Phytochemical and biological studies on rare and endangered plants endemic to China. Part XLIV. Integrated NMR/EI-MS/LC-PDA-ESIMS approach for dereplication and targeted isolation of fortunefuroic acids from Keteleeria fortunei across diverse geographical origins
文献类型：期刊论文
| 作者 | Zhao, Ze-Yu1,2; Jiang, Zhe-Lu1; Tong, Ying-Peng1; Chi, Chun-Jing1; Zang, Yi3 ; Choo, Yeun-Mun4; Xiong, Juan2; Li, Jia3; Hu, Jin-Feng1,2
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| 刊名 | PHYTOCHEMISTRY
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| 出版日期 | 2025-07-01 |
| 卷号 | 235页码:13 |
| 关键词 | Keteleeria fortunei Pinaceae Geographical origins Integrated NMR/EI-MS/LC-PDA-ESIMS methods Fortunefuroic acids ATP-Citrate lyase |
| ISSN号 | 0031-9422 |
| DOI | 10.1016/j.phytochem.2025.114453 |
| 英文摘要 | Secondary metabolites in plants of the same species, though originating from distinct geographical regions, frequently display both similarities and notable variations. A prior study on the vulnerable Chinese endemic conifer Keteleeria fortunei, collected from Yunnan province (KFYN), led to the isolation of fortunefuroic acids (FFAs) A-I. These compounds represent a unique class of triterpenoids characterized by a rare furoic acid moiety within the lateral chain. The distinct 23,27-epoxy-23,25(27)-dien-26-oic acid unit present in FFAs can be readily identified by characteristic proton NMR signals (6H-24: ca 6.36 ppm; 6H-27: ca 7.97 ppm), a prominent ion fragment at m/z 125 in the EI-MS, and typical UV absorption peak around )max 245 nm. In this study, an integrated approach was employed to dereplicate and isolate FFA-type compounds from K. fortunei collected from Fujian Province (KFFJ). This approach combined NMR, EI-MS, and LC-PDA-ESIMS data to detect and analyze compounds with molecular weights in the range of 464-468 Da, a distinguishing feature of FFA-type compounds. Consequently, six previously undescribed FFAs K-P (1-6) were obtained, alongside the re-isolation of FFAs A-D and H. Compound 1 exhibits a rare 17,14-friedo-cyclaorane type skeleton, while compound 2 is characterized as a 3,4-seco-cyclaorane-3,26-dioic acid. Compounds 3-6 are identified as derivatives of 9 beta H-lanost-26-oic FFAs. Additionally, a previously unreported lanost-26-oic acid derivative (7) was also identified, exhibiting an inhibitory effect on ATP-citrate lyase. Their chemical structures and absolute configurations were determined through spectroscopic analysis, GIAO NMR calculations combined with DP4+ probability analyses, and electronic circular dichroism calculations. The isolated FFAs have the potential to serve as chemotaxonomic markers for the genus Keteleeria within the Pinaceae family. This study marks the first application of integrated NMR/EIMS/LC-PDA-ESIMS methods for both dereplication and the discovery of new natural products. Notably, the KFFJ samples were collected from a location approximately 1500 km away from that of KFYN. Understanding the impact of geographical origins on specialized metabolites may provide valuable insights into the sustainable utilization and conservation of endangered plant species. |
| WOS关键词 | AUSTRALIAN SOFT CORALS ; SHED TRUNK BARKS ; SINULARIA ; TRITERPENOIDS ; METABOLITES ; MECHANISMS |
| 资助项目 | NSFC[21937002] ; NSFC[81773599] ; Zhejiang Provincial Natural Science Foundation of China[LY23H300001] |
| WOS研究方向 | Biochemistry & Molecular Biology ; Plant Sciences |
| 语种 | 英语 |
| WOS记录号 | WOS:001438315200001 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/316517]  |
| 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.Taizhou Univ, Inst Nat Med & Hlth Prod, Sch Pharmaceut Sci, Zhejiang Prov Key Lab Plant Evolutionary Ecol & Co, Taizhou 318000, Zhejiang, Peoples R China 2.Fudan Univ, Sch Pharm, Dept Nat Med, Shanghai 201203, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 4.Univ Malaya, Fac Sci, Dept Chem, Kuala Lumpur 50603, Malaysia |
| 推荐引用方式 GB/T 7714 | Zhao, Ze-Yu,Jiang, Zhe-Lu,Tong, Ying-Peng,et al. Phytochemical and biological studies on rare and endangered plants endemic to China. Part XLIV. Integrated NMR/EI-MS/LC-PDA-ESIMS approach for dereplication and targeted isolation of fortunefuroic acids from Keteleeria fortunei across diverse geographical origins[J]. PHYTOCHEMISTRY,2025,235:13. |
| APA | Zhao, Ze-Yu.,Jiang, Zhe-Lu.,Tong, Ying-Peng.,Chi, Chun-Jing.,Zang, Yi.,...&Hu, Jin-Feng.(2025).Phytochemical and biological studies on rare and endangered plants endemic to China. Part XLIV. Integrated NMR/EI-MS/LC-PDA-ESIMS approach for dereplication and targeted isolation of fortunefuroic acids from Keteleeria fortunei across diverse geographical origins.PHYTOCHEMISTRY,235,13. |
| MLA | Zhao, Ze-Yu,et al."Phytochemical and biological studies on rare and endangered plants endemic to China. Part XLIV. Integrated NMR/EI-MS/LC-PDA-ESIMS approach for dereplication and targeted isolation of fortunefuroic acids from Keteleeria fortunei across diverse geographical origins".PHYTOCHEMISTRY 235(2025):13. |
入库方式： OAI收割
来源：上海药物研究所
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