6-O-(4′-Chlorophenacyl)-1,8-dihydroxy-3-methylanthraquinone (6). C H ClO , mp 223–225°C, R 0.92,
23 15
6
f
C H :EtOAc (4:1), 0.81 hexane:EtOAc (2:1). UV spectrum (CH CN, λ , nm): 223, 255, 285, 305, 433. IR spectrum (KBr,
6
6
3
max
−1
+
ν, cm ): 1686 (C=O ), 1625, 1610 (C=O ), 1585 (C=C, Ar). Mass spectrum (EI, 70 eV, m/z): 422 [M] , 139 (100), 125
sub
anth
(4), 111 (25), 75 (15), 50 (7).
PMR spectrum (CDCl , δ, ppm, J/Hz): 2.45 (3H, s, CH -3), 6.70 (1H, d, J = 2.57, H-7), 7.10 (1H, s, H-2), 7.38 (1H,
3
3
d, J = 2.57, H-5), 7.62 (1H, d, J = 2.0, H-4), 12.05 (1H, s, α-OH), 12.26 (1H, s, α-OH); protons of 6-substituent: 5.40 (2H, s,
CH ), 7.52 (2H, dd, >CH–, Ar), 7.94 (2H, dd, >CH–, Ar).
2
6-O-(4′-Bromophenacyl)-1,8-dihydroxy-3-methylanthraquinone (7). C H BrO , mp 228–230°C, R 0.94,
23 15
6
f
C H :EtOAc (4:1), 0.83 hexane:EtOAc (2:1). UV spectrum (CH CN, λ , nm): 223, 256, 285, 305, 434. IR spectrum (KBr,
6
6
3
max
−1
+
ν, cm ): 1688 (C=O ), 1626, 1609 (C=O ), 1586 (C=C, Ar). Mass spectrum (EI, 70 eV, m/z): 467 [M] , 253 (5), 183
sub
anth
(100), 169 (10), 155 (20), 139 (22), 115 (7), 76 (15), 50 (10).
PMR spectrum (DMSO-d , δ, ppm, J/Hz): 2.44 (3H, s, CH -3), 6.99 (1H, s, H-7), 7.22 (1H, s, H-2), 7.27 (1H,
6
3
s, H-5), 7.55 (1H, s, H-4), 11.97 (s, α-OH), 12.15 (s, α-OH); protons of 6-substituent: 5.86 (2H, s, –CH –), 7.80 (2H, dd,
2
>CH–, Ar), 7.95 (2H, dd, >CH–, Ar).
ACKNOWLEDGMENT
We thank Prof. E. Tramontano for help in testing samples for HIV-1 RNase H activity. The work was supported
financially by Grant EC-INTAS 04-82-7146.
REFERENCES
1.
2.
3.
4.
5.
R. H. Thomson, Naturally Occurring Quinones III, Chapman and Hall, New York, 1987, pp. 345-526.
Q. Huang, G. Lu, H. M. Shen, M. C. Chung, and C. N. Onq, Med. Res. Rev., 27, 609 (2007).
G. Srinivas, S. Babykutty, P. P. Sathiadevan, and P. Srinivas, Med. Res. Rev., 27, 591 (2007).
H. Yim, Y. H. Lee, C. H. Lee, and S. K. Lee, Planta Med., 65, 9 (1999).
M. Koyama, K. Takahashi, T. C. Chou, Z. Darzynkiewicz, J. Kapuscinski, T. R. Kelly, and K. A. Watanabe, J. Med.
Chem., 32, 1594 (1989).
6.
7.
S. O. Muller, W. K. Lutz, and H. Sopper, Mutat. Res., 414, 125 (1998).
J. H. Tan, Q. X. Zhang, Z. S. Huang, Y. Chen, X. D. Wang, L. Q. Gu, and J. Y. Wu, Eur. J. Med. Chem., 41, 1041
(2006).
8.
9.
D. L. Barnard, J. H. Huffman, J. L. B. Morris, S. G. Wood, B. G. Hughes, and R. W. Sidwell, Antiviral Res., 17, 63
(1992).
D. Shuangsuo, Z. Zhengguo, C. Yunru, Z. Xin, W. Baofeng, Y. Lichao, and C. Yan′an, Med. Sci. Monit., 12, 302
(2006).
10.
11.
12.
13.
14.
15.
K. Agarwal, S. S. Singh, S. Verma, and S. Kumar, J. Ethnopharmacol., 72, 43 (2000).
K. E. Malterud, T. L. Farbrot, A. E. Huse, and R. B. Sund, Pharmacology, 47 (Suppl. 1), 77 (1993).
H. C. Huang, J. H. Chang, S. F. Tung, R. T. Wu, M. L. Foegh, and S. H. Chu, J. Pharmacol., 211, 359 (1992).
H. Matsuda, H. Shimoda, T. Morikawa, and M. Yoshikawa, Bioorg. Med. Chem. Lett., 11, 1839 (2001).
I. Izhaki, New Phytol., 155, 205 (2002).
T. Pecere, F. Sarinella, C. Salata, B. Gatto, A. Bet, F. D. Vecchia, A. Diaspro, M. Carli, M. Palumbo, and G. Palu,
Int. J. Cancer, 106, 836 (2003).
16.
H. Jayasuriya, N. M. Koonchanok, R. L. Geahlen, J. L. McLaughlin, and C. J. Chang, J. Nat. Prod., 55, 696
(1992).
17.
18.
19.
20.
21.
Flora of Kazakhstan [in Russian], Vol. 3, Izd. Akad. Nauk Kaz. SSR, Alma-Ata, 1960.
T. V. Kharlamova, Khim. Prir. Soedin., 324 (2007).
Y.-M. Kim, C.-H. Lee, H.-G. Kim, and H.-S. Lee, J. Agric. Food Chem., 52, 6096 (2004).
E. Tramontano, F. Esposito, R. Badas, R. Di Santo, R. Costi, and P. La Colla, Antiviral Res., 65, 117 (2005).
F. Dezinot and R. Lang, J. Immunol. Methods, 89, 271 (1986).
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