SUPPLEMENTARY MATERIAL
New pregnane glycoside derivative from Caralluma retrospiciens (Ehrenb)
Mahmoud Fahmi Elsebaia,c,*, Ietidal EL-Tahir Mohamedb
a
Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt.
b
Department of Botany, Faculty of Science, University of Khartoum, Khartoum, Sudan.
c
Department of Chemistry, University of Oulu, Oulu, Finland.
* Corresponding authors: Mahmoud Fahmi Elsebai: Department of Pharmacognosy, Faculty of
Pharmacy, Mansoura University, Mansoura, Egypt. Tel: +2-050- 2246253, Fax+2-050- 2247496.
E-mail: elsebai72@yahoo.com
Abstract
Retrospinoside (1) is a new polyoxypregnane glycoside which was isolated and
characterised from the aerial parts of Caralluma retrospiciens (Ehrenb.) N. E.
Br., family Apocynaceae. The structure was established as 3-O-[β-Dglucopyranosyl-(1→4)-β-D-(3-O-methyl-6-desoxygalactopyranosy)]-14,15,20trihydroxy- 4β-pregnane. Its structural elucidation was performed through
extensive spectroscopic measurements including 1D- and 2D-NMR, and HRMS,
in addition to chemical methods.
Keywords: plant natural products; pregnane glycosides; polyoxypregnanes; Caralluma
retrospiciens
1
Table S1: 13C NMR (CD3OD) spectroscopic data of compound 1 and
(C5D5N) of caratuberside B
13C
NMR data
No.
1
Multiplicities
CH2
δC (ppm) of 1
38.4
δC (ppm) of caratubersideBa
37.6
2
CH2
30.4
30.1
3
CH
71.8
72.0
4
CH2
38.4
34.8
5
CH
45.6
44.6
6
CH2
30.2
29.4
7
CH2
27.9
28.1
8
CH
41.7
40.9
9
CH
50.5
50.0
10
C
37.2
36.1
11
CH2
21.5
22.8
12
CH2
41.4
40.9
13
C
47.7
49.0
14
C
82.9
83.8
15
CH
73.4
33.0 (CH2)
16
CH2
35.3
18.9
17
CH
55.0
57.0
18
CH3
12.7
12.3
19
CH3
17.3
15.4
20
CH
71.4
65.3
21
CH3
21.5
21.5
Gala- 1`
CH
102.7
102.5
2`
CH
75.9
76.8
3`
CH
85.7
85.5
4`
CH
77.8
77.4
5`
CH
71.6
70.5
6`
CH3
17.3
17.8
7`
OCH3
58.4
59.0
Glu-1``
CH
104.1
105.5
2``
CH
74.7
76.1
3``
CH
78.1
78.4
2
4``
CH
71.6
71.6
5``
CH
79.5
78.5
6``
CH2OH
63.0
63.2
a
Usmanghani K, Rizwani G. 1988. New pregnane glycosides from Caralluma tuberculata. Journal
of natural products. 51: 1092-1097.
Figure S1: 13C-NMR (125 MHz) of compound 1
3
Figure S2: 1H of compound 2 in CDCl3 (600 MHz)
Figure S3: 13C of compound 2 in CDCl3 (150 MHz)
4
Figure S4: DEPT-135 of compound 2 in CDCl3
Figure S5: HSQC of compound 2 in CDCl3 (600 MHz)
5
Figure S6: COSY of compound 2 in CDCl3 (600 MHz)
Figure S7: HMBC of compound 2 in CDCl3 (600 MHz)
6
Figure S8: NOESY of compound 2 in CDCl3 (600 MHz)
Figure S9: TOCSY of compound 2 in CDCl3 (600 MHz)
7
Table S2: NMR (CDCl3) spectroscopic data of the acetate derivative 2 of compound 1
No.
1
δ13C (ppm)a
37.1, CH2
2
28.8, CH2
3
4
78.1, CH
34.4, CH2
5
6
44.1, CH
28.9, CH2
7
26.4, CH2
8
9
10
11
40.8, CH
48.9, CH
35.9, C
20.3, CH2
12
39.5, CH2
13
14
15
16
45.6, C
82.1, C
75.2, CH
31.4, CH2
17
18
19
51.2, CH
15.1, CH3
12.4, CH3
δ1H (ppm), J (Hz)
1a: 1.63, m
1b: 0.85, m
2a: 1.76, m
2b: 1.08, m
3.47, m
4a: 1.44, m
4b: 1.11, m
0.94, m
6a: 1.76, m
6b: 1.37, m
7a: 1.76, m
7b: 0.90, m
1.60, m
0.83, m
COSY
2
HMBC
NOESY
1, 3
2, 4
3, 5
11a: 1.37, m
11b: 1.66, m
12a: 1.37, m
12b: 1.21, m
5.24, t (8.42)
16a: 2.35, m
16b: 1.21, m
1.65, m
0.92, s
0.68, s
8
1`
5
4, 6
5, 7
19
7
6, 8
5
7, 9
8, 11
9, 14
19
9, 12
13
11
18
16a, 16b
17
b1, 17
20
16, 20
18, 21
14
1, 5, 9
15, 19
8, 16b
17
15, 18
16a
16b, 21
8
20
21
1`
2`
3`
4`
5`
6`
7`
1``
2``
3``
4``
5``
6``
73.4, CH
19.1, CH3
99.5, CH
71.4, CH
82.5, CH
74.2, CH
69.9, CH
16.8, CH3
58.3, OCH3
100.4, CH
71.2, CH
72.7, CH
68.8, CH
71.5, CH
61.9, CH2
a1
a2
b1
b2
c1
c2
d1
d2
e1
e2
f1
f2
g1
g2
169.4, C
20.9, CH3
170.0, C
20.5, CH3
169.9, C
20.6, CH3
170.6, C
21.6, CH3
170.4, C
20.6, CH3
170.4, C
20.6, CH3
169.5, C
21.6, CH3
4.98
1.07, d (5.90)
4.28, d (7.32)
4.86, dd (6.17, 4.90)
3.17, dd (9.85, 2.63)
3.82, br d (2.30)
3.43, dq (7.01, 6.70)
1.83, d (6.70)
3.33, s
4.80, d (8.42)
4.87, dd (5.63, 2.34)
5.19, t (9.58)
5.06
3.57, m
6``a: 4.18, dd (12.50, 2.96)
6``b: 4.05, dd (12.50, 4.60)
17, 21
20
2`
1`, 3`
2`, 4`
3`
6`
5`
2``
1``
2``, 4``
2``, 5``
6``b, 5``
6``a, 5``
a1
17, 20
3, 3`
1`, c1
5`
6`
1`, 3`
5`
3`
4`
1``, g1
f1
e1
d1
d1, 5``
1.98, s
20
1.94, s
15
1.99, s
2`
1.99, s
6``
1.95, s
4``
2.04, s
3``
1.93, s
2``
9
18