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Syzygium Aromaticum, Curcuma Longa, and Lavandula: Volatile Components and Antioxidant Activities
Published in Amit Baran Sharangi, K. V. Peter, Medicinal Plants, 2023
The volatile compounds were adsorbed to the bar for 60 min and then TD-GC-MS procedure was performed. The number of volatile compounds originating from clove buds was influenced by growth phases. In phase III (bright red) it was greater compared with that in phase II (pink) as shown in Table 6.1. Although β-caryophyllene, eugenol, eugenol acetate, α-farnesene, α-humulene, and γ-murolene were identified in all growth phases,α-copaene, ethyl hexanoate, methyl salicylate, 2-nonanone, and β-ocimene were newly present in phase II and phase III. In phase III acetophenone, ethyl benzoate, ethyl octanoate, and methyl benzoate, were identified. It is assumed that characteristic fragrance originating from ripened buds is influenced from the increased compounds. From clove leaves 3-hexen-1-ol and hexyl acetate were identified as compounds characteristic of leaves (Table 6.1).
Biotransformation of Sesquiterpenoids, Ionones, Damascones, Adamantanes, and Aromatic Compounds by Green Algae, Fungi, and Mammals
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Yoshinori Asakawa, Yoshiaki Noma
A microalgae E. gracilis Z. also contains reductase. The following aromatic aldehydes were treated in this organism: benzaldehyde; 2-cyanobenzaldehyde; o-, m-, and p-anisaldehyde; o-, m-, and p-salicylaldehyde; o-, m-, and p-tolualdehyde; o-chlorobenzaldehyde; p-hydroxybenzaldehyde; o-, m-, and p-nitrobenzaldehyde; 3-cyanobenzaldehyde; vanillin; isovanillin; o-vanillin; nicotine aldehyde; 3-phenylpropionaldehyde; and ethyl vanillin. Veratraldehyde, 3-nitrosalicylaldehde, phenylacetaldehyde, and 2-phenylproanaldehyde gave their corresponding primary alcohols. 2-Cyanobenzaldehyde gave its corresponding alcohol with phthalate. m- and p-Chlorobenzaldehyde gave its corresponding alcohols and m- and p-chlorobenzoic acids. o-Phthalaldehyde and p-phthalate and iso- and terephthalaldehydes gave their corresponding monoalcohols and dialcohols. When cinnamaldehyde and α-methyl cinnamaldehyde were incubated in E. gracilis, cinnamyl alcohol and 3-phenylpropanol, and 2-methylcinnamyl alcohol, and 2-methyo-3-phenylpropanol were obtained in good yield. E. gracilis could convert acetophenone to 2-phenylethanol; however, its enantio-excess is very poor (10%) (Takahashi, 1994).
Synthesis of Important Chiral Building Blocks for Pharmaceuticals Using Lactobacillus and Rhodococcus Alcohol Dehydrogenases
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
Marion Rauter, Simon Krebs, Gotthard Kunze
For initial ADH-testing or for reaction optimization, acetophenone is a prominent substrate. It is reduced to 1-(R)- or 1-(S)-phenylethanol in dependence of the enzyme’s stereoselectivity. Enantiopure 1-(R)- or 1-(S)-phenylethanol is used in fragrance preparations and as intermediate for pharmaceuticals.
A review on synthetic chalcone derivatives as tubulin polymerisation inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Wenjing Liu, Min He, Yongjun Li, Zhiyun Peng, Guangcheng Wang
The antiproliferative activity of some novel indole-chalcone derivatives 52 (Figure 35) against different human cancer cell lines was evaluated using the MTT assay102. In this series, analog 52a showed the strongest bioactivity against six cancer cells (A549, HeLa, Bel-7402, MCF-7, A2780, HCT-8) with IC50 values in the range of 3 − 9 nM. SAR analysis indicated that the position of the methoxy group on indole was very important for its antiproliferative activity, and the order of potency was 6-OCH3 > 5-OCH3 > 4-OCH3. Interestingly, the methyl group at the N-1 position has the opposite effect on the acetophenone and propiophenone analogs. Mechanism studies revealed that 52a could arrest the cell cycle at the G2/M phase and induce apoptosis along with the decrease of mitochondrial membrane potential. In addition, 52a was found to be a novel tubulin polymerisation inhibitor that could bind colchicine sites. Importantly, 52a (including its phosphate) showed better metabolic stability in mouse liver microsomes, as well as exhibited good inhibitory activity against the tumour growth in xenograft models in vivo without apparent toxicity, which was superior to the control compound.
Design, synthesis, and evaluation of chalcone-Vitamin E-donepezil hybrids as multi-target-directed ligands for the treatment of Alzheimer’s disease
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Zhipei Sang, Qing Song, Zhongcheng Cao, Yong Deng, Li Zhang
To determine the effects of the chalcone-Vitamin E-donepezil hybrids on self-induced Aβ1–42 aggregation, the inhibition assay and disaggregation assay were performed using the thioflavin T (ThT) fluorescence assay29. Curcumin compounds 8 and 16 were also tested. The data were collected in Table 3. For the inhibition assay, the precursor compounds 8 (23.1%) and 16 (27.7%) indicated lower inhibitory activity than curcumin (47.3%), and donepezil exhibited no significant inhibition potency (under 5% inhibition ratio at 25 µM). The target compounds (9a–f, 10, and 17a–f) showed exhibited more inhibitory potency than curcumin. Generally, compounds 17a–f indicated better inhibitory activity than other compounds. Seen from the screen data, replacing the N-ethyl-2-methoxy-benzenemethanamine group of 9b (63.4%) with the diethylene group to obtain the compound 10, getting a waned dramatically inhibition ratio of 37.7%. Compound 17f showed higher inhibition potency with an inhibition ratio of 78.0%. These results demonstrated that the hydroxyl group at the 2- and 4-position in the acetophenone moiety (A ring) could play an important role in inhibiting self-mediated Aβ1–42 aggregation, and the 2-methoxybenzyl substitutions contributed to the inhibition potency, however, the diethylamine group might be the disadvantageous effect on inhibitory potency.
Synthesis, anti-inflammatory, cytotoxic, and COX-1/2 inhibitory activities of cyclic imides bearing 3-benzenesulfonamide, oxime, and β-phenylalanine scaffolds: a molecular docking study
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
Alaa A.-M. Abdel-Aziz, Adel S. El-Azab, Nawaf A. AlSaif, Mohammed M. Alanazi, Manal A. El-Gendy, Ahmad J. Obaidullah, Hamad M. Alkahtani, Abdulrahman A. Almehizia, Ibrahim A. Al-Suwaidan
Here, we report the design and synthesis of novel cyclic imides containing 3-benzenesulfonamide, acetophenone oxime, and β-phenylalanine scaffolds. The designed cyclic imides (Figure 1(I)) were subjected to various analyses to: (i) investigate their in vivo anti-inflammatory and ulcerogenic activities, and their in vitro COX-1/2 inhibitory effects; (ii) study their in vitro cytotoxicity activity; (iii) explore their structure-activity relationships (SAR) based on their in vivo anti-inflammatory effects and in vitro COX-1/2 inhibitory activity with molecules containing substituted cyclic imides; (iv) compare the biological effects of 3-benzenesulfonamide to those of acetophenone oxime and β-phenylalanine based on in vivo anti-inflammatory and COX-1/2 inhibition; and (v) conduct a molecular docking study of the target derivatives to investigate their binding with the COX-2 isozyme.