- Bioactive constitutents from the stems of Annona montana.
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Three structurally related acid amides, N-trans-feruloyltyramine (1), N-p-coumaroyltyramine (2), and N-trans-caffeoyltyramine (3), one lignan, (-)-syringaresinol (4), one aromatic aldehyde, syringaldehyde (5), and two steroids, beta-sitosterol and beta-si
- Wu,Chang,Ko,Teng
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- Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
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Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.
- Dong, Hongbo,Du, Weihong,He, Yujiao,Shi, Zheng,Wang, Yingying,Wu, Min
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p. 2866 - 2874
(2021/11/12)
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- Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives
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Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 μM. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the α-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of ?7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.
- Guan, Li,Zhou, Junting,Lin, Qinghua,Zhu, Huilin,Liu, Wenyuan,Liu, Baolin,Zhang, Yanbo,Zhang, Jie,Gao, Jing,Feng, Feng,Qu, Wei
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p. 2657 - 2665
(2019/05/01)
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- Investigating isomer specific photoprotection in a model plant sunscreen
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Sinapate esters are used throughout the plant kingdom, for example in photoprotection from ultraviolet radiation. Sinapate esters are naturally produced in their E-isomeric form; however, upon exposure to ultraviolet radiation, photoisomerization drives Z-isomer formation. To elucidate the photoprotection capacity of E vs. Z forms of sinapate esters, we explore the photochemistry of the model system, Z-ethyl sinapate. Following a novel Z-ethyl sinapate synthesis, we demonstrate that photoprotection is isomer independent. This suggests that, regarding photoprotection, there were no evolutionary pressures for biosynthesis of either isomer.
- Horbury,Flourat,Greenough,Allais,Stavros
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supporting information
p. 936 - 939
(2018/02/07)
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- Halogen or nitrogen-containing group substituted bibenzyl analog, preparation method and uses thereof
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The present invention discloses a halogen or nitrogen-containing group substituted bibenzyl analog or a pharmaceutically acceptable salt, a hydrate thereof, wherein the halogen or nitrogen-containing group substituted bibenzyl analog is represented by a f
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Paragraph 0034; 0036; 0036; 0037; 0038; 0039
(2017/04/20)
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- Esterification mechanism of lignin with different catalysts based on lignin model compounds by mechanical activation-assisted solid-phase synthesis
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In order to learn about the esterification mechanism of lignin by mechanical activation-assisted solid-phase synthesis (MASPS) technology, lignin model compounds, p-hydroxy benzaldehyde (H), vanillin and vanillyl alcohol (G), and syringaldehyde (S), were used in the reaction with acetic anhydride, with 4-dimethyl amino pyridine (DMAP), sodium acetate, and sulfuric acid as catalysts. FTIR, NMR, and UV/vis analyses of the products showed that all of the catalysts could enhance the esterification. Both the phenolic hydroxyl and aliphatic hydroxyl participated in the esterification and the reactivity of the basic structural units of lignin had a descending order of H, G, and S. Oxidations could happen in the presence of unsaturated groups such as aldehyde in the lignin model compounds. The catalytic mechanism of the three kinds of catalyst was different, and the catalytic activity had a descending order of DMAP, sodium acetate, and sulfuric acid. The reactivity of phenolic hydroxyl was higher than that of aliphatic hydroxyl with DAMP as the catalyst, but the reactivity of aliphatic hydroxyl was higher than that of phenolic hydroxyl with sodium acetate or sulfuric acid as the catalyst. With sulfuric acid as the catalyst, some side reactions took place and resulted in the ring cleavage or cross-linking of the benzene ring. Consistency verification indicated that the use of lignin model compounds for studying the esterification mechanism of lignin was reasonable and feasible.
- Zhao, Xiaohong,Zhang, Yanjuan,Wei, Liping,Hu, Huayu,Huang, Zuqiang,Yang, Mei,Huang, Aimin,Wu, Juan,Feng, Zhenfei
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p. 52382 - 52390
(2017/11/27)
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- Synthesis and evaluation of neuroprotective 4-O-substituted chrysotoxine derivatives as potential multifunctional agents for the treatment of Alzheimer's disease
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A series of 4-O-substituted chrysotoxine (CTX) derivatives were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's disease (AD). In vitro assays indicated that four ring substituted compounds (2a, 2b, 3i and 3j)
- Guan, Li,Hao, Yanfeng,Chen, Lei,Wei, Meng-Lin,Jiang, Qin,Liu, Wen-Yuan,Zhang, Yan-Bo,Zhang, Jie,Feng, Feng,Qu, Wei
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p. 22827 - 22838
(2016/03/12)
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- A selective and mild glycosylation method of natural phenolic alcohols
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Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.
