Design, synthesis and biological evaluation of new ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) derivatives as potential antitumor agents

Chenliang Zhao; Yinxiao Du; Yixuan Xia; Baisen Chen; Zhongyi Seng; Kanglun Liu; Chushing Lam; Juan Zou; Hongjie Zhang

doi:10.1016/j.bmc.2026.118568

Design, synthesis and biological evaluation of new ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) derivatives as potential antitumor agents

Chenliang Zhao
, Yinxiao Du
, Yixuan Xia
, Baisen Chen
, Zhongyi Seng
, Kanglun Liu
, Chushing Lam
, Juan Zou^*
, Hongjie Zhang^*

^*Corresponding author for this work

Chinese Medicine - Teaching and Research Division

Research output: Contribution to journal › Journal article › peer-review

Abstract

AbstractEnt-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) is a naturally occurring ent-kaurane diterpenoid isolated from the traditional Chinese herbal medicine Pteris semipinnata L., a fern plant known for its reported antitumor properties. In an effort to expand the pool of natural scaffold-based compounds for anticancer purposes, novel derivatives of 5F have been synthesized by modifying functional groups at C-11 and C-19. These derivatives have been evaluated for their anti-proliferative activities against a panel of cancer cell lines. Among them, compound 13 exhibited approximately 27 times greater potency than 5F in HCT116 cells, with an IC ₅₀ value of 0.232 μM. In an HCT116 xenograft mouse model, 13 displayed superior tumor inhibitory effects compared to fluorouracil (5-FU).

Original language	English
Article number	118568
Number of pages	16
Journal	Bioorganic and Medicinal Chemistry
Volume	135
DOIs	https://doi.org/10.1016/j.bmc.2026.118568
Publication status	Published - Apr 2026

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This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

User-Defined Keywords

5F ent-kaurene diterpene
5F derivatives
Cytotoxicity
In vivo antitumor activity
HCT116 mouse model

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10.1016/j.bmc.2026.118568

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@article{8b9d332e0355477abfd2945538bf5f63,

title = "Design, synthesis and biological evaluation of new ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) derivatives as potential antitumor agents",

abstract = "AbstractEnt-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) is a naturally occurring ent-kaurane diterpenoid isolated from the traditional Chinese herbal medicine Pteris semipinnata L., a fern plant known for its reported antitumor properties. In an effort to expand the pool of natural scaffold-based compounds for anticancer purposes, novel derivatives of 5F have been synthesized by modifying functional groups at C-11 and C-19. These derivatives have been evaluated for their anti-proliferative activities against a panel of cancer cell lines. Among them, compound 13 exhibited approximately 27 times greater potency than 5F in HCT116 cells, with an IC 50 value of 0.232 μM. In an HCT116 xenograft mouse model, 13 displayed superior tumor inhibitory effects compared to fluorouracil (5-FU).",

keywords = "5F ent-kaurene diterpene, 5F derivatives, Cytotoxicity, In vivo antitumor activity, HCT116 mouse model",

author = "Chenliang Zhao and Yinxiao Du and Yixuan Xia and Baisen Chen and Zhongyi Seng and Kanglun Liu and Chushing Lam and Juan Zou and Hongjie Zhang",

note = "Publisher Copyright: {\textcopyright} 2026 Elsevier Ltd. Funding Information: This study was funded by the Research Grant Council of the Hong Kong Special Administrative Region, China (Project no. HKBU 12102219), University Grants Committee of the Hong Kong Special Administrative Region, China (UGC Research Matching Grant Scheme RMGS2019\_1\_19), Department of Education of Guizhou Province Higher Education Institution Natural Science Research Program, Qianjiaoji [No (2024)115], Natural-Scientific Research Program of Department of Education of Guizhou Province, Qianjiaoji [No (2023)070], the Doctoral Initiation Fund of Guizhou University of Traditional Chinese Medicine, grant number [2023]35, and 2023 Guizhou university of traditional Chinese medicine Xueshu Xinmiao project (Gui Ke He Xue Shu Xin Miao [2023]-11).",

year = "2026",

month = apr,

doi = "10.1016/j.bmc.2026.118568",

language = "English",

volume = "135",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - Design, synthesis and biological evaluation of new ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) derivatives as potential antitumor agents

AU - Zhao, Chenliang

AU - Du, Yinxiao

AU - Xia, Yixuan

AU - Chen, Baisen

AU - Seng, Zhongyi

AU - Liu, Kanglun

AU - Lam, Chushing

AU - Zou, Juan

AU - Zhang, Hongjie

N1 - Publisher Copyright: © 2026 Elsevier Ltd. Funding Information: This study was funded by the Research Grant Council of the Hong Kong Special Administrative Region, China (Project no. HKBU 12102219), University Grants Committee of the Hong Kong Special Administrative Region, China (UGC Research Matching Grant Scheme RMGS2019_1_19), Department of Education of Guizhou Province Higher Education Institution Natural Science Research Program, Qianjiaoji [No (2024)115], Natural-Scientific Research Program of Department of Education of Guizhou Province, Qianjiaoji [No (2023)070], the Doctoral Initiation Fund of Guizhou University of Traditional Chinese Medicine, grant number [2023]35, and 2023 Guizhou university of traditional Chinese medicine Xueshu Xinmiao project (Gui Ke He Xue Shu Xin Miao [2023]-11).

PY - 2026/4

Y1 - 2026/4

N2 - AbstractEnt-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) is a naturally occurring ent-kaurane diterpenoid isolated from the traditional Chinese herbal medicine Pteris semipinnata L., a fern plant known for its reported antitumor properties. In an effort to expand the pool of natural scaffold-based compounds for anticancer purposes, novel derivatives of 5F have been synthesized by modifying functional groups at C-11 and C-19. These derivatives have been evaluated for their anti-proliferative activities against a panel of cancer cell lines. Among them, compound 13 exhibited approximately 27 times greater potency than 5F in HCT116 cells, with an IC 50 value of 0.232 μM. In an HCT116 xenograft mouse model, 13 displayed superior tumor inhibitory effects compared to fluorouracil (5-FU).

AB - AbstractEnt-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) is a naturally occurring ent-kaurane diterpenoid isolated from the traditional Chinese herbal medicine Pteris semipinnata L., a fern plant known for its reported antitumor properties. In an effort to expand the pool of natural scaffold-based compounds for anticancer purposes, novel derivatives of 5F have been synthesized by modifying functional groups at C-11 and C-19. These derivatives have been evaluated for their anti-proliferative activities against a panel of cancer cell lines. Among them, compound 13 exhibited approximately 27 times greater potency than 5F in HCT116 cells, with an IC 50 value of 0.232 μM. In an HCT116 xenograft mouse model, 13 displayed superior tumor inhibitory effects compared to fluorouracil (5-FU).

KW - 5F ent-kaurene diterpene

KW - 5F derivatives

KW - Cytotoxicity

KW - In vivo antitumor activity

KW - HCT116 mouse model

UR - https://www.scopus.com/pages/publications/105030309093

U2 - 10.1016/j.bmc.2026.118568

DO - 10.1016/j.bmc.2026.118568

M3 - Journal article

C2 - 41570530

AN - SCOPUS:105030309093

SN - 0968-0896

VL - 135

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

M1 - 118568

ER -

Design, synthesis and biological evaluation of new ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F) derivatives as potential antitumor agents

Abstract

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