2704
H. Gao, Z. Wang / Phytochemistry 67 (2006) 2697–2705
407, 313, 248(100), 219, 203(95), 189. 13C NMR(C5D5N) d:
179.9,139.2, 125.7, 78.1, 68.8, 66.3, 53.1, 48.1, 47.9, 47.7,
46.9, 42.5, 42.1, 39.9, 39.8, 39.3, 38.2, 37.4, 33.2, 31.0,
28.5, 24.8, 23.8, 23.7, 21.3, 18.4, 17.5, 17.3, 17.2, 14.4.
Chinese Academy of Sciences, 2001. Flora of ChinaTomus 29. Science
Press, Beijjing, China, pp. 1–49, 305–306.
Committee for the Pharmacopoeia of P.R. China, 2005. Pharmacopoeia of
P.R. China. Part I. Chemical Industry Press, Beijing, China, P.43.
Damtoft, S., Jensen, S.R., 1994. Three phenylethanoid glucosides of
unusual structure from Chirita sinensis (Gesneriaceae). Phytochemistry
37, 441–443.
Fujita, M., Itokawa, H., Kumekawa, Y., 1974a. The study on the
constituents of Clematisand Akebia spp. I. Distribution of triterpenes
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Phytochemistry 25, 1625–1628.
4.3.4.2. Acid Hydrolysis of 3. A solution of 3(22.5 mg) was
hydrolysed and analyzed as above for compound 2.
4.3.5. Compound 4
27
Amorphous solid. ½aꢁD +13.5(MeOH; c0.1133). ESI-MS
(positive mode): 1243[M+Na]+, 927[M+H-ara-glc]+, HR-
ESI-MS (positive mode): m/z 1243.5719 [M+Na]+
(Calc.: 1243.5724). 1H NMR(C5D5N) d: 6.19(1H, d,
J = 8.0 Hz, glc-H-1), 5.84(1H, br.s, rham-H-1), 5.31(1H,
d, J = 8.0 Hz, glc0 0-H-1), 4.98(1H, d, J = 6.0 Hz, glc0-H-1),
4.94(1H, d, J = 7.5 Hz, ara-H-1), 4.72,4.66(each s, H-29),
5.42(1H, br.s, H-12), 3.10(1H, dd, J = 13.0, 4.5 Hz, H-18),
1.69(3H, d, J = 6.5 Hz, rham-H-6), 1.13(3H, s,
H-27), 1.08(3H, s, H-26), 0.94(3H, s, H-25), 0.93(3H, s, H-
24). For 13C NMR spectroscopic data, see Tables 1 and 2.
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trifoliata and comparison with the constituents of other Lardizabal-
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Itokawa, H., Ikuta, A., 1989. 30-noroleanane saponins from callus tissues
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Kawasaki, T., Higuchi, R., 1972. Seed saponins of Akebia quinata Decne
II. Hederagenin 3,28-O-bisglycosides. Chem. Pharm. Bull. 20, 2143–
2149.
Kawasaki, T., Higuchi, R., 1976a. Pericarp saponins of Akebia quinata
Decne I. Glycosides of hederagenin and oleanolic acid. Chem. Pharm.
Bull. 24, 1021–1032.
Kawasaki, T., Higuchi, R., 1976b. Pericarp saponins of Akebia quinata
Decne II. Arjunolic and norarjunolic acids, and their glycosides. Chem.
Pharm. Bull. 24, 1314–1323.
Lin, geng, Yang, J.S., 2004. Studies on the chemical constituents of Aralia
decaisneane. Chin. Pharm. J. 39, 575–578.
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faminal relationship of Ranunculid. Plant Syst. Evol. 9, 99–118.
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from the seed of Akebia trifoliate. Chin. Traditional Herb Drug 24,
563–566.
4.3.5.1. Acid Hydrolysis of 4. A solution of 4 (5.5 mg) was
hydrolysed and analyzed as for compound 2.
4.3.6. Compound 5
Amorphous
solid.
ESI-MS
(positive
mode):
1197[M+Na]+, 867[M+H-ram-glc]+, FAB-MS(positive
mode): 1197[M+Na]+, 1175[M+H]+, 1043[M+H-xyl]+,
911[M+H-xyl-ara]+,
765[911-rham]+,
603[765-glc]+,
423[aglycone-H2O]+, HR-ESI-MS (positive mode): m/z
1197.5627 [M+Na]+(Calc.: 1197.5669). H NMR(C5D5N)
1
d: 6.21(1H, d, J = 8.0 Hz, glc-H-1), 5.87(1H, br.s, rham-H-
1), 5.08(1H, d, J = 4.0 Hz, xyl-H-1), 4.97(1H, d,
J = 7.5 Hz, glc0-H-1),4.88(1H, d, J = 5.0 Hz, ara-H-1),
5.42(1H, br.s, H-12), 4.74, 4.68(each 1H, s, H-29, 3.25(1H,
dd, H-18), 2.56, 2.17(each 1H, H-19), 1.25(3H, s, H-23),
1.20(3H, s, H-27), 1.07(6H, s, H-26, H-24), 0.88(3H, s, H-
25). For 13C NMR spectroscopic data, see Tables 1 and 2.
Ma, S.C., Chen, D.C., Zhao, S.J., 1994a. The study on the constituents of
yuzhizioside(I). Chin Traditional Herb Drugs 25, 171–174.
Ma, S.C., Chen, D.C., Zhao, S.J., 1994b. The study on the constituents of
yuzhizioside(II). Chin Traditional Herb Drug 25, 613.
Maeda, C., Ohtani, K., Kasai, R., Nguyen, M.D., 1994. Oleanane and
ursane glycosides from Scheffleraoctophylla. Phytochemistry 37, 1131–
1137.
4.3.6.1. Acid Hydrolysis of 5. A solution of 5 (3.0 mg) was
hydrolysed and analyzed as for compound 2.
Acknowledgements
Mahato, S.B., Sahu, N.P., Luger, P., Muller, E., 1987. Stereochemistry of
a triterpenoid trisaccharide from Centella asiatica X-ray determination
of the structure of asiaticoside. J. Chem. Soc. Perkin Trans. II, 1509–
1515.
Mimaki, Y., Kuroda, M., Yokosuka, A., Harada, H., Fukushima, M.,
Sashida, Y., 2003. Triterpenes and triterpene saponins from the stems
of Akebia trifoliata. Chem. Pharm. Bull. 51, 960–965.
Shao, C.J., Kasai, R., Xu, J.D., Tanaka, O., 1989. Saponins from leaves of
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Shimomura, H., Sashida, Y., Adachi, T., 1987. Cyanogenic and phenyl-
propanoid glucosides from Prunus grayana. Phytochemistry 26, 2363–
2366.
We thank Professor Tu Guangzhong for NMR mea-
surements and Doctor Xueyan for MS measurements. This
study was supported by the National High Technology Re-
search and Development Project of China (No:
2004AA223730-14).
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