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. 2016 May 18;21(5):592. doi: 10.3390/molecules21050592

Table 2.

Identified compounds in extract of HGKYC and in rat serum after oral administration of HGKYC in positive and negative ion mode.

No. TR (min) Formula [M + H]+ (Error, ppm) [M − H] (Error, ppm) Fragment Ions in Identified Compounds Ref.
Positive (+) Ion Mode Negative (−) Ion Mode In Extract In Serum
1 0.77 C6H14N4O2 173.1046 (1.2) 131.0829 Arginine s [10]
2 0.78 C5H13NO 104.1070 (0.7) 60.0832 [M + H − H − C2H5O]+ Choline s + [10]
58.0680
3 0.85 C5H9NO2 116.0705 (−0.7) 70.0671 [M + H − HCOOH]+ Proline [11]
4 0.9 C5H11NO2 118.0861 (−0.7) 116.0721 (3.5) 72.0818 [M + H − HCOOH]+ Betaine s + [10]
58.0676, 55.0566
5 1.07 C5H5N5 136.0717 (−0.2) 119.0353 [M + H − H − NH3]+ Adenine s [10]
92.0251 [M + H − H − NH3 − HCNN]+
6 1.08 C6H5NO2 124.0392 (−0.5) 106.0278 [M + H − H2O]+ Nicotinic acid s
79.0425, 78.0348
7 1.08 C5H7NO3 130.0499 (−0.6) 84.0461 [M + H − HCOOH]+ l-Pyroglutamic acid s + [10]
56.0530 [M + H − H − NH3 − HCNOOH]+ +
8 1.13 C9H11NO3 182.0806 (−3.3) 165.0547 [M + H − H − NH3]+ Tyrosine s + [10]
136.0761 [M + H − HCOOH]+
119.0487 [M + H − HCOOH − H2O]+
91.0548
9 1.17 C6H13NO2 132.1018 (−1.1) 86.0964 [M + H − HCOOH]+, Isoleucine s + [10]
69.0711 [M + H − HCOOH − NH3]+
10 1.21 C9H8O3 165.0546 (0.02) 123.0448 [M + H − H − C2H2O]+ p-Coumaric acid s + [10]
95.0500 [M + H − H − C2H2O − CO]+
77.0397 [M + H − H − C2H2O − CO − H2O]+
65.0414
11 1.73 C7H6O5 171.0285 (−1.7) 169.0143 (0.4) 153.0180 [M + H − H2O]+ 125.0253 [M − H − CO2] Gallic acid s [10]
107.0131 [M + H − H2O − HCOOH]+ 79.0217 [M − H − CO2 − HCOOH]
12 2.04 C9H11NO2 164.0716 (−0.9) 147.0438 [M − H − NH3] Phenylalanine s + [10]
103.0560 [M − H − NH3 − CO2]
13 2.54 C8H8O4 167.0350 (0.2) 123.0449 [M − H − CO2]− Vanillic acid [12]
93.0358 [M − H − CO2 − OCH3]
97.0283, 69.0341, 65.0399
14 2.92 C7H6O4 153.01989 (3.6) 109.0309 [M − H − CO2] Protocatechuic acid [13]
91.0208 [M − H − CO2 − H2O]
15 3 C5H7NOS 130.0316 (−3.9) 128.0442 (1.0) 103.0536 [M + H − HCN]+ Epigoitrin s [14]
84.0819 [M + H − HCOOH]+
70.0657, 60.9750
16 3.08 C11H12N2O2 203.0825 (−0.4) 142.0664 [M − H − NH3 − CO2] Tryptophan s + [10]
116.0513 [M − H − NH3 − 2OCH2]
17 3.83 C7H6O3 137.0248(2.8) 119.0145 [M − H− H2O] Protocatechuic aldehyde s [13]
108.0288 [M − H − CO]
92.0284
18 3.87 C14H20O7 299.1140 (1.3) 137.0244 [M − H − Glc] Salidroside s [15]
119.0335 [M − H − Glc − H2O]
93.0357, 59.0172
19 4.31 C8H8O5 183.0300 (0.7) 168.0065 [M − H − CH3] Methyl gallate s + [13]
124.0175, 78.0136
