppm: 148.8 (1C, ar.), 144.8 (1C, ar.), 137.9 (1C, allylic),
133.4 (1C, ar.), 120.2 (1C, ar.), 115.5 (1C, allylic), 115.4
(1C, ar.), 112.8 (1C, ar.), 100.1 (1C, sugar), 76.9 (1C,
sugar), 76.8 (1C, sugar), 73.2 (1C, sugar), 69.6 (1C, sugar),
60.5 (1C, sugar), 55.5 (1C, sp3), 38.8 (1C, sp3); Mol. for-
mula: C16H22O7; Mol. Weight: 326.24.
4-allyl-2-methoxyphenylb-D-galactopyranoside(8) White
crystals, yield: 55 %; m.p. 163–165 °C; [a]D –34.6° (c 0.5
MeOH); IR; tmax in cm-1: 3350 (OH), 3001 (ar. C–H), 2975,
2938, 2903 (sp3 C–H), 1638 (C=C), 1594, 1514, 1464 (ar.
C=C); 1H NMR (DMSO, 200 MHz) d ppm: 7.0 (1H, Ar–H),
6.7 (1H, Ar–H), 6.6 (1H, Ar–H), 6.0–5.8 (1H, Allylic),
5.1–5.0 (m, 3H, sp3, OH), 4.87–4.80 (m, 2H, sp3, Allylic), 4.6
(1H, OH), 4.5 (1H, Allylic), 3.7–3.2 (m, 11H, sp3, Allylic);
13C NMR (DMSO, 50 MHz) d ppm: 148.9 (1C, ar.), 144.9
(1C, ar.), 137.9 (1C, allylic), 133.3 (1C, ar.), 120.2 (1C, ar.),
115.5 (1C, allylic), 115.4 (1C, ar.), 112.8 (1C, ar.), 100.7 (1C,
sugar), 75.4 (1C, sugar), 73.5 (1C, sugar), 70.2 (1C, sugar),
68.1 (1C, sugar), 60.3 (1C, sugar), 55.6 (1C, sp3), 39.1 (1C,
sp3); Mol. formula: C16H22O7; Mol. Weight: 326.24.
4-allyl-2-methoxyphenyl-(2,3,4,6-tetra-O-acetyl-b-D-galac-
topyranoside) (5)
White crystals, yield: 56 %; m.p.
125–127 °C; [a]D –11.5° (c 0.5 CH2Cl2); IR; tmax in cm-1
:
2972, 2881 (sp3 C–H), 1736 (C=O), 1642 (C=C), 1604,
1588, 1508, 1467 (ar. C=C); 1H NMR (CDCl3, 200 MHz) d
ppm: 7.0 (1H, Ar–H), 6.7–6.6 (m, 2H, Ar–H), 6.0–5.8 (1H,
Allylic), 5.5–5.4 (m, 2H, Allylic, sp3), 5.1–5.0 (m, 3H, sp3,
Allylic), 4.86 (1H, anomeric, J = 8 Hz), 4.2–4.1 (m, 2H,
sp3), 3.98–3.92 (1H, sp3), 3.8 (3H, sp3), 3.34 (2H, sp3),
2.1–2.0 (12H, sp3); 13C NMR (DMSO, 50 MHz) d ppm:
170.1–169.3 (4C, C=O), 150.2 (1C, ar.), 144.3 (1C, ar.),
136.9 (1C, ar.), 136.4 (1C, allylic), 120.3 (1C, ar.), 119.8
(1C, ar.), 115.7 (1C, allylic), 112.7 (1C, ar.), 101.3 (1C,
sugar), 70.56 (1C, sugar), 70.50 (1C, sugar), 68.4 (1C,
sugar), 66.6 (1C, sugar), 60.9 (1C, sugar), 55.7 (1C, sp3),
39.6 (1C, sp3), 20.5–20.3 (4C, sp3); Mol. formula:
C24H30O11; Mol. Weight: 494.4.
