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Dehydrosoyasaponin I

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Taxonomy: Physicochemical and Pharmacological Properties of Triterpene Glycosides – Glycosides of Aglycones of Oleanene Type – Soyasapogenol E

Biological source: Abrus cantoniensis [1], Medicago sativa [2], Russell lupine [3], Desmodium styracifolium [4], Phaseolus vulgaris [5]

C48H70O18: 934.456

[α]D27 −25.2° (C5H5N-H2O (1:1), c 0.53) [1]

Mp: 272–280°C [4]

IR (KBr) νmax cm−1: 3420, 1700, 1620 [4]

FAB-MSm/z: 939 (M-H), 793 (M-H-Rha), 631 (M-H-Rha-Gal), 455 (631-GlcUA) [1]

1H NMR (400 MHz, J/Hz, C5D5N): 0.71, 0.86, 0.87, 0.96, 1.17, 1.31, 1.45 (s, CH3 × 7), 5.25 (s, H-12)

α-L-Rhap: 6.28 (s, H-1), 1.78 (d, J = 6.7, CH3-6)

β-D-GlcUAp: 4.99 (d, J = 7.3, H-1)

β-D-Galp: 5.78 (d, J = 7.9, H-1) [1]

13 C NMR (C 5D 5N): [ 1]

Table 1

C-1

38.4

C-16

27.3

GlcUA-1

105.4

Rha-1

102.4

2

26.6

17

47.6

2

78.4

2

72.4

3

91.1

18

47.6

3

77.7

3

72.7

4

43.8

19

46.6

4

73.8

4

74.3

5

55.9

20

34.0

5

77.8

5

69.3

6

18.4

21

50.8

6

172.3

6

18.9

7

32.9

22

215.6

Gal-1

101.7

   

8

39.7

23

22.9

2

78.1...

References

  1. 1.
    H. Miyao, Y. Sakai, T. Takeshita, J. Kinjo, T. Nohara, Chem. Pharm. Bull. 44(6), 1222 (1996)CrossRefGoogle Scholar
  2. 2.
    I. Kitagawa, T. Taniyama, T. Murakami, M. Yoshihara, M. Yoshikawa, Yakugaku Zasshi. 108, 547 (1988) [Chem. Abstr. 109, 196979n (1988)]Google Scholar
  3. 3.
    J. Kinjo, F. Kishida, K. Watanabe, F. Hashimoto, T. Nohara, Chem. Pharm. Bull. 42, 1874 (1994)CrossRefGoogle Scholar
  4. 4.
    T. Kubo, S. Hamada, T. Nohara, Z. Wang, H. Hirayama, K. Ikegami, K. Yasukawa, M. Takido, Chem. Pharm. Bull. 37, 2229 (1989)CrossRefGoogle Scholar
  5. 5.
    M. Yoshikawa, H. Shimada, H. Komatsu, T. Sakurama, N. Nishida, J. Yamahara, H. Shimoda, H. Matsuda, T. Tani, Chem. Pharm. Bull. 45(5), 877 (1997)CrossRefGoogle Scholar

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