Chemical and genomic diversity of six Lonicera species occurring in Korea Author Kang, Kyo Bin College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, 08826, Republic of Korea & Department of Plant Science, Plant Genomics and Breeding Institute, Research Institute of Agriculture and Life Sciences, College of Agriculture and Life Sciences, Seoul National University, Seoul, 08826, Republic of Korea Author Kang, Shin-Jae Department of Plant Science, Plant Genomics and Breeding Institute, Research Institute of Agriculture and Life Sciences, College of Agriculture and Life Sciences, Seoul National University, Seoul, 08826, Republic of Korea Author Kim, Mi Song College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, 08826, Republic of Korea Author Lee, Dong Young Author Han, Sang Il Medicinal Plant Garden, College of Pharmacy, Seoul National University, Koyang, 12045, Republic of Korea & College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, 08826, Republic of Korea & Department of Plant Science, Plant Genomics and Breeding Institute, Research Institute of Agriculture and Life Sciences, College of Agriculture and Life Sciences, Seoul National University, Seoul, 08826, Republic of Korea Author Kim, Tae Bum Author Park, Jee Young Department of Plant Science, Plant Genomics and Breeding Institute, Research Institute of Agriculture and Life Sciences, College of Agriculture and Life Sciences, Seoul National University, Seoul, 08826, Republic of Korea Author Kim, Jinwoong Author Yang, Tae-Jin Author Sung, Sang Hyun text Phytochemistry 2018 2018-08-16 155 126 135 http://dx.doi.org/10.1016/j.phytochem.2018.07.012 journal article 285218 10.1016/j.phytochem.2018.07.012 7f7aa78f-bf61-4e55-af34-c1c79021655a 1873-3700 10484355

Table 3 Characterization of metabolites in Lonicera plant extracts by LC–MS.

No.	Identity	Classification	tR (min)	Observed MS	Calculated MS	Molecular	Fragments
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a Confirmed by comparison with previously isolated compounds.
				[M− H] −	[M− H] −	formula
1	loganic acid a	Iridoid	3.71	375.1286	375.1291	C 16H24 O 10	213 [M− Glc− H O− H] − 2
							169 [M− Glc− COOH− H] −
							151 [M− Glc− COOH− H O− H] − 2
2	quinic acid	organic acid	4.07	191.0554	191.0556	C 7 H 12 O 6	–
3	7-desmethylsecologanol	Iridoid	4.38	375.1270	375.1291	C 16 H 24 O 10	309, 265, 195, 151
4	unknown	unknown	4.53	469.1454	469.1499	C 25 H 26 O 9	237, 193
5	secologanic acid a	Iridoid	5.07	373.1127	373.1135	C 16H22 O 10	193 [M− Glc− H O− H] − 2
6	unknown	unknown	5.17	369.0806	369.0822	C 16 H 18 O 10	207, 192
7	unknown	unknown	5.33	507.1717	507.1714	C 21 H 32 O 14	–
8	loganin a	Iridoid	6.19	389.0858	389.0873	C 19H18 O 9	227 [M− Glc− H] −
9	sweroside a	Iridoid	6.26	357.1182	357.1186	C 16H22 O 9	195 [M− Glc− H] −
							125 [(RDA product)−H] −
10	unknown	unknown	6.54	519.2454	519.2442	C 24 H 40 O 12	441, 207
11	6′- O -apiosylsweroside	Iridoid	6.68	489.1610	489.1608	C 21H30 O 13	195 [M− Api− Glc− H] −
							125 [(RDA product)−H] −
12	luteolin 7- O -(6- O -glucosylglucoside)	flavonoid	6.97	609.1474	609.1456	C 27H30 O 16	447 [M− Glc− H] −
							285 [M−2Glc− H] −
13	unknown	Iridoid	7.18	419.1531	419.1553	C 18 H 28 O 11	–
14	secologanol a	Iridoid	7.36	389.1467	389.1448	C 17H26 O 10	–
15	secologanin a	Iridoid	7.41	387.1288	387.1291	C 17H24 O 10	225 [M− Glc− H] −
							155 [(RDA product)−H] −
16	unknown	phenyl propanoid	7.45	503.1772	503.1765	C 22 H 32 O 13	287, 155
17	Kingiside	iridoid	7.55	403.1245	403.1240	C 17 H 24 O 11	–
