Med Chem Res
(CH2, C-16), 39.6 (C-8), 42.1 (CH, C-5), 42.9 (CH, C-20),
45.1 (C-14), 45.8 (C-4), 46.8 (CH, C-18), 48.2 (C-10), 50.7
(CH, C-9), 56.4 (CH3, C-140), 75.5 (CH, C-3), 105.5 (C-80),
119.5 (C-100), 121.3 (CH, C-50), 123.6 (CH, C-12), 123.5
(C-70), 125.9 (C-90), 126.6 (CH, C-120), 127.1 (CH, C-40),
133.7 (CH, C-110), 135.8 (C-30), 154.8 (C-60), 173.5 (C-10),
181.9 (C=O, C-24)ppm; ESI-MS: (m/z): 691 [M?Na]?.
Anal. Calc. For C44H60O5: C, 79.00; H, 9.04; Found: C,
78.67; H, 9.28.
MS: (m/z): 667 [M?Na]?. Anal. Calc. For C43H64O4: C,
80.08; H, 10.00; Found: C, 80.50; H, 9.58.
3-O-Aspirin-11-keto-b-boswellic acid (10)
30
29
20
21
22
19
12
26
3-O-Ibuprofen-b-boswellic acid (9)
O
25
13
15
16
17
11
28
14
1
4
9
18
2
3
8
27
6
O
O
12'
11'
10'
1'
COOH
10
O
O
7'
7'
4'
2'
8'
9'
3'
4'
9'
8'
O
6'
5'
6'
2'
5'
3'
1'
O
COOH
13'
[a]2D5 = ?60.0 (c 0.1, CH2C12); 1H NMR (400 MHz,
CDC13): d = 0.74, 0.86, 0.98, 1.05, 1.19 (m, 21H, 23, 25,
26, 27, 28, 29, 30, –CH3), 1.21, 1.25, 1.36, 1.40, 1.86, 1.92
(m, 16H, CH2 of cyclohexane rings), 1.43, 1.60, 1.63, 1.72,
2.26 (m, 5H, tert. CH of cyclohexane ring), 2.10 (s, 3H,
–COCH3), 4.22 (t, 1H, CH of C3), 5.08 (bs, 1H, H-3),
5.77 (bs, 1H, H-12), 6.82 (m, 2H, Harom., J = 7.29 Hz,
J = 1.64 Hz), 7.41 (m, 1H, Harom., J = 7.1 Hz, J =
1.6 Hz), 7.83 (m, 1H, Harom., J = 1.6 Hz, J = 6.4 Hz),
11.2 (br, 1H, COOH)ppm; 13C NMR (100 MHz, CDC13):
d = 13.4 (CH3, C-4), 16.9 (CH3, C-29), 17.2 (CH3,
C-23), 17.5 (COCH3, C-90), 17.8 (CH2, C-6), 19.7 (CH3,
C-30), 21.3 (CH3, C-27), 21.4 (CH3, C-26), 23.3 (CH3,
C-25), 23.5 (CH2, C-2), 23.8 (CH3, C-28), 28.0 (CH2,
C-1), 28.2 (CH2, C-21), 28.9 (CH2, C-1), 29.2 (CH,
C-20), 29.9 (CH, C-19), 30.3 (C-17), 32.1 (CH2, C-7),
33.5 (CH2, C-15), 33.8 (CH2, C-22), 37.5 (CH2, C-16),
39.6 (C-8), 42.1 (CH, C-5), 45.1 (C-14), 45.8 (C-4), 46.8
(CH, C-18), 48.2 (C-10), 50.7 (CH, C-9), 75.5 (CH, C-3),
121.3 (CH, C-50) 122.6 (CH, C-12), 124.4 (C-60), 125.2
(CH, C-30), 130.1 (CH, C-20), 136.9 (C-40), 149.3 (C-13),
167.5 (C-70), 172.3 (C-80), 181.9 (C=O, C-24), 200.8
(C=O, C-11)ppm; ESI-MS (m/z): 645 [M ? Na]?. Anal.
Calc. For C39H52O7: C, 74.02; H, 8.28; Found: C, 74.50;
H, 8.78.
[a]2D5 = ?23.2 (c 0.1, CH2C12); 1H NMR(400 MHz,
CDC13): d = 0.83, 0.89, 0.92, 0.96, 1.01, 1.11 (21H, 23,
25, 26, 27, 28, 29, 30, –CH3), 0.86 (d, 6H, –CH3 of iso-
propyl group 110and120, J = 3 Hz), 1.22, 1.26, 1.36, 1.41,
1.87, 1.93 (m, 18H, CH2 of cyclohexane rings), 1.43, 1.60,
1.63, 1.72, 2.09 (m, 5H, tert. CH of cyclohexane ring), 1.52
(d, 3H, –CH3-130, b to –COO–, J = 6 Hz), 2.25 (m, 1H,
–CH– of isopropyl group), 2.52 (d, 2H, –CH2-of 90), 3.71
(q, 1H, –CH–CO–), 5.12 (bs, 1H, H-12), 7.11 (d, 2H,
H
arom., J = 6.2 Hz), 7.22 (d, 2H, Harom., J = 6 Hz), 11.30
(br, 1H, OH)ppm; 13C NMR (100 MHz, CDC13): d = 12.4
(CH3, C-4), 16.92 (CH3, C-29), 17.5 (CH3, C-23), 17.3
(CH3, C-130), 17.8 (CH2, C-6), 19.6 (CH3, C-30), 21.5
(CH3, C-27), 21.9 (C-110 and C-120), 23.2 (CH3, C-26),
23.8 (CH3, C-25), 26.6 (CH2, C-2), 28.2 (CH3, C-28), 28.8
(CH2, C-11), 29.2 (CH, C-20), 29.9 (CH, C-19), 30.3 (C-
17), 30.6 (C-100), 31.6 (CH2, C-1), 32.1 (CH2, C-7), 33.2
(CH2, C-21), 33.5 (CH2, C-15), 33.8 (CH2, C-22), 37.5
(CH2, C-16), 39.6 (C-8), 42.1 (CH, C-5), 42.5 (CH, C-20),
44.9 (C-90), 45.1 (C-14), 45.8 (C-4), 46.8 (CH, C-18), 48.2
(C-10), 50.7 (CH, C-9), 75.5 (CH, C-3), 129.1, 129.2 (C-40,
C-50 and C-70, C-80), 123.6 (CH, C-12), 131.8 (C-30), 139.9
(C-60), 173.5 (C=O, C-10), 181.7 (C=O, C-24)ppm; ESI-
123