147677-05-2Relevant academic research and scientific papers
BIOSYNTHESIS OF LIGNANS IN FORSYTHIA INTERMEDIA
Rahman, Maiada M. A.,Dewick, Paul M.,Jackson, David E.,Lucas, John A.
, p. 1841 - 1846 (1990)
Feeding experiments with young shoots of Forsythia intermedia have shown that phenylalanine and ferulic acid are good precursors of the dibenzylbutyrolactone lignan arctigenin and the furofuran lignans phillygenin and epipinoresinol.Although matairesinol was incorporated into arctigenin, and epipinoresinol into phillygenin, in accord with late methylation steps in the biosynthetic pathway, some incorporation of label from one lignan class into the other was observed, particularly from epipinoresinol into arctigenin.This may indicate a high degree of catabolic activity followed by non-specific incorporation. Coniferyl alcohol was incorporated into all three lignans with a significant increase in the 3H:14C isotopic ratio.This supports the hypothesis that the lignans arise by oxidative coupling of two coniferyl alcohol units, rather than from two ferulic acid or coniferaldehyde units.The observed increase in isotopic ratio probably results from a primary isotope effect in the reversible oxidation-reduction reactions interrelating cinnamic acids and cinnamyl alcohols.A similar increase in isotopic ratio was measured during biosynthesis of the aryltetralin lactone lignan podophyllotoxin in Podophyllum hexandrum.
Design, synthesis of Cinnamyl-paeonol derivatives with 1, 3-Dioxypropyl as link arm and screening of tyrosinase inhibition activity in vitro
Tang, Kai,Jiang, Yi,Zhang, Huawei,Huang, Wenli,Xie, Yundong,Deng, Chong,Xu, Hongbo,Song, Xiaomei,Xu, Hong
, (2021)
This study aimed to obtain tyrosinase inhibitors for treating hyperpigmentation. A series of cinnamyl ester analogues were designed and synthesized with cinnamic acid (CA) and peaonol compounds. The safety, melanin content and inhibitory effects of all ta
Synthesis and in vitro biological evaluation of hybrids from tetrahydro-β-carboline and hydroxylcinnamic acid as antitumor carcinoma agents
Lin, Ying,Xia, Xuanping,Yao, Rongxin,Ni, Li,Hu, Jie,Guo, Wenjian,Zhu, Baoling
, p. 343 - 349 (2014)
Novel hybrids 8a-j and 9a-j were designed and synthesized by coupling the carboxyl group of hydroxylcinnamic acids with tetrahydro-β-carboline alkaloids which were linked with different substituted nitrogen-containing heterocycles at the positions-N9, and
FOUR TETRAHYDROISOQUINOLINE-MONOTERPENE GLUCOSIDES FROM CEPHAELIS IPECACUANHA
Nagakura, Naotaka,Itoh, Atsuko,Tanahashi, Takao
, p. 761 - 766 (1993)
Four new tetrahydroisoquinoline-monoterpene glucosides, trans-cephaeloside, cis-cephaeloside, 6-O-methyl-trans-cephaeloside and 6-O-methyl-cis-cephaeloside, have been isolated from the roots of Cephaelis ipecacuanha.Their structures have been elucidated o
Acylated pelargonidin glycosides from a red potato
Naito, Koichi,Umemura, Yoshiki,Mori, Motoyuki,Sumida, Takao,Okada, Toru,Takamatsu, Naoshi,Okawa, Yutaka,Hayashi, Kazuya,Saito, Norio,Honda, Toshio
, p. 109 - 112 (1998)
Two acylated pelargonidin glycosides were isolated from red tubers of a anthocyanin-rich tetraploid potato which was successfully selected from hybrid seedlings between cultivars of Solanum tuberosum and S. andigena. The major pigment was identified as pe
Synergistic Photobactericidal Activity Based on Ultraviolet-A Irradiation and Ferulic Acid Derivatives
Shirai, Akihiro,Kajiura, Masato,Omasa, Takeshi
, p. 1422 - 1428 (2015)
Ultraviolet-A (UV-A)-mediated bactericidal activity was enhanced by combined treatment with trans-ferulic acid (trans-FA, compound 1) or its derivatives. Derivative compounds 4 and 10 contain a phenyl group or an l-tyrosine HCl tert-butyl ester, respectiv
Design, synthesis and biological evaluation of curcumin analogues as novel LSD1 inhibitors
Wang, Jiming,Zhang, Xiangyu,Yan, Jiangkun,Li, Wei,Jiang, Qinwen,Wang, Xinran,Zhao, Dongmei,Cheng, Maosheng
, (2019)
Histone lysine-specific demethylase 1 (LSD1) was the first discovered histone demethylase. Inactivating LSD1 or downregulating its expression inhibits cancer-cell development, and thus, it is an attractive molecular target for the development of novel cancer therapeutics. In this study, we worked on the structural optimization of natural products and identified 30 novel LSD1 inhibitors. Utilizing a structure-based drug design strategy, we designed and synthesized a series of curcumin analogues that were shown to be potent LSD1 inhibitors in the enzyme assay. Compound WB07 displayed the most potent LSD1 inhibitory activity, with an IC50 value of 0.8 μM. Moreover, WA20 showed an anticlonogenic effect on A549 cells with an IC50 value of 4.4 μM. Molecular docking simulations were also carried out, and the results indicated that the inhibitors bound to the protein active site located around the key residues of Asp555 and Asp556. These findings suggested that compounds WA20 and WB07 are the first curcumin analogue-based LSD1 inhibitors with remarkable A549 suppressive activity, providing a novel scaffold for the development of LSD1 inhibitors.
(S)-allyl cysteine derivatives as a new-type cholinesterase inhibitor
Kim, Beom-Cheol,Lee, Seung-Hwan,Jang, Mi,Won, Moo-Ho,Park, And Jeong Ho
, p. 52 - 58 (2015)
Even though cholinesterase (ChE) inhibitors and N-methyl-D-aspartate (NMDA) receptor antagonist are clinically approved to treat Alzheimer's disease (AD) patients, new therapeutic compounds still need to be developed. Therefore, many new targets and novel
Design, synthesis and "in vitro" anti-leukemic evaluation of ferulic acid analogues as BCR-Abl inhibitors
Rajendran, Narendran,Subramaniam, Shankar,Charan Raja, Mamilla R.,Venkata Subbarao, Himesh Makala,Raghunandan, Subhashree,Venkatasubramanian, Ulaganathan,Pemaiah, Brindha,Mahapatra, Santanu Kar,Sivasubramanian, Aravind
, p. 70480 - 70484 (2016)
Semi-synthetic modification of ferulic acid isolated from Salicornia brachiata was performed and the derivatives showed gratifying in silico binding scores with the BCR-Abl protein, comparable with imatinib. Anti-proliferative activity against K562, U937 and Hep G2 cancer cell lines and the BCR-Abl kinase inhibitory activity using an ADP-Glo assay were investigated. Compounds 2i and 3j were potent BCR-Abl inhibitors and were also active against K562 cells.
A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives
Moni, Lisa,Banfi, Luca,Basso, Andrea,Mori, Alessia,Risso, Federica,Riva, Renata,Lambruschini, Chiara
, p. 1737 - 1749 (2021/03/23)
A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.
