Cerebrosides and Tocopherol Trimers from the Seeds of Euryale ferox

Abstract

Two new cerebrosides, ferocerebrosides A (1) [(2S,3R,4E,8E,2'R)-1-O-(beta-glucopyranosyl)-N-(2'-hydroxydocosanoyl)-4,8-sphingadienine] and B (2) [(2S,3R,4E,8E,2'R)-1-O-(beta-glucopyranosyl)-N-(2'-hydroxytetracosanoyl)-4,8-sphingadienine], two new tocopherol trimers, ferotocotrimers C (5) and D (6), and two known tocopherol trimers, IVb (3) and IVa (4), were isolated from the seeds of Euryale ferox. Their structures were determined on the basis of spectroscopic data, especially 1D and 2D NMR experiments. Compounds 1 and 2 showed cytotoxicity in the brine shrimp lethality bioassay, with LC50 values of 0.17 and 0.20 mM, respectively.

Cellular Anti-Melanogenic Effects of a Euryale ferox Seed Extract Ethyl Acetate Fraction via the Lysosomal Degradation Machinery

“…In traditional oriental medicine, E. ferox seeds have been used to treat chronic diarrhea, leukorrhea, polydipsia, renal disease, ischemic heart disease, and mouth dryness [ 2 , 3 , 4 ]. Previous studies indicated that E. ferox seeds contained tannins, tocopherol polymers, fucosterol, resorcinol, pyrogallol, cyclic dipeptides, glucosylsterols, cerebrosides, and polyphenols [ 5 , 6 , 7 , 8 ]. E. ferox seed extracts have shown significant antioxidant activity, effects on cell-mediated immunity, neuroprotective effects, and cardioprotective properties, including the prevention of myocardial ischemic reperfusion injury [ 3 , 9 , 10 ].…”

Natural Sphingadienes Inhibit Akt-Dependent Signaling and Prevent Intestinal Tumorigenesis

“…These sphingadienes (SDs) are cytotoxic to insect cells and are structurally similar to SDs that comprise the sphingoid base backbone of soy sphingolipids. Complex sphingolipids containing SDs and sphingatrienes are found in aquatic plants used for medicinal purposes in traditional oriental medicine (15-17). Thus, we hypothesized that SDs might be the active component of soy that inhibits intestinal tumors.…”

A new 3,4-seco-cycloartane from the leaves ofHopea odorataRoxb.

“…abiesatrine J or 3,4-seco-cycloart-4(28),24-diene-3,26-dioic acid (2) (Yang et al 2010), mangiferonic acid (3) (Zhang et al 2003), friedelin (4) (Akihisa et al 1992), epifriedelanol (5) (Salazar et al 2000) and b-amyrine (6) (Mahato & Kundu 1994)), as well as two tocopherol trimers IVa (7) and IVb (8) (Row et al 2007) (Figure 1). Structures of known compounds were determined by comparison of their spectral data with those previously reported in the literature.…”