Cytotoxic butanolides and secobutanolides from the stem wood of Formosan Lindera communis.
Bioassay-guided fractionation of the chloroform-soluble fraction from the stem wood of Formosan Lindera communis led to the isolation of two new cytotoxic butanolides, lincomolide C (1), lincomolide D (2), as well as two new secobutanolides, secolincomolide A (3), secolincomolide B (4), together with four known compounds, including one butanolide, isoobtusilactone A (5), and one secobutanolide, secoisolancifolide (6), one sesquiterpene, epi-cubenol (7), one steroid: beta-sitosterol (8). Compound 4 existed in enol [(2E)-2-[(1R)-1-hydroxy-2-oxo-propyl]-6,9-dimethyl-8-hydroxy-hexadec-2,7-dienoic acid methyl ester] (4a) and keto [(2E)-2-[(1R)-1-hydroxy-2-oxo-propyl]-6,9-dimethyl-8-oxo-hexadec-2-enoic acid methyl ester] (4b) tautomers. Compound 2 showed significant cytotoxicity against P-388 and HT-29 cancer cell lines. Also, 2 exhibited marginal activity against A549, 5 against P-388, and 1 against P-388, A549 and HT-29 cancer cell lines. Their structures were determined by spectroscopic analyses.
Tsai
Ian-Lih
IL
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, R.O.C. ialits@kmu.edu.tw
Hung
Chao-Hui
CH
Duh
Chang-Yih
CY
Chen
Ih-Sheng
IS
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001681:Biological Assay; D005227:Fatty Acids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019073:HT29 Cells / Q000187:drug effects; D006801:Humans; D007536:Isomerism; D027443:Lindera; D009682:Magnetic Resonance Spectroscopy; D008516:Medicine, Chinese Traditional; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018547:Plant Stems / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
D005227:Fatty Acids; D005231:Fatty Acids, Unsaturated; D010936:Plant Extracts; C455063:lincomolide C; C455066:lincomolide D; C455064:secolincomolide A; C455065:secolincomolide B; D015107:4-Butyrolactone