20 4.49 C15H18O9 341.0881 (0.8) 179.0352 [M − H − Glc] Caffeoylglucose + [13]
135.0454 [M − H − Glc − CO2]
21 4.49 C15H14O6 291.0860 (−0.9) 207.0643, 147.0439 Catechin s [13]
139.0392, 123.0440
22 4.55 C16H18O9 355.1023 (−0.1) 353.0878 (3.0) 163.0386 [M + H − H − Glc − OCH2]+ 191.0564 [M − H − Glc] Chlorogenic acid s [16]
145.0280, 117.0329
23 4.77 C17H24O9 373.1487 (−1.6) Syringoside s [17]
24 4.96 C9H8O4 179.035 4 (2.3) 135.0459 [M − H − CO2] Caffeic acid s + [13]
25 5.15 C11H10O5 223.0595 (−2.5) 221.0456 (0) 162.0302 [M + H − H − CH3 − HCOOH]+ 206.0213 [M − H − CH3] Isofraxidin s [16]
190.9989 [M − H − OCH3]
177.0184 [M − H − CO2]
163.0003 [M − H − OCH2 − CO]
26 5.36 C20H23O4N 342.1695 (−1.3) 340.1557 (0.8) 297.1110 [M + H − HCN − H2O]+ 310.1088 [M − H − OCH2] Magnoline [14]
282.0881 [M + H − HCN − H2O − CH3]+ 252.0404 [M − H − CO2 − NH3 − HCNN]
237.0902, 191.0848, 58.0680 224.0509 [M − H − CO2 − NH3 − HCNN − H2O]
162.0180, 118.0288,79.9591
27 5.51 C19H18O11 423.0925 (0.7) 421.0780 (0.8) 405.0776 [M + H − H2O]+ 331.0459 [M − H − HCOOH − CO2] Mangiferin [18]
339.0520, 327.0493, 303.0478 271.0253 [M − H − Xyl]
285.0417 259.0230 [M − H − Glc]
273.0395,
28 5.54 C17H20N4O6 377.1450 (−1.6) 359.1339, 243.0878, 198.0644 Riboflavin [19]
29 5.97 C17H20O9 367.1038 (0.9) 191.0561 3-Feruloyquinic acid [13]
30 6.07 C23H28O11 479.1569 (2) 449.1433, 327.1081 Paeoniflorin s [20]
255.0647, 165.0568, 121.0297
31 6.08 C9H10O5 197.0458 (1.4) 169.0147, 124.0175, 78.0178 Syringic acid s +
32 6.2 C9H8O3 163.0400 (−0.4) 119.0505 [M − H − CO2] trans-p-Coumaric acid s +
93.0352 [M − H − CO − C2H2O]
33 6.48 C34H46O18 743.2744 (−1.8) 741.2628 (2.2) 579.2111 [M − H − Glc] Eleutheroside E s [13]
417.1579 [M − H − 2Glc]
34 6.48 C28H36O13 579.2100 (2.9) Eleutheroside E1 [13]
35 6.82 C10H10O4 193.0508 (0.8) 178.0263 [M − H − CH3] Ferulic acid s [13]
134.0375 [M − H − CH3 − CO2]
36 6.9 C20H22O8 391.1372 (−3.9) 389.1252 (2.7) 229.0859 [M + H − H − Glc]+ 227.0718 [M − H − Glc] Polydatin s + [21]
185.0612 [M − H − Glc − C2H2O]
37 6.91 C14H12O3 229.0850 (3.9) 227.0715 (0.7) 183.0788 185.0601, 143.0508 Resveratrol s + [22]
165.0690 [M + H − H2O − HCOOH]+
107.0489, 91.0540
38 6.95 C26H28O13 547.1479 (4) 6-C-Arabinosyl-8-C-Glucosyl-Chrysin + [23]
487.1279
457.1169 [M − H − C3H6O − OCH2]
427.1052
409.0946, 367.0839
337.0734 [M − H − Glc − OCH2]
39 7.04 C27H30O16 611.1584 (−3.6) 609.1482 (3.8) 465.1016 [M + H − H − Rha]+ 301.0354 [M − H − Rha − Glc] Rutin s [18]
303.0501 [M + H − H − Rha − Glc]+ 271.0228
40 7.10 C21H18O12 461.0736 (2.2) 285.0416 [M − H − Glc acid] Scutellarin s + [18]
