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This document describes the chemical structure and properties of two saponins extracted from plants: 1) Agapanthusaponin D, extracted from Agapanthus inapertus, with a molecular weight of 934 and molecular formula of C45H74O20. It has a spirostane core with sugar chains. 2) Ampeloside Bs1, extracted from Allium ampeloprasum, with the same molecular weight and formula as Agapanthusaponin D. It has an agigenin core with sugar chains. Both compounds were analyzed using techniques like IR, NMR, and mass spectrometry to determine their structure.

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56 views2 pages

Fulltext 16

This document describes the chemical structure and properties of two saponins extracted from plants: 1) Agapanthusaponin D, extracted from Agapanthus inapertus, with a molecular weight of 934 and molecular formula of C45H74O20. It has a spirostane core with sugar chains. 2) Ampeloside Bs1, extracted from Allium ampeloprasum, with the same molecular weight and formula as Agapanthusaponin D. It has an agigenin core with sugar chains. Both compounds were analyzed using techniques like IR, NMR, and mass spectrometry to determine their structure.

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iramshagufta
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© Attribution Non-Commercial (BY-NC)
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1602

IR (KBr) : 3388 (OH), 920, 826, 800 cm1.


PMR (C5D5N, 400 MHz) : G 0.68 (d, J=5.5 Hz, 3xH-27), 0.88 (s, 3xH-18, 1.11 (s, 3xH-19), 1.20 (d, J=7.3 Hz, 3xH21), 3.26 (t, J=10.3 Hz, H-26ax), 3.46 (m, H-26 eq) 4.89 (d, J=7.9 Hz, H-1 of Gal), 5.12 (d, J=7.9 Hz, H-1 of Glc II),
5.20 (d, J=7.3 Hz, H-1 of Glc I), 5.38 (br s, H-6).
CMR (C5D5N, 100 MHz) : G C-1) 37.5 (2) 30.2 (3) 78.1 (4) 39.1 (5) 140.1 (6) 122.5 (7) 32.9 (8) 32.2 (9) 50.2 (10)
36.9 (11) 20.9 (12) 40.7 (13) 40.7 (14) 59.9 (15) 79.0 (16) 91.2 (17) 60.7 (18) 14.7 (19) 19.4 (20) 35.7 (21) 16.8 (22)
111.4 (23) 67.3 (24) 38.6 (25) 31.6 (26) 65.9 (27) 17.8 Gal (1) 102.5 (2) 73.2 (3) 75.0 (4) 80.9 (5) 75.4 (6) 60.3 Glc I
(1) 105.1 (2) 86.0 (3) 77.5 (4) 70.2 (5) 78.3 (6) 61.4 Glc II (1) 106.8 (2) 76.6 (3) 78.8 (4) 71.7 (5) 78.1 (6) 63.1.
Mass (FAB, Positive ion) : m/z 955.9493 [(M+Na)+ requires 955.4515].
Mass (FAB, Negative ion) : m/z 931 [M-H], 769 [M-H-Hexose], 607 [M-H-2xHexose].
Reference

1.

S. Okamura, K. Shingu, S. Yahara, H. Kohoda and T. Nohara, Chem. Pharm. Bull., 40, 2981 (1992).

AGAPANTHUSSAPONIN D
(25R)-5D-Spirostane-2D,3E,5D,9D-tetrol 3-O-{D-L-rhamnopyranosyl-(1o2)-[E-D-galactopyranosyl-(1o3)]E-D-glucopyranoside}
Source : Agapanthus inapertus (Liliaceae)
Mol. Formula : C45H74O20
Mol. Wt. : 934
[D]D23 : -50.0o (c=0.10, MeOH)
Registry No. : [155740-00-4]
O

O
HO
OH
HOH2C

O
O

Glc

HOH2C
HO

Gal

HO

OH

HO

Rha

OH

CH3
HO

OH

OH

1603

IR (KBr) : 3400 (OH), 2930 (CH), 1445, 1375, 1240, 1175, 1065, 1045, 980, 960, 915, 895, 865 cm1.
PMR (C5D5N, 400/500 MHz) : G 0.68 (d, J=5.3 Hz, 3xH-27), 0.92 (s, 3xH-18), 1.09 (d, J=6.9 Hz, 3xH-21), 1.23 (s,
3xH-19), 1.48 (br d, J=12.8 Hz, H-12eq), 1.68 (d, J=6.2 Hz, 3xH-6 of Rha), 1.82 (ddd, J=12.8, 12.8, 3.6 Hz, H-12ax),
1.96 (ddd, J=13.0, 13.0, 5.9 Hz, H-8), 2.09 (dd, J=12.1, 5.3 Hz, H-1eq), 2.24 (dd, J=13.6, 11.4, H-4ax), 2.35 (dd,
J=13.6, 5.9 Hz, H-4eq), 2.78 (dd, J=12.1, 12.1 Hz, H-1ax), 3.47 (dd, J=10.5, 10.5 Hz, H-26A), 3.54 (br d, J=10.5, H26B), 4.35 (ddd, J=12.1, 9.1, 5.3 Hz, H-2), 4.59 (q-like, J=7.4 Hz, H-16), 4.71 (ddd, J=11.4, 9.1, 5.9 Hz, H-3), 4.80 (d,
J=7.3 Hz, H-1 of Glc), 4.93 (d, J=7.8 Hz, H-1 of Gal), 6.24 (br s, H-1 of Rha).
CMR (C5D5N, 100/125 MHz) : G C-1) 35.1 (2) 70.8 (3) 82.3 (4) 40.6 (5) 76.7 (6) 34.8 (7) 21.9 (8) 37.4 (9) 77.4 (10)
43.2 (11) 28.1 (12) 35.4 (13) 41.0 (14) 48.9 (15) 32.1(16) 81.4 (17) 63.1 (18) 16.0 (19) 20.3 (20) 42.0 (21) 15.0 (22)
109.3 (23) 31.9 (24) 29.3 (25) 30.6 (26) 66.9 (27) 17.3 Glc (1) 100.7 (2) 77.2 (3) 89.3 (4) 69.6 (5) 77.8 (6) 62.2 Gal
(1) 102.2 (2) 72.4 (3) 72.8 (4) 74.1 (5) 69.6 (6) 18.6 Rha (1) 105.2 (2) 72.4 (3) 75.3 (4) 70.1 (5) 77.4 (6) 62.1.
Mass (FAB, Negative ion) : m/z 933 [M-H], 788 [M-Rha], 772 [M-Gal].
Inhibitory Activity : Shows inhibitory activity on cAMP phosphodiesterase (IC50=2.0x10-5 M).
Reference

1.

O. Nakamura, Y. Mimaki, Y. Sashida, T. Nikaido and T. Ohmoto, Chem. Pharm. Bull., 41, 1784 (1993).

AMPELOSIDE Bs1
Agigenin 3-O-[E-D-glucopyranosyl-(1o3)-E-D-glucopyranosyl-(1o4)-E-D-galactopyranoside]
Source : Allium ampeloprasum L. (Liliaceae)
Mol. Formula : C45H74O20
Mol. Wt. : 934
M.P. : <300oC
[D]D17 : -52.5o (c=1.12, C5H5N)
Registry No. : [118524-12-2]
O

O
HO

HOH2C

HOH2C

O
Glc
HOH2C

Glc O
II

Gal O

OH

HO

OH
HO

OH

OH

OH

H
OH

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