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Cayaponoside B5

Reference work entry

CAS Registry Number: 163047-18-5 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Triterpene Glycosides – Glycosides of Aglycones of Cucurbitane Type – 22-Hydroxy-6,25-dien-fevicordin A

Biological source: Cayaponia tayuya [1]

C35H48O11: 644.319

Mp: 168–175°C [1]

[α] D 26 − 90.7° (c 0.98, MeOH) [1]

UV λ max MeOH nm (log ε): 206 (4.11), 233 (4.36), 274 (3.85), 284 (3.82), 303 (3.47), 315 (3.37) [1]

FAB-MS m/z: 643 [M-H], 481 [M-H-162], 383 [1]

HR-FAB-MS m/z: 667 [M + Na]+ [1]

1 H NMR (J/Hz): 6.53 (s, H-1), 6.88 (d, J = 10, H-6), 5.82 (dd, J = 6, 10, H-7), 2.57 (d, J = 6, H-8), 2.67, 2.87 (dd, J = 15, H2-12), 1.48 (d, J = 14), 2.08 (dd, J = 8, 14, H2-15), 4.65 (dd, J = 6, 8, H-16), 2.36 (d, J = 6, H-17), 1.05 (s, CH3-18), 1.21 (s, CH3-19), 1.21 (s, CH3-21), 4.08 (dd, J = 1, 6, H-22), 5.80 (dd, J = 6, 10, H-23), 6.36 (dd, J = 1, 6, H-24), 4.95 (s, H2-26), 1.82 (s, CH3-27), 2.23 (s, CH3-28), 0.92 (s, CH3-30)

β-D-Glcp: 4.61 (d, J = 7, H-1), 3.40–3.55 (H-2, 3, 4), 3.31 (m, H-5), 3.83 (dd, J = 4, 12, Ha-6), 3.95 (dd, J = 2, 12, Hb-6) [1]

13 C NMR: [1]

Table 1

C-1

113.5

C-16

73.3

Glc-1

105.8

2

146.1

17

58.2

2

75.6

3

146.5

18

21.0

3

78.5

4

124.1

19

27.4

4

71.8

5

130.6

20

77.9

5

79.0

6

126.9

21

24.4

6

63.0

7

130.4

22

82.2

  

8

48.9

23

128.1

  

9

52.6

24

136.6

  

10

129.1

25

143.8

  

11

217.1

26

117.5

  

12

53.2

27

19.6

  

13

51.9

28

12.0

  

14

50.6

29

   

15

44.8

30

18.7

  

Pharm./Biol.: Inhibitory effect on Epstein-Barr Virus activation [1]

References

  1. 1.
    E. Himeno, T. Nagao, J. Honda, H. Okabe, N. Irino, T. Nakasumi, Chem. Pharm. Bull. 42(11), 2370 (1994)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013

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