Inhibition of UVA Damage on Human Skin Dermis Fibroblasts by the Isoflavonoid Intermediate Deoxybenzoin-3A

Abstract

Ultraviolet rays are the main cause of skin aging. Isoflavone structures are good anti-ultraviolet natural compounds and have an especially strong anti-ultraviolet B (UVB) effect. However, the anti-ultraviolet A (UVA) effect of isoflavones is more controversial. Therefore, this study aims to discover which isoflavone analogue possesses a strong anti-ultraviolet A. We found the isoflavonoid intermediate deoxybenzoin-3A (DOB-3A) to be a similar isoflavone structural compound with strong anti-ultraviolet A effects. Ultraviolet rays with a wavelength of 350 nm are used to irradiate the fibroblasts of the human skin. Western blot, flow cytometry, and transmission electron microscope analyses were used to explore its anti-ultraviolet A mechanism. We established the results that DOB-3A (1) reduced the death of fibroblasts caused by ultraviolet A, (2) avoided the damage to the organelles and structures after UVA irradiation, (3) inhibited the generation of intracellular reactive oxygen species (ROS) and hydrogen peroxide-induced damage, and (4) decreased the phosphorylation of mitogen-activated protein kinases (MAPK) caused by UVA. Based on the above findings, DOB-3A is a very good anti-ultraviolet A isoflavone-related structure. Because it is simple to synthesize and has good effects, DOB-3A is a suitable anti-ultraviolet A product with an isoflavone structure. Moreover, DOB-3A’s structure provides a reference for the synthesis of anti-UVA isoflavones.

Inhibitory Effects of B-, C-, and E-Ring-Truncated Deguelin Derivatives Against A549, HCT116, and MCF-7 Cancer Cells

“…All reagents were purchased and used as received, unless otherwise specified. 1 H and 13 C NMR spectra were recorded on a Varian 500 MHz spectrometer using deuterated dimethyl sulfoxide (DMSOd 6 ). 1 H and 13 C chemical shifts are expressed in parts per million (ppm) and are referenced at 2.50 and 39.5 ppm, respectively.…”

“…1 H and 13 C NMR spectra were recorded on a Varian 500 MHz spectrometer using deuterated dimethyl sulfoxide (DMSOd 6 ). 1 H and 13 C chemical shifts are expressed in parts per million (ppm) and are referenced at 2.50 and 39.5 ppm, respectively. Data are presented as follows: chemical shift (δ), multiplicity (s = singlet, d = doublet, dd = doublet of doublet, t = triplet, q = quartet, and m = multiplet), coupling constants (J) in Hz, and integration.…”

“…O-Acylated derivative 9 was produced using acetic anhydride, Et 3 N, and DMAP in DCM. The analogues were obtained in good yields and characterized by using various techniques such as 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS).…”

“…MP = 151 °C; 1 H NMR (500 MHz, DMSO-d 6 ) δ 11.04 (s, 1H), 9.85 (s, 1H), 7.29 (d, J = 8.4, 1H), 6.86 (s, 1H), 6.82 (d, J = 8.1 Hz, 1H), 6.66 (d, J = 3.2 Hz, 1H), 6.26 (d, J = 7.1 Hz, 2H), 4.07 (s, 2H), 3.95 (s, 3H), 3.69 (s, 3H), 3.67 (s, 3H). 13…”

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

“…Deoxybenzoin (DOB) motifs are commonly found in many natural products, pharmaceutically-active molecules and fire-resistant polymers [ 1 , 2 , 3 , 4 ]. In addition, some DOB derivatives have been sporadically reported to possess activities such as β estrogenic agonist, antiallergic, anti-inflammatory and antimicrobial activities [ 5 , 6 , 7 ].…”