41 7.19 C21H20O12 463.0891 (1.9) 301.0360 [M − H − Glc] Hyperoside s + [24]
271.0250 [M − H − Glc − OCH2]
255.0310 [M − H − O − Glc − OCH2]
178.9998, 151.0041
42 7.21 C23H24O13 509.1271 (−3.6) 507.1156 (2.3) 347.0750 [M + H − H − Glc]+, 345.0632 [M − H − Glc] Viscidulin III- [25]
332.0523 [M + H − H − Glc − CH3]+ 330.0383 [M − H − Glc − CH3] Glucopyranoside
314.0409 315.0174 [M − H − Glc − 2CH3]
43 7.32 C26H28O13 547.1479 (4.0) 487.1279 6-C-Glucosyl-8-C-Arabinosyl-Chrysin [23]
457.1169 [M − H − C3H6O − OCH2]
427.1052
409.0946, 367.0839
337.0734 [M − H − Glc − OCH2]
44 7.41 C21H20O13 479.0831 (0.1) 441.0761, 435.0957 Isomyricitrin [26]
313.0570, 165.0548
45 7.59 C25H24O12 517.1326 (−2.8) 515.1199 (0.7) 499.1177 [M + H − H2O]+ 353.0889 Cynarin [13]
163.0382 191.0562
179.0347
46 7.63 C33H40O18 723.2144 (0.2) Ligustroflavone s [27]
47 7.63 C31H42O17 687.24992 (0.6) 685.2372 (3.4) 523.1831 [M − H − Glc] Specnuezhenide [15]
454.1404, 421.1508
299.1137, 223.0603
48 7.74 C20H18O11 435.0913 (−2) 433.0784 (1.7) 303.0493 [M + H − H−Arab]+ 301.0294 [M − H − Arab] Quercetin-3-arabinoside [23]
271.0257 [M − H − Arab − OCH2]
255.0314, 178.9989, 151.0036
49 7.93 C21H20O9 417.1169 (−2.6) 415.1044 (2.2) 399.1071 [M + H − H2O]+ 325.0692 [M − H − C3H6O3] Chrysin-8-C-glucoside + [23]
297.0758 [M + H − H − C4H8O4]+ 295.0624 [M − H − C4H8O4]
279.0639 [M + H − H − C4H8O4−H2O]+ 267.0676 [M − H − C4H8O4 − CO]
267.0644 [M + H − H − C4H8O4 − 2H2O]+ 149.0237
50 7.97 C21H20O11 449.1063 (−3.3) 447.0947 (3.1) 303.0488 [M + H − H − Rha]+ 301.0379 [M − H − Rha] Quercetrin s [18]
287.0549 [M + H − H − O − Rha]+ 271.0265 [M − H − Rha − OCH2]
129.0543, 85.0289 255.0315, 178.9983
85.0286 151.0041
51 8.22 C32H38O16 679.2215 (−2.6) 533.1669 [M + H − H − Rha]+ hexandraside E [14]
371.1096 [M + H − H − Rha − Glc]+
315.0457 [M + H − H − Rha − Glc − C4H8]+
52 8.52 C38H48O20 825.2794 (−2.1) 663.2238 [M + H − H − Glc]+ Diphylloside B [14]
517.1674 [M + H − H − Rha − Glc]+
355.1199 [M + H − H − Rha−2Glc]+
299.0562 [M + H − H − Rha−2Glc − C4H8]+
53 8.53 C26H28O11 517.1693 (−2.2) 355.1169 [M + H − H − Glc]+ Icarrin C [14]
299.0524 [M + H − H—Glc − C4H8]+
54 8.58 C21H18O11 447.0912 (−2.2) 445.07858 (2.1) 271.0595 [M + H − H − O − Glc]+ 269.0459 [M − H − O − Glc] Baicalin s + [23]
55 8.82 C38H48O19 809.28357 (−3.3) 807.2011 (0.33) 663.2266 [M + H − H − Xyl]+ Epimedin B [14]
517.1687 [M + H − H − Xyl − Rha]+
355.1182 [M + H − H − Xyl − Rha − Glc]+
299.0542 [M + H − H − Xyl − Rha − Glc − C4H8]+
56 8.86 C22H22O9 431.1318 (−4.2) 429.1101 (0.3) 269.0802 [M + H − H − Glc]+ Ononin