- Mastihubová, Mária,Poláková, Monika
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p. 524 - 530
(2016/04/08)
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- An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains
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To optimize antioxidant activity and lipophilicity of cinnamic acid derivatives (CAs) including ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, and p-hydroxycinnamic acid, four analogs bearing an additional double bond between their aromatic ring and propenoic acid moiety were designed and synthesized based on the conjugated chain elongation strategy. The antioxidant performance of the CAs were investigated by 2,2′-diphenyl-1-picrylhydrazyl (DPPH)-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage-inhibiting and anti-haemolysis activity assays. It was found that CAs with elongation of conjugated chains display increased DPPH --scavenging, DNA strand breakage-inhibiting and anti-haemolysis activities as compared to their parent molecules, due to their improved hydrogen atom-donating ability and lipophilicity. Overall, this work highlights an effective strategy to develop potential CA-directed antioxidants by elongating their conjugated chain.
- Li, Yan,Dai, Fang,Jin, Xiao-Ling,Ma, Meng-Meng,Wang, Yi-Hua,Ren, Xiao-Rong,Zhou, Bo
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- Studies on the total synthesis of tenuifoliside B
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An efficient synthesis of tenuifoliside B, which shows potential cognitive improvement and cerebral protective effects that may be further developed to become an anti-AD lead compound, has been developed starting from commercial available starting materials. Regioselective introductions of acyl groups to the OH-3′ and OH-6 of sucrose play the key steps by metal chelate-directed acylation and Mitsunobu esterification, respectively.
- Wu, Yongjiang,Shi, Qiyuan,Lei, Houliang,Liu, Xuesong,Luan, Lianjun
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p. 3757 - 3761
(2014/05/20)
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- An efficient synthetic strategy for obtaining 4-methoxy carbon isotope labeled combretastatin a-4 phosphate and other Z-combretastatins
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Human cancer and other clinical trials under development employing combretastatin A-4 phosphate (1b, CA4P) should benefit from the availability of a [11C]-labeled derivative for positron emission tomography (PET). In order to obtain a suitable
- Pettit, George R.,Minardi, Mathew D.,Hogan, Fiona,Price, Pat M.
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experimental part
p. 399 - 403
(2010/08/05)
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- Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships
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Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure-antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively.
- Bratt, Katarina,Sunnerheim, Kerstin,Bryngelsson, Susanne,Fagerlund, Amelie,Engman, Lars,Andersson, Rolf E.,Dimberg, Lena H.
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p. 594 - 600
(2007/10/03)
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- Compositions containing aromatic aldehydes and their use in treatments
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Disclosed are pharmaceutical and cosmetic compositions containing aromatic aldehyde compounds. Some of the disclosed compositions are useful as topical therapeutics for treating inflammatory dermatologic conditions. Some of the compositions are useful in transdermal and other systemic dose forms for treating other inflammatory conditions in mammals.
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- Synthesis of aryl glycosides as vir gene inducers of Agrobacterium tumefaciens
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Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated. Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated.
- Delay,Cizeau,Delmotte
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p. 179 - 188
(2007/10/02)
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- NEW SYNTHESES OF PLANT ARYL GLYCOSIDES AS POTENTIAL GENE INDUCERS
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Aryl β-D-glycopyranosides have been synthesized by coupling acetovanillone (4-hydroxy-3-methoxyacetophenone) with D-glucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with D-glucose and D-galactose; syringaldehyde (3-methoxyvanillin) with D-glucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-glucose.The Mauthner's procedure using peracetylated glycosyl bromides and phenolates in aqueous acetone afforded the acetylated β-D-glycosides, which were deacetylated.
- Delay, Didier,Delmotte, Francis
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p. 223 - 234
(2007/10/02)
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- The Wittig Reaction of 2-t-Butoxycarbonyl-1-methoxycarbonylethylidenetriphenylphosphorane: A Surrogate for Stobbe Reaction
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The reaction of 2-t-butoxycarbonyl-1-methoxycarbonylethylidenetriphenylphosphorane (3) with a range of aromatic aldehydes has been explored.The resultant itaconic esters, obtained in high yield, are readily converted into methyl 4-acetoxynaphthalene-2-carboxylates.
- Rizzacasa, Mark A.,Sargent, Melvyn V.
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p. 1737 - 1743
(2007/10/02)
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- THREE DIHYDROISOCOUMARIN GLUCOSIDES FROM HYDRANGEA MACROPHYLLA SUBSP. SERRATA
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Three new dihydroisocoumarin glucosides, macrophyllosides A, B and C were obtained from dry leaves of Hydrangea macrophylla subsp. serrata, together with the previously known hydrangenol 8-β-glucoside.Using NMR and CD techniques and some chemical transformation, the structures were elucidated as (3S)-3',4',5'-trimethoxyphenyl-8-β-D-glucopyranosyl dihydroisocoumarin, (3R)- and (3S)-3',5'-dimethoxy-4'-hydroxyphenyl-8-β-D-glucopyranosyl dihydroisocoumarins.CD experiments indicated that hydrangenol 8-β-glucoside was the mixture of 3S- and 3R-stereoisomers.Key Word Index - Hydrangea macrophylla subsp. serrata; Saxifragaceae; macrophyllosides A, B and C; dihydroisocoumarin glucosides; bitter principles; plant growth inhibitory activity.
- Hashimoto, Toshihiro,Tori, Motoo,Asakawa, Yoshinori
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p. 3323 - 3330
(2007/10/02)
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