Hirsutinolide-type sesquiterpenoids with anti-prostate cancer activity from Cyanthillium cinereum

Song Ang; Chun Liu; Peng Hong; Lei Yang; Gui'e Hu; Xi Zheng; Jingwei Jin; Rihui Wu; Wing-Leung Wong; Kun Zhang; Lishe Gan; Dongli Li

doi:10.1016/j.phytochem.2023.113887

Hirsutinolide-type sesquiterpenoids with anti-prostate cancer activity from Cyanthillium cinereum

Phytochemistry. 2023 Dec:216:113887. doi: 10.1016/j.phytochem.2023.113887. Epub 2023 Oct 6.

Authors

Song Ang¹, Chun Liu², Peng Hong³, Lei Yang³, Gui'e Hu², Xi Zheng³, Jingwei Jin³, Rihui Wu³, Wing-Leung Wong², Kun Zhang¹, Lishe Gan⁴, Dongli Li⁵

Affiliations

¹ School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020, China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, China; Guangdong University of Technology, Guangzhou, 510006, China.
² School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020, China.
³ School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020, China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, China.
⁴ School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020, China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, China. Electronic address: ganlishe@163.com.
⁵ School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020, China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, China; Guangdong Provincial Key Laboratory of Large Animal Models for Biomedicine, Wuyi University, Jiangmen, 529020, China. Electronic address: wyuchemldl@126.com.

PMID: 37806467
DOI: 10.1016/j.phytochem.2023.113887

Abstract

Four previously undescribed hirsutinolide-type sesquiterpenoids, cyanolides A-D (1-4), along with twelve known analogues (5-16), were isolated from the aerial parts of Cyanthillium cinereum. Their structures were determined by comprehensive analysis of NMR, HRESIMS, and ECD spectra. Compound 1 is a rarely occurring hirsutinolide-type sesquiterpenoid with 1,4-ether ring ruptured and containing a chlorine atom, and compounds 13-16 were reported from this plant for the first time. All compounds were tested for their inhibiting effects on prostate cancer cells. As a result, compounds 1, 3, and 8-14 exhibited significant anti-prostate cancer activity against PC-3 and LNCaP cells with IC₅₀ values ranging from 2.2 ± 0.4 to 8.5 ± 0.7 μM and 3.0 ± 0.7 to 10.5 ± 1.1 μM, respectively. The preliminary structure-activity relationship was discussed. Further investigation showed that compound 1 induced apoptosis in PC-3 cells.

Keywords: Anti-prostate cancer activity; Cyanthillium cinereum (L.) (Asteraceae); Hirsutinolide-type sesquiterpenoid.

MeSH terms

Asteraceae* / chemistry
Humans
Male
Molecular Structure
Prostatic Neoplasms* / drug therapy
Sesquiterpenes* / chemistry
Sesquiterpenes* / pharmacology
Structure-Activity Relationship

Substances

Sesquiterpenes