Absolute configuration of polypropionate derivatives: Decempyrones A–J and their MptpA inhibition and anti-inflammatory activities
[Display omitted] •Ten new polypropionate derivatives, decempyrones A–J (1–10) were isolated from Fusarium graminearum.•Absolute configurations were fixed by JBCA, chemical degradation, geminal proton rule, and modified Mosher’s method.•Decempyrones C and J exhibited potent anti-inflammatory activit...
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| Published in | Bioorganic chemistry Vol. 115; pp. 105156 - 105165 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
SAN DIEGO
Elsevier Inc
01.10.2021
Elsevier |
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| Online Access | Get full text |
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| Abstract | [Display omitted]
•Ten new polypropionate derivatives, decempyrones A–J (1–10) were isolated from Fusarium graminearum.•Absolute configurations were fixed by JBCA, chemical degradation, geminal proton rule, and modified Mosher’s method.•Decempyrones C and J exhibited potent anti-inflammatory activity.•Decempyrones C and J also displayed MptpA kinase inhibitory activity.
Under guidance of 1H NMR, ten new polypropionate derivatives, decempyrones A–J (1–10) along with two known analogues (11 and 12), were isolated from the marine-derived fungusFusarium decemcellulare SYSU-MS6716. The planar structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, and HR-ESIMS). The absolute configuration of the chiral centers in the side chain is a major obstacle for the structure identification of natural polypropionate derivatives. Herein, the J-based configurational analysis (JBCA), chemical degradation, geminal proton rule, and the modified Mosher’s method were adopted to fix their absolute configurations in the side chain. Compounds 3 and 10 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50values 22.4 ± 1.8 and 21.7 ± 1.1 μM. In addition, compounds 3 and 10 displayed MptpA inhibitory activity with an IC50 value of 19.2 ± 0.9 and 33.1 ± 2.9 µM. Structure-activity relationships of the polypropionate derivatives were discussed. |
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| AbstractList | Under guidance of 1H NMR, ten new polypropionate derivatives, decempyrones A-J (1-10) along with two known analogues (11 and 12), were isolated from the marine-derived fungusFusarium decemcellulare SYSU-MS6716. The planar structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, and HR-ESIMS). The absolute configuration of the chiral centers in the side chain is a major obstacle for the structure identification of natural polypropionate derivatives. Herein, the J-based configurational analysis (JBCA), chemical degradation, geminal proton rule, and the modified Mosher's method were adopted to fix their absolute configurations in the side chain. Compounds 3 and 10 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50values 22.4 ± 1.8 and 21.7 ± 1.1 μM. In addition, compounds 3 and 10 displayed MptpA inhibitory activity with an IC50 value of 19.2 ± 0.9 and 33.1 ± 2.9 µM. Structure-activity relationships of the polypropionate derivatives were discussed.Under guidance of 1H NMR, ten new polypropionate derivatives, decempyrones A-J (1-10) along with two known analogues (11 and 12), were isolated from the marine-derived fungusFusarium decemcellulare SYSU-MS6716. The planar structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, and HR-ESIMS). The absolute configuration of the chiral centers in the side chain is a major obstacle for the structure identification of natural polypropionate derivatives. Herein, the J-based configurational analysis (JBCA), chemical degradation, geminal proton rule, and the modified Mosher's method were adopted to fix their absolute configurations in the side chain. Compounds 3 and 10 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50values 22.4 ± 1.8 and 21.7 ± 1.1 μM. In addition, compounds 3 and 10 displayed MptpA inhibitory activity with an IC50 value of 19.2 ± 0.9 and 33.1 ± 2.9 µM. Structure-activity relationships of the polypropionate derivatives were discussed. Under guidance of H NMR, ten new polypropionate derivatives, decempyrones A-J (1-10) along with two known analogues (11 and 12), were isolated from the marine-derived fungusFusarium decemcellulare SYSU-MS6716. The planar structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, and HR-ESIMS). The absolute configuration of the chiral centers in the side chain is a major obstacle for the structure identification of natural polypropionate derivatives. Herein, the J-based configurational analysis (JBCA), chemical degradation, geminal proton rule, and the modified Mosher's method were adopted to fix their absolute configurations in the side chain. Compounds 3 and 10 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC values 22.4 ± 1.8 and 21.7 ± 1.1 μM. In addition, compounds 3 and 10 displayed MptpA inhibitory activity with an IC value of 19.2 ± 0.9 and 33.1 ± 2.9 µM. Structure-activity relationships of the polypropionate derivatives were discussed. [Display omitted] •Ten new polypropionate derivatives, decempyrones A–J (1–10) were isolated from Fusarium graminearum.•Absolute configurations were fixed by JBCA, chemical degradation, geminal proton rule, and modified Mosher’s method.•Decempyrones C and J exhibited potent anti-inflammatory activity.