Identification and bioactivity evaluation of miliusanes from Miliusa sinensis

Wen-Jian Xie, Xin-Ya Xu, Yi-Xuan Xia, Chu Shing Lam, Tie Chen, Yun-Shi Zhi, Kuan Ming Lee, Xun Song, Stephen T. Deyrup*, Zhen-Dan He*, Hong-Jie Zhang*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review


Miliusanes are a class of anticancer lead molecules belonging to meroterpenoids with an 18-carbon skeleton isolated from Miliusa plants. A phytochemical study of the plant M. sinensis was carried out to discover new miliusanes with diverse structural features in order to better understand their structure-activity relationship. As a result, 20 compounds including 12 new ones (7–14 and 17–20) belonging to two sub-classes of miliusanes were isolated and identified from the twigs and leaves of this plant. Their structures, including absolute configurations, were determined by spectroscopic analyses and electronic circular dichroism. The absolute stereochemistry of miliusane structures has also been confirmed for the first time through the single crystal X-ray diffraction analysis of miliusol (1). Bioactivity evaluation showed that some of the miliusane isolates potently inhibit cell growth of several human derived cancer cell lines with IC50 values ranging from 0.52 to 23.5 μM. Compound 11 demonstrated more potent cytotoxic activity than the known miliusol (1) in stomach cancer cells though its structure contains an unconjugated 1, 4-diketone system, which added a new structure-activity feature to miliusanes. The preliminary mechanism of action studies revealed that they could be a class of dual cell migration inhibitor and senescence inducer.

Original languageEnglish
Article number106797
Number of pages13
JournalBioorganic Chemistry
Early online date24 Aug 2023
Publication statusPublished - Nov 2023

Scopus Subject Areas

  • Organic Chemistry
  • Drug Discovery
  • Molecular Biology
  • Biochemistry

User-Defined Keywords

  • Cytotoxicity
  • Meroterpenoids
  • Miliusa sinensis
  • Miliusanes
  • Plant natural products


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