Yumeng Zhai,Jinkang Ma,Xinran Liu,Fanghao Xuan,Kaiwen Hu,Shoubo Wang,Xiaoyu Feng,Lifeng Cao,Bing Teng
Two new crystals were designed and obtained: the chalcone derivative HMMP (1-(2‑hydroxy-4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop‑2-en-1-one) and the flavanone derivative 7M4MC (7‑methoxy-2-(4-(methylthio)phenyl)chroman-4-one). Yellow bulk 7M4MC single crystal with dimensions of 3 × 2 × 1 mm 3 and orange-yellow needle-like HMMP single crystal were grown by solution evaporation. 7M4MC crystal belongs to the P 2 1 space group of the monoclinic structure, which has a non-centrosymmetric structure. HMMP crystal monoclinic, belongs to the P 2 1 /m space group with a centrosymmetric structure. In the 7M4MC molecule, the methoxy and methylthio groups act as electron donors (D) and the carbonyl group acts as an electron acceptor (A), forming a d -π-A-π-D structure with an electron gradient. 7M4MC exhibits a high degree of second-harmonic generation intensity (11 × KDP), a broad transmission range (600–1600 nm, >88 %), an elevated optical energy bandgap ( E g = 2.57 eV), high thermal stability ( T m = 105 °C) and excellent dielectric properties ( ε r ≈ 2.1). This work not only provides two new crystals but also offers a viable molecular design option by changing the degree of intramolecular distortion by altering the backbone structure.
This study aimed at recycling flavonoids with glycolipid lowering activity from Chenpi processing residue produced by essential oil extraction. The crude Chenpi flavonoids obtained by ethanol reflux mainly contained flavonone (hesperidin) and polymethoxyflavonoids (nobiletin, tangeretin, sinensetin, and isosinensetin), which complementally exerted strong glycolipid lowering activity as revealed by digestive enzyme inhibitory activity, molecular docking and network pharmacology. The reducing sugar and water-soluble impurities were efficiently removed by yeast fermentation and aqueous two-phase system (ATPS) extraction, respectively. The optimal combination use of yeast (2 % w / v , CN36) and ATPS formed by 22 % ( w /w) (NH 4 ) 2 SO 4 and 25 % (w/w) ethanol improved flavonoid purity to 60.25 %, enriched flavonone and polymethoxyflavonoids by 6.69-fold, and enhanced digestive enzyme inhibitory activity, which was superior to the use of individual yeast or ATPS, unoptimized combination, macroporous resin (XAD-16), and ethyl acetate. This study was the first to develop a recyclable biophysical method for simultaneous enrichment of flavonone and polymethoxyflavonoids.