Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in Oats
Digalactosyldiacylglycerol- (DGDG-) monoestolide is a characteristic glycolipid in oats. DGDG-monoestolides possess a unique structure whereby a fatty acid of DGDG is replaced by a fatty acid ester of hydroxy fatty acid (FAHFA). While the physiological effects of DGDG and FAHFA have been reported pr...
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MDPI AG
2022-10-01
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| author | Hiroki Yamada Junya Ito Naoki Shimizu Takumi Takahashi Chikara Kato Isabella Supardi Parida Mirinthorn Jutanom Katsuyuki Ishihara Kiyotaka Nakagawa |
| author_facet | Hiroki Yamada Junya Ito Naoki Shimizu Takumi Takahashi Chikara Kato Isabella Supardi Parida Mirinthorn Jutanom Katsuyuki Ishihara Kiyotaka Nakagawa |
| author_sort | Hiroki Yamada |
| collection | DOAJ |
| description | Digalactosyldiacylglycerol- (DGDG-) monoestolide is a characteristic glycolipid in oats. DGDG-monoestolides possess a unique structure whereby a fatty acid of DGDG is replaced by a fatty acid ester of hydroxy fatty acid (FAHFA). While the physiological effects of DGDG and FAHFA have been reported previously, the effects of DGDG-monoestolides are unknown. Hence, we isolated a major DGDG-monoestolide molecular species from oats, analyzed its structure, and evaluated its anti-inflammatory effect. Based on GC-MS, MS/MS, and NMR analyses, the isolated compound was identified as a DGDG-monoestolide that contains the linoleic acid ester of 15-hydroxy linoleic acid (LAHLA) and linoleic acid (i.e., DGDG-LAHLA). The isolated DGDG-LAHLA was evaluated for its anti-inflammatory effect on LPS-stimulated RAW264 cells. The production of nitric oxide and cytokines (IL-6, TNF-<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mi mathvariant="sans-serif">α</mi></semantics></math></inline-formula>, and IL-10) were significantly decreased by DGDG-LAHLA, suggesting the anti-inflammatory effect of DGDG-LAHLA for the first time. In addition, our data showed a pronounced uptake of DGDG-LAHLA by cells. Some compounds corresponding to the predicted DGDG-LAHLA metabolites were also detected, suggesting that both intact DGDG-LAHLA and its metabolites may contribute to the above anti-inflammatory activities. These results are expected to expand the availability of oats as a functional food. |
| first_indexed | 2024-03-09T21:18:35Z |
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| institution | Directory Open Access Journal |
| issn | 2072-6643 |
| language | English |
| last_indexed | 2024-03-09T21:18:35Z |
| publishDate | 2022-10-01 |
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| record_format | Article |
| series | Nutrients |
| spelling | doaj.art-25b88cb2b05b470bb89639a7e853d0602023-11-23T21:26:33ZengMDPI AGNutrients2072-66432022-10-011419415310.3390/nu14194153Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in OatsHiroki Yamada0Junya Ito1Naoki Shimizu2Takumi Takahashi3Chikara Kato4Isabella Supardi Parida5Mirinthorn Jutanom6Katsuyuki Ishihara7Kiyotaka Nakagawa8Laboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, JapanDepartment of Cell Biology, Division of Host Defense Mechanism, Tokai University School of Medicine, Isehara 259-1193, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, JapanR&D Center, Calbee, Inc., Utsunomiya 321-3231, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, JapanDigalactosyldiacylglycerol- (DGDG-) monoestolide is a characteristic glycolipid in oats. DGDG-monoestolides possess a unique structure whereby a fatty acid of DGDG is replaced by a fatty acid ester of hydroxy fatty acid (FAHFA). While the physiological effects of DGDG and FAHFA have been reported previously, the effects of DGDG-monoestolides are unknown. Hence, we isolated a major DGDG-monoestolide molecular species from oats, analyzed its structure, and evaluated its anti-inflammatory effect. Based on GC-MS, MS/MS, and NMR analyses, the isolated compound was identified as a DGDG-monoestolide that contains the linoleic acid ester of 15-hydroxy linoleic acid (LAHLA) and linoleic acid (i.e., DGDG-LAHLA). The isolated DGDG-LAHLA was evaluated for its anti-inflammatory effect on LPS-stimulated RAW264 cells. The production of nitric oxide and cytokines (IL-6, TNF-<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mi mathvariant="sans-serif">α</mi></semantics></math></inline-formula>, and IL-10) were significantly decreased by DGDG-LAHLA, suggesting the anti-inflammatory effect of DGDG-LAHLA for the first time. In addition, our data showed a pronounced uptake of DGDG-LAHLA by cells. Some compounds corresponding to the predicted DGDG-LAHLA metabolites were also detected, suggesting that both intact DGDG-LAHLA and its metabolites may contribute to the above anti-inflammatory activities. These results are expected to expand the availability of oats as a functional food.https://www.mdpi.com/2072-6643/14/19/4153DGDG-estolidesDGDGFAHFAoats<i>Avena sativa</i>anti-inflammatory effect |
| spellingShingle | Hiroki Yamada Junya Ito Naoki Shimizu Takumi Takahashi Chikara Kato Isabella Supardi Parida Mirinthorn Jutanom Katsuyuki Ishihara Kiyotaka Nakagawa Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in Oats Nutrients DGDG-estolides DGDG FAHFA oats <i>Avena sativa</i> anti-inflammatory effect |
| title | Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in Oats |
| title_full | Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in Oats |
| title_fullStr | Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in Oats |
| title_full_unstemmed | Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in Oats |
| title_short | Structural Analysis and Anti-Inflammatory Effect of a Digalactosyldiacylglycerol-Monoestolide, a Characteristic Glycolipid in Oats |
| title_sort | structural analysis and anti inflammatory effect of a digalactosyldiacylglycerol monoestolide a characteristic glycolipid in oats |
| topic | DGDG-estolides DGDG FAHFA oats <i>Avena sativa</i> anti-inflammatory effect |
| url | https://www.mdpi.com/2072-6643/14/19/4153 |
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