1470
H.-B. Chu et al. · Chemical Constituents from Pedicularis rex C. B. Clarke
6-O-Ethyl-aucubin (7): white amorphous powder. – 1269, 1035 cm−1. – 1H NMR (400 MHz, CD3OD): δH
=
[α]2D6 = −121.2◦ (c = 0.61, CH3OH). – IR (KBr): ν = 3429, 1.09 (3H, d, J = 6.2 Hz, H-6ꢀꢀꢀ), 3.40 – 4.52 (9H, m, H of
2922, 1644, 1340, 1077, 1044, 1014 cm−1. – 1H NMR sugar), 3.87 (3H, s, -OMe), 4.44 (1H, d, J = 7.9 Hz, H-1ꢀꢀ),
(400 MHz, CD3OD) and 13C NMR (100 MHz, CD3OD) data 4.87 (1H, m, H-4ꢀꢀ), 5.19 (1H, d, J = 1.4 Hz, H-1ꢀꢀꢀ), 6.22 (1H,
are shown in Table 3. – FAB−-MS: m/z = 373 [M–1]−. – HR- m, H-8), 6.34 (1H, d, J = 15.9 Hz, H-α), 6.56 (1H, d, J =
TOF-MS: m/z = 373.1490 (calcd. 373.1498 for C17H25O9, 15.7 Hz, H-7), 6.72 (2H, d, J = 8.6 Hz, H-3, 5), 6.78 (1H, d,
[M–1]−).
J = 8.2 Hz, H-5ꢀ), 7.06 (1H, d, J = 8.2 Hz, H-6ꢀ), 7.17 (1H, d,
J = 1.6 Hz, H-2ꢀ), 7.26 (2H, d, J = 8.6 Hz, H-2, 6), 7.65 (1H,
6-O-Ethyl-epiaucubin (8): white amorphous powder. –
d, J = 15.8 Hz, H-β). – 13C NMR (100 MHz, CD3OD): δC
=
[α]2D6 = −75.0◦ (c = 0.39, CH3OH). – IR (KBr): ν = 3425,
2923, 2345, 1642, 1226, 1079, 1049, 1018 cm−1. – 1H NMR
(400 MHz, CD3OD) and 13C NMR (100 MHz, CD3OD) data
are shown in Table 3. – FAB−-MS: m/z = 373 [M–1]−. – HR-
TOF-MS: m/z = 373.1500 (calcd. 373.1498 for C17H25O9,
[M–1]−).
129.7 (s, C-1), 128.9 (d, C-2), 116.4 (d, C-3), 158.6 (s, C-4),
116.4 (d, C-5), 128.9 (d, C-6), 134.3 (d, C-7), 123.2 (d, C-8),
71.3 (t, C-9), 126.9 (s, C-1ꢀ), 111.8 (d, C-2ꢀ), 149.8 (s, C-3ꢀ),
152.4 (s, C-4ꢀ), 116.8 (d, C-5ꢀ), 124.6 (d, C-6ꢀ), 114.4 (d,
C-α), 148.1 (d, C-β), 168.4 (s, C=O), 56.4 (q, -OMe), 103.1
(d, C-1ꢀꢀ), 76.1 (d, C-2ꢀꢀ), 81.6 (d, C-3ꢀꢀ), 70.7 (d, C-4ꢀꢀ), 76.2
(d, C-5ꢀꢀ), 62.5 (t, C-6ꢀꢀ), 103.0 (d, C-1ꢀꢀꢀ), 72.4 (d, C-2ꢀꢀꢀ),
72.1 (d, C-3ꢀꢀꢀ), 73.8 (d, C-4ꢀꢀꢀ), 70.4 (d, C-5ꢀꢀꢀ), 18.4 (q,
C-6ꢀꢀꢀ). – FAB−-MS: m/z (%) = 633 (30) [M–1]−. – HR-
Aucubin (9): white amorphous powder. – [α]2D6 = −162.2◦
(c = 0.59, H2O). – 1H NMR (400 MHz, CD3OD) and
13C NMR (100 MHz, CD3OD) data are shown in Table 3. –
FAB−-MS: m/z (%) = 345 [M–1]−.
Yuheninoside (10): white amorphous powder. – [α]D29
−130.9◦ (c = 0.58, CH3OH).
