Discovery of isopentenyl flavonoids with inhibitory activity against hepatocellular carcinoma cells based on DeepSAT

被引：0
作者：
Wang, Qing [1 ,2 ,3 ,4 ]
Xin, Ben-Song [1 ,2 ,3 ,4 ]
Kou, Wen-Long [1 ,2 ,3 ,4 ]
Gao, Li-Na [1 ,2 ,3 ,4 ]
Zhang, Gu-Xue [1 ,2 ,3 ,4 ]
Qiao, Yan-Jiao [1 ,2 ,3 ,4 ]
Yao, Guo-Dong [1 ,2 ,3 ,4 ]
Huang, Xiao-Xiao [1 ,2 ,3 ,4 ,5 ]
Song, Shao-Jiang [1 ,2 ,3 ,4 ]
机构：
[1] Key Lab Computat Chem Based Nat Antitumor Drug Res, Shenyang, Liaoning, Peoples R China
[2] Engn Res Ctr Nat Med Act Mol Res & Dev, Shenyang, Liaoning, Peoples R China
[3] Key Lab Nat Bioact Cpds Discovery & Modificat, Shenyang, Peoples R China
[4] Shenyang Pharmaceut Univ, Sch Tradit Chinese Mat Med, Shenyang 110016, Liaoning, Peoples R China
[5] Yantai Univ, Basic Sci Res Ctr Base Pharmaceut Sci, Yantai 264005, Shandong, Peoples R China
来源：
PHYTOCHEMISTRY | 2025年 / 234卷
关键词：
Daphne giraldii; Thymelaeaceae; Isopentenyl flavonoids; Chiral resolution; HepG2; Hep3B; DAPHNE-GIRALDII; IDENTIFICATION; ASSIGNMENT; COMPONENTS; APOPTOSIS; ROOT;
D O I：
10.1016/j.phytochem.2025.114437
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Isopentenyl flavonoids were isolated from Daphne giraldii Nitsche and their pharmacological activity was further studied to enrich its chemical composition. Seventeen isopentenyl flavonoids (1a/1b-3a/3b and 4-14), including thirteen undescribed compounds (1a/1b-3a/3b and 4-10), were obtained from D. giraldii under the guidance of HSQC-based DeepSAT. Their structures and configurations were established by comprehensive spectroscopic analysis, ECD, and GFN2NMR methods. Moreover, all compounds were evaluated for potential cytotoxicity against hepatocellular carcinoma HepG2 and Hep3B cell lines. Among them, undescribed compound 3 exhibited potent growth-inhibitory activities against HepG2 and Hep3B cells due to the presence of a unique isopentene group and pyran ring structure, with half-maximal inhibitory concentration values of IC50 = 17.55 +/- 1.65 mu M and IC50 = 1.12 +/- 0.08 mu M, respectively. Morphological and staining analyses suggested compound 11 induced apoptosis in HepG2 and Hep3B cells, indicating that the isopentene group at the C-8 position was the active group.
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页数：12
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  • [1] Ai W.-J., Li J., Cao D.-S., Liu S., Yuan Y.-Y., Li Y., Tan G.-S., Xu K.-P., Yu X., Kang F.-H., Zou Z.-X., Wang W.-X., A very deep graph convolutional network for <sup>13</sup>C NMR chemical shift calculations with density functional theory level performance for structure assignment, J. Nat. Prod., 87, 4, pp. 743-752, (2024)
  • [2] Bai M., Chen J.-J., Xu W., Elephantopinolide A-P, germacrane-type sesquiterpene lactones from Elephantopus scaber induce apoptosis, autophagy and G2/M phase arrest in hepatocellular carcinoma cells, Eur. J. Med. Chem., 198, (2020)
  • [3] Bai M., Xu W., Zhang X., Li Q., Du N.-N., Liu D.-F., Yao G.-D., Lin B., Song S.-J., Huang X.-X., HSQC-based small molecule accurate recognition technology discovery of diverse cytotoxic sesquiterpenoids from Elephantopus tomentosus L. and structural revision of molephantins A and B, Phytochemistry, 206, (2023)
  • [4] Bailly C., A systematic review of spirostanol saponins and anticancer natural products isolated from Tacca plantaginea (Hance) Drenth, Phytochemistry, 228, (2024)
  • [5] Basu S., Ganguly S., Mukhopadhyay S., DeepSat-A learning framework for satellite imagery, CoRR, 15, 9, (2015)
  • [6] Chen X.-C., Li L., Zhang M.-X., Yang J., Lyu C.-M., Xu Y.-Z., Yang Y., Wang Y., Guidelines for application of high-content screening in traditional Chinese medicine: concept, equipment, and troubleshooting, AHM, 4, 1, pp. 1-15, (2024)
  • [7] Dong S.-H., Han J.-L., Chang X.-Y., Lian M.-Y., Zhang X., Liu X.-L., Bai M., Huang X.-X., Song S.-J., Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy, Org. Chem. Front., 10, 19, (2023)
  • [8] Dong S.-H., Duan Z.-K., Bai M., Huang X.-X., Song S.-J., Advanced technologies targeting isolation and characterization of natural products, Trends Anal. Chem., 175, (2024)
  • [9] Du Y.-Q., Bai M., Yu X.-Q., Quassinoids from the root barks of Ailanthus altissima: isolation, configurational assignment, and cytotoxic activities, Chin. J. Chem., 39, pp. 879-886, (2020)
  • [10] Duan K.-Z., Wang X., Lian Y.-M., Bioassay-guided and DeepSAT-driven precise mining of monoterpenoid coumarin derivatives with antifeedant effects from the leaves of Ailanthus altissima, J. Agric. Food Chem., (2024)
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