Beneficial Regulatory Effects of Polymethoxyflavone—Rich Fraction from Ougan (Citrus reticulata cv. Suavissima) Fruit on Gut Microbiota and Identification of Its Intestinal Metabolites in Mice
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials and Animals
2.2. Extraction of PMF-Rich Fraction from Ougan Fruit
2.3. Collection of the Intestinal Contents
2.4. Extraction of Flavonoid Components from the Intestinal Contents
2.5. Identification of Flavonoids
2.6. DNA Extraction and 16S ribosomal DNA Sequencing of Intestinal Content from Mice
2.7. Sequencing Data Processing
2.8. Statistical Analysis
3. Results
3.1. Identification of PMF-Rich Fraction
3.2. Identification of Metabolites of PMFs in Intestinal Content
3.3. Effects of PMF-Rich Fraction on Gut Microbiota
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Peak No. | Retention Time (min) | [M + H]+ or [M − H]− (m/z) | Error (ppm) | Formula | Fragment Ions (m/z) | Tentative Compounds |
---|---|---|---|---|---|---|
1 | 13.4438 | 609.1827 (-) | 0.5 | C28H34O15 | 489, 343, 301, 286, 242 | Neohesperidin |
2 | 21.2998 | 593.1876 (-) | 0.0 | C28H34O14 | 285 | Poncirin |
3 | 29.1432 | 373.1291 | 2.2 | C20H20O7 | 358, 343, 327, 315, 299, 181, 163, 153 | Isosinensetin |
4 | 29.3402 | 389.1231 | 2.6 | C20H20O8 | 374, 359, 344, 331, 313, 298, 287, 211, 183 | Monohydroxy-pentamethoxyflavone |
5 | 31.3811 | 373.1282 | 0.9 | C20H20O7 | 357, 343, 329, 312, 297, 153 | Sinensetin |
6 | 31.8459 | 343.1176 | 0.8 | C19H18O6 | 328, 313, 285, 257, 181, 153 | Tetramethyl-O-isoscutellarein |
7 | 33.4704 | 403.1387 | 0.6 | C21H22O8 | 388, 373, 358, 355, 327, 211, 183 | Nobiletin |
8 | 33.853 | 375.1074 | 1.7 | C19H18O8 | 360, 345, 330, 327, 317, 302, 197, 169, 149 | 5,4′-Dihydroxyl-3,7,8,3′-tetramethoxyflavone |
9 | 34.0789 | 343.1176 | 2.0 | C19H18O6 | 328, 313, 285, 257, 181, 153 | Tetramethyl-O-scutellarein |
10 | 35.9401 | 373.1282 | 0.3 | C20H20O7 | 358, 343, 328, 297, 211, 183 | Tangeretin |
11 | 37.8647 | 389.1231 | 0.5 | C20H20O8 | 374, 359, 341, 331, 197 | 5-demethylnobiletin |
Peak No. | Retention Time (min) | [M + H]+ or [M − H]− (m/z) | Formula | Fragment Ions (m/z) | Tentative Compounds |
---|---|---|---|---|---|
1 | 13.1284 | 609.1825 (-) | C28H34O15 | 489, 343, 325, 301, 286, 257, 242, 164 | Neohesperidin |
2 | 16.3972 | 563.1460 (-) | C26H28O14 | 387, 372, 357, 342, 314, 299, 175, 113 | Nobelitin-O-glucuronide (1) |
3 | 18.8731 | 535.1449 | C25H26O13 | 359, 344, 329, 314, 311, 301, 298, 286, 283, 257 | Tangeretin-O-glucuronide (1) |
4 | 19.5825 | 565.1555 | C26H28O14 | 389, 374, 359, 345, 344, 343, 341, 331, 328, 327, 316, 315, 313 | Nobelitin-O-glucuronide (2) |
5 | 19.8712 | 565.1551 | C26H28O14 | 389, 374, 359, 345, 344, 343, 341, 339, 331, 329, 328, 327, 316, 315, 313, 310, 301, 298 | Nobelitin-O-glucuronide (3) |
6 | 20.1621 | 375.1078 | C19H18O8 | 360, 345, 330, 327, 317, 302, 299, 197, 169, 149 | Dihydroxy-tetramethoxyflavone (1) |
7 | 21.0102 | 287.0917 | C16H14O5 | 161, 153, 135, 133, 125, 121, 118, 111, 103, 97, 69, 67 | Dihydroxy-monomethoxyflavone |
8 | 21.5526 | 345.0974 | C18H16O7 | 330, 315, 297, 287, 272, 197, 169 | Dihydroxy-trimethoxyflavone |
9 | 22.4321 | 375.1081 | C19H18O8 | 360, 345, 330, 327, 317, 302, 197, 169 | Dihydroxy-tetramethoxyflavone (2) |
10 | 22.6898 | 327.0874 (-) | C18H16O6 | 327, 312, 297, 282, 269, 254, 226, 182, 177, 117 | Monohydroxy-trimethoxyflavone |
11 | 23.5766 | 535.1449 | C25H26O13 | 359, 344, 329, 311 | Tangeretin-O-glucuronide(2) |
