Chemical Analysis of Sorghum Husk by UPLC-Q Exactive Plus-MS in Vitro Screening of Xanthine Oxidase Inhibitory Activity and Composition

doi:10.19894/j.issn.1000-0518.230147

Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (11): 1587-1594.DOI: 10.19894/j.issn.1000-0518.230147

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Chemical Analysis of Sorghum Husk by UPLC-Q Exactive Plus-MS in Vitro Screening of Xanthine Oxidase Inhibitory Activity and Composition

Han-Shui ZHANG¹, Ben-Yi GONG¹, Min-Lun NAN², Yu-Fang HE³, Yu-Wei ZHAO³, Cong-Mei WU¹, Yu-He YIN¹()

^1.College of Chemistry and Life Sciences，Changchun University of Technology，Changchun 130012，China
^2.Institute of Phytochemistry，Academy of Chinese Medicine of Jilin Province，Changchun 130012，China
^3.College of Health Management，Changchun University of Traditional Chinese Medicine，Changchun 130117，China

Received:2023-05-16 Accepted:2023-07-25 Published:2023-11-01 Online:2023-12-01
Contact: Yu-He YIN
About author:yinyuhe@ccut.edu.cn
Supported by:
Jilin Province Science and Technology Development Plan Project(20220204014YY)

Abstract

Abstract:

The chemical components in sorghum husk are analyzed and identified by high performance liquid chromatography tandem with quadrupole electrostatic field orbital trap mass spectrometry and screened for inhibition of xanthine oxidase activity components by high performance liquid chromatography. The experiment is performed on a Hypersil GOLD C18 column （2.1 nm×30 nm， 3 μm） with a gradient elution of 0.1% formic acid water （A）-acetonitrile （B） at a flow rate of 1.0 mL/min and a sample volume of 10 μL. The mass spectrometry analysis is performed using an ESI ion source and data are collected in positive ion mode. The data obtained are analyzed using Xcalibur 4.1 software in combination with a database， and a total of 27 chemical components are identified. Six chemical components， namely acacetin， puerarin， apigenin， phlorizin， isorhamnetin and fisetin， are screened for activity， and apigenin and fisetin are found to exhibit strong inhibitory activity on xanthine oxidase （XO） with IC₅₀ of 18.11 and 34.59 μmol/L， respectively.

Key words: Sorghum husk, Chemical composition identificationXanthine, Mass Spectrometry Fragmentation Mechanisms, Xanthine oxidase, Inhibition of active ingredients

CLC Number:

O656

Han-Shui ZHANG, Ben-Yi GONG, Min-Lun NAN, Yu-Fang HE, Yu-Wei ZHAO, Cong-Mei WU, Yu-He YIN. Chemical Analysis of Sorghum Husk by UPLC-Q Exactive Plus-MS in Vitro Screening of Xanthine Oxidase Inhibitory Activity and Composition[J]. Chinese Journal of Applied Chemistry, 2023, 40(11): 1587-1594.

