Convenient synthesis of optically active abscisic acid and xanthoxin

Cytotoxic Constituents from the Leaves of Cinnamomum subavenium

“…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.…”

Constituents of the Fruits of Citrus medica L. var. sarcodactylis and the Effect of 6,7-Dimethoxy-coumarin on Superoxide Anion Formation and Elastase Release

“…According to the chemical shifts and the degree of unsaturation, it also suggested the presence of an epoxide ring at C-1′ and C-2′, and a hydroxyl group connected at C-4′, and these were further confirmed with the 2D spectroscopic analytical data. Thus, the structure of 1 was similar to abscisic acid (ABA) and xanthoxin in the phytohormone, which played the key role in biotic and abiotic stress responses [ 51 ]. The relative stereochemistry was confirmed by a NOESY experiment, which showed correlations of CH 3 -8′/CH 3 -7′, H-4′/H-9′, H-3′ (δ 1.73)/H-5, and H-3′ (δ 1.73)/CH 3 -7′, respectively ( Figure 3 ).…”

(E)-4-(2-Chloro-1-hydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one

“…E68, o3485 [doi:10.1107/S1600536812048544] (E)-4-(2-Chloro-1-hydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one Shan Liu, Xiao-Yan Yang and Yu-Ling Zhang S1. Comment (E)-4-(2-Chloro-1-hydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one is an important intermediate used to synthesize abscisic acid (ABA), which has important activities as a plant hormone (Sakai, et al, 1992). We report here the crystal structure of the title compound (Fig.…”