Policosanols (PCs) are long-chain linear aliphatic alcohols that are present in the primary leaves of cereal crops, such as barley and wheat, sugar cane wax, and beeswax. PCs have been used as a nutraceutical for improving hyperlipidemia and hypercholesterolemia. However, the PC content in mutant wheat lines has not been investigated. To select highly functional wheat sprouts with a high content of PCs in wheat mutant lines developed via gamma-irradiated mutation breeding, we cultivated the sprouts of wheat mutant lines in a growth chamber with white LED light (6000 K) and analyzed the PC content in these samples using GC-MS. We studied the PC content in 91 wheat sprout samples: the original variety (Woori-mil × D-7; WS01), commercially available cv. Geumgang (WS87) and cv. Cheongwoo (WS91), and mutant lines (WS02–WS86 and WS88–WS90) developed from WS01 and WS87. Compared to WS01, 18 mutant lines exhibited a high total PC content (506.08–873.24 mg/100 g dry weight). Among them, the top 10 mutant lines were evaluated for their PC production after cultivating under blue (440 nm), green (520 nm), and red (660 nm) LED light irradiation; however, these colored LED lights reduced the total PC production by 35.8–49.7%, suggesting that the cultivation with white LED lights was more efficient in promoting PCs’ yield, compared to different LED lights. Therefore, our findings show the potential of radiation-bred wheat varieties as functional foods against hyperlipidemia and obesity and the optimal light conditions for high PC production.

Isoegomaketone [(E)-1-(furan-3-yl)-4-methylpent-2-en-1-one; 1] is abundant in the essential oil of Perilla species and exhibits various biological activities, such as anticancer and anti-inflammatory effects. In order to discover compounds with reduced toxicity or enhanced biological activity through structural modification of natural product-derived components, isoegomaketone was irradiated with an electron beam at five different doses, and (±)-8-methoxy-perilla ketone (2) was obtained with the highest yield of 3.8% (w/w) at 80 kGy. Its structure was identified by one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy and high-resolution chemical ionization mass spectrometry. Compound 2 inhibited nitric oxide production and inducible nitric oxide synthase mRNA expression in a dose-dependent manner in lipopolysaccharide-stimulated RAW 264.7 cells. It also dose-dependently suppressed the mRNA expression of pro-inflammatory mediators such as IL-1β, IFN-β, and MCP-1, while having no significant effect on IL-6 mRNA levels. Furthermore, ELISA analysis demonstrated that 2 reduced MCP-1 protein expression but did not affect the protein level of TNF-α or IL-6. This study provides a reference for the structural analysis of compounds related to 2 by presenting NMR data acquired with chloroform-d, and is the first to report the anti-inflammatory properties of 2.

Gamma irradiation serves as a robust platform for the structural diversification of natural compounds, utilizing high-energy reactions with free radicals to generate novel scaffolds with improved biological properties. In present study, p-coumaric acid was exposed to ionizing radiation at various doses to induce molecular transformations. Significant degradation of the precursor was confirmed at a dose of 60 kGy, which provided the optimal range for the generation of radiolysis products. The chromatographic fraction of the resulting mixture afforded two novel derivatives, 1 and 2, along with a known analog 3. Comprehensive spectroscopic characterization assigned their structures as (3R,4R)-3-hydroxymethyl-4-(4-hydroxyphenyl)-dihydrofuran-2(3H)one (1), (3R*,4S*)-3-hydroxymethyl-4-(4-hydroxyphenyl)-dihydrofuran-2(3H)-one (2), and (4S)-4-(4-hydroxyphenyl)-dihydrofuran-2(3H)-one (3). The anti-inflammatory effects of the isolates were evaluated using lipopolysaccharide-stimulated RAW264.7 macrophages. While neither the parent compound p-coumaric acid nor its derivatives exhibited significant cytotoxicity at concentrations up to 40 μM, their anti-inflammatory potencies varied significantly. Notably, compound 1 exhibited potent inhibitory effects on pro-inflammatory signaling, significantly inhibiting the production of TNF-α, IL-6, and IL-12p70, surpassing the bioactivity of the parent compound. Compound 2 displayed a similar, attenuated inhibitory trend, suppressing the secretion of TNF-α and IL-12p70. Compound 3 modulated the immune response by promoting anti-inflammatory cytokine IL-10 production, despite an inconsistent suppressive effect on pro-inflammatory cytokines. These results suggest that gamma-induced radiolysis is a useful strategy for enhancing the therapeutic potential of dietary phenolic compounds.

Naringenin is a flavanone recognized for its diverse pharmacological properties, including anti-inflammatory and anticancer effects. This study aimed to produce novel structures with enhanced biological activity by subjecting (±)-naringenin (1) to γ-irradiation. Compound 1 in an ethanol solution was irradiated at doses of 30, 50, 70, and 100 kGy, among which the 100 kGy dose yielded the highest concentration of radiolysis products. These radiolysis products were further processed through multi-step semi-preparative HPLC utilizing a chiral column, yielding compounds 2–5. These compounds were identified as apigenin (2) and three stereoisomers of 2-(1-hydroxyethyl)-naringenin (2,3-dihydro-5,7-dihydroxy-2-(1-hydroxyethyl)-2-phenyl-4H-1-benzopyran-4-one; 3–5) via high-resolution electrospray ionization mass spectrometry and nuclear magnetic resonance spectroscopy. The absolute stereochemistry of compounds 3–5 was determined to be (2S,11S)-, (2S,11R)-, and (2R,11S)-configurations, respectively, by comparing experimental electronic circular dichroism data and specific optical rotations. Evaluation of nitric oxide inhibition in lipopolysaccharide-stimulated RAW 264.7 cells revealed that compound 2 exhibited greater activity to the parent compound 1, whereas derivatives 3‒5 were inactive. These findings indicate that γ-irradiation is an effective strategy for structural modification and enhancing the bioactivity in flavonoids.