12 | 24.0618 | 375.1081 | C19H18O8 | 360, 345, 331, 330, 327, 317, 314, 302, 301, 299, 287, 285, 274, 273, 271, 211, 183, 168, 165, 147, 139, 137, 135, 134, 127 | Dihydroxy-tetramethoxyflavone (3) |
13 | 24.2942 | 375.1084 | C19H18O8 | 360, 345, 331, 330, 327, 325, 317, 314, 313, 302, 299, 287, 285, 274, 273, 271, 230, 211, 183, 168, 137, 135, 127 | Dihydroxy-tetramethoxyflavone (4) |
14 | 24.6514 | 565.1555 | C26H28O14 | 389, 374, 359, 356, 341 | Nobelitin-O-glucuronide (4) |
15 | 25.8876 | 389.1237 | C20H20O8 | 374, 359, 356, 341, 331, 316, 285, 244, 197, 169, 163, 148, 113 | Monohydroxy-pentamethoxyflavone (1) |
16 | 26.0809 | 271.0607 | C15H10O5 | 253, 243, 215, 197, 169, 153, 149, 115, 91 | Trihydroxy-flavone |
17 | 26.6764 | 359.1135 | C19H18O7 | 344, 343, 341, 329, 327, 325, 315, 301, 300, 298, 297, 283, 272, 255, 227, 181, 153 | Monohydroxy-tetramethoxyflavone (1) |
18 | 27.7937 | 389.1238 | C20H20O8 | 374, 359, 344, 343, 341, 331, 316, 197, 169, 165, 163 | Monohydroxy-pentamethoxyflavone (2) |
19 | 28.4142 | 359.1128 | C19H18O7 | 344, 329, 315, 314, 311, 309, 301, 298, 297, 286, 285, 283, 271, 268, 258, 257, 255, 240, 230, 228, 215, 214, 212, 211, 200, 193, 187, 183, 168, 165, 139, 131, 127, 121 | Monohydroxy-tetramethoxyflavone (2) |
20 | 29.1096 | 389.1234 | C20H20O8 | 374, 359, 345, 344, 343, 341, 339, 331, 328, 326, 316, 315, 313, 310, 301, 299, 288, 287, 285, 270, 260, 245, 230, 217, 211, 193, 183, 168, 151, 127 | Monohydroxy-pentamethoxyflavone (3) |
21 | 29.5447 | 359.0772 | C17H14O6 | 344, 329, 314, 311, 301, 286, 283, 258, 242, 230, 214, 202, 193, 177, 174, 133 | Dihydroxy-dimethoxyflavone |
22 | 30.7912 | 359.1135 | C19H18O7 | 344, 329, 314, 311, 301, 286, 283, 197, 169, 133 | Monohydroxy-tetramethoxyflavone (3) |
23 | 31.4917 | 343.1182 | C19H18O6 | 328, 313, 285, 181, 153, 133 | Tetramethoxyflavone |
24 | 33.2004 | 403.1395 | C21H22O8 | 388, 387, 373, 359, 358, 357, 355, 353, 345, 343, 341, 339, 330, 327, 325, 315, 313, 311, 301, 299, 259, 257, 244, 231, 211, 193, 183, 175, 168, 163, 162 | Nobiletin |
25 | 35.6699 | 373.1291 | C20H20O7 | 358, 343, 325, 315, 300, 297, 283, 271, 269, 229, 211, 193, 183, 168, 135 | Tangeretin |
26 | 37.6439 | 389.1241 | C20H20O8 | 374, 359, 356, 341, 343, 328, 316, 313, 197, 169, 163 | 5-demethylnobiletin |
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Chen, J.; Wang, Y.; Zhu, T.; Yang, S.; Cao, J.; Li, X.; Wang, L.-S.; Sun, C. Beneficial Regulatory Effects of Polymethoxyflavone—Rich Fraction from Ougan (Citrus reticulata cv. Suavissima) Fruit on Gut Microbiota and Identification of Its Intestinal Metabolites in Mice. Antioxidants 2020, 9, 831. https://0-doi-org.brum.beds.ac.uk/10.3390/antiox9090831
Chen J, Wang Y, Zhu T, Yang S, Cao J, Li X, Wang L-S, Sun C. Beneficial Regulatory Effects of Polymethoxyflavone—Rich Fraction from Ougan (Citrus reticulata cv. Suavissima) Fruit on Gut Microbiota and Identification of Its Intestinal Metabolites in Mice. Antioxidants. 2020; 9(9):831. https://0-doi-org.brum.beds.ac.uk/10.3390/antiox9090831
Chicago/Turabian StyleChen, Jiebiao, Yue Wang, Tailin Zhu, Sijia Yang, Jinping Cao, Xian Li, Li-Shu Wang, and Chongde Sun. 2020. "Beneficial Regulatory Effects of Polymethoxyflavone—Rich Fraction from Ougan (Citrus reticulata cv. Suavissima) Fruit on Gut Microbiota and Identification of Its Intestinal Metabolites in Mice" Antioxidants 9, no. 9: 831. https://0-doi-org.brum.beds.ac.uk/10.3390/antiox9090831