Patent ID: 6361815
Filing Date: 2002-03-26
Classification: C07D

Abstract:
A process for the isolation of a purified product comprising at least about 85% by weight of 3,4â€²,5-trihydroxy-trans-stilbene from a plant material containing trihydroxystilbenes and glycosylated derivatives thereof, the process comprising:(a) contacting pieces of the plant material with an aqueous solvent to form a slurry; (b) separating the contacted aqueous solvent from the slurry to isolate a first product comprising at least 10% by weight of a mixture of trihydroxystilbenes and mono-&bgr;-D-glycosylated trihydroxystilbenes; (c) loading a loading concentrate of the first product onto an MD-1 column with a stationary phase comprising a copolymer of a vinyl aromatic compound cross-linked with a polyvinyl aromatic compound; (d) eluting the MD-1 column with an elution volume comprising a mixture of alcohol and water between about 70 and 80 vol-% alcohol to isolate a third product comprising at least 20% by weight of a mixture of trihydroxystilbenes and mono-&bgr;-D-glycosylated trihydroxystilbenes; (e) loading a loading concentrate of the third product onto an MD-2 column with a stationary phase comprising polyamide resin; (f) eluting the MD-2 column with a first MD-2 gradient volume comprising a mixture of alcohol and water between about 20 and 40-vol % alcohol; (g) eluting the MD-2 column with a second MD-2 gradient volume comprising a mixture of alcohol and water having at least about 70%-vol % alcohol to isolate a fourth product comprising at least 30% by weight of a stilbene fraction, wherein the stilbene fraction comprises about 80% by weight trihydroxystilbenes; (h) loading a loading concentrate of the fourth product onto an MD-3 column with a stationary phase selected from the group consisting of C-8 to C-18 and cyano bonded silica gel; (i) eluting the MD-3 column with a first gradient volume comprising a mixture of alcohol and water between about 35 and 45 vol-% alcohol; (j) eluting the MD-3 column with a second gradient volume comprising a mixture of alcohol and water between about 50 and 60 vol-% alcohol to isolate a sixth product comprising at least about 70% of a stilbene fraction, wherein the stilbene fraction comprises at least about 75% by weight of 3,4â€²,5-trihydroxy-trans-stilbene; and (k) crystallizing the purified product from the sixth product.