Linderanolides and isolinderanolides, ten butanolides from Lindera glauca

Cytotoxic Constituents from the Leaves of Cinnamomum subavenium

“…Its molecular formula, C 16 H 26 O 3 , was established by HR-FAB-MS. The UV absorption at 228 nm was similar to that of linderanolide B, 10) indicating the presence of b-hydroxy-gmethylene-a,b-unsaturated g-lactone.…”

“…The 1 H-NMR spectrum of 1 was similar to that of linderanolide B, 10) indicating that 1 has the same b-hy- 4) This cis geometry was confirmed in the NOESY spectrum, which showed cross-peaks between H-4 and H-1Ј. The configuration at C-4 in 1 was determined as 4R on the basis of the correlations between the [a] D value [ϩ44.3°(cϭ0.55, CHCl 3 )] and the configuration at C-4 for 3-alkylidene-4-hydroxyl-5-methylenebutanolide derivatives.…”

“…2,3) In continuation of a program studying chemotaxonomy and biologically active components from Formosan Lauraceous plants, [2][3][4][5][6][7][8][9] two new butanolides, namely, subamolide D [(4R,3Z)-4-hydroxy-5-methylene-3-undecylidenedihydrofuran-2-one] (1), and subamolide E [(4R,3E)-4-hydroxy-5-methylene-3-undecylidenedihydrofuran-2-one] (2), and a new secobutanolide, secosubamolide A {methyl[(2E)-2-[(1S)-1-hydroxy-2-oxopropyl]-octadec-2-enoate]} (3), were isolated. Also confirmed were 21 known compounds, including the butanolides linderanolide B 8) and isolinderanolide B 10) ; one ionone, (ϩ)-abscisic acid 11) ; one sesquiterpenoid, caryophyllene oxide 12) ; one triterpenoid, squalene 13) ; six benzenoids, vanillin, 14) vanillic acid, 14) p-hydroxybenzoic acid, 14) p-hydroxybenzaldehyde, 14) syringic acid, 14) and eugenol 15) ; two polyprenols, ficaprenol-10, 16) and ficaprenol-11 16) ; two chlorophylls, pheophytin-a, 17) and aristophyll-C 18) ; four steroids, b-sitosterol, 19) stigmasterol, 19) b-sitosteryl-D-glucoside, 20) and stigmasteryl-D-glucoside 20) ; two aliphatic compounds, palmitic acid 21) and stearic acid 22) were isolated from the leaves of C. subanenium by MeOH extraction. In this paper, we report the structural elucidation of 1-3 and explore the cytotoxic effect of 1 and 2 on human colon cancer cells.…”

“…Subamolide E, a pale yellowish liquid, also had the molecular formula C 16 H-NMR spectrum of 2 was similar to that of isolinderanolide B, 10) indicating that 2 has the same b-hydroxy-g-methylene-a,b-unsaturated g-lactone skeleton and the same E geometry of the trisubstituted double bond [ 29,2007 ascribed to the effect of the carbonyl group of a lactone ring. The position of these groups was established from the HMBC spectrum.…”

Chemical and Cytotoxic Constituents from the Stem of Machilus zuihoensis

“…Other NOE correlations between MeÀC(1') and H b ÀC(3) and H b ÀC(2') were also found. 88 (t, J 6.8), similar to that of the methanolysis product of isolineranolide E [14]. The geometry of the alkene chain of 3 was determined to be the (E) form based on the chemical shifts of HÀC(3) (d 7.08) and HÀC(4) (d 2.35) [14].…”