Figures/Tables 6

References 18

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No	t_R/min	Composition	Molecular formula	Measured m/z	Fragments（MS/MS）	Delta m/z
1	36.90	2-（3-Phenylpropyl）pyridine	C₁₄H₁₅N	198.128 1	91.054 9，106.065 7	-0.04
2	39.64	2'，6-Dihydroxyflavone	C₁₅H₁₀O₄	255.065 5	119.029 0，211.064 9，227.070 5	-0.02
3	39.91	Acacetin	C₁₆H₁₂O₅	285.076 5	242.057 6，270.052 4	0.67
4	42.29	2'，3'，6-Trimethoxyflavone	C₁₈H₁₆O₅	313.071 4	280.037 8，295.060 9	0.09
5	44.07	5-Hydroxy-3'-methoxyflavone	C₁₆H₁₂O₄	269.081 2	226.062 8，254.057 8	-0.03
6	45.64	3-Hydroxy-3'-methoxyflavone	C₁₆H₁₂O₄	269.081 2	226.063 0，254.057 8	-0.03
7	49.87	2'，5-Dimethoxyflavone	C₁₇H₁₄O₄	283.097 0	239.070 7，268.073 4	-0.03
8	57.29	1，5-Dihydroxyanthraquinone	C₁₄H₈O₄	241.097 6	167.061 0，185.071 5，213.066 3	-0.23
9	57.97	Licolisoflavone A	C₂₀H₁₈O₆	355.118 6	152.512 8	0.67
10	60.52	Epigallocatechin-3-gallate	C₂₂H₁₈O₁₁	459.144 7	127.035 7，181.068 2	0.13
11	60.97	Puerarin	C₂₁H₂₀O₉	417.134 0	255.862 5	0.59
12	61.32	Ipriflavone	C₁₈H₁₆O₃	281.081 7	239.070 7	0.10
13	62.68	Daidzein	C₂₁H₂₀O₉	417.133 7	224.128 5	0.10
14	63.99	Catechin gallate	C₂₂H₁₈O₁₀	443.113 4	111.032 4，163.076 5，181.043 1，247.081 2	-0.05
15	66.29	2，4-Dihydroxybenzophenone	C₁₃H₁₀O₃	215.034 3	95.013 5	0.13
16	70.07	3'，7-Dimethoxy-3-hydroxyflavone	C₁₇H₁₄O₅	299.092 2	255.065 2，284.068 7	-0.03
17	72.05	Apigenin	C₁₅H₁₀O₅	271.060 6	119.049 7，227.381 3，243.065 7	-0.03
18	72.80	Carviolin	C₁₆H₁₂O₆	301.071 2	258.052 9，286.047 7	-0.03
19	74.71	Phlorizin	C₂₁H₂₄O₁₀	437.121 0	166.470 1，257.116 9	0.04
20	77.94	Syringetin-3-O-glucoside	C₂₃H₂₄O₁₃	509.124 7	347.066 1	-0.06
21	78.17	Fisetin	C₁₅H₁₀O₆	287.055 5	149.060 2，251.012 7	-0.03
22	78.40	LicochalconeA	C₂₁H₂₂O₄	339.050 6	94.077 0	1.04
23	80.03	Apigenin-7-O-glucoside	C₂₁H₂₀O₁₀	433.129 0	271.053 5	0.58
24	80.85	6-Ethoxy-3（4'-hydroxyphenyl）-4-methylcoumarin	C₁₈H₁₆O₄	297.076 4	153.018 6	0.09
25	82.86	3，7-Dihydroxy-3'，4'-dimethoxyflavone	C₁₇H₁₄O₆	315.086 8	271.060 5，300.063 6	-0.02
26	89.26	Isorhamnetin	C₁₆H₁₂O₇	317.103 0	121.616 7，183.029 5，217.434 2	0.51
27	97.97	Ethyl 4-（dimethylamino）benzoate	C₁₁H₁₅NO₂	194.118 0	107.049 7，135.044 4	-0.04