57 8.87 C21H22O9 417.1191 (0) 255.0678 [M − H − Glc] Polygonimitin B [18]
211.0773 [M − H − Glc − CO2]
58 8.89 C21H20O11 449.1063 (−3.3) 447.0946 (3.1) 303.0488 [M + H − H − Rha]+ 301.0379 [M − H − Rha]− Isoquercetrin
287.0549 [M + H − H − O − Rha]+ 271.0265 [M − H − Rha − CH2]
129.0543,85.0289 255.0315,178.9983
59 8.9 C32H38O15 663.2265 (−2.7) 661.2169 (4.7) 517.1667 [M + H − H − Rha]+ 515.1907 Epimedoside A
355.1180 [M + H − H − Rha − Glc]+ 353.1050
299.0559 [M + H − H − Rha − Glc − C4H8]+
60 9.0 C17H14O8 347.0751 (−3.1) 332.0523, 317.0288, 314.0414 Viscidulin III [23]
289.0340, 169.0125
61 9.04 C39H50O20 839.2967 (−0.2) 677.2346 [M + H − H − Glc]+ Epimedin A
531.1881 [M + H − H − Glc − Rha]+
369.1342 [M + H − H − 2Glc − Rha]+
313.0691 [M + H − H − 2Glc − Rha − C4H8]+
62 9.15 C33H40O16 693.2365 (−3.4) 547.1791 [M + H − H − Rha]+ anhydroicaritin [14]
531.1895 [M + H − H − Glc]+ -3,7-di-O-glucoside
385.1284 [M + H − H− Rha − Glc]+
369.1321 [M + H − H − O − Rha − Glc]+
313.0687 [M + H − H − O − Rha − Glc − C4H8]+
63 9.15 C30H32O13 599.1787 (2.8) 581.1699 [M − H − H2O] Benzoyloxypaeoniflorin [20]
477.1593 [M − H − C7H6O2]
449.7983 [M − H − C7H6O2 − CO]
431.1372 [M − H − H2O − Xyl]
281.0676 [M − H − H2O − Xyl − C5H10O5]
64 9.45 C22H22O10 447.1269 (−3.8) 445.1143 (0.6) 285.0757 [M + H − H − Glc]+, 430.0906 [M − H − CH3] Wogonin-7-O-glucoside [23]
270.0526 [M + H − H − Glc − CH3]+ 268.0456 [M − H − CH3 − Glc]
65 9.51 C22H20O12 477.1026 (−2.3) 475.0892 (2) 301.0706 [M + H − H − Glucuronic acid]+ 299.0573 [M − H − Glucuronic acid] 5,4′-Dihydroxy-8-methoxy-flavone-7-O-glucuronide + [23]
286.0470 [M + H − H − Glucuronic acid − CH3]+ 284.0324 [M − H − Glucuronic acid − CH3]
66 9.8 C15H10O7 301.0356 (0.9) 273.0396 [M − H − CO] Quercetin [18]
245.0407 [M − H − CO − H2O]
178.9978
151.0035, 121.0292
107.0144
67 9.9 C21H18O11 447.0919 (−0.7) 271.0595 Baicalein-6-O-glucuronide + [23]
68 9.96 C11H12O4 207.0667 (2.1) 179.0345, 135.0469 Ethyl Caffeate s [23]
69 9.99 C22H22O11 461.1088 (−0.4) 459.0949 (3.4) 285.0759, 270.0522 283.0624, 268.0387, 175.0256, 113.0261 Wogonoside s [23]
70 10.03 C22H20O11 461.1069 (−2) 459.0949 (3.4) 285.0759 [M + H − H − Glucuronic acid]+ 283.0624 [M − H − Glucuronic acid] Oroxyloside s + [23]
270.0522 [M + H − H − Glucuronic acid − CH3]+ 268.0387 [M − H − Glucuronic acid − CH3]
71 10.33 C39H50O19 823.30066 (−1.5) 677.2421 [M + H − H − Rha]+ Epmedin C [14]
531.1840 [M + H − H−2Rha]+
369.1326 [M + H − H−2Rha − Glc]+
313.0708 [M + H − H−2Rha − Glc − C4H8]+
72 10.34 C27H30O11 531.1846 (−2.8) 369.1326 [M + H − H − Glc]+ Icariside I s [14]
313.0695 [M + H − H − Glc − C4H8]+