18	unknown	Iridoid	7.77	387.1277	387.1267	C 17 H 24 O 10	255, 155
19	unknown	unknown	8.67	579.2056	579.2078	C 28 H 36 O 13	417, 181
20	7-desoxyloganic acid a	iridoid	8.69	359.1333	359.1342	C 16H24 O 9	197 [M− Glc− H] −
21	luteolin 7- O -(6- O -	flavonoid	8.96	579.1351	579.1350	C 26H28 O 15	447 [M− Ara− H] –
	arabinosylglucoside)						285 [M− Ara− Glc− H] –
22	miscanthoside	flavonoid	9.33	449.1084	449.1084	C 21H22 O 11	287 [M− Glc− H] –
							151 (1,3 A – of aglycone)
							135 (1,3 B − of aglycone)
23	luteolin-7- O -glucoside	flavonoid	9.69	447.0916	447.0927	C 21H20 O 11	285 [M− Glc− H] −
24	lonicerin	flavonoid	10.11	593.1511	593.1506	C 27H30 O 15	447 [M− Rha− H] −
							285 [M− Rha− Glc− H] −
25	unknown	unknown	10.43	743.2420	743.2399	C 33 H 44 O 19	–
26	3,5-di- O -caffeoylquinic acid	organic acid	10.65	515.1194	515.1190	C 25H24 O 12	375 [M−(caffeoyl)+HCOOH− H] −
							353 [M−(caffeoyl)−H] −
							335 [M−(caffeoyl)−H O− H] − 2
							191 [M−2(caffeoyl)−H] −
							179 [(caffeic acid) − −H]
							135 [(caffeic acid)−CO] − 2
27	3,4-di- O -caffeoylquinic acid	organic acid	10.88	515.1188	515.1190	C 25 H 24 O 12	(similar to 26)
28	luteolin-4′- O -glucoside	flavonoid	11.54	447.0921	447.0927	C 21H20 O 11	285 [M− Glc− H] −
29	apigenin 7- O -glucoside	flavonoid	11.59	431.0981	431.0978	C 21H20 O 10	268 [M− Glc− H] −
30	apigenin 7- O -(2- O -	flavonoid	11.75	577.1551	577.1557	C 27H30 O 14	413 [M− Glc− H] −,
	glucosylrhamnoside)						269 [M− Glc− Rha− H] −
31	4,5-di- O -caffeoylquinic acid	organic acid	12.17	515.1197	515.1190	C 25 H 24 O 12	(similar to 26)
32	unknown	unknown	12.48	505.2647	505.2649	C 24 H 42 O 11	373, 161
33	(E)-aldosecologanin a	iridoid	12.66	757.2552	757.2555	C 34H46 O 19	595 [M− Glc− H] −
							525 [(RDA Product)−H] −
34	grandifloroside	iridoid	12.94	537.1614	537.1614	C 25H30 O 13	375 [M−(caffeoyl)−H] −
							179 [(caffeic acid)−H] −
35	hesperetin	flavonoid	13.05	301.0711	301.0712	C 16 H 14 O 6	–
36	(Z)-alcosecologanin	iridoid	13.66	757.2563	757.2555	C 34 H 46 O 19	(similar to 33)
37	periclymenoside a	iridoid	14.00	727.2451	727.2449	C 33H44 O 18	565 [M− Glc− H] −
							403 [M−2Glc− H] −
							193 [(ferulic acid)−H] −
38	unknown	unknown	14.32	733.2334	733.2344	C 35 H 42 O 17	537, 357, 177
39	3- O -caffeoylquinic acid	organic acid	14.51	353.0871	353.0873	C 16H18 O 9	191 [M−(caffeoyl)−H] −
							179 [(caffeic acid)−H] −
40	7- O -(Z)-feruloylloganic acid	iridoid	14.88	551.1734	551.1765	C 26H32 O 13	389 [M− Glc− H] −
							193 [(ferulic acid)−H] −
41	7- O -(E)-feruloylloganic acid	iridoid	15.01	551.1734	551.1765	C 26 H 32 O 13	(similar to 40)
42	luteolin	flavonoid	15.32	285.0403	285.0399	C 15 H 10 O 6	–
43	unknown	unknown	15.53	705.2971	705.2970	C 32 H 50 O 17	347
44	unknown	unknown	15.63	799.4874	799.4844	C 42 H 72 O 14	–
45	lonitoside	terpenoid	16.11	461.1998	461.2023	C 21 H 34 O 11	347
46	unknown	unknown	16.93	703.2240	703.2238	C 34 H 40 O 16	345, 327, 315
47	unknown	unknown	17.09	539.1765	539.1765	C 25 H 32 O 13	359, 167
48	kinginoside a	iridoid	17.39	679.2232	679.2238	C 32H40 O 16	537, 483, 441, 381, 339
							193 [(ferulic acid)−H] −
				[M− H] −	[M− H] −	formula
49	methylgrandifloroside methyl ester	iridoid	17.95	565.1916	565.1921	C27H34O13	403 [M− Glc− H] −
							371 [M−(feruloyl)−H] −
							193 [(ferulic acid)−H] −
50	onjixanthone I	xanthone	18.22	301.0710	301.0712	C16H14O6	–
51	unknown	biflavonoid	18.39	537.0839	537.0822	C30H18O10	417, 375
52	unknown	fatty acid	18.83	329.2325	329.2328	C18H34O5	–
53	unknown	biflavonoid	18.86	537.0836	537.0822	C30H18O10	417, 375