Phenolic Profile of Dark-Grown and Photoperiod-Exposed Hypericum perforatum L. Hairy Root Cultures

Table 2

Retention times, UV, and mass spectral data of xanthones in Hypericum perforatum dark-grown (HR1) and photoperiod-exposed (HR2) hairy root culture extracts^a.

Peak; no.	Compounds	𝑡𝑅 (min)	UV (nm)	[M–H]^--; (𝑚/𝑧)	–MS^2  [M–H]^--; (𝑚/𝑧)	HR1 (mg⋅100 g^−1 DW ± S.D.)	HR2 (mg⋅100 g^−1 DW ± S.D.)
X1	Mangiferin	37.3	238, 256, 312, 362	421	331, 301, 258	1383.25±88.91	669.67±24.12
X2	Xanthone derivative 1	45.8	208, 257, 322, 374	441	423, 397, 373, 305, 257, 229	109.47±9.81	n.d.
X3	Xanthone derivative 2	46.2	242, 306	367	287	635.06±18.52	600.59±39.62
X4	1,3,5,6-Tetrahydroxyxanthone dimer	50.2	252, 284, 328	517	499, 468, 446, 391, 365	821.61±28.39	692.94±19.28
X5	1,3,6,7-Tetrahydroxyxanthone dimer	53.9	238, 254, 312, 364	517	517, 469, 447, 379, 257	522.56±25.44	88.31±2.88
X6	1,3,5,6-Tetrahydroxyxanthone	55.4	250, 282, 328	259	229, 213, 187	190.17±20.73	949.35±51.71
X7	1,3,6,7-Tetrahydroxyxanthone	55.8	236, 254, 314, 364	259	231, 215, 187, 147	167.14±9.52	874.85±31.24
X8	Tetrahydroxy-one-methoxyxanthone	57.7	254, 286, 328	289	274, 175	n.d.	448.65±9.44
X9	Xanthone derivative 3	59.2	244, 280, 316	353	273	n.d.	276.57±9.29
X10	1,3,5-Trihydroxy-6-methoxyxanthone	63.3	250, 284, 326	273	258,225	n.d.	150.86±12.62
X11	Mangiferin C-prenyl isomer	73.5	238, 260, 312, 372	489	399, 369, 327	433.68±82.56	n.d.
X12	1,3,6,7-Tetrahydroxyxanthone 8-prenylxanthone	73.9	248, 312, 366	327	325, 297, 258, 201	547.65±15.21	737.48±65.39
X13	1,3,5,6-Tetrahydroxyxanthone 8-prenylxanthone	74.9	242, 260, 320, 368	327	325, 297, 258, 201	368.17±21.70	n.d.
X14	1,3,7-Trihydroxy-2-(2-hydroxy-3-methyl-3-butenyl)xanthone	75.3	238, 260, 314, 388	327	309, 257	588.66±49.31	854.53±31.88
X15	Toxyloxanthone	76.2	242, 262, 330, 384	325	307, 283, 272	577.03±5.09	1542.09±129.21
X16	1,3,7-Trihydroxy-6-methoxy-8-prenylxanthone	76.5	240, 260, 318, 370	341	326, 311, 297, 285	650.13±34.77	n.d.
X17	1,3,6,7-Tetrahydroxyxanthone 2-prenylxanthone	76.7	248, 312, 368	327	325, 283, 271	1402.03±85.98	656.33±37.25
X18	γ-Mangostin isomer	77.1	254, 286, 324	395	326, 283, 271	1226.31±185.52	1480.32±130.06
X19	1,3,6-Trihydroxy-7-methoxy-8-prenylxanthone	77.2	240, 256, 312, 370	341	293, 256	3240.28±140.14	n.d.
X20	1,3,5,6-Tetrahydroxyxanthone 2-prenylxanthone	77.4	238, 260, 318, 372	327	297, 258	n.d.	699.36±49.61
X21	Paxanthone	78.0	244, 264, 324, 386	339	324, 307	n.d.	4040.70±209.82
X22	γ-Mangostin isomer	78.9	260, 316, 370	395	351, 339, 326, 283	3629.15±338.08	n.d.
X23	Trihydroxy-1-methoxy-C-prenylxanthone	79.4	260, 286, 314	341	326	11314.34±469.01	10067.14±561.72
X24	Xanthone derivative 4	79.9	260, 308, 374	295	277, 251, 195, 171	n.d.	2778.02±81.11
X25	γ-Mangostin	80.0	246, 262, 320	395	351, 339, 326, 283	7861.71±415.11	n.d.
X26	Banaxanthone D	80.2	244, 268, 332	461	393, 341, 297	1784.69±88.90	n.d.
X27	Xanthone derivative 5	80.5	254, 310	355	340, 325, 297, 285, 271	2266.19±191.89	1765.42±36.19
X28	Garcinone E	81.2	256, 286, 332	463	394, 351, 339, 297, 285	8229.95±537.14	10844.13±288.29
X29	Xanthone derivative 6	82.2	262, 288, 322	393	/	421.44±36.66	370.43±45.16
X30	Banaxanthone E	82.6	252, 302, 330	477	419, 393, 339, 297	n.d.	499.91±38.44
X31	Xanthone derivative 7	83.6	270, 330, 400	467	398, 383, 327, 271, 234	n.d.	429.57±7.82
X32	Garcinone C	83.9	286, 340	413	369, 344, 301, 233	1185.94±149.05	943.63±55.98
X33	Xanthone derivative 8	84.4	254, 284, 326	481	412, 397, 327, 271, 234	562±38.99	126.80±1.69

an.d.: not detected; DW: dry weight; sh: shoulder; 𝑡_𝑅: retention time. MS² ions in bold indicate the base peak. For information on peak numbers, see Figure 1.