73 10.55 C33H40O15 677.24256 (−2.1) 675.2326 (4.7) 531.1847 [M + H − H − Rha]+ 367.1099 Icariin s + [14]
369.1332 [M + H − H − Rha − Glc]+ 269.0461 [M − H − Rha − Glc]
313.0712 [M + H − H − Rha − Glc − C4H8]+
74 11.3 C9H10O3 165.0557 (0) 150.0333 [M − H − CH3] Paeonol s + [28]
135.0094 [M − H − OCH2]
122.0385, 91.0208
75 11.44 C15H10O6 285.0407 (0.8) 241.0517 [M − H − CO2] Kaempferol s + [18]
211.0408 [M − H − CO2−OCH2]
195.0463,167.0509
76 11.56 C16H12O6 299.0563 (0.7) 284.0327 [M − H − CH3] 5,7,4’-Trihydroxy-8- [23]
240.0424 [M − H − CH3 − CO2] methoxyflavone
171.0452,153.9909
125.9968
77 11.59 C16H12O7 315.0510 (0) 300.0279 [M − H − CH3] Isorhamnetin s + [29]
282.0178 [M − H − CH3 − H2O]
255.0240, 151.0016
78 11.71 C32H38O15 663.3011 (3.1) 661.2163 (−3.5) 517.1667 [M + H − HCOOH]+ 353.0978 [M − H − Rha − Glc] Ikarisoside B + [26]
355.1165 [M + H − H − Rha − Glc]+
299.0599 [M + H − H − Rha − Glc − C4H8]+
79 11.73 C15H10O5 271.0597 (−1.6) 269.0456(1.9) 253.0500 [M + H − H2O]+ 251.036 [M − H − H2O] Baicalein s + [23]
123.0080 223.0407, 169.0664
80 12.15 C31H36O14 631.2050 (2.8) 481.1616 [M − H − Xyl] Ikarisoside F + [26]
353.1076, 352.0928, 341.0528
81 12.37 C16H12O4 269.0805 (−1.2) 267.0664 (0.4) 254.0576, 237.0532 252.0430, 223.0396, 195.0445 Formononetin s [10]
197.0599 132.0221
181.0644, 118.0416
82 12.65 C26H28O10 501.1744 (−2.3) 499.1618 (1.6) 355.1169 [M + H − H − Rha]+ 353.1043 [M − H − Rha] Baohuoside II s + [14]
299.0559 [M + H − H − Rha − C4H8]+ 309.0445 [M − H − Rha − CO2]
147.0645,129.0533
83 13.34 C33H40O15 677.2417 (−3.4) 675.2326 (4.7) 531.1847 [M + H − H − Rha]+ 367.1099 [M − H − Rha − Glc] Baohuoside VII + [26]
369.1324 [M + H − H − Rha − Glc]+ 352.0997
313.0712 [M + H − H − Rha − Glc − C4H8]+
84 13.49 C43H70O15 827.4768 (−2.3) 455.3660, 437.335 Astragaloside II [10]
175.0610,157.0474,143.1087
85 13.74 C42H68O13 781.4736 (0.4) 745.4447 Saikosaponin a [30]
619.4203, 583.3921
455.3486, 437.3374
419.3231
86 13.79 C16H12O5 285.0754 (−1.3) 283.0615 (0.9) 270.0514 [M + H − H − CH3]+ 268.0380 [M − H − CH3] Wogonin s + [23]
179.0488 163.0036
87 13.80 C32H38O14 647.2323 (−1.7) 501.1726 [M + H − H − Rha]+ Sagittatoside B + [26]
465.1557 [M + H − H − Rha − HCOOH]+
409.0917, 355.1171
299.0594
88 13.81 C16H12O5 285.0754 (−1.3) 283.0615 (0.9) 270.0514 [M + H − H − CH3]+ 268.0380 [M − H − CH3] Oroxylin A s + [23]
179.0488 163.0036
89 13.82 C32H38O14 647.2323 (−1.7) 629.2323, 501.1726, 2′′-O–Rhamnosyl-ikarisoside A [26]
465.1557, 355.1171, 299.0059
90 13.9 C33H40O14 661.2470 (−3.1) 659.2374 (4.4) 515.1897 [M + H − H − C6H10O4]+ 366.1127 2′′-O-Rhamnosyl-ikariside II + [14]
