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Apioglycyrrhizin

Reference work entry

CAS Registry Number: 121709-66-8 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Triterpene Glycosides – Glycosides of Aglycones of Oleanene Type – Glycyrrhetic Acid

Biological source: Glycyrrhiza inflata [1, 2]

C41H62O14: 778.413

Mp: 193–195°C (MeOH) [1]

[α]D23 + 43° (c 0.29, MeOH) [1]

UV λmaxMeOH nm (ε): 249 (9300) [1]

IR (KBr) νmax cm−1: 3500–3100 (br), 2913, 1716, 1650, 1410, 1028 [1]

1H NMR (500 MHz, J/Hz, C5D5N + D2O): 0.89, 1.09, 1.12, 1.23, 1.43 (s, CH3 × 5), 1.34 (s, CH3 × 2), 3.03 (d, J = 14, H-18), 3.38 (dd, J = 4.2, 11.0, Hα-3), 5.95 (s, H-12)

β-D-GlcUAp: 4.96 (d, J = 7.7, H-1), 4.18 (dd, J = 7.7, 9.0, H-2), 4.28 (dd, J = 9.0, 9.0, H-3), 4.44 (dd, J = 9.0, 9.8, H-4), 4.51 (d, J = 9.8, H-5)

β-D-Apif: 6.38 (brs, H-1), 4.90 (brs, H-2), 4.37, 4.69 (Abq, J = 9.4, H2-4), 4.25 (brs, H2-5) [1]

13 C NMR (125 MHz, C 5D 5N-D 2O): [ 1]

Table 1

C-3

88.8

GlcUA-1

105.4

Api-1

110.9

11

199.1

2

79.4

2

77.6

12

128.4

3

79.0

3

80.1

13

169.7

4

73.0

4

75.2

30

178.8

References

  1. 1.
    I. Kitagawa, K. Hori, M. Sakagami, F. Hashiuchi, M. Yoshikawa, J. Ren, Chem. Pharm. Bull. 41(8), 1350 (1993)CrossRefGoogle Scholar
  2. 2.
    I. Kitagawa, M. Sakagami, F. Hashiuchi, J.-L. Zhou, M. Yoshikawa, J. Ren, Chem. Pharm. Bull. 37, 551 (1989)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

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