- Spectral comparisons of coniferyl and cinnamyl alcohol epoxide derivatives with a purported cis-epoxyconiferyl alcohol isolate
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The reported isolation of cis-epoxyconiferyl alcohol must be incorrect, based upon comparison of the reported Nuclear Magnetic Resonance (NMR) spectral data for the isolate with those for synthesized coniferyl and cinnamyl alcohol epoxide derivatives. Attempts to prepare cis- and trans-coniferyl alcohols were unsuccessful, although their acetate derivatives could be synthesized. The NMR spectral data for a synthetic sample of pinoresinol were in excellent agreement with those for the purported isolate. (C) 2000 Elsevier Science Ltd.
- Guz, Nathan R.,Stermitz, Frank R.
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- Ruthenium-Catalyzed Cross-Metathesis of Allyl Acetate and Styrenes: A Practical Approach to the Synthesis of Tripolinolate A and Its Analogs
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The scope of the Ru-catalyzed cross-metathesis of allyl acetates and styrenes was explored. A variety of electronically and structurally divergent styrenes were tolerated, and the resultant products were obtained in reasonable yields. The reported method was utilized in the synthesis of inhibitors of the proliferation of glioma and colorectal cancer cells, tripolinolate A and its diacetate analog.
- Araki, Yasuhiro,Topolov?an, Nikola,Kotora, Martin
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supporting information
p. 1736 - 1739
(2017/04/13)
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- Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs
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A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2-12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses. A simple and efficient method was designed to prepare tripolinolate A and its 19 analogs including nine new chemical entities for bioactive assay. Tripolinolate A and its analog 4,9-diacetyl-coniferol were found to be the two most active compounds that significantly inhibited the proliferation of different cancer cell lines with IC50 values ranging from 0.36 to 12.9 μM and induced apoptosis in tumor cells. Structure-activity relationship analysis suggested that the molecular size of acyl moieties at C-4 and C-9 position might have an effect on the activity of this type of coniferol derivatives.
- Chen, Lu,Liang, Ying,Song, Tengfei,Anjum, Komal,Wang, Wenling,Yu, Siran,Huang, Haocai,Lian, Xiao-Yuan,Zhang, Zhizhen
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supporting information
p. 2629 - 2633
(2015/06/08)
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- Synthesis of acyl analogues of coniferyl alcohol and their antimycobacterial activity
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In search of new anti-mycobacterial agents seven acyl and one benzyl derivatives of coniferyl alcohol were synthesized and evaluated along with coniferyl alcohol for antitubercular activity against Mycobacterium tuberculosis H37Rv (Mtb) in vitro. Four com
- Bhatti, Huma Aslam,Uddin, Nizam,Begum, Sabira,Siddiqui, Bina Shaheen
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p. 886 - 889
(2013/07/26)
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- DFRC Method for Lignin Analysis. 1. New Method for β-Aryl Ether Cleavage: Lignin Model Studies
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A new method for selective and efficient cleavage of arylglycerol-β-aryl (β-O-4) ether linkages in lignins is described and applied to several lignin β-ether models. The term "DFRC" was coined for derivatization followed by reductive cleavage. Derivatization, accompanied by cell wall solubilization, is accomplished with acetyl bromide (AcBr); reductive cleavage of resulting β-bromo ethers utilizes zinc in acetic acid. Degradation monomers, 4-acetoxycinnamyl acetates, from β-ether cleavage by the DFRC method were identified by NMR, GC-MS, and comparison of GC retention times with authentic compounds. Under the conditions used in this study, the β-ether linkage of all models was cleaved in very high (>92%) yield. The DFRC method produces simpler mixtures of monomers with higher yields than alternative hydrolytic methods. Because of its relative simplicity, mild conditions, and exceptional selectivity, this method should become a powerful analytical method for lignin characterization.
- Lu, Fachuang,Ralph, John
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p. 4655 - 4660
(2007/10/03)
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- Sulphite-promoted delignification of wood: identification of paucidisperse lignosulphonates
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Paucidisperse lignosulphonates, previously described as a distinct group of compounds called "hemilignins" (Mw ca. 2000), were conclusively shown to be a complex mixture of monomeric (C9) sulphonic acids.Since these compounds are rapidly solubilized only during the early stages of delignification from softwoods (/= 30percent lignin removal), it can be concluded that they are selectively removed from the secondary wall and not from the middle lamella.This result gives chemical support to the hypothesis that morphological differences in lignin stucture exist.It is proposed that the generation of monolignols and their sulphonated derivatives may occur via an α-O-aryl bond cleavage rather than β-O-aryl cleavage as previously suggested.For softwoods, several other major constituents were isolated, which may be derived from sulphonation of a β-hydroxylated form of coniferyl alcohol.
- Bialski, Alec M.,Luthe, Corinne E.,Fong, Jenny L.,Lewis, Norman G.
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p. 1336 - 1344
(2007/10/02)
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- DERIVATIVES OF UNSATURATED AROMATIC ALCOHOLS IN PROPOLIS AND STYRAX BENZOIN
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The benzoate of trans-coniferyl alcohol and the benzoate of trans-p-coumaryl alcohol have been obtained from propolis and the styrax benzoin, this being the first time that the latter has been described.
- Popravko, S. A.,Sokolov, I. V.,Torgov, I. V.
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p. 140 - 147
(2007/10/02)
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- Synthesis of Coniferyl and Dihydroconiferyl Derivatives Using Radical Bromination with N-Bromosuccinimide as the Key Step
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Coniferyl and dihydroconiferyl derivatives have been synthesized by reacting bromides, obtained from allylic and benzylic brominations using N-bromosuccinimide (NBS), with appropriate nucleophiles.For instance, NBS bromination of eugenol acetate, followed by replacement of bromine by an acetoxy group and subsequent reduction with lithium aluminium hydride, afforded coniferyl alcohol in 65percent overall yield.Due to the availability of the starting materials (eugenol and isoeugenol) and the good overall yields obtained, these synthetic routes compete well with other methods of preparation.
- Lindeberg, Otto
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