Kaempferol tri- and tetrasaccharides from Camellia japonica seed cake and their inhibitory activities against matrix metalloproteinase-1 secretion using human dermal fibroblasts

Eight kaempferol oligosaccharides were isolated and identified from Camellia japonica seed cake. The chemical structures of the isolates were determined by using chromatographic and spectroscopic techniques, such as high-performance liquid chromatography with a photodiode array detector (HPLC-PDA), one-dimensional (1H and 13C), and two-dimensional nuclear magnetic resonance (1H–1H COSY, HSQC and HMBC), ESI-Q-TOF-MS, and optical rotation. To evaluate the anti-aging efficacy of kaempferol oligosaccharides for cosmetic use, the MMP-1 inhibitory effects of the isolates were studied using human dermal fibroblasts which were cultured in HaCaT cell-conditioned media. The MMP-1 inhibitory assay results revealed that kaempferol-3-O-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 6)-O-β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranoside showed the most potent MMP-1 inhibitory activity. The basal level inhibition was 50 ppm, which indicated that C. japonica seed cake is a promising material for the development of anti-aging skin cosmetics.