Spirostane saponins with a rearranged A / B ring system isolated from the rhizomes of Ophiopogon japonicus Author Liu, Bo , Bingxin Li &, Gang Chen &, Yingni Pan &, Di Zhou & **, Ning Li & * & School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Wenhua Road 103, Shenyang, 110016, China Author Li, Bingxin Author Chen, Gang Author Pan, Yingni Author Zhou, Di Author Li, Ning text Phytochemistry 2022 112975 2022-01-31 193 1 9 http://dx.doi.org/10.1016/j.phytochem.2021.112975 journal article 10.1016/j.phytochem.2021.112975 1873-3700 8194415

Table 2 1 H NMR and 13 C NMR Data of Compounds 3 and 4 (Pyridine- d, δ in ppm). 5

Position	3 b		4 a
a Measured at 400 MHz for 1 H NMR, 100 MHz for 13 C NMR. b Measured at 600 MHz for 1 H NMR, 150 MHz for 13 C NMR. c Signals overlapped.
	δH	δC, type	δH	δC, type
1	1.82 c, 1.17 c	38.3,	1.86 c, 1.04 c	36.6,
		CH2		CH2
2	2.06 c, 1.78 c	33.1,	1.89 c	31.9,
		CH2		CH2
3	3.83 m	71.6, CH	3.87 m	71.6, CH
4	2.65 c	44.0,	2.27 c, 1.79 c	37.9,
		CH2		CH2
5	–	141.4, C	1.40 c	43.1, CH
6	5.49 brs	122.4,	1.93 c, 1.32 c	28.1,
		CH		CH2
7	2.71 c, 1.88 c	26.4,	1.39 c	22.6,
		CH2		CH2
8	2.16 td (10.6, 5.7)	36.6, CH	2.01 c	40.2, CH
9	2.07 c	39.9, CH	2.57 td (11.2, 4.7)	33.8, CH
10	–	37.4, C	–	35.7, C
11	1.58 c	29.2,	1.49 c, 1.40 c	20.8,
		CH2		CH2
12	4.49 c	76.9, CH	2.27 c, 1.49 c	33.0,
				CH2
13	–	49.0, C	–	45.7, C
14	–	88.8, C	–	87.5, C
15	2.47 dd (12.5, 7.8),	40.5,	2.37 dd (12.7, 7.5),	40.4,
	1.72 c	CH2	1.88 c	CH2
16	4.99 c	91.6, CH	5.1 dt (6.7, 7.5)	82.4, CH
17	–	94.8, C	2.83 t (6.9)	60.3, CH
18	0.99 s	22.2,	1.10 s	20.8, C
		CH3
19	1.10 s	20.0,	1.02 s	23.9, C
		CH3
20	2.39 q (7.1)	46.9, CH	2.11 m	42.4, CH
21	1.30 d (7.0)	10.0,	1.20 d (7.0)	15.7,
		CH3		CH3
22	–	110.1, C	–	109.9, C
23	1.75 c, 1.67 c	32.3,	1.73 c	32.4,
		CH2		CH2
24	1.93 c	29.7,	1.59 c	29.7,
		CH2		CH2
25	1.58 c	30.8, CH	1.60 c	31.0, CH
26	3.48 c 3.44 c	67.2,	3.57 c, 3.51 c	67.2,
		CH2		CH2
27	0.66 d (5.5)	17.7,	0.69 d (5.4)	17.7,
		CH3		CH3
12-OH	7.05 brs
14-OH	5.85 brs
17-OH	6.57 brs