Background and overview[1]
C-Veratryl glycol is one of the chemical components of wolfberry. Lycium is a traditional Chinese herbal medicine in my country. It was first recorded in the “Shen Nong’s Materia Medica” and has been recorded in detail in successive generations of herbal medicine. The fruit is used as medicine and is called wolfberry. It tastes sweet and has a neutral nature. It has the effects of nourishing liver and kidney, replenishing essence and improving eyesight. It mainly treats liver and kidney yin deficiency, dizziness, waist and knee pain and other syndromes. Many experiments in modern immunology and clinical medicine have shown that wolfberry fruit and wolfberry polysaccharide can effectively improve the body’s immune regulatory function, treat diabetes and its complications, and have anti-mutation, anti-tumor, anti-fatigue, delay aging, improve eyesight, protect liver, and lower blood sugar. and other effects. There is not much research on wolfberry seeds. They are generally used to extract wolfberry oil, which has medical and health effects. The residue after extraction is regarded as waste. However, wolfberry seeds and fruits are included together, and the seeds account for about a quarter of the dried fruit. One weight, in order to develop and utilize wolfberry seeds and the waste residue after extracting wolfberry oil, we conducted research on its chemical composition and biological activity.
Preparation[1]
The preparation of C-veratrolyl glycol is as follows: 1.00kg each of wolfberry seeds and the residue after extracting wolfberry oil are extracted with methanol ultrasonic 3 times, the extracts are combined, and dried under reduced pressure to obtain 8.97g of total methanol extract. The extract has anti-α-glucosidase activity with an IC50 of 2.33mg/mL. After the total methanol extract was dissolved in water, the mixture was extracted three times with equal volumes of n-hexane and ethyl acetate. The solvent was recovered under reduced pressure to obtain 1.90 g of n-hexane extract and 1.30 g of ethyl acetate extract. The remaining aqueous layer was processed through a macroporous resin column and eluted with methanol to obtain 0.52g of methanol eluate and 4.61g of water eluate. Using α-glucosidase activity system tracking, it was found that n-hexane extract, ethyl acetate extract, and methanol eluate all showed certain α-glucosidase inhibitory activity, with IC50 of 2.11 mg/mL and 1.57 mg/mL respectively. mL, 1.89mg/mL. Therefore, the above three parts were separated by silica gel column chromatography, ODS column chromatography and high performance liquid phase preparative chromatography to obtain 14 compounds. The separation flow chart is shown in Figure 2.
Compound 12 is C-veratrolylglycol:
White solid (methanol) with dark spots at 254nm. The molecular formula is C10H12O5. The low-field region of the hydrogen spectrum gives a set of aromatic proton signals of the ABX coupling system δ7.58 (1H, dd, J=8.5, 2.0Hz, H-6′), 7.57 (1H, s, H-2′), 6.88 (1H, d, J=8.5Hz, H-5′), it is speculated that there should be a 1, 3, 4 trisubstituted phenyl fragment in this compound; the high field region gives a set of oxygen-connected protons of the AM2 coupling system Signals, respectively, are methylene and methine proton signals, δ5.11 (1H, dd, J=11.7, 5.3Hz, H-2), 3.88 (1H, dd, J=11.7, 4.3Hz, H-3 ), 3.73 (1H, dd, J=11.7, 5.3Hz, H-3); a methoxy proton signal δ3.92 (3H, s). The carbon spectrum gives 10 carbon signals, 6 of which are aromatic carbon signals and one carbonyl carbon signal δ199.7 (C=O) in the low field area, and one oxymethine carbon signal and one connected oxymethine carbon signal in the high field area. Oxymethylene carbon signal δ76.8 (C-2), 66.3 (C-3), it is speculated that the compound is an aryl ketone compound. Based on the above data, the compound was identified as 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (2,3-dihydroxy-1-(4-hydroxy-3- methoxyphenyl)propan-1-one).
Main reference materials
[1] CN201210347818.1 Method for extracting α-glucosidase activity inhibitor from wolfberry seeds and the residue after extracting wolfberry oil and its use
