Piperazine-2,5-dione derivatives and an α-pyrone polyketide from Penicillium griseofulvum and their immunosuppression activity
| Autor: | Junjun Liu, Chunmei Chen, Xia Chen, Jianping Wang, Huiling Wen, Changxing Qi, Yihua Gong, Hucheng Zhu, Yi Zang, Zengwei Luo, Yonghui Zhang |
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| Rok vydání: | 2020 |
| Předmět: |
0106 biological sciences
Penicillium griseofulvum Stereochemistry Plant Science Horticulture Ring (chemistry) 01 natural sciences Biochemistry chemistry.chemical_compound Polyketide Mice Animals Molecular Biology Piperazine Trichocomaceae Immunosuppression Therapy biology Molecular Structure 010405 organic chemistry Penicillium General Medicine Oxime biology.organism_classification Piperazinedione Pyrone 0104 chemical sciences chemistry Pyrones Polyketides 010606 plant biology & botany |
| Zdroj: | Phytochemistry. 186 |
| ISSN: | 1873-3700 |
| Popis: | Four undescribed piperazine-2,5-dione derivatives designated janthinolides C–F, and an α-pyrone-containing polyketide namely trichopyrone C, were isolated from the extract of the fungus Penicillium griseofulvum along with four known products. Among them, janthinolide C represents the first naturally occured piperazine-2,5-dione analogue featuring a cleavaged piperazinedione ring with an oxime group, while the structure of janthinolide D possesses a rare N-methoxy group in natural products. Their structures and absolute stereochemistry were elucidated based on spectroscopic data, theoretical NMR and ECD calculations, Snatzke's method, and modified Mosher's method. All compounds were evaluated for in vitro immunosuppression activity in murine splenocytes stimulated by anti-CD3/anti-CD28 mAbs, of which janthinolides B and C showed potential inhibitory activity with IC50 values at 9.3 and 1.3 μM, respectively. |
| Databáze: | OpenAIRE |
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