4-allyl-2-methoxyphenyl b-D-lactoside (9) Brown crys-
tals, yield: 50 %; m.p. 190–192 °C; [a]D -27.5° (c 0.5
MeOH); IR; tmax in cm-1: 3358 (OH), 2971, 2918 (sp3 C–
1
H), 1638 (C=C), 1593, 1512, 1460 (ar. C=C); H NMR
4-allyl-2-methoxyphenyl-(2,3,6,20,30,40,60-hepta-O-acetyl-
b-D-lactoside) (6) Pale yellow crystals, yield: 51 %; m.p.
51.2–53,7 °C; [a]D –19.7° (c 0.5 CH2Cl2); IR; tmax in
cm-1: 2972, 2901 (sp3 C–H), 1741 (C=O), 1638 (C=C),
1594, 1509 (ar. C=C); 1H NMR (CDCl3, 300 MHz) d ppm:
6.9 (1H, Ar–H), 6.7–6.6 (m, 2H, Ar–H), 5.9–5.8 (1H,
Allylic), 5.3–4.8 (m, 8H, sp3, allylic), 4.1–4.0 (m, 4H, sp3),
3.9–3.8 (m, 3H, sp3), 3.7–3.6 (m, 1H, sp3), 3.7 (s, 3H, sp3),
3.3 (2H, sp3, J = 6 Hz), 2.1–1.9 (21H, sp3); 13C NMR
(CDCl3, 75 MHz) d ppm: 170.6–169.3 (7C, C=O), 150.7
(1C, ar.), 144.6 (1C, ar.), 137.4 (1C, ar.), 136.9 (1C,
allylic), 120.8 (1C, ar.), 120.2 (1C, ar.), 116.2 (1C, allylic),
113.3 (1C, ar.), 101.2 (1C, sugar), 101.0 (1C, sugar), 76.5
(1C, sugar), 73.0 (1C, sugar), 72.9 (1C, sugar), 71.6 (1C,
sugar), 71.2 (1C, sugar), 70.9 (1C, sugar), 69.3 (1C, sugar),
62.2 (1C, sugar), 61.1 (1C, sugar), 60.6 (1C, sugar), 56.1
(1C, sp3), 39.9 (1C, sp3), 20.8 (7C, sp3); Mol. formula:
C36H46O19; Mol. Weight: 782.4.
(DMSO, 400 MHz) d ppm: 6.9 (1H, Ar–H), 6.7 (1H, Ar–
H), 6.5 (1H, Ar–H), 5.89–5.79 (1H, allylic), 5.23 (1H, sp3),
4.99–4.92 (4H, allylic, sp3), 4.83 (2H, OH), 4.66 (1H, OH),
4.56–4.40 (2H, sp3), 4.1 (1H, OH), 3.64 (3H, sp3),
3.53–3.19 (m, 14H, sp3, OH, allylic). 13C NMR (DMSO,
50 MHz) d ppm: 148.9 (1C, ar.), 144.7 (1C, ar.), 137.8 (1C,
ar.), 133.6 (1C, allylic), 120.2 (1C, ar.), 115.57 (1C,
allylic), 115.55 (1C, ar.), 112.9 (1C, ar.), 103.8 (1C, sugar),
99.8 (1C, sugar), 80.2 (1C, sugar), 75.5 (1C, sugar), 75.0
(1C, sugar), 74.8 (1C, sugar), 73.2 (1C, sugar), 73.0 (1C,
sugar), 70.5 (1C, sugar), 68.1 (1C, sugar), 60.4 (1C, sugar),
60.1 (1C, sugar), 55.6 (1C, sp3), 39.0 (1C, sp3); Mol. for-
mula: C22H32O12; Mol. Weight: 488.32.
In vitro bioassays
Antifungal activity evaluation
Eugenol (EUG) and its derivatives 4, 5, 6, 7, 8 and 9 were
evaluated in vitro for their antimicrobial activities against
the fungi through a Mueller–Hinton broth microdilution
method and with the methodology and interpretative
4-allyl-2-methoxyphenyl b-D-glucopyranoside (7) Brown
crystals, yield: 54 %; m.p. 109–110 °C; [a]D –38.4° (c 0.5
MeOH); IR; tmax in cm-1: 3295 (OH), 3077 (ar. C–H),
123