Coumaronochromones, flavanones, and isoflavones from the twigs and leaves of Erythrina subumbrans inhibit PTP1B and nitric oxide production
文献类型：期刊论文
| 作者 | Liu, Cai-Ying3; Deng, Pan3; Wang, Bin3; Liu, Ai-Hong1; Wang, Meng-Ge4; Li, Song-Wei2; Chen, Li-Li4; Mao, Shui-Chun3 |
| 刊名 | PHYTOCHEMISTRY
 |
| 出版日期 | 2023-02-01 |
| 卷号 | 206页码:12 |
| 关键词 | Erythrina subumbrans Fabaceae Sesquiterpenoids Coumaronochromones Flavanones Isoflavones Nitric oxide production inhibition PTP1B inhibition |
| ISSN号 | 0031-9422 |
| DOI | 10.1016/j.phytochem.2022.113550 |
| 通讯作者 | Mao, Shui-Chun(maoshuichun@ncu.edu.cn) |
| 英文摘要 | A chemical investigation of the twigs and leaves of Erythrina subumbrans led to the isolation and structural elucidation of three coumaronochromones, erythrinasubumbrin A and (+/-)-erythrinasubumbrin B, five preny-lated flavanones, (+/-)-erythrinasubumbrin C and erythrinasubumbrins D-F, and two prenylated isoflavones, (+/-)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone, in addi-tion to 18 known analogues. Two extra cinnamylphenols previously only known as commercial synthetic products were also isolated and elucidated from a natural source for the first time, and assigned the trivial names erythrinasubumbrins G and H. Their structures were characterized by detailed analysis of spectroscopic data, including HRESIMS and 2D NMR. The absolute configurations of the previously undescribed isolates and the known coumaronochromone lupinol C were determined by specific rotation and electronic circular dichroism (ECD) data. All the isolates were evaluated for their inhibitory activities on protein tyrosine phosphatase 1 B (PTP1B) and nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells as well as their cytotoxicity against the HCT116 cell line. The pair of enantiomers, (+)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone and (-)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hy-droxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone, and the known compounds lupinol C, 4'-O-methyl-8-prenylnaringenin, glepidotin B, shuterin, parvisoflavones A, luteone, lupiwighteone, 2,3-dehydrokievitone, 6,8-diprenylgenistein, angustone A, and 2'-O-demethylbidwillol B exhibited different levels of PTP1B inhibi-tory activities with IC50 values ranging from 3.21 to 19.17 mu M, while erythrinasubumbrin A, (-)-eryth-rinasubumbrin B, (+)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone, (-)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isofla-vone, and the known compounds lupinol C, 8-prenylnaringenin, macatrichocarpin A, alpinumisoflavone, and 2'-O-demethylbidwillol B substantially inhibited NO production in BV-2 microglial cells. In addition, 8-prenylnar-ingenin showed weak cytotoxicity with an IC50 value of 9.13 mu M. This is the first report of PTP1B inhibitory activity for a coumaronochromone. |
| WOS关键词 | PRENYLATED FLAVONOIDS ; ABSOLUTE-CONFIGURATION ; CONSTITUENTS ; FRUITS ; BARK ; DIHYDROFLAVONOL ; PHYTOALEXINS ; METABOLITES ; CHIRALITY |
| 资助项目 | National Natural Science Foundation of China ; Natural Science Foundation of Jiangxi Province, China ; State Key Laboratory of Drug Research-SIMM ; [82060633] ; [81860616] ; [21362024] ; [20212ACB206034] ; [20202BAB206084] ; [20181BAB205086] ; [20161BAB205211] ; [SIMM1803KF-01] |
| WOS研究方向 | Biochemistry & Molecular Biology ; Plant Sciences |
| 语种 | 英语 |
| WOS记录号 | WOS:000903504400006 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/303516]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Mao, Shui-Chun |
| 作者单位 | 1.Nanchang Univ, Ctr Anal & Testing, Nanchang 330047, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 3.Nanchang Univ, Sch Pharm, 461 Bayi Rd, Nanchang 330006, Peoples R China 4.Shanghai Univ Tradit Chinese Med, Inst Interdisciplinary Integrat Med Res, Shanghai Frontiers Sci Ctr Chinese Med Chem Biol, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Cai-Ying,Deng, Pan,Wang, Bin,et al. Coumaronochromones, flavanones, and isoflavones from the twigs and leaves of Erythrina subumbrans inhibit PTP1B and nitric oxide production[J]. PHYTOCHEMISTRY,2023,206:12. |
| APA | Liu, Cai-Ying.,Deng, Pan.,Wang, Bin.,Liu, Ai-Hong.,Wang, Meng-Ge.,...&Mao, Shui-Chun.(2023).Coumaronochromones, flavanones, and isoflavones from the twigs and leaves of Erythrina subumbrans inhibit PTP1B and nitric oxide production.PHYTOCHEMISTRY,206,12. |
| MLA | Liu, Cai-Ying,et al."Coumaronochromones, flavanones, and isoflavones from the twigs and leaves of Erythrina subumbrans inhibit PTP1B and nitric oxide production".PHYTOCHEMISTRY 206(2023):12. |
入库方式： OAI收割
来源：上海药物研究所
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