TY - JOUR
T1 - Hirsutinolide-type sesquiterpenoids with anti-prostate cancer activity from Cyanthillium cinereum
AU - Ang, Song
AU - Liu, Chun
AU - Hong, Peng
AU - Yang, Lei
AU - Hu, Gui'e
AU - Zheng, Xi
AU - Jin, Jingwei
AU - Wu, Rihui
AU - Wong, Wing Leung
AU - Zhang, Kun
AU - Gan, Lishe
AU - Li, Dongli
N1 - Publisher Copyright:
© 2023
PY - 2023/12
Y1 - 2023/12
N2 - 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.
AB - 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.
KW - Anti-prostate cancer activity
KW - Cyanthillium cinereum (L.) (Asteraceae)
KW - Hirsutinolide-type sesquiterpenoid
UR - http://www.scopus.com/inward/record.url?scp=85173773696&partnerID=8YFLogxK
U2 - 10.1016/j.phytochem.2023.113887
DO - 10.1016/j.phytochem.2023.113887
M3 - Journal article
C2 - 37806467
AN - SCOPUS:85173773696
SN - 0031-9422
VL - 216
JO - Phytochemistry
JF - Phytochemistry
M1 - 113887
ER -