1
Loganic Acid (3). Í NMR spectrum (500 MHz, ÌåÎÍ-d , ꢃ, ppm, J/Hz): aglycon – 1.07 (3Í, d, J = 7.0, H-10),
4
1.88 (1H, m, H-8), 1.92 (1Í, ddd, J = 14.0, 9.4, 2.6, H-6 ), 2.14 (1Í, ddd, J = 9.0, 8.5, 3.2, H-9), 2.54 (1Í, ddd, J = 14.0, 9.4,
A
6.0, H-6 ), 3.32 (1Í, ddd, J = 9.4, 8.5, 6.1, H-5), 4.18 (1Í, t, J = 4.1, H-7), 5.54 (1Í, d, J = 3.2, H-1), 7.48 (1Í, d, J = 0.8,
B
H-3); 1-O-glucopyranosyl – 3.22 (1Í, dd, J = 9.2, 8.0, H-2ꢀ), 3.38 (1Í, dd, J = 9.2, 9.2, H-4ꢀ), 3.45 (1Í, dd, J = 9.2, 9.2, H-3ꢀ),
13
3.72 (1Í, m, H-5ꢀ), 3.87 (1Í, dd, J = 12.0, 5.6, H-6ꢀ ), 4.03 (1Í, dd, J = 12.0, 2.0, H-6ꢀ ), 4.82 (1Í, d, J = 8.0, H-1ꢀ). C NMR
B
A
spectrum (125 MHz, ÌåÎÍ-d , ꢃ, ppm): aglycon – 14.5 (C-10), 32.3 (C-5), 42.2 (C-8), 42.6 (C-6), 46.9 (C-9), 77.2 (C-7),
4
98.9 (C-1), 115.2 (C-4), 152.8 (C-3), 173.7 (C-11); 1-O-glucopyranosyl – 63.1 (C-6ꢀ), 71.8 (C-4ꢀ), 74.8 (C-2ꢀ), 76.4 (C-3ꢀ),
76.9 (C-5ꢀ), 101.5 (C-1ꢀ).
1
Methyl 2,3-Dihydroxybenzoate. Í NMR spectrum (500 MHz, ÌåÎÍ-d , ꢃ, ppm, J/Hz): 3.82 (3H, s, COOCH ),
4
3
13
6.67 (1Í, t, J = 8.0, H-5), 7.02 (1Í, dd, J = 8.0, 1.9, H-4), 7.28 (1Í, dd, J = 8.0, 1.9, H-6). C NMR spectrum (125 MHz,
ÌåÎÍ-d , ꢃ, ppm): 52.2 (COOCH ), 114.0 (C-1), 118.8 (C-5), 120.3 (C-6), 121.4 (C-4), 145.7 (C-3), 150.4 (C-2), 170.1 (C-7).
4
3
Anti-inflammatory activity was studied using a mouse-ear inflammation model and 12-O-tetradecanoylphorbol acetate
to induce inflammation (ꢋ99%, Sigma-Aldrich) [22]. Compounds were dissolved in normal saline (0.9%). The reference
drug was indomethacin (ꢋ99%, Pfizer, New York, NU, USA). The control group received normal saline. Results were expressed
in percent inhibition of edema relative to the control group.
ACKNOWLEDGMENT
The work was sponsored by RFBR Project No. 16-03-00039.
REFERENCES
1.
2.
3.
4.
R. X. Tan, J.-L. Wolfender, W. G. Ma, L. X. Zhang, and K. Hostettmann, Phytochemistry, 41, 111 (1996).
Tibetan Medicine in Buryatia [in Russian], SB RAS, Novosibirsk, 2008, 324 pp.
M. M. Tadzhibaev, A. V. Butayarov, E. Kh. Batirov, and V. M. Malikov, Chem. Nat. Compd., 28, 244 (1992).
A. V. Butayarov, E. Kh. Batirov, M. M. Tadzhibaev, E. E. Ibragimov, and V. M. Malikov, Chem. Nat. Compd.,
29, 805 (1993).
5.
6.
7.
8.
9.
M. M. Tozhiboev, E. Kh. Botirov, and G. A. Usmanova, Russ. J. Bioorg. Chem., 37, 866 (2011).
R. X. Tan, J. Hu, L. D. Kong, J.-L. Wolfender, and K. Hostettmann, Planta Med., 63, 567 (1997).
A. M. Yang, H. Li, J. L. Liu, H. Han, and J. Sun, Chem. Nat. Compd., 49, 755 (2013).
A. M. Yang, H. Han, J. Y. Li, and R. Wu, Chem. Nat. Compd., 51, 381 (2015).
D. N. Olennikov, N. I. Kashchenko, N. K. Chirikova, L. P. Koryakina, and L. N. Vladimirov, Molecules,
20, 20014 (2015).
10.
11.
12.
D. N. Olennikov, N. I. Kashchenko, N. K. Chirikova, and L. M. Tankhaeva, Molecules, 20, 19172 (2015).
M. Wu, P. Wu, M. Liu, H. Xie, Y. Jiang, and X. Wei, Phytochemistry, 70, 746 (2009).
C. A. Carbonezi, D. Martins, M. C. M. Young, M. N. Lopes, M. Furlan, E. Rodrigues Filho, and V. da S. Bolzani,
Phytochemistry, 51, 781 (1999).
13.
N. Tanaka, M. Takekata, S.-I. Kurimoto, K. Kawazoe, K. Murakami, D. Damdinjav, E. Dorjbal, and Y. Kashiwada,
Tetrahedron Lett., 56, 817 (2015).
14.
15.
E. M. Mpondo and A. J. Chulia, Plant Med., 54, 185 (1988).
R. X. Tan, J.-L. Wolfender, L. X. Zhang, W. G. Ma, N. Fuzzati, A. Marston, and K. Hostettmann, Phytochemistry,
42, 1305 (1996).
16.
17.
18.
19.
E. M. Mpondo, J. Garcia, G. Cartier, and G. Pellet, Planta Med., 56, 334 (1990).
X. Zhang, Q. Xu, H. Xiao, and X. Liang, Phytochemistry, 64, 1341 (2003).
L. J. El-Naggar and J. L. Beal, J. Nat. Prod., 43, 649 (1980).
Y. Suyama, S.-I. Kurimoto, K. Kawazoe, K. Murakami, H.-D. Sun, S.-L. Li, Y. Takaishi, and Y. Kashiwada,
Fitoterapia, 91, 166 (2013).
20.
21.
22.
H. Inouye, S. Ueda, Y. Nakamura, K. Inoue, T. Hayano, and H. Matsumura, Tetrahedron, 30, 571 (1974).
Y. Ikeshiro, I. Mase, and Y. Tomita, Planta Med., 56, 101 (1990).
D. Carrillo-Ocampo, S. Bazaldua-Gomez, J. R. Bonilla-Barbosa, R. Aburto-Amar, and V. Rodriguez-Lopez, Molecules,
18, 12109 (2013).
641