9-(3,4-Dimethyl-5-pentyl-furan-2-yl) nonanoic Acid and 9-(3,4-DimethyI-5-propyl-furan-2-yl) nonanoic Acid: New Naturally Occurring Peroxidase Inhibitors

Abstract

9-(3,4-Dimethyl-5-pentyl-furan-2-yl) nonanoic acid [diMeF(9,5)] and 9-(3,4-dimethyl-5-propyl-furan-2-yl) nonanoic acid [diMeF(9,3)] and its corresponding methyl esters have been assayed for inhibitory activity on horseradish peroxidase (E C 1.11.1.17) by measuring the peroxidase-catalyse decomposition of indole-3-acetic acid. Both compounds and their meth-ylates are com petitive inhibitors to horseradish peroxidase with inhibitor constants (K1) of 50 ± 0.9 × 10-5 ᴍ respectively 5.2 ± 0.8 × 10-5 ᴍ. Development of inhibitory effect requires not only the presence of the furan heterocycle but also of a polar side chain.

Potential favourable health effects of some dietary uncommon fatty acids

“…FuFAs present in fish may be involved in the beneficial effects of fish consumption on cardiovascular disease (Spiteller, 2005). Several in vitro studies support this hypothesis (Graff et al, 1984;Okada et al, 1996;Fuchs and Spiteller, 1999) as well as studies conducted in humans (Wahl et al, 1994;Zheng et al, 2016;Tovar et al, 2017). Moreover, in vitro FuFAs modulate lipid metabolism in adipose tissues (Lengler et al, 2012;Lauvai et al, 2019).…”

Furan fatty acid concentrations in tea infusions prepared from green, black, and herbal teas

“…Although 3‐carboxy‐4‐methyl‐5‐propyl‐2‐furanpropanoic acid (CMPF), which could be a metabolite of FuFAs, was present at higher levels in plasma of persons with metabolic diseases (diabetes and renal pains), overall positive health effects were assigned to FuFAs (Xu et al, 2017). Studies by different scientists indicated that positive effects assigned to the presence of polyunsaturated fatty acids (PUFA) could also be attributable to or improved by FuFAs (Ciminiello et al, 1991; Fuchs & Spiteller, 1999; Spiteller, 2005, 2007; Wakimoto et al, 2011). Accordingly, the positive properties associated with fish oil consumption such as anti‐inflammatory and cholesterol lowering effects and possible preventing effects on arteriosclerosis and Alzheimer's disease, may also be due to the presence of FuFAs (Ciminiello et al, 1991; Spiteller, 2007).…”

“…FuFAs are known to be powerful radical scavengers, peroxidase inhibitors and antioxidants (Fuchs & Spiteller, 1999; Spiteller, 2005). In addition, they may be protective against a number of age‐related diseases (Ciminiello et al, 1991; Fuchs & Spiteller, 1999; Spiteller, 2005; Wakimoto et al, 2011).…”

Synthesis of novel tri‐ and tetrasubstituted C18 furan fatty esters

“…The functionalization of the furan ring, especially at the less-reactive sites, namely, the 3-and 4-positions of the heteroaromatic ring, has been one of the greatest challenges in furan syntheses (21)(22)(23). In the field of lipids, some natural tetrasubstituted furan FA are potent peroxidase inhibitors (24).…”

“…C NMR (CDCl 3 , δ C ):13.95 (C-18),22.51 (C-17),24.59 (d, J = 3.1 Hz, C-13),24.83 (C-3),27.63 (d, J = 1 6. Hz, C-14),27.66 (C-7),28.39 (C-8),28.69,28.79, 28.88, 28.96, 31.43 (C-16), 33.97 (C-2), 51.31 (COOCH 3 ), 98.04 (d, J = 20.4 Hz, C-10), 136.12 (d, J = 26.1 Hz, C-12), 148.44 (d, J = 243 2.…”