•Decempyrones C and J also displayed MptpA kinase inhibitory activity. Under guidance of 1H NMR, ten new polypropionate derivatives, decempyrones A–J (1–10) along with two known analogues (11 and 12), were isolated from the marine-derived fungusFusarium decemcellulare SYSU-MS6716. The planar structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, and HR-ESIMS). The absolute configuration of the chiral centers in the side chain is a major obstacle for the structure identification of natural polypropionate derivatives. Herein, the J-based configurational analysis (JBCA), chemical degradation, geminal proton rule, and the modified Mosher’s method were adopted to fix their absolute configurations in the side chain. Compounds 3 and 10 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50values 22.4 ± 1.8 and 21.7 ± 1.1 μM. In addition, compounds 3 and 10 displayed MptpA inhibitory activity with an IC50 value of 19.2 ± 0.9 and 33.1 ± 2.9 µM. Structure-activity relationships of the polypropionate derivatives were discussed. Under guidance of 1H NMR, ten new polypropionate derivatives, decempyrones A-J (1-10) along with two known analogues (11 and 12), were isolated from the marine-derived fungus Fusarium decemcellulare SYSUMS6716. The planar structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, and HR-ESIMS). The absolute configuration of the chiral centers in the side chain is a major obstacle for the structure identification of natural polypropionate derivatives. Herein, the J-based configurational analysis (JBCA), chemical degradation, geminal proton rule, and the modified Mosher's method were adopted to fix their absolute configurations in the side chain. Compounds 3 and 10 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values 22.4 +/- 1.8 and 21.7 +/- 1.1 mu M. In addition, compounds 3 and 10 displayed MptpA inhibitory activity with an IC50 value of 19.2 +/- 0.9 and 33.1 +/- 2.9 mu M. Structure-activity relationships of the polypropionate derivatives were discussed. |
| ArticleNumber | 105156 |
| Author | Chen, Senhua Lu, Yongjun Liu, Lan Wu, Qilin Guo, Heng Li, Jing Chen, Bin Chen, Dongni Jiang, Minghua |
| Author_xml | – sequence: 1 givenname: Heng surname: Guo fullname: Guo, Heng organization: School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China – sequence: 2 givenname: Qilin surname: Wu fullname: Wu, Qilin organization: School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China – sequence: 3 givenname: Dongni surname: Chen fullname: Chen, Dongni organization: School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China – sequence: 4 givenname: Minghua surname: Jiang fullname: Jiang, Minghua organization: School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China – sequence: 5 givenname: Bin surname: Chen fullname: Chen, Bin organization: Southern Laboratory of Ocean Science and Engineering (Guangdong, Zhuhai), Zhuhai 519000, China – sequence: 6 givenname: Yongjun surname: Lu fullname: Lu, Yongjun organization: School of Life Sciences, Sun Yat-sen University, Guangzhou 510275, China – sequence: 7 givenname: Jing surname: Li fullname: Li, Jing organization: School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China – sequence: 8 givenname: Lan surname: Liu fullname: Liu, Lan organization: School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China – sequence: 9 givenname: Senhua surname: Chen fullname: Chen, Senhua email: chensenh@mail.sysu.edu.cn organization: School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China |
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| Keywords | MptpA inhibitor Fusarium Marine fungi Polypropionate Anti-inflammatory MANGROMICINS TYROSINE-PHOSPHATASE B IDENTIFICATION |
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•Ten new polypropionate derivatives, decempyrones A–J (1–10) were isolated from Fusarium graminearum.•Absolute configurations were fixed by... Under guidance of 1H NMR, ten new polypropionate derivatives, decempyrones A-J (1-10) along with two known analogues (11 and 12), were isolated from the... Under guidance of H NMR, ten new polypropionate derivatives, decempyrones A-J (1-10) along with two known analogues (11 and 12), were isolated from the... |
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| SubjectTerms | Animals Anti-inflammatory Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - isolation & purification Anti-Inflammatory Agents - pharmacology Bacterial Proteins - antagonists & inhibitors Bacterial Proteins - metabolism Biochemistry & Molecular Biology Chemistry Chemistry, Organic Fusarium Fusarium - chemistry Fusarium - metabolism Life Sciences & Biomedicine Lipopolysaccharides - pharmacology Macrophages - cytology Macrophages - drug effects Macrophages - metabolism Magnetic Resonance Spectroscopy Marine fungi Mice Molecular Conformation MptpA inhibitor Nitric Oxide - metabolism Physical Sciences Polypropionate Propionates - chemistry Propionates - isolation & purification Propionates - pharmacology Protein Tyrosine Phosphatases - antagonists & inhibitors Protein Tyrosine Phosphatases - metabolism RAW 264.7 Cells Science & Technology |
| Title | Absolute configuration of polypropionate derivatives: Decempyrones A–J and their MptpA inhibition and anti-inflammatory activities |
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