Absolute structures of monoterpenoids with a δ-lactone-containing skeleton from Ligularia hodgsonii.
Bioactivity-directed fractionation of a methanol extract of Ligularia hodgsonii afforded two new monoterpenoids, liguhodgcins A (1) and B (2), with an unusual δ-lactone-containing skeleton. Moreover, liguhodgcin A (1) contained a chlorine atom. The structures and absolute configurations of the two compounds were elucidated using NMR spectroscopy, X-ray crystallography, ECD data, and computational approaches. A probable biosynthesis pathway to 1 and 2 was also proposed and discussed. The cytotoxicity of compounds 1 and 2 was evaluated against the human leukemia (HL-60), human hepatoma (SMMC-7721), and human cervical carcinoma (HeLa) cell lines.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
Jian-Jun
JJ
Chen
Wen-Xian
WX
Li
Kun
K
Gao
Xiao-Jie
XJ
Jin
Xiao-Jun
XJ
Yao
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018922:HL-60 Cells; D006367:HeLa Cells; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D007783:Lactones; D039821:Monoterpenes; C574816:liguhodgcin A; C574817:liguhodgcin B