369.1333, 355.0809, 313.0703
91 13.96 C15H10O4 255.0642 (−3.9) 253.0708 (0.7) 153.0177 [M + H − H − C5H8O − H2O]+ 209.0609 [M − H − CO2] Chrysin s + [23]
103.0544 143.0505, 63.0276
92 14.01 C17H14O6 315.0856 (−2.3) 313.0718 (0.2) 300.0618, 285.0396 298.0485, 283.0252, 211.0396 Kumatakenin [29]
257.0440, 182.9919, 154.9964 155.0506
93 14.5 C24H32O7 433.2215 (−1.3) 415.2106 [M + H − H2O]+ Schisandrin s + [31]
400.1869 [M + H − H2O − CH3]+
384.1923 [M + H − H − OCH3 − H2O]+
359.14907 [M + H − H2O − C4H8]+
315.1223
94 14.63 C27H30O10 515.1901 (−2) 513.1780 (2.7) 369.1321 [M + H − H − Rha]+ 367.1134 [M − H − Rha] Icarisid II s + [14]
313.0700 [M + H − H − Rha − C4H8]+ 351.0882 [M − H − O − Rha], 323.0912
95 15.2 C45H72O16 869.4881 (−1.4) 689.4234, 437.3396 Astragaloside I s [10]
217.0720, 157.0506, 143.1059
96 15.5 C23H28O7 417.1890 (−4.2) 399.1815 [M + H − H2O]+ Schisandrol B [31]
384.1501 [M + H − H2O − CH3]+
368.1618 [M + H − H2O−OCH3]+
357.1394 [M + H − H2O − C3H6]+
343.1187 [M + H − H2O − C4H8]+
97 16.02 C30H48O5 489.3566 (−1.8) 487.3434 (1) 453.3324 [M + H − H − 2H2O]+ 469.3361 [M − H − H2O] Tormentic acid + [15]
407.3254 [M + H − HCOOH−2H2O]+ 407.1533
201.1702, 127.0767
98 16.07 C21H20O6 369.1323 (−2.6) 313.0693 Icaritin [14]
99 16.08 C15H10O5 271.0596 (−2) 269.0460 (1.5) 225.0560, 241.0514, 197.0608, 182.0375 Emodin s + [18]
100 17.88 C23H30O6 403.2112 (−0.8) 388.1848 [M + H − H − CH3]+, Schisanhenol [31]
372.1919 [M + H − H − OCH3]+
371.1859 [M + H − H − CH3OH]+
333.1326, 302.1149
101 19.09 C28H34O9 515.2264 (−2.3) 415.2009 [M + H − H − C4H6COOH]+ Schisantherin B [31]
385.1637 [M + H − H − C4H6COOH − OCH2]+
355.1534, 343.1160, 316.0939
102 20.31 C24H32O6 417.2259 (−3) 402.1999 [M + H − H − CH3]+ Schizandrin A s [31]
386.2059 [M + H − H − OCH3]+
347.1480 [M + H − H − C5H10]+
316.1289 [M + H − H − C5H10 − OCH3]+
301.1058, 285.1104, 273.1091, 242.0911
103 21.3 C23H28O6 401.1948 (−2.6) 386.1728 [M + H − H − CH3]+ γ-Schizandrin B s [31]
331.1168 [M + H − H − C5H10]+
300.0987, 242.0929
104 21.87 C22H24O6 385.1638 (−1.9) 355.1561 [M + H − H − OCH2]+ Schizandrin C [31]
315.0895 [M + H − H − C5H10]+
285.0757 [M + H − H − C5H10−OCH2]+
257.0809, 242.0588, 227.0703, 153.0663
105 22.98 C32H50O5 515.3723 (−1.6) 513.3594 (1.7) 409.3466, 191.1793 495.3496 [M − H − H2O] 19α−Hydroxyl−3−acetyl ursolic acid [15]
469.3720 [M − H − CO2]
106 23.56 C30H48O3 455.3537 (1.3) Oleanic acid s [15]
107 23.73 C30H48O3 455.3537 (1.3) Ursolic acid [15]

“s” Identified with reference compounds; “+”: detected and “−”not detected.