Cytotoxic sesquiterpenes from Ligularia platyglossa.
Four sesquiterpene lactones including an eremophilenolide dimer, named as biligulaplenolide, 1, 8beta-hydroxy-1-oxo-(14alpha,15alpha eremophil-7(11),9(10)-dien-12,8alpha-olide, 2, 1-hydroxy-2-oxo-(14alpha,15alpha eremophil-1(10),7(11),8(9)-trien-12,8-olide, 3, 4alpha,8beta,9alpha-trihydroxy- 5alphaEta-7(11)-eudesmen-12,8alpha-olide, 4, along with two known ones, 10alpha-hydroxy-1-oxo-eremophil-7(11),8(9)-dien-12,8-olide, 5, and furanoeremophil-1(10)-ene-2,9-dione, 6, were isolated from the underground organs of Ligularia platyglossa (Franch.) Hand.-Mazz. Their structures were elucidated by spectroscopic methods including single-crystal X-ray diffraction analysis (2 and 3). Their in vitro cytotoxicities against seven cancer cell lines (BGC-823, A549, HL-60, B16, SMMC-7721, BEL7402, Hela) were evaluated. Compounds 2, 3, 5 showed cytotoxic activities on HL-60 cancer cells with IC50 in the range of 24.0 to 51.1 microM, whereas compound 3 exhibited only weak cytotoxic activity against the B16, BEL7402 and Hela cancer cells. Flow cytometric analysis indicated that compound 3 induces Hela cells to apoptotic death after 48 h treatment with 0.38 mM of this compound.
Liu
Jian-Qun
JQ
Department of Pharmacognosy, China Pharmaceutical University, No.1 Shen Non Road, Nanjing 210038, Jiangsu Province, PR China.
Zhang
Mian
M
Zhang
Chao-Feng
CF
Qi
Huan-Yang
HY
Bashall
Alan
A
Bligh
S W Annie
SW
Wang
Zheng-Tao
ZT
D017209:Apoptosis / Q000187:drug effects; D019659:Asteraceae / Q000737:chemistry*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000633:toxicity*
D012717:Sesquiterpenes