A new acylated and oleanane-type triterpenoid saponin from Gypsophila arrostii roots

Figures & data

Table 1. ¹H and ¹³C NMR spectral data for the aglycone, sugar, and acyl moieties of GS1 in pyridine d_5.

	δ ^1H (J in Hz)	δ ^13C		δ ^1H (J in Hz)	δ ^13C		δ ^1H (J in Hz)	δ ^13C
Aglycone			3-O-sugars			28-O-sugars
1	1.40 m/0.80 m	38.0	Glc			Rha
2	1.90 m/2.14 m	24.7	1	5.20 d (7.0)	104.6	1	5.92 d (1.0)	102.2
3	4.10 m	86.2	2	4.06	80.3	2	4.50 br s	74.2
4	–	56.2	3	4.24	84.2	3	4.90 d	75.0
5	1.48 m	49.7	4	4.50	71.3	4	3.98	72.6
6	1.28 m/1.58 m	20.0	5	4.53	78.0	5	3.98	64.8
7	0.88 m/1.46 m	34.6	6	4.20/1.40	60.6	6	1.46 d (6.0)	16.2
8	–	44.8	Xyl			Xyl’’
9	1.86 m	48.8	1	5.50 d (7.7)	104.2	1	6.05 d (7.0)	103.8
10	–	36.1	2	4.40	73.6	2	5.05	80.2
11	1.86 m/1.92 m	24.5	3	4.20	75.6	3	4.86	82.2
12	5.55 m	122.8	4	4.44	70.7	4	4.55	78.3
13	–	146.8	5	4.41/4.20	69.0	5	3.20/3.98	18.8
14	–	48.2	Xyl’			Glc’
15	1.88 m/2.20 d	36.2	1	5.31 d (7.7)	105.6	1	5.60 d (7.0)	105.4
16	3.35 m	35.8	2	3.98	70.6	2	4.20	75.0
17	–	52.2	3	4.20	78.4	3	4.10	78.4
18	3.18 br d	42.5	4	4.12	72.0	4	4.02	71.8
19	2.60 t/1.28 m	47.3	5	3.40/4.23	68.8	5	3.98	78.4
20	–	30.2				6	4.20/4.60	76.0
21	5.18 br s	87.0	TMC–α	–	168.0	Ara
22	2.28 m 2.48 m	30.6	β	6.66 d 16.1	118.0	1	5.62 d (7.7)	104.5
23	9.76 s	210.4	γ	7.96 d 16.1	129.6	2	3.96	79.4
24	1.46 s	14.8	1	–	130.2	3	4.12	76.7
25	0.86 s	15.8	2,6	6.85 s	106.0	4	4.14	71.0
26	1.15 s	17.0	3,5	–		5	4.10	74.0
27	1.76 s	26.8	4	–		6	3.50/4.18	67.2
28	–	176.8	OCH3 at C3	3.88 s	56.0
29	0.93 s	32.8	OCH3 at C4	3.90 s	60.2
30	0.96 s	24.4	OCH3 at C5	3.88 s	56.2

Figure 1. Structure of acylated GS1 (MW 1689 da) isolated from Gypsophila arrostii roots. compound was ascertained by ¹H, ¹³C and 2D NMR and compared with literature data.^[13]

Figure 2. Proposed fragmentation of sugar and acyl groups of GS1 in the positive ion mode; (a) elinination of Xyl moiety (132 Da), (b) fragmentation of Glc moiety (162 Da), (c) 3C and (d) 28C sugar neutral losses (1026 Da) and elimination of trimethoxycinnamoil-TMC group (193 Da).