Identification of Pyrrolizidine Alkaloids in Senecio Plants by Liquid Chromatography-Mass Spectrometry

Table 1

Characterization of major compounds from five Senecio species.

No.	RT (min)	[M+H]^+	Compounds	Characteristic Fragment	Structure type	Main fragments
Characterized components
1	3.62	368	Retrorsine N-oxide	120, 138	RET, US	120, 138, 238, 296, 324, 340
2	3.88	370	Retronecine 9-(2,3-dihydroxy- 2-metrylbutanoate)7-senecioate N-oxide	120, 138	RET, US	120, 138, 280, 308, 326, 342
3	3.95	366	Seneciocannabine	120, 139	RET, US	120, 138, 214, 276, 294, 322
4	5.35	350	Jacozine	120, 138	RET, US	120, 138, 212, 242, 260, 278, 306, 322
5	5.62	366	Adonifoline	120, 138	RET, US	120, 138, 338
8	6.61	382	18-Hydroxysenkirkine	122, 150, 168	OTO	122, 150, 168, 186, 268, 364
9	6.84	352	Senecionine N-oxide	120, 138	RET, US	120, 138, 200, 234, 262, 280, 308, 324
10	6.96	354	Platyphylline N-oxide	122, 140	RET, S	122, 140, 158, 169, 282, 310
14	8.76	352	Oxyretroisosenine	120, 138	RET, US	120, 138, 324, 352, 360
15	9.19	356	Ipanguline 3″-Tigloyl	122, 140	RET, S	122, 140, 310, 328
20	9.92	352	Monocrotalinine	120, 138	RET, US	120, 138, 156, 278, 322
21	9.96	334	Seneciphylline	120, 138	RET, US	120, 138, 288, 306
24	11.30	412	Retronecine 9-(3-acetoxy-2-hydroxy-2-methylbutanoate)7-senecioate N-oxide	120, 138	RET, US	120, 138, 262, 308, 352, 368, 384
30	12.45	336	Senecionine	120, 138	RET, US	120, 138, 290, 308
31	12.49	356	7-Propionylintermedine	122, 140	RET, S	122, 140, 222, 240, 256, 312
32	12.84	338	Sarracine	122, 140	RET, S	122, 140, 292, 310, 320
33	13.26	352	Retrorsine	120, 138	RET, US	120, 138, 220, 246, 324
35	13.53	224	Isoretronecyl tiglate	124, 142	RET, S2	124, 142, 224
36	13.83	366	Senkirkine	122, 150, 168	OTO	122, 150, 168
37	13.98	288	Thesinine	124, 142	RET, S2	124, 142, 170, 188
39	15.04	336	Retroisosenine	120, 138	RET, US	120, 138, 220, 254
41	16.14	336	Doronenine	120, 138	RET, US	120, 138, 220, 238, 254
42	16.37	352	Jacobine	120, 138	RET, US	120, 138, 237, 254, 334
45	19.09	376	Seneciphyllinine	120, 138	RET, US	120, 138, 288, 316
46	20.97	322	Nilgirine	120, 138	RET, US	120, 138, 154, 218
47	21.82	338	Yamataimine	120, 138	RET, US	120, 138, 220, 238, 256
48	25.00	322	Diangeloylplatynecine	122, 140	RET, S	122, 140, 222, 240
49	25.00	336	Triangularine	120, 138	RET, US	120, 138, 218, 236, 254
50	25.77	338	Nemorensine	122, 140	RET, S	122, 140, 220, 238, 256
Tentatively characterized components
6	6.07	240	Fuchsisenecionine	122, 140	RET, S	122, 140, 158, 222
17	9.28
27	12.00
7	6.07	242	Planchonelline	124, 142	RET, S2	124, 142, 160
18	9.28
28	12.00
22	10.02	364	Dehydro-senkirkine	122, 150, 168	OTO	122, 150, 168, 318, 336, 346
25	11.85
13	8.38	238	7-Angeloylretronecine	120, 138	RET, US	94, 120, 138, 156
16	9.21
11	7.46	388	Jaconine or merenskine	120, 138	RET, US	120, 138, 324, 352, 360
12	7.76	336	Unknown	122, 140	RET, S	122, 140, 167, 222, 265
19	9.57	382	Otonecine or senecioracenine or petasitenine	122, 150, 168	OTO	122, 150, 168, 200, 240, 310, 338, 354
23	10.35	350	Seneciphylline N-oxide	120, 138	RET, US	120, 138, 246, 288, 322, 332
26	11.99	434	Unknow (new in nature product)	124, 142	RET, S2	124, 142, 288
34	13.45
29	12.41	340	Unknown (dihydro-sarracine)	122, 140	RET, S	122, 140, 294, 312
43	16.41	340	Unknown	122, 140	RET, S	122, 140, 155, 322, 338
38	14.57	338	Bulgarsenine	122, 140	RET, S
			Hastacine
			Platyphylline

RET: retronecine type; OTO: otonecine type; S: saturated type; S2: saturated type II and US: unsaturated type.