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Glycoside 10

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Taxonomy: Physicochemical and Pharmacological Properties of Triterpene Glycosides – Glycosides of Aglycones of Ursene Type – Quinovic Acid

Biological source: Uncaria tomentosa [1], Isertia haenkeana [2], Bhesa paniculata [3]

C42H66O14: 794.445

Mp: 208–210°C [2]

[α]D20 + 20.0° (c 1.0, EtOH) [2]

IR (KBr) νmax cm−1: 3400, 2925, 1730, 1690, 1630 [2]

FAB-MSm/z: 793 [M-H], 647 [M-H-146], 631 [M-H-162], 615 [M-H-178], 603 [793-(44 + 146)], 587 [793-(44 + 162)], 571 [793-(44 + 178)], 441 [603-162 or 587-146], 425 [603-178 or 587-162] [1]

1H NMR (250 MHz, J/Hz, CD3OD): 0.85, 0.89, 0.96, 0.96, 1.04 (s, CH3-23, 26, 29, 30, 25, 24), 5.59 (m, H-12)

β-D-Quip: 4.32 (d, J = 7.0, H-1), 1.30 (d, J = 6.0, CH3-6)

β-D-Glcp: 5.42 (d, J = 7.5, H-1) [1]

13 C NMR (50.3 MHz, C 5D 5N) (aglicone moiety): [ 2]

Table 1

C-1

38.7

C-16

25.1

Qui-1

106.2

2

26.4

17

48.6

2

75.3

3

88.2

18

54.3

3

77.8

4

39.1

19

38.7

4

76.4

5

55.5

20

37.1

5

72.2

6

18.2

21

29.9

6

18.8

7

37.1

22

36.0

Glc-1

95.2

8

39.8...

References

  1. 1.
    R. Aquino, F. De Simone, C. Pizza, C. Conti, M.L. Stein, J. Nat. Prod. 52, 679 (1989)CrossRefGoogle Scholar
  2. 2.
    F.J. Arriaga, A. Rumbero, P. Vazquez, Phytochemistry 29, 209 (1990)CrossRefGoogle Scholar
  3. 3.
    K. Ohashi, H. Kojima, T. Tanikawa, Y. Okumura, K. Kawazoe, N. Tatara, H. Shibuya, I. Kitagawa, Chem. Pharm. Bull. 42(8), 1596 (1994)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013

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