. Author manuscript; available in PMC: 2013 Jul 18.

Published in final edited form as: J Nat Prod. 2009 Jan;72(1):92–98. doi: 10.1021/np800653z

Table 1.

¹H and ¹³C NMR Data^† (J values in Hz, in parenthesis) for 1, 2 and 5

H/C	Prosopilosidine (1)		Prosopilosine (2)		Juliprosopine (5)⁺

	δ_H	δ_C	δ_H	δ_C	δ_H	δ_C
2, 2′	3.19 dq (6)	51.5 d	3.13 q (7.8)	50.5 d	2.75 q (6.5)	57.2 d
3, 3′	3.75 ddd (4.8)	68.4 d	3.66 br s	68.9 d	3.48 br.s	67.8 d
4, 4′	1.70 m	26.7 t	1.72 m	27.9 t	1.84 m	26.1 t
4, 4′	1.59 m	26.7 t	1.62 m	27.9 t	1.46 m	26.1 t
5, 5′	1.82 m	28.2 t	1.49 m	26.9 t	1.40 m	25.8 t
5, 5′	1.21 m	28.2 t	1.22 m	26.9 t	1.20 m^*	25.8 t
6, 6′	2.80 m^*	49.0 d	2.85 m	50.1 d	2.56 q (8)	55.8 d
7, 7′	1.14 d (7)	11.9 q	1.12 d (6.5)	15.3 q	1.07 d (6.4)	18.4 q
1″, 1‴	1.37 m	29.3 t	1.40 m	28.3 t	1.40–1.20 m^*	37.0 t
2″, 2‴		30.7, 29.8,		27.0 t		32.2 t
3″-8″	1.35–1.27 m^*	29.6, 29.5,	1.39–1.27 m^*	30.5, 30.1,	1.30–1.20 m^*	29.3, 29.5,
3″-8″		29.4, 29.2,	1.39–1.27 m^*	30.0, 29.8,		29.6, 29.8,
3‴-8‴		29.1, 29.0,		29.8, 29.7^*		30.1 (5 × t)
9″, 9‴		26.3 (9 × t)	1.43 m	(6 × t)		26.6 t
10″	2.80 m^*	32.1 t	2.00 t (7.5)	35.4 t	2.00 t (7.4)	35.1 t
10‴	2.80 m^*	31.7 t	1.39–1.27 m^*	29.8^*	1.40–1.20 m^*	28.0 t
1″″	2.80 m^*	31.6 t	1.52 m	33.4 t	1.40–1.20 m^*	33.1 t
2″″	2.50 m	20.9 t	2.05 m	21.8 t	2.04 m	21.5 t
2″″	2.50 m	20.9 t	1.80 m	21.8 t	1.76 m	21.5 t
3″″	4.88 m^*	59.4 t	3.13 dd (18, 7.8)	54.7 t	3.11 ddd (17.6, 7.8)	54.5 t
3″″	4.88 m^*	59.4 t	2.10 dd (18, 9)	54.7 t	2.08 dd (17.6, 9)	54.5 t
5″″	8.64 s	137.3 d	3.29 d (15)	55.5 t	3.26 d (15.2)	55.3 t
5″″	8.64 s	137.3 d	2.64 d (15)	55.5 t	2.58 d (15.2)	55.3 t
6″″	-	139.1 s	-	136.1 s	-	136.3 s
7″″	8.18 s	144.3 d	5.37 s	123.8 d	5.33 s	123.9 d
8″″	-	141.3 s	2.00 m	42.8 d	2.00 m	42.6 d
8a″″	-	155.0 s	1.82 m	65.8 d	1.74 m	65.6 d

^†

All spectra recorded in CD₃OD at 500 MHz (¹H) and 125 MHz (¹³C).

Overlapped signals.

⁺

Data recorded during this investigation and the literature data^5,6 was in agreement with recorded values.