Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin
Gardenia blue (GB), a natural active blue pigment, can be synthesized from iridoid glycosides and primary amino-containing compounds in vivo and in vitro. However, limited studies have reported about GB synthetic intermediates, leading to unawareness of the formation mechanism of GB. Here, we report...
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| Language: | English |
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Elsevier
2025-01-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535224004507 |
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| author | Xiaoyu Zhang Ruihu Zhang Rui Li Jiaxing Zhang Yuefei Wang Xin Chai Yuefei Wang |
| author_facet | Xiaoyu Zhang Ruihu Zhang Rui Li Jiaxing Zhang Yuefei Wang Xin Chai Yuefei Wang |
| author_sort | Xiaoyu Zhang |
| collection | DOAJ |
| description | Gardenia blue (GB), a natural active blue pigment, can be synthesized from iridoid glycosides and primary amino-containing compounds in vivo and in vitro. However, limited studies have reported about GB synthetic intermediates, leading to unawareness of the formation mechanism of GB. Here, we reported that GB could be detected in rats′ feces, whose formation was simulated by in vitro reaction of amino acid-rich feces extract from rats and genipin (GP) metabolized from geniposide (GE) through β-glucosidase. Firstly, we proved that 14 amino acids (AAs) detected in rats′ feces containing primary amino groups can react with GP to produce GB. Then, taking histidine (His) as example, we characterized the key intermediates during the reaction process, including basic units genihistidine A (GH-A) and dimers. As an active basic unit, GH-A underwent covalent polymerization to form dimer, which then self-assembled into supramolecular spherical nanoparticles through multiple noncovalent interactions, including hydrogen bonds, π-π interactions, and van der Waals interactions. Our study revealed the formation mechanism of GB and provided insights into the bioavailable form of GE from traditional Chinese medicine in vivo. |
| format | Article |
| id | doaj-art-fc25f6fdb14945e09b550de74fe80d2c |
| institution | Kabale University |
| issn | 1878-5352 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj-art-fc25f6fdb14945e09b550de74fe80d2c2024-12-26T08:52:51ZengElsevierArabian Journal of Chemistry1878-53522025-01-01181106048Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipinXiaoyu Zhang0Ruihu Zhang1Rui Li2Jiaxing Zhang3Yuefei Wang4Xin Chai5Yuefei Wang6State Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China; Sichuan-Chongqing Joint Key Laboratory of Innovation of New Drugs of Traditional Chinese Medicine, Chongqing Academy of Chinese Materia Medica, Chongqing 400065, ChinaState Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, ChinaState Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, ChinaSchool of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, ChinaSchool of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, China; Tianjin Key Laboratory of Membrane Science and Desalination Technology, Tianjin University, Tianjin 300072, China; Corresponding author at: School of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, China.State Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China; Haihe Laboratory of Modern Chinese Medicine, Tianjin 301617, China; Corresponding author at: State Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, ChinaState Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China; Haihe Laboratory of Modern Chinese Medicine, Tianjin 301617, China; Corresponding author at: State Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, China.Gardenia blue (GB), a natural active blue pigment, can be synthesized from iridoid glycosides and primary amino-containing compounds in vivo and in vitro. However, limited studies have reported about GB synthetic intermediates, leading to unawareness of the formation mechanism of GB. Here, we reported that GB could be detected in rats′ feces, whose formation was simulated by in vitro reaction of amino acid-rich feces extract from rats and genipin (GP) metabolized from geniposide (GE) through β-glucosidase. Firstly, we proved that 14 amino acids (AAs) detected in rats′ feces containing primary amino groups can react with GP to produce GB. Then, taking histidine (His) as example, we characterized the key intermediates during the reaction process, including basic units genihistidine A (GH-A) and dimers. As an active basic unit, GH-A underwent covalent polymerization to form dimer, which then self-assembled into supramolecular spherical nanoparticles through multiple noncovalent interactions, including hydrogen bonds, π-π interactions, and van der Waals interactions. Our study revealed the formation mechanism of GB and provided insights into the bioavailable form of GE from traditional Chinese medicine in vivo.http://www.sciencedirect.com/science/article/pii/S1878535224004507GenipinAmino acidGardenia blue pigmentgenihistidine ASupramolecular assembliesMolecular dynamics simulation |
| spellingShingle | Xiaoyu Zhang Ruihu Zhang Rui Li Jiaxing Zhang Yuefei Wang Xin Chai Yuefei Wang Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin Arabian Journal of Chemistry Genipin Amino acid Gardenia blue pigment genihistidine A Supramolecular assemblies Molecular dynamics simulation |
| title | Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin |
| title_full | Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin |
| title_fullStr | Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin |
| title_full_unstemmed | Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin |
| title_short | Elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin |
| title_sort | elucidating the formation mechanism of gardenia blue pigment from amino acid and genipin |
| topic | Genipin Amino acid Gardenia blue pigment genihistidine A Supramolecular assemblies Molecular dynamics simulation |
| url | http://www.sciencedirect.com/science/article/pii/S1878535224004507 |
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