No	t_R/min	Composition	Molecular formula	Measured m/z	Fragments（MS/MS）	Delta m/z
1	36.90	2-（3-Phenylpropyl）pyridine	C₁₄H₁₅N	198.128 1	91.054 9，106.065 7	-0.04
2	39.64	2'，6-Dihydroxyflavone	C₁₅H₁₀O₄	255.065 5	119.029 0，211.064 9，227.070 5	-0.02
3	39.91	Acacetin	C₁₆H₁₂O₅	285.076 5	242.057 6，270.052 4	0.67
4	42.29	2'，3'，6-Trimethoxyflavone	C₁₈H₁₆O₅	313.071 4	280.037 8，295.060 9	0.09
5	44.07	5-Hydroxy-3'-methoxyflavone	C₁₆H₁₂O₄	269.081 2	226.062 8，254.057 8	-0.03
6	45.64	3-Hydroxy-3'-methoxyflavone	C₁₆H₁₂O₄	269.081 2	226.063 0，254.057 8	-0.03
7	49.87	2'，5-Dimethoxyflavone	C₁₇H₁₄O₄	283.097 0	239.070 7，268.073 4	-0.03
8	57.29	1，5-Dihydroxyanthraquinone	C₁₄H₈O₄	241.097 6	167.061 0，185.071 5，213.066 3	-0.23
9	57.97	Licolisoflavone A	C₂₀H₁₈O₆	355.118 6	152.512 8	0.67
10	60.52	Epigallocatechin-3-gallate	C₂₂H₁₈O₁₁	459.144 7	127.035 7，181.068 2	0.13
11	60.97	Puerarin	C₂₁H₂₀O₉	417.134 0	255.862 5	0.59
12	61.32	Ipriflavone	C₁₈H₁₆O₃	281.081 7	239.070 7	0.10
13	62.68	Daidzein	C₂₁H₂₀O₉	417.133 7	224.128 5	0.10
14	63.99	Catechin gallate	C₂₂H₁₈O₁₀	443.113 4	111.032 4，163.076 5，181.043 1，247.081 2	-0.05
15	66.29	2，4-Dihydroxybenzophenone	C₁₃H₁₀O₃	215.034 3	95.013 5	0.13
16	70.07	3'，7-Dimethoxy-3-hydroxyflavone	C₁₇H₁₄O₅	299.092 2	255.065 2，284.068 7	-0.03
17	72.05	Apigenin	C₁₅H₁₀O₅	271.060 6	119.049 7，227.381 3，243.065 7	-0.03
18	72.80	Carviolin	C₁₆H₁₂O₆	301.071 2	258.052 9，286.047 7	-0.03
19	74.71	Phlorizin	C₂₁H₂₄O₁₀	437.121 0	166.470 1，257.116 9	0.04
20	77.94	Syringetin-3-O-glucoside	C₂₃H₂₄O₁₃	509.124 7	347.066 1	-0.06
21	78.17	Fisetin	C₁₅H₁₀O₆	287.055 5	149.060 2，251.012 7	-0.03
22	78.40	LicochalconeA	C₂₁H₂₂O₄	339.050 6	94.077 0	1.04
23	80.03	Apigenin-7-O-glucoside	C₂₁H₂₀O₁₀	433.129 0	271.053 5	0.58
24	80.85	6-Ethoxy-3（4'-hydroxyphenyl）-4-methylcoumarin	C₁₈H₁₆O₄	297.076 4	153.018 6	0.09
25	82.86	3，7-Dihydroxy-3'，4'-dimethoxyflavone	C₁₇H₁₄O₆	315.086 8	271.060 5，300.063 6	-0.02
26	89.26	Isorhamnetin	C₁₆H₁₂O₇	317.103 0	121.616 7，183.029 5，217.434 2	0.51
27	97.97	Ethyl 4-（dimethylamino）benzoate	C₁₁H₁₅NO₂	194.118 0	107.049 7，135.044 4	-0.04

Sample	Inhibition ratio/%						IC₅₀/（μmol·L^-1）
Sample	50 μmol/L	100 μmol/L	200 μmol/L	400 μmol/L	800 μmol/L	1600 μmol/L	IC₅₀/（μmol·L^-1）
Acacetin	10.9	19.8	32.5	44.6	49.7	52.8	90.53
Puerarin	12.8	21.9	38.7	51.6	62.5	68.2	43.67
Apigenin	22.8	39.8	52.8	69.8	79.1	82.4	18.11
Phlorizin	6.9	13.5	29.5	53.2	68.2	70.1	45.05
Isorhamnetin	6.5	11.9	22.1	32.1	38.2	42.1	＞100
Fisetin	14.6	26.4	43.7	56.7	64.4	73.2	34.59
Allopurinol	16.5	27.6	41.5	55.8	70.7	78.9	32.38

Sample	Inhibition ratio/%						IC₅₀/（μmol·L^-1）
Sample	50 μmol/L	100 μmol/L	200 μmol/L	400 μmol/L	800 μmol/L	1600 μmol/L	IC₅₀/（μmol·L^-1）
Acacetin	10.9	19.8	32.5	44.6	49.7	52.8	90.53
Puerarin	12.8	21.9	38.7	51.6	62.5	68.2	43.67
Apigenin	22.8	39.8	52.8	69.8	79.1	82.4	18.11
Phlorizin	6.9	13.5	29.5	53.2	68.2	70.1	45.05
Isorhamnetin	6.5	11.9	22.1	32.1	38.2	42.1	＞100
Fisetin	14.6	26.4	43.7	56.7	64.4	73.2	34.59
Allopurinol	16.5	27.6	41.5	55.8	70.7	78.9	32.38

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Chemical Analysis of Sorghum Husk by UPLC-Q Exactive Plus-MS in Vitro Screening of Xanthine Oxidase Inhibitory Activity and Composition

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