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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).
Back to the Future – The Prospects of African Indigenous Crops as Future Foods
Published in David R. Katerere, Wendy Applequist, Oluwaseyi M. Aboyade, Chamunorwa Togo, Traditional and Indigenous Knowledge for the Modern Era, 2019
Callistus Bvenura, Estonce T. Gwata, Felix D. Dakora
The antioxidant potential of cassava flour has been documented (Eleazu et al. 2011). Yi et al. (2010) were able to extract balanophonin, isovanillin, 6-deoxyjacareubin, syringaldehyde, p-coumaric acid, coniferaldehyde, pinoresinol, ethamivan, ficusol, and scopoletin, some important phenolic compounds, from the stem. Organic fertilizers increase polyphenolic compounds, including flavonoids and phenolic acids, and thereby increase the antioxidant activities of cassava tubers (Omar et al. 2012). In vivo studies have also shown cassava flavonoid leaf extracts to ameliorate carbon tetrachloride-induced injury in the livers of mice (Tao et al. 2014). The anticancer activity of esculentoic acids A and B, isolated from leaf extracts, showed moderate in vitro cytotoxicity against the A2780 human ovarian cancer cell line (Lim 2016). Cassava stem oil showed significant cytotoxicity against human erythromyeloblastoid leukemia cell lines with IC50 value of 7 μg/ml. Other potential bioactivities such as anti-inflammatory, antimicrobial, hypotensive, antihyperglycemic, antioxidant, antipyretic, analgesic, hepatoprotective, anthelmintic, amoebicidal, and prebiotic properties have also been reported (Lim 2016).
A novel plant-derived compound is synergistic with 5-fluorouracil and has increased apoptotic activity through autophagy in the treatment of actinic keratoses
Published in Journal of Dermatological Treatment, 2022
Cameron E. West, Shawn G. Kwatra, Justin Choi, Daniel Von Hoff, Laurence Booth, Paul Dent
Due to their widely touted health benefits, plant-based compounds continue to garner attention for their untapped therapeutic potential. Bioactive phytochemicals have repeatedly been shown to exert anti-carcinogenic, anti-inflammatory, and anti-oxidative properties throughout multiple organ systems, including the skin (1). Accordingly, there has been growing interest in understanding how dermatologic disorders can be managed using plant-based derivatives. One such compound is GZ17-6.02, a novel, oral synthetic investigational compound that is a mixture of three originally plant-derived components (curcumin, isovanillin, and harmine), which is currently undergoing Phase-I oncology trials in the USA (NCT03775525) after having demonstrated in vivo activity against pancreatic cancer, colorectal cancer, and head and neck squamous cell carcinoma (2–4). We thus hypothesized that GZ17-6.02 would show efficacy in treating actinic keratoses (AK).
Synthesis, antitumor activity, and molecular docking study of 2-cyclopentyloxyanisole derivatives: mechanistic study of enzyme inhibition
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
Walaa M. El-Husseiny, Magda A.-A. El-Sayed, Adel S. El-Azab, Nawaf A. AlSaif, Mohammed M. Alanazi, Alaa A.-M. Abdel-Aziz
The synthetic strategies used to obtain the target compounds are presented in Schemes 1–3. The O-alkylation of isovanillin (1) with bromocyclopentane was successively conducted in the presence of K2CO3 and a phase transfer catalyst tetrabutylammonium bromide (TBAB) in THF to obtain the key intermediate 3-cyclopentyloxy-4-methoxybenzaldehyde (2) that provided the core structure of phosphodiesterase-4 inhibitors37. Tetrabutylammonium bromide successively exhibited the character of phase transfer catalyst in an environmentally friendly procedure under mild conditions37.
Role of human flavin-containing monooxygenase (FMO) 5 in the metabolism of nabumetone: Baeyer–Villiger oxidation in the activation of the intermediate metabolite, 3-hydroxy nabumetone, to the active metabolite, 6-methoxy-2-naphthylacetic acid in vitro
Published in Xenobiotica, 2021
Kaori Matsumoto, Tetsuya Hasegawa, Kosuke Ohara, Tomoyo Kamei, Junichi Koyanagi, Masayuki Akimoto
On the other hand, the formation of 6-MNA was also observed in HLC without cofactors, but to a lesser extent than that in the presence of NAD+ (Figure 5). AO is a cytosolic enzyme that catalyzes the oxidation of aldehyde derivatives to the corresponding carboxylic acids without cofactors (Garattini and Terao 2012). Evaluations using specific inhibitors and human recombinant enzyme systems are useful for obtaining a more detailed understanding of AO-mediated metabolism. Our studies, incubated the hFMO5 oxidative extracts in recombinant AO with and without inhibitors (Strelevitz et al.2012, Rodrigues et al.2014). The results from the human AO recombinant system suggested that AO mediated the conversion to 6-MNA. However, typical inhibitors, MD and RF did not exert inhibitory effects (Table 4). RF inhibition of AO is substrate-dependent (Obach 2004). The AO inhibition by RF is atypical and the inhibition process occurs via either a competitive, mixed, or uncompetitive mode (Dalvie and Di 2019). It is suggested that AO may have multiple substrate/inhibitor recognition sites. Although it is a common AO substrate, there is a phenomenon that its metabolic activity is not strongly inhibited by a typical inhibitor, and in that case, substrate/inhibitor is then thought to be recognised at different sites in AO. HZ, which is considered to be an irreversible inhibitor of AO, weakly inhibited 6-MNA formation from 6-MN-CHO in recombinant AO (p = 0.013). On the contrary, isovanillin (IV), a close structural analog of vanillin, and 6-methoxy-2-naphthaldehyde (6-MN), a similar structural analog of 6-MN-CHO, also significantly inhibited the metabolism of 6-MN-CHO with recombinant AO (p < 0.001). Both compounds have a carbonyl moiety in their molecular structure. Considering these results, AO might be also involved in 6-MNA production. Furthermore, based on the lack of inhibitory activity by AP on the formation of 6-MNA, XO is also unlikely to be the principal enzyme mediating the formation of 6-MNA in HLC (Table 3) (Panoutsopoulos et al.2004).