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PC-33

Bioactivity-guided isolation and anti-inflammatory evaluation of secondary

metabolites from Syzygium simile stems

1
1
#,1
Shih-Yu Wang, Ju-Hsin Cheng, Tsong-Long Hwang, Ho-Cheng Wu, Chia-Hung
2
5
Yen, 3,4 Hsueh-Wei Chang, Hsun-Shuo Chang* ,1,3,4

1 School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807378, Taiwan
2 Chang Gung University of Science and Technology, Taoyuan 333323, Taiwan
3 Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807378,
Taiwan
4 Drug Development and Value Creation Research Center, Kaohsiung Medical University,
Kaohsiung 807378, Taiwan
5 Department of Biomedical Science and Environmental Biology, Kaohsiung Medical
University, Kaohsiung 807378, Taiwan
* E-mail: hschang@kmu.edu.tw

Abstract
Syzygium simile (Myrtaceae) is an evergreen small tree endemic to Taiwan, primarily
distributed on Lanyu (Orchid Island). This species is characterized by opposite leaves and small
white blossoms. In our preliminary screening, the EtOAc layer extracted from S. simile stems
demonstrated significant anti-inflammatory, anti-liver cancer, and anti-triple-negative breast
cancer activities. While previous research has focused exclusively on leaf constituents and their
biological properties, the stems and other plant parts have remained uninvestigated. Given the
limited research on S. simile and our promising preliminary results, a comprehensive
investigation of S. simile stem constituents was warranted. Through bioactivity-guided
molecular networking approaches, secondary metabolites from the EtOAc layer of S. simile
stem demonstrated anti-inflammatory properties by suppressing superoxide anion production
and elastase release. Bioassay-guided separation yielded 24 compounds: fifteen triterpenoids
(1-15), two steroids (16 and 17), three lignanoids (18-20), two benzenoids (21 and 22), one
apocarotenoid (23), and one coumarin (24). Specifically, compounds 1, 4, 6, 10, 16, and 18
exhibited significant inhibition of superoxide anion generation (inhibition rates ranging from
77.36 ± 5.70% to 100.79 ± 0.74%), while 1, 4, 8, 10 and 14 showed inhibition of elastase release
(inhibition rates ranging from 86.34 ± 3.95% to 108.67 ± 6.74%). It is worth mentioning that
compounds 1, 4, and 10 showed dual inhibitory effects against both inflammatory targets, with
even stronger inhibition than the positive control. These findings comprehensively investigate
the chemical composition and anti-inflammatory activities of S. simile stems, while
simultaneously revealing the drug development potential of Taiwan's endemic botanical
resources.

Keywords: Myrtaceae; Syzygium simile; Anti-inflammatory activity; Cytotoxicity