Guided Isolation of Isopentenyl Flavonoids from Daphne giraldii Based on the Combination of GNPS and SMART

Bo-Yuan Zhao; Ben-Song Xin; Shuang Qiu; Guo‐Dong Yao; Xiao‐Xiao Huang; Shao‐Jiang Song

doi:10.1248/cpb.c24-00462

Current Topics: Regular Article

Guided Isolation of Isopentenyl Flavonoids from Daphne giraldii Based on the Combination of GNPS and SMART

Bo-Yuan Zhao ^†, Ben-Song Xin ^†, Shuang Qiu, Guo‐Dong Yao, Xiao‐Xiao Huang , Shao‐Jiang Song

Author information

Bo-Yuan Zhao ^†
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China
Ben-Song Xin ^†
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China
Shuang Qiu
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China
Guo‐Dong Yao
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China
Xiao‐Xiao Huang Corresponding author
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China
Basic Science Research Center Base (Pharmaceutical Science), Yantai University, Yantai, Shandong, 264005, China
Shao‐Jiang Song Corresponding author
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China
Author contributions

†These authors contributed equally: Bo-Yuan Zhao, Ben-Song Xin

Keywords: Daphne giraldii, isopentenyl flavonoid, molecular networking-guided, cytotoxic activity

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Supplementary material

2025 Volume 73 Issue 3 Pages 189-194

DOI https://doi.org/10.1248/cpb.c24-00462

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Abstract

Six flavonoids (1–6), including 3 previously undescribed compounds (1–3), were isolated from the dried roots and stem skins of Daphne giraldii Nitsche. The strategy of LC-tandem mass spectrometry-based Global Natural Products Social Molecular Networking (GNPS) molecular network technology and NMR-based Small Molecule Accurate Recognition Technology (SMART) technology facilitated the precise separation of isopentenyl flavonoids in D. giraldii. The structures were determined through comprehensive spectroscopic analysis. Furthermore, all compounds were evaluated for their cytotoxic activity against Hep3B cells. Specifically, compounds 1 and 3 exhibited significant cytotoxicity with IC₅₀ values of 5.52 ± 0.57 and 2.53 ± 0.49 μM, respectively, compared to the positive control sorafenib (IC₅₀ = 7.08 ± 0.23 μM).

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