Oryzaceramides A–C, acylated glucosylceramides with epidermal barrier functions, isolated from rice bran

Abstract

The gummy by-products of rice bran oil have been used as a resource of glucosylceramides (GlcCer) and ceramides (Cer), which have important skin barrier functions. We herein isolated three undescribed acylated GlcCer, oryzaceramides A (1), B (2), and C (3), from rice bran (outer layer of grain from Oryza sativa L.). The stereostructures of 1–3 were elucidated based on their spectroscopic and chemical properties. To the best of our knowledge, this is the first study to obtain plant-derived acylated glucosylceramides. We also showed that 1 significantly reduced transepidermal water loss.