=
=
=
TOF-MS: m/z = 633.2197 (calcd. 633.2183 for C31H37O14
,
[M–1]−).
Euphroside (11): white amorphous powder. – [α]D29
−106.4◦ (c = 0.33, CH3OH).
Acknowledgements
Mussaenoside (12): white amorphous powder. – [α]D26
−111.1◦ (c = 0.94, CH3OH).
This work was supported by the Foundation of Chinese
Academy Sciences (West Light Program) and the National
Natural Science Foundation of China (30572258). The au-
4-Hydroxy-phenylpropenyl-α-L-rhamnopyranosyl-(1 →
3)-4-O-feruloyl-β-D-glucopyranoside (13): white amor- thors are grateful to interns Jian-Qiong Xie (Guiyang Med-
phous powder. – [α]D28 = −68.0◦ (c = 0.62, CH3OH). – UV ical College, Guiyang, Guizhou, China) and Jia-Xing Zhu
(MeOH): λ(logε) = 204 (4.53), 271 (4.10), 298 (4.10), 327 (Guiyang College of Traditional Chinese Medicine, Gui-
(4.19) nm. – IR (KBr): ν = 3431, 2928, 1630, 1603, 1515, yang, Guizhou, China) for experimental help.
[1] C. S. Qian, H. Y. Chen, Flora Republicae Popularis
Sinicae, Vol. 68, Science Press, Beijing, 1963, pp. 2.
[2] Jiangshu New Medical College, Chinese Medicine Dic-
tionary, Shanghai People’s Publishing House, Shang-
hai Science and Technology Press, Shanghai, 1977, pp.
286.
[9] A. Yamamoto, S. Nitta, T. Miyase, A. Ueno, L. J. Wu,
Phytochemistry 1993, 32, 421 – 425.
[10] L. Liang, C. Y. Liu, G. Y. Li, L. E. Lu, Y. C. Cai, Acta.
Pharm. Sinica 1996, 31, 122 – 125.
[11] D. M. Song, Q. S. Sun, Chinese Journal of Medicinal
Chemistry 2004, 14, 233 – 235.
[12] Y. L. Ren, J. S. Yang, Chin. Pharm. J. 2001, 36, 590 –
593.
[3] Z. Wu, F. R. Li, J. X. Yang, Lishizhen Med. Materia
Med. Res. 2002, 13, 305 – 307.
[4] Jiangshu New Medical College, Chinese Medicine Dic-
tionary, Shanghai People’s Publishing House, Shang-
hai Science and Technology Press, Shanghai, 1977, pp.
1108.
[5] T. Miyase, A. Ueno, N. Takizawa, H. Kobayashi,
H. Oguchi, Chem. Pharm. Bull. 1987, 35, 3713 –
3719.
[13] A. Bianco, D. Bolli, P. Passacantilli, Gazz. Chim. Ital.
1981, 111, 479 – 481.
[14] Y. Ozaki, S. Johne, M. Hesse, Helv. Chim. Acta. 1979,
62, 2708 – 2711.
[15] S. Otto, S. Osama, Helv. Chim. Acta. 1981, 64, 78 – 81.
[16] C. A. Boros, F. R. Stermitz, J. Nat. Prod. 1990, 53,
1055 – 1147.
[6] G. Appendino, H. C. Ozen, R. Enriu, L. Barboni,
B. Gabetta, G. F. Zini, Fitoterapia 1993, 64, 396 – 398.
[7] J. Shen, J. Liang, S. L. Peng, L. S. Ding, Natural Prod-
uct Research and Development 2004, 16, 391 – 394.
[8] L. Yang, C. G. Wang, Z. J. Jia, Phytochemistry 1995,
40, 491 – 494.
[17] H. Sasaki, H. Nishimura, M. Chin, H. Mitsuhashi, Phy-
tochemistry 1989, 28, 875 – 879.
[18] I. Calis, M. F. Lahloub, E. Rogenmoser, O. Sticher,
Phytochemistry 1984, 23, 2313 – 2315.
Nachdruck – auch auszugsweise – nur mit schriftlicher Genehmigung des Verlags gestattet
Druck: AZ Druck und Datentechnik GmbH, Kempten
Unauthenticated
Download Date | 4/22/16 7:07 AM