Novel synthesis of degradation products of carotenoids, megastigmatrienone analogues and blumenol-A

Constituents from Vigna vexillata and Their Anti-Inflammatory Activity

“…With the assistance of a combination of conventional chromatographic techniques, one new sterol ( 1 ) and two new isoflavones ( 2,3 ) were determined by the 1D and 2D NMR elucidations, and mass spectral analyses. In addition, 37 known compounds, including stigmast-4-en-3-one ( 4 ), stigmast-4,22-dien-3-one ( 5 ) [24], (27 RS )-cycloart-28-en-3β,27-diol ( 6 ) [25], β-sitosterol ( 7 ), stigmasterol ( 8 ) [26], sitosterol cis - p -coumarate ( 9 ) [8], sitosterol trans - p -coumarate ( 10 ) [8], lupeol ( 11 ) [26], 6β-hydroxy-β-sitosterone ( 12 ) [27], sitosterol ferulate ( 13 ) [28], (20 R )-22 E -cholest-4-ene-3,6-dione ( 14 ) [29], methylparaben ( 15 ) [30], p -hydroxybenzoic acid ( 16 ) [30], p -hydroxybenzaldehyde ( 17 ) [30], vanillic acid ( 18 ) [30], genistein ( 19 ) [31], dehydrovomifoliol ( 20 ) [32], β-sitostenone ( 21 ) [33], 5,7,4′-trihydroxy-3′-methoxy isoflavone ( 22 ) [34], daidzein ( 23 ) [35], indole-3-carboxaldehyde ( 24 ) [36], abscisic acid ( 25 ) [37], trans -cinnamic acid ( 26 ) [38], β-sitosteryl-3- O -β-glucopyranoside ( 27 ) [39], trans -methyl p -coumarate ( 28 ) [30], salicylic acid ( 29 ) [40], tachioside ( 30 ) [41], 3-hydroxy-β-damascone ( 31 ) [42], p -hydroxyl phenethanol ( 32 ) [43], trans-p -coumaric acid ( 33 ) [44], 3,6-dihydroxy-5,6-dihydro-β-ionol ( 34 ) [45], dihydrophaseic acid ( 35 ) [46], blumenol A ( 36 ) [47], isovitexin ( 37 ) [48], daidzin ( 38 ) [49], vitexin ( 39 ) [50], and quercetin ( 40 ) [51] were characterized by comparison of their physical and spectroscopic data with those reported in the literature.…”

Synthesis of Optically Active Vomifoliol and Roseoside Stereoisomers

“…Synthesis of Vomifoliol Stereoisomers 1-4 Although vomifoliol has been prepared [12][13][14][15] as a diastereomeric mixture, there has been no stereocontrolled synthesis reported so far for the optically active one. In order to synthesize diastereomeric pure vomifoliols 1-4 (Chart 2), intermediate allylic alcohols 12a and 12b were respectively prepared by reduction of previously prepared diastereomeric pure aacetylenic alcohols 11a and 11b 9,10) with LiAlH 4 as shown in Chart 1.…”

Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances

“…For example, megastigmatrienone and megastigmadienone isomers are constituents of the aroma of different fruits as well as they are present in rums and tobacco. Two regioselective syntheses of megastigma-4-one [57] and of megastigma-3-one [58] isomers have been developed (Figure 12). The reaction of γ-pyronene 60 with phenylsulfenyl chloride gave derivative 67 .…”