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Chemical and Cytotoxic Constituents from the Stem of Machilus zuihoensis
Author(s) -
Cheng MingJen,
Jayaprakasam Bolleddula,
Ishikawa Tsutomu,
Seki Hiroko,
Tsai IanLih,
Wang JehJeng,
Chen IhSheng
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200207)85:7<1909::aid-hlca1909>3.0.co;2-1
Subject(s) - chemistry , stereochemistry , cytotoxicity , sesquiterpene , triol , parthenolide , organic chemistry , in vitro , diol , biochemistry , apoptosis
Five new compounds, including a novel lactone, machilactone (= rel ‐(2 R ,3a R ,6 E ,6a S )‐2‐heptadecyl‐3a‐methyl‐6‐octadecylidene‐6,6a‐dihydrofuro[2,3‐ d ][1,3]dioxol‐5(3a H )‐one; 1 ), a new sesquiterpene, 3,4‐dihydroxy‐ β ‐bisabolol (= rel ‐(1 R ,2 S ,4 R )‐1‐[(1 R )‐1,5‐dimethylhex‐4‐enyl]‐1‐methylcyclohexane‐1,2,4‐triol; 2 ), a new secobutyrolactone, methyl (2 E )‐2‐(1‐hydroxy‐2‐oxopropyl)eicos‐2‐enoate ( 3 ), two new butyrolactones, machicolide A ( 4 ) and machicolide B ( 5 ) (=3 E ,4 R ,5 R )‐ and (3 Z ,4 R ,5 R )‐4,5‐dihydro‐4‐hydroxy‐5‐methoxy‐5‐methyl‐3‐octadecylidenefuran‐2(3 H )‐one, resp.) as a mixture, together with known caryophyllene oxide (=4,12,12‐trimethyl‐9‐methylene‐5‐oxatricyclo[8.2.0.0 4,6 ]dodecane), hexacosane, tetracosanoic acid, isomahubanolide‐23 (=(3 E ,4 R )‐4,5‐dihydro‐4‐hydroxy‐5‐methylidene‐3‐octadecylidenefuran‐2(3 H )‐one), and β ‐bisabolol (=(1 S )‐1‐[(1 S )‐1,5‐dimethylhex‐4‐enyl]‐4‐methylcyclohex‐3‐en‐1‐ol) were isolated from the stem wood of Machilus zuihoensis. The structures of these compounds were established by spectroscopic studies. The eicos‐2‐enoate ( 3 ) and β ‐bisabolol exhibited marginal cytotoxicity against NUGC and HONE‐1 cancer cell lines in vitro.