Prenylated C6-C3 compounds with molecular diversity from the roots of Illicium oligandrum.
Eleven prenylated C(6)-C(3) compounds, illioliganpyranone A (1), illioliganfunone A-D (2-5), and illioliganone D-I (6-11), together with five known prenylated C(6)-C(3) compounds (12-16), were isolated from roots of Illicium oligandrum. The structures of 1-11 were elucidated by spectroscopic methods including 1D and 2D NMR, HRESIMS, and CD experiments. Possible biosynthetic pathways to compounds 1-16 derived from a common precursor of 5-allylbenzene-1,2,4-triol were postulated. All compounds were evaluated for cytotoxic activities against five human cancer cell lines (HCT-8, Bel-7402, BGC-823, A549 and A2780). Compound 15 exhibited significant cytotoxicity against HCT-8, BGC-823, A549, and A2780 cell lines with IC(50) values of 0.30-2.57 μM. Compound 16 showed moderate selective cytotoxicity against sensitive A2780 cells with IC(50) value of 1.38 μM.
Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, People's Republic of China.
Shuang-Gang
SG
Ma
Wen-Zhao
WZ
Tang
Yu-Xi
YX
Liu
You-Cai
YC
Hu
Shi-Shan
SS
Yu
Yi
Y
Zhang
Xiao-Guang
XG
Chen
Jing
J
Qu
Jin-Hong
JH
Ren
Yun-Bao
YB
Liu
Song
S
Xu
Jing
J
Liu
Yuan-Yan
YY
Liu
Yong
Y
Li
Hai-Ning
HN
Lü
Xian-Fu
XF
Wu
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D052117:Benzodioxoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D029523:Illicium / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D054876:Prenylation
C555902:(2S,4S)-illicinone D; D000972:Antineoplastic Agents, Phytogenic; D052117:Benzodioxoles; D004365:Drugs, Chinese Herbal