Structurally diverse glycosides of secoiridoid, bisiridoid, and triterpene-bisiridoid conjugates from the flower buds of two Caprifoliaceae plants and their ATP-citrate lyase inhibitory activities
文献类型：期刊论文
| 作者 | Wan, Jiang2,3; Jiang, Chun-Xiao2; Tang, Yu3; Ma, Guang-Lei2; Tong, Ying-Peng2; Jin, Ze-Xin2; Zang, Yi1 ; Osman, Ezzat E. A.3,4; Li, Jia1; Xiong, Juan3
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| 刊名 | BIOORGANIC CHEMISTRY
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| 出版日期 | 2022-03-01 |
| 卷号 | 120页码:13 |
| 关键词 | Caprifoliaceae Lonicera japonica Abelia x grandiflora Flower buds Bioassay-guided HPLC-PDA profiling Secoiridoid glycosides Bisiridoid glycosides Triterpene-bisiridoid conjugates ATP-citrate lyase |
| ISSN号 | 0045-2068 |
| DOI | 10.1016/j.bioorg.2022.105630 |
| 通讯作者 | Xiong, Juan(jxiong@fudan.edu.cn) ; Hu, Jin-Feng(jfhu@fudan.edu.cn) |
| 英文摘要 | The ethanolic extracts of the dried flower buds of two Caprifoliaceae plants, Lonicera japonica and Abelia x grandiflora, showed considerable inhibitory activities against adenosine triphosphate (ATP)-citrate lyase (ACL), a new promising drug target for the treatment of metabolic disorders. Bioassay-guided purification in conjunction with HPLC-PDA profiling led to the isolation and characterization of thirty-five (1-35) and fourteen (1'-14') structurally diverse compounds from the above two plant extracts, respectively. Compounds 1-9 and 1'-6'& nbsp;are previously undescribed glycosides. Their structures were elucidated on the basis of spectroscopic data, electronic circular dichroism (ECD), and single crystal X-ray diffraction analyses. In particular, lonicejaposide A (1) has an unprecedented skeleton generated through the coupling of C-7 in secologanin with C-2 " in phenylacetaldehyde via an aldol condensation. Abeliflorosides A (1 & PRIME;) and B (2 & PRIME;) are hitherto unknown glycosides of triterpene and bisiridoid conjugates constructed through the formation of a 1,3-dioxane moiety. All the isolates were evaluated for their inhibitory activities against ACL. Compounds 9, 25-28, 31, 1', 2', and 14'& nbsp;displayed significant inhibitory effects, with IC50 values ranging from 0.1 to 14.2 mu M. The interactions of selected compounds possessing different structure features (e.g., 9, 25, 31, and 2') with ACL were thereafter performed by employing molecular docking studies. In addition, compound 2 & PRIME;, the most complex triterpene-bisiridoid conjugate glycoside reported herein, also inhibited acetyl-CoA carboxylase 1 (ACC1), with an IC50 value of 7.9 mu M. The dried material of the flower buds of L. japonica (honeysuckle) is a well-known traditional oriental medicine (i.e., Flos Lonicerae Japonicae, FLJ) and has long been used in large quantities. The above findings not only provide new insights for the development of multipurpose utilization of FLJ in healthcare community, but also provide profitable clues indicating that the flower buds of A. x grandiflora might be a potential alternative to FLJ in the traditional Chinese medicine market. |
| WOS关键词 | LONICERA-JAPONICA THUNB. ; IRIDOID GLYCOSIDES ; ALPHA-GLUCOSIDASE ; ACID ; CONSTITUENTS ; FLAVONOIDS ; IDENTIFICATION ; DERIVATIVES ; COMPONENTS ; EFFICACY |
| 资助项目 | NSFC[21937002] ; NSFC[81773599] ; NSFC[21772025] ; National Science and Technology Major Project for New Drug Research and Development of MOST[2019ZX09735-002] |
| WOS研究方向 | Biochemistry & Molecular Biology ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000784379000001 |
| 出版者 | ACADEMIC PRESS INC ELSEVIER SCIENCE |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/299764]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Xiong, Juan; Hu, Jin-Feng |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 2.Taizhou Univ, Inst Nat Med & Hlth Prod, Sch Pharmaceut Sci, Zhejiang Prov Key Lab Plant Ecol & Conservat, Taizhou 318000, Zhejiang, Peoples R China 3.Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China 4.Theodor Bilharz Res Inst, Lab Med Chem, Kornaish El Nile St, Giza 12411, Egypt |
| 推荐引用方式 GB/T 7714 | Wan, Jiang,Jiang, Chun-Xiao,Tang, Yu,et al. Structurally diverse glycosides of secoiridoid, bisiridoid, and triterpene-bisiridoid conjugates from the flower buds of two Caprifoliaceae plants and their ATP-citrate lyase inhibitory activities[J]. BIOORGANIC CHEMISTRY,2022,120:13. |
| APA | Wan, Jiang.,Jiang, Chun-Xiao.,Tang, Yu.,Ma, Guang-Lei.,Tong, Ying-Peng.,...&Hu, Jin-Feng.(2022).Structurally diverse glycosides of secoiridoid, bisiridoid, and triterpene-bisiridoid conjugates from the flower buds of two Caprifoliaceae plants and their ATP-citrate lyase inhibitory activities.BIOORGANIC CHEMISTRY,120,13. |
| MLA | Wan, Jiang,et al."Structurally diverse glycosides of secoiridoid, bisiridoid, and triterpene-bisiridoid conjugates from the flower buds of two Caprifoliaceae plants and their ATP-citrate lyase inhibitory activities".BIOORGANIC CHEMISTRY 120(2022):13. |
入库方式： OAI收割
来源